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DILF | older!harry

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Summary: Y/n meets an older man at a bar and she's not taking no for an answer. Harry likes her persistence.

A/N: This was requested + this! Also, please think before you judge Y/n. She is very bold and confident in this. Maybe even a little pushy but Harry likes it (even if at first he doesn't give that impression). Also he's single so this isn't cheatrry!

Word Count: 6,580

Warning: age gap, smut, alcohol consumption (light)

. .

"That one. Total dilf. He looks grumpy. Bet you can't crack him."

Y/n laughed at her friend and looked down at her red-painted nails before narrowing her gaze on the attractive older man who was seated at the corner of the bar alone. He was nursing a whisky and he did look rather sullen. Unapproachable even.

"Why him?"

"Because he's hot. And I'm curious to see if you can get him to smile at least," Warren raised her brows, "I dare you."

Y/n tilted her head and assessed him. He was nice and big, taking up a decent amount of space at the bar, broad shoulders and back hunched as he leaned his muscular forearms on the wood of the bar top. Meaty hands placed on either side of his lowball glass. Thick brown waves on top of his head with a bit of silver coming in at the temples. But the handsome features on his face really set him apart. His granite jawline gave way to stubble that stretched over his skin and shaded in the spaces around his pink lips.

If she could "crack" him she wasn't sure she'd want just a smile. He looked yummy enough to eat.

Drinking down the last of her martini she pointed at Warren and then Tara, "Fine. Give me twenty minutes and I'll have him eating from the palm of my hand."

Tara laughed, "If you say so…"

She placed her heeled feet down on the floor and brushed her hands over her dress, "Oh, I do say so. Just watch and learn, ladies."

Y/n wasn't quite that confident, but she wasn't about to say no to dare. And she could hold her own when it came to flirting. She liked getting a little attention and if she could garner this one's interest it might be fun.

She sauntered up to the bar behind the man and noticed the way his t-shirt stretched over his lats and tapered loosely down at his waist. The guy was fit. And lucky her, there was an open stool next to him.

Sliding onto the seat she waved at the bartender to order another drink. She'd need all the courage she could get, in whatever form she could get it.

Tapping her long nails on the lacquered wood she felt nerves thrumming through veins before turning toward the man finally. He hadn't seemed to take note of her yet, which honestly was unusual in most cases. Maybe she thought too highly of herself but men tended to notice her right away. She appreciated the challenge, though.

Reaching her hand into his space to greet him, she pushed down her nerves to sound steady as she spoke, "I'm Y/n."

She watched his brow furrow as he turned to look at her hand and then up at her eyes, his expression, which she expected would soften once he looked at her, was unamused. A single light overhead lit the tops of their heads as a shadow cast over the side of his face and he didn't make a move to shake her hand, "And I'm old enough to be your dad."

A surprised scoff fell from her lips as she moved her hand away from him. She wiggled in her seat and crossed her leg over her thigh toward him, gulping down the initial rejection with as much grace as she could muster, "I think you're jumping to conclusions about my intentions. But so what if you're older than me? I don't mind. We're both adults, right?"

An unimpressed grunt rumbled from his throat before he took another sip of his whisky and he looked away from her toward the TV that hung not far away from where they sat.

The bartender placed her olive martini down on the bar in front of her, "It'll be on Y/n Y/l/n. I already have an open tab."

A sip of the salty drink felt warm down her throat. So he was going to be a bit tough to crack. She turned to look at her friends who were grinning in her direction.

Straightening her back to feel more confident she tried again, "So you're not gonna tell me your name even?"

Without looking at her, he licked his lips and ticked his jaw, "Y/n, I think it's past your bedtime."

She smiled at that. He'd said her name, which meant he'd been listening, "My bedtime is whenever I say it is, not when some grouchy stranger says."

He puffed out an amused laugh through his nose, "I am a stranger. Which means you should be cautious, little girl. Your dad didn't teach you about things like that?" He turned to look down at her again, and that time she saw the soft green color of his eyes as the light hit his face just right.

But now she was really determined. She smiled brightly at him and let her eyes coast over his tattooed arm and then back up to his face, "Are you telling me you're dangerous?"

He still didn't smile as he shook his head like he was surprised by her gall, "Do your parents know what you're up to tonight?"

"I'm 24. Graduated from college, live on my own, pay my bills, have a full-time job. You seem to be awfully worried about my parents. I can take care of myself just fine."

Just then another person sat down next to the man Y/n was trying to whittle away at. He poked his elbow at him, "Who's this?"

"Don't know. Someone who's about to go back to her table with her little girlfriends."

Biting her lip she traced the rim of her martini glass with her fingertip, keeping her eyes set on the handsome tattooed one, "Not even a smile. Just one? Please?"

"Like I already said, I'm way too old for you."

The other man leaned over and reached to tap Y/n's shoulder, "Hey. Forget about Harry, here. You can bring me home with you if you're looking for a daddy tonight."

She frowned and looked him up and down to asses. He was late 40s perhaps, wearing a local band t-shirt, ripped jeans, and a backward cap to make himself appear a little more youthful. "No thanks. You'd know if I was interested in you."

Harry bit the inside of his cheek to stop himself from smiling at her retort. She was definitely too young but he liked her spunk.

"Now, Harry…" she said his name slowly as she leaned a little closer, "I've got your name thanks to your friend. Can I have a smile?"

"Why?" He stared down at her, the caress of his gaze felt infinite and she found her skin convecting in its wake. He might be hard to crack but this one would be worth it, she determined.

She sighed and slid her finger dangerously close to his wrist as he looked down at her nail and watched her trail it near his arm, "I just hoped to see you smile is all. Too handsome to have such a sour scowl on your face."

"And you're hardly old enough to be so confident to walk up to a strange man at a bar."

She laughed and tilted her head, "You planning on doing something bad to me, Harry?"

And that. That pulled a reaction out of him that spread over his features slowly as he shook his head in disbelief, "Darlin', you wouldn't be able to handle me."

Her eyes widened slightly. Now she was definitely not giving up. Y/n wasn't one to fail and Harry might be making her work hard for it but she couldn't imagine it wouldn't be worth it in the end.

"Is that a challenge or something?" She softly scraped her nail over his tattooed wrist and Harry watched her red nail work over his skin.

His resolve was fading fast. She could tell he wasn't going to keep denying her. And why should he? If he was single, which he appeared to be, what was the harm in having a little fun with someone younger? Y/n didn't mind. And he certainly shouldn't either.

"If it were a challenge you'd know it. Lots of other guys here, Y/n. Go enjoy your night with someone closer to your own age."

She sighed in annoyance. But he hadn't moved his arm away from her and she was going to take that as a sign.

Dragging the toe of her shoe into his shin she grinned, "I don't want to enjoy my night with someone my own age. Not tonight anyway. I think you've convinced me that I need to test out this theory of yours. That you think I can't handle you. Cause I bet I can."

With his eyes piercing into hers, he took another sip of his drink. She thought she might have just convinced him to give her a smile at the very least because it looked like he was weighing his options. And if she could get him to smile she might have luck with the rest.

He tilted his chin upward for a moment, eyes aimed at the ceiling like he was calling on a higher power for strength, "Go back to your friends, Y/n. Any other man here would love to have your company."

"But you wouldn't love to have my company?"

"I mean… I'm still here," the other man raised his hand and leaned into Harry, "Honey we could have so much fun. Any man who'd turn you down is either battin' for the other team or more likely," he chuckled and pushed his shoulder into Harry's teasingly, "He can't get it up anymore."

Y/n's mouth dropped open at that and Harry turned to look at the man. She wished she could see the look on his face, "Sit the fuck back down, John. She already told you she's not interested in you."

"Yeah, and you're not interested in her so what's it matter to you? Look at her, Harry. Practically begging you. Young and bubbly… Tight—"

Harry's hand covered John's throat as he pushed him away, nearly making his stool topple over, "Get the fuck outta here. You had too much whisky tonight."

"Aww… come on Harry… I was just jokin'!"

She watched as he stood from his stool and looked down at John, "And you thought that was funny? You like making jokes about women like that?"

The man put his hands up in surrender, "I'm out. Here…" he threw a wad of cash on the bar top before he moved past Harry and then looked at Y/n, "My apologies if I offended you."

They watched as John left the bar quickly and then Harry sat back down before he waved at the bartender and signaled for the check, "Just the one whisky neat."

"You're leaving already? Night's still young, Harry."

He sucked at his teeth as he scraped his gaze over her face and down to her cleavage. She smiled when she watched the path his eyes had taken.

The bartender handed him the bill and Harry leaned over to pull his wallet from his back pocket.

She scooted closer to him, "You headed home?"

He nodded, but not necessarily in answer to her question, it was more of an appraisal kind of nod. He was still silent as he pulled cash out of his wallet.

"Thanks for that, by the way. I'm sure John's a nice guy and all but he's not really my type. And I'm sure he was wrong about you."

That got his attention. Harry flicked his gaze back to hers, "Wrong about me?"

She smiled, "The part where he said you couldn't get it up. You're not that old. I'm sure you still can. Right?"

He clenched his jaw and breathed out of his nostrils like he couldn't believe she'd asked him such a thing. He handed the bartender his cash with a nod before he stood up from his stool.

"Huh. Since you're so quiet about it maybe he was right," she goaded, pressing her lips together to flatten her smile as she looked up at him through her lashes.

Harry placed a palm down on the bar top next to her hand and leaned over her, "You're out of your depth here, Y/n."

"Now, you don't really know that do you? Just because I'm younger than you doesn't mean I don't know what I'm doing."

"You're awfully pushy. Not used to hearing no, are you?"

Y/n watched as the edge of his mouth lifted in amusement and she widened her eyes and pointed, "You're almost smiling."

He shook his head and looked around the bar before pinning his gaze back to hers, "I hope you enjoy the rest of your night. But your luck has run out with me, princess."

Harry stood to his full height and Y/n decided to try one last time, "So it's true then. What he said."

He stopped and turned to look back at her, a slow burning heat behind his gaze, "Couldn't be further from the truth."

She smiled and slid off her stool to stand in front of him. His height was impressive, "Prove it."

The line of his jaw hardened, turning his cheekbones into slashes of tension. His eyes simmered as he weighed his options. Finally, a hint of a smile stretched over his mouth. A small one, but still.

"I don't need to prove anything to silly little girls."

"Good thing I'm not a silly little girl. I'm a grown woman, Harry."

Y/n knew she was pushing it. She'd never needed to throw herself at any man before. But because of that, she wasn't used to rejection either. Maybe it was a good lesson for her ego. She knew her big fault was how entitled she could act sometimes. But that was partly thanks to how she was raised. It's better to act like a man to get what you want in life, her dad told her. And so far, that had been true. Some women balked at her confidence and her bold attitude. She wasn't demure or sweet enough. And men would often refer to her as a bitch or say that she was trying too hard.

She'd work on her ego another time. But right now? She was focused on winning this battle.

"What do you want with someone like me anyway? Hm? I'm old, Y/n. What's in it for you?"

Blinking her eyes she shook her head, "You're not old, first of all. Secondly, you're really attractive. It doesn't need to go much deeper than that, does it? I just think you're handsome. And I do kind of like a challenge."

"I can see that you like a challenge. It's the only reason I haven't walked out that door yet. Kind of relentless."

She smiled, "So it's working?"

Another half-smile worked its way up his mouth as he laughed in disbelief, "Are you surprised that it is?"

His pupils coasted over her figure and then back up to her face. The warmth of his gaze singed her skin like an open flame.

"I guess I just didn't know how difficult it'd be with you."

He licked his lips, "Difficult. You have no idea. But looks like you're about to find out. Go tell your friends what's going on. Meet me out front."

Y/n watched him turn and walk away. She was shocked. For a minute she thought he wasn't going to go for it at all.

Shaking off the sudden surprise of having gotten to him she settled up with the bartender and then stopped at the table with her friends. They were just about to give her condolences for having oversold her ability but she interrupted. "He's waiting for me outside. Location is on. Don't wait up!"

Harry was leaning against a black car in the parking lot when she stepped out of the doors. The moment he saw her he pushed himself off the car and opened the passenger door for her.

It was going to be tricky to maintain the kind of confidence she'd been feigning with him up until then but there was no part of her that didn't want to find out what he could show her.

She watched as Harry sat down in the driver's seat and started up his car. He took up too much space in the seat. His big hand wrapped around the leather steering wheel while his other encased the shift stick. Even the way he drove was turning her on.

She was pleased that she'd wormed her way under his skin and that he'd given in. She'd try her best to make it worth his while. Reaching across the console she put her hand on his thigh and he glanced down quickly before setting his gaze back on the road.

Now, Harry had slept with younger women a couple of times. He generally preferred someone closer to his age because he liked the confidence and experience that came with age. Women in their 20s were often in a different stage of life and that was fine –normal even, but it just usually wasn't a match for him. Not sexually and not mentally.

But Y/n was unusually confident for being so young. Persistent. He liked it, he couldn't lie. Whether or not she really had much else going for her beyond confidence, he guessed he'd find out. Well, she was very cute too. She did have that in her favor.

And Y/n at least seemed like she knew what she wanted. It was flattering as well. Being approached by such a pretty young thing. He figured the moment he told her to go back to her friends she'd give up but she was just fiery enough that she wasn't deterred.

When she ran her nail over his wrist he knew he was screwed. She was just close enough that he could smell her perfume and then she nudged her shoe into his shin and all he could think about was that she really wanted to be shown a good time and if anyone could it was him.

Harry knew his way around a woman's body. They were all different and he liked finding all the buttons and things that made them purr. In his experience, though, the younger the woman, the less she knew her own body. He didn't know if Y/n was just talking a big game but he was about to find out.

He stayed quiet as she ran her hand down his thigh and he shifted as the car accelerated past the green light. He'd see if she'd do anything with her hand but maybe she'd just pet at him like a novelty toy. He didn't expect—

"This is okay?" She asked him, her tone sultry as she palmed at his crotch.

He licked his lips, "Have at it."

His cock fattened up nicely with not much effort on her part. Proof that he definitely could get it up. Plucking at his button she looked from his face to her fingers as she leaned further over the console to reach her hand into his open pants to help him with the awkward angle of his dick. He seemed to appreciate that as he shifted under her palm.

Rubbing over his heather grey briefs she peeled down the elastic band the slightest to get a peek. The dark shade of pink on his tip matched the muted raspberry of his lips. She slid the pad of her middle finger over the slit and he softly inhaled through his teeth.

She wouldn't be able to give him roadhead like she wanted. It was impossible with the stick shift in the way. But she could wrap her fingers around his shaft and feel him under her palm until they got wherever they were going.

"Mmm… It's so big, Harry. Knew you would be. Might be the biggest I've seen in person. Can't tell yet, though. Have to wait to see when we've got these off."

Harry pushed a laughed breath through his nose. She was a bold thing. Her assertiveness was a turn-on. He didn't like meek and shy. Not when it came to sex.

When she spit into her palm and smeared it down his length, the best she could, he parted his lips and stepped on the gas. She was already exceeding any expectations he had for her. Maybe she'd prove him wrong.

Her nail scraped the underside of him and she moaned, "Really want it in my mouth."

He gulped harshly and ticked his jaw, "Just be patient. I'll let you put it in your mouth soon enough."

"And where are we going? Your place?"

He nodded, "Just a few minutes away."

She squeezed around him and pulled upward slowly. She knew already, he was well above average and she was going to have to work to give him a proper blowy.

His house was a one story, the driveway at the front with a garage attached. He lifted his hand and pushed on a device that was clinging to his sun visor and the garage door began to open. There was a covered motorcycle along the back wall and then the garage door closed after he shut off the engine.

She moved her hand away and unbuckled herself as he got out. When she reached down to pick up her little purse she realized her panties were already wet. She grinned as she stepped out, adjusting her dress before closing the door, and then followed behind him as he led her into a dark hallway.

When he turned on the lights she took it all in. Hardwood floors led into a dining area and then a kitchen. Hung on the walls were photos of himself with two children and then more framed photos with just the kids.

"Do you have kids?"

"I do. Boy and a girl. 7 and 10."

"You're not married are you?"

He laughed, "If I were you'd have known. Wouldn't have been out in the first place if I had a wife waiting for me at home."

She nodded as he turned on the kitchen light and pulled out two glasses before filling them with water.

"Divorced?"

Handing her a glass he squinted, "Yes."

She took a sip. He was a man of few words she'd gathered. She looked around the kitchen. Wood cabinets, an outdated laminate countertop, stainless steel appliances. The space could use some updating but it was large and he had a big pantry.

Sitting the glass down on the counter she watched him closely. His pants were still unbuttoned. She eyed the space at his crotch as he placed his own glass down next to hers.

"It's not gonna suck itself."

She laughed and looked up at him. He had a genuine smile on his face that time. The first real smile she'd seen from him all night. A healthy row of clean teeth, a dimple…

"Hmm… I think you're right. Let's see what we've got…"

She moved in front of him and placed her hands on his pants to push them away but before she could inch them down he wrapped his meaty hand around the back of her neck and drew her into his chest. His mouth was warm and soft. His tongue tasted like the whisky he'd been drinking.

Letting go of his pants she held onto his biceps as he used his free hand to push her hips against his. Still nice and hard. He ran his tongue over her lips and she moaned into his mouth. He worked his warm lips down to her jaw and then he licked upward on her neck, the wet patch was cool on her skin from the air in the kitchen. He did it again and her knees almost gave out. She hadn't been licked like that before.

He kissed over her clavicle and then drew his tongue over her flesh. Her heart was thrumming quickly and she squeezed his strong arms when he rutted against her.

"You good at sucking cock, Y/n?" He pushed his nose against her jawline and the hot breath from his words scattered over the skin on her neck.

"I want to be," she spoke breathlessly, eyes fluttering closed as he mawed at her throat.

He parted from her neck and looked down at her, half-lidded gaze and spit-slicked lips, "Go on."

Instantly she dropped to her knees as her fingers worked deftly at pulling his pants down and then his underwear. She'd sucked a handful of dicks so she knew a couple of moves.

Getting her hand around his thick shaft proved to be a small challenge. To say he was thick… understatement. Long too. His tip was smooth, mushroomed with ridges along the length that she hoped she'd get to feel later on. His was the kind of cock that women dreamed of.

Looking up at him she licked her palm and used her spit to pump him slowly. Another glob over his tip for good measure. Then she pressed a kiss to the base of him, just over his sac, and screwed her eyes upward to watch his expression as she licked his balls, one side at a time. She wound her tongue all around to wet him before sucking at one side, pulling it into her mouth and he let out a ragged breath, his dark pupils spreading inky until the soft green had almost vanished.

He liked it.

She worked around the other side, sucking him in again and swirling her tongue softly underneath the tender bits. He gripped the counter behind himself.

Pulling off she straightened her back and licked upward, feeling every delicious thick ridge along his shaft until her tongue met his smooth crown. Laving every crevice of his tip, she dipped her tongue into his slit and then ran it under the frenulum before she wetted every inch of his glans.

Her mouth was watering when she parted her lips around him and flitted her gaze upward. He was watching her with a slack jaw as she took him a little deeper. He cradled the back of her head and moaned.

"Just suck the tip…."

She blinked up at him and pulled her lips just over the lip, swirling and suckling around him like he wanted.

"Fuck. Just like that." His hand at the back of her head was easy. He didn't push or pull. It was more like a pleased gesture as his fingertips flexed around her skull gently.

Y/n would have liked to have gone deeper. Wanted to show him her best work. But he seemed rather happy with what she was doing.

She bobbed a couple of times, only to slide her lips back to his tip. Her pace was slow when she began to stroke his length with a little twisting motion.

He was big. She knew she could take more but in a way, she was grateful that that was all he was asking for.

A groan fell from his chest and he bucked forward, his cock slipping down her tongue and she sucked, drawing more of him in as she moved her hands away.

"Goddamnit, you're good."

She took that as permission to go deeper. Relaxing her jaw she closed her eyes and held her breath, pushing down to her limit. She filled her throat with his cock the best she could and gurgled around his tip.

He coughed out a moan and then thumbed at her cheek, "Alright, that's good."

She pulled off of him. His heavy cock aimed right at her face when she sat back on her knees and looked up at him, "I can do better than that."

He laughed and put his hand out for her to take, helping her stand up, "I bet you can. Come on."

Harry kept her hand in his as he led her to his bedroom. It was just past the dark living space and he turned on a floor lamp on the opposite side of the room from the bed. When he turned back toward her he cupped her face and kissed her again.

She pressed her hand into his warm, hard chest and he reached around the back of her dress to pull the zipper downward, his fingers dragging down her skin as he went. His touch sent a tremor down her spine as continued kissing her wetly.

He stepped back, helping her out of her dress until it fell to the floor. His eyes raked over her body and he smoothed his hands over her hips and up to her bra-covered breasts. He stepped in closer, walking her backward toward his bed. He put his hands back on her hips and nudged her to sit before he reached down to lift her leg up by her calf, removing her heels, one at a time.

Y/n's thong was drenched. She stared at him while he placed her shoes side by side at the foot of the bed and then he placed his big palms on her thighs, pushing her legs open, "Lie back."

She let her back hit the mattress as Harry got to his knees on the floor. An arm reached under her thigh as he spread her apart and then she felt her panties being pulled at until her her wet pusslips were right in his face. He groaned and felt a hand slide up the inside of her thigh. He pressed his mouth over her mons and looked up at her before he opened his mouth wide and drew his tongue through her crease making her gasp.

"Get your bra off."

She pushed herself up slightly and worked at the clasp of her bra between moans as Harry continued licking at her pussy. When she pulled her arm through the flimsy material he lifted his head and reached around her back, pulling her closer to the edge of the bed and he sucked a nipple into his mouth.

"Oh, fuck!"

Y/n's finger and her long nails pushed into Harry's hair and scraped at his scalp as he licked and pulled at each nipple. He buried his face between her tits and let out a low sound, like he was murmuring something to her but only her breasts were allowed to hear it.

When he sunk back down he pushed at her so she'd lie back and he started in on her clit, one hand holding her panties to the side as he devoured her glistening cunt.

She kept feeling like she was going to slide off the edge of the bed but Harry's grip on her kept her still. His tongue and his lips were magic as he drew her to her end. She yanked at his hair and babbled his name on repeat as her spine bowed off the bed when she came.

Her chest was still rising and falling heavy when she felt her body being pushed upward. She popped her eyes open and watched him roll a condom over his shaft before he kneed back up onto the bed next to her. He was stark naked. His body was insane. Thick muscle and masculine everything. Tattoos scatter over his arms and chest.

Fuck, she muttered under her breath.

"Flip over, for me," his deep voice was husky as he motioned toward her to move.

She rolled to her stomach and she felt his fingers slide between the band of her panties and her hips as he pulled them down her legs.

"Ass up a little. I want to see all of you, Y/n."

She grinned and turned to look at him over her shoulder as she lifted her hips and spread her thighs. His lips were parted as he grabbed her ass and squeezed, making her cheeks spread apart. He inhaled sharply through his teeth and then dipped in, kissing her pussy from behind before licking upward over her ass.

She squealed quietly and bit her lip, still watching him behind her as he lifted, a lopsided grin on his face. He gazed at her as he fisted the base of his cock and slid the head up and down her soaked folds before he tipped his hips to push in just the tip.

"Gorgeous. Gonna look even better wrapped around cock. You like anal?"

"Never tried it."

He licked his lips and pressed his lips together as he looked at the spot where his dick was pressed against her cunt, "Figured. S'alright. Pussy's my favorite anyway."

"We could try… if you want."

He looked back into her eyes, a cocky smile on his face, "Your little hole would need to be trained. And that takes time. So, there will be no anal tonight. Not gonna try and hurt you. But that's a cute thought."

He canted his hips inward, eyes on hers and her mouth dropped open when she felt her entrance splitting open for him. She was tight, but so slick, it only took a few slow thrusts until he was buried in with a low grunt. He pulled back and then pushed his entire length into the hilt.

"Fuck—fuck!" She cried and stuffed her face into the blankets.

"Too much?"

"No! It's so good. You're just so big…" She began to send her hips back against him and Harry slowly fucked in to match her pace. His eyes were everywhere. On her puss getting split open on his cock, the curve of her lower back, the swell of her ass.

He just knew she'd look so sweet with her ass stuffed too, but good things like that couldn't be rushed which was a shame.

Every thrust was gushy wet. Y/n bubbled out small moans every time his dick brushed deep into her guts. It was better than she imagined. The way he filled her to the brim was going to turn into an addiction. She'd never slept with any man that had her wanting seconds before they'd even finished.

"Oh my god…" she mewled into the comforter.

"Fuck, I know, baby…"

She fit him like a glove, it was perfect. He went in a little faster, balls thudding against her skin rhythmically making her bounce forward as she spread around his girth. When he ground in she arched her back deeply and let out a soft groan, her hands fisted at the blanket and Harry reached around and smeared his fingertips over her clit.

It had her panting and pushing into him feverishly. She'd needed the friction on her throbbing button and he'd found it easily, thick, rough fingerprints slicking back and forth as he rutted in and in. It sent electrical sparks over her limbs.

"Like that? Needs her clit touched? Shit baby, act like you've never been touched by a man right here before…" he plucked at her like he was playing the guitar and she began to fade, her moans getting caught in her chest.

He could feel her walls tightening around him as he drove in deep.

"Fuck, Harry— fuck!"

He grinned as he watched her shudder, "Give it up, Y/n. There you go…"

She began to pulse around him, a constant stream of nonsense falling from her lips as he stroked against her channel and pushed deep into her tummy, his fingers still working her clit with ease.

Just as her body had tipped and oxygen returned to her lungs he pulled out and she felt him taking her hips and turning her around to her back. Harry grabbed her ankles and lifted until each was settled over his shoulders and pushed back inside of her, cock drilling down to her core making her teeth chatter at the way he split her down the middle.

Harry leaned over her, cock buried deep as she watched her pretty face twist up with pleasure. Plapping into her, her tits wobbled as his balls tightened against his body. The harder he plunged in, the more her legs shook. Soon, her ankles had slipped down and her feet hit the mattress as he continued drilling into her. His face was flushed hot, lips parted, muscles tensed.

Reaching up to his neck she smoothed her fingers over his warm skin and he lowered his chest down to hers and kissed her. That filthy tongue ran over her lips and he sloppily sipped at her between sucking at her lips. Her brain had turned to jelly.

She felt his hand on her outer thigh squeezing and brushing as he fucked down into her. "Mmm… fuck, Y/n, m'gonna come…"

He trembled over her, thick thighs pressed down and flexed as he rutted in and in and in, and then… he stilled. A deep, guttural moan vibrated through his chest down into hers.

She sighed when she felt him throbbing, pumping into his condom. Her fingers caressed the muscles over his back and she gasped when he bucked in harshly, once more as he emptied the last of his come into the rubber wrapped around his cock.

He slowed his kisses until they were lazy little pecks and then he looked down at her, his chest heaving. She was already grinning up at him.

"What?"

She blinked her eyes, "That was fun."

He puffed out a breath, "I guess that's a good way to describe it."

Harry was a gentleman as he pulled out slowly and helped her off the bed and led her to his bathroom. He helped her clean up and listened to her tell him about her job —just reminding him that she was an adult after he commented on her being so young again.

When she picked her dress up off the floor and started to step into it, Harry frowned, "What are you doing?"

She stopped and raised her brows. "Getting dressed. Was gonna call an Uber. I'm sure you don't want a stranger in your house all night," she laughed.

Harry pulled at her hand, making her drop her dress, "What kind of men have you been hanging out with that let you leave in an Uber at 2 am? You'll stay here."

She opened her mouth and then closed it in surprise before tilting her head in confusion, "Really? I just assumed—"

"You'll stay the night here. There's no way in hell you're getting an Uber at this time of night. It's dangerous."

She grinned and shrugged, "Well then… can I have a shirt or something to sleep in?"

He placed his warm hands on her hips, "You can have a t-shirt if you like. I prefer to sleep naked myself."

"Oh yeah? I usually do too as a matter of fact."

He held her out in his arms and eyed her naked frame, "Looks like we're both good to go then. We'll get you sorted in the morning. I'll give you a ride home then."

"I think you just want to keep me here with you," she chuckled.

Harry shook his head and released her hips before he popped her on the bottom with his palm. She bleated out a laugh.

"Get your ass in bed before I change my mind."

"Yes, sir."

. .

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[gurugirl]

DILF | older!harry

MAIN MASTERLIST

Summary: Y/n meets an older man at a bar and she's not taking no for an answer. Harry likes her persistence.

A/N: This was requested + this! Also, please think before you judge Y/n. She is very bold and confident in this. Maybe even a little pushy but Harry likes it (even if at first he doesn't give that impression). Also he's single so this isn't cheatrry!

Word Count: 6,580

Warning: age gap, smut, alcohol consumption (light)

. .

"That one. Total dilf. He looks grumpy. Bet you can't crack him."

Y/n laughed at her friend and looked down at her red-painted nails before narrowing her gaze on the attractive older man who was seated at the corner of the bar alone. He was nursing a whisky and he did look rather sullen. Unapproachable even.

"Why him?"

"Because he's hot. And I'm curious to see if you can get him to smile at least," Warren raised her brows, "I dare you."

Y/n tilted her head and assessed him. He was nice and big, taking up a decent amount of space at the bar, broad shoulders and back hunched as he leaned his muscular forearms on the wood of the bar top. Meaty hands placed on either side of his lowball glass. Thick brown waves on top of his head with a bit of silver coming in at the temples. But the handsome features on his face really set him apart. His granite jawline gave way to stubble that stretched over his skin and shaded in the spaces around his pink lips.

If she could "crack" him she wasn't sure she'd want just a smile. He looked yummy enough to eat.

Drinking down the last of her martini she pointed at Warren and then Tara, "Fine. Give me twenty minutes and I'll have him eating from the palm of my hand."

Tara laughed, "If you say so…"

She placed her heeled feet down on the floor and brushed her hands over her dress, "Oh, I do say so. Just watch and learn, ladies."

Y/n wasn't quite that confident, but she wasn't about to say no to dare. And she could hold her own when it came to flirting. She liked getting a little attention and if she could garner this one's interest it might be fun.

She sauntered up to the bar behind the man and noticed the way his t-shirt stretched over his lats and tapered loosely down at his waist. The guy was fit. And lucky her, there was an open stool next to him.

Sliding onto the seat she waved at the bartender to order another drink. She'd need all the courage she could get, in whatever form she could get it.

Tapping her long nails on the lacquered wood she felt nerves thrumming through veins before turning toward the man finally. He hadn't seemed to take note of her yet, which honestly was unusual in most cases. Maybe she thought too highly of herself but men tended to notice her right away. She appreciated the challenge, though.

Reaching her hand into his space to greet him, she pushed down her nerves to sound steady as she spoke, "I'm Y/n."

She watched his brow furrow as he turned to look at her hand and then up at her eyes, his expression, which she expected would soften once he looked at her, was unamused. A single light overhead lit the tops of their heads as a shadow cast over the side of his face and he didn't make a move to shake her hand, "And I'm old enough to be your dad."

A surprised scoff fell from her lips as she moved her hand away from him. She wiggled in her seat and crossed her leg over her thigh toward him, gulping down the initial rejection with as much grace as she could muster, "I think you're jumping to conclusions about my intentions. But so what if you're older than me? I don't mind. We're both adults, right?"

An unimpressed grunt rumbled from his throat before he took another sip of his whisky and he looked away from her toward the TV that hung not far away from where they sat.

The bartender placed her olive martini down on the bar in front of her, "It'll be on Y/n Y/l/n. I already have an open tab."

A sip of the salty drink felt warm down her throat. So he was going to be a bit tough to crack. She turned to look at her friends who were grinning in her direction.

Straightening her back to feel more confident she tried again, "So you're not gonna tell me your name even?"

Without looking at her, he licked his lips and ticked his jaw, "Y/n, I think it's past your bedtime."

She smiled at that. He'd said her name, which meant he'd been listening, "My bedtime is whenever I say it is, not when some grouchy stranger says."

He puffed out an amused laugh through his nose, "I am a stranger. Which means you should be cautious, little girl. Your dad didn't teach you about things like that?" He turned to look down at her again, and that time she saw the soft green color of his eyes as the light hit his face just right.

But now she was really determined. She smiled brightly at him and let her eyes coast over his tattooed arm and then back up to his face, "Are you telling me you're dangerous?"

He still didn't smile as he shook his head like he was surprised by her gall, "Do your parents know what you're up to tonight?"

"I'm 24. Graduated from college, live on my own, pay my bills, have a full-time job. You seem to be awfully worried about my parents. I can take care of myself just fine."

Just then another person sat down next to the man Y/n was trying to whittle away at. He poked his elbow at him, "Who's this?"

"Don't know. Someone who's about to go back to her table with her little girlfriends."

Biting her lip she traced the rim of her martini glass with her fingertip, keeping her eyes set on the handsome tattooed one, "Not even a smile. Just one? Please?"

"Like I already said, I'm way too old for you."

The other man leaned over and reached to tap Y/n's shoulder, "Hey. Forget about Harry, here. You can bring me home with you if you're looking for a daddy tonight."

She frowned and looked him up and down to asses. He was late 40s perhaps, wearing a local band t-shirt, ripped jeans, and a backward cap to make himself appear a little more youthful. "No thanks. You'd know if I was interested in you."

Harry bit the inside of his cheek to stop himself from smiling at her retort. She was definitely too young but he liked her spunk.

"Now, Harry…" she said his name slowly as she leaned a little closer, "I've got your name thanks to your friend. Can I have a smile?"

"Why?" He stared down at her, the caress of his gaze felt infinite and she found her skin convecting in its wake. He might be hard to crack but this one would be worth it, she determined.

She sighed and slid her finger dangerously close to his wrist as he looked down at her nail and watched her trail it near his arm, "I just hoped to see you smile is all. Too handsome to have such a sour scowl on your face."

"And you're hardly old enough to be so confident to walk up to a strange man at a bar."

She laughed and tilted her head, "You planning on doing something bad to me, Harry?"

And that. That pulled a reaction out of him that spread over his features slowly as he shook his head in disbelief, "Darlin', you wouldn't be able to handle me."

Her eyes widened slightly. Now she was definitely not giving up. Y/n wasn't one to fail and Harry might be making her work hard for it but she couldn't imagine it wouldn't be worth it in the end.

"Is that a challenge or something?" She softly scraped her nail over his tattooed wrist and Harry watched her red nail work over his skin.

His resolve was fading fast. She could tell he wasn't going to keep denying her. And why should he? If he was single, which he appeared to be, what was the harm in having a little fun with someone younger? Y/n didn't mind. And he certainly shouldn't either.

"If it were a challenge you'd know it. Lots of other guys here, Y/n. Go enjoy your night with someone closer to your own age."

She sighed in annoyance. But he hadn't moved his arm away from her and she was going to take that as a sign.

Dragging the toe of her shoe into his shin she grinned, "I don't want to enjoy my night with someone my own age. Not tonight anyway. I think you've convinced me that I need to test out this theory of yours. That you think I can't handle you. Cause I bet I can."

With his eyes piercing into hers, he took another sip of his drink. She thought she might have just convinced him to give her a smile at the very least because it looked like he was weighing his options. And if she could get him to smile she might have luck with the rest.

He tilted his chin upward for a moment, eyes aimed at the ceiling like he was calling on a higher power for strength, "Go back to your friends, Y/n. Any other man here would love to have your company."

"But you wouldn't love to have my company?"

"I mean… I'm still here," the other man raised his hand and leaned into Harry, "Honey we could have so much fun. Any man who'd turn you down is either battin' for the other team or more likely," he chuckled and pushed his shoulder into Harry's teasingly, "He can't get it up anymore."

Y/n's mouth dropped open at that and Harry turned to look at the man. She wished she could see the look on his face, "Sit the fuck back down, John. She already told you she's not interested in you."

"Yeah, and you're not interested in her so what's it matter to you? Look at her, Harry. Practically begging you. Young and bubbly… Tight—"

Harry's hand covered John's throat as he pushed him away, nearly making his stool topple over, "Get the fuck outta here. You had too much whisky tonight."

"Aww… come on Harry… I was just jokin'!"

She watched as he stood from his stool and looked down at John, "And you thought that was funny? You like making jokes about women like that?"

The man put his hands up in surrender, "I'm out. Here…" he threw a wad of cash on the bar top before he moved past Harry and then looked at Y/n, "My apologies if I offended you."

They watched as John left the bar quickly and then Harry sat back down before he waved at the bartender and signaled for the check, "Just the one whisky neat."

"You're leaving already? Night's still young, Harry."

He sucked at his teeth as he scraped his gaze over her face and down to her cleavage. She smiled when she watched the path his eyes had taken.

The bartender handed him the bill and Harry leaned over to pull his wallet from his back pocket.

She scooted closer to him, "You headed home?"

He nodded, but not necessarily in answer to her question, it was more of an appraisal kind of nod. He was still silent as he pulled cash out of his wallet.

"Thanks for that, by the way. I'm sure John's a nice guy and all but he's not really my type. And I'm sure he was wrong about you."

That got his attention. Harry flicked his gaze back to hers, "Wrong about me?"

She smiled, "The part where he said you couldn't get it up. You're not that old. I'm sure you still can. Right?"

He clenched his jaw and breathed out of his nostrils like he couldn't believe she'd asked him such a thing. He handed the bartender his cash with a nod before he stood up from his stool.

"Huh. Since you're so quiet about it maybe he was right," she goaded, pressing her lips together to flatten her smile as she looked up at him through her lashes.

Harry placed a palm down on the bar top next to her hand and leaned over her, "You're out of your depth here, Y/n."

"Now, you don't really know that do you? Just because I'm younger than you doesn't mean I don't know what I'm doing."

"You're awfully pushy. Not used to hearing no, are you?"

Y/n watched as the edge of his mouth lifted in amusement and she widened her eyes and pointed, "You're almost smiling."

He shook his head and looked around the bar before pinning his gaze back to hers, "I hope you enjoy the rest of your night. But your luck has run out with me, princess."

Harry stood to his full height and Y/n decided to try one last time, "So it's true then. What he said."

He stopped and turned to look back at her, a slow burning heat behind his gaze, "Couldn't be further from the truth."

She smiled and slid off her stool to stand in front of him. His height was impressive, "Prove it."

The line of his jaw hardened, turning his cheekbones into slashes of tension. His eyes simmered as he weighed his options. Finally, a hint of a smile stretched over his mouth. A small one, but still.

"I don't need to prove anything to silly little girls."

"Good thing I'm not a silly little girl. I'm a grown woman, Harry."

Y/n knew she was pushing it. She'd never needed to throw herself at any man before. But because of that, she wasn't used to rejection either. Maybe it was a good lesson for her ego. She knew her big fault was how entitled she could act sometimes. But that was partly thanks to how she was raised. It's better to act like a man to get what you want in life, her dad told her. And so far, that had been true. Some women balked at her confidence and her bold attitude. She wasn't demure or sweet enough. And men would often refer to her as a bitch or say that she was trying too hard.

She'd work on her ego another time. But right now? She was focused on winning this battle.

"What do you want with someone like me anyway? Hm? I'm old, Y/n. What's in it for you?"

Blinking her eyes she shook her head, "You're not old, first of all. Secondly, you're really attractive. It doesn't need to go much deeper than that, does it? I just think you're handsome. And I do kind of like a challenge."

"I can see that you like a challenge. It's the only reason I haven't walked out that door yet. Kind of relentless."

She smiled, "So it's working?"

Another half-smile worked its way up his mouth as he laughed in disbelief, "Are you surprised that it is?"

His pupils coasted over her figure and then back up to her face. The warmth of his gaze singed her skin like an open flame.

"I guess I just didn't know how difficult it'd be with you."

He licked his lips, "Difficult. You have no idea. But looks like you're about to find out. Go tell your friends what's going on. Meet me out front."

Y/n watched him turn and walk away. She was shocked. For a minute she thought he wasn't going to go for it at all.

