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gurugirl · 6 days ago

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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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jarofstyles · 2 months ago

Text

Merlot

Hello my lovely ducklings. I promised a good age gap DILF sorta thing and I’m here to hand ‘em over. He’s getting some silver at the temples and she’s loving every second of it. Let me know what you think 🍷

Check out our Patreon for early access to the second part and 200+ exclusive writings

WC- 8k

Warnings- age gap, dilfrry, smut, oral (m + f receiving) unprotected sex (please wrap it up irl), exhibitionism, daddy kink if you squint, and all the fun stuff.

“I hate to ask this cliche question, and it absolutely pains me to ask in such an uncouth way- but do you come here often?” Peeking over the rim of the glass, amber liquid brushed his top lip and the ice cubs clanked as the smoky liquor hit his tongue.

God knew what he was doing- the girl in front of him looked too young for him, but she had struck up the conversation first. Commenting on his silver lion’s head ring and asking where he’d gotten it, wide eyed and eager as she looked up at him with that pretty pout and mascara coated lashes. Perhaps it was the crippling loneliness of divorce, maybe it was the hint of a buzz of his second drink, or even a hint of desperation that had him continuing the conversation with the younger woman as she took the bar stool in front of him- but she seemed receptive. Leaning into the conversation and keeping eye contact, she played into him.

"Cliches can be cute sometimes." She laughed as she placed her own glass down, now empty. "I don't, no. I'm not one for the whole going out thing. Not anymore. I was in uni, but I think as soon as you graduate they take away your tolerance card." Rolling her eyes playfully she felt a lick of satisfaction in getting a chuckle out of him. "And what about you? Do you like to come to bars with overpriced drinks to talk to random people who decide to invade your bubble to ask where your pretty jewelry is from?"

"Well, I can't say I make a habit of it, but sometimes a man needs to escape the responsibilities of reality- and as much as I adore my pets, I think they’re tiring of hearing my voice.” He shook his head as he flexed his fingers, looking back down at the conversation starter. Pretty eyes met his own. It had been so long since he felt flustered but she had done a pretty good job at making him feel a little off kilter in the best way. A break from the mundane.

“I’ll have to agree with you on them revoking your tolerance once you exit uni. Though I will say it’s a blessing in disguise. I wasn’t terribly into partying in my last year, considering I’d started getting awful hangovers. Almost like s’bad for you, or something.” He teased, leaning against the bar top. It was clear that they’d shifted closer to each other through their conversation and he tried to not get his hopes up, but he sort of did feel like she was giving him… those sort of eyes. “I don’t want to keep you from your friends, though.”

“You’re not.” She said simply, looking up at him. Usually, facial hair wasn’t something she considered much at all. Not many around her wore it, but she had to say the longer she looked at him, the more she liked it. It was just… masculine. Rugged, in a way, but he kept it groomed. This man was interesting all around, with pretty rings and a deep raspy voice, seafoam eyes and a little tiny gray streak starting near his temple. God, that was hot. “I’m plenty happy talking to you.”

His heart skipped a beat as she looked up at him, those eyes sparkling with something he hoped was interest, but at the very least looked like genuine intrigue. Nothing about their encounter led to her feeling otherwise. It was a nice change, feeling the ease of a conversation flow even if he stumbled on words when he accidentally looked down at her lips.

Fuck it.

He reached out, gently brushing a stray lock of hair behind her ear, his fingers lingering on her cheek. "I’m glad t’hear that. You're very easy to talk to." he said, his voice low and warm. The risk was there, initiating a bit of touch, but he had fo test to waters. See where this was headed. Was she looking for a safe haven? A reliable guy who didn’t look like a creep (hopefully), someone to buy her drinks as she pitied the older man at the bar, or… was this headed the direction the heat in his belly desperately wanted.

“Am I?” Her head tilted slightly, smile slightly shy but making no effort to move from where his fingers hovered slightly. “I do get told I have problems knowing when to shut up and let things be quiet, so I suppose that tracks. It can be nice in conversations.” Especially when he had seemed slightly apprehensive of her at first and now warmed up. “You’ve got a nice voice. It’s nice to talk to you.”