Shaking off the sudden surprise of having gotten to him she settled up with the bartender and then stopped at the table with her friends. They were just about to give her condolences for having oversold her ability but she interrupted. "He's waiting for me outside. Location is on. Don't wait up!"

Harry was leaning against a black car in the parking lot when she stepped out of the doors. The moment he saw her he pushed himself off the car and opened the passenger door for her.

It was going to be tricky to maintain the kind of confidence she'd been feigning with him up until then but there was no part of her that didn't want to find out what he could show her.

She watched as Harry sat down in the driver's seat and started up his car. He took up too much space in the seat. His big hand wrapped around the leather steering wheel while his other encased the shift stick. Even the way he drove was turning her on.

She was pleased that she'd wormed her way under his skin and that he'd given in. She'd try her best to make it worth his while. Reaching across the console she put her hand on his thigh and he glanced down quickly before setting his gaze back on the road.

Now, Harry had slept with younger women a couple of times. He generally preferred someone closer to his age because he liked the confidence and experience that came with age. Women in their 20s were often in a different stage of life and that was fine –normal even, but it just usually wasn't a match for him. Not sexually and not mentally.

But Y/n was unusually confident for being so young. Persistent. He liked it, he couldn't lie. Whether or not she really had much else going for her beyond confidence, he guessed he'd find out. Well, she was very cute too. She did have that in her favor.

And Y/n at least seemed like she knew what she wanted. It was flattering as well. Being approached by such a pretty young thing. He figured the moment he told her to go back to her friends she'd give up but she was just fiery enough that she wasn't deterred.

When she ran her nail over his wrist he knew he was screwed. She was just close enough that he could smell her perfume and then she nudged her shoe into his shin and all he could think about was that she really wanted to be shown a good time and if anyone could it was him.

Harry knew his way around a woman's body. They were all different and he liked finding all the buttons and things that made them purr. In his experience, though, the younger the woman, the less she knew her own body. He didn't know if Y/n was just talking a big game but he was about to find out.

He stayed quiet as she ran her hand down his thigh and he shifted as the car accelerated past the green light. He'd see if she'd do anything with her hand but maybe she'd just pet at him like a novelty toy. He didn't expect—

"This is okay?" She asked him, her tone sultry as she palmed at his crotch.

He licked his lips, "Have at it."

His cock fattened up nicely with not much effort on her part. Proof that he definitely could get it up. Plucking at his button she looked from his face to her fingers as she leaned further over the console to reach her hand into his open pants to help him with the awkward angle of his dick. He seemed to appreciate that as he shifted under her palm.

Rubbing over his heather grey briefs she peeled down the elastic band the slightest to get a peek. The dark shade of pink on his tip matched the muted raspberry of his lips. She slid the pad of her middle finger over the slit and he softly inhaled through his teeth.

She wouldn't be able to give him roadhead like she wanted. It was impossible with the stick shift in the way. But she could wrap her fingers around his shaft and feel him under her palm until they got wherever they were going.

"Mmm… It's so big, Harry. Knew you would be. Might be the biggest I've seen in person. Can't tell yet, though. Have to wait to see when we've got these off."

Harry pushed a laughed breath through his nose. She was a bold thing. Her assertiveness was a turn-on. He didn't like meek and shy. Not when it came to sex.

When she spit into her palm and smeared it down his length, the best she could, he parted his lips and stepped on the gas. She was already exceeding any expectations he had for her. Maybe she'd prove him wrong.

Her nail scraped the underside of him and she moaned, "Really want it in my mouth."

He gulped harshly and ticked his jaw, "Just be patient. I'll let you put it in your mouth soon enough."

"And where are we going? Your place?"

He nodded, "Just a few minutes away."

She squeezed around him and pulled upward slowly. She knew already, he was well above average and she was going to have to work to give him a proper blowy.

His house was a one story, the driveway at the front with a garage attached. He lifted his hand and pushed on a device that was clinging to his sun visor and the garage door began to open. There was a covered motorcycle along the back wall and then the garage door closed after he shut off the engine.

She moved her hand away and unbuckled herself as he got out. When she reached down to pick up her little purse she realized her panties were already wet. She grinned as she stepped out, adjusting her dress before closing the door, and then followed behind him as he led her into a dark hallway.

When he turned on the lights she took it all in. Hardwood floors led into a dining area and then a kitchen. Hung on the walls were photos of himself with two children and then more framed photos with just the kids.

"Do you have kids?"

"I do. Boy and a girl. 7 and 10."

"You're not married are you?"

He laughed, "If I were you'd have known. Wouldn't have been out in the first place if I had a wife waiting for me at home."

She nodded as he turned on the kitchen light and pulled out two glasses before filling them with water.

"Divorced?"

Handing her a glass he squinted, "Yes."

She took a sip. He was a man of few words she'd gathered. She looked around the kitchen. Wood cabinets, an outdated laminate countertop, stainless steel appliances. The space could use some updating but it was large and he had a big pantry.

Sitting the glass down on the counter she watched him closely. His pants were still unbuttoned. She eyed the space at his crotch as he placed his own glass down next to hers.

"It's not gonna suck itself."

She laughed and looked up at him. He had a genuine smile on his face that time. The first real smile she'd seen from him all night. A healthy row of clean teeth, a dimple…

"Hmm… I think you're right. Let's see what we've got…"

She moved in front of him and placed her hands on his pants to push them away but before she could inch them down he wrapped his meaty hand around the back of her neck and drew her into his chest. His mouth was warm and soft. His tongue tasted like the whisky he'd been drinking.

Letting go of his pants she held onto his biceps as he used his free hand to push her hips against his. Still nice and hard. He ran his tongue over her lips and she moaned into his mouth. He worked his warm lips down to her jaw and then he licked upward on her neck, the wet patch was cool on her skin from the air in the kitchen. He did it again and her knees almost gave out. She hadn't been licked like that before.

He kissed over her clavicle and then drew his tongue over her flesh. Her heart was thrumming quickly and she squeezed his strong arms when he rutted against her.

"You good at sucking cock, Y/n?" He pushed his nose against her jawline and the hot breath from his words scattered over the skin on her neck.

"I want to be," she spoke breathlessly, eyes fluttering closed as he mawed at her throat.

He parted from her neck and looked down at her, half-lidded gaze and spit-slicked lips, "Go on."

Instantly she dropped to her knees as her fingers worked deftly at pulling his pants down and then his underwear. She'd sucked a handful of dicks so she knew a couple of moves.

Getting her hand around his thick shaft proved to be a small challenge. To say he was thick… understatement. Long too. His tip was smooth, mushroomed with ridges along the length that she hoped she'd get to feel later on. His was the kind of cock that women dreamed of.

Looking up at him she licked her palm and used her spit to pump him slowly. Another glob over his tip for good measure. Then she pressed a kiss to the base of him, just over his sac, and screwed her eyes upward to watch his expression as she licked his balls, one side at a time. She wound her tongue all around to wet him before sucking at one side, pulling it into her mouth and he let out a ragged breath, his dark pupils spreading inky until the soft green had almost vanished.

He liked it.

She worked around the other side, sucking him in again and swirling her tongue softly underneath the tender bits. He gripped the counter behind himself.

Pulling off she straightened her back and licked upward, feeling every delicious thick ridge along his shaft until her tongue met his smooth crown. Laving every crevice of his tip, she dipped her tongue into his slit and then ran it under the frenulum before she wetted every inch of his glans.

Her mouth was watering when she parted her lips around him and flitted her gaze upward. He was watching her with a slack jaw as she took him a little deeper. He cradled the back of her head and moaned.

"Just suck the tip…."

She blinked up at him and pulled her lips just over the lip, swirling and suckling around him like he wanted.

"Fuck. Just like that." His hand at the back of her head was easy. He didn't push or pull. It was more like a pleased gesture as his fingertips flexed around her skull gently.

Y/n would have liked to have gone deeper. Wanted to show him her best work. But he seemed rather happy with what she was doing.

She bobbed a couple of times, only to slide her lips back to his tip. Her pace was slow when she began to stroke his length with a little twisting motion.

He was big. She knew she could take more but in a way, she was grateful that that was all he was asking for.

A groan fell from his chest and he bucked forward, his cock slipping down her tongue and she sucked, drawing more of him in as she moved her hands away.

"Goddamnit, you're good."

She took that as permission to go deeper. Relaxing her jaw she closed her eyes and held her breath, pushing down to her limit. She filled her throat with his cock the best she could and gurgled around his tip.

He coughed out a moan and then thumbed at her cheek, "Alright, that's good."

She pulled off of him. His heavy cock aimed right at her face when she sat back on her knees and looked up at him, "I can do better than that."

He laughed and put his hand out for her to take, helping her stand up, "I bet you can. Come on."

Harry kept her hand in his as he led her to his bedroom. It was just past the dark living space and he turned on a floor lamp on the opposite side of the room from the bed. When he turned back toward her he cupped her face and kissed her again.

She pressed her hand into his warm, hard chest and he reached around the back of her dress to pull the zipper downward, his fingers dragging down her skin as he went. His touch sent a tremor down her spine as continued kissing her wetly.

He stepped back, helping her out of her dress until it fell to the floor. His eyes raked over her body and he smoothed his hands over her hips and up to her bra-covered breasts. He stepped in closer, walking her backward toward his bed. He put his hands back on her hips and nudged her to sit before he reached down to lift her leg up by her calf, removing her heels, one at a time.

Y/n's thong was drenched. She stared at him while he placed her shoes side by side at the foot of the bed and then he placed his big palms on her thighs, pushing her legs open, "Lie back."

She let her back hit the mattress as Harry got to his knees on the floor. An arm reached under her thigh as he spread her apart and then she felt her panties being pulled at until her her wet pusslips were right in his face. He groaned and felt a hand slide up the inside of her thigh. He pressed his mouth over her mons and looked up at her before he opened his mouth wide and drew his tongue through her crease making her gasp.

"Get your bra off."

She pushed herself up slightly and worked at the clasp of her bra between moans as Harry continued licking at her pussy. When she pulled her arm through the flimsy material he lifted his head and reached around her back, pulling her closer to the edge of the bed and he sucked a nipple into his mouth.

"Oh, fuck!"

Y/n's finger and her long nails pushed into Harry's hair and scraped at his scalp as he licked and pulled at each nipple. He buried his face between her tits and let out a low sound, like he was murmuring something to her but only her breasts were allowed to hear it.

When he sunk back down he pushed at her so she'd lie back and he started in on her clit, one hand holding her panties to the side as he devoured her glistening cunt.

She kept feeling like she was going to slide off the edge of the bed but Harry's grip on her kept her still. His tongue and his lips were magic as he drew her to her end. She yanked at his hair and babbled his name on repeat as her spine bowed off the bed when she came.

Her chest was still rising and falling heavy when she felt her body being pushed upward. She popped her eyes open and watched him roll a condom over his shaft before he kneed back up onto the bed next to her. He was stark naked. His body was insane. Thick muscle and masculine everything. Tattoos scatter over his arms and chest.

Fuck, she muttered under her breath.

"Flip over, for me," his deep voice was husky as he motioned toward her to move.

She rolled to her stomach and she felt his fingers slide between the band of her panties and her hips as he pulled them down her legs.

"Ass up a little. I want to see all of you, Y/n."

She grinned and turned to look at him over her shoulder as she lifted her hips and spread her thighs. His lips were parted as he grabbed her ass and squeezed, making her cheeks spread apart. He inhaled sharply through his teeth and then dipped in, kissing her pussy from behind before licking upward over her ass.

She squealed quietly and bit her lip, still watching him behind her as he lifted, a lopsided grin on his face. He gazed at her as he fisted the base of his cock and slid the head up and down her soaked folds before he tipped his hips to push in just the tip.

"Gorgeous. Gonna look even better wrapped around cock. You like anal?"

"Never tried it."

He licked his lips and pressed his lips together as he looked at the spot where his dick was pressed against her cunt, "Figured. S'alright. Pussy's my favorite anyway."

"We could try… if you want."

He looked back into her eyes, a cocky smile on his face, "Your little hole would need to be trained. And that takes time. So, there will be no anal tonight. Not gonna try and hurt you. But that's a cute thought."

He canted his hips inward, eyes on hers and her mouth dropped open when she felt her entrance splitting open for him. She was tight, but so slick, it only took a few slow thrusts until he was buried in with a low grunt. He pulled back and then pushed his entire length into the hilt.

"Fuck—fuck!" She cried and stuffed her face into the blankets.

"Too much?"

"No! It's so good. You're just so big…" She began to send her hips back against him and Harry slowly fucked in to match her pace. His eyes were everywhere. On her puss getting split open on his cock, the curve of her lower back, the swell of her ass.

He just knew she'd look so sweet with her ass stuffed too, but good things like that couldn't be rushed which was a shame.

Every thrust was gushy wet. Y/n bubbled out small moans every time his dick brushed deep into her guts. It was better than she imagined. The way he filled her to the brim was going to turn into an addiction. She'd never slept with any man that had her wanting seconds before they'd even finished.

"Oh my god…" she mewled into the comforter.

"Fuck, I know, baby…"

She fit him like a glove, it was perfect. He went in a little faster, balls thudding against her skin rhythmically making her bounce forward as she spread around his girth. When he ground in she arched her back deeply and let out a soft groan, her hands fisted at the blanket and Harry reached around and smeared his fingertips over her clit.

It had her panting and pushing into him feverishly. She'd needed the friction on her throbbing button and he'd found it easily, thick, rough fingerprints slicking back and forth as he rutted in and in. It sent electrical sparks over her limbs.

"Like that? Needs her clit touched? Shit baby, act like you've never been touched by a man right here before…" he plucked at her like he was playing the guitar and she began to fade, her moans getting caught in her chest.

He could feel her walls tightening around him as he drove in deep.

"Fuck, Harry— fuck!"

He grinned as he watched her shudder, "Give it up, Y/n. There you go…"

She began to pulse around him, a constant stream of nonsense falling from her lips as he stroked against her channel and pushed deep into her tummy, his fingers still working her clit with ease.

Just as her body had tipped and oxygen returned to her lungs he pulled out and she felt him taking her hips and turning her around to her back. Harry grabbed her ankles and lifted until each was settled over his shoulders and pushed back inside of her, cock drilling down to her core making her teeth chatter at the way he split her down the middle.

Harry leaned over her, cock buried deep as she watched her pretty face twist up with pleasure. Plapping into her, her tits wobbled as his balls tightened against his body. The harder he plunged in, the more her legs shook. Soon, her ankles had slipped down and her feet hit the mattress as he continued drilling into her. His face was flushed hot, lips parted, muscles tensed.

Reaching up to his neck she smoothed her fingers over his warm skin and he lowered his chest down to hers and kissed her. That filthy tongue ran over her lips and he sloppily sipped at her between sucking at her lips. Her brain had turned to jelly.

She felt his hand on her outer thigh squeezing and brushing as he fucked down into her. "Mmm… fuck, Y/n, m'gonna come…"

He trembled over her, thick thighs pressed down and flexed as he rutted in and in and in, and then… he stilled. A deep, guttural moan vibrated through his chest down into hers.

She sighed when she felt him throbbing, pumping into his condom. Her fingers caressed the muscles over his back and she gasped when he bucked in harshly, once more as he emptied the last of his come into the rubber wrapped around his cock.

He slowed his kisses until they were lazy little pecks and then he looked down at her, his chest heaving. She was already grinning up at him.

"What?"

She blinked her eyes, "That was fun."

He puffed out a breath, "I guess that's a good way to describe it."

Harry was a gentleman as he pulled out slowly and helped her off the bed and led her to his bathroom. He helped her clean up and listened to her tell him about her job —just reminding him that she was an adult after he commented on her being so young again.

When she picked her dress up off the floor and started to step into it, Harry frowned, "What are you doing?"

She stopped and raised her brows. "Getting dressed. Was gonna call an Uber. I'm sure you don't want a stranger in your house all night," she laughed.

Harry pulled at her hand, making her drop her dress, "What kind of men have you been hanging out with that let you leave in an Uber at 2 am? You'll stay here."

She opened her mouth and then closed it in surprise before tilting her head in confusion, "Really? I just assumed—"

"You'll stay the night here. There's no way in hell you're getting an Uber at this time of night. It's dangerous."

She grinned and shrugged, "Well then… can I have a shirt or something to sleep in?"

He placed his warm hands on her hips, "You can have a t-shirt if you like. I prefer to sleep naked myself."

"Oh yeah? I usually do too as a matter of fact."

He held her out in his arms and eyed her naked frame, "Looks like we're both good to go then. We'll get you sorted in the morning. I'll give you a ride home then."

"I think you just want to keep me here with you," she chuckled.

Harry shook his head and released her hips before he popped her on the bottom with his palm. She bleated out a laugh.

"Get your ass in bed before I change my mind."

"Yes, sir."

. .

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DILF | older!harry

MAIN MASTERLIST

Summary: Y/n meets an older man at a bar and she's not taking no for an answer. Harry likes her persistence.

A/N: This was requested + this! Also, please think before you judge Y/n. She is very bold and confident in this. Maybe even a little pushy but Harry likes it (even if at first he doesn't give that impression). Also he's single so this isn't cheatrry!

Word Count: 6,580

Warning: age gap, smut, alcohol consumption (light)

. .

"That one. Total dilf. He looks grumpy. Bet you can't crack him."

Y/n laughed at her friend and looked down at her red-painted nails before narrowing her gaze on the attractive older man who was seated at the corner of the bar alone. He was nursing a whisky and he did look rather sullen. Unapproachable even.

"Why him?"

"Because he's hot. And I'm curious to see if you can get him to smile at least," Warren raised her brows, "I dare you."

Y/n tilted her head and assessed him. He was nice and big, taking up a decent amount of space at the bar, broad shoulders and back hunched as he leaned his muscular forearms on the wood of the bar top. Meaty hands placed on either side of his lowball glass. Thick brown waves on top of his head with a bit of silver coming in at the temples. But the handsome features on his face really set him apart. His granite jawline gave way to stubble that stretched over his skin and shaded in the spaces around his pink lips.

If she could "crack" him she wasn't sure she'd want just a smile. He looked yummy enough to eat.

Drinking down the last of her martini she pointed at Warren and then Tara, "Fine. Give me twenty minutes and I'll have him eating from the palm of my hand."

Tara laughed, "If you say so…"

She placed her heeled feet down on the floor and brushed her hands over her dress, "Oh, I do say so. Just watch and learn, ladies."

Y/n wasn't quite that confident, but she wasn't about to say no to dare. And she could hold her own when it came to flirting. She liked getting a little attention and if she could garner this one's interest it might be fun.

She sauntered up to the bar behind the man and noticed the way his t-shirt stretched over his lats and tapered loosely down at his waist. The guy was fit. And lucky her, there was an open stool next to him.

Sliding onto the seat she waved at the bartender to order another drink. She'd need all the courage she could get, in whatever form she could get it.

Tapping her long nails on the lacquered wood she felt nerves thrumming through veins before turning toward the man finally. He hadn't seemed to take note of her yet, which honestly was unusual in most cases. Maybe she thought too highly of herself but men tended to notice her right away. She appreciated the challenge, though.

Reaching her hand into his space to greet him, she pushed down her nerves to sound steady as she spoke, "I'm Y/n."

She watched his brow furrow as he turned to look at her hand and then up at her eyes, his expression, which she expected would soften once he looked at her, was unamused. A single light overhead lit the tops of their heads as a shadow cast over the side of his face and he didn't make a move to shake her hand, "And I'm old enough to be your dad."

A surprised scoff fell from her lips as she moved her hand away from him. She wiggled in her seat and crossed her leg over her thigh toward him, gulping down the initial rejection with as much grace as she could muster, "I think you're jumping to conclusions about my intentions. But so what if you're older than me? I don't mind. We're both adults, right?"

An unimpressed grunt rumbled from his throat before he took another sip of his whisky and he looked away from her toward the TV that hung not far away from where they sat.

The bartender placed her olive martini down on the bar in front of her, "It'll be on Y/n Y/l/n. I already have an open tab."

A sip of the salty drink felt warm down her throat. So he was going to be a bit tough to crack. She turned to look at her friends who were grinning in her direction.

Straightening her back to feel more confident she tried again, "So you're not gonna tell me your name even?"

Without looking at her, he licked his lips and ticked his jaw, "Y/n, I think it's past your bedtime."

She smiled at that. He'd said her name, which meant he'd been listening, "My bedtime is whenever I say it is, not when some grouchy stranger says."

He puffed out an amused laugh through his nose, "I am a stranger. Which means you should be cautious, little girl. Your dad didn't teach you about things like that?" He turned to look down at her again, and that time she saw the soft green color of his eyes as the light hit his face just right.

But now she was really determined. She smiled brightly at him and let her eyes coast over his tattooed arm and then back up to his face, "Are you telling me you're dangerous?"

He still didn't smile as he shook his head like he was surprised by her gall, "Do your parents know what you're up to tonight?"

"I'm 24. Graduated from college, live on my own, pay my bills, have a full-time job. You seem to be awfully worried about my parents. I can take care of myself just fine."

Just then another person sat down next to the man Y/n was trying to whittle away at. He poked his elbow at him, "Who's this?"

"Don't know. Someone who's about to go back to her table with her little girlfriends."

Biting her lip she traced the rim of her martini glass with her fingertip, keeping her eyes set on the handsome tattooed one, "Not even a smile. Just one? Please?"

"Like I already said, I'm way too old for you."

The other man leaned over and reached to tap Y/n's shoulder, "Hey. Forget about Harry, here. You can bring me home with you if you're looking for a daddy tonight."

She frowned and looked him up and down to asses. He was late 40s perhaps, wearing a local band t-shirt, ripped jeans, and a backward cap to make himself appear a little more youthful. "No thanks. You'd know if I was interested in you."

Harry bit the inside of his cheek to stop himself from smiling at her retort. She was definitely too young but he liked her spunk.

"Now, Harry…" she said his name slowly as she leaned a little closer, "I've got your name thanks to your friend. Can I have a smile?"

"Why?" He stared down at her, the caress of his gaze felt infinite and she found her skin convecting in its wake. He might be hard to crack but this one would be worth it, she determined.

She sighed and slid her finger dangerously close to his wrist as he looked down at her nail and watched her trail it near his arm, "I just hoped to see you smile is all. Too handsome to have such a sour scowl on your face."

"And you're hardly old enough to be so confident to walk up to a strange man at a bar."

She laughed and tilted her head, "You planning on doing something bad to me, Harry?"

And that. That pulled a reaction out of him that spread over his features slowly as he shook his head in disbelief, "Darlin', you wouldn't be able to handle me."

Her eyes widened slightly. Now she was definitely not giving up. Y/n wasn't one to fail and Harry might be making her work hard for it but she couldn't imagine it wouldn't be worth it in the end.

"Is that a challenge or something?" She softly scraped her nail over his tattooed wrist and Harry watched her red nail work over his skin.

His resolve was fading fast. She could tell he wasn't going to keep denying her. And why should he? If he was single, which he appeared to be, what was the harm in having a little fun with someone younger? Y/n didn't mind. And he certainly shouldn't either.

"If it were a challenge you'd know it. Lots of other guys here, Y/n. Go enjoy your night with someone closer to your own age."

She sighed in annoyance. But he hadn't moved his arm away from her and she was going to take that as a sign.

Dragging the toe of her shoe into his shin she grinned, "I don't want to enjoy my night with someone my own age. Not tonight anyway. I think you've convinced me that I need to test out this theory of yours. That you think I can't handle you. Cause I bet I can."

With his eyes piercing into hers, he took another sip of his drink. She thought she might have just convinced him to give her a smile at the very least because it looked like he was weighing his options. And if she could get him to smile she might have luck with the rest.

He tilted his chin upward for a moment, eyes aimed at the ceiling like he was calling on a higher power for strength, "Go back to your friends, Y/n. Any other man here would love to have your company."

"But you wouldn't love to have my company?"

"I mean… I'm still here," the other man raised his hand and leaned into Harry, "Honey we could have so much fun. Any man who'd turn you down is either battin' for the other team or more likely," he chuckled and pushed his shoulder into Harry's teasingly, "He can't get it up anymore."

Y/n's mouth dropped open at that and Harry turned to look at the man. She wished she could see the look on his face, "Sit the fuck back down, John. She already told you she's not interested in you."

"Yeah, and you're not interested in her so what's it matter to you? Look at her, Harry. Practically begging you. Young and bubbly… Tight—"

Harry's hand covered John's throat as he pushed him away, nearly making his stool topple over, "Get the fuck outta here. You had too much whisky tonight."

"Aww… come on Harry… I was just jokin'!"

She watched as he stood from his stool and looked down at John, "And you thought that was funny? You like making jokes about women like that?"

The man put his hands up in surrender, "I'm out. Here…" he threw a wad of cash on the bar top before he moved past Harry and then looked at Y/n, "My apologies if I offended you."

They watched as John left the bar quickly and then Harry sat back down before he waved at the bartender and signaled for the check, "Just the one whisky neat."

"You're leaving already? Night's still young, Harry."

He sucked at his teeth as he scraped his gaze over her face and down to her cleavage. She smiled when she watched the path his eyes had taken.

The bartender handed him the bill and Harry leaned over to pull his wallet from his back pocket.

She scooted closer to him, "You headed home?"

He nodded, but not necessarily in answer to her question, it was more of an appraisal kind of nod. He was still silent as he pulled cash out of his wallet.

"Thanks for that, by the way. I'm sure John's a nice guy and all but he's not really my type. And I'm sure he was wrong about you."

That got his attention. Harry flicked his gaze back to hers, "Wrong about me?"

She smiled, "The part where he said you couldn't get it up. You're not that old. I'm sure you still can. Right?"

He clenched his jaw and breathed out of his nostrils like he couldn't believe she'd asked him such a thing. He handed the bartender his cash with a nod before he stood up from his stool.

"Huh. Since you're so quiet about it maybe he was right," she goaded, pressing her lips together to flatten her smile as she looked up at him through her lashes.

Harry placed a palm down on the bar top next to her hand and leaned over her, "You're out of your depth here, Y/n."

"Now, you don't really know that do you? Just because I'm younger than you doesn't mean I don't know what I'm doing."

"You're awfully pushy. Not used to hearing no, are you?"

Y/n watched as the edge of his mouth lifted in amusement and she widened her eyes and pointed, "You're almost smiling."

He shook his head and looked around the bar before pinning his gaze back to hers, "I hope you enjoy the rest of your night. But your luck has run out with me, princess."

Harry stood to his full height and Y/n decided to try one last time, "So it's true then. What he said."

He stopped and turned to look back at her, a slow burning heat behind his gaze, "Couldn't be further from the truth."

She smiled and slid off her stool to stand in front of him. His height was impressive, "Prove it."

The line of his jaw hardened, turning his cheekbones into slashes of tension. His eyes simmered as he weighed his options. Finally, a hint of a smile stretched over his mouth. A small one, but still.

"I don't need to prove anything to silly little girls."

"Good thing I'm not a silly little girl. I'm a grown woman, Harry."

Y/n knew she was pushing it. She'd never needed to throw herself at any man before. But because of that, she wasn't used to rejection either. Maybe it was a good lesson for her ego. She knew her big fault was how entitled she could act sometimes. But that was partly thanks to how she was raised. It's better to act like a man to get what you want in life, her dad told her. And so far, that had been true. Some women balked at her confidence and her bold attitude. She wasn't demure or sweet enough. And men would often refer to her as a bitch or say that she was trying too hard.

She'd work on her ego another time. But right now? She was focused on winning this battle.

"What do you want with someone like me anyway? Hm? I'm old, Y/n. What's in it for you?"

Blinking her eyes she shook her head, "You're not old, first of all. Secondly, you're really attractive. It doesn't need to go much deeper than that, does it? I just think you're handsome. And I do kind of like a challenge."

"I can see that you like a challenge. It's the only reason I haven't walked out that door yet. Kind of relentless."

She smiled, "So it's working?"

Another half-smile worked its way up his mouth as he laughed in disbelief, "Are you surprised that it is?"

His pupils coasted over her figure and then back up to her face. The warmth of his gaze singed her skin like an open flame.

"I guess I just didn't know how difficult it'd be with you."

He licked his lips, "Difficult. You have no idea. But looks like you're about to find out. Go tell your friends what's going on. Meet me out front."

Y/n watched him turn and walk away. She was shocked. For a minute she thought he wasn't going to go for it at all.

Shaking off the sudden surprise of having gotten to him she settled up with the bartender and then stopped at the table with her friends. They were just about to give her condolences for having oversold her ability but she interrupted. "He's waiting for me outside. Location is on. Don't wait up!"

Harry was leaning against a black car in the parking lot when she stepped out of the doors. The moment he saw her he pushed himself off the car and opened the passenger door for her.

It was going to be tricky to maintain the kind of confidence she'd been feigning with him up until then but there was no part of her that didn't want to find out what he could show her.

She watched as Harry sat down in the driver's seat and started up his car. He took up too much space in the seat. His big hand wrapped around the leather steering wheel while his other encased the shift stick. Even the way he drove was turning her on.

She was pleased that she'd wormed her way under his skin and that he'd given in. She'd try her best to make it worth his while. Reaching across the console she put her hand on his thigh and he glanced down quickly before setting his gaze back on the road.

Now, Harry had slept with younger women a couple of times. He generally preferred someone closer to his age because he liked the confidence and experience that came with age. Women in their 20s were often in a different stage of life and that was fine –normal even, but it just usually wasn't a match for him. Not sexually and not mentally.

But Y/n was unusually confident for being so young. Persistent. He liked it, he couldn't lie. Whether or not she really had much else going for her beyond confidence, he guessed he'd find out. Well, she was very cute too. She did have that in her favor.

And Y/n at least seemed like she knew what she wanted. It was flattering as well. Being approached by such a pretty young thing. He figured the moment he told her to go back to her friends she'd give up but she was just fiery enough that she wasn't deterred.

When she ran her nail over his wrist he knew he was screwed. She was just close enough that he could smell her perfume and then she nudged her shoe into his shin and all he could think about was that she really wanted to be shown a good time and if anyone could it was him.

Harry knew his way around a woman's body. They were all different and he liked finding all the buttons and things that made them purr. In his experience, though, the younger the woman, the less she knew her own body. He didn't know if Y/n was just talking a big game but he was about to find out.

He stayed quiet as she ran her hand down his thigh and he shifted as the car accelerated past the green light. He'd see if she'd do anything with her hand but maybe she'd just pet at him like a novelty toy. He didn't expect—

"This is okay?" She asked him, her tone sultry as she palmed at his crotch.

He licked his lips, "Have at it."

His cock fattened up nicely with not much effort on her part. Proof that he definitely could get it up. Plucking at his button she looked from his face to her fingers as she leaned further over the console to reach her hand into his open pants to help him with the awkward angle of his dick. He seemed to appreciate that as he shifted under her palm.

Rubbing over his heather grey briefs she peeled down the elastic band the slightest to get a peek. The dark shade of pink on his tip matched the muted raspberry of his lips. She slid the pad of her middle finger over the slit and he softly inhaled through his teeth.

She wouldn't be able to give him roadhead like she wanted. It was impossible with the stick shift in the way. But she could wrap her fingers around his shaft and feel him under her palm until they got wherever they were going.

"Mmm… It's so big, Harry. Knew you would be. Might be the biggest I've seen in person. Can't tell yet, though. Have to wait to see when we've got these off."

Harry pushed a laughed breath through his nose. She was a bold thing. Her assertiveness was a turn-on. He didn't like meek and shy. Not when it came to sex.

When she spit into her palm and smeared it down his length, the best she could, he parted his lips and stepped on the gas. She was already exceeding any expectations he had for her. Maybe she'd prove him wrong.

Her nail scraped the underside of him and she moaned, "Really want it in my mouth."

He gulped harshly and ticked his jaw, "Just be patient. I'll let you put it in your mouth soon enough."

"And where are we going? Your place?"

He nodded, "Just a few minutes away."

She squeezed around him and pulled upward slowly. She knew already, he was well above average and she was going to have to work to give him a proper blowy.

His house was a one story, the driveway at the front with a garage attached. He lifted his hand and pushed on a device that was clinging to his sun visor and the garage door began to open. There was a covered motorcycle along the back wall and then the garage door closed after he shut off the engine.

She moved her hand away and unbuckled herself as he got out. When she reached down to pick up her little purse she realized her panties were already wet. She grinned as she stepped out, adjusting her dress before closing the door, and then followed behind him as he led her into a dark hallway.

When he turned on the lights she took it all in. Hardwood floors led into a dining area and then a kitchen. Hung on the walls were photos of himself with two children and then more framed photos with just the kids.

"Do you have kids?"

"I do. Boy and a girl. 7 and 10."

"You're not married are you?"

He laughed, "If I were you'd have known. Wouldn't have been out in the first place if I had a wife waiting for me at home."

She nodded as he turned on the kitchen light and pulled out two glasses before filling them with water.

"Divorced?"

Handing her a glass he squinted, "Yes."

She took a sip. He was a man of few words she'd gathered. She looked around the kitchen. Wood cabinets, an outdated laminate countertop, stainless steel appliances. The space could use some updating but it was large and he had a big pantry.

Sitting the glass down on the counter she watched him closely. His pants were still unbuttoned. She eyed the space at his crotch as he placed his own glass down next to hers.

"It's not gonna suck itself."

She laughed and looked up at him. He had a genuine smile on his face that time. The first real smile she'd seen from him all night. A healthy row of clean teeth, a dimple…

"Hmm… I think you're right. Let's see what we've got…"

She moved in front of him and placed her hands on his pants to push them away but before she could inch them down he wrapped his meaty hand around the back of her neck and drew her into his chest. His mouth was warm and soft. His tongue tasted like the whisky he'd been drinking.

Letting go of his pants she held onto his biceps as he used his free hand to push her hips against his. Still nice and hard. He ran his tongue over her lips and she moaned into his mouth. He worked his warm lips down to her jaw and then he licked upward on her neck, the wet patch was cool on her skin from the air in the kitchen. He did it again and her knees almost gave out. She hadn't been licked like that before.

He kissed over her clavicle and then drew his tongue over her flesh. Her heart was thrumming quickly and she squeezed his strong arms when he rutted against her.

"You good at sucking cock, Y/n?" He pushed his nose against her jawline and the hot breath from his words scattered over the skin on her neck.

"I want to be," she spoke breathlessly, eyes fluttering closed as he mawed at her throat.

He parted from her neck and looked down at her, half-lidded gaze and spit-slicked lips, "Go on."

Instantly she dropped to her knees as her fingers worked deftly at pulling his pants down and then his underwear. She'd sucked a handful of dicks so she knew a couple of moves.

Getting her hand around his thick shaft proved to be a small challenge. To say he was thick… understatement. Long too. His tip was smooth, mushroomed with ridges along the length that she hoped she'd get to feel later on. His was the kind of cock that women dreamed of.

Looking up at him she licked her palm and used her spit to pump him slowly. Another glob over his tip for good measure. Then she pressed a kiss to the base of him, just over his sac, and screwed her eyes upward to watch his expression as she licked his balls, one side at a time. She wound her tongue all around to wet him before sucking at one side, pulling it into her mouth and he let out a ragged breath, his dark pupils spreading inky until the soft green had almost vanished.

He liked it.

She worked around the other side, sucking him in again and swirling her tongue softly underneath the tender bits. He gripped the counter behind himself.

Pulling off she straightened her back and licked upward, feeling every delicious thick ridge along his shaft until her tongue met his smooth crown. Laving every crevice of his tip, she dipped her tongue into his slit and then ran it under the frenulum before she wetted every inch of his glans.

Her mouth was watering when she parted her lips around him and flitted her gaze upward. He was watching her with a slack jaw as she took him a little deeper. He cradled the back of her head and moaned.

"Just suck the tip…."

She blinked up at him and pulled her lips just over the lip, swirling and suckling around him like he wanted.

"Fuck. Just like that." His hand at the back of her head was easy. He didn't push or pull. It was more like a pleased gesture as his fingertips flexed around her skull gently.

Y/n would have liked to have gone deeper. Wanted to show him her best work. But he seemed rather happy with what she was doing.

She bobbed a couple of times, only to slide her lips back to his tip. Her pace was slow when she began to stroke his length with a little twisting motion.

He was big. She knew she could take more but in a way, she was grateful that that was all he was asking for.

A groan fell from his chest and he bucked forward, his cock slipping down her tongue and she sucked, drawing more of him in as she moved her hands away.

"Goddamnit, you're good."

She took that as permission to go deeper. Relaxing her jaw she closed her eyes and held her breath, pushing down to her limit. She filled her throat with his cock the best she could and gurgled around his tip.

He coughed out a moan and then thumbed at her cheek, "Alright, that's good."

She pulled off of him. His heavy cock aimed right at her face when she sat back on her knees and looked up at him, "I can do better than that."

He laughed and put his hand out for her to take, helping her stand up, "I bet you can. Come on."

Harry kept her hand in his as he led her to his bedroom. It was just past the dark living space and he turned on a floor lamp on the opposite side of the room from the bed. When he turned back toward her he cupped her face and kissed her again.

She pressed her hand into his warm, hard chest and he reached around the back of her dress to pull the zipper downward, his fingers dragging down her skin as he went. His touch sent a tremor down her spine as continued kissing her wetly.

He stepped back, helping her out of her dress until it fell to the floor. His eyes raked over her body and he smoothed his hands over her hips and up to her bra-covered breasts. He stepped in closer, walking her backward toward his bed. He put his hands back on her hips and nudged her to sit before he reached down to lift her leg up by her calf, removing her heels, one at a time.

Y/n's thong was drenched. She stared at him while he placed her shoes side by side at the foot of the bed and then he placed his big palms on her thighs, pushing her legs open, "Lie back."

She let her back hit the mattress as Harry got to his knees on the floor. An arm reached under her thigh as he spread her apart and then she felt her panties being pulled at until her her wet pusslips were right in his face. He groaned and felt a hand slide up the inside of her thigh. He pressed his mouth over her mons and looked up at her before he opened his mouth wide and drew his tongue through her crease making her gasp.

"Get your bra off."

She pushed herself up slightly and worked at the clasp of her bra between moans as Harry continued licking at her pussy. When she pulled her arm through the flimsy material he lifted his head and reached around her back, pulling her closer to the edge of the bed and he sucked a nipple into his mouth.

"Oh, fuck!"

Y/n's finger and her long nails pushed into Harry's hair and scraped at his scalp as he licked and pulled at each nipple. He buried his face between her tits and let out a low sound, like he was murmuring something to her but only her breasts were allowed to hear it.

When he sunk back down he pushed at her so she'd lie back and he started in on her clit, one hand holding her panties to the side as he devoured her glistening cunt.

She kept feeling like she was going to slide off the edge of the bed but Harry's grip on her kept her still. His tongue and his lips were magic as he drew her to her end. She yanked at his hair and babbled his name on repeat as her spine bowed off the bed when she came.

Her chest was still rising and falling heavy when she felt her body being pushed upward. She popped her eyes open and watched him roll a condom over his shaft before he kneed back up onto the bed next to her. He was stark naked. His body was insane. Thick muscle and masculine everything. Tattoos scatter over his arms and chest.

Fuck, she muttered under her breath.

"Flip over, for me," his deep voice was husky as he motioned toward her to move.

She rolled to her stomach and she felt his fingers slide between the band of her panties and her hips as he pulled them down her legs.

"Ass up a little. I want to see all of you, Y/n."

She grinned and turned to look at him over her shoulder as she lifted her hips and spread her thighs. His lips were parted as he grabbed her ass and squeezed, making her cheeks spread apart. He inhaled sharply through his teeth and then dipped in, kissing her pussy from behind before licking upward over her ass.

She squealed quietly and bit her lip, still watching him behind her as he lifted, a lopsided grin on his face. He gazed at her as he fisted the base of his cock and slid the head up and down her soaked folds before he tipped his hips to push in just the tip.

"Gorgeous. Gonna look even better wrapped around cock. You like anal?"

"Never tried it."

He licked his lips and pressed his lips together as he looked at the spot where his dick was pressed against her cunt, "Figured. S'alright. Pussy's my favorite anyway."

"We could try… if you want."

He looked back into her eyes, a cocky smile on his face, "Your little hole would need to be trained. And that takes time. So, there will be no anal tonight. Not gonna try and hurt you. But that's a cute thought."

He canted his hips inward, eyes on hers and her mouth dropped open when she felt her entrance splitting open for him. She was tight, but so slick, it only took a few slow thrusts until he was buried in with a low grunt. He pulled back and then pushed his entire length into the hilt.

"Fuck—fuck!" She cried and stuffed her face into the blankets.

"Too much?"

"No! It's so good. You're just so big…" She began to send her hips back against him and Harry slowly fucked in to match her pace. His eyes were everywhere. On her puss getting split open on his cock, the curve of her lower back, the swell of her ass.

He just knew she'd look so sweet with her ass stuffed too, but good things like that couldn't be rushed which was a shame.

Every thrust was gushy wet. Y/n bubbled out small moans every time his dick brushed deep into her guts. It was better than she imagined. The way he filled her to the brim was going to turn into an addiction. She'd never slept with any man that had her wanting seconds before they'd even finished.

"Oh my god…" she mewled into the comforter.

"Fuck, I know, baby…"

She fit him like a glove, it was perfect. He went in a little faster, balls thudding against her skin rhythmically making her bounce forward as she spread around his girth. When he ground in she arched her back deeply and let out a soft groan, her hands fisted at the blanket and Harry reached around and smeared his fingertips over her clit.

It had her panting and pushing into him feverishly. She'd needed the friction on her throbbing button and he'd found it easily, thick, rough fingerprints slicking back and forth as he rutted in and in. It sent electrical sparks over her limbs.

"Like that? Needs her clit touched? Shit baby, act like you've never been touched by a man right here before…" he plucked at her like he was playing the guitar and she began to fade, her moans getting caught in her chest.

He could feel her walls tightening around him as he drove in deep.

"Fuck, Harry— fuck!"

He grinned as he watched her shudder, "Give it up, Y/n. There you go…"

She began to pulse around him, a constant stream of nonsense falling from her lips as he stroked against her channel and pushed deep into her tummy, his fingers still working her clit with ease.

Just as her body had tipped and oxygen returned to her lungs he pulled out and she felt him taking her hips and turning her around to her back. Harry grabbed her ankles and lifted until each was settled over his shoulders and pushed back inside of her, cock drilling down to her core making her teeth chatter at the way he split her down the middle.

Harry leaned over her, cock buried deep as she watched her pretty face twist up with pleasure. Plapping into her, her tits wobbled as his balls tightened against his body. The harder he plunged in, the more her legs shook. Soon, her ankles had slipped down and her feet hit the mattress as he continued drilling into her. His face was flushed hot, lips parted, muscles tensed.

Reaching up to his neck she smoothed her fingers over his warm skin and he lowered his chest down to hers and kissed her. That filthy tongue ran over her lips and he sloppily sipped at her between sucking at her lips. Her brain had turned to jelly.

She felt his hand on her outer thigh squeezing and brushing as he fucked down into her. "Mmm… fuck, Y/n, m'gonna come…"

He trembled over her, thick thighs pressed down and flexed as he rutted in and in and in, and then… he stilled. A deep, guttural moan vibrated through his chest down into hers.

She sighed when she felt him throbbing, pumping into his condom. Her fingers caressed the muscles over his back and she gasped when he bucked in harshly, once more as he emptied the last of his come into the rubber wrapped around his cock.

He slowed his kisses until they were lazy little pecks and then he looked down at her, his chest heaving. She was already grinning up at him.

"What?"

She blinked her eyes, "That was fun."

He puffed out a breath, "I guess that's a good way to describe it."

Harry was a gentleman as he pulled out slowly and helped her off the bed and led her to his bathroom. He helped her clean up and listened to her tell him about her job —just reminding him that she was an adult after he commented on her being so young again.

When she picked her dress up off the floor and started to step into it, Harry frowned, "What are you doing?"

She stopped and raised her brows. "Getting dressed. Was gonna call an Uber. I'm sure you don't want a stranger in your house all night," she laughed.

Harry pulled at her hand, making her drop her dress, "What kind of men have you been hanging out with that let you leave in an Uber at 2 am? You'll stay here."

She opened her mouth and then closed it in surprise before tilting her head in confusion, "Really? I just assumed—"

"You'll stay the night here. There's no way in hell you're getting an Uber at this time of night. It's dangerous."

She grinned and shrugged, "Well then… can I have a shirt or something to sleep in?"

He placed his warm hands on her hips, "You can have a t-shirt if you like. I prefer to sleep naked myself."

"Oh yeah? I usually do too as a matter of fact."

He held her out in his arms and eyed her naked frame, "Looks like we're both good to go then. We'll get you sorted in the morning. I'll give you a ride home then."

"I think you just want to keep me here with you," she chuckled.

Harry shook his head and released her hips before he popped her on the bottom with his palm. She bleated out a laugh.

"Get your ass in bed before I change my mind."

"Yes, sir."

. .

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[gurugirl]

Would you consider writing a matchmaker holiday blurb ? I love that series sooo much 🥺

Yes! I'm already working on a special one for a New Year's holiday thingy!

I think you'll like it!!

xoxo

[gurugirl]

send this to all your favourite moots and roll a snowball! KEEP THE SNOWBALL ROLLING!❄️🤍❄️🤍❄️

Ahhh so cute! THANK YOU!

xoxo

[gurugirl]

AHAHAHAHA!!!

TY Aryn! 🤭 xoxo

DILF | older!harry

MAIN MASTERLIST

Summary: Y/n meets an older man at a bar and she's not taking no for an answer. Harry likes her persistence.

A/N: This was requested + this! Also, please think before you judge Y/n. She is very bold and confident in this. Maybe even a little pushy but Harry likes it (even if at first he doesn't give that impression). Also he's single so this isn't cheatrry!

Word Count: 6,580

Warning: age gap, smut, alcohol consumption (light)

. .

"That one. Total dilf. He looks grumpy. Bet you can't crack him."

Y/n laughed at her friend and looked down at her red-painted nails before narrowing her gaze on the attractive older man who was seated at the corner of the bar alone. He was nursing a whisky and he did look rather sullen. Unapproachable even.

"Why him?"

"Because he's hot. And I'm curious to see if you can get him to smile at least," Warren raised her brows, "I dare you."

Y/n tilted her head and assessed him. He was nice and big, taking up a decent amount of space at the bar, broad shoulders and back hunched as he leaned his muscular forearms on the wood of the bar top. Meaty hands placed on either side of his lowball glass. Thick brown waves on top of his head with a bit of silver coming in at the temples. But the handsome features on his face really set him apart. His granite jawline gave way to stubble that stretched over his skin and shaded in the spaces around his pink lips.

If she could "crack" him she wasn't sure she'd want just a smile. He looked yummy enough to eat.

Drinking down the last of her martini she pointed at Warren and then Tara, "Fine. Give me twenty minutes and I'll have him eating from the palm of my hand."

Tara laughed, "If you say so…"

She placed her heeled feet down on the floor and brushed her hands over her dress, "Oh, I do say so. Just watch and learn, ladies."

Y/n wasn't quite that confident, but she wasn't about to say no to dare. And she could hold her own when it came to flirting. She liked getting a little attention and if she could garner this one's interest it might be fun.

She sauntered up to the bar behind the man and noticed the way his t-shirt stretched over his lats and tapered loosely down at his waist. The guy was fit. And lucky her, there was an open stool next to him.

Sliding onto the seat she waved at the bartender to order another drink. She'd need all the courage she could get, in whatever form she could get it.

Tapping her long nails on the lacquered wood she felt nerves thrumming through veins before turning toward the man finally. He hadn't seemed to take note of her yet, which honestly was unusual in most cases. Maybe she thought too highly of herself but men tended to notice her right away. She appreciated the challenge, though.

Reaching her hand into his space to greet him, she pushed down her nerves to sound steady as she spoke, "I'm Y/n."

She watched his brow furrow as he turned to look at her hand and then up at her eyes, his expression, which she expected would soften once he looked at her, was unamused. A single light overhead lit the tops of their heads as a shadow cast over the side of his face and he didn't make a move to shake her hand, "And I'm old enough to be your dad."

A surprised scoff fell from her lips as she moved her hand away from him. She wiggled in her seat and crossed her leg over her thigh toward him, gulping down the initial rejection with as much grace as she could muster, "I think you're jumping to conclusions about my intentions. But so what if you're older than me? I don't mind. We're both adults, right?"

An unimpressed grunt rumbled from his throat before he took another sip of his whisky and he looked away from her toward the TV that hung not far away from where they sat.

The bartender placed her olive martini down on the bar in front of her, "It'll be on Y/n Y/l/n. I already have an open tab."

A sip of the salty drink felt warm down her throat. So he was going to be a bit tough to crack. She turned to look at her friends who were grinning in her direction.

Straightening her back to feel more confident she tried again, "So you're not gonna tell me your name even?"

Without looking at her, he licked his lips and ticked his jaw, "Y/n, I think it's past your bedtime."

She smiled at that. He'd said her name, which meant he'd been listening, "My bedtime is whenever I say it is, not when some grouchy stranger says."

He puffed out an amused laugh through his nose, "I am a stranger. Which means you should be cautious, little girl. Your dad didn't teach you about things like that?" He turned to look down at her again, and that time she saw the soft green color of his eyes as the light hit his face just right.

But now she was really determined. She smiled brightly at him and let her eyes coast over his tattooed arm and then back up to his face, "Are you telling me you're dangerous?"

He still didn't smile as he shook his head like he was surprised by her gall, "Do your parents know what you're up to tonight?"

"I'm 24. Graduated from college, live on my own, pay my bills, have a full-time job. You seem to be awfully worried about my parents. I can take care of myself just fine."

Just then another person sat down next to the man Y/n was trying to whittle away at. He poked his elbow at him, "Who's this?"

"Don't know. Someone who's about to go back to her table with her little girlfriends."

Biting her lip she traced the rim of her martini glass with her fingertip, keeping her eyes set on the handsome tattooed one, "Not even a smile. Just one? Please?"

"Like I already said, I'm way too old for you."

The other man leaned over and reached to tap Y/n's shoulder, "Hey. Forget about Harry, here. You can bring me home with you if you're looking for a daddy tonight."

She frowned and looked him up and down to asses. He was late 40s perhaps, wearing a local band t-shirt, ripped jeans, and a backward cap to make himself appear a little more youthful. "No thanks. You'd know if I was interested in you."

Harry bit the inside of his cheek to stop himself from smiling at her retort. She was definitely too young but he liked her spunk.

"Now, Harry…" she said his name slowly as she leaned a little closer, "I've got your name thanks to your friend. Can I have a smile?"

"Why?" He stared down at her, the caress of his gaze felt infinite and she found her skin convecting in its wake. He might be hard to crack but this one would be worth it, she determined.

She sighed and slid her finger dangerously close to his wrist as he looked down at her nail and watched her trail it near his arm, "I just hoped to see you smile is all. Too handsome to have such a sour scowl on your face."

"And you're hardly old enough to be so confident to walk up to a strange man at a bar."

She laughed and tilted her head, "You planning on doing something bad to me, Harry?"

And that. That pulled a reaction out of him that spread over his features slowly as he shook his head in disbelief, "Darlin', you wouldn't be able to handle me."

Her eyes widened slightly. Now she was definitely not giving up. Y/n wasn't one to fail and Harry might be making her work hard for it but she couldn't imagine it wouldn't be worth it in the end.

"Is that a challenge or something?" She softly scraped her nail over his tattooed wrist and Harry watched her red nail work over his skin.

His resolve was fading fast. She could tell he wasn't going to keep denying her. And why should he? If he was single, which he appeared to be, what was the harm in having a little fun with someone younger? Y/n didn't mind. And he certainly shouldn't either.

"If it were a challenge you'd know it. Lots of other guys here, Y/n. Go enjoy your night with someone closer to your own age."

She sighed in annoyance. But he hadn't moved his arm away from her and she was going to take that as a sign.

Dragging the toe of her shoe into his shin she grinned, "I don't want to enjoy my night with someone my own age. Not tonight anyway. I think you've convinced me that I need to test out this theory of yours. That you think I can't handle you. Cause I bet I can."

With his eyes piercing into hers, he took another sip of his drink. She thought she might have just convinced him to give her a smile at the very least because it looked like he was weighing his options. And if she could get him to smile she might have luck with the rest.

He tilted his chin upward for a moment, eyes aimed at the ceiling like he was calling on a higher power for strength, "Go back to your friends, Y/n. Any other man here would love to have your company."

"But you wouldn't love to have my company?"

"I mean… I'm still here," the other man raised his hand and leaned into Harry, "Honey we could have so much fun. Any man who'd turn you down is either battin' for the other team or more likely," he chuckled and pushed his shoulder into Harry's teasingly, "He can't get it up anymore."

Y/n's mouth dropped open at that and Harry turned to look at the man. She wished she could see the look on his face, "Sit the fuck back down, John. She already told you she's not interested in you."

"Yeah, and you're not interested in her so what's it matter to you? Look at her, Harry. Practically begging you. Young and bubbly… Tight—"

Harry's hand covered John's throat as he pushed him away, nearly making his stool topple over, "Get the fuck outta here. You had too much whisky tonight."

"Aww… come on Harry… I was just jokin'!"

She watched as he stood from his stool and looked down at John, "And you thought that was funny? You like making jokes about women like that?"

The man put his hands up in surrender, "I'm out. Here…" he threw a wad of cash on the bar top before he moved past Harry and then looked at Y/n, "My apologies if I offended you."

They watched as John left the bar quickly and then Harry sat back down before he waved at the bartender and signaled for the check, "Just the one whisky neat."

"You're leaving already? Night's still young, Harry."

He sucked at his teeth as he scraped his gaze over her face and down to her cleavage. She smiled when she watched the path his eyes had taken.

The bartender handed him the bill and Harry leaned over to pull his wallet from his back pocket.

She scooted closer to him, "You headed home?"

He nodded, but not necessarily in answer to her question, it was more of an appraisal kind of nod. He was still silent as he pulled cash out of his wallet.

"Thanks for that, by the way. I'm sure John's a nice guy and all but he's not really my type. And I'm sure he was wrong about you."

That got his attention. Harry flicked his gaze back to hers, "Wrong about me?"

She smiled, "The part where he said you couldn't get it up. You're not that old. I'm sure you still can. Right?"

He clenched his jaw and breathed out of his nostrils like he couldn't believe she'd asked him such a thing. He handed the bartender his cash with a nod before he stood up from his stool.

"Huh. Since you're so quiet about it maybe he was right," she goaded, pressing her lips together to flatten her smile as she looked up at him through her lashes.

Harry placed a palm down on the bar top next to her hand and leaned over her, "You're out of your depth here, Y/n."

"Now, you don't really know that do you? Just because I'm younger than you doesn't mean I don't know what I'm doing."

"You're awfully pushy. Not used to hearing no, are you?"

Y/n watched as the edge of his mouth lifted in amusement and she widened her eyes and pointed, "You're almost smiling."

He shook his head and looked around the bar before pinning his gaze back to hers, "I hope you enjoy the rest of your night. But your luck has run out with me, princess."

Harry stood to his full height and Y/n decided to try one last time, "So it's true then. What he said."

He stopped and turned to look back at her, a slow burning heat behind his gaze, "Couldn't be further from the truth."

She smiled and slid off her stool to stand in front of him. His height was impressive, "Prove it."

The line of his jaw hardened, turning his cheekbones into slashes of tension. His eyes simmered as he weighed his options. Finally, a hint of a smile stretched over his mouth. A small one, but still.

"I don't need to prove anything to silly little girls."

"Good thing I'm not a silly little girl. I'm a grown woman, Harry."

Y/n knew she was pushing it. She'd never needed to throw herself at any man before. But because of that, she wasn't used to rejection either. Maybe it was a good lesson for her ego. She knew her big fault was how entitled she could act sometimes. But that was partly thanks to how she was raised. It's better to act like a man to get what you want in life, her dad told her. And so far, that had been true. Some women balked at her confidence and her bold attitude. She wasn't demure or sweet enough. And men would often refer to her as a bitch or say that she was trying too hard.

She'd work on her ego another time. But right now? She was focused on winning this battle.

"What do you want with someone like me anyway? Hm? I'm old, Y/n. What's in it for you?"

Blinking her eyes she shook her head, "You're not old, first of all. Secondly, you're really attractive. It doesn't need to go much deeper than that, does it? I just think you're handsome. And I do kind of like a challenge."

"I can see that you like a challenge. It's the only reason I haven't walked out that door yet. Kind of relentless."

She smiled, "So it's working?"

Another half-smile worked its way up his mouth as he laughed in disbelief, "Are you surprised that it is?"

His pupils coasted over her figure and then back up to her face. The warmth of his gaze singed her skin like an open flame.

"I guess I just didn't know how difficult it'd be with you."

He licked his lips, "Difficult. You have no idea. But looks like you're about to find out. Go tell your friends what's going on. Meet me out front."

Y/n watched him turn and walk away. She was shocked. For a minute she thought he wasn't going to go for it at all.

Shaking off the sudden surprise of having gotten to him she settled up with the bartender and then stopped at the table with her friends. They were just about to give her condolences for having oversold her ability but she interrupted. "He's waiting for me outside. Location is on. Don't wait up!"

Harry was leaning against a black car in the parking lot when she stepped out of the doors. The moment he saw her he pushed himself off the car and opened the passenger door for her.

It was going to be tricky to maintain the kind of confidence she'd been feigning with him up until then but there was no part of her that didn't want to find out what he could show her.

She watched as Harry sat down in the driver's seat and started up his car. He took up too much space in the seat. His big hand wrapped around the leather steering wheel while his other encased the shift stick. Even the way he drove was turning her on.

She was pleased that she'd wormed her way under his skin and that he'd given in. She'd try her best to make it worth his while. Reaching across the console she put her hand on his thigh and he glanced down quickly before setting his gaze back on the road.

Now, Harry had slept with younger women a couple of times. He generally preferred someone closer to his age because he liked the confidence and experience that came with age. Women in their 20s were often in a different stage of life and that was fine –normal even, but it just usually wasn't a match for him. Not sexually and not mentally.

But Y/n was unusually confident for being so young. Persistent. He liked it, he couldn't lie. Whether or not she really had much else going for her beyond confidence, he guessed he'd find out. Well, she was very cute too. She did have that in her favor.

And Y/n at least seemed like she knew what she wanted. It was flattering as well. Being approached by such a pretty young thing. He figured the moment he told her to go back to her friends she'd give up but she was just fiery enough that she wasn't deterred.

When she ran her nail over his wrist he knew he was screwed. She was just close enough that he could smell her perfume and then she nudged her shoe into his shin and all he could think about was that she really wanted to be shown a good time and if anyone could it was him.

Harry knew his way around a woman's body. They were all different and he liked finding all the buttons and things that made them purr. In his experience, though, the younger the woman, the less she knew her own body. He didn't know if Y/n was just talking a big game but he was about to find out.

He stayed quiet as she ran her hand down his thigh and he shifted as the car accelerated past the green light. He'd see if she'd do anything with her hand but maybe she'd just pet at him like a novelty toy. He didn't expect—

"This is okay?" She asked him, her tone sultry as she palmed at his crotch.

He licked his lips, "Have at it."

His cock fattened up nicely with not much effort on her part. Proof that he definitely could get it up. Plucking at his button she looked from his face to her fingers as she leaned further over the console to reach her hand into his open pants to help him with the awkward angle of his dick. He seemed to appreciate that as he shifted under her palm.

Rubbing over his heather grey briefs she peeled down the elastic band the slightest to get a peek. The dark shade of pink on his tip matched the muted raspberry of his lips. She slid the pad of her middle finger over the slit and he softly inhaled through his teeth.

She wouldn't be able to give him roadhead like she wanted. It was impossible with the stick shift in the way. But she could wrap her fingers around his shaft and feel him under her palm until they got wherever they were going.

"Mmm… It's so big, Harry. Knew you would be. Might be the biggest I've seen in person. Can't tell yet, though. Have to wait to see when we've got these off."

Harry pushed a laughed breath through his nose. She was a bold thing. Her assertiveness was a turn-on. He didn't like meek and shy. Not when it came to sex.

When she spit into her palm and smeared it down his length, the best she could, he parted his lips and stepped on the gas. She was already exceeding any expectations he had for her. Maybe she'd prove him wrong.

Her nail scraped the underside of him and she moaned, "Really want it in my mouth."

He gulped harshly and ticked his jaw, "Just be patient. I'll let you put it in your mouth soon enough."

"And where are we going? Your place?"

He nodded, "Just a few minutes away."

She squeezed around him and pulled upward slowly. She knew already, he was well above average and she was going to have to work to give him a proper blowy.

His house was a one story, the driveway at the front with a garage attached. He lifted his hand and pushed on a device that was clinging to his sun visor and the garage door began to open. There was a covered motorcycle along the back wall and then the garage door closed after he shut off the engine.

She moved her hand away and unbuckled herself as he got out. When she reached down to pick up her little purse she realized her panties were already wet. She grinned as she stepped out, adjusting her dress before closing the door, and then followed behind him as he led her into a dark hallway.

When he turned on the lights she took it all in. Hardwood floors led into a dining area and then a kitchen. Hung on the walls were photos of himself with two children and then more framed photos with just the kids.

"Do you have kids?"

"I do. Boy and a girl. 7 and 10."

"You're not married are you?"

He laughed, "If I were you'd have known. Wouldn't have been out in the first place if I had a wife waiting for me at home."

She nodded as he turned on the kitchen light and pulled out two glasses before filling them with water.

"Divorced?"

Handing her a glass he squinted, "Yes."

She took a sip. He was a man of few words she'd gathered. She looked around the kitchen. Wood cabinets, an outdated laminate countertop, stainless steel appliances. The space could use some updating but it was large and he had a big pantry.

Sitting the glass down on the counter she watched him closely. His pants were still unbuttoned. She eyed the space at his crotch as he placed his own glass down next to hers.

"It's not gonna suck itself."

She laughed and looked up at him. He had a genuine smile on his face that time. The first real smile she'd seen from him all night. A healthy row of clean teeth, a dimple…

"Hmm… I think you're right. Let's see what we've got…"

She moved in front of him and placed her hands on his pants to push them away but before she could inch them down he wrapped his meaty hand around the back of her neck and drew her into his chest. His mouth was warm and soft. His tongue tasted like the whisky he'd been drinking.

Letting go of his pants she held onto his biceps as he used his free hand to push her hips against his. Still nice and hard. He ran his tongue over her lips and she moaned into his mouth. He worked his warm lips down to her jaw and then he licked upward on her neck, the wet patch was cool on her skin from the air in the kitchen. He did it again and her knees almost gave out. She hadn't been licked like that before.

He kissed over her clavicle and then drew his tongue over her flesh. Her heart was thrumming quickly and she squeezed his strong arms when he rutted against her.

"You good at sucking cock, Y/n?" He pushed his nose against her jawline and the hot breath from his words scattered over the skin on her neck.

"I want to be," she spoke breathlessly, eyes fluttering closed as he mawed at her throat.

He parted from her neck and looked down at her, half-lidded gaze and spit-slicked lips, "Go on."

Instantly she dropped to her knees as her fingers worked deftly at pulling his pants down and then his underwear. She'd sucked a handful of dicks so she knew a couple of moves.

Getting her hand around his thick shaft proved to be a small challenge. To say he was thick… understatement. Long too. His tip was smooth, mushroomed with ridges along the length that she hoped she'd get to feel later on. His was the kind of cock that women dreamed of.

Looking up at him she licked her palm and used her spit to pump him slowly. Another glob over his tip for good measure. Then she pressed a kiss to the base of him, just over his sac, and screwed her eyes upward to watch his expression as she licked his balls, one side at a time. She wound her tongue all around to wet him before sucking at one side, pulling it into her mouth and he let out a ragged breath, his dark pupils spreading inky until the soft green had almost vanished.

He liked it.

She worked around the other side, sucking him in again and swirling her tongue softly underneath the tender bits. He gripped the counter behind himself.

Pulling off she straightened her back and licked upward, feeling every delicious thick ridge along his shaft until her tongue met his smooth crown. Laving every crevice of his tip, she dipped her tongue into his slit and then ran it under the frenulum before she wetted every inch of his glans.

Her mouth was watering when she parted her lips around him and flitted her gaze upward. He was watching her with a slack jaw as she took him a little deeper. He cradled the back of her head and moaned.

"Just suck the tip…."

She blinked up at him and pulled her lips just over the lip, swirling and suckling around him like he wanted.

"Fuck. Just like that." His hand at the back of her head was easy. He didn't push or pull. It was more like a pleased gesture as his fingertips flexed around her skull gently.

Y/n would have liked to have gone deeper. Wanted to show him her best work. But he seemed rather happy with what she was doing.

She bobbed a couple of times, only to slide her lips back to his tip. Her pace was slow when she began to stroke his length with a little twisting motion.

He was big. She knew she could take more but in a way, she was grateful that that was all he was asking for.

A groan fell from his chest and he bucked forward, his cock slipping down her tongue and she sucked, drawing more of him in as she moved her hands away.

"Goddamnit, you're good."

She took that as permission to go deeper. Relaxing her jaw she closed her eyes and held her breath, pushing down to her limit. She filled her throat with his cock the best she could and gurgled around his tip.

He coughed out a moan and then thumbed at her cheek, "Alright, that's good."

She pulled off of him. His heavy cock aimed right at her face when she sat back on her knees and looked up at him, "I can do better than that."

He laughed and put his hand out for her to take, helping her stand up, "I bet you can. Come on."

Harry kept her hand in his as he led her to his bedroom. It was just past the dark living space and he turned on a floor lamp on the opposite side of the room from the bed. When he turned back toward her he cupped her face and kissed her again.

She pressed her hand into his warm, hard chest and he reached around the back of her dress to pull the zipper downward, his fingers dragging down her skin as he went. His touch sent a tremor down her spine as continued kissing her wetly.

He stepped back, helping her out of her dress until it fell to the floor. His eyes raked over her body and he smoothed his hands over her hips and up to her bra-covered breasts. He stepped in closer, walking her backward toward his bed. He put his hands back on her hips and nudged her to sit before he reached down to lift her leg up by her calf, removing her heels, one at a time.

Y/n's thong was drenched. She stared at him while he placed her shoes side by side at the foot of the bed and then he placed his big palms on her thighs, pushing her legs open, "Lie back."

She let her back hit the mattress as Harry got to his knees on the floor. An arm reached under her thigh as he spread her apart and then she felt her panties being pulled at until her her wet pusslips were right in his face. He groaned and felt a hand slide up the inside of her thigh. He pressed his mouth over her mons and looked up at her before he opened his mouth wide and drew his tongue through her crease making her gasp.

"Get your bra off."

She pushed herself up slightly and worked at the clasp of her bra between moans as Harry continued licking at her pussy. When she pulled her arm through the flimsy material he lifted his head and reached around her back, pulling her closer to the edge of the bed and he sucked a nipple into his mouth.

"Oh, fuck!"

Y/n's finger and her long nails pushed into Harry's hair and scraped at his scalp as he licked and pulled at each nipple. He buried his face between her tits and let out a low sound, like he was murmuring something to her but only her breasts were allowed to hear it.

When he sunk back down he pushed at her so she'd lie back and he started in on her clit, one hand holding her panties to the side as he devoured her glistening cunt.

She kept feeling like she was going to slide off the edge of the bed but Harry's grip on her kept her still. His tongue and his lips were magic as he drew her to her end. She yanked at his hair and babbled his name on repeat as her spine bowed off the bed when she came.

Her chest was still rising and falling heavy when she felt her body being pushed upward. She popped her eyes open and watched him roll a condom over his shaft before he kneed back up onto the bed next to her. He was stark naked. His body was insane. Thick muscle and masculine everything. Tattoos scatter over his arms and chest.

Fuck, she muttered under her breath.

"Flip over, for me," his deep voice was husky as he motioned toward her to move.

She rolled to her stomach and she felt his fingers slide between the band of her panties and her hips as he pulled them down her legs.

"Ass up a little. I want to see all of you, Y/n."

She grinned and turned to look at him over her shoulder as she lifted her hips and spread her thighs. His lips were parted as he grabbed her ass and squeezed, making her cheeks spread apart. He inhaled sharply through his teeth and then dipped in, kissing her pussy from behind before licking upward over her ass.

She squealed quietly and bit her lip, still watching him behind her as he lifted, a lopsided grin on his face. He gazed at her as he fisted the base of his cock and slid the head up and down her soaked folds before he tipped his hips to push in just the tip.

"Gorgeous. Gonna look even better wrapped around cock. You like anal?"

"Never tried it."

He licked his lips and pressed his lips together as he looked at the spot where his dick was pressed against her cunt, "Figured. S'alright. Pussy's my favorite anyway."

"We could try… if you want."

He looked back into her eyes, a cocky smile on his face, "Your little hole would need to be trained. And that takes time. So, there will be no anal tonight. Not gonna try and hurt you. But that's a cute thought."

He canted his hips inward, eyes on hers and her mouth dropped open when she felt her entrance splitting open for him. She was tight, but so slick, it only took a few slow thrusts until he was buried in with a low grunt. He pulled back and then pushed his entire length into the hilt.

"Fuck—fuck!" She cried and stuffed her face into the blankets.

"Too much?"

"No! It's so good. You're just so big…" She began to send her hips back against him and Harry slowly fucked in to match her pace. His eyes were everywhere. On her puss getting split open on his cock, the curve of her lower back, the swell of her ass.

He just knew she'd look so sweet with her ass stuffed too, but good things like that couldn't be rushed which was a shame.

Every thrust was gushy wet. Y/n bubbled out small moans every time his dick brushed deep into her guts. It was better than she imagined. The way he filled her to the brim was going to turn into an addiction. She'd never slept with any man that had her wanting seconds before they'd even finished.

"Oh my god…" she mewled into the comforter.

"Fuck, I know, baby…"

She fit him like a glove, it was perfect. He went in a little faster, balls thudding against her skin rhythmically making her bounce forward as she spread around his girth. When he ground in she arched her back deeply and let out a soft groan, her hands fisted at the blanket and Harry reached around and smeared his fingertips over her clit.

It had her panting and pushing into him feverishly. She'd needed the friction on her throbbing button and he'd found it easily, thick, rough fingerprints slicking back and forth as he rutted in and in. It sent electrical sparks over her limbs.

"Like that? Needs her clit touched? Shit baby, act like you've never been touched by a man right here before…" he plucked at her like he was playing the guitar and she began to fade, her moans getting caught in her chest.

He could feel her walls tightening around him as he drove in deep.

"Fuck, Harry— fuck!"

He grinned as he watched her shudder, "Give it up, Y/n. There you go…"

She began to pulse around him, a constant stream of nonsense falling from her lips as he stroked against her channel and pushed deep into her tummy, his fingers still working her clit with ease.

Just as her body had tipped and oxygen returned to her lungs he pulled out and she felt him taking her hips and turning her around to her back. Harry grabbed her ankles and lifted until each was settled over his shoulders and pushed back inside of her, cock drilling down to her core making her teeth chatter at the way he split her down the middle.

Harry leaned over her, cock buried deep as she watched her pretty face twist up with pleasure. Plapping into her, her tits wobbled as his balls tightened against his body. The harder he plunged in, the more her legs shook. Soon, her ankles had slipped down and her feet hit the mattress as he continued drilling into her. His face was flushed hot, lips parted, muscles tensed.

Reaching up to his neck she smoothed her fingers over his warm skin and he lowered his chest down to hers and kissed her. That filthy tongue ran over her lips and he sloppily sipped at her between sucking at her lips. Her brain had turned to jelly.

She felt his hand on her outer thigh squeezing and brushing as he fucked down into her. "Mmm… fuck, Y/n, m'gonna come…"

He trembled over her, thick thighs pressed down and flexed as he rutted in and in and in, and then… he stilled. A deep, guttural moan vibrated through his chest down into hers.

She sighed when she felt him throbbing, pumping into his condom. Her fingers caressed the muscles over his back and she gasped when he bucked in harshly, once more as he emptied the last of his come into the rubber wrapped around his cock.

He slowed his kisses until they were lazy little pecks and then he looked down at her, his chest heaving. She was already grinning up at him.

"What?"

She blinked her eyes, "That was fun."

He puffed out a breath, "I guess that's a good way to describe it."

Harry was a gentleman as he pulled out slowly and helped her off the bed and led her to his bathroom. He helped her clean up and listened to her tell him about her job —just reminding him that she was an adult after he commented on her being so young again.

When she picked her dress up off the floor and started to step into it, Harry frowned, "What are you doing?"

She stopped and raised her brows. "Getting dressed. Was gonna call an Uber. I'm sure you don't want a stranger in your house all night," she laughed.

Harry pulled at her hand, making her drop her dress, "What kind of men have you been hanging out with that let you leave in an Uber at 2 am? You'll stay here."

She opened her mouth and then closed it in surprise before tilting her head in confusion, "Really? I just assumed—"

"You'll stay the night here. There's no way in hell you're getting an Uber at this time of night. It's dangerous."

She grinned and shrugged, "Well then… can I have a shirt or something to sleep in?"

He placed his warm hands on her hips, "You can have a t-shirt if you like. I prefer to sleep naked myself."

"Oh yeah? I usually do too as a matter of fact."

He held her out in his arms and eyed her naked frame, "Looks like we're both good to go then. We'll get you sorted in the morning. I'll give you a ride home then."

"I think you just want to keep me here with you," she chuckled.

Harry shook his head and released her hips before he popped her on the bottom with his palm. She bleated out a laugh.

"Get your ass in bed before I change my mind."

"Yes, sir."

. .

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DILF | older!harry

MAIN MASTERLIST

Summary: Y/n meets an older man at a bar and she's not taking no for an answer. Harry likes her persistence.

A/N: This was requested + this! Also, please think before you judge Y/n. She is very bold and confident in this. Maybe even a little pushy but Harry likes it (even if at first he doesn't give that impression). Also he's single so this isn't cheatrry!

Word Count: 6,580

Warning: age gap, smut, alcohol consumption (light)

. .

"That one. Total dilf. He looks grumpy. Bet you can't crack him."

Y/n laughed at her friend and looked down at her red-painted nails before narrowing her gaze on the attractive older man who was seated at the corner of the bar alone. He was nursing a whisky and he did look rather sullen. Unapproachable even.

"Why him?"

"Because he's hot. And I'm curious to see if you can get him to smile at least," Warren raised her brows, "I dare you."

Y/n tilted her head and assessed him. He was nice and big, taking up a decent amount of space at the bar, broad shoulders and back hunched as he leaned his muscular forearms on the wood of the bar top. Meaty hands placed on either side of his lowball glass. Thick brown waves on top of his head with a bit of silver coming in at the temples. But the handsome features on his face really set him apart. His granite jawline gave way to stubble that stretched over his skin and shaded in the spaces around his pink lips.

If she could "crack" him she wasn't sure she'd want just a smile. He looked yummy enough to eat.

Drinking down the last of her martini she pointed at Warren and then Tara, "Fine. Give me twenty minutes and I'll have him eating from the palm of my hand."

Tara laughed, "If you say so…"

She placed her heeled feet down on the floor and brushed her hands over her dress, "Oh, I do say so. Just watch and learn, ladies."

Y/n wasn't quite that confident, but she wasn't about to say no to dare. And she could hold her own when it came to flirting. She liked getting a little attention and if she could garner this one's interest it might be fun.

She sauntered up to the bar behind the man and noticed the way his t-shirt stretched over his lats and tapered loosely down at his waist. The guy was fit. And lucky her, there was an open stool next to him.

Sliding onto the seat she waved at the bartender to order another drink. She'd need all the courage she could get, in whatever form she could get it.

Tapping her long nails on the lacquered wood she felt nerves thrumming through veins before turning toward the man finally. He hadn't seemed to take note of her yet, which honestly was unusual in most cases. Maybe she thought too highly of herself but men tended to notice her right away. She appreciated the challenge, though.

Reaching her hand into his space to greet him, she pushed down her nerves to sound steady as she spoke, "I'm Y/n."

She watched his brow furrow as he turned to look at her hand and then up at her eyes, his expression, which she expected would soften once he looked at her, was unamused. A single light overhead lit the tops of their heads as a shadow cast over the side of his face and he didn't make a move to shake her hand, "And I'm old enough to be your dad."

A surprised scoff fell from her lips as she moved her hand away from him. She wiggled in her seat and crossed her leg over her thigh toward him, gulping down the initial rejection with as much grace as she could muster, "I think you're jumping to conclusions about my intentions. But so what if you're older than me? I don't mind. We're both adults, right?"

An unimpressed grunt rumbled from his throat before he took another sip of his whisky and he looked away from her toward the TV that hung not far away from where they sat.

The bartender placed her olive martini down on the bar in front of her, "It'll be on Y/n Y/l/n. I already have an open tab."

A sip of the salty drink felt warm down her throat. So he was going to be a bit tough to crack. She turned to look at her friends who were grinning in her direction.

Straightening her back to feel more confident she tried again, "So you're not gonna tell me your name even?"

Without looking at her, he licked his lips and ticked his jaw, "Y/n, I think it's past your bedtime."

She smiled at that. He'd said her name, which meant he'd been listening, "My bedtime is whenever I say it is, not when some grouchy stranger says."

He puffed out an amused laugh through his nose, "I am a stranger. Which means you should be cautious, little girl. Your dad didn't teach you about things like that?" He turned to look down at her again, and that time she saw the soft green color of his eyes as the light hit his face just right.

But now she was really determined. She smiled brightly at him and let her eyes coast over his tattooed arm and then back up to his face, "Are you telling me you're dangerous?"

He still didn't smile as he shook his head like he was surprised by her gall, "Do your parents know what you're up to tonight?"

"I'm 24. Graduated from college, live on my own, pay my bills, have a full-time job. You seem to be awfully worried about my parents. I can take care of myself just fine."

Just then another person sat down next to the man Y/n was trying to whittle away at. He poked his elbow at him, "Who's this?"

"Don't know. Someone who's about to go back to her table with her little girlfriends."

Biting her lip she traced the rim of her martini glass with her fingertip, keeping her eyes set on the handsome tattooed one, "Not even a smile. Just one? Please?"

"Like I already said, I'm way too old for you."

The other man leaned over and reached to tap Y/n's shoulder, "Hey. Forget about Harry, here. You can bring me home with you if you're looking for a daddy tonight."

She frowned and looked him up and down to asses. He was late 40s perhaps, wearing a local band t-shirt, ripped jeans, and a backward cap to make himself appear a little more youthful. "No thanks. You'd know if I was interested in you."

Harry bit the inside of his cheek to stop himself from smiling at her retort. She was definitely too young but he liked her spunk.

"Now, Harry…" she said his name slowly as she leaned a little closer, "I've got your name thanks to your friend. Can I have a smile?"

"Why?" He stared down at her, the caress of his gaze felt infinite and she found her skin convecting in its wake. He might be hard to crack but this one would be worth it, she determined.

She sighed and slid her finger dangerously close to his wrist as he looked down at her nail and watched her trail it near his arm, "I just hoped to see you smile is all. Too handsome to have such a sour scowl on your face."

"And you're hardly old enough to be so confident to walk up to a strange man at a bar."

She laughed and tilted her head, "You planning on doing something bad to me, Harry?"

And that. That pulled a reaction out of him that spread over his features slowly as he shook his head in disbelief, "Darlin', you wouldn't be able to handle me."

Her eyes widened slightly. Now she was definitely not giving up. Y/n wasn't one to fail and Harry might be making her work hard for it but she couldn't imagine it wouldn't be worth it in the end.

"Is that a challenge or something?" She softly scraped her nail over his tattooed wrist and Harry watched her red nail work over his skin.