"Well, I suppose we'll just have to keep talking, then." He said softly, his voice growing even warmer as he leaned in closer, his eyes flicking back down to her lips briefly before returning to her eyes.

“I agree.”

Y/N could be considered bold at times, but she liked that he was showing some effort- some interest. It was give and take, push and pull, a fun little game as she was given a perfect chance when someone else approached the bar top from behind Harry. “Oop- come ‘ere.’ She laughed, gently tugging him in as her ankle hooked around the back of his knee to tug him into her. “Someone’s tryn’ to make an order.”

Now he was closer than she had anticipated, stood between her thighs as she sat on the barstool with her leg wrapped around his. “Sorry. Didn’t mean to get in your space.” The girl could feel his body heat. Fuck, he smelled so good. None of that… the familiar cheap colognes and aftershaves she was used to, not was it overpowering. Harry smelled expensive and spicy with some sort of leathery vanilla and she had to wonder what it was. "You smell really good..."

"No, no, it's fine..." He said softly, his voice trailing off as he looked down at her, their faces inches apart. He didn't move away, instead, he leaned in even closer, his hand resting on her knee. “Thank you.” The heat felt a little overwhelming in his cheeks. Pathetic to be a grown man blushing over such a simple compliment but he was so close to her now, body head radiating off of her and she smelled equally as good. “Um, so do you.”

He breathed in deeply, taking in her scent. It was a unique blend of floral notes, with a hint of citrus and a sweet, vanilla-like undertone. It was feminine, youthful, and intoxicating. Sweet and fresh. It didn’t choke him in floral and musk like the women who had been after him since his signature had barely dried on his divorce papers, but something that he vaguely remembered from his own days around her age. Perhaps that was a sign he should back off, but he couldn’t. He felt himself getting lost in the scent, his head spinning slightly as he continued to breathe her in.

His hand on her knee nearly burned but she relished in the feeling, tossing her hair over her shoulder as she smiled slightly at him. It was her first time attempting something like this. Older men were always a thing for her, a desire, but never one she felt bold enough to go for. Now, though, she wondered why she had waited. The feeling in her stomach and the delicate way she felt under his touch was something that had her nearly giddy.

“I like the mustache.” She pointed to it. “It’s a mature look. In a good way.” Of course she didn’t want to offend him, make him feel like she was calling him old. “Guys I’m around usually can’t pull it off. But you do.” Braving a touch, she let her fingers run over his jaw and felt a slight bit of scruff. “Are y’gonna go for a full beard? Or no?”

"Maybe..." Harry murmured, leaning into her touch. "Depends on how well it's received..." The joke was cracked softly, his eyes fluttering closed briefly as she touched his face. He let his hand slide a little higher up on her thigh, squeezing gently. "Thank you for the compliment though. Was hoping it wouldn’t be a bad thing cause I noticed y’looking at it.”

“Mm, I was. It’s nice.” Sexy. Her eyes felt heavy as she watched his lips curl in a slight smile. “ I’m assuming that there’s no missus at home?” She asked lightly. “You don’t seem like a cheater, Harry.” It was a tease, but he didn’t wear a ring on his ring finger. Usually she never gave men the benefit of the doubt but selfishly, she wanted to be right so she wouldn’t feel guilty about imagining her inner thighs raw from beard burn later tonight.

"No missus." He confirmed, his thumb rubbing small circles on her thigh as he opened his eyes to look at her. "Just me, and the office. I've been too busy to think about dating, let alone finding someone serious." He admitted honestly, his gaze lingering on her face. "I mean, I was married. Briefly." He said, his expression growing slightly somber. "But that's over now. It didn't work out." He shrugged, trying to downplay it, even though the divorce had been messy and painful. "What about you? Boyfriend at home?"

“I’m sorry it didn’t work out.” She frowned. It wasn’t something she’d pry on because she could see it bothered him a bit, but that didn’t mean she wasn’t curious. Nor that she didn’t feel bad. “I’m single, thank god. My last boyfriend was a complete prick.” Her nose wrinkled in disgust. “Cheated on me a few times on a boys holiday. Was stupid enough to post with other girls and think people wouldn’t send it to me just because he hid stories from me. but it was a relief, anyways.” It sounded cold, callous maybe, but it was the truth. “It’s just me now as I figure out what to do.”’