His resolve was fading fast. She could tell he wasn't going to keep denying her. And why should he? If he was single, which he appeared to be, what was the harm in having a little fun with someone younger? Y/n didn't mind. And he certainly shouldn't either.

"If it were a challenge you'd know it. Lots of other guys here, Y/n. Go enjoy your night with someone closer to your own age."

She sighed in annoyance. But he hadn't moved his arm away from her and she was going to take that as a sign.

Dragging the toe of her shoe into his shin she grinned, "I don't want to enjoy my night with someone my own age. Not tonight anyway. I think you've convinced me that I need to test out this theory of yours. That you think I can't handle you. Cause I bet I can."

With his eyes piercing into hers, he took another sip of his drink. She thought she might have just convinced him to give her a smile at the very least because it looked like he was weighing his options. And if she could get him to smile she might have luck with the rest.

He tilted his chin upward for a moment, eyes aimed at the ceiling like he was calling on a higher power for strength, "Go back to your friends, Y/n. Any other man here would love to have your company."

"But you wouldn't love to have my company?"

"I mean… I'm still here," the other man raised his hand and leaned into Harry, "Honey we could have so much fun. Any man who'd turn you down is either battin' for the other team or more likely," he chuckled and pushed his shoulder into Harry's teasingly, "He can't get it up anymore."

Y/n's mouth dropped open at that and Harry turned to look at the man. She wished she could see the look on his face, "Sit the fuck back down, John. She already told you she's not interested in you."

"Yeah, and you're not interested in her so what's it matter to you? Look at her, Harry. Practically begging you. Young and bubbly… Tight—"

Harry's hand covered John's throat as he pushed him away, nearly making his stool topple over, "Get the fuck outta here. You had too much whisky tonight."

"Aww… come on Harry… I was just jokin'!"

She watched as he stood from his stool and looked down at John, "And you thought that was funny? You like making jokes about women like that?"

The man put his hands up in surrender, "I'm out. Here…" he threw a wad of cash on the bar top before he moved past Harry and then looked at Y/n, "My apologies if I offended you."

They watched as John left the bar quickly and then Harry sat back down before he waved at the bartender and signaled for the check, "Just the one whisky neat."

"You're leaving already? Night's still young, Harry."

He sucked at his teeth as he scraped his gaze over her face and down to her cleavage. She smiled when she watched the path his eyes had taken.

The bartender handed him the bill and Harry leaned over to pull his wallet from his back pocket.

She scooted closer to him, "You headed home?"

He nodded, but not necessarily in answer to her question, it was more of an appraisal kind of nod. He was still silent as he pulled cash out of his wallet.

"Thanks for that, by the way. I'm sure John's a nice guy and all but he's not really my type. And I'm sure he was wrong about you."

That got his attention. Harry flicked his gaze back to hers, "Wrong about me?"

She smiled, "The part where he said you couldn't get it up. You're not that old. I'm sure you still can. Right?"

He clenched his jaw and breathed out of his nostrils like he couldn't believe she'd asked him such a thing. He handed the bartender his cash with a nod before he stood up from his stool.

"Huh. Since you're so quiet about it maybe he was right," she goaded, pressing her lips together to flatten her smile as she looked up at him through her lashes.

Harry placed a palm down on the bar top next to her hand and leaned over her, "You're out of your depth here, Y/n."

"Now, you don't really know that do you? Just because I'm younger than you doesn't mean I don't know what I'm doing."

"You're awfully pushy. Not used to hearing no, are you?"

Y/n watched as the edge of his mouth lifted in amusement and she widened her eyes and pointed, "You're almost smiling."

He shook his head and looked around the bar before pinning his gaze back to hers, "I hope you enjoy the rest of your night. But your luck has run out with me, princess."

Harry stood to his full height and Y/n decided to try one last time, "So it's true then. What he said."

He stopped and turned to look back at her, a slow burning heat behind his gaze, "Couldn't be further from the truth."

She smiled and slid off her stool to stand in front of him. His height was impressive, "Prove it."

The line of his jaw hardened, turning his cheekbones into slashes of tension. His eyes simmered as he weighed his options. Finally, a hint of a smile stretched over his mouth. A small one, but still.

"I don't need to prove anything to silly little girls."

"Good thing I'm not a silly little girl. I'm a grown woman, Harry."

Y/n knew she was pushing it. She'd never needed to throw herself at any man before. But because of that, she wasn't used to rejection either. Maybe it was a good lesson for her ego. She knew her big fault was how entitled she could act sometimes. But that was partly thanks to how she was raised. It's better to act like a man to get what you want in life, her dad told her. And so far, that had been true. Some women balked at her confidence and her bold attitude. She wasn't demure or sweet enough. And men would often refer to her as a bitch or say that she was trying too hard.

She'd work on her ego another time. But right now? She was focused on winning this battle.

"What do you want with someone like me anyway? Hm? I'm old, Y/n. What's in it for you?"

Blinking her eyes she shook her head, "You're not old, first of all. Secondly, you're really attractive. It doesn't need to go much deeper than that, does it? I just think you're handsome. And I do kind of like a challenge."

"I can see that you like a challenge. It's the only reason I haven't walked out that door yet. Kind of relentless."

She smiled, "So it's working?"

Another half-smile worked its way up his mouth as he laughed in disbelief, "Are you surprised that it is?"

His pupils coasted over her figure and then back up to her face. The warmth of his gaze singed her skin like an open flame.

"I guess I just didn't know how difficult it'd be with you."

He licked his lips, "Difficult. You have no idea. But looks like you're about to find out. Go tell your friends what's going on. Meet me out front."

Y/n watched him turn and walk away. She was shocked. For a minute she thought he wasn't going to go for it at all.

Shaking off the sudden surprise of having gotten to him she settled up with the bartender and then stopped at the table with her friends. They were just about to give her condolences for having oversold her ability but she interrupted. "He's waiting for me outside. Location is on. Don't wait up!"

Harry was leaning against a black car in the parking lot when she stepped out of the doors. The moment he saw her he pushed himself off the car and opened the passenger door for her.

It was going to be tricky to maintain the kind of confidence she'd been feigning with him up until then but there was no part of her that didn't want to find out what he could show her.

She watched as Harry sat down in the driver's seat and started up his car. He took up too much space in the seat. His big hand wrapped around the leather steering wheel while his other encased the shift stick. Even the way he drove was turning her on.

She was pleased that she'd wormed her way under his skin and that he'd given in. She'd try her best to make it worth his while. Reaching across the console she put her hand on his thigh and he glanced down quickly before setting his gaze back on the road.

Now, Harry had slept with younger women a couple of times. He generally preferred someone closer to his age because he liked the confidence and experience that came with age. Women in their 20s were often in a different stage of life and that was fine –normal even, but it just usually wasn't a match for him. Not sexually and not mentally.

But Y/n was unusually confident for being so young. Persistent. He liked it, he couldn't lie. Whether or not she really had much else going for her beyond confidence, he guessed he'd find out. Well, she was very cute too. She did have that in her favor.

And Y/n at least seemed like she knew what she wanted. It was flattering as well. Being approached by such a pretty young thing. He figured the moment he told her to go back to her friends she'd give up but she was just fiery enough that she wasn't deterred.

When she ran her nail over his wrist he knew he was screwed. She was just close enough that he could smell her perfume and then she nudged her shoe into his shin and all he could think about was that she really wanted to be shown a good time and if anyone could it was him.

Harry knew his way around a woman's body. They were all different and he liked finding all the buttons and things that made them purr. In his experience, though, the younger the woman, the less she knew her own body. He didn't know if Y/n was just talking a big game but he was about to find out.

He stayed quiet as she ran her hand down his thigh and he shifted as the car accelerated past the green light. He'd see if she'd do anything with her hand but maybe she'd just pet at him like a novelty toy. He didn't expect—

"This is okay?" She asked him, her tone sultry as she palmed at his crotch.

He licked his lips, "Have at it."

His cock fattened up nicely with not much effort on her part. Proof that he definitely could get it up. Plucking at his button she looked from his face to her fingers as she leaned further over the console to reach her hand into his open pants to help him with the awkward angle of his dick. He seemed to appreciate that as he shifted under her palm.

Rubbing over his heather grey briefs she peeled down the elastic band the slightest to get a peek. The dark shade of pink on his tip matched the muted raspberry of his lips. She slid the pad of her middle finger over the slit and he softly inhaled through his teeth.

She wouldn't be able to give him roadhead like she wanted. It was impossible with the stick shift in the way. But she could wrap her fingers around his shaft and feel him under her palm until they got wherever they were going.

"Mmm… It's so big, Harry. Knew you would be. Might be the biggest I've seen in person. Can't tell yet, though. Have to wait to see when we've got these off."

Harry pushed a laughed breath through his nose. She was a bold thing. Her assertiveness was a turn-on. He didn't like meek and shy. Not when it came to sex.

When she spit into her palm and smeared it down his length, the best she could, he parted his lips and stepped on the gas. She was already exceeding any expectations he had for her. Maybe she'd prove him wrong.

Her nail scraped the underside of him and she moaned, "Really want it in my mouth."

He gulped harshly and ticked his jaw, "Just be patient. I'll let you put it in your mouth soon enough."

"And where are we going? Your place?"

He nodded, "Just a few minutes away."

She squeezed around him and pulled upward slowly. She knew already, he was well above average and she was going to have to work to give him a proper blowy.

His house was a one story, the driveway at the front with a garage attached. He lifted his hand and pushed on a device that was clinging to his sun visor and the garage door began to open. There was a covered motorcycle along the back wall and then the garage door closed after he shut off the engine.

She moved her hand away and unbuckled herself as he got out. When she reached down to pick up her little purse she realized her panties were already wet. She grinned as she stepped out, adjusting her dress before closing the door, and then followed behind him as he led her into a dark hallway.

When he turned on the lights she took it all in. Hardwood floors led into a dining area and then a kitchen. Hung on the walls were photos of himself with two children and then more framed photos with just the kids.

"Do you have kids?"

"I do. Boy and a girl. 7 and 10."

"You're not married are you?"

He laughed, "If I were you'd have known. Wouldn't have been out in the first place if I had a wife waiting for me at home."

She nodded as he turned on the kitchen light and pulled out two glasses before filling them with water.

"Divorced?"

Handing her a glass he squinted, "Yes."

She took a sip. He was a man of few words she'd gathered. She looked around the kitchen. Wood cabinets, an outdated laminate countertop, stainless steel appliances. The space could use some updating but it was large and he had a big pantry.

Sitting the glass down on the counter she watched him closely. His pants were still unbuttoned. She eyed the space at his crotch as he placed his own glass down next to hers.

"It's not gonna suck itself."

She laughed and looked up at him. He had a genuine smile on his face that time. The first real smile she'd seen from him all night. A healthy row of clean teeth, a dimple…

"Hmm… I think you're right. Let's see what we've got…"

She moved in front of him and placed her hands on his pants to push them away but before she could inch them down he wrapped his meaty hand around the back of her neck and drew her into his chest. His mouth was warm and soft. His tongue tasted like the whisky he'd been drinking.

Letting go of his pants she held onto his biceps as he used his free hand to push her hips against his. Still nice and hard. He ran his tongue over her lips and she moaned into his mouth. He worked his warm lips down to her jaw and then he licked upward on her neck, the wet patch was cool on her skin from the air in the kitchen. He did it again and her knees almost gave out. She hadn't been licked like that before.

He kissed over her clavicle and then drew his tongue over her flesh. Her heart was thrumming quickly and she squeezed his strong arms when he rutted against her.

"You good at sucking cock, Y/n?" He pushed his nose against her jawline and the hot breath from his words scattered over the skin on her neck.

"I want to be," she spoke breathlessly, eyes fluttering closed as he mawed at her throat.

He parted from her neck and looked down at her, half-lidded gaze and spit-slicked lips, "Go on."

Instantly she dropped to her knees as her fingers worked deftly at pulling his pants down and then his underwear. She'd sucked a handful of dicks so she knew a couple of moves.

Getting her hand around his thick shaft proved to be a small challenge. To say he was thick… understatement. Long too. His tip was smooth, mushroomed with ridges along the length that she hoped she'd get to feel later on. His was the kind of cock that women dreamed of.

Looking up at him she licked her palm and used her spit to pump him slowly. Another glob over his tip for good measure. Then she pressed a kiss to the base of him, just over his sac, and screwed her eyes upward to watch his expression as she licked his balls, one side at a time. She wound her tongue all around to wet him before sucking at one side, pulling it into her mouth and he let out a ragged breath, his dark pupils spreading inky until the soft green had almost vanished.

He liked it.

She worked around the other side, sucking him in again and swirling her tongue softly underneath the tender bits. He gripped the counter behind himself.

Pulling off she straightened her back and licked upward, feeling every delicious thick ridge along his shaft until her tongue met his smooth crown. Laving every crevice of his tip, she dipped her tongue into his slit and then ran it under the frenulum before she wetted every inch of his glans.

Her mouth was watering when she parted her lips around him and flitted her gaze upward. He was watching her with a slack jaw as she took him a little deeper. He cradled the back of her head and moaned.

"Just suck the tip…."

She blinked up at him and pulled her lips just over the lip, swirling and suckling around him like he wanted.

"Fuck. Just like that." His hand at the back of her head was easy. He didn't push or pull. It was more like a pleased gesture as his fingertips flexed around her skull gently.

Y/n would have liked to have gone deeper. Wanted to show him her best work. But he seemed rather happy with what she was doing.

She bobbed a couple of times, only to slide her lips back to his tip. Her pace was slow when she began to stroke his length with a little twisting motion.

He was big. She knew she could take more but in a way, she was grateful that that was all he was asking for.

A groan fell from his chest and he bucked forward, his cock slipping down her tongue and she sucked, drawing more of him in as she moved her hands away.

"Goddamnit, you're good."

She took that as permission to go deeper. Relaxing her jaw she closed her eyes and held her breath, pushing down to her limit. She filled her throat with his cock the best she could and gurgled around his tip.

He coughed out a moan and then thumbed at her cheek, "Alright, that's good."

She pulled off of him. His heavy cock aimed right at her face when she sat back on her knees and looked up at him, "I can do better than that."

He laughed and put his hand out for her to take, helping her stand up, "I bet you can. Come on."

Harry kept her hand in his as he led her to his bedroom. It was just past the dark living space and he turned on a floor lamp on the opposite side of the room from the bed. When he turned back toward her he cupped her face and kissed her again.

She pressed her hand into his warm, hard chest and he reached around the back of her dress to pull the zipper downward, his fingers dragging down her skin as he went. His touch sent a tremor down her spine as continued kissing her wetly.

He stepped back, helping her out of her dress until it fell to the floor. His eyes raked over her body and he smoothed his hands over her hips and up to her bra-covered breasts. He stepped in closer, walking her backward toward his bed. He put his hands back on her hips and nudged her to sit before he reached down to lift her leg up by her calf, removing her heels, one at a time.

Y/n's thong was drenched. She stared at him while he placed her shoes side by side at the foot of the bed and then he placed his big palms on her thighs, pushing her legs open, "Lie back."

She let her back hit the mattress as Harry got to his knees on the floor. An arm reached under her thigh as he spread her apart and then she felt her panties being pulled at until her her wet pusslips were right in his face. He groaned and felt a hand slide up the inside of her thigh. He pressed his mouth over her mons and looked up at her before he opened his mouth wide and drew his tongue through her crease making her gasp.

"Get your bra off."

She pushed herself up slightly and worked at the clasp of her bra between moans as Harry continued licking at her pussy. When she pulled her arm through the flimsy material he lifted his head and reached around her back, pulling her closer to the edge of the bed and he sucked a nipple into his mouth.

"Oh, fuck!"

Y/n's finger and her long nails pushed into Harry's hair and scraped at his scalp as he licked and pulled at each nipple. He buried his face between her tits and let out a low sound, like he was murmuring something to her but only her breasts were allowed to hear it.

When he sunk back down he pushed at her so she'd lie back and he started in on her clit, one hand holding her panties to the side as he devoured her glistening cunt.

She kept feeling like she was going to slide off the edge of the bed but Harry's grip on her kept her still. His tongue and his lips were magic as he drew her to her end. She yanked at his hair and babbled his name on repeat as her spine bowed off the bed when she came.

Her chest was still rising and falling heavy when she felt her body being pushed upward. She popped her eyes open and watched him roll a condom over his shaft before he kneed back up onto the bed next to her. He was stark naked. His body was insane. Thick muscle and masculine everything. Tattoos scatter over his arms and chest.

Fuck, she muttered under her breath.

"Flip over, for me," his deep voice was husky as he motioned toward her to move.

She rolled to her stomach and she felt his fingers slide between the band of her panties and her hips as he pulled them down her legs.

"Ass up a little. I want to see all of you, Y/n."

She grinned and turned to look at him over her shoulder as she lifted her hips and spread her thighs. His lips were parted as he grabbed her ass and squeezed, making her cheeks spread apart. He inhaled sharply through his teeth and then dipped in, kissing her pussy from behind before licking upward over her ass.

She squealed quietly and bit her lip, still watching him behind her as he lifted, a lopsided grin on his face. He gazed at her as he fisted the base of his cock and slid the head up and down her soaked folds before he tipped his hips to push in just the tip.

"Gorgeous. Gonna look even better wrapped around cock. You like anal?"

"Never tried it."

He licked his lips and pressed his lips together as he looked at the spot where his dick was pressed against her cunt, "Figured. S'alright. Pussy's my favorite anyway."

"We could try… if you want."

He looked back into her eyes, a cocky smile on his face, "Your little hole would need to be trained. And that takes time. So, there will be no anal tonight. Not gonna try and hurt you. But that's a cute thought."

He canted his hips inward, eyes on hers and her mouth dropped open when she felt her entrance splitting open for him. She was tight, but so slick, it only took a few slow thrusts until he was buried in with a low grunt. He pulled back and then pushed his entire length into the hilt.

"Fuck—fuck!" She cried and stuffed her face into the blankets.

"Too much?"

"No! It's so good. You're just so big…" She began to send her hips back against him and Harry slowly fucked in to match her pace. His eyes were everywhere. On her puss getting split open on his cock, the curve of her lower back, the swell of her ass.

He just knew she'd look so sweet with her ass stuffed too, but good things like that couldn't be rushed which was a shame.

Every thrust was gushy wet. Y/n bubbled out small moans every time his dick brushed deep into her guts. It was better than she imagined. The way he filled her to the brim was going to turn into an addiction. She'd never slept with any man that had her wanting seconds before they'd even finished.

"Oh my god…" she mewled into the comforter.

"Fuck, I know, baby…"

She fit him like a glove, it was perfect. He went in a little faster, balls thudding against her skin rhythmically making her bounce forward as she spread around his girth. When he ground in she arched her back deeply and let out a soft groan, her hands fisted at the blanket and Harry reached around and smeared his fingertips over her clit.

It had her panting and pushing into him feverishly. She'd needed the friction on her throbbing button and he'd found it easily, thick, rough fingerprints slicking back and forth as he rutted in and in. It sent electrical sparks over her limbs.

"Like that? Needs her clit touched? Shit baby, act like you've never been touched by a man right here before…" he plucked at her like he was playing the guitar and she began to fade, her moans getting caught in her chest.

He could feel her walls tightening around him as he drove in deep.

"Fuck, Harry— fuck!"

He grinned as he watched her shudder, "Give it up, Y/n. There you go…"

She began to pulse around him, a constant stream of nonsense falling from her lips as he stroked against her channel and pushed deep into her tummy, his fingers still working her clit with ease.

Just as her body had tipped and oxygen returned to her lungs he pulled out and she felt him taking her hips and turning her around to her back. Harry grabbed her ankles and lifted until each was settled over his shoulders and pushed back inside of her, cock drilling down to her core making her teeth chatter at the way he split her down the middle.

Harry leaned over her, cock buried deep as she watched her pretty face twist up with pleasure. Plapping into her, her tits wobbled as his balls tightened against his body. The harder he plunged in, the more her legs shook. Soon, her ankles had slipped down and her feet hit the mattress as he continued drilling into her. His face was flushed hot, lips parted, muscles tensed.

Reaching up to his neck she smoothed her fingers over his warm skin and he lowered his chest down to hers and kissed her. That filthy tongue ran over her lips and he sloppily sipped at her between sucking at her lips. Her brain had turned to jelly.

She felt his hand on her outer thigh squeezing and brushing as he fucked down into her. "Mmm… fuck, Y/n, m'gonna come…"

He trembled over her, thick thighs pressed down and flexed as he rutted in and in and in, and then… he stilled. A deep, guttural moan vibrated through his chest down into hers.

She sighed when she felt him throbbing, pumping into his condom. Her fingers caressed the muscles over his back and she gasped when he bucked in harshly, once more as he emptied the last of his come into the rubber wrapped around his cock.

He slowed his kisses until they were lazy little pecks and then he looked down at her, his chest heaving. She was already grinning up at him.

"What?"

She blinked her eyes, "That was fun."

He puffed out a breath, "I guess that's a good way to describe it."

Harry was a gentleman as he pulled out slowly and helped her off the bed and led her to his bathroom. He helped her clean up and listened to her tell him about her job —just reminding him that she was an adult after he commented on her being so young again.

When she picked her dress up off the floor and started to step into it, Harry frowned, "What are you doing?"

She stopped and raised her brows. "Getting dressed. Was gonna call an Uber. I'm sure you don't want a stranger in your house all night," she laughed.

Harry pulled at her hand, making her drop her dress, "What kind of men have you been hanging out with that let you leave in an Uber at 2 am? You'll stay here."

She opened her mouth and then closed it in surprise before tilting her head in confusion, "Really? I just assumed—"

"You'll stay the night here. There's no way in hell you're getting an Uber at this time of night. It's dangerous."

She grinned and shrugged, "Well then… can I have a shirt or something to sleep in?"

He placed his warm hands on her hips, "You can have a t-shirt if you like. I prefer to sleep naked myself."

"Oh yeah? I usually do too as a matter of fact."

He held her out in his arms and eyed her naked frame, "Looks like we're both good to go then. We'll get you sorted in the morning. I'll give you a ride home then."

"I think you just want to keep me here with you," she chuckled.

Harry shook his head and released her hips before he popped her on the bottom with his palm. She bleated out a laugh.

"Get your ass in bed before I change my mind."

"Yes, sir."

. .

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[gurugirl]

You guys! Boss!harry is complete! I hope those of you who were enjoying it liked the last 2 parts! I had so much fun writing them.

This series is 10 parts and around 47k words total. Planning on a cute little holiday blurb for them next week as well.

Appreciate all the feedback on this one, thank you guys!

xoxo

Boss!harry | series preview

This is a Patreon-only series!

Summary: Harry's your boss and you're trying really hard not to develop feelings for him.

Warning: This is an angsty series y'all!

His warm hand smoothed over your hip and curled around your side as he scooted in closer.

You weren't sure what to expect when he'd wake up. You thought maybe he'd be right back to business, take you back to your car so you could go home and get yourself ready for the day. You hadn't expected that he'd be kissing up the column of your neck to your jaw with hot puffs of breath falling from his mouth and spreading over your skin slowly like melting wax.

You also hadn't expected your body's immediate reaction to him. The liquid heat pooling between your naked thighs and the way your nipples tightened underneath the cotton of his t-shirt. When he slid his hand underneath the fabric and up your tummy to your breast you rattled a moan that sounded like desperation. The way he squeezed around your sensitive tits was something you had no idea you needed. He practically worshiped your nipples and the soft plush skin of your breasts the night before.

The blankets tangled around your ankle as you rolled to your side to face him and he pulled you in by your thigh, pressing your naked core against his morning wood.

Fuck.

It was one thing to have a wild night with your excruciatingly handsome boss, but it was another to do it again upon waking before you were meant to be at work and pretending like nothing had happened.

Pretending. You could pretend. You'd have to because he made it clear the night before that this wasn't a thing. That this was just sex and you'd need to keep it quiet. That it wasn't going to happen again. It couldn't.

Which meant the way he touched you was just sex, just something for that moment. The way the remnants of his palm prints burned into your skin left behind something that would turn hollow and bitter the moment you left his front door made your stomach curl into itself.

You swallowed down the loss before it had even arrived. A one-night stand with your boss was a bad idea and this was why. Harry would be fine after (he could have anyone he wanted) and you'd be left reeling and abandoned. Again. Because this is what men did. You were only good for as long as they saw fit. And after this, Harry wouldn't want or need anything more from you. Why would he?

"Y/n…" he breathed your name against your lips, "Already shaking and I've barely touched you, baby. God I just wanna eat you alive."

He would eat you alive too. Chew you up and spit you right back out. But you wouldn't stop him from doing it. You couldn't stop it because if that's all it could be you'd take the last bits of what he'd offer and be on your way.

It was a sleepy morning, hazy, blurry, soft… Harry's hands and his tongue worked down your body until he'd found your pussy and he slowly, lazily ate you out until you were coming and crying.

And that time, when he fucked into you, it was slow and steady. Slippery wet. Your bare breasts were pressed into his chest as he licked into your mouth and the embers grew and sparked until they caught and your body was at the edge of surrender.

"Fuck your pussy feels just right," he groaned as he dragged himself through your walls, coating himself in your arousal, your scent.

You whimpered and stuffed your fingers into his hair as he ground his pelvis into your clit. The perfect angle, the perfect cock. Too bad he wasn't the perfect man. You couldn't have him. For obvious reasons.

Your throaty moans were swallowed by his mouth, his length smashing into your guts with a wet slapping sound as you both moved together as one. Sex and sweat and heat and the imprint of desire.

He was soft; his words, his cadence, his hands… but the thick and heavy organ moving into your tummy was anything but soft; stiff, masculine, and rigid, it stretched your insides wide open. He needed the room and your body accommodated every inch of him. Gushy.

When he spoke against your ear, the hitch in his voice was almost whiny, like he was the one who was going to feel the loss. Like he was going to be left hollow and you were the one eating him alive, "Baby… shit. Right there?" He nudged into you and stilled himself so you could feel what he meant. Right there. Yes. Right there. Tight and spongy, the pulse emanating from your cunt was wrapped around him, a rhythmic beating that tremored down through his cock and into the veins and nerve endings. Connected.

You stuffed down the dribble of emotion that swelled in your throat and threatened to break from your waterline.

It's just sex. You're a sexual being who needed a good release. It's just sex. You don't need him. It's. Just. Sex.

But it certainly didn't just feel like sex when his soft green irises found your gaze and he held it as he languidly rocked into you. He dotted kisses along your face and then he'd watch you for a moment and it was going to have you mixed up because it was so intimate. So tender of him.

Maybe if he'd flip you around and fuck you from behind and give you a nice spanking it'd feel like just sex. He'd done that the night before (among other positions). Had you drooling into his mattress as he plowed into you from behind, a couple of good swats on your ass as he said filthy things to you. That felt like just sex. Good sex, but still.

So the soft and slow morning fuck with gentle kisses and an easy, damp tongue over your parted lips, his eyes connected to yours as he moaned and slid his thumb at your temple – that was not just sex and you didn't want it.

Well, you did want it. You really did because you wanted to find someone that would do all those things. But you wanted that for good. Not just for the night.

"Are you okay, Y/n?" Harry sponged a kiss to the edge of your mouth.

"Yeah. I'm okay," you were breathless and on the edge of tears. A ridiculous girl.

"Does it hurt from last night? Was it too much?"

Swallowing you blinked your eyes and he was still softly caressing your face with his thumb like only a lover would do.

"It… a little. I feel fine now. You're so gentle so it's okay."

"That's why I'm being careful. Thought you might need it softer this morning. Are you sure you're okay?"

Too attentive. Too thoughtful. Too present. How were you going to separate your romantic nature from your carnal one? How did all the other women do it? You were sure he was like this with every girl he brought to his bed.

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[gurugirl]

Thank you 😭😭 Hahaha! It was fun to write! Happy you liked YN! Honestly I’m bracing for people complaining that she’s just as bad as men (being pushy) but I really enjoyed the switch up here - Harry trying to ignore her advances and YN not taking no for an answer 😂

Love your feedback! Thank you 😘

Xoxo

DILF | older!harry

MAIN MASTERLIST

Summary: Y/n meets an older man at a bar and she's not taking no for an answer. Harry likes her persistence.

A/N: This was requested + this! Also, please think before you judge Y/n. She is very bold and confident in this. Maybe even a little pushy but Harry likes it (even if at first he doesn't give that impression). Also he's single so this isn't cheatrry!

Word Count: 6,580

Warning: age gap, smut, alcohol consumption (light)

. .

"That one. Total dilf. He looks grumpy. Bet you can't crack him."

Y/n laughed at her friend and looked down at her red-painted nails before narrowing her gaze on the attractive older man who was seated at the corner of the bar alone. He was nursing a whisky and he did look rather sullen. Unapproachable even.

"Why him?"

"Because he's hot. And I'm curious to see if you can get him to smile at least," Warren raised her brows, "I dare you."

Y/n tilted her head and assessed him. He was nice and big, taking up a decent amount of space at the bar, broad shoulders and back hunched as he leaned his muscular forearms on the wood of the bar top. Meaty hands placed on either side of his lowball glass. Thick brown waves on top of his head with a bit of silver coming in at the temples. But the handsome features on his face really set him apart. His granite jawline gave way to stubble that stretched over his skin and shaded in the spaces around his pink lips.

If she could "crack" him she wasn't sure she'd want just a smile. He looked yummy enough to eat.

Drinking down the last of her martini she pointed at Warren and then Tara, "Fine. Give me twenty minutes and I'll have him eating from the palm of my hand."

Tara laughed, "If you say so…"

She placed her heeled feet down on the floor and brushed her hands over her dress, "Oh, I do say so. Just watch and learn, ladies."

Y/n wasn't quite that confident, but she wasn't about to say no to dare. And she could hold her own when it came to flirting. She liked getting a little attention and if she could garner this one's interest it might be fun.

She sauntered up to the bar behind the man and noticed the way his t-shirt stretched over his lats and tapered loosely down at his waist. The guy was fit. And lucky her, there was an open stool next to him.

Sliding onto the seat she waved at the bartender to order another drink. She'd need all the courage she could get, in whatever form she could get it.

Tapping her long nails on the lacquered wood she felt nerves thrumming through veins before turning toward the man finally. He hadn't seemed to take note of her yet, which honestly was unusual in most cases. Maybe she thought too highly of herself but men tended to notice her right away. She appreciated the challenge, though.

Reaching her hand into his space to greet him, she pushed down her nerves to sound steady as she spoke, "I'm Y/n."

She watched his brow furrow as he turned to look at her hand and then up at her eyes, his expression, which she expected would soften once he looked at her, was unamused. A single light overhead lit the tops of their heads as a shadow cast over the side of his face and he didn't make a move to shake her hand, "And I'm old enough to be your dad."

A surprised scoff fell from her lips as she moved her hand away from him. She wiggled in her seat and crossed her leg over her thigh toward him, gulping down the initial rejection with as much grace as she could muster, "I think you're jumping to conclusions about my intentions. But so what if you're older than me? I don't mind. We're both adults, right?"

An unimpressed grunt rumbled from his throat before he took another sip of his whisky and he looked away from her toward the TV that hung not far away from where they sat.

The bartender placed her olive martini down on the bar in front of her, "It'll be on Y/n Y/l/n. I already have an open tab."

A sip of the salty drink felt warm down her throat. So he was going to be a bit tough to crack. She turned to look at her friends who were grinning in her direction.

Straightening her back to feel more confident she tried again, "So you're not gonna tell me your name even?"

Without looking at her, he licked his lips and ticked his jaw, "Y/n, I think it's past your bedtime."

She smiled at that. He'd said her name, which meant he'd been listening, "My bedtime is whenever I say it is, not when some grouchy stranger says."

He puffed out an amused laugh through his nose, "I am a stranger. Which means you should be cautious, little girl. Your dad didn't teach you about things like that?" He turned to look down at her again, and that time she saw the soft green color of his eyes as the light hit his face just right.

But now she was really determined. She smiled brightly at him and let her eyes coast over his tattooed arm and then back up to his face, "Are you telling me you're dangerous?"

He still didn't smile as he shook his head like he was surprised by her gall, "Do your parents know what you're up to tonight?"

"I'm 24. Graduated from college, live on my own, pay my bills, have a full-time job. You seem to be awfully worried about my parents. I can take care of myself just fine."

Just then another person sat down next to the man Y/n was trying to whittle away at. He poked his elbow at him, "Who's this?"

"Don't know. Someone who's about to go back to her table with her little girlfriends."

Biting her lip she traced the rim of her martini glass with her fingertip, keeping her eyes set on the handsome tattooed one, "Not even a smile. Just one? Please?"

"Like I already said, I'm way too old for you."

The other man leaned over and reached to tap Y/n's shoulder, "Hey. Forget about Harry, here. You can bring me home with you if you're looking for a daddy tonight."

She frowned and looked him up and down to asses. He was late 40s perhaps, wearing a local band t-shirt, ripped jeans, and a backward cap to make himself appear a little more youthful. "No thanks. You'd know if I was interested in you."

Harry bit the inside of his cheek to stop himself from smiling at her retort. She was definitely too young but he liked her spunk.

"Now, Harry…" she said his name slowly as she leaned a little closer, "I've got your name thanks to your friend. Can I have a smile?"

"Why?" He stared down at her, the caress of his gaze felt infinite and she found her skin convecting in its wake. He might be hard to crack but this one would be worth it, she determined.

She sighed and slid her finger dangerously close to his wrist as he looked down at her nail and watched her trail it near his arm, "I just hoped to see you smile is all. Too handsome to have such a sour scowl on your face."

"And you're hardly old enough to be so confident to walk up to a strange man at a bar."

She laughed and tilted her head, "You planning on doing something bad to me, Harry?"

And that. That pulled a reaction out of him that spread over his features slowly as he shook his head in disbelief, "Darlin', you wouldn't be able to handle me."

Her eyes widened slightly. Now she was definitely not giving up. Y/n wasn't one to fail and Harry might be making her work hard for it but she couldn't imagine it wouldn't be worth it in the end.

"Is that a challenge or something?" She softly scraped her nail over his tattooed wrist and Harry watched her red nail work over his skin.

His resolve was fading fast. She could tell he wasn't going to keep denying her. And why should he? If he was single, which he appeared to be, what was the harm in having a little fun with someone younger? Y/n didn't mind. And he certainly shouldn't either.

"If it were a challenge you'd know it. Lots of other guys here, Y/n. Go enjoy your night with someone closer to your own age."

She sighed in annoyance. But he hadn't moved his arm away from her and she was going to take that as a sign.

Dragging the toe of her shoe into his shin she grinned, "I don't want to enjoy my night with someone my own age. Not tonight anyway. I think you've convinced me that I need to test out this theory of yours. That you think I can't handle you. Cause I bet I can."

With his eyes piercing into hers, he took another sip of his drink. She thought she might have just convinced him to give her a smile at the very least because it looked like he was weighing his options. And if she could get him to smile she might have luck with the rest.

He tilted his chin upward for a moment, eyes aimed at the ceiling like he was calling on a higher power for strength, "Go back to your friends, Y/n. Any other man here would love to have your company."

"But you wouldn't love to have my company?"

"I mean… I'm still here," the other man raised his hand and leaned into Harry, "Honey we could have so much fun. Any man who'd turn you down is either battin' for the other team or more likely," he chuckled and pushed his shoulder into Harry's teasingly, "He can't get it up anymore."

Y/n's mouth dropped open at that and Harry turned to look at the man. She wished she could see the look on his face, "Sit the fuck back down, John. She already told you she's not interested in you."

"Yeah, and you're not interested in her so what's it matter to you? Look at her, Harry. Practically begging you. Young and bubbly… Tight—"

Harry's hand covered John's throat as he pushed him away, nearly making his stool topple over, "Get the fuck outta here. You had too much whisky tonight."

"Aww… come on Harry… I was just jokin'!"

She watched as he stood from his stool and looked down at John, "And you thought that was funny? You like making jokes about women like that?"

The man put his hands up in surrender, "I'm out. Here…" he threw a wad of cash on the bar top before he moved past Harry and then looked at Y/n, "My apologies if I offended you."

They watched as John left the bar quickly and then Harry sat back down before he waved at the bartender and signaled for the check, "Just the one whisky neat."

"You're leaving already? Night's still young, Harry."

He sucked at his teeth as he scraped his gaze over her face and down to her cleavage. She smiled when she watched the path his eyes had taken.

The bartender handed him the bill and Harry leaned over to pull his wallet from his back pocket.

She scooted closer to him, "You headed home?"

He nodded, but not necessarily in answer to her question, it was more of an appraisal kind of nod. He was still silent as he pulled cash out of his wallet.

"Thanks for that, by the way. I'm sure John's a nice guy and all but he's not really my type. And I'm sure he was wrong about you."

That got his attention. Harry flicked his gaze back to hers, "Wrong about me?"

She smiled, "The part where he said you couldn't get it up. You're not that old. I'm sure you still can. Right?"

He clenched his jaw and breathed out of his nostrils like he couldn't believe she'd asked him such a thing. He handed the bartender his cash with a nod before he stood up from his stool.

"Huh. Since you're so quiet about it maybe he was right," she goaded, pressing her lips together to flatten her smile as she looked up at him through her lashes.

Harry placed a palm down on the bar top next to her hand and leaned over her, "You're out of your depth here, Y/n."

"Now, you don't really know that do you? Just because I'm younger than you doesn't mean I don't know what I'm doing."

"You're awfully pushy. Not used to hearing no, are you?"

Y/n watched as the edge of his mouth lifted in amusement and she widened her eyes and pointed, "You're almost smiling."

He shook his head and looked around the bar before pinning his gaze back to hers, "I hope you enjoy the rest of your night. But your luck has run out with me, princess."

Harry stood to his full height and Y/n decided to try one last time, "So it's true then. What he said."

He stopped and turned to look back at her, a slow burning heat behind his gaze, "Couldn't be further from the truth."

She smiled and slid off her stool to stand in front of him. His height was impressive, "Prove it."

The line of his jaw hardened, turning his cheekbones into slashes of tension. His eyes simmered as he weighed his options. Finally, a hint of a smile stretched over his mouth. A small one, but still.

"I don't need to prove anything to silly little girls."

"Good thing I'm not a silly little girl. I'm a grown woman, Harry."

Y/n knew she was pushing it. She'd never needed to throw herself at any man before. But because of that, she wasn't used to rejection either. Maybe it was a good lesson for her ego. She knew her big fault was how entitled she could act sometimes. But that was partly thanks to how she was raised. It's better to act like a man to get what you want in life, her dad told her. And so far, that had been true. Some women balked at her confidence and her bold attitude. She wasn't demure or sweet enough. And men would often refer to her as a bitch or say that she was trying too hard.

She'd work on her ego another time. But right now? She was focused on winning this battle.

"What do you want with someone like me anyway? Hm? I'm old, Y/n. What's in it for you?"

Blinking her eyes she shook her head, "You're not old, first of all. Secondly, you're really attractive. It doesn't need to go much deeper than that, does it? I just think you're handsome. And I do kind of like a challenge."

"I can see that you like a challenge. It's the only reason I haven't walked out that door yet. Kind of relentless."

She smiled, "So it's working?"

Another half-smile worked its way up his mouth as he laughed in disbelief, "Are you surprised that it is?"

His pupils coasted over her figure and then back up to her face. The warmth of his gaze singed her skin like an open flame.

"I guess I just didn't know how difficult it'd be with you."

He licked his lips, "Difficult. You have no idea. But looks like you're about to find out. Go tell your friends what's going on. Meet me out front."

Y/n watched him turn and walk away. She was shocked. For a minute she thought he wasn't going to go for it at all.

Shaking off the sudden surprise of having gotten to him she settled up with the bartender and then stopped at the table with her friends. They were just about to give her condolences for having oversold her ability but she interrupted. "He's waiting for me outside. Location is on. Don't wait up!"

Harry was leaning against a black car in the parking lot when she stepped out of the doors. The moment he saw her he pushed himself off the car and opened the passenger door for her.