"He sounds like an idiot." He grumbled, his hand tightening lightly on her thigh. "You're too good for that." He paused, his eyes flicking over her features. "What do you mean, figure out what to do? Like, with life?"

“Yeah. Career wise mostly. I think I want to do writing but it’s been hard to tell lately. I do that part time and then work at a cafe as a waitress and pick up shifts when I need the money. I’m tired all the time so it’s taking me longer to simply sit down and figure out 100% what I want to do but, that’s life.” She shrugged. “So I get suckered into going out to bars with my coworkers and getting a buzz so I go up to a handsome man and demand to know where his ring is from, so it suppose it isn’t all bad.”

"Writing, huh?" There was intrigue in his voice as he took in her answer. The compliment wasn’t lost on him, and it fueled that bolder part of him that wanted to break out. "Like, books, or journalism? I happen to be in publishing, so if that’s something you’d like to walk about we can…." He trailed off, his thumb continuing to rub soothing patterns on her thigh. "It’s not the easiest thing to break into but you’ve got a lot going for you. I’d be willing to help you if you feel ready.” . That was a genuine offer, regardless if he got laid… but he still felt that the way she was looking at him had an undertone

"You should come by my office sometime, if you want." He offered, his voice low. "I mean, if you're interested in publishing. We could... talk shop. Or something." He added, his hand slowly creeping higher up her thigh as he spoke.

“Or something?” She grinned widely. “Are you making a pass at me, handsome stranger Harry?” Her fingers stroked down his jaw towards his neck, messing with the collar of his shirt.

"I mean, m’being serious about helping you but… Maybe a bit of flirting is happening." He whispered, tilting his head to the side to give her better access. "I mean, you did ask where my ring was..." He pointed out softly, his hand now resting high up on her thigh, fingers spread wide, said ring gleaming in the low light. "And I haven't exactly been getting much action since the divorce..."

Eyes fell down to his hand and back up to his face, ever so slightly spreading her legs more to allow him to step closer between them. The heel of her shoe gently ran over his calf, biting lightly on her lower lip as she tried to keep the smile off her face. “And is that the only thing you want from me?”

Harry's breath hitched as she spread her legs, his heart racing at the subtle gesture. His hand tightened ever so slightly on her thigh, his fingers digging in just a bit as he leaned in closer. "No," He admitted quietly, his voice husky. "But it's a good start."

“Tell me.” She slipped her hand down to let them curl into the fabric of his shirt. “I’ve never been with an older man before, Harry. Are you all just as shitty as the younger ones? Or are you better?”

Harry's eyes darkened as she slipped her hand under his shirt, the rough pad of her fingers against his skin making him shiver. "I'm better." He said confidently, his voice deep and rumbling. "I know what I want, and I know how to treat a woman."

The man’s hand tightened on her flesh as she let out a breathy sigh, his eyes never leaving hers. "With respect," He said simply. "With kindness and attention. I open doors, I pull out chairs, I make sure they're comfortable and cared for. And in bed…" There was a pause, a slight smirk on his face as he averted his gaze for a single moment.

“In bed?” She echoed, looking up at him expectantly. “Don’t keep me on edge here. I’m dying to know.”

Harry smirked at her, his hand moving higher up her thigh, stopping right at the hem of her panties. His knuckles could feel how humid she was, no denying she was wet. It was hard to keep focused, but he had to. "Well, Y/N… I make sure they're satisfied," He said, his voice low and sultry. "I take my time, I pay attention to their body, I explore and learn what makes them tick."

“So you won’t just cum and roll over and fall asleep?” She hummed, her other hand running under his blazer and over his back. “Because I’m real tired of giving it my all and barely getting a subpar orgasm out of it. It’s why I was trying to be celibate for a while…”

Harry chuckled, shaking his head. "Not on my watch," He said, his thumb brushing against her panties. "I'll make sure you're thoroughly satisfied, multiple times if needed. I'll hold you close, kiss you, tell you how beautiful you are, while I make love to you."

“Ooo… he makes love..” She cooed, giggling lightly before leaning into whisper the next words to him. Was this an older man thing? Or a literature person sort of thing? Waxing poetically about the things he could provide, it all sounded amazing. But she had to know. “But can you fuck? Can you make me feel it for days, bruise my ass, get me so wet I ruin your sheets?”

Harry groaned quietly her words, his thumb pressing against her panties, feeling how soaked they were. "Fuck, yes." He growled under his breath, his other hand reaching up to cup her cheek. "I can be rough, I can be gentle, I can do whatever the hell you want. All y’have to do is ask."

Y/N let out a shuddering breath as his thumb brushed over her clit through her panties, looking to the side as she attempted to see if anyone was paying attention- but considering how crowded it was tonight, no one was paying them much mind. “So you’ll take me back to your place and make me cum? That’s what I want.”

Harry nodded, his thumb rubbing against her. "Yeah, sweetheart, I'll take you back to my place and make you cum so hard you'll see stars. And then I'll keep going, as long as you want, until you can't take it anymore."

“God.” The girl’s head rolled toward and thumped on his shoulder, feeling him chuckle as he rolled his thumb over her swollen clit. The lacy scrap of material she considered panties did little to hide how slick she was, the older man having plenty of fun playing with her as she turned her head and nipped her teeth into his throat.

Harry let out a low hiss at the sharp little bite, his hand still pressing against her clit through her panties. He reached into his pocket with his free hand and pulled out his phone, quickly typing out a text message before putting it back in his pocket.

“W-What are you doing?” She murmured, slowly pressing her lips to his skin and staining it with her lipstick. He was casual about playing with her, acting like stroking her clit was second nature as his other hand adjusted the straps of her dress back up from where they’d begun to droop.

Harry smirked as she inquired, his thumb still making small circles against her clit. He leaned in closer to her ear and whispered, "I'm sending a message to my housekeeper, to make sure the bed is prepared for when we get back to my place."

“God, M’gonna suck your dick so good.” She sighed, a tipsy giggle leaving her throat. “It’s big. I knew it was when I came over here but… shit, I’m gonna feel it for days.”

Harry grinned as she grumbled against his neck, his hand leaving her panties to grip her hip possessively. "You're going to love it, baby. I'm going to stretch your little mouth wide, and you're going to take every inch like a good girl." He crooned low in his throat. “But you need to get that pretty ass up and come t’the car with me. My driver is here.”

——-

Y/N let out a squeal of delight as Harry tossed her into his bed. His Californian King with a canopy, four postered, hand craved fucking bed frame, his shirt unbuttoned, belt undone and jacket on the floor. Her dress was over her hips and she wasn’t sure exactly how they’d gotten here, but what she was sure of was the fact that she really did like kissing him. “Kiss me.” She demanded, grabbing his scruffy face as he crawled up the bed and hovered over top of her.

Harry chuckled at her demanding tone, his mustache brushing against her lips as he obliged her request. He kissed her deeply, his hand wrapping around her jaw to pull her close. As they made out, he let go only momentarily to reach down and grab her dress, yanking it up over her head and tossing it carelessly aside.

That left her in just the pathetic excuse of lace panties, as she had forgone the bra for the sake of the dress, and there was no complaints on his end. Her hand pushed at the shoulder of his shirt, trying to get it off of him. “Want you closer.” She mumbled, leaning into him with a mewl as he pulled back to do as she asked. It was erotic and hot and she was surprised by the amount of tattoos he had, but god, did she want to see more of him.

Harry grinned, feeling her warm hands pushing at his shirt. He lifted his arms, allowing her to pull it off of him. His tattoos were extensive, covering most of his arms, chest, and back. Inquisitive hands ran over her sides, marveling at her form compared to his own build.

The man bent down and started to place kisses along her collarbone and up her neck. His rough hands squeezed her sides gently, thumbs brushing along her ribs. He continued to kiss and nibble at her neck, his facial hair tickling her sensitive skin. He whispered, "Wrap your legs around my waist, baby."

She did as asked, eyes fluttering shut as she could feel him through his trousers. Of course, she’d been right. The man’s cock was big like she had expected, and it was thick. Throbbing against her through the fabric, her mouth watered slightly as she rubbed herself against him, fingers finding his hair as he made his way down her throat. “Fuck, it’s been so long.” The slight scratching of the facial hair only made her feel more sensitive, like she was on a live wire. It was decided that she definitely liked it now.