It was going to be tricky to maintain the kind of confidence she'd been feigning with him up until then but there was no part of her that didn't want to find out what he could show her.

She watched as Harry sat down in the driver's seat and started up his car. He took up too much space in the seat. His big hand wrapped around the leather steering wheel while his other encased the shift stick. Even the way he drove was turning her on.

She was pleased that she'd wormed her way under his skin and that he'd given in. She'd try her best to make it worth his while. Reaching across the console she put her hand on his thigh and he glanced down quickly before setting his gaze back on the road.

Now, Harry had slept with younger women a couple of times. He generally preferred someone closer to his age because he liked the confidence and experience that came with age. Women in their 20s were often in a different stage of life and that was fine –normal even, but it just usually wasn't a match for him. Not sexually and not mentally.

But Y/n was unusually confident for being so young. Persistent. He liked it, he couldn't lie. Whether or not she really had much else going for her beyond confidence, he guessed he'd find out. Well, she was very cute too. She did have that in her favor.

And Y/n at least seemed like she knew what she wanted. It was flattering as well. Being approached by such a pretty young thing. He figured the moment he told her to go back to her friends she'd give up but she was just fiery enough that she wasn't deterred.

When she ran her nail over his wrist he knew he was screwed. She was just close enough that he could smell her perfume and then she nudged her shoe into his shin and all he could think about was that she really wanted to be shown a good time and if anyone could it was him.

Harry knew his way around a woman's body. They were all different and he liked finding all the buttons and things that made them purr. In his experience, though, the younger the woman, the less she knew her own body. He didn't know if Y/n was just talking a big game but he was about to find out.

He stayed quiet as she ran her hand down his thigh and he shifted as the car accelerated past the green light. He'd see if she'd do anything with her hand but maybe she'd just pet at him like a novelty toy. He didn't expect—

"This is okay?" She asked him, her tone sultry as she palmed at his crotch.

He licked his lips, "Have at it."

His cock fattened up nicely with not much effort on her part. Proof that he definitely could get it up. Plucking at his button she looked from his face to her fingers as she leaned further over the console to reach her hand into his open pants to help him with the awkward angle of his dick. He seemed to appreciate that as he shifted under her palm.

Rubbing over his heather grey briefs she peeled down the elastic band the slightest to get a peek. The dark shade of pink on his tip matched the muted raspberry of his lips. She slid the pad of her middle finger over the slit and he softly inhaled through his teeth.

She wouldn't be able to give him roadhead like she wanted. It was impossible with the stick shift in the way. But she could wrap her fingers around his shaft and feel him under her palm until they got wherever they were going.

"Mmm… It's so big, Harry. Knew you would be. Might be the biggest I've seen in person. Can't tell yet, though. Have to wait to see when we've got these off."

Harry pushed a laughed breath through his nose. She was a bold thing. Her assertiveness was a turn-on. He didn't like meek and shy. Not when it came to sex.

When she spit into her palm and smeared it down his length, the best she could, he parted his lips and stepped on the gas. She was already exceeding any expectations he had for her. Maybe she'd prove him wrong.

Her nail scraped the underside of him and she moaned, "Really want it in my mouth."

He gulped harshly and ticked his jaw, "Just be patient. I'll let you put it in your mouth soon enough."

"And where are we going? Your place?"

He nodded, "Just a few minutes away."

She squeezed around him and pulled upward slowly. She knew already, he was well above average and she was going to have to work to give him a proper blowy.

His house was a one story, the driveway at the front with a garage attached. He lifted his hand and pushed on a device that was clinging to his sun visor and the garage door began to open. There was a covered motorcycle along the back wall and then the garage door closed after he shut off the engine.

She moved her hand away and unbuckled herself as he got out. When she reached down to pick up her little purse she realized her panties were already wet. She grinned as she stepped out, adjusting her dress before closing the door, and then followed behind him as he led her into a dark hallway.

When he turned on the lights she took it all in. Hardwood floors led into a dining area and then a kitchen. Hung on the walls were photos of himself with two children and then more framed photos with just the kids.

"Do you have kids?"

"I do. Boy and a girl. 7 and 10."

"You're not married are you?"

He laughed, "If I were you'd have known. Wouldn't have been out in the first place if I had a wife waiting for me at home."

She nodded as he turned on the kitchen light and pulled out two glasses before filling them with water.

"Divorced?"

Handing her a glass he squinted, "Yes."

She took a sip. He was a man of few words she'd gathered. She looked around the kitchen. Wood cabinets, an outdated laminate countertop, stainless steel appliances. The space could use some updating but it was large and he had a big pantry.

Sitting the glass down on the counter she watched him closely. His pants were still unbuttoned. She eyed the space at his crotch as he placed his own glass down next to hers.

"It's not gonna suck itself."

She laughed and looked up at him. He had a genuine smile on his face that time. The first real smile she'd seen from him all night. A healthy row of clean teeth, a dimple…

"Hmm… I think you're right. Let's see what we've got…"

She moved in front of him and placed her hands on his pants to push them away but before she could inch them down he wrapped his meaty hand around the back of her neck and drew her into his chest. His mouth was warm and soft. His tongue tasted like the whisky he'd been drinking.

Letting go of his pants she held onto his biceps as he used his free hand to push her hips against his. Still nice and hard. He ran his tongue over her lips and she moaned into his mouth. He worked his warm lips down to her jaw and then he licked upward on her neck, the wet patch was cool on her skin from the air in the kitchen. He did it again and her knees almost gave out. She hadn't been licked like that before.

He kissed over her clavicle and then drew his tongue over her flesh. Her heart was thrumming quickly and she squeezed his strong arms when he rutted against her.

"You good at sucking cock, Y/n?" He pushed his nose against her jawline and the hot breath from his words scattered over the skin on her neck.

"I want to be," she spoke breathlessly, eyes fluttering closed as he mawed at her throat.

He parted from her neck and looked down at her, half-lidded gaze and spit-slicked lips, "Go on."

Instantly she dropped to her knees as her fingers worked deftly at pulling his pants down and then his underwear. She'd sucked a handful of dicks so she knew a couple of moves.

Getting her hand around his thick shaft proved to be a small challenge. To say he was thick… understatement. Long too. His tip was smooth, mushroomed with ridges along the length that she hoped she'd get to feel later on. His was the kind of cock that women dreamed of.

Looking up at him she licked her palm and used her spit to pump him slowly. Another glob over his tip for good measure. Then she pressed a kiss to the base of him, just over his sac, and screwed her eyes upward to watch his expression as she licked his balls, one side at a time. She wound her tongue all around to wet him before sucking at one side, pulling it into her mouth and he let out a ragged breath, his dark pupils spreading inky until the soft green had almost vanished.

He liked it.

She worked around the other side, sucking him in again and swirling her tongue softly underneath the tender bits. He gripped the counter behind himself.

Pulling off she straightened her back and licked upward, feeling every delicious thick ridge along his shaft until her tongue met his smooth crown. Laving every crevice of his tip, she dipped her tongue into his slit and then ran it under the frenulum before she wetted every inch of his glans.

Her mouth was watering when she parted her lips around him and flitted her gaze upward. He was watching her with a slack jaw as she took him a little deeper. He cradled the back of her head and moaned.

"Just suck the tip…."

She blinked up at him and pulled her lips just over the lip, swirling and suckling around him like he wanted.

"Fuck. Just like that." His hand at the back of her head was easy. He didn't push or pull. It was more like a pleased gesture as his fingertips flexed around her skull gently.

Y/n would have liked to have gone deeper. Wanted to show him her best work. But he seemed rather happy with what she was doing.

She bobbed a couple of times, only to slide her lips back to his tip. Her pace was slow when she began to stroke his length with a little twisting motion.

He was big. She knew she could take more but in a way, she was grateful that that was all he was asking for.

A groan fell from his chest and he bucked forward, his cock slipping down her tongue and she sucked, drawing more of him in as she moved her hands away.

"Goddamnit, you're good."

She took that as permission to go deeper. Relaxing her jaw she closed her eyes and held her breath, pushing down to her limit. She filled her throat with his cock the best she could and gurgled around his tip.

He coughed out a moan and then thumbed at her cheek, "Alright, that's good."

She pulled off of him. His heavy cock aimed right at her face when she sat back on her knees and looked up at him, "I can do better than that."

He laughed and put his hand out for her to take, helping her stand up, "I bet you can. Come on."

Harry kept her hand in his as he led her to his bedroom. It was just past the dark living space and he turned on a floor lamp on the opposite side of the room from the bed. When he turned back toward her he cupped her face and kissed her again.

She pressed her hand into his warm, hard chest and he reached around the back of her dress to pull the zipper downward, his fingers dragging down her skin as he went. His touch sent a tremor down her spine as continued kissing her wetly.

He stepped back, helping her out of her dress until it fell to the floor. His eyes raked over her body and he smoothed his hands over her hips and up to her bra-covered breasts. He stepped in closer, walking her backward toward his bed. He put his hands back on her hips and nudged her to sit before he reached down to lift her leg up by her calf, removing her heels, one at a time.

Y/n's thong was drenched. She stared at him while he placed her shoes side by side at the foot of the bed and then he placed his big palms on her thighs, pushing her legs open, "Lie back."

She let her back hit the mattress as Harry got to his knees on the floor. An arm reached under her thigh as he spread her apart and then she felt her panties being pulled at until her her wet pusslips were right in his face. He groaned and felt a hand slide up the inside of her thigh. He pressed his mouth over her mons and looked up at her before he opened his mouth wide and drew his tongue through her crease making her gasp.

"Get your bra off."

She pushed herself up slightly and worked at the clasp of her bra between moans as Harry continued licking at her pussy. When she pulled her arm through the flimsy material he lifted his head and reached around her back, pulling her closer to the edge of the bed and he sucked a nipple into his mouth.

"Oh, fuck!"

Y/n's finger and her long nails pushed into Harry's hair and scraped at his scalp as he licked and pulled at each nipple. He buried his face between her tits and let out a low sound, like he was murmuring something to her but only her breasts were allowed to hear it.

When he sunk back down he pushed at her so she'd lie back and he started in on her clit, one hand holding her panties to the side as he devoured her glistening cunt.

She kept feeling like she was going to slide off the edge of the bed but Harry's grip on her kept her still. His tongue and his lips were magic as he drew her to her end. She yanked at his hair and babbled his name on repeat as her spine bowed off the bed when she came.

Her chest was still rising and falling heavy when she felt her body being pushed upward. She popped her eyes open and watched him roll a condom over his shaft before he kneed back up onto the bed next to her. He was stark naked. His body was insane. Thick muscle and masculine everything. Tattoos scatter over his arms and chest.

Fuck, she muttered under her breath.

"Flip over, for me," his deep voice was husky as he motioned toward her to move.

She rolled to her stomach and she felt his fingers slide between the band of her panties and her hips as he pulled them down her legs.

"Ass up a little. I want to see all of you, Y/n."

She grinned and turned to look at him over her shoulder as she lifted her hips and spread her thighs. His lips were parted as he grabbed her ass and squeezed, making her cheeks spread apart. He inhaled sharply through his teeth and then dipped in, kissing her pussy from behind before licking upward over her ass.

She squealed quietly and bit her lip, still watching him behind her as he lifted, a lopsided grin on his face. He gazed at her as he fisted the base of his cock and slid the head up and down her soaked folds before he tipped his hips to push in just the tip.

"Gorgeous. Gonna look even better wrapped around cock. You like anal?"

"Never tried it."

He licked his lips and pressed his lips together as he looked at the spot where his dick was pressed against her cunt, "Figured. S'alright. Pussy's my favorite anyway."

"We could try… if you want."

He looked back into her eyes, a cocky smile on his face, "Your little hole would need to be trained. And that takes time. So, there will be no anal tonight. Not gonna try and hurt you. But that's a cute thought."

He canted his hips inward, eyes on hers and her mouth dropped open when she felt her entrance splitting open for him. She was tight, but so slick, it only took a few slow thrusts until he was buried in with a low grunt. He pulled back and then pushed his entire length into the hilt.

"Fuck—fuck!" She cried and stuffed her face into the blankets.

"Too much?"

"No! It's so good. You're just so big…" She began to send her hips back against him and Harry slowly fucked in to match her pace. His eyes were everywhere. On her puss getting split open on his cock, the curve of her lower back, the swell of her ass.

He just knew she'd look so sweet with her ass stuffed too, but good things like that couldn't be rushed which was a shame.

Every thrust was gushy wet. Y/n bubbled out small moans every time his dick brushed deep into her guts. It was better than she imagined. The way he filled her to the brim was going to turn into an addiction. She'd never slept with any man that had her wanting seconds before they'd even finished.

"Oh my god…" she mewled into the comforter.

"Fuck, I know, baby…"

She fit him like a glove, it was perfect. He went in a little faster, balls thudding against her skin rhythmically making her bounce forward as she spread around his girth. When he ground in she arched her back deeply and let out a soft groan, her hands fisted at the blanket and Harry reached around and smeared his fingertips over her clit.

It had her panting and pushing into him feverishly. She'd needed the friction on her throbbing button and he'd found it easily, thick, rough fingerprints slicking back and forth as he rutted in and in. It sent electrical sparks over her limbs.

"Like that? Needs her clit touched? Shit baby, act like you've never been touched by a man right here before…" he plucked at her like he was playing the guitar and she began to fade, her moans getting caught in her chest.

He could feel her walls tightening around him as he drove in deep.

"Fuck, Harry— fuck!"

He grinned as he watched her shudder, "Give it up, Y/n. There you go…"

She began to pulse around him, a constant stream of nonsense falling from her lips as he stroked against her channel and pushed deep into her tummy, his fingers still working her clit with ease.

Just as her body had tipped and oxygen returned to her lungs he pulled out and she felt him taking her hips and turning her around to her back. Harry grabbed her ankles and lifted until each was settled over his shoulders and pushed back inside of her, cock drilling down to her core making her teeth chatter at the way he split her down the middle.

Harry leaned over her, cock buried deep as she watched her pretty face twist up with pleasure. Plapping into her, her tits wobbled as his balls tightened against his body. The harder he plunged in, the more her legs shook. Soon, her ankles had slipped down and her feet hit the mattress as he continued drilling into her. His face was flushed hot, lips parted, muscles tensed.

Reaching up to his neck she smoothed her fingers over his warm skin and he lowered his chest down to hers and kissed her. That filthy tongue ran over her lips and he sloppily sipped at her between sucking at her lips. Her brain had turned to jelly.

She felt his hand on her outer thigh squeezing and brushing as he fucked down into her. "Mmm… fuck, Y/n, m'gonna come…"

He trembled over her, thick thighs pressed down and flexed as he rutted in and in and in, and then… he stilled. A deep, guttural moan vibrated through his chest down into hers.

She sighed when she felt him throbbing, pumping into his condom. Her fingers caressed the muscles over his back and she gasped when he bucked in harshly, once more as he emptied the last of his come into the rubber wrapped around his cock.

He slowed his kisses until they were lazy little pecks and then he looked down at her, his chest heaving. She was already grinning up at him.

"What?"

She blinked her eyes, "That was fun."

He puffed out a breath, "I guess that's a good way to describe it."

Harry was a gentleman as he pulled out slowly and helped her off the bed and led her to his bathroom. He helped her clean up and listened to her tell him about her job —just reminding him that she was an adult after he commented on her being so young again.

When she picked her dress up off the floor and started to step into it, Harry frowned, "What are you doing?"

She stopped and raised her brows. "Getting dressed. Was gonna call an Uber. I'm sure you don't want a stranger in your house all night," she laughed.

Harry pulled at her hand, making her drop her dress, "What kind of men have you been hanging out with that let you leave in an Uber at 2 am? You'll stay here."

She opened her mouth and then closed it in surprise before tilting her head in confusion, "Really? I just assumed—"

"You'll stay the night here. There's no way in hell you're getting an Uber at this time of night. It's dangerous."

She grinned and shrugged, "Well then… can I have a shirt or something to sleep in?"

He placed his warm hands on her hips, "You can have a t-shirt if you like. I prefer to sleep naked myself."

"Oh yeah? I usually do too as a matter of fact."

He held her out in his arms and eyed her naked frame, "Looks like we're both good to go then. We'll get you sorted in the morning. I'll give you a ride home then."

"I think you just want to keep me here with you," she chuckled.

Harry shook his head and released her hips before he popped her on the bottom with his palm. She bleated out a laugh.

"Get your ass in bed before I change my mind."

"Yes, sir."

. .

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[gurugirl]

https://www.tumblr.com/gurugirl/770501597803462656/theres-gonna-be-a-halo-hovering-over-harrys-cock?source=share

I just know you're going to give us something so nasty and hot after all this waiting. Their chemistry and the tension between them is unmatched. I used to think of you as the queen of smut (you still are) but after subscribing to your patreon I think of you as the queen of angst and slow burn too.

And I don't mean this as something bad to your old stuff on tumblr because I still read all your old fic for my comfort fic but your writing has improved x100 since you started your patreon. You could genuinely convert your stories for mainstream publishing and be very successful.

Okay I got off track for a second. Better Man is so good and I can't wait for more of it. The smut will probably put me in my grave.

Ohh ha haha! Yes, the plan is for the smut (when we get there) is to have it be unforgettable! lol

And omg thank you!!!!!!!! 🥰 I'm aware of the improvements, not to toot my own horn, and while I still doubt that I'd be successful as a published author I am proud of some of my work :) This is really kind of you to say, anon. Gonna be thinking about this all day 💕

Thank you 🥰

xoxo

[gurugirl]

DILF | older!harry

MAIN MASTERLIST

Summary: Y/n meets an older man at a bar and she's not taking no for an answer. Harry likes her persistence.

A/N: This was requested + this! Also, please think before you judge Y/n. She is very bold and confident in this. Maybe even a little pushy but Harry likes it (even if at first he doesn't give that impression). Also he's single so this isn't cheatrry!

Word Count: 6,580

Warning: age gap, smut, alcohol consumption (light)

. .

"That one. Total dilf. He looks grumpy. Bet you can't crack him."

Y/n laughed at her friend and looked down at her red-painted nails before narrowing her gaze on the attractive older man who was seated at the corner of the bar alone. He was nursing a whisky and he did look rather sullen. Unapproachable even.

"Why him?"

"Because he's hot. And I'm curious to see if you can get him to smile at least," Warren raised her brows, "I dare you."

Y/n tilted her head and assessed him. He was nice and big, taking up a decent amount of space at the bar, broad shoulders and back hunched as he leaned his muscular forearms on the wood of the bar top. Meaty hands placed on either side of his lowball glass. Thick brown waves on top of his head with a bit of silver coming in at the temples. But the handsome features on his face really set him apart. His granite jawline gave way to stubble that stretched over his skin and shaded in the spaces around his pink lips.

If she could "crack" him she wasn't sure she'd want just a smile. He looked yummy enough to eat.

Drinking down the last of her martini she pointed at Warren and then Tara, "Fine. Give me twenty minutes and I'll have him eating from the palm of my hand."

Tara laughed, "If you say so…"

She placed her heeled feet down on the floor and brushed her hands over her dress, "Oh, I do say so. Just watch and learn, ladies."

Y/n wasn't quite that confident, but she wasn't about to say no to dare. And she could hold her own when it came to flirting. She liked getting a little attention and if she could garner this one's interest it might be fun.

She sauntered up to the bar behind the man and noticed the way his t-shirt stretched over his lats and tapered loosely down at his waist. The guy was fit. And lucky her, there was an open stool next to him.

Sliding onto the seat she waved at the bartender to order another drink. She'd need all the courage she could get, in whatever form she could get it.

Tapping her long nails on the lacquered wood she felt nerves thrumming through veins before turning toward the man finally. He hadn't seemed to take note of her yet, which honestly was unusual in most cases. Maybe she thought too highly of herself but men tended to notice her right away. She appreciated the challenge, though.

Reaching her hand into his space to greet him, she pushed down her nerves to sound steady as she spoke, "I'm Y/n."

She watched his brow furrow as he turned to look at her hand and then up at her eyes, his expression, which she expected would soften once he looked at her, was unamused. A single light overhead lit the tops of their heads as a shadow cast over the side of his face and he didn't make a move to shake her hand, "And I'm old enough to be your dad."

A surprised scoff fell from her lips as she moved her hand away from him. She wiggled in her seat and crossed her leg over her thigh toward him, gulping down the initial rejection with as much grace as she could muster, "I think you're jumping to conclusions about my intentions. But so what if you're older than me? I don't mind. We're both adults, right?"

An unimpressed grunt rumbled from his throat before he took another sip of his whisky and he looked away from her toward the TV that hung not far away from where they sat.

The bartender placed her olive martini down on the bar in front of her, "It'll be on Y/n Y/l/n. I already have an open tab."

A sip of the salty drink felt warm down her throat. So he was going to be a bit tough to crack. She turned to look at her friends who were grinning in her direction.

Straightening her back to feel more confident she tried again, "So you're not gonna tell me your name even?"

Without looking at her, he licked his lips and ticked his jaw, "Y/n, I think it's past your bedtime."

She smiled at that. He'd said her name, which meant he'd been listening, "My bedtime is whenever I say it is, not when some grouchy stranger says."

He puffed out an amused laugh through his nose, "I am a stranger. Which means you should be cautious, little girl. Your dad didn't teach you about things like that?" He turned to look down at her again, and that time she saw the soft green color of his eyes as the light hit his face just right.

But now she was really determined. She smiled brightly at him and let her eyes coast over his tattooed arm and then back up to his face, "Are you telling me you're dangerous?"

He still didn't smile as he shook his head like he was surprised by her gall, "Do your parents know what you're up to tonight?"

"I'm 24. Graduated from college, live on my own, pay my bills, have a full-time job. You seem to be awfully worried about my parents. I can take care of myself just fine."

Just then another person sat down next to the man Y/n was trying to whittle away at. He poked his elbow at him, "Who's this?"

"Don't know. Someone who's about to go back to her table with her little girlfriends."

Biting her lip she traced the rim of her martini glass with her fingertip, keeping her eyes set on the handsome tattooed one, "Not even a smile. Just one? Please?"

"Like I already said, I'm way too old for you."

The other man leaned over and reached to tap Y/n's shoulder, "Hey. Forget about Harry, here. You can bring me home with you if you're looking for a daddy tonight."

She frowned and looked him up and down to asses. He was late 40s perhaps, wearing a local band t-shirt, ripped jeans, and a backward cap to make himself appear a little more youthful. "No thanks. You'd know if I was interested in you."

Harry bit the inside of his cheek to stop himself from smiling at her retort. She was definitely too young but he liked her spunk.

"Now, Harry…" she said his name slowly as she leaned a little closer, "I've got your name thanks to your friend. Can I have a smile?"

"Why?" He stared down at her, the caress of his gaze felt infinite and she found her skin convecting in its wake. He might be hard to crack but this one would be worth it, she determined.

She sighed and slid her finger dangerously close to his wrist as he looked down at her nail and watched her trail it near his arm, "I just hoped to see you smile is all. Too handsome to have such a sour scowl on your face."

"And you're hardly old enough to be so confident to walk up to a strange man at a bar."

She laughed and tilted her head, "You planning on doing something bad to me, Harry?"

And that. That pulled a reaction out of him that spread over his features slowly as he shook his head in disbelief, "Darlin', you wouldn't be able to handle me."

Her eyes widened slightly. Now she was definitely not giving up. Y/n wasn't one to fail and Harry might be making her work hard for it but she couldn't imagine it wouldn't be worth it in the end.

"Is that a challenge or something?" She softly scraped her nail over his tattooed wrist and Harry watched her red nail work over his skin.

His resolve was fading fast. She could tell he wasn't going to keep denying her. And why should he? If he was single, which he appeared to be, what was the harm in having a little fun with someone younger? Y/n didn't mind. And he certainly shouldn't either.

"If it were a challenge you'd know it. Lots of other guys here, Y/n. Go enjoy your night with someone closer to your own age."

She sighed in annoyance. But he hadn't moved his arm away from her and she was going to take that as a sign.

Dragging the toe of her shoe into his shin she grinned, "I don't want to enjoy my night with someone my own age. Not tonight anyway. I think you've convinced me that I need to test out this theory of yours. That you think I can't handle you. Cause I bet I can."

With his eyes piercing into hers, he took another sip of his drink. She thought she might have just convinced him to give her a smile at the very least because it looked like he was weighing his options. And if she could get him to smile she might have luck with the rest.

He tilted his chin upward for a moment, eyes aimed at the ceiling like he was calling on a higher power for strength, "Go back to your friends, Y/n. Any other man here would love to have your company."

"But you wouldn't love to have my company?"

"I mean… I'm still here," the other man raised his hand and leaned into Harry, "Honey we could have so much fun. Any man who'd turn you down is either battin' for the other team or more likely," he chuckled and pushed his shoulder into Harry's teasingly, "He can't get it up anymore."

Y/n's mouth dropped open at that and Harry turned to look at the man. She wished she could see the look on his face, "Sit the fuck back down, John. She already told you she's not interested in you."

"Yeah, and you're not interested in her so what's it matter to you? Look at her, Harry. Practically begging you. Young and bubbly… Tight—"

Harry's hand covered John's throat as he pushed him away, nearly making his stool topple over, "Get the fuck outta here. You had too much whisky tonight."

"Aww… come on Harry… I was just jokin'!"

She watched as he stood from his stool and looked down at John, "And you thought that was funny? You like making jokes about women like that?"

The man put his hands up in surrender, "I'm out. Here…" he threw a wad of cash on the bar top before he moved past Harry and then looked at Y/n, "My apologies if I offended you."

They watched as John left the bar quickly and then Harry sat back down before he waved at the bartender and signaled for the check, "Just the one whisky neat."

"You're leaving already? Night's still young, Harry."

He sucked at his teeth as he scraped his gaze over her face and down to her cleavage. She smiled when she watched the path his eyes had taken.

The bartender handed him the bill and Harry leaned over to pull his wallet from his back pocket.

She scooted closer to him, "You headed home?"

He nodded, but not necessarily in answer to her question, it was more of an appraisal kind of nod. He was still silent as he pulled cash out of his wallet.

"Thanks for that, by the way. I'm sure John's a nice guy and all but he's not really my type. And I'm sure he was wrong about you."

That got his attention. Harry flicked his gaze back to hers, "Wrong about me?"

She smiled, "The part where he said you couldn't get it up. You're not that old. I'm sure you still can. Right?"

He clenched his jaw and breathed out of his nostrils like he couldn't believe she'd asked him such a thing. He handed the bartender his cash with a nod before he stood up from his stool.

"Huh. Since you're so quiet about it maybe he was right," she goaded, pressing her lips together to flatten her smile as she looked up at him through her lashes.

Harry placed a palm down on the bar top next to her hand and leaned over her, "You're out of your depth here, Y/n."

"Now, you don't really know that do you? Just because I'm younger than you doesn't mean I don't know what I'm doing."

"You're awfully pushy. Not used to hearing no, are you?"

Y/n watched as the edge of his mouth lifted in amusement and she widened her eyes and pointed, "You're almost smiling."

He shook his head and looked around the bar before pinning his gaze back to hers, "I hope you enjoy the rest of your night. But your luck has run out with me, princess."

Harry stood to his full height and Y/n decided to try one last time, "So it's true then. What he said."

He stopped and turned to look back at her, a slow burning heat behind his gaze, "Couldn't be further from the truth."

She smiled and slid off her stool to stand in front of him. His height was impressive, "Prove it."

The line of his jaw hardened, turning his cheekbones into slashes of tension. His eyes simmered as he weighed his options. Finally, a hint of a smile stretched over his mouth. A small one, but still.

"I don't need to prove anything to silly little girls."

"Good thing I'm not a silly little girl. I'm a grown woman, Harry."

Y/n knew she was pushing it. She'd never needed to throw herself at any man before. But because of that, she wasn't used to rejection either. Maybe it was a good lesson for her ego. She knew her big fault was how entitled she could act sometimes. But that was partly thanks to how she was raised. It's better to act like a man to get what you want in life, her dad told her. And so far, that had been true. Some women balked at her confidence and her bold attitude. She wasn't demure or sweet enough. And men would often refer to her as a bitch or say that she was trying too hard.

She'd work on her ego another time. But right now? She was focused on winning this battle.

"What do you want with someone like me anyway? Hm? I'm old, Y/n. What's in it for you?"

Blinking her eyes she shook her head, "You're not old, first of all. Secondly, you're really attractive. It doesn't need to go much deeper than that, does it? I just think you're handsome. And I do kind of like a challenge."

"I can see that you like a challenge. It's the only reason I haven't walked out that door yet. Kind of relentless."

She smiled, "So it's working?"

Another half-smile worked its way up his mouth as he laughed in disbelief, "Are you surprised that it is?"

His pupils coasted over her figure and then back up to her face. The warmth of his gaze singed her skin like an open flame.

"I guess I just didn't know how difficult it'd be with you."

He licked his lips, "Difficult. You have no idea. But looks like you're about to find out. Go tell your friends what's going on. Meet me out front."

Y/n watched him turn and walk away. She was shocked. For a minute she thought he wasn't going to go for it at all.

Shaking off the sudden surprise of having gotten to him she settled up with the bartender and then stopped at the table with her friends. They were just about to give her condolences for having oversold her ability but she interrupted. "He's waiting for me outside. Location is on. Don't wait up!"

Harry was leaning against a black car in the parking lot when she stepped out of the doors. The moment he saw her he pushed himself off the car and opened the passenger door for her.

It was going to be tricky to maintain the kind of confidence she'd been feigning with him up until then but there was no part of her that didn't want to find out what he could show her.

She watched as Harry sat down in the driver's seat and started up his car. He took up too much space in the seat. His big hand wrapped around the leather steering wheel while his other encased the shift stick. Even the way he drove was turning her on.

She was pleased that she'd wormed her way under his skin and that he'd given in. She'd try her best to make it worth his while. Reaching across the console she put her hand on his thigh and he glanced down quickly before setting his gaze back on the road.

Now, Harry had slept with younger women a couple of times. He generally preferred someone closer to his age because he liked the confidence and experience that came with age. Women in their 20s were often in a different stage of life and that was fine –normal even, but it just usually wasn't a match for him. Not sexually and not mentally.

But Y/n was unusually confident for being so young. Persistent. He liked it, he couldn't lie. Whether or not she really had much else going for her beyond confidence, he guessed he'd find out. Well, she was very cute too. She did have that in her favor.

And Y/n at least seemed like she knew what she wanted. It was flattering as well. Being approached by such a pretty young thing. He figured the moment he told her to go back to her friends she'd give up but she was just fiery enough that she wasn't deterred.

When she ran her nail over his wrist he knew he was screwed. She was just close enough that he could smell her perfume and then she nudged her shoe into his shin and all he could think about was that she really wanted to be shown a good time and if anyone could it was him.

Harry knew his way around a woman's body. They were all different and he liked finding all the buttons and things that made them purr. In his experience, though, the younger the woman, the less she knew her own body. He didn't know if Y/n was just talking a big game but he was about to find out.

He stayed quiet as she ran her hand down his thigh and he shifted as the car accelerated past the green light. He'd see if she'd do anything with her hand but maybe she'd just pet at him like a novelty toy. He didn't expect—

"This is okay?" She asked him, her tone sultry as she palmed at his crotch.

He licked his lips, "Have at it."

His cock fattened up nicely with not much effort on her part. Proof that he definitely could get it up. Plucking at his button she looked from his face to her fingers as she leaned further over the console to reach her hand into his open pants to help him with the awkward angle of his dick. He seemed to appreciate that as he shifted under her palm.

Rubbing over his heather grey briefs she peeled down the elastic band the slightest to get a peek. The dark shade of pink on his tip matched the muted raspberry of his lips. She slid the pad of her middle finger over the slit and he softly inhaled through his teeth.

She wouldn't be able to give him roadhead like she wanted. It was impossible with the stick shift in the way. But she could wrap her fingers around his shaft and feel him under her palm until they got wherever they were going.

"Mmm… It's so big, Harry. Knew you would be. Might be the biggest I've seen in person. Can't tell yet, though. Have to wait to see when we've got these off."

Harry pushed a laughed breath through his nose. She was a bold thing. Her assertiveness was a turn-on. He didn't like meek and shy. Not when it came to sex.

When she spit into her palm and smeared it down his length, the best she could, he parted his lips and stepped on the gas. She was already exceeding any expectations he had for her. Maybe she'd prove him wrong.

Her nail scraped the underside of him and she moaned, "Really want it in my mouth."

He gulped harshly and ticked his jaw, "Just be patient. I'll let you put it in your mouth soon enough."

"And where are we going? Your place?"

He nodded, "Just a few minutes away."

She squeezed around him and pulled upward slowly. She knew already, he was well above average and she was going to have to work to give him a proper blowy.

His house was a one story, the driveway at the front with a garage attached. He lifted his hand and pushed on a device that was clinging to his sun visor and the garage door began to open. There was a covered motorcycle along the back wall and then the garage door closed after he shut off the engine.

She moved her hand away and unbuckled herself as he got out. When she reached down to pick up her little purse she realized her panties were already wet. She grinned as she stepped out, adjusting her dress before closing the door, and then followed behind him as he led her into a dark hallway.

When he turned on the lights she took it all in. Hardwood floors led into a dining area and then a kitchen. Hung on the walls were photos of himself with two children and then more framed photos with just the kids.

"Do you have kids?"

"I do. Boy and a girl. 7 and 10."

"You're not married are you?"

He laughed, "If I were you'd have known. Wouldn't have been out in the first place if I had a wife waiting for me at home."

She nodded as he turned on the kitchen light and pulled out two glasses before filling them with water.

"Divorced?"

Handing her a glass he squinted, "Yes."

She took a sip. He was a man of few words she'd gathered. She looked around the kitchen. Wood cabinets, an outdated laminate countertop, stainless steel appliances. The space could use some updating but it was large and he had a big pantry.

Sitting the glass down on the counter she watched him closely. His pants were still unbuttoned. She eyed the space at his crotch as he placed his own glass down next to hers.

"It's not gonna suck itself."

She laughed and looked up at him. He had a genuine smile on his face that time. The first real smile she'd seen from him all night. A healthy row of clean teeth, a dimple…

"Hmm… I think you're right. Let's see what we've got…"

She moved in front of him and placed her hands on his pants to push them away but before she could inch them down he wrapped his meaty hand around the back of her neck and drew her into his chest. His mouth was warm and soft. His tongue tasted like the whisky he'd been drinking.

Letting go of his pants she held onto his biceps as he used his free hand to push her hips against his. Still nice and hard. He ran his tongue over her lips and she moaned into his mouth. He worked his warm lips down to her jaw and then he licked upward on her neck, the wet patch was cool on her skin from the air in the kitchen. He did it again and her knees almost gave out. She hadn't been licked like that before.

He kissed over her clavicle and then drew his tongue over her flesh. Her heart was thrumming quickly and she squeezed his strong arms when he rutted against her.

"You good at sucking cock, Y/n?" He pushed his nose against her jawline and the hot breath from his words scattered over the skin on her neck.

"I want to be," she spoke breathlessly, eyes fluttering closed as he mawed at her throat.

He parted from her neck and looked down at her, half-lidded gaze and spit-slicked lips, "Go on."

Instantly she dropped to her knees as her fingers worked deftly at pulling his pants down and then his underwear. She'd sucked a handful of dicks so she knew a couple of moves.

Getting her hand around his thick shaft proved to be a small challenge. To say he was thick… understatement. Long too. His tip was smooth, mushroomed with ridges along the length that she hoped she'd get to feel later on. His was the kind of cock that women dreamed of.

Looking up at him she licked her palm and used her spit to pump him slowly. Another glob over his tip for good measure. Then she pressed a kiss to the base of him, just over his sac, and screwed her eyes upward to watch his expression as she licked his balls, one side at a time. She wound her tongue all around to wet him before sucking at one side, pulling it into her mouth and he let out a ragged breath, his dark pupils spreading inky until the soft green had almost vanished.

He liked it.

She worked around the other side, sucking him in again and swirling her tongue softly underneath the tender bits. He gripped the counter behind himself.

Pulling off she straightened her back and licked upward, feeling every delicious thick ridge along his shaft until her tongue met his smooth crown. Laving every crevice of his tip, she dipped her tongue into his slit and then ran it under the frenulum before she wetted every inch of his glans.

Her mouth was watering when she parted her lips around him and flitted her gaze upward. He was watching her with a slack jaw as she took him a little deeper. He cradled the back of her head and moaned.

"Just suck the tip…."

She blinked up at him and pulled her lips just over the lip, swirling and suckling around him like he wanted.

"Fuck. Just like that." His hand at the back of her head was easy. He didn't push or pull. It was more like a pleased gesture as his fingertips flexed around her skull gently.

Y/n would have liked to have gone deeper. Wanted to show him her best work. But he seemed rather happy with what she was doing.

She bobbed a couple of times, only to slide her lips back to his tip. Her pace was slow when she began to stroke his length with a little twisting motion.

He was big. She knew she could take more but in a way, she was grateful that that was all he was asking for.

A groan fell from his chest and he bucked forward, his cock slipping down her tongue and she sucked, drawing more of him in as she moved her hands away.

"Goddamnit, you're good."

She took that as permission to go deeper. Relaxing her jaw she closed her eyes and held her breath, pushing down to her limit. She filled her throat with his cock the best she could and gurgled around his tip.

He coughed out a moan and then thumbed at her cheek, "Alright, that's good."

She pulled off of him. His heavy cock aimed right at her face when she sat back on her knees and looked up at him, "I can do better than that."

He laughed and put his hand out for her to take, helping her stand up, "I bet you can. Come on."

Harry kept her hand in his as he led her to his bedroom. It was just past the dark living space and he turned on a floor lamp on the opposite side of the room from the bed. When he turned back toward her he cupped her face and kissed her again.

She pressed her hand into his warm, hard chest and he reached around the back of her dress to pull the zipper downward, his fingers dragging down her skin as he went. His touch sent a tremor down her spine as continued kissing her wetly.

He stepped back, helping her out of her dress until it fell to the floor. His eyes raked over her body and he smoothed his hands over her hips and up to her bra-covered breasts. He stepped in closer, walking her backward toward his bed. He put his hands back on her hips and nudged her to sit before he reached down to lift her leg up by her calf, removing her heels, one at a time.

Y/n's thong was drenched. She stared at him while he placed her shoes side by side at the foot of the bed and then he placed his big palms on her thighs, pushing her legs open, "Lie back."

She let her back hit the mattress as Harry got to his knees on the floor. An arm reached under her thigh as he spread her apart and then she felt her panties being pulled at until her her wet pusslips were right in his face. He groaned and felt a hand slide up the inside of her thigh. He pressed his mouth over her mons and looked up at her before he opened his mouth wide and drew his tongue through her crease making her gasp.

"Get your bra off."

She pushed herself up slightly and worked at the clasp of her bra between moans as Harry continued licking at her pussy. When she pulled her arm through the flimsy material he lifted his head and reached around her back, pulling her closer to the edge of the bed and he sucked a nipple into his mouth.

"Oh, fuck!"

Y/n's finger and her long nails pushed into Harry's hair and scraped at his scalp as he licked and pulled at each nipple. He buried his face between her tits and let out a low sound, like he was murmuring something to her but only her breasts were allowed to hear it.

When he sunk back down he pushed at her so she'd lie back and he started in on her clit, one hand holding her panties to the side as he devoured her glistening cunt.

She kept feeling like she was going to slide off the edge of the bed but Harry's grip on her kept her still. His tongue and his lips were magic as he drew her to her end. She yanked at his hair and babbled his name on repeat as her spine bowed off the bed when she came.

Her chest was still rising and falling heavy when she felt her body being pushed upward. She popped her eyes open and watched him roll a condom over his shaft before he kneed back up onto the bed next to her. He was stark naked. His body was insane. Thick muscle and masculine everything. Tattoos scatter over his arms and chest.

Fuck, she muttered under her breath.