Harry groaned at her words, the sound coming out more like a rumble from his chest. He continued to kiss and nip at her throat as she ground herself against him. His hands squeezed and gripped her ass, encouraging her movements. "God, you feel so damn good, and m’not even inside you yet."

Harry paused for a moment, looking up at her with a heated gaze. "You're so precious, so sweet... I've never been with anyone like you before." His voice was gruff, filled with desire. He ran his hands up her sides, marveling at her smooth skin. The curves, the indents, all of it was new and exciting.

“No?” She asked softly. “I’ve never been with an older man either. Kinda like it.” There was no hesitation in admitting it. “Was your ex wife not good to you, Harry?”

Harry's expression darkened briefly at the mention of his ex-wife. "She wasn't... attentive. And she certainly never looked at me the way you are now." He buried his face in her neck once more, kissing and nuzzling her skin.

“No?” It was astounding. “I don’t know how. If I had a man like you…” She let out a breathy laugh. “You’d have to pry me off of you. you are so attractive, so sweet… Can’t imagine why she wouldn’t be all over you, all the time.” It wasn’t something she could really understand. She barely knew the guy but she liked what she saw, and she liked it a lot.

Harry's heart swelled with pride at her words. He felt his ego growing a bit, having this beautiful young woman fawn over him. "I think she was always more interested in the status and prestige that came with being married to me, rather than actually being in love with me." It wasn’t something he liked to think about but in this instance he felt okay with it. If it hadn't ended, he wouldn’t end up here.

His lips continued to kiss and caress Y/N, his hands roaming over her curves almost in awe of what he had his hands on. It wasn’t what he had expected. People watching at the bar was his goal, really. He had one night stands a few times but he didn’t necessarily want this to be a one time sorta of thing. Not when she smelled this good and her lips tasted like cherry wine. He wanted to know what books she liked just as much as he wanted to know how she looked when she came. "But now I have you in my bed, and you're looking at me like I'm the most desirable man you've ever seen, so I think m’doing okay." He crooned, nipping at her neck.

“Because you are.” The girl purred. “All man and power in the best way. Not socially, but in what you are. You exude it.” Her cunt rubbed against him, making her eyes lull. “I knew you’d have a big dick. Knew it just walking up, how you stood. I wanted it inside of me.”

Harry let out a low chuckle, his voice a deep rumble. "Is that right? You wanted me inside you from the moment you saw me?" His hands gripped her backside firmly, spreading her cheeks as she ground against him. "Well, you're going to get it, baby."

“Mmm… I want it now.”

Y/N nearly whimpered as he pulled away but quickly shut up as she watched him stand up, hands working the button of his trousers. It took her seconds to lift up and get on her knees in front of him, shooing his hands away to take over. it had been months since she’d given head and while she wasn’t a normal lover of it, she had been dying to get her hands on him.

Harry watched with heavy-lidded eyes as she pushed his hands away and undid his pants herself. He bit his lower lip as she slowly revealed what she'd been craving. "You don't have to do that, baby." He said hoarsely, knowing full well that he wanted her to- but he wouldn’t make her. It would be more than okay if he focused on her. He got off on giving, and that’s what he focused on.

“Need to.” She gave him a look as she slowly tugged the zipper down, guiding his trousers down before palming him over his briefs. “Fuck, I’m gonna be full of this.”

Harry let out a low moan at her grip and the words that followed. The image of her full and well used was enough to send any red-blooded man to their knees, but he just stood there in front of her, letting her take control, letting her give him pleasure. He watched as she pulled his boxers down, freeing his length. His hands moved to cup the back of her head, fingers threading through her hair. He could see the lust in her gaze, and he couldn’t help but sigh again at the sight of her.

His thick, veined shaft jutted out proudly from a trimmed thatch of dark hair. The head was a dark, angry red and already glistening with precome. The older man let out a sharp breath as she wrapped her fingers around his shaft, slowly starting to stroke him. He watched intently as she gripped his cock, sliding it over the sensitive length, causing it to pulse in her grip.