"Flip over, for me," his deep voice was husky as he motioned toward her to move.

She rolled to her stomach and she felt his fingers slide between the band of her panties and her hips as he pulled them down her legs.

"Ass up a little. I want to see all of you, Y/n."

She grinned and turned to look at him over her shoulder as she lifted her hips and spread her thighs. His lips were parted as he grabbed her ass and squeezed, making her cheeks spread apart. He inhaled sharply through his teeth and then dipped in, kissing her pussy from behind before licking upward over her ass.

She squealed quietly and bit her lip, still watching him behind her as he lifted, a lopsided grin on his face. He gazed at her as he fisted the base of his cock and slid the head up and down her soaked folds before he tipped his hips to push in just the tip.

"Gorgeous. Gonna look even better wrapped around cock. You like anal?"

"Never tried it."

He licked his lips and pressed his lips together as he looked at the spot where his dick was pressed against her cunt, "Figured. S'alright. Pussy's my favorite anyway."

"We could try… if you want."

He looked back into her eyes, a cocky smile on his face, "Your little hole would need to be trained. And that takes time. So, there will be no anal tonight. Not gonna try and hurt you. But that's a cute thought."

He canted his hips inward, eyes on hers and her mouth dropped open when she felt her entrance splitting open for him. She was tight, but so slick, it only took a few slow thrusts until he was buried in with a low grunt. He pulled back and then pushed his entire length into the hilt.

"Fuck—fuck!" She cried and stuffed her face into the blankets.

"Too much?"

"No! It's so good. You're just so big…" She began to send her hips back against him and Harry slowly fucked in to match her pace. His eyes were everywhere. On her puss getting split open on his cock, the curve of her lower back, the swell of her ass.

He just knew she'd look so sweet with her ass stuffed too, but good things like that couldn't be rushed which was a shame.

Every thrust was gushy wet. Y/n bubbled out small moans every time his dick brushed deep into her guts. It was better than she imagined. The way he filled her to the brim was going to turn into an addiction. She'd never slept with any man that had her wanting seconds before they'd even finished.

"Oh my god…" she mewled into the comforter.

"Fuck, I know, baby…"

She fit him like a glove, it was perfect. He went in a little faster, balls thudding against her skin rhythmically making her bounce forward as she spread around his girth. When he ground in she arched her back deeply and let out a soft groan, her hands fisted at the blanket and Harry reached around and smeared his fingertips over her clit.

It had her panting and pushing into him feverishly. She'd needed the friction on her throbbing button and he'd found it easily, thick, rough fingerprints slicking back and forth as he rutted in and in. It sent electrical sparks over her limbs.

"Like that? Needs her clit touched? Shit baby, act like you've never been touched by a man right here before…" he plucked at her like he was playing the guitar and she began to fade, her moans getting caught in her chest.

He could feel her walls tightening around him as he drove in deep.

"Fuck, Harry— fuck!"

He grinned as he watched her shudder, "Give it up, Y/n. There you go…"

She began to pulse around him, a constant stream of nonsense falling from her lips as he stroked against her channel and pushed deep into her tummy, his fingers still working her clit with ease.

Just as her body had tipped and oxygen returned to her lungs he pulled out and she felt him taking her hips and turning her around to her back. Harry grabbed her ankles and lifted until each was settled over his shoulders and pushed back inside of her, cock drilling down to her core making her teeth chatter at the way he split her down the middle.

Harry leaned over her, cock buried deep as she watched her pretty face twist up with pleasure. Plapping into her, her tits wobbled as his balls tightened against his body. The harder he plunged in, the more her legs shook. Soon, her ankles had slipped down and her feet hit the mattress as he continued drilling into her. His face was flushed hot, lips parted, muscles tensed.

Reaching up to his neck she smoothed her fingers over his warm skin and he lowered his chest down to hers and kissed her. That filthy tongue ran over her lips and he sloppily sipped at her between sucking at her lips. Her brain had turned to jelly.

She felt his hand on her outer thigh squeezing and brushing as he fucked down into her. "Mmm… fuck, Y/n, m'gonna come…"

He trembled over her, thick thighs pressed down and flexed as he rutted in and in and in, and then… he stilled. A deep, guttural moan vibrated through his chest down into hers.

She sighed when she felt him throbbing, pumping into his condom. Her fingers caressed the muscles over his back and she gasped when he bucked in harshly, once more as he emptied the last of his come into the rubber wrapped around his cock.

He slowed his kisses until they were lazy little pecks and then he looked down at her, his chest heaving. She was already grinning up at him.

"What?"

She blinked her eyes, "That was fun."

He puffed out a breath, "I guess that's a good way to describe it."

Harry was a gentleman as he pulled out slowly and helped her off the bed and led her to his bathroom. He helped her clean up and listened to her tell him about her job —just reminding him that she was an adult after he commented on her being so young again.

When she picked her dress up off the floor and started to step into it, Harry frowned, "What are you doing?"

She stopped and raised her brows. "Getting dressed. Was gonna call an Uber. I'm sure you don't want a stranger in your house all night," she laughed.

Harry pulled at her hand, making her drop her dress, "What kind of men have you been hanging out with that let you leave in an Uber at 2 am? You'll stay here."

She opened her mouth and then closed it in surprise before tilting her head in confusion, "Really? I just assumed—"

"You'll stay the night here. There's no way in hell you're getting an Uber at this time of night. It's dangerous."

She grinned and shrugged, "Well then… can I have a shirt or something to sleep in?"

He placed his warm hands on her hips, "You can have a t-shirt if you like. I prefer to sleep naked myself."

"Oh yeah? I usually do too as a matter of fact."

He held her out in his arms and eyed her naked frame, "Looks like we're both good to go then. We'll get you sorted in the morning. I'll give you a ride home then."

"I think you just want to keep me here with you," she chuckled.

Harry shook his head and released her hips before he popped her on the bottom with his palm. She bleated out a laugh.

"Get your ass in bed before I change my mind."

"Yes, sir."

. .

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[gurugirl]

there’s gonna be a halo hovering over harry’s cock the first time y/n sees him naked

talking about a better man harry 🤭

YES. It's going to be a religious experience. Like angels singing in a choir, harps, life altering, absolute rapture...

Obviously. 😇 ✨🥖✨

Hahaha thank you hon!

xoxo

[gurugirl]

Haha thank you 💕

Xoxo

DILF | older!harry

MAIN MASTERLIST

Summary: Y/n meets an older man at a bar and she's not taking no for an answer. Harry likes her persistence.

A/N: This was requested + this! Also, please think before you judge Y/n. She is very bold and confident in this. Maybe even a little pushy but Harry likes it (even if at first he doesn't give that impression). Also he's single so this isn't cheatrry!

Word Count: 6,580

Warning: age gap, smut, alcohol consumption (light)

. .

"That one. Total dilf. He looks grumpy. Bet you can't crack him."

Y/n laughed at her friend and looked down at her red-painted nails before narrowing her gaze on the attractive older man who was seated at the corner of the bar alone. He was nursing a whisky and he did look rather sullen. Unapproachable even.

"Why him?"

"Because he's hot. And I'm curious to see if you can get him to smile at least," Warren raised her brows, "I dare you."

Y/n tilted her head and assessed him. He was nice and big, taking up a decent amount of space at the bar, broad shoulders and back hunched as he leaned his muscular forearms on the wood of the bar top. Meaty hands placed on either side of his lowball glass. Thick brown waves on top of his head with a bit of silver coming in at the temples. But the handsome features on his face really set him apart. His granite jawline gave way to stubble that stretched over his skin and shaded in the spaces around his pink lips.

If she could "crack" him she wasn't sure she'd want just a smile. He looked yummy enough to eat.

Drinking down the last of her martini she pointed at Warren and then Tara, "Fine. Give me twenty minutes and I'll have him eating from the palm of my hand."

Tara laughed, "If you say so…"

She placed her heeled feet down on the floor and brushed her hands over her dress, "Oh, I do say so. Just watch and learn, ladies."

Y/n wasn't quite that confident, but she wasn't about to say no to dare. And she could hold her own when it came to flirting. She liked getting a little attention and if she could garner this one's interest it might be fun.

She sauntered up to the bar behind the man and noticed the way his t-shirt stretched over his lats and tapered loosely down at his waist. The guy was fit. And lucky her, there was an open stool next to him.

Sliding onto the seat she waved at the bartender to order another drink. She'd need all the courage she could get, in whatever form she could get it.

Tapping her long nails on the lacquered wood she felt nerves thrumming through veins before turning toward the man finally. He hadn't seemed to take note of her yet, which honestly was unusual in most cases. Maybe she thought too highly of herself but men tended to notice her right away. She appreciated the challenge, though.

Reaching her hand into his space to greet him, she pushed down her nerves to sound steady as she spoke, "I'm Y/n."

She watched his brow furrow as he turned to look at her hand and then up at her eyes, his expression, which she expected would soften once he looked at her, was unamused. A single light overhead lit the tops of their heads as a shadow cast over the side of his face and he didn't make a move to shake her hand, "And I'm old enough to be your dad."

A surprised scoff fell from her lips as she moved her hand away from him. She wiggled in her seat and crossed her leg over her thigh toward him, gulping down the initial rejection with as much grace as she could muster, "I think you're jumping to conclusions about my intentions. But so what if you're older than me? I don't mind. We're both adults, right?"

An unimpressed grunt rumbled from his throat before he took another sip of his whisky and he looked away from her toward the TV that hung not far away from where they sat.

The bartender placed her olive martini down on the bar in front of her, "It'll be on Y/n Y/l/n. I already have an open tab."

A sip of the salty drink felt warm down her throat. So he was going to be a bit tough to crack. She turned to look at her friends who were grinning in her direction.

Straightening her back to feel more confident she tried again, "So you're not gonna tell me your name even?"

Without looking at her, he licked his lips and ticked his jaw, "Y/n, I think it's past your bedtime."

She smiled at that. He'd said her name, which meant he'd been listening, "My bedtime is whenever I say it is, not when some grouchy stranger says."

He puffed out an amused laugh through his nose, "I am a stranger. Which means you should be cautious, little girl. Your dad didn't teach you about things like that?" He turned to look down at her again, and that time she saw the soft green color of his eyes as the light hit his face just right.

But now she was really determined. She smiled brightly at him and let her eyes coast over his tattooed arm and then back up to his face, "Are you telling me you're dangerous?"

He still didn't smile as he shook his head like he was surprised by her gall, "Do your parents know what you're up to tonight?"

"I'm 24. Graduated from college, live on my own, pay my bills, have a full-time job. You seem to be awfully worried about my parents. I can take care of myself just fine."

Just then another person sat down next to the man Y/n was trying to whittle away at. He poked his elbow at him, "Who's this?"

"Don't know. Someone who's about to go back to her table with her little girlfriends."

Biting her lip she traced the rim of her martini glass with her fingertip, keeping her eyes set on the handsome tattooed one, "Not even a smile. Just one? Please?"

"Like I already said, I'm way too old for you."

The other man leaned over and reached to tap Y/n's shoulder, "Hey. Forget about Harry, here. You can bring me home with you if you're looking for a daddy tonight."

She frowned and looked him up and down to asses. He was late 40s perhaps, wearing a local band t-shirt, ripped jeans, and a backward cap to make himself appear a little more youthful. "No thanks. You'd know if I was interested in you."

Harry bit the inside of his cheek to stop himself from smiling at her retort. She was definitely too young but he liked her spunk.

"Now, Harry…" she said his name slowly as she leaned a little closer, "I've got your name thanks to your friend. Can I have a smile?"

"Why?" He stared down at her, the caress of his gaze felt infinite and she found her skin convecting in its wake. He might be hard to crack but this one would be worth it, she determined.

She sighed and slid her finger dangerously close to his wrist as he looked down at her nail and watched her trail it near his arm, "I just hoped to see you smile is all. Too handsome to have such a sour scowl on your face."

"And you're hardly old enough to be so confident to walk up to a strange man at a bar."

She laughed and tilted her head, "You planning on doing something bad to me, Harry?"

And that. That pulled a reaction out of him that spread over his features slowly as he shook his head in disbelief, "Darlin', you wouldn't be able to handle me."

Her eyes widened slightly. Now she was definitely not giving up. Y/n wasn't one to fail and Harry might be making her work hard for it but she couldn't imagine it wouldn't be worth it in the end.

"Is that a challenge or something?" She softly scraped her nail over his tattooed wrist and Harry watched her red nail work over his skin.

His resolve was fading fast. She could tell he wasn't going to keep denying her. And why should he? If he was single, which he appeared to be, what was the harm in having a little fun with someone younger? Y/n didn't mind. And he certainly shouldn't either.

"If it were a challenge you'd know it. Lots of other guys here, Y/n. Go enjoy your night with someone closer to your own age."

She sighed in annoyance. But he hadn't moved his arm away from her and she was going to take that as a sign.

Dragging the toe of her shoe into his shin she grinned, "I don't want to enjoy my night with someone my own age. Not tonight anyway. I think you've convinced me that I need to test out this theory of yours. That you think I can't handle you. Cause I bet I can."

With his eyes piercing into hers, he took another sip of his drink. She thought she might have just convinced him to give her a smile at the very least because it looked like he was weighing his options. And if she could get him to smile she might have luck with the rest.

He tilted his chin upward for a moment, eyes aimed at the ceiling like he was calling on a higher power for strength, "Go back to your friends, Y/n. Any other man here would love to have your company."

"But you wouldn't love to have my company?"

"I mean… I'm still here," the other man raised his hand and leaned into Harry, "Honey we could have so much fun. Any man who'd turn you down is either battin' for the other team or more likely," he chuckled and pushed his shoulder into Harry's teasingly, "He can't get it up anymore."

Y/n's mouth dropped open at that and Harry turned to look at the man. She wished she could see the look on his face, "Sit the fuck back down, John. She already told you she's not interested in you."

"Yeah, and you're not interested in her so what's it matter to you? Look at her, Harry. Practically begging you. Young and bubbly… Tight—"

Harry's hand covered John's throat as he pushed him away, nearly making his stool topple over, "Get the fuck outta here. You had too much whisky tonight."

"Aww… come on Harry… I was just jokin'!"

She watched as he stood from his stool and looked down at John, "And you thought that was funny? You like making jokes about women like that?"

The man put his hands up in surrender, "I'm out. Here…" he threw a wad of cash on the bar top before he moved past Harry and then looked at Y/n, "My apologies if I offended you."

They watched as John left the bar quickly and then Harry sat back down before he waved at the bartender and signaled for the check, "Just the one whisky neat."

"You're leaving already? Night's still young, Harry."

He sucked at his teeth as he scraped his gaze over her face and down to her cleavage. She smiled when she watched the path his eyes had taken.

The bartender handed him the bill and Harry leaned over to pull his wallet from his back pocket.

She scooted closer to him, "You headed home?"

He nodded, but not necessarily in answer to her question, it was more of an appraisal kind of nod. He was still silent as he pulled cash out of his wallet.

"Thanks for that, by the way. I'm sure John's a nice guy and all but he's not really my type. And I'm sure he was wrong about you."

That got his attention. Harry flicked his gaze back to hers, "Wrong about me?"

She smiled, "The part where he said you couldn't get it up. You're not that old. I'm sure you still can. Right?"

He clenched his jaw and breathed out of his nostrils like he couldn't believe she'd asked him such a thing. He handed the bartender his cash with a nod before he stood up from his stool.

"Huh. Since you're so quiet about it maybe he was right," she goaded, pressing her lips together to flatten her smile as she looked up at him through her lashes.

Harry placed a palm down on the bar top next to her hand and leaned over her, "You're out of your depth here, Y/n."

"Now, you don't really know that do you? Just because I'm younger than you doesn't mean I don't know what I'm doing."

"You're awfully pushy. Not used to hearing no, are you?"

Y/n watched as the edge of his mouth lifted in amusement and she widened her eyes and pointed, "You're almost smiling."

He shook his head and looked around the bar before pinning his gaze back to hers, "I hope you enjoy the rest of your night. But your luck has run out with me, princess."

Harry stood to his full height and Y/n decided to try one last time, "So it's true then. What he said."

He stopped and turned to look back at her, a slow burning heat behind his gaze, "Couldn't be further from the truth."

She smiled and slid off her stool to stand in front of him. His height was impressive, "Prove it."

The line of his jaw hardened, turning his cheekbones into slashes of tension. His eyes simmered as he weighed his options. Finally, a hint of a smile stretched over his mouth. A small one, but still.

"I don't need to prove anything to silly little girls."

"Good thing I'm not a silly little girl. I'm a grown woman, Harry."

Y/n knew she was pushing it. She'd never needed to throw herself at any man before. But because of that, she wasn't used to rejection either. Maybe it was a good lesson for her ego. She knew her big fault was how entitled she could act sometimes. But that was partly thanks to how she was raised. It's better to act like a man to get what you want in life, her dad told her. And so far, that had been true. Some women balked at her confidence and her bold attitude. She wasn't demure or sweet enough. And men would often refer to her as a bitch or say that she was trying too hard.

She'd work on her ego another time. But right now? She was focused on winning this battle.

"What do you want with someone like me anyway? Hm? I'm old, Y/n. What's in it for you?"

Blinking her eyes she shook her head, "You're not old, first of all. Secondly, you're really attractive. It doesn't need to go much deeper than that, does it? I just think you're handsome. And I do kind of like a challenge."

"I can see that you like a challenge. It's the only reason I haven't walked out that door yet. Kind of relentless."

She smiled, "So it's working?"

Another half-smile worked its way up his mouth as he laughed in disbelief, "Are you surprised that it is?"

His pupils coasted over her figure and then back up to her face. The warmth of his gaze singed her skin like an open flame.

"I guess I just didn't know how difficult it'd be with you."

He licked his lips, "Difficult. You have no idea. But looks like you're about to find out. Go tell your friends what's going on. Meet me out front."

Y/n watched him turn and walk away. She was shocked. For a minute she thought he wasn't going to go for it at all.

Shaking off the sudden surprise of having gotten to him she settled up with the bartender and then stopped at the table with her friends. They were just about to give her condolences for having oversold her ability but she interrupted. "He's waiting for me outside. Location is on. Don't wait up!"

Harry was leaning against a black car in the parking lot when she stepped out of the doors. The moment he saw her he pushed himself off the car and opened the passenger door for her.

It was going to be tricky to maintain the kind of confidence she'd been feigning with him up until then but there was no part of her that didn't want to find out what he could show her.

She watched as Harry sat down in the driver's seat and started up his car. He took up too much space in the seat. His big hand wrapped around the leather steering wheel while his other encased the shift stick. Even the way he drove was turning her on.

She was pleased that she'd wormed her way under his skin and that he'd given in. She'd try her best to make it worth his while. Reaching across the console she put her hand on his thigh and he glanced down quickly before setting his gaze back on the road.

Now, Harry had slept with younger women a couple of times. He generally preferred someone closer to his age because he liked the confidence and experience that came with age. Women in their 20s were often in a different stage of life and that was fine –normal even, but it just usually wasn't a match for him. Not sexually and not mentally.

But Y/n was unusually confident for being so young. Persistent. He liked it, he couldn't lie. Whether or not she really had much else going for her beyond confidence, he guessed he'd find out. Well, she was very cute too. She did have that in her favor.

And Y/n at least seemed like she knew what she wanted. It was flattering as well. Being approached by such a pretty young thing. He figured the moment he told her to go back to her friends she'd give up but she was just fiery enough that she wasn't deterred.

When she ran her nail over his wrist he knew he was screwed. She was just close enough that he could smell her perfume and then she nudged her shoe into his shin and all he could think about was that she really wanted to be shown a good time and if anyone could it was him.

Harry knew his way around a woman's body. They were all different and he liked finding all the buttons and things that made them purr. In his experience, though, the younger the woman, the less she knew her own body. He didn't know if Y/n was just talking a big game but he was about to find out.

He stayed quiet as she ran her hand down his thigh and he shifted as the car accelerated past the green light. He'd see if she'd do anything with her hand but maybe she'd just pet at him like a novelty toy. He didn't expect—

"This is okay?" She asked him, her tone sultry as she palmed at his crotch.

He licked his lips, "Have at it."

His cock fattened up nicely with not much effort on her part. Proof that he definitely could get it up. Plucking at his button she looked from his face to her fingers as she leaned further over the console to reach her hand into his open pants to help him with the awkward angle of his dick. He seemed to appreciate that as he shifted under her palm.

Rubbing over his heather grey briefs she peeled down the elastic band the slightest to get a peek. The dark shade of pink on his tip matched the muted raspberry of his lips. She slid the pad of her middle finger over the slit and he softly inhaled through his teeth.

She wouldn't be able to give him roadhead like she wanted. It was impossible with the stick shift in the way. But she could wrap her fingers around his shaft and feel him under her palm until they got wherever they were going.

"Mmm… It's so big, Harry. Knew you would be. Might be the biggest I've seen in person. Can't tell yet, though. Have to wait to see when we've got these off."

Harry pushed a laughed breath through his nose. She was a bold thing. Her assertiveness was a turn-on. He didn't like meek and shy. Not when it came to sex.

When she spit into her palm and smeared it down his length, the best she could, he parted his lips and stepped on the gas. She was already exceeding any expectations he had for her. Maybe she'd prove him wrong.

Her nail scraped the underside of him and she moaned, "Really want it in my mouth."

He gulped harshly and ticked his jaw, "Just be patient. I'll let you put it in your mouth soon enough."

"And where are we going? Your place?"

He nodded, "Just a few minutes away."

She squeezed around him and pulled upward slowly. She knew already, he was well above average and she was going to have to work to give him a proper blowy.

His house was a one story, the driveway at the front with a garage attached. He lifted his hand and pushed on a device that was clinging to his sun visor and the garage door began to open. There was a covered motorcycle along the back wall and then the garage door closed after he shut off the engine.

She moved her hand away and unbuckled herself as he got out. When she reached down to pick up her little purse she realized her panties were already wet. She grinned as she stepped out, adjusting her dress before closing the door, and then followed behind him as he led her into a dark hallway.

When he turned on the lights she took it all in. Hardwood floors led into a dining area and then a kitchen. Hung on the walls were photos of himself with two children and then more framed photos with just the kids.

"Do you have kids?"

"I do. Boy and a girl. 7 and 10."

"You're not married are you?"

He laughed, "If I were you'd have known. Wouldn't have been out in the first place if I had a wife waiting for me at home."

She nodded as he turned on the kitchen light and pulled out two glasses before filling them with water.

"Divorced?"

Handing her a glass he squinted, "Yes."

She took a sip. He was a man of few words she'd gathered. She looked around the kitchen. Wood cabinets, an outdated laminate countertop, stainless steel appliances. The space could use some updating but it was large and he had a big pantry.

Sitting the glass down on the counter she watched him closely. His pants were still unbuttoned. She eyed the space at his crotch as he placed his own glass down next to hers.

"It's not gonna suck itself."

She laughed and looked up at him. He had a genuine smile on his face that time. The first real smile she'd seen from him all night. A healthy row of clean teeth, a dimple…

"Hmm… I think you're right. Let's see what we've got…"

She moved in front of him and placed her hands on his pants to push them away but before she could inch them down he wrapped his meaty hand around the back of her neck and drew her into his chest. His mouth was warm and soft. His tongue tasted like the whisky he'd been drinking.

Letting go of his pants she held onto his biceps as he used his free hand to push her hips against his. Still nice and hard. He ran his tongue over her lips and she moaned into his mouth. He worked his warm lips down to her jaw and then he licked upward on her neck, the wet patch was cool on her skin from the air in the kitchen. He did it again and her knees almost gave out. She hadn't been licked like that before.

He kissed over her clavicle and then drew his tongue over her flesh. Her heart was thrumming quickly and she squeezed his strong arms when he rutted against her.

"You good at sucking cock, Y/n?" He pushed his nose against her jawline and the hot breath from his words scattered over the skin on her neck.

"I want to be," she spoke breathlessly, eyes fluttering closed as he mawed at her throat.

He parted from her neck and looked down at her, half-lidded gaze and spit-slicked lips, "Go on."

Instantly she dropped to her knees as her fingers worked deftly at pulling his pants down and then his underwear. She'd sucked a handful of dicks so she knew a couple of moves.

Getting her hand around his thick shaft proved to be a small challenge. To say he was thick… understatement. Long too. His tip was smooth, mushroomed with ridges along the length that she hoped she'd get to feel later on. His was the kind of cock that women dreamed of.

Looking up at him she licked her palm and used her spit to pump him slowly. Another glob over his tip for good measure. Then she pressed a kiss to the base of him, just over his sac, and screwed her eyes upward to watch his expression as she licked his balls, one side at a time. She wound her tongue all around to wet him before sucking at one side, pulling it into her mouth and he let out a ragged breath, his dark pupils spreading inky until the soft green had almost vanished.

He liked it.

She worked around the other side, sucking him in again and swirling her tongue softly underneath the tender bits. He gripped the counter behind himself.

Pulling off she straightened her back and licked upward, feeling every delicious thick ridge along his shaft until her tongue met his smooth crown. Laving every crevice of his tip, she dipped her tongue into his slit and then ran it under the frenulum before she wetted every inch of his glans.

Her mouth was watering when she parted her lips around him and flitted her gaze upward. He was watching her with a slack jaw as she took him a little deeper. He cradled the back of her head and moaned.

"Just suck the tip…."

She blinked up at him and pulled her lips just over the lip, swirling and suckling around him like he wanted.

"Fuck. Just like that." His hand at the back of her head was easy. He didn't push or pull. It was more like a pleased gesture as his fingertips flexed around her skull gently.

Y/n would have liked to have gone deeper. Wanted to show him her best work. But he seemed rather happy with what she was doing.

She bobbed a couple of times, only to slide her lips back to his tip. Her pace was slow when she began to stroke his length with a little twisting motion.

He was big. She knew she could take more but in a way, she was grateful that that was all he was asking for.

A groan fell from his chest and he bucked forward, his cock slipping down her tongue and she sucked, drawing more of him in as she moved her hands away.

"Goddamnit, you're good."

She took that as permission to go deeper. Relaxing her jaw she closed her eyes and held her breath, pushing down to her limit. She filled her throat with his cock the best she could and gurgled around his tip.

He coughed out a moan and then thumbed at her cheek, "Alright, that's good."

She pulled off of him. His heavy cock aimed right at her face when she sat back on her knees and looked up at him, "I can do better than that."

He laughed and put his hand out for her to take, helping her stand up, "I bet you can. Come on."

Harry kept her hand in his as he led her to his bedroom. It was just past the dark living space and he turned on a floor lamp on the opposite side of the room from the bed. When he turned back toward her he cupped her face and kissed her again.

She pressed her hand into his warm, hard chest and he reached around the back of her dress to pull the zipper downward, his fingers dragging down her skin as he went. His touch sent a tremor down her spine as continued kissing her wetly.

He stepped back, helping her out of her dress until it fell to the floor. His eyes raked over her body and he smoothed his hands over her hips and up to her bra-covered breasts. He stepped in closer, walking her backward toward his bed. He put his hands back on her hips and nudged her to sit before he reached down to lift her leg up by her calf, removing her heels, one at a time.

Y/n's thong was drenched. She stared at him while he placed her shoes side by side at the foot of the bed and then he placed his big palms on her thighs, pushing her legs open, "Lie back."

She let her back hit the mattress as Harry got to his knees on the floor. An arm reached under her thigh as he spread her apart and then she felt her panties being pulled at until her her wet pusslips were right in his face. He groaned and felt a hand slide up the inside of her thigh. He pressed his mouth over her mons and looked up at her before he opened his mouth wide and drew his tongue through her crease making her gasp.

"Get your bra off."

She pushed herself up slightly and worked at the clasp of her bra between moans as Harry continued licking at her pussy. When she pulled her arm through the flimsy material he lifted his head and reached around her back, pulling her closer to the edge of the bed and he sucked a nipple into his mouth.

"Oh, fuck!"

Y/n's finger and her long nails pushed into Harry's hair and scraped at his scalp as he licked and pulled at each nipple. He buried his face between her tits and let out a low sound, like he was murmuring something to her but only her breasts were allowed to hear it.

When he sunk back down he pushed at her so she'd lie back and he started in on her clit, one hand holding her panties to the side as he devoured her glistening cunt.

She kept feeling like she was going to slide off the edge of the bed but Harry's grip on her kept her still. His tongue and his lips were magic as he drew her to her end. She yanked at his hair and babbled his name on repeat as her spine bowed off the bed when she came.

Her chest was still rising and falling heavy when she felt her body being pushed upward. She popped her eyes open and watched him roll a condom over his shaft before he kneed back up onto the bed next to her. He was stark naked. His body was insane. Thick muscle and masculine everything. Tattoos scatter over his arms and chest.

Fuck, she muttered under her breath.

"Flip over, for me," his deep voice was husky as he motioned toward her to move.

She rolled to her stomach and she felt his fingers slide between the band of her panties and her hips as he pulled them down her legs.

"Ass up a little. I want to see all of you, Y/n."

She grinned and turned to look at him over her shoulder as she lifted her hips and spread her thighs. His lips were parted as he grabbed her ass and squeezed, making her cheeks spread apart. He inhaled sharply through his teeth and then dipped in, kissing her pussy from behind before licking upward over her ass.

She squealed quietly and bit her lip, still watching him behind her as he lifted, a lopsided grin on his face. He gazed at her as he fisted the base of his cock and slid the head up and down her soaked folds before he tipped his hips to push in just the tip.

"Gorgeous. Gonna look even better wrapped around cock. You like anal?"

"Never tried it."

He licked his lips and pressed his lips together as he looked at the spot where his dick was pressed against her cunt, "Figured. S'alright. Pussy's my favorite anyway."

"We could try… if you want."

He looked back into her eyes, a cocky smile on his face, "Your little hole would need to be trained. And that takes time. So, there will be no anal tonight. Not gonna try and hurt you. But that's a cute thought."

He canted his hips inward, eyes on hers and her mouth dropped open when she felt her entrance splitting open for him. She was tight, but so slick, it only took a few slow thrusts until he was buried in with a low grunt. He pulled back and then pushed his entire length into the hilt.

"Fuck—fuck!" She cried and stuffed her face into the blankets.

"Too much?"

"No! It's so good. You're just so big…" She began to send her hips back against him and Harry slowly fucked in to match her pace. His eyes were everywhere. On her puss getting split open on his cock, the curve of her lower back, the swell of her ass.

He just knew she'd look so sweet with her ass stuffed too, but good things like that couldn't be rushed which was a shame.

Every thrust was gushy wet. Y/n bubbled out small moans every time his dick brushed deep into her guts. It was better than she imagined. The way he filled her to the brim was going to turn into an addiction. She'd never slept with any man that had her wanting seconds before they'd even finished.

"Oh my god…" she mewled into the comforter.

"Fuck, I know, baby…"

She fit him like a glove, it was perfect. He went in a little faster, balls thudding against her skin rhythmically making her bounce forward as she spread around his girth. When he ground in she arched her back deeply and let out a soft groan, her hands fisted at the blanket and Harry reached around and smeared his fingertips over her clit.

It had her panting and pushing into him feverishly. She'd needed the friction on her throbbing button and he'd found it easily, thick, rough fingerprints slicking back and forth as he rutted in and in. It sent electrical sparks over her limbs.

"Like that? Needs her clit touched? Shit baby, act like you've never been touched by a man right here before…" he plucked at her like he was playing the guitar and she began to fade, her moans getting caught in her chest.

He could feel her walls tightening around him as he drove in deep.

"Fuck, Harry— fuck!"

He grinned as he watched her shudder, "Give it up, Y/n. There you go…"

She began to pulse around him, a constant stream of nonsense falling from her lips as he stroked against her channel and pushed deep into her tummy, his fingers still working her clit with ease.

Just as her body had tipped and oxygen returned to her lungs he pulled out and she felt him taking her hips and turning her around to her back. Harry grabbed her ankles and lifted until each was settled over his shoulders and pushed back inside of her, cock drilling down to her core making her teeth chatter at the way he split her down the middle.

Harry leaned over her, cock buried deep as she watched her pretty face twist up with pleasure. Plapping into her, her tits wobbled as his balls tightened against his body. The harder he plunged in, the more her legs shook. Soon, her ankles had slipped down and her feet hit the mattress as he continued drilling into her. His face was flushed hot, lips parted, muscles tensed.

Reaching up to his neck she smoothed her fingers over his warm skin and he lowered his chest down to hers and kissed her. That filthy tongue ran over her lips and he sloppily sipped at her between sucking at her lips. Her brain had turned to jelly.

She felt his hand on her outer thigh squeezing and brushing as he fucked down into her. "Mmm… fuck, Y/n, m'gonna come…"

He trembled over her, thick thighs pressed down and flexed as he rutted in and in and in, and then… he stilled. A deep, guttural moan vibrated through his chest down into hers.

She sighed when she felt him throbbing, pumping into his condom. Her fingers caressed the muscles over his back and she gasped when he bucked in harshly, once more as he emptied the last of his come into the rubber wrapped around his cock.

He slowed his kisses until they were lazy little pecks and then he looked down at her, his chest heaving. She was already grinning up at him.

"What?"

She blinked her eyes, "That was fun."

He puffed out a breath, "I guess that's a good way to describe it."

Harry was a gentleman as he pulled out slowly and helped her off the bed and led her to his bathroom. He helped her clean up and listened to her tell him about her job —just reminding him that she was an adult after he commented on her being so young again.

When she picked her dress up off the floor and started to step into it, Harry frowned, "What are you doing?"

She stopped and raised her brows. "Getting dressed. Was gonna call an Uber. I'm sure you don't want a stranger in your house all night," she laughed.

Harry pulled at her hand, making her drop her dress, "What kind of men have you been hanging out with that let you leave in an Uber at 2 am? You'll stay here."

She opened her mouth and then closed it in surprise before tilting her head in confusion, "Really? I just assumed—"

"You'll stay the night here. There's no way in hell you're getting an Uber at this time of night. It's dangerous."

She grinned and shrugged, "Well then… can I have a shirt or something to sleep in?"

He placed his warm hands on her hips, "You can have a t-shirt if you like. I prefer to sleep naked myself."

"Oh yeah? I usually do too as a matter of fact."

He held her out in his arms and eyed her naked frame, "Looks like we're both good to go then. We'll get you sorted in the morning. I'll give you a ride home then."

"I think you just want to keep me here with you," she chuckled.

Harry shook his head and released her hips before he popped her on the bottom with his palm. She bleated out a laugh.

"Get your ass in bed before I change my mind."

"Yes, sir."

. .

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[gurugirl]

OMGGGG!!! tell me we’ll be getting more of Dilf Harry- i LOVED it

THANK YOU!! So glad you loved it 🥰

There are no plans for more atm! I have so many other things I need to focus on for Tumblr already.

We'll see, though! I could change my mind lol!

xoxo

[gurugirl]

I do love an age gap! Thank you Leigh! 🤭🤭

Xoxo

DILF | older!harry

MAIN MASTERLIST

Summary: Y/n meets an older man at a bar and she's not taking no for an answer. Harry likes her persistence.

A/N: This was requested + this! Also, please think before you judge Y/n. She is very bold and confident in this. Maybe even a little pushy but Harry likes it (even if at first he doesn't give that impression). Also he's single so this isn't cheatrry!

Word Count: 6,580

Warning: age gap, smut, alcohol consumption (light)

. .

"That one. Total dilf. He looks grumpy. Bet you can't crack him."

Y/n laughed at her friend and looked down at her red-painted nails before narrowing her gaze on the attractive older man who was seated at the corner of the bar alone. He was nursing a whisky and he did look rather sullen. Unapproachable even.

"Why him?"

"Because he's hot. And I'm curious to see if you can get him to smile at least," Warren raised her brows, "I dare you."

Y/n tilted her head and assessed him. He was nice and big, taking up a decent amount of space at the bar, broad shoulders and back hunched as he leaned his muscular forearms on the wood of the bar top. Meaty hands placed on either side of his lowball glass. Thick brown waves on top of his head with a bit of silver coming in at the temples. But the handsome features on his face really set him apart. His granite jawline gave way to stubble that stretched over his skin and shaded in the spaces around his pink lips.

If she could "crack" him she wasn't sure she'd want just a smile. He looked yummy enough to eat.

Drinking down the last of her martini she pointed at Warren and then Tara, "Fine. Give me twenty minutes and I'll have him eating from the palm of my hand."

Tara laughed, "If you say so…"

She placed her heeled feet down on the floor and brushed her hands over her dress, "Oh, I do say so. Just watch and learn, ladies."

Y/n wasn't quite that confident, but she wasn't about to say no to dare. And she could hold her own when it came to flirting. She liked getting a little attention and if she could garner this one's interest it might be fun.

She sauntered up to the bar behind the man and noticed the way his t-shirt stretched over his lats and tapered loosely down at his waist. The guy was fit. And lucky her, there was an open stool next to him.

Sliding onto the seat she waved at the bartender to order another drink. She'd need all the courage she could get, in whatever form she could get it.

Tapping her long nails on the lacquered wood she felt nerves thrumming through veins before turning toward the man finally. He hadn't seemed to take note of her yet, which honestly was unusual in most cases. Maybe she thought too highly of herself but men tended to notice her right away. She appreciated the challenge, though.

Reaching her hand into his space to greet him, she pushed down her nerves to sound steady as she spoke, "I'm Y/n."

She watched his brow furrow as he turned to look at her hand and then up at her eyes, his expression, which she expected would soften once he looked at her, was unamused. A single light overhead lit the tops of their heads as a shadow cast over the side of his face and he didn't make a move to shake her hand, "And I'm old enough to be your dad."

A surprised scoff fell from her lips as she moved her hand away from him. She wiggled in her seat and crossed her leg over her thigh toward him, gulping down the initial rejection with as much grace as she could muster, "I think you're jumping to conclusions about my intentions. But so what if you're older than me? I don't mind. We're both adults, right?"

An unimpressed grunt rumbled from his throat before he took another sip of his whisky and he looked away from her toward the TV that hung not far away from where they sat.

The bartender placed her olive martini down on the bar in front of her, "It'll be on Y/n Y/l/n. I already have an open tab."

A sip of the salty drink felt warm down her throat. So he was going to be a bit tough to crack. She turned to look at her friends who were grinning in her direction.

Straightening her back to feel more confident she tried again, "So you're not gonna tell me your name even?"

Without looking at her, he licked his lips and ticked his jaw, "Y/n, I think it's past your bedtime."

She smiled at that. He'd said her name, which meant he'd been listening, "My bedtime is whenever I say it is, not when some grouchy stranger says."

He puffed out an amused laugh through his nose, "I am a stranger. Which means you should be cautious, little girl. Your dad didn't teach you about things like that?" He turned to look down at her again, and that time she saw the soft green color of his eyes as the light hit his face just right.

But now she was really determined. She smiled brightly at him and let her eyes coast over his tattooed arm and then back up to his face, "Are you telling me you're dangerous?"

He still didn't smile as he shook his head like he was surprised by her gall, "Do your parents know what you're up to tonight?"

"I'm 24. Graduated from college, live on my own, pay my bills, have a full-time job. You seem to be awfully worried about my parents. I can take care of myself just fine."

Just then another person sat down next to the man Y/n was trying to whittle away at. He poked his elbow at him, "Who's this?"

"Don't know. Someone who's about to go back to her table with her little girlfriends."

Biting her lip she traced the rim of her martini glass with her fingertip, keeping her eyes set on the handsome tattooed one, "Not even a smile. Just one? Please?"

"Like I already said, I'm way too old for you."

The other man leaned over and reached to tap Y/n's shoulder, "Hey. Forget about Harry, here. You can bring me home with you if you're looking for a daddy tonight."

She frowned and looked him up and down to asses. He was late 40s perhaps, wearing a local band t-shirt, ripped jeans, and a backward cap to make himself appear a little more youthful. "No thanks. You'd know if I was interested in you."

Harry bit the inside of his cheek to stop himself from smiling at her retort. She was definitely too young but he liked her spunk.

"Now, Harry…" she said his name slowly as she leaned a little closer, "I've got your name thanks to your friend. Can I have a smile?"

"Why?" He stared down at her, the caress of his gaze felt infinite and she found her skin convecting in its wake. He might be hard to crack but this one would be worth it, she determined.

She sighed and slid her finger dangerously close to his wrist as he looked down at her nail and watched her trail it near his arm, "I just hoped to see you smile is all. Too handsome to have such a sour scowl on your face."

"And you're hardly old enough to be so confident to walk up to a strange man at a bar."

She laughed and tilted her head, "You planning on doing something bad to me, Harry?"

And that. That pulled a reaction out of him that spread over his features slowly as he shook his head in disbelief, "Darlin', you wouldn't be able to handle me."

Her eyes widened slightly. Now she was definitely not giving up. Y/n wasn't one to fail and Harry might be making her work hard for it but she couldn't imagine it wouldn't be worth it in the end.

"Is that a challenge or something?" She softly scraped her nail over his tattooed wrist and Harry watched her red nail work over his skin.

His resolve was fading fast. She could tell he wasn't going to keep denying her. And why should he? If he was single, which he appeared to be, what was the harm in having a little fun with someone younger? Y/n didn't mind. And he certainly shouldn't either.

"If it were a challenge you'd know it. Lots of other guys here, Y/n. Go enjoy your night with someone closer to your own age."

She sighed in annoyance. But he hadn't moved his arm away from her and she was going to take that as a sign.

Dragging the toe of her shoe into his shin she grinned, "I don't want to enjoy my night with someone my own age. Not tonight anyway. I think you've convinced me that I need to test out this theory of yours. That you think I can't handle you. Cause I bet I can."

With his eyes piercing into hers, he took another sip of his drink. She thought she might have just convinced him to give her a smile at the very least because it looked like he was weighing his options. And if she could get him to smile she might have luck with the rest.

He tilted his chin upward for a moment, eyes aimed at the ceiling like he was calling on a higher power for strength, "Go back to your friends, Y/n. Any other man here would love to have your company."

"But you wouldn't love to have my company?"

"I mean… I'm still here," the other man raised his hand and leaned into Harry, "Honey we could have so much fun. Any man who'd turn you down is either battin' for the other team or more likely," he chuckled and pushed his shoulder into Harry's teasingly, "He can't get it up anymore."

Y/n's mouth dropped open at that and Harry turned to look at the man. She wished she could see the look on his face, "Sit the fuck back down, John. She already told you she's not interested in you."

"Yeah, and you're not interested in her so what's it matter to you? Look at her, Harry. Practically begging you. Young and bubbly… Tight—"

Harry's hand covered John's throat as he pushed him away, nearly making his stool topple over, "Get the fuck outta here. You had too much whisky tonight."

"Aww… come on Harry… I was just jokin'!"

She watched as he stood from his stool and looked down at John, "And you thought that was funny? You like making jokes about women like that?"

The man put his hands up in surrender, "I'm out. Here…" he threw a wad of cash on the bar top before he moved past Harry and then looked at Y/n, "My apologies if I offended you."

They watched as John left the bar quickly and then Harry sat back down before he waved at the bartender and signaled for the check, "Just the one whisky neat."

"You're leaving already? Night's still young, Harry."

He sucked at his teeth as he scraped his gaze over her face and down to her cleavage. She smiled when she watched the path his eyes had taken.

The bartender handed him the bill and Harry leaned over to pull his wallet from his back pocket.

She scooted closer to him, "You headed home?"

He nodded, but not necessarily in answer to her question, it was more of an appraisal kind of nod. He was still silent as he pulled cash out of his wallet.

"Thanks for that, by the way. I'm sure John's a nice guy and all but he's not really my type. And I'm sure he was wrong about you."

That got his attention. Harry flicked his gaze back to hers, "Wrong about me?"

She smiled, "The part where he said you couldn't get it up. You're not that old. I'm sure you still can. Right?"

He clenched his jaw and breathed out of his nostrils like he couldn't believe she'd asked him such a thing. He handed the bartender his cash with a nod before he stood up from his stool.

"Huh. Since you're so quiet about it maybe he was right," she goaded, pressing her lips together to flatten her smile as she looked up at him through her lashes.

Harry placed a palm down on the bar top next to her hand and leaned over her, "You're out of your depth here, Y/n."

"Now, you don't really know that do you? Just because I'm younger than you doesn't mean I don't know what I'm doing."

"You're awfully pushy. Not used to hearing no, are you?"

Y/n watched as the edge of his mouth lifted in amusement and she widened her eyes and pointed, "You're almost smiling."

He shook his head and looked around the bar before pinning his gaze back to hers, "I hope you enjoy the rest of your night. But your luck has run out with me, princess."

Harry stood to his full height and Y/n decided to try one last time, "So it's true then. What he said."

He stopped and turned to look back at her, a slow burning heat behind his gaze, "Couldn't be further from the truth."

She smiled and slid off her stool to stand in front of him. His height was impressive, "Prove it."

The line of his jaw hardened, turning his cheekbones into slashes of tension. His eyes simmered as he weighed his options. Finally, a hint of a smile stretched over his mouth. A small one, but still.

"I don't need to prove anything to silly little girls."

"Good thing I'm not a silly little girl. I'm a grown woman, Harry."

Y/n knew she was pushing it. She'd never needed to throw herself at any man before. But because of that, she wasn't used to rejection either. Maybe it was a good lesson for her ego. She knew her big fault was how entitled she could act sometimes. But that was partly thanks to how she was raised. It's better to act like a man to get what you want in life, her dad told her. And so far, that had been true. Some women balked at her confidence and her bold attitude. She wasn't demure or sweet enough. And men would often refer to her as a bitch or say that she was trying too hard.

She'd work on her ego another time. But right now? She was focused on winning this battle.

"What do you want with someone like me anyway? Hm? I'm old, Y/n. What's in it for you?"

Blinking her eyes she shook her head, "You're not old, first of all. Secondly, you're really attractive. It doesn't need to go much deeper than that, does it? I just think you're handsome. And I do kind of like a challenge."

"I can see that you like a challenge. It's the only reason I haven't walked out that door yet. Kind of relentless."

She smiled, "So it's working?"

Another half-smile worked its way up his mouth as he laughed in disbelief, "Are you surprised that it is?"

His pupils coasted over her figure and then back up to her face. The warmth of his gaze singed her skin like an open flame.

"I guess I just didn't know how difficult it'd be with you."

He licked his lips, "Difficult. You have no idea. But looks like you're about to find out. Go tell your friends what's going on. Meet me out front."

Y/n watched him turn and walk away. She was shocked. For a minute she thought he wasn't going to go for it at all.

Shaking off the sudden surprise of having gotten to him she settled up with the bartender and then stopped at the table with her friends. They were just about to give her condolences for having oversold her ability but she interrupted. "He's waiting for me outside. Location is on. Don't wait up!"

Harry was leaning against a black car in the parking lot when she stepped out of the doors. The moment he saw her he pushed himself off the car and opened the passenger door for her.

It was going to be tricky to maintain the kind of confidence she'd been feigning with him up until then but there was no part of her that didn't want to find out what he could show her.

She watched as Harry sat down in the driver's seat and started up his car. He took up too much space in the seat. His big hand wrapped around the leather steering wheel while his other encased the shift stick. Even the way he drove was turning her on.

She was pleased that she'd wormed her way under his skin and that he'd given in. She'd try her best to make it worth his while. Reaching across the console she put her hand on his thigh and he glanced down quickly before setting his gaze back on the road.

Now, Harry had slept with younger women a couple of times. He generally preferred someone closer to his age because he liked the confidence and experience that came with age. Women in their 20s were often in a different stage of life and that was fine –normal even, but it just usually wasn't a match for him. Not sexually and not mentally.

But Y/n was unusually confident for being so young. Persistent. He liked it, he couldn't lie. Whether or not she really had much else going for her beyond confidence, he guessed he'd find out. Well, she was very cute too. She did have that in her favor.

And Y/n at least seemed like she knew what she wanted. It was flattering as well. Being approached by such a pretty young thing. He figured the moment he told her to go back to her friends she'd give up but she was just fiery enough that she wasn't deterred.

When she ran her nail over his wrist he knew he was screwed. She was just close enough that he could smell her perfume and then she nudged her shoe into his shin and all he could think about was that she really wanted to be shown a good time and if anyone could it was him.

Harry knew his way around a woman's body. They were all different and he liked finding all the buttons and things that made them purr. In his experience, though, the younger the woman, the less she knew her own body. He didn't know if Y/n was just talking a big game but he was about to find out.

He stayed quiet as she ran her hand down his thigh and he shifted as the car accelerated past the green light. He'd see if she'd do anything with her hand but maybe she'd just pet at him like a novelty toy. He didn't expect—

"This is okay?" She asked him, her tone sultry as she palmed at his crotch.

He licked his lips, "Have at it."

His cock fattened up nicely with not much effort on her part. Proof that he definitely could get it up. Plucking at his button she looked from his face to her fingers as she leaned further over the console to reach her hand into his open pants to help him with the awkward angle of his dick. He seemed to appreciate that as he shifted under her palm.

Rubbing over his heather grey briefs she peeled down the elastic band the slightest to get a peek. The dark shade of pink on his tip matched the muted raspberry of his lips. She slid the pad of her middle finger over the slit and he softly inhaled through his teeth.

She wouldn't be able to give him roadhead like she wanted. It was impossible with the stick shift in the way. But she could wrap her fingers around his shaft and feel him under her palm until they got wherever they were going.

"Mmm… It's so big, Harry. Knew you would be. Might be the biggest I've seen in person. Can't tell yet, though. Have to wait to see when we've got these off."

Harry pushed a laughed breath through his nose. She was a bold thing. Her assertiveness was a turn-on. He didn't like meek and shy. Not when it came to sex.

When she spit into her palm and smeared it down his length, the best she could, he parted his lips and stepped on the gas. She was already exceeding any expectations he had for her. Maybe she'd prove him wrong.

Her nail scraped the underside of him and she moaned, "Really want it in my mouth."

He gulped harshly and ticked his jaw, "Just be patient. I'll let you put it in your mouth soon enough."

"And where are we going? Your place?"

He nodded, "Just a few minutes away."

She squeezed around him and pulled upward slowly. She knew already, he was well above average and she was going to have to work to give him a proper blowy.

His house was a one story, the driveway at the front with a garage attached. He lifted his hand and pushed on a device that was clinging to his sun visor and the garage door began to open. There was a covered motorcycle along the back wall and then the garage door closed after he shut off the engine.

She moved her hand away and unbuckled herself as he got out. When she reached down to pick up her little purse she realized her panties were already wet. She grinned as she stepped out, adjusting her dress before closing the door, and then followed behind him as he led her into a dark hallway.

When he turned on the lights she took it all in. Hardwood floors led into a dining area and then a kitchen. Hung on the walls were photos of himself with two children and then more framed photos with just the kids.

"Do you have kids?"

"I do. Boy and a girl. 7 and 10."

"You're not married are you?"

He laughed, "If I were you'd have known. Wouldn't have been out in the first place if I had a wife waiting for me at home."

She nodded as he turned on the kitchen light and pulled out two glasses before filling them with water.

"Divorced?"

Handing her a glass he squinted, "Yes."

She took a sip. He was a man of few words she'd gathered. She looked around the kitchen. Wood cabinets, an outdated laminate countertop, stainless steel appliances. The space could use some updating but it was large and he had a big pantry.

Sitting the glass down on the counter she watched him closely. His pants were still unbuttoned. She eyed the space at his crotch as he placed his own glass down next to hers.

"It's not gonna suck itself."

She laughed and looked up at him. He had a genuine smile on his face that time. The first real smile she'd seen from him all night. A healthy row of clean teeth, a dimple…

"Hmm… I think you're right. Let's see what we've got…"

She moved in front of him and placed her hands on his pants to push them away but before she could inch them down he wrapped his meaty hand around the back of her neck and drew her into his chest. His mouth was warm and soft. His tongue tasted like the whisky he'd been drinking.

Letting go of his pants she held onto his biceps as he used his free hand to push her hips against his. Still nice and hard. He ran his tongue over her lips and she moaned into his mouth. He worked his warm lips down to her jaw and then he licked upward on her neck, the wet patch was cool on her skin from the air in the kitchen. He did it again and her knees almost gave out. She hadn't been licked like that before.

He kissed over her clavicle and then drew his tongue over her flesh. Her heart was thrumming quickly and she squeezed his strong arms when he rutted against her.

"You good at sucking cock, Y/n?" He pushed his nose against her jawline and the hot breath from his words scattered over the skin on her neck.

"I want to be," she spoke breathlessly, eyes fluttering closed as he mawed at her throat.

He parted from her neck and looked down at her, half-lidded gaze and spit-slicked lips, "Go on."

Instantly she dropped to her knees as her fingers worked deftly at pulling his pants down and then his underwear. She'd sucked a handful of dicks so she knew a couple of moves.

Getting her hand around his thick shaft proved to be a small challenge. To say he was thick… understatement. Long too. His tip was smooth, mushroomed with ridges along the length that she hoped she'd get to feel later on. His was the kind of cock that women dreamed of.

Looking up at him she licked her palm and used her spit to pump him slowly. Another glob over his tip for good measure. Then she pressed a kiss to the base of him, just over his sac, and screwed her eyes upward to watch his expression as she licked his balls, one side at a time. She wound her tongue all around to wet him before sucking at one side, pulling it into her mouth and he let out a ragged breath, his dark pupils spreading inky until the soft green had almost vanished.

He liked it.

She worked around the other side, sucking him in again and swirling her tongue softly underneath the tender bits. He gripped the counter behind himself.

Pulling off she straightened her back and licked upward, feeling every delicious thick ridge along his shaft until her tongue met his smooth crown. Laving every crevice of his tip, she dipped her tongue into his slit and then ran it under the frenulum before she wetted every inch of his glans.

Her mouth was watering when she parted her lips around him and flitted her gaze upward. He was watching her with a slack jaw as she took him a little deeper. He cradled the back of her head and moaned.

"Just suck the tip…."

She blinked up at him and pulled her lips just over the lip, swirling and suckling around him like he wanted.

"Fuck. Just like that." His hand at the back of her head was easy. He didn't push or pull. It was more like a pleased gesture as his fingertips flexed around her skull gently.

Y/n would have liked to have gone deeper. Wanted to show him her best work. But he seemed rather happy with what she was doing.

She bobbed a couple of times, only to slide her lips back to his tip. Her pace was slow when she began to stroke his length with a little twisting motion.

He was big. She knew she could take more but in a way, she was grateful that that was all he was asking for.

A groan fell from his chest and he bucked forward, his cock slipping down her tongue and she sucked, drawing more of him in as she moved her hands away.

"Goddamnit, you're good."

She took that as permission to go deeper. Relaxing her jaw she closed her eyes and held her breath, pushing down to her limit. She filled her throat with his cock the best she could and gurgled around his tip.

He coughed out a moan and then thumbed at her cheek, "Alright, that's good."

She pulled off of him. His heavy cock aimed right at her face when she sat back on her knees and looked up at him, "I can do better than that."

He laughed and put his hand out for her to take, helping her stand up, "I bet you can. Come on."

Harry kept her hand in his as he led her to his bedroom. It was just past the dark living space and he turned on a floor lamp on the opposite side of the room from the bed. When he turned back toward her he cupped her face and kissed her again.

She pressed her hand into his warm, hard chest and he reached around the back of her dress to pull the zipper downward, his fingers dragging down her skin as he went. His touch sent a tremor down her spine as continued kissing her wetly.

He stepped back, helping her out of her dress until it fell to the floor. His eyes raked over her body and he smoothed his hands over her hips and up to her bra-covered breasts. He stepped in closer, walking her backward toward his bed. He put his hands back on her hips and nudged her to sit before he reached down to lift her leg up by her calf, removing her heels, one at a time.

Y/n's thong was drenched. She stared at him while he placed her shoes side by side at the foot of the bed and then he placed his big palms on her thighs, pushing her legs open, "Lie back."

She let her back hit the mattress as Harry got to his knees on the floor. An arm reached under her thigh as he spread her apart and then she felt her panties being pulled at until her her wet pusslips were right in his face. He groaned and felt a hand slide up the inside of her thigh. He pressed his mouth over her mons and looked up at her before he opened his mouth wide and drew his tongue through her crease making her gasp.

"Get your bra off."

She pushed herself up slightly and worked at the clasp of her bra between moans as Harry continued licking at her pussy. When she pulled her arm through the flimsy material he lifted his head and reached around her back, pulling her closer to the edge of the bed and he sucked a nipple into his mouth.

"Oh, fuck!"

Y/n's finger and her long nails pushed into Harry's hair and scraped at his scalp as he licked and pulled at each nipple. He buried his face between her tits and let out a low sound, like he was murmuring something to her but only her breasts were allowed to hear it.

When he sunk back down he pushed at her so she'd lie back and he started in on her clit, one hand holding her panties to the side as he devoured her glistening cunt.

She kept feeling like she was going to slide off the edge of the bed but Harry's grip on her kept her still. His tongue and his lips were magic as he drew her to her end. She yanked at his hair and babbled his name on repeat as her spine bowed off the bed when she came.

Her chest was still rising and falling heavy when she felt her body being pushed upward. She popped her eyes open and watched him roll a condom over his shaft before he kneed back up onto the bed next to her. He was stark naked. His body was insane. Thick muscle and masculine everything. Tattoos scatter over his arms and chest.

Fuck, she muttered under her breath.

"Flip over, for me," his deep voice was husky as he motioned toward her to move.

She rolled to her stomach and she felt his fingers slide between the band of her panties and her hips as he pulled them down her legs.

"Ass up a little. I want to see all of you, Y/n."

She grinned and turned to look at him over her shoulder as she lifted her hips and spread her thighs. His lips were parted as he grabbed her ass and squeezed, making her cheeks spread apart. He inhaled sharply through his teeth and then dipped in, kissing her pussy from behind before licking upward over her ass.

She squealed quietly and bit her lip, still watching him behind her as he lifted, a lopsided grin on his face. He gazed at her as he fisted the base of his cock and slid the head up and down her soaked folds before he tipped his hips to push in just the tip.

"Gorgeous. Gonna look even better wrapped around cock. You like anal?"

"Never tried it."

He licked his lips and pressed his lips together as he looked at the spot where his dick was pressed against her cunt, "Figured. S'alright. Pussy's my favorite anyway."

"We could try… if you want."

He looked back into her eyes, a cocky smile on his face, "Your little hole would need to be trained. And that takes time. So, there will be no anal tonight. Not gonna try and hurt you. But that's a cute thought."

He canted his hips inward, eyes on hers and her mouth dropped open when she felt her entrance splitting open for him. She was tight, but so slick, it only took a few slow thrusts until he was buried in with a low grunt. He pulled back and then pushed his entire length into the hilt.

"Fuck—fuck!" She cried and stuffed her face into the blankets.

"Too much?"

"No! It's so good. You're just so big…" She began to send her hips back against him and Harry slowly fucked in to match her pace. His eyes were everywhere. On her puss getting split open on his cock, the curve of her lower back, the swell of her ass.

He just knew she'd look so sweet with her ass stuffed too, but good things like that couldn't be rushed which was a shame.

Every thrust was gushy wet. Y/n bubbled out small moans every time his dick brushed deep into her guts. It was better than she imagined. The way he filled her to the brim was going to turn into an addiction. She'd never slept with any man that had her wanting seconds before they'd even finished.

"Oh my god…" she mewled into the comforter.

"Fuck, I know, baby…"

She fit him like a glove, it was perfect. He went in a little faster, balls thudding against her skin rhythmically making her bounce forward as she spread around his girth. When he ground in she arched her back deeply and let out a soft groan, her hands fisted at the blanket and Harry reached around and smeared his fingertips over her clit.

It had her panting and pushing into him feverishly. She'd needed the friction on her throbbing button and he'd found it easily, thick, rough fingerprints slicking back and forth as he rutted in and in. It sent electrical sparks over her limbs.

"Like that? Needs her clit touched? Shit baby, act like you've never been touched by a man right here before…" he plucked at her like he was playing the guitar and she began to fade, her moans getting caught in her chest.

He could feel her walls tightening around him as he drove in deep.

"Fuck, Harry— fuck!"

He grinned as he watched her shudder, "Give it up, Y/n. There you go…"

She began to pulse around him, a constant stream of nonsense falling from her lips as he stroked against her channel and pushed deep into her tummy, his fingers still working her clit with ease.

Just as her body had tipped and oxygen returned to her lungs he pulled out and she felt him taking her hips and turning her around to her back. Harry grabbed her ankles and lifted until each was settled over his shoulders and pushed back inside of her, cock drilling down to her core making her teeth chatter at the way he split her down the middle.

Harry leaned over her, cock buried deep as she watched her pretty face twist up with pleasure. Plapping into her, her tits wobbled as his balls tightened against his body. The harder he plunged in, the more her legs shook. Soon, her ankles had slipped down and her feet hit the mattress as he continued drilling into her. His face was flushed hot, lips parted, muscles tensed.

Reaching up to his neck she smoothed her fingers over his warm skin and he lowered his chest down to hers and kissed her. That filthy tongue ran over her lips and he sloppily sipped at her between sucking at her lips. Her brain had turned to jelly.

She felt his hand on her outer thigh squeezing and brushing as he fucked down into her. "Mmm… fuck, Y/n, m'gonna come…"

He trembled over her, thick thighs pressed down and flexed as he rutted in and in and in, and then… he stilled. A deep, guttural moan vibrated through his chest down into hers.

She sighed when she felt him throbbing, pumping into his condom. Her fingers caressed the muscles over his back and she gasped when he bucked in harshly, once more as he emptied the last of his come into the rubber wrapped around his cock.

He slowed his kisses until they were lazy little pecks and then he looked down at her, his chest heaving. She was already grinning up at him.

"What?"

She blinked her eyes, "That was fun."

He puffed out a breath, "I guess that's a good way to describe it."

Harry was a gentleman as he pulled out slowly and helped her off the bed and led her to his bathroom. He helped her clean up and listened to her tell him about her job —just reminding him that she was an adult after he commented on her being so young again.

When she picked her dress up off the floor and started to step into it, Harry frowned, "What are you doing?"

She stopped and raised her brows. "Getting dressed. Was gonna call an Uber. I'm sure you don't want a stranger in your house all night," she laughed.

Harry pulled at her hand, making her drop her dress, "What kind of men have you been hanging out with that let you leave in an Uber at 2 am? You'll stay here."

She opened her mouth and then closed it in surprise before tilting her head in confusion, "Really? I just assumed—"

"You'll stay the night here. There's no way in hell you're getting an Uber at this time of night. It's dangerous."

She grinned and shrugged, "Well then… can I have a shirt or something to sleep in?"

He placed his warm hands on her hips, "You can have a t-shirt if you like. I prefer to sleep naked myself."

"Oh yeah? I usually do too as a matter of fact."

He held her out in his arms and eyed her naked frame, "Looks like we're both good to go then. We'll get you sorted in the morning. I'll give you a ride home then."

"I think you just want to keep me here with you," she chuckled.

Harry shook his head and released her hips before he popped her on the bottom with his palm. She bleated out a laugh.

"Get your ass in bed before I change my mind."

"Yes, sir."

. .

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[gurugirl]

DILF | older!harry

MAIN MASTERLIST

Summary: Y/n meets an older man at a bar and she's not taking no for an answer. Harry likes her persistence.

A/N: This was requested + this! Also, please think before you judge Y/n. She is very bold and confident in this. Maybe even a little pushy but Harry likes it (even if at first he doesn't give that impression). Also he's single so this isn't cheatrry!

Word Count: 6,580

Warning: age gap, smut, alcohol consumption (light)

. .

"That one. Total dilf. He looks grumpy. Bet you can't crack him."

Y/n laughed at her friend and looked down at her red-painted nails before narrowing her gaze on the attractive older man who was seated at the corner of the bar alone. He was nursing a whisky and he did look rather sullen. Unapproachable even.

"Why him?"

"Because he's hot. And I'm curious to see if you can get him to smile at least," Warren raised her brows, "I dare you."

Y/n tilted her head and assessed him. He was nice and big, taking up a decent amount of space at the bar, broad shoulders and back hunched as he leaned his muscular forearms on the wood of the bar top. Meaty hands placed on either side of his lowball glass. Thick brown waves on top of his head with a bit of silver coming in at the temples. But the handsome features on his face really set him apart. His granite jawline gave way to stubble that stretched over his skin and shaded in the spaces around his pink lips.

If she could "crack" him she wasn't sure she'd want just a smile. He looked yummy enough to eat.

Drinking down the last of her martini she pointed at Warren and then Tara, "Fine. Give me twenty minutes and I'll have him eating from the palm of my hand."

Tara laughed, "If you say so…"

She placed her heeled feet down on the floor and brushed her hands over her dress, "Oh, I do say so. Just watch and learn, ladies."

Y/n wasn't quite that confident, but she wasn't about to say no to dare. And she could hold her own when it came to flirting. She liked getting a little attention and if she could garner this one's interest it might be fun.

She sauntered up to the bar behind the man and noticed the way his t-shirt stretched over his lats and tapered loosely down at his waist. The guy was fit. And lucky her, there was an open stool next to him.

Sliding onto the seat she waved at the bartender to order another drink. She'd need all the courage she could get, in whatever form she could get it.

Tapping her long nails on the lacquered wood she felt nerves thrumming through veins before turning toward the man finally. He hadn't seemed to take note of her yet, which honestly was unusual in most cases. Maybe she thought too highly of herself but men tended to notice her right away. She appreciated the challenge, though.

Reaching her hand into his space to greet him, she pushed down her nerves to sound steady as she spoke, "I'm Y/n."

She watched his brow furrow as he turned to look at her hand and then up at her eyes, his expression, which she expected would soften once he looked at her, was unamused. A single light overhead lit the tops of their heads as a shadow cast over the side of his face and he didn't make a move to shake her hand, "And I'm old enough to be your dad."

A surprised scoff fell from her lips as she moved her hand away from him. She wiggled in her seat and crossed her leg over her thigh toward him, gulping down the initial rejection with as much grace as she could muster, "I think you're jumping to conclusions about my intentions. But so what if you're older than me? I don't mind. We're both adults, right?"

An unimpressed grunt rumbled from his throat before he took another sip of his whisky and he looked away from her toward the TV that hung not far away from where they sat.

The bartender placed her olive martini down on the bar in front of her, "It'll be on Y/n Y/l/n. I already have an open tab."

A sip of the salty drink felt warm down her throat. So he was going to be a bit tough to crack. She turned to look at her friends who were grinning in her direction.

Straightening her back to feel more confident she tried again, "So you're not gonna tell me your name even?"

Without looking at her, he licked his lips and ticked his jaw, "Y/n, I think it's past your bedtime."

She smiled at that. He'd said her name, which meant he'd been listening, "My bedtime is whenever I say it is, not when some grouchy stranger says."

He puffed out an amused laugh through his nose, "I am a stranger. Which means you should be cautious, little girl. Your dad didn't teach you about things like that?" He turned to look down at her again, and that time she saw the soft green color of his eyes as the light hit his face just right.

But now she was really determined. She smiled brightly at him and let her eyes coast over his tattooed arm and then back up to his face, "Are you telling me you're dangerous?"

He still didn't smile as he shook his head like he was surprised by her gall, "Do your parents know what you're up to tonight?"

"I'm 24. Graduated from college, live on my own, pay my bills, have a full-time job. You seem to be awfully worried about my parents. I can take care of myself just fine."

Just then another person sat down next to the man Y/n was trying to whittle away at. He poked his elbow at him, "Who's this?"

"Don't know. Someone who's about to go back to her table with her little girlfriends."

Biting her lip she traced the rim of her martini glass with her fingertip, keeping her eyes set on the handsome tattooed one, "Not even a smile. Just one? Please?"

"Like I already said, I'm way too old for you."

The other man leaned over and reached to tap Y/n's shoulder, "Hey. Forget about Harry, here. You can bring me home with you if you're looking for a daddy tonight."

She frowned and looked him up and down to asses. He was late 40s perhaps, wearing a local band t-shirt, ripped jeans, and a backward cap to make himself appear a little more youthful. "No thanks. You'd know if I was interested in you."

Harry bit the inside of his cheek to stop himself from smiling at her retort. She was definitely too young but he liked her spunk.

"Now, Harry…" she said his name slowly as she leaned a little closer, "I've got your name thanks to your friend. Can I have a smile?"

"Why?" He stared down at her, the caress of his gaze felt infinite and she found her skin convecting in its wake. He might be hard to crack but this one would be worth it, she determined.

She sighed and slid her finger dangerously close to his wrist as he looked down at her nail and watched her trail it near his arm, "I just hoped to see you smile is all. Too handsome to have such a sour scowl on your face."

"And you're hardly old enough to be so confident to walk up to a strange man at a bar."

She laughed and tilted her head, "You planning on doing something bad to me, Harry?"

And that. That pulled a reaction out of him that spread over his features slowly as he shook his head in disbelief, "Darlin', you wouldn't be able to handle me."

Her eyes widened slightly. Now she was definitely not giving up. Y/n wasn't one to fail and Harry might be making her work hard for it but she couldn't imagine it wouldn't be worth it in the end.

"Is that a challenge or something?" She softly scraped her nail over his tattooed wrist and Harry watched her red nail work over his skin.

His resolve was fading fast. She could tell he wasn't going to keep denying her. And why should he? If he was single, which he appeared to be, what was the harm in having a little fun with someone younger? Y/n didn't mind. And he certainly shouldn't either.

"If it were a challenge you'd know it. Lots of other guys here, Y/n. Go enjoy your night with someone closer to your own age."

She sighed in annoyance. But he hadn't moved his arm away from her and she was going to take that as a sign.

Dragging the toe of her shoe into his shin she grinned, "I don't want to enjoy my night with someone my own age. Not tonight anyway. I think you've convinced me that I need to test out this theory of yours. That you think I can't handle you. Cause I bet I can."

With his eyes piercing into hers, he took another sip of his drink. She thought she might have just convinced him to give her a smile at the very least because it looked like he was weighing his options. And if she could get him to smile she might have luck with the rest.

He tilted his chin upward for a moment, eyes aimed at the ceiling like he was calling on a higher power for strength, "Go back to your friends, Y/n. Any other man here would love to have your company."

"But you wouldn't love to have my company?"

"I mean… I'm still here," the other man raised his hand and leaned into Harry, "Honey we could have so much fun. Any man who'd turn you down is either battin' for the other team or more likely," he chuckled and pushed his shoulder into Harry's teasingly, "He can't get it up anymore."

Y/n's mouth dropped open at that and Harry turned to look at the man. She wished she could see the look on his face, "Sit the fuck back down, John. She already told you she's not interested in you."

"Yeah, and you're not interested in her so what's it matter to you? Look at her, Harry. Practically begging you. Young and bubbly… Tight—"

Harry's hand covered John's throat as he pushed him away, nearly making his stool topple over, "Get the fuck outta here. You had too much whisky tonight."

"Aww… come on Harry… I was just jokin'!"

She watched as he stood from his stool and looked down at John, "And you thought that was funny? You like making jokes about women like that?"

The man put his hands up in surrender, "I'm out. Here…" he threw a wad of cash on the bar top before he moved past Harry and then looked at Y/n, "My apologies if I offended you."

They watched as John left the bar quickly and then Harry sat back down before he waved at the bartender and signaled for the check, "Just the one whisky neat."

"You're leaving already? Night's still young, Harry."

He sucked at his teeth as he scraped his gaze over her face and down to her cleavage. She smiled when she watched the path his eyes had taken.

The bartender handed him the bill and Harry leaned over to pull his wallet from his back pocket.

She scooted closer to him, "You headed home?"

He nodded, but not necessarily in answer to her question, it was more of an appraisal kind of nod. He was still silent as he pulled cash out of his wallet.

"Thanks for that, by the way. I'm sure John's a nice guy and all but he's not really my type. And I'm sure he was wrong about you."

That got his attention. Harry flicked his gaze back to hers, "Wrong about me?"

She smiled, "The part where he said you couldn't get it up. You're not that old. I'm sure you still can. Right?"

He clenched his jaw and breathed out of his nostrils like he couldn't believe she'd asked him such a thing. He handed the bartender his cash with a nod before he stood up from his stool.

"Huh. Since you're so quiet about it maybe he was right," she goaded, pressing her lips together to flatten her smile as she looked up at him through her lashes.

Harry placed a palm down on the bar top next to her hand and leaned over her, "You're out of your depth here, Y/n."

"Now, you don't really know that do you? Just because I'm younger than you doesn't mean I don't know what I'm doing."

"You're awfully pushy. Not used to hearing no, are you?"

Y/n watched as the edge of his mouth lifted in amusement and she widened her eyes and pointed, "You're almost smiling."

He shook his head and looked around the bar before pinning his gaze back to hers, "I hope you enjoy the rest of your night. But your luck has run out with me, princess."

Harry stood to his full height and Y/n decided to try one last time, "So it's true then. What he said."

He stopped and turned to look back at her, a slow burning heat behind his gaze, "Couldn't be further from the truth."

She smiled and slid off her stool to stand in front of him. His height was impressive, "Prove it."

The line of his jaw hardened, turning his cheekbones into slashes of tension. His eyes simmered as he weighed his options. Finally, a hint of a smile stretched over his mouth. A small one, but still.

"I don't need to prove anything to silly little girls."

"Good thing I'm not a silly little girl. I'm a grown woman, Harry."

Y/n knew she was pushing it. She'd never needed to throw herself at any man before. But because of that, she wasn't used to rejection either. Maybe it was a good lesson for her ego. She knew her big fault was how entitled she could act sometimes. But that was partly thanks to how she was raised. It's better to act like a man to get what you want in life, her dad told her. And so far, that had been true. Some women balked at her confidence and her bold attitude. She wasn't demure or sweet enough. And men would often refer to her as a bitch or say that she was trying too hard.

She'd work on her ego another time. But right now? She was focused on winning this battle.

"What do you want with someone like me anyway? Hm? I'm old, Y/n. What's in it for you?"

Blinking her eyes she shook her head, "You're not old, first of all. Secondly, you're really attractive. It doesn't need to go much deeper than that, does it? I just think you're handsome. And I do kind of like a challenge."

"I can see that you like a challenge. It's the only reason I haven't walked out that door yet. Kind of relentless."

She smiled, "So it's working?"

Another half-smile worked its way up his mouth as he laughed in disbelief, "Are you surprised that it is?"

His pupils coasted over her figure and then back up to her face. The warmth of his gaze singed her skin like an open flame.

"I guess I just didn't know how difficult it'd be with you."

He licked his lips, "Difficult. You have no idea. But looks like you're about to find out. Go tell your friends what's going on. Meet me out front."

Y/n watched him turn and walk away. She was shocked. For a minute she thought he wasn't going to go for it at all.

Shaking off the sudden surprise of having gotten to him she settled up with the bartender and then stopped at the table with her friends. They were just about to give her condolences for having oversold her ability but she interrupted. "He's waiting for me outside. Location is on. Don't wait up!"

Harry was leaning against a black car in the parking lot when she stepped out of the doors. The moment he saw her he pushed himself off the car and opened the passenger door for her.

It was going to be tricky to maintain the kind of confidence she'd been feigning with him up until then but there was no part of her that didn't want to find out what he could show her.

She watched as Harry sat down in the driver's seat and started up his car. He took up too much space in the seat. His big hand wrapped around the leather steering wheel while his other encased the shift stick. Even the way he drove was turning her on.

She was pleased that she'd wormed her way under his skin and that he'd given in. She'd try her best to make it worth his while. Reaching across the console she put her hand on his thigh and he glanced down quickly before setting his gaze back on the road.

Now, Harry had slept with younger women a couple of times. He generally preferred someone closer to his age because he liked the confidence and experience that came with age. Women in their 20s were often in a different stage of life and that was fine –normal even, but it just usually wasn't a match for him. Not sexually and not mentally.

But Y/n was unusually confident for being so young. Persistent. He liked it, he couldn't lie. Whether or not she really had much else going for her beyond confidence, he guessed he'd find out. Well, she was very cute too. She did have that in her favor.

And Y/n at least seemed like she knew what she wanted. It was flattering as well. Being approached by such a pretty young thing. He figured the moment he told her to go back to her friends she'd give up but she was just fiery enough that she wasn't deterred.

When she ran her nail over his wrist he knew he was screwed. She was just close enough that he could smell her perfume and then she nudged her shoe into his shin and all he could think about was that she really wanted to be shown a good time and if anyone could it was him.

Harry knew his way around a woman's body. They were all different and he liked finding all the buttons and things that made them purr. In his experience, though, the younger the woman, the less she knew her own body. He didn't know if Y/n was just talking a big game but he was about to find out.

He stayed quiet as she ran her hand down his thigh and he shifted as the car accelerated past the green light. He'd see if she'd do anything with her hand but maybe she'd just pet at him like a novelty toy. He didn't expect—

"This is okay?" She asked him, her tone sultry as she palmed at his crotch.

He licked his lips, "Have at it."

His cock fattened up nicely with not much effort on her part. Proof that he definitely could get it up. Plucking at his button she looked from his face to her fingers as she leaned further over the console to reach her hand into his open pants to help him with the awkward angle of his dick. He seemed to appreciate that as he shifted under her palm.

Rubbing over his heather grey briefs she peeled down the elastic band the slightest to get a peek. The dark shade of pink on his tip matched the muted raspberry of his lips. She slid the pad of her middle finger over the slit and he softly inhaled through his teeth.

She wouldn't be able to give him roadhead like she wanted. It was impossible with the stick shift in the way. But she could wrap her fingers around his shaft and feel him under her palm until they got wherever they were going.

"Mmm… It's so big, Harry. Knew you would be. Might be the biggest I've seen in person. Can't tell yet, though. Have to wait to see when we've got these off."

Harry pushed a laughed breath through his nose. She was a bold thing. Her assertiveness was a turn-on. He didn't like meek and shy. Not when it came to sex.

When she spit into her palm and smeared it down his length, the best she could, he parted his lips and stepped on the gas. She was already exceeding any expectations he had for her. Maybe she'd prove him wrong.

Her nail scraped the underside of him and she moaned, "Really want it in my mouth."

He gulped harshly and ticked his jaw, "Just be patient. I'll let you put it in your mouth soon enough."

"And where are we going? Your place?"

He nodded, "Just a few minutes away."

She squeezed around him and pulled upward slowly. She knew already, he was well above average and she was going to have to work to give him a proper blowy.

His house was a one story, the driveway at the front with a garage attached. He lifted his hand and pushed on a device that was clinging to his sun visor and the garage door began to open. There was a covered motorcycle along the back wall and then the garage door closed after he shut off the engine.

She moved her hand away and unbuckled herself as he got out. When she reached down to pick up her little purse she realized her panties were already wet. She grinned as she stepped out, adjusting her dress before closing the door, and then followed behind him as he led her into a dark hallway.

When he turned on the lights she took it all in. Hardwood floors led into a dining area and then a kitchen. Hung on the walls were photos of himself with two children and then more framed photos with just the kids.

"Do you have kids?"

"I do. Boy and a girl. 7 and 10."

"You're not married are you?"

He laughed, "If I were you'd have known. Wouldn't have been out in the first place if I had a wife waiting for me at home."

She nodded as he turned on the kitchen light and pulled out two glasses before filling them with water.

"Divorced?"

Handing her a glass he squinted, "Yes."

She took a sip. He was a man of few words she'd gathered. She looked around the kitchen. Wood cabinets, an outdated laminate countertop, stainless steel appliances. The space could use some updating but it was large and he had a big pantry.

Sitting the glass down on the counter she watched him closely. His pants were still unbuttoned. She eyed the space at his crotch as he placed his own glass down next to hers.

"It's not gonna suck itself."