A shiver of pleasure ran down her spine as she watched his control come undone. Her eyes were locked onto him, watching his cock pulse and throb in her hand. She could feel it grow harder with each stroke, leaning herself down and sticking out her tongue for a taste.

The sensation of her tapping tongue against the tip of his cock made him shudder, watching the precum string from his slit to the pad of her pink tongue. He looked down at her, seeing the hot promise in her eyes- this was going to be good and he knew it. She slowly began to slide the head of his cock back and forth between her lips, teasing it with her tongue.

Y/N wasn’t one to call any cock pretty, but she would dare to say it for him. Harry’s cock was appealing in the way most others hadn’t been. Maybe part of it was her overwhelming attraction to him in general, but she felt even more eager to make him feel good than she had with anyone else in the past. “I want to take it in my throat. I can do it, I promise. Jus’ need your help.” Her plea was finished with a kiss to the tip before opening her mouth, looking up at him to let him take over.

He guided her head forward gently, encouraging her to take more of him into her mouth. "Relax your jaw, baby, you can take it." He coaxed softly, his voice laced with desire. As Y/N did as he asked, Harry felt his cock slide deeper into her warm, wet mouth. Her lips stretched around his girth, pushing in slowly before he felt the tip of his cock hitting the back of her throat. He could feel her nose pressing against his pubic bone as she struggled to take him all in. “Shh, sweetheart. Just gotta get it wet for me, show me what you can do.”

He held her head steady, his hands gently gripping her hair as he started to slowly thrust his hips. The sound of his thick cock sliding in and out of her mouth filled the room, along with the occasional gagging noise as she struggled to accommodate his size.

"You're doing so well, baby," Harry praised, his voice low and gravelly. "Look at you, takin’ it like a good girl. You're gonna make me come so hard today, aren’t you, sweetheart? Just like that, that's it- relax that throat for me..."

As Harry continued to talk to her, his sweet words and praise, Y/N's eyes began to water from the effort of taking him so deep. She gagged a few times, her hands coming up to his thighs for support, but she refused to pull away for longer than a few seconds to catch her breath.

Her cheeks hollowed and her jaw ached, but she was determined to take him all in. Harry's hands moved to the back of her head, fingers tangling in her hair as he pulled her closer, fucking her mouth with more urgency. "That's it, baby. You're making me so hard... S’been so long... Been ages since anyone’s made me feel like this..." Harry's voice trailed off into a low moan as Y/N finally managed to take him all in, her nose pressing against his lower abdomen. “Tha’s it, right there- fucks sake.”

Harry's hips began to thrust involuntarily, fucking her mouth with shallow pumps as he held the back of her head, still buried deep in her throat. He released the grip, trying to urge her off- but she didn’t want to. "Fuck... you’ve got t’pull off, sweetheart..." he groaned, his breathing heavy and erratic. “Need t’fuck you.” Y/N whimpered around his thickness, her eyes watering as she shook her head slightly, indicating that she wasn't ready to give up yet. She wanted to taste him, to drink him down like he had with her. Harry's grip tightened in her hair, his voice strained.

"Babe...you've gotta-you've got to... please," Harry begged, his voice cracking as she continued to suck him off, her head bobbing and nose brushing his thatch of hair, making his eyes clench shut. "If you don't stop now, M’gonna, fuck...I'm gonna cum in your mouth..."

Y/N whimpered, her hands gripping his thighs tightly as she continued to suck him enthusiastically, eager to taste him. Harry's breathing became rapid and shallow, his fingers tightening in her hair as he struggled to hold back. "Y/N, last chance...I'm-"

The girl moaned as she felt him stiffen, his hips bucking forward as he finally gave in and let go, filling her mouth with his warm release. Watching his face fall in ecstasy, it was going to be worth the soreness tomorrow. She struggled to swallow it all, some of it dripping out of her mouth and down her chin. Harry's knuckles were white from gripping her hair so tightly, his body trembling as he came deep in her mouth. The sight of her swallowing him down was almost too much for him to handle, and he had to close his eyes and focus on not passing out. It truly had been a long fucking time.

As Harry finished cumming, Y/N eagerly cleaned his sensitive prick with her tongue, licking and sucking until he was completely clean. She ran her tongue along the veins and underneath the head, making him shudder and pull back. "Too sensitive...God, you're so good at that." he praised breathlessly. There was slight disbelief in there too, a slight tingling in his thighs as he looked at her as she pressed sloppy kisses to his hip bone. Mascara smeared under her eyes and lipstick a faded smeared mess, he wondered how he had gotten this lucky.

Harry needed a moment to catch his breath, his heart still racing from the intense orgasm. He looked down at Y/N, her messy appearance only making her more adorable to him. "You know what would be perfect right now?" he asked, his voice still shaking slightly.

“What?” Her voice croaked, feeling his thumb brushed away some of the tears on her cheek that had fallen from the gagging.

"Letting me get a taste of that pussy I've been fantasizing about." Harry suggested, his eyes still lingering on her messy and sated appearance as he pulled her up and pushed her to lay back down on the bed. “S’my turn now. Spread those perfect legs and let me see that cunt.”

Y/N obediently spread her legs wide, letting Harry see her dripping wet pussy. He let out a low groan at the sight as he got on his knees, his thumbs spreading her lips apart to reveal her slick folds. He buried his face between her thighs, inhaling her scent deeply before diving in and licking her from asshole to clit. There was no wasting any time or pretending to be shy about a single thing.

A started squeak left her mouth as her head popped up, hands gripping his head as he dove right in with little hesitation. Harry hadn’t seemed like the type to have any reservations in taking what he wanted, and it was being proven by how his tongue slid over her most sensitive parts.

He continued to eat her out with reckless abandon, his tongue fucking her pussy as if it belonged to him. Her breathing was heavy as he sucked on her clit, nibbling at it gently before returning to lap at her folds. His hands gripped her ass, spreading her cheeks wide to give himself better access to her tight hole. He wanted to have it all. “S’this okay, baby?”

“Uh-huh.” Y/N hadn’t really had anyone touch her there before but she couldn’t say she hadn’t been curious and self explored. It was always something she wanted to play around with and it felt exciting, handing herself over to the man like that.

Harry grinned mischievously against her wet flesh, his hands spreading her wider as he buried his face deeper. He pushed his thumb against her hole, slowly sliding it inside as he continued to lap at her cunt. “You taste so good, sweetheart...” he murmured, his voice muffled by her flesh.

He added a second finger to her ass, scissoring them apart slowly as he tongue fucked her pussy. Y/N's legs started to shake as the dual stimulation became too much. She gripped his hair tightly, her back arching off the bed as she let out a high pitched whine. "Ah!"

Y/N's fingers tightened painfully in Harry's hair, her knuckles turning pale as she tried to stay grounded while the pleasure consumed her. His tongue was spearing into her soaking wet hole over and over, curling up to rub against that spot inside her that made her see stars. And his fingers… god, those hands.

His fingers were stretching her asshole, pushing past the initial resistance and sinking deep into her tight heat. He scissored them further apart, popping her open wider as he fingered her ass. Y/N's legs shook violently, her whole body trembling as she felt herself on the verge of a massive orgasm.

"Harry...it's...too- please..." She babbled, unable to form a full sentence as he continued to stuff her holes. It had never been like this before, no one had even come close. He ignored her pleas, instead burying his face deeper and pumping his fingers faster. She felt so stuffed, so full, the pressure mounting inside her unbearably.

He felt her whole body stiffen, her pussy fluttering on his tongue as she cried out. She gushed against his mouth as she came, the feeling so intense and overwhelming that the waves of pleasure forced her to collapse against him.

Harry worked her through it as she trembled and whimpered with pleasure, his fingers still buried in her ass and his tongue still buried in her pussy. He felt a sense of pride and accomplishment, knowing that he'd reduced this beautiful young woman to a whimpering, shaking mess. It was not only an ego boost from what had been lacking for a while now, but he liked seeing how she reacted to him. He alone had done it.

Harry slowly lifted his head, wiping her from his face as he grinned wickedly at Y/N. "You taste even better when you're coming apart for me, sweetheart." He brought his fingers to his mouth, sucking them clean while maintaining eye contact with her. "And you’re tight everywhere, hm?”