She laughed and looked up at him. He had a genuine smile on his face that time. The first real smile she'd seen from him all night. A healthy row of clean teeth, a dimple…

"Hmm… I think you're right. Let's see what we've got…"

She moved in front of him and placed her hands on his pants to push them away but before she could inch them down he wrapped his meaty hand around the back of her neck and drew her into his chest. His mouth was warm and soft. His tongue tasted like the whisky he'd been drinking.

Letting go of his pants she held onto his biceps as he used his free hand to push her hips against his. Still nice and hard. He ran his tongue over her lips and she moaned into his mouth. He worked his warm lips down to her jaw and then he licked upward on her neck, the wet patch was cool on her skin from the air in the kitchen. He did it again and her knees almost gave out. She hadn't been licked like that before.

He kissed over her clavicle and then drew his tongue over her flesh. Her heart was thrumming quickly and she squeezed his strong arms when he rutted against her.

"You good at sucking cock, Y/n?" He pushed his nose against her jawline and the hot breath from his words scattered over the skin on her neck.

"I want to be," she spoke breathlessly, eyes fluttering closed as he mawed at her throat.

He parted from her neck and looked down at her, half-lidded gaze and spit-slicked lips, "Go on."

Instantly she dropped to her knees as her fingers worked deftly at pulling his pants down and then his underwear. She'd sucked a handful of dicks so she knew a couple of moves.

Getting her hand around his thick shaft proved to be a small challenge. To say he was thick… understatement. Long too. His tip was smooth, mushroomed with ridges along the length that she hoped she'd get to feel later on. His was the kind of cock that women dreamed of.

Looking up at him she licked her palm and used her spit to pump him slowly. Another glob over his tip for good measure. Then she pressed a kiss to the base of him, just over his sac, and screwed her eyes upward to watch his expression as she licked his balls, one side at a time. She wound her tongue all around to wet him before sucking at one side, pulling it into her mouth and he let out a ragged breath, his dark pupils spreading inky until the soft green had almost vanished.

He liked it.

She worked around the other side, sucking him in again and swirling her tongue softly underneath the tender bits. He gripped the counter behind himself.

Pulling off she straightened her back and licked upward, feeling every delicious thick ridge along his shaft until her tongue met his smooth crown. Laving every crevice of his tip, she dipped her tongue into his slit and then ran it under the frenulum before she wetted every inch of his glans.

Her mouth was watering when she parted her lips around him and flitted her gaze upward. He was watching her with a slack jaw as she took him a little deeper. He cradled the back of her head and moaned.

"Just suck the tip…."

She blinked up at him and pulled her lips just over the lip, swirling and suckling around him like he wanted.

"Fuck. Just like that." His hand at the back of her head was easy. He didn't push or pull. It was more like a pleased gesture as his fingertips flexed around her skull gently.

Y/n would have liked to have gone deeper. Wanted to show him her best work. But he seemed rather happy with what she was doing.

She bobbed a couple of times, only to slide her lips back to his tip. Her pace was slow when she began to stroke his length with a little twisting motion.

He was big. She knew she could take more but in a way, she was grateful that that was all he was asking for.

A groan fell from his chest and he bucked forward, his cock slipping down her tongue and she sucked, drawing more of him in as she moved her hands away.

"Goddamnit, you're good."

She took that as permission to go deeper. Relaxing her jaw she closed her eyes and held her breath, pushing down to her limit. She filled her throat with his cock the best she could and gurgled around his tip.

He coughed out a moan and then thumbed at her cheek, "Alright, that's good."

She pulled off of him. His heavy cock aimed right at her face when she sat back on her knees and looked up at him, "I can do better than that."

He laughed and put his hand out for her to take, helping her stand up, "I bet you can. Come on."

Harry kept her hand in his as he led her to his bedroom. It was just past the dark living space and he turned on a floor lamp on the opposite side of the room from the bed. When he turned back toward her he cupped her face and kissed her again.

She pressed her hand into his warm, hard chest and he reached around the back of her dress to pull the zipper downward, his fingers dragging down her skin as he went. His touch sent a tremor down her spine as continued kissing her wetly.

He stepped back, helping her out of her dress until it fell to the floor. His eyes raked over her body and he smoothed his hands over her hips and up to her bra-covered breasts. He stepped in closer, walking her backward toward his bed. He put his hands back on her hips and nudged her to sit before he reached down to lift her leg up by her calf, removing her heels, one at a time.

Y/n's thong was drenched. She stared at him while he placed her shoes side by side at the foot of the bed and then he placed his big palms on her thighs, pushing her legs open, "Lie back."

She let her back hit the mattress as Harry got to his knees on the floor. An arm reached under her thigh as he spread her apart and then she felt her panties being pulled at until her her wet pusslips were right in his face. He groaned and felt a hand slide up the inside of her thigh. He pressed his mouth over her mons and looked up at her before he opened his mouth wide and drew his tongue through her crease making her gasp.

"Get your bra off."

She pushed herself up slightly and worked at the clasp of her bra between moans as Harry continued licking at her pussy. When she pulled her arm through the flimsy material he lifted his head and reached around her back, pulling her closer to the edge of the bed and he sucked a nipple into his mouth.

"Oh, fuck!"

Y/n's finger and her long nails pushed into Harry's hair and scraped at his scalp as he licked and pulled at each nipple. He buried his face between her tits and let out a low sound, like he was murmuring something to her but only her breasts were allowed to hear it.

When he sunk back down he pushed at her so she'd lie back and he started in on her clit, one hand holding her panties to the side as he devoured her glistening cunt.

She kept feeling like she was going to slide off the edge of the bed but Harry's grip on her kept her still. His tongue and his lips were magic as he drew her to her end. She yanked at his hair and babbled his name on repeat as her spine bowed off the bed when she came.

Her chest was still rising and falling heavy when she felt her body being pushed upward. She popped her eyes open and watched him roll a condom over his shaft before he kneed back up onto the bed next to her. He was stark naked. His body was insane. Thick muscle and masculine everything. Tattoos scatter over his arms and chest.

Fuck, she muttered under her breath.

"Flip over, for me," his deep voice was husky as he motioned toward her to move.

She rolled to her stomach and she felt his fingers slide between the band of her panties and her hips as he pulled them down her legs.

"Ass up a little. I want to see all of you, Y/n."

She grinned and turned to look at him over her shoulder as she lifted her hips and spread her thighs. His lips were parted as he grabbed her ass and squeezed, making her cheeks spread apart. He inhaled sharply through his teeth and then dipped in, kissing her pussy from behind before licking upward over her ass.

She squealed quietly and bit her lip, still watching him behind her as he lifted, a lopsided grin on his face. He gazed at her as he fisted the base of his cock and slid the head up and down her soaked folds before he tipped his hips to push in just the tip.

"Gorgeous. Gonna look even better wrapped around cock. You like anal?"

"Never tried it."

He licked his lips and pressed his lips together as he looked at the spot where his dick was pressed against her cunt, "Figured. S'alright. Pussy's my favorite anyway."

"We could try… if you want."

He looked back into her eyes, a cocky smile on his face, "Your little hole would need to be trained. And that takes time. So, there will be no anal tonight. Not gonna try and hurt you. But that's a cute thought."

He canted his hips inward, eyes on hers and her mouth dropped open when she felt her entrance splitting open for him. She was tight, but so slick, it only took a few slow thrusts until he was buried in with a low grunt. He pulled back and then pushed his entire length into the hilt.

"Fuck—fuck!" She cried and stuffed her face into the blankets.

"Too much?"

"No! It's so good. You're just so big…" She began to send her hips back against him and Harry slowly fucked in to match her pace. His eyes were everywhere. On her puss getting split open on his cock, the curve of her lower back, the swell of her ass.

He just knew she'd look so sweet with her ass stuffed too, but good things like that couldn't be rushed which was a shame.

Every thrust was gushy wet. Y/n bubbled out small moans every time his dick brushed deep into her guts. It was better than she imagined. The way he filled her to the brim was going to turn into an addiction. She'd never slept with any man that had her wanting seconds before they'd even finished.

"Oh my god…" she mewled into the comforter.

"Fuck, I know, baby…"

She fit him like a glove, it was perfect. He went in a little faster, balls thudding against her skin rhythmically making her bounce forward as she spread around his girth. When he ground in she arched her back deeply and let out a soft groan, her hands fisted at the blanket and Harry reached around and smeared his fingertips over her clit.

It had her panting and pushing into him feverishly. She'd needed the friction on her throbbing button and he'd found it easily, thick, rough fingerprints slicking back and forth as he rutted in and in. It sent electrical sparks over her limbs.

"Like that? Needs her clit touched? Shit baby, act like you've never been touched by a man right here before…" he plucked at her like he was playing the guitar and she began to fade, her moans getting caught in her chest.

He could feel her walls tightening around him as he drove in deep.

"Fuck, Harry— fuck!"

He grinned as he watched her shudder, "Give it up, Y/n. There you go…"

She began to pulse around him, a constant stream of nonsense falling from her lips as he stroked against her channel and pushed deep into her tummy, his fingers still working her clit with ease.

Just as her body had tipped and oxygen returned to her lungs he pulled out and she felt him taking her hips and turning her around to her back. Harry grabbed her ankles and lifted until each was settled over his shoulders and pushed back inside of her, cock drilling down to her core making her teeth chatter at the way he split her down the middle.

Harry leaned over her, cock buried deep as she watched her pretty face twist up with pleasure. Plapping into her, her tits wobbled as his balls tightened against his body. The harder he plunged in, the more her legs shook. Soon, her ankles had slipped down and her feet hit the mattress as he continued drilling into her. His face was flushed hot, lips parted, muscles tensed.

Reaching up to his neck she smoothed her fingers over his warm skin and he lowered his chest down to hers and kissed her. That filthy tongue ran over her lips and he sloppily sipped at her between sucking at her lips. Her brain had turned to jelly.

She felt his hand on her outer thigh squeezing and brushing as he fucked down into her. "Mmm… fuck, Y/n, m'gonna come…"

He trembled over her, thick thighs pressed down and flexed as he rutted in and in and in, and then… he stilled. A deep, guttural moan vibrated through his chest down into hers.

She sighed when she felt him throbbing, pumping into his condom. Her fingers caressed the muscles over his back and she gasped when he bucked in harshly, once more as he emptied the last of his come into the rubber wrapped around his cock.

He slowed his kisses until they were lazy little pecks and then he looked down at her, his chest heaving. She was already grinning up at him.

"What?"

She blinked her eyes, "That was fun."

He puffed out a breath, "I guess that's a good way to describe it."

Harry was a gentleman as he pulled out slowly and helped her off the bed and led her to his bathroom. He helped her clean up and listened to her tell him about her job —just reminding him that she was an adult after he commented on her being so young again.

When she picked her dress up off the floor and started to step into it, Harry frowned, "What are you doing?"

She stopped and raised her brows. "Getting dressed. Was gonna call an Uber. I'm sure you don't want a stranger in your house all night," she laughed.

Harry pulled at her hand, making her drop her dress, "What kind of men have you been hanging out with that let you leave in an Uber at 2 am? You'll stay here."

She opened her mouth and then closed it in surprise before tilting her head in confusion, "Really? I just assumed—"

"You'll stay the night here. There's no way in hell you're getting an Uber at this time of night. It's dangerous."

She grinned and shrugged, "Well then… can I have a shirt or something to sleep in?"

He placed his warm hands on her hips, "You can have a t-shirt if you like. I prefer to sleep naked myself."

"Oh yeah? I usually do too as a matter of fact."

He held her out in his arms and eyed her naked frame, "Looks like we're both good to go then. We'll get you sorted in the morning. I'll give you a ride home then."

"I think you just want to keep me here with you," she chuckled.

Harry shook his head and released her hips before he popped her on the bottom with his palm. She bleated out a laugh.

"Get your ass in bed before I change my mind."

"Yes, sir."

. .

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[gurugirl]

DILF | older!harry

MAIN MASTERLIST

Summary: Y/n meets an older man at a bar and she's not taking no for an answer. Harry likes her persistence.

A/N: This was requested + this! Also, please think before you judge Y/n. She is very bold and confident in this. Maybe even a little pushy but Harry likes it (even if at first he doesn't give that impression). Also he's single so this isn't cheatrry!

Word Count: 6,580

Warning: age gap, smut, alcohol consumption (light)

. .

"That one. Total dilf. He looks grumpy. Bet you can't crack him."

Y/n laughed at her friend and looked down at her red-painted nails before narrowing her gaze on the attractive older man who was seated at the corner of the bar alone. He was nursing a whisky and he did look rather sullen. Unapproachable even.

"Why him?"

"Because he's hot. And I'm curious to see if you can get him to smile at least," Warren raised her brows, "I dare you."

Y/n tilted her head and assessed him. He was nice and big, taking up a decent amount of space at the bar, broad shoulders and back hunched as he leaned his muscular forearms on the wood of the bar top. Meaty hands placed on either side of his lowball glass. Thick brown waves on top of his head with a bit of silver coming in at the temples. But the handsome features on his face really set him apart. His granite jawline gave way to stubble that stretched over his skin and shaded in the spaces around his pink lips.

If she could "crack" him she wasn't sure she'd want just a smile. He looked yummy enough to eat.

Drinking down the last of her martini she pointed at Warren and then Tara, "Fine. Give me twenty minutes and I'll have him eating from the palm of my hand."

Tara laughed, "If you say so…"

She placed her heeled feet down on the floor and brushed her hands over her dress, "Oh, I do say so. Just watch and learn, ladies."

Y/n wasn't quite that confident, but she wasn't about to say no to dare. And she could hold her own when it came to flirting. She liked getting a little attention and if she could garner this one's interest it might be fun.

She sauntered up to the bar behind the man and noticed the way his t-shirt stretched over his lats and tapered loosely down at his waist. The guy was fit. And lucky her, there was an open stool next to him.

Sliding onto the seat she waved at the bartender to order another drink. She'd need all the courage she could get, in whatever form she could get it.

Tapping her long nails on the lacquered wood she felt nerves thrumming through veins before turning toward the man finally. He hadn't seemed to take note of her yet, which honestly was unusual in most cases. Maybe she thought too highly of herself but men tended to notice her right away. She appreciated the challenge, though.

Reaching her hand into his space to greet him, she pushed down her nerves to sound steady as she spoke, "I'm Y/n."

She watched his brow furrow as he turned to look at her hand and then up at her eyes, his expression, which she expected would soften once he looked at her, was unamused. A single light overhead lit the tops of their heads as a shadow cast over the side of his face and he didn't make a move to shake her hand, "And I'm old enough to be your dad."

A surprised scoff fell from her lips as she moved her hand away from him. She wiggled in her seat and crossed her leg over her thigh toward him, gulping down the initial rejection with as much grace as she could muster, "I think you're jumping to conclusions about my intentions. But so what if you're older than me? I don't mind. We're both adults, right?"

An unimpressed grunt rumbled from his throat before he took another sip of his whisky and he looked away from her toward the TV that hung not far away from where they sat.

The bartender placed her olive martini down on the bar in front of her, "It'll be on Y/n Y/l/n. I already have an open tab."

A sip of the salty drink felt warm down her throat. So he was going to be a bit tough to crack. She turned to look at her friends who were grinning in her direction.

Straightening her back to feel more confident she tried again, "So you're not gonna tell me your name even?"

Without looking at her, he licked his lips and ticked his jaw, "Y/n, I think it's past your bedtime."

She smiled at that. He'd said her name, which meant he'd been listening, "My bedtime is whenever I say it is, not when some grouchy stranger says."

He puffed out an amused laugh through his nose, "I am a stranger. Which means you should be cautious, little girl. Your dad didn't teach you about things like that?" He turned to look down at her again, and that time she saw the soft green color of his eyes as the light hit his face just right.

But now she was really determined. She smiled brightly at him and let her eyes coast over his tattooed arm and then back up to his face, "Are you telling me you're dangerous?"

He still didn't smile as he shook his head like he was surprised by her gall, "Do your parents know what you're up to tonight?"

"I'm 24. Graduated from college, live on my own, pay my bills, have a full-time job. You seem to be awfully worried about my parents. I can take care of myself just fine."

Just then another person sat down next to the man Y/n was trying to whittle away at. He poked his elbow at him, "Who's this?"

"Don't know. Someone who's about to go back to her table with her little girlfriends."

Biting her lip she traced the rim of her martini glass with her fingertip, keeping her eyes set on the handsome tattooed one, "Not even a smile. Just one? Please?"

"Like I already said, I'm way too old for you."

The other man leaned over and reached to tap Y/n's shoulder, "Hey. Forget about Harry, here. You can bring me home with you if you're looking for a daddy tonight."

She frowned and looked him up and down to asses. He was late 40s perhaps, wearing a local band t-shirt, ripped jeans, and a backward cap to make himself appear a little more youthful. "No thanks. You'd know if I was interested in you."

Harry bit the inside of his cheek to stop himself from smiling at her retort. She was definitely too young but he liked her spunk.

"Now, Harry…" she said his name slowly as she leaned a little closer, "I've got your name thanks to your friend. Can I have a smile?"

"Why?" He stared down at her, the caress of his gaze felt infinite and she found her skin convecting in its wake. He might be hard to crack but this one would be worth it, she determined.

She sighed and slid her finger dangerously close to his wrist as he looked down at her nail and watched her trail it near his arm, "I just hoped to see you smile is all. Too handsome to have such a sour scowl on your face."

"And you're hardly old enough to be so confident to walk up to a strange man at a bar."

She laughed and tilted her head, "You planning on doing something bad to me, Harry?"

And that. That pulled a reaction out of him that spread over his features slowly as he shook his head in disbelief, "Darlin', you wouldn't be able to handle me."

Her eyes widened slightly. Now she was definitely not giving up. Y/n wasn't one to fail and Harry might be making her work hard for it but she couldn't imagine it wouldn't be worth it in the end.

"Is that a challenge or something?" She softly scraped her nail over his tattooed wrist and Harry watched her red nail work over his skin.

His resolve was fading fast. She could tell he wasn't going to keep denying her. And why should he? If he was single, which he appeared to be, what was the harm in having a little fun with someone younger? Y/n didn't mind. And he certainly shouldn't either.

"If it were a challenge you'd know it. Lots of other guys here, Y/n. Go enjoy your night with someone closer to your own age."

She sighed in annoyance. But he hadn't moved his arm away from her and she was going to take that as a sign.

Dragging the toe of her shoe into his shin she grinned, "I don't want to enjoy my night with someone my own age. Not tonight anyway. I think you've convinced me that I need to test out this theory of yours. That you think I can't handle you. Cause I bet I can."

With his eyes piercing into hers, he took another sip of his drink. She thought she might have just convinced him to give her a smile at the very least because it looked like he was weighing his options. And if she could get him to smile she might have luck with the rest.

He tilted his chin upward for a moment, eyes aimed at the ceiling like he was calling on a higher power for strength, "Go back to your friends, Y/n. Any other man here would love to have your company."

"But you wouldn't love to have my company?"

"I mean… I'm still here," the other man raised his hand and leaned into Harry, "Honey we could have so much fun. Any man who'd turn you down is either battin' for the other team or more likely," he chuckled and pushed his shoulder into Harry's teasingly, "He can't get it up anymore."

Y/n's mouth dropped open at that and Harry turned to look at the man. She wished she could see the look on his face, "Sit the fuck back down, John. She already told you she's not interested in you."

"Yeah, and you're not interested in her so what's it matter to you? Look at her, Harry. Practically begging you. Young and bubbly… Tight—"

Harry's hand covered John's throat as he pushed him away, nearly making his stool topple over, "Get the fuck outta here. You had too much whisky tonight."

"Aww… come on Harry… I was just jokin'!"

She watched as he stood from his stool and looked down at John, "And you thought that was funny? You like making jokes about women like that?"

The man put his hands up in surrender, "I'm out. Here…" he threw a wad of cash on the bar top before he moved past Harry and then looked at Y/n, "My apologies if I offended you."

They watched as John left the bar quickly and then Harry sat back down before he waved at the bartender and signaled for the check, "Just the one whisky neat."

"You're leaving already? Night's still young, Harry."

He sucked at his teeth as he scraped his gaze over her face and down to her cleavage. She smiled when she watched the path his eyes had taken.

The bartender handed him the bill and Harry leaned over to pull his wallet from his back pocket.

She scooted closer to him, "You headed home?"

He nodded, but not necessarily in answer to her question, it was more of an appraisal kind of nod. He was still silent as he pulled cash out of his wallet.

"Thanks for that, by the way. I'm sure John's a nice guy and all but he's not really my type. And I'm sure he was wrong about you."

That got his attention. Harry flicked his gaze back to hers, "Wrong about me?"

She smiled, "The part where he said you couldn't get it up. You're not that old. I'm sure you still can. Right?"

He clenched his jaw and breathed out of his nostrils like he couldn't believe she'd asked him such a thing. He handed the bartender his cash with a nod before he stood up from his stool.

"Huh. Since you're so quiet about it maybe he was right," she goaded, pressing her lips together to flatten her smile as she looked up at him through her lashes.

Harry placed a palm down on the bar top next to her hand and leaned over her, "You're out of your depth here, Y/n."

"Now, you don't really know that do you? Just because I'm younger than you doesn't mean I don't know what I'm doing."

"You're awfully pushy. Not used to hearing no, are you?"

Y/n watched as the edge of his mouth lifted in amusement and she widened her eyes and pointed, "You're almost smiling."

He shook his head and looked around the bar before pinning his gaze back to hers, "I hope you enjoy the rest of your night. But your luck has run out with me, princess."

Harry stood to his full height and Y/n decided to try one last time, "So it's true then. What he said."

He stopped and turned to look back at her, a slow burning heat behind his gaze, "Couldn't be further from the truth."

She smiled and slid off her stool to stand in front of him. His height was impressive, "Prove it."

The line of his jaw hardened, turning his cheekbones into slashes of tension. His eyes simmered as he weighed his options. Finally, a hint of a smile stretched over his mouth. A small one, but still.

"I don't need to prove anything to silly little girls."

"Good thing I'm not a silly little girl. I'm a grown woman, Harry."

Y/n knew she was pushing it. She'd never needed to throw herself at any man before. But because of that, she wasn't used to rejection either. Maybe it was a good lesson for her ego. She knew her big fault was how entitled she could act sometimes. But that was partly thanks to how she was raised. It's better to act like a man to get what you want in life, her dad told her. And so far, that had been true. Some women balked at her confidence and her bold attitude. She wasn't demure or sweet enough. And men would often refer to her as a bitch or say that she was trying too hard.

She'd work on her ego another time. But right now? She was focused on winning this battle.

"What do you want with someone like me anyway? Hm? I'm old, Y/n. What's in it for you?"

Blinking her eyes she shook her head, "You're not old, first of all. Secondly, you're really attractive. It doesn't need to go much deeper than that, does it? I just think you're handsome. And I do kind of like a challenge."

"I can see that you like a challenge. It's the only reason I haven't walked out that door yet. Kind of relentless."

She smiled, "So it's working?"

Another half-smile worked its way up his mouth as he laughed in disbelief, "Are you surprised that it is?"

His pupils coasted over her figure and then back up to her face. The warmth of his gaze singed her skin like an open flame.

"I guess I just didn't know how difficult it'd be with you."

He licked his lips, "Difficult. You have no idea. But looks like you're about to find out. Go tell your friends what's going on. Meet me out front."

Y/n watched him turn and walk away. She was shocked. For a minute she thought he wasn't going to go for it at all.

Shaking off the sudden surprise of having gotten to him she settled up with the bartender and then stopped at the table with her friends. They were just about to give her condolences for having oversold her ability but she interrupted. "He's waiting for me outside. Location is on. Don't wait up!"

Harry was leaning against a black car in the parking lot when she stepped out of the doors. The moment he saw her he pushed himself off the car and opened the passenger door for her.

It was going to be tricky to maintain the kind of confidence she'd been feigning with him up until then but there was no part of her that didn't want to find out what he could show her.

She watched as Harry sat down in the driver's seat and started up his car. He took up too much space in the seat. His big hand wrapped around the leather steering wheel while his other encased the shift stick. Even the way he drove was turning her on.

She was pleased that she'd wormed her way under his skin and that he'd given in. She'd try her best to make it worth his while. Reaching across the console she put her hand on his thigh and he glanced down quickly before setting his gaze back on the road.

Now, Harry had slept with younger women a couple of times. He generally preferred someone closer to his age because he liked the confidence and experience that came with age. Women in their 20s were often in a different stage of life and that was fine –normal even, but it just usually wasn't a match for him. Not sexually and not mentally.

But Y/n was unusually confident for being so young. Persistent. He liked it, he couldn't lie. Whether or not she really had much else going for her beyond confidence, he guessed he'd find out. Well, she was very cute too. She did have that in her favor.

And Y/n at least seemed like she knew what she wanted. It was flattering as well. Being approached by such a pretty young thing. He figured the moment he told her to go back to her friends she'd give up but she was just fiery enough that she wasn't deterred.

When she ran her nail over his wrist he knew he was screwed. She was just close enough that he could smell her perfume and then she nudged her shoe into his shin and all he could think about was that she really wanted to be shown a good time and if anyone could it was him.

Harry knew his way around a woman's body. They were all different and he liked finding all the buttons and things that made them purr. In his experience, though, the younger the woman, the less she knew her own body. He didn't know if Y/n was just talking a big game but he was about to find out.

He stayed quiet as she ran her hand down his thigh and he shifted as the car accelerated past the green light. He'd see if she'd do anything with her hand but maybe she'd just pet at him like a novelty toy. He didn't expect—

"This is okay?" She asked him, her tone sultry as she palmed at his crotch.

He licked his lips, "Have at it."

His cock fattened up nicely with not much effort on her part. Proof that he definitely could get it up. Plucking at his button she looked from his face to her fingers as she leaned further over the console to reach her hand into his open pants to help him with the awkward angle of his dick. He seemed to appreciate that as he shifted under her palm.

Rubbing over his heather grey briefs she peeled down the elastic band the slightest to get a peek. The dark shade of pink on his tip matched the muted raspberry of his lips. She slid the pad of her middle finger over the slit and he softly inhaled through his teeth.

She wouldn't be able to give him roadhead like she wanted. It was impossible with the stick shift in the way. But she could wrap her fingers around his shaft and feel him under her palm until they got wherever they were going.

"Mmm… It's so big, Harry. Knew you would be. Might be the biggest I've seen in person. Can't tell yet, though. Have to wait to see when we've got these off."

Harry pushed a laughed breath through his nose. She was a bold thing. Her assertiveness was a turn-on. He didn't like meek and shy. Not when it came to sex.

When she spit into her palm and smeared it down his length, the best she could, he parted his lips and stepped on the gas. She was already exceeding any expectations he had for her. Maybe she'd prove him wrong.

Her nail scraped the underside of him and she moaned, "Really want it in my mouth."

He gulped harshly and ticked his jaw, "Just be patient. I'll let you put it in your mouth soon enough."

"And where are we going? Your place?"

He nodded, "Just a few minutes away."

She squeezed around him and pulled upward slowly. She knew already, he was well above average and she was going to have to work to give him a proper blowy.

His house was a one story, the driveway at the front with a garage attached. He lifted his hand and pushed on a device that was clinging to his sun visor and the garage door began to open. There was a covered motorcycle along the back wall and then the garage door closed after he shut off the engine.

She moved her hand away and unbuckled herself as he got out. When she reached down to pick up her little purse she realized her panties were already wet. She grinned as she stepped out, adjusting her dress before closing the door, and then followed behind him as he led her into a dark hallway.

When he turned on the lights she took it all in. Hardwood floors led into a dining area and then a kitchen. Hung on the walls were photos of himself with two children and then more framed photos with just the kids.

"Do you have kids?"

"I do. Boy and a girl. 7 and 10."

"You're not married are you?"

He laughed, "If I were you'd have known. Wouldn't have been out in the first place if I had a wife waiting for me at home."

She nodded as he turned on the kitchen light and pulled out two glasses before filling them with water.

"Divorced?"

Handing her a glass he squinted, "Yes."

She took a sip. He was a man of few words she'd gathered. She looked around the kitchen. Wood cabinets, an outdated laminate countertop, stainless steel appliances. The space could use some updating but it was large and he had a big pantry.

Sitting the glass down on the counter she watched him closely. His pants were still unbuttoned. She eyed the space at his crotch as he placed his own glass down next to hers.

"It's not gonna suck itself."

She laughed and looked up at him. He had a genuine smile on his face that time. The first real smile she'd seen from him all night. A healthy row of clean teeth, a dimple…

"Hmm… I think you're right. Let's see what we've got…"

She moved in front of him and placed her hands on his pants to push them away but before she could inch them down he wrapped his meaty hand around the back of her neck and drew her into his chest. His mouth was warm and soft. His tongue tasted like the whisky he'd been drinking.

Letting go of his pants she held onto his biceps as he used his free hand to push her hips against his. Still nice and hard. He ran his tongue over her lips and she moaned into his mouth. He worked his warm lips down to her jaw and then he licked upward on her neck, the wet patch was cool on her skin from the air in the kitchen. He did it again and her knees almost gave out. She hadn't been licked like that before.

He kissed over her clavicle and then drew his tongue over her flesh. Her heart was thrumming quickly and she squeezed his strong arms when he rutted against her.

"You good at sucking cock, Y/n?" He pushed his nose against her jawline and the hot breath from his words scattered over the skin on her neck.

"I want to be," she spoke breathlessly, eyes fluttering closed as he mawed at her throat.

He parted from her neck and looked down at her, half-lidded gaze and spit-slicked lips, "Go on."

Instantly she dropped to her knees as her fingers worked deftly at pulling his pants down and then his underwear. She'd sucked a handful of dicks so she knew a couple of moves.

Getting her hand around his thick shaft proved to be a small challenge. To say he was thick… understatement. Long too. His tip was smooth, mushroomed with ridges along the length that she hoped she'd get to feel later on. His was the kind of cock that women dreamed of.

Looking up at him she licked her palm and used her spit to pump him slowly. Another glob over his tip for good measure. Then she pressed a kiss to the base of him, just over his sac, and screwed her eyes upward to watch his expression as she licked his balls, one side at a time. She wound her tongue all around to wet him before sucking at one side, pulling it into her mouth and he let out a ragged breath, his dark pupils spreading inky until the soft green had almost vanished.

He liked it.

She worked around the other side, sucking him in again and swirling her tongue softly underneath the tender bits. He gripped the counter behind himself.

Pulling off she straightened her back and licked upward, feeling every delicious thick ridge along his shaft until her tongue met his smooth crown. Laving every crevice of his tip, she dipped her tongue into his slit and then ran it under the frenulum before she wetted every inch of his glans.

Her mouth was watering when she parted her lips around him and flitted her gaze upward. He was watching her with a slack jaw as she took him a little deeper. He cradled the back of her head and moaned.

"Just suck the tip…."

She blinked up at him and pulled her lips just over the lip, swirling and suckling around him like he wanted.

"Fuck. Just like that." His hand at the back of her head was easy. He didn't push or pull. It was more like a pleased gesture as his fingertips flexed around her skull gently.

Y/n would have liked to have gone deeper. Wanted to show him her best work. But he seemed rather happy with what she was doing.

She bobbed a couple of times, only to slide her lips back to his tip. Her pace was slow when she began to stroke his length with a little twisting motion.

He was big. She knew she could take more but in a way, she was grateful that that was all he was asking for.

A groan fell from his chest and he bucked forward, his cock slipping down her tongue and she sucked, drawing more of him in as she moved her hands away.

"Goddamnit, you're good."

She took that as permission to go deeper. Relaxing her jaw she closed her eyes and held her breath, pushing down to her limit. She filled her throat with his cock the best she could and gurgled around his tip.

He coughed out a moan and then thumbed at her cheek, "Alright, that's good."

She pulled off of him. His heavy cock aimed right at her face when she sat back on her knees and looked up at him, "I can do better than that."

He laughed and put his hand out for her to take, helping her stand up, "I bet you can. Come on."

Harry kept her hand in his as he led her to his bedroom. It was just past the dark living space and he turned on a floor lamp on the opposite side of the room from the bed. When he turned back toward her he cupped her face and kissed her again.

She pressed her hand into his warm, hard chest and he reached around the back of her dress to pull the zipper downward, his fingers dragging down her skin as he went. His touch sent a tremor down her spine as continued kissing her wetly.

He stepped back, helping her out of her dress until it fell to the floor. His eyes raked over her body and he smoothed his hands over her hips and up to her bra-covered breasts. He stepped in closer, walking her backward toward his bed. He put his hands back on her hips and nudged her to sit before he reached down to lift her leg up by her calf, removing her heels, one at a time.

Y/n's thong was drenched. She stared at him while he placed her shoes side by side at the foot of the bed and then he placed his big palms on her thighs, pushing her legs open, "Lie back."

She let her back hit the mattress as Harry got to his knees on the floor. An arm reached under her thigh as he spread her apart and then she felt her panties being pulled at until her her wet pusslips were right in his face. He groaned and felt a hand slide up the inside of her thigh. He pressed his mouth over her mons and looked up at her before he opened his mouth wide and drew his tongue through her crease making her gasp.

"Get your bra off."

She pushed herself up slightly and worked at the clasp of her bra between moans as Harry continued licking at her pussy. When she pulled her arm through the flimsy material he lifted his head and reached around her back, pulling her closer to the edge of the bed and he sucked a nipple into his mouth.

"Oh, fuck!"

Y/n's finger and her long nails pushed into Harry's hair and scraped at his scalp as he licked and pulled at each nipple. He buried his face between her tits and let out a low sound, like he was murmuring something to her but only her breasts were allowed to hear it.

When he sunk back down he pushed at her so she'd lie back and he started in on her clit, one hand holding her panties to the side as he devoured her glistening cunt.

She kept feeling like she was going to slide off the edge of the bed but Harry's grip on her kept her still. His tongue and his lips were magic as he drew her to her end. She yanked at his hair and babbled his name on repeat as her spine bowed off the bed when she came.

Her chest was still rising and falling heavy when she felt her body being pushed upward. She popped her eyes open and watched him roll a condom over his shaft before he kneed back up onto the bed next to her. He was stark naked. His body was insane. Thick muscle and masculine everything. Tattoos scatter over his arms and chest.

Fuck, she muttered under her breath.

"Flip over, for me," his deep voice was husky as he motioned toward her to move.

She rolled to her stomach and she felt his fingers slide between the band of her panties and her hips as he pulled them down her legs.

"Ass up a little. I want to see all of you, Y/n."

She grinned and turned to look at him over her shoulder as she lifted her hips and spread her thighs. His lips were parted as he grabbed her ass and squeezed, making her cheeks spread apart. He inhaled sharply through his teeth and then dipped in, kissing her pussy from behind before licking upward over her ass.

She squealed quietly and bit her lip, still watching him behind her as he lifted, a lopsided grin on his face. He gazed at her as he fisted the base of his cock and slid the head up and down her soaked folds before he tipped his hips to push in just the tip.

"Gorgeous. Gonna look even better wrapped around cock. You like anal?"

"Never tried it."

He licked his lips and pressed his lips together as he looked at the spot where his dick was pressed against her cunt, "Figured. S'alright. Pussy's my favorite anyway."

"We could try… if you want."

He looked back into her eyes, a cocky smile on his face, "Your little hole would need to be trained. And that takes time. So, there will be no anal tonight. Not gonna try and hurt you. But that's a cute thought."

He canted his hips inward, eyes on hers and her mouth dropped open when she felt her entrance splitting open for him. She was tight, but so slick, it only took a few slow thrusts until he was buried in with a low grunt. He pulled back and then pushed his entire length into the hilt.

"Fuck—fuck!" She cried and stuffed her face into the blankets.

"Too much?"

"No! It's so good. You're just so big…" She began to send her hips back against him and Harry slowly fucked in to match her pace. His eyes were everywhere. On her puss getting split open on his cock, the curve of her lower back, the swell of her ass.

He just knew she'd look so sweet with her ass stuffed too, but good things like that couldn't be rushed which was a shame.

Every thrust was gushy wet. Y/n bubbled out small moans every time his dick brushed deep into her guts. It was better than she imagined. The way he filled her to the brim was going to turn into an addiction. She'd never slept with any man that had her wanting seconds before they'd even finished.

"Oh my god…" she mewled into the comforter.

"Fuck, I know, baby…"

She fit him like a glove, it was perfect. He went in a little faster, balls thudding against her skin rhythmically making her bounce forward as she spread around his girth. When he ground in she arched her back deeply and let out a soft groan, her hands fisted at the blanket and Harry reached around and smeared his fingertips over her clit.

It had her panting and pushing into him feverishly. She'd needed the friction on her throbbing button and he'd found it easily, thick, rough fingerprints slicking back and forth as he rutted in and in. It sent electrical sparks over her limbs.

"Like that? Needs her clit touched? Shit baby, act like you've never been touched by a man right here before…" he plucked at her like he was playing the guitar and she began to fade, her moans getting caught in her chest.

He could feel her walls tightening around him as he drove in deep.

"Fuck, Harry— fuck!"

He grinned as he watched her shudder, "Give it up, Y/n. There you go…"

She began to pulse around him, a constant stream of nonsense falling from her lips as he stroked against her channel and pushed deep into her tummy, his fingers still working her clit with ease.

Just as her body had tipped and oxygen returned to her lungs he pulled out and she felt him taking her hips and turning her around to her back. Harry grabbed her ankles and lifted until each was settled over his shoulders and pushed back inside of her, cock drilling down to her core making her teeth chatter at the way he split her down the middle.

Harry leaned over her, cock buried deep as she watched her pretty face twist up with pleasure. Plapping into her, her tits wobbled as his balls tightened against his body. The harder he plunged in, the more her legs shook. Soon, her ankles had slipped down and her feet hit the mattress as he continued drilling into her. His face was flushed hot, lips parted, muscles tensed.

Reaching up to his neck she smoothed her fingers over his warm skin and he lowered his chest down to hers and kissed her. That filthy tongue ran over her lips and he sloppily sipped at her between sucking at her lips. Her brain had turned to jelly.

She felt his hand on her outer thigh squeezing and brushing as he fucked down into her. "Mmm… fuck, Y/n, m'gonna come…"

He trembled over her, thick thighs pressed down and flexed as he rutted in and in and in, and then… he stilled. A deep, guttural moan vibrated through his chest down into hers.

She sighed when she felt him throbbing, pumping into his condom. Her fingers caressed the muscles over his back and she gasped when he bucked in harshly, once more as he emptied the last of his come into the rubber wrapped around his cock.

He slowed his kisses until they were lazy little pecks and then he looked down at her, his chest heaving. She was already grinning up at him.

"What?"

She blinked her eyes, "That was fun."

He puffed out a breath, "I guess that's a good way to describe it."

Harry was a gentleman as he pulled out slowly and helped her off the bed and led her to his bathroom. He helped her clean up and listened to her tell him about her job —just reminding him that she was an adult after he commented on her being so young again.

When she picked her dress up off the floor and started to step into it, Harry frowned, "What are you doing?"

She stopped and raised her brows. "Getting dressed. Was gonna call an Uber. I'm sure you don't want a stranger in your house all night," she laughed.

Harry pulled at her hand, making her drop her dress, "What kind of men have you been hanging out with that let you leave in an Uber at 2 am? You'll stay here."

She opened her mouth and then closed it in surprise before tilting her head in confusion, "Really? I just assumed—"

"You'll stay the night here. There's no way in hell you're getting an Uber at this time of night. It's dangerous."

She grinned and shrugged, "Well then… can I have a shirt or something to sleep in?"

He placed his warm hands on her hips, "You can have a t-shirt if you like. I prefer to sleep naked myself."

"Oh yeah? I usually do too as a matter of fact."

He held her out in his arms and eyed her naked frame, "Looks like we're both good to go then. We'll get you sorted in the morning. I'll give you a ride home then."

"I think you just want to keep me here with you," she chuckled.

Harry shook his head and released her hips before he popped her on the bottom with his palm. She bleated out a laugh.

"Get your ass in bed before I change my mind."

"Yes, sir."

. .

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