Y/N stared at Harry, her eyes glazed over and pupils dilated from the intense high she was still riding down from. Her mouth was slightly parted, breath hitching as she watched him clean her off his hands. A soft blush spread across her cheeks, embarrassed yet turned on by his bold actions.

"H-Harry...that was...I've never...I mean...no one's ever..." She stammered, unable to form a coherent sentence even still.

He chuckled darkly, enjoying how flustered she was. "No one's ever played with your pretty little hole before?"

“No.” Her face felt hot as he grinned up at her. He seemed more than pleased and it made her feel good to know he was happy but still, she had the slight embarrassment that only came with the territory.

"Well, consider that box checked then." He said smugly, crawling back up her body to kiss her passionately. She could taste herself on his lips and tongue, the musky flavor a testament to what he'd just done to her.

He grabbed her wrists, pinning them above her head as he continued to ravage her mouth. She mewled into the kiss, arching up against him as she felt his hard length pressing into her stomach. "Does my pretty girl want more?"

“Mhm.” She nipped his lip. “Want you inside of me.” Was she still sensitive from her orgasm? yes. But she had been desperate to get him inside of her since she’d first spoken to him. “Do you- are you clean?”

He pulled back slightly, his breath hot against her cheek. "I'm always clean, sweetheart. I get checked regularly and I'm very particular about who I share my dick with." He gave her wrists a gentle squeeze before releasing them, reaching over to his pants to his back pocket to grab his wallet.

“I-“ Her hand reached for his wrist. “I don’t wanna use one.” The words laid in the humid air for a moment. It was risky, sure, as any sort of unprotected anything was, but she didn’t want anything in between them. “I want t’feel you inside of me…”

He groaned at her words, his eyes darkening with desire. "Christ, doll. You're gonna be the death of me." Leaning down to kiss her again, his tongue traced over her bottom lip before slipping inside her mouth. He took his time, savoring every inch of her. His lips found the sensitive spot behind her ear, causing her to shiver in anticipation. His hands made their way under her hair, feeling the warmth of her skin.

“Can I push in, baby?” He asked with a low tone, his lips tracing her collarbone. At her nod, he wasted little time. Poor thing hadn’t been fucked right before, and he would happily give her a proper experience. Reaching down between them, he positioned himself at her entrance. With one slow thrust, he entered her fully, feeling the warmth and tightness of her around him. His eyes rolled back in pleasure, as he buried the tip inside of her. “Fuck, thank you.”

He groaned as he pushed into her, feeling the way her body welcomed him. He paused for a moment, giving her time to adjust and letting himself feel the depth of her wet heat around him. His hands reached up to cup her breasts, his thumbs brushing over her nipples.

Being with a younger woman was different for him, but maybe it was just her- he realized as he moved inside of her. It was like being with a whole new sense of being, one who was full of energy and life. Everything about her was so fresh and vibrant, from her tight little pussy to her perfect tits and gorgeous face.

He continued to thrust into her, feeling the way her walls tightened around him. His hands moved down from her breasts, over her soft stomach and to her hips, exploring whenever he could.

His movements were slower, each thrust deliberate and measured. He wanted to savor the feel of her, the way her body yielded to his. He was drawn to watch her face, loving the way her eyes fluttered shut and her mouth fell open as he filled her. "Look at me," he murmured. She opened her eyes, looking at him with a dazed expression. "Good girl, like t’see those pretty eyes." The man sighed, unable to resist praising her. He continued to thrust into her slowly, each movement filled with lust and desire.

“Fuck.” She kept her eyes on him as her hands ran over his hot shoulderbaldes, keeping that contact as he dipped all the way back home as deep as he could. Her mouth fell open and a high pitched noise left her throat without her permission, brows furrowed. “It’s never been that d-deep.”

He grinned at her, loving the way her inexperience made her react to him. "That's because no one's ever taken the time to stretch you out right." He leaned down to kiss her neck, his hips continuing to move in slow, deep thrusts.

“Where the fuck have you been, then?” She laughed breathlessly, letting her eyes fall back closed as he kept the thrusts slow and deep, relishing every inch he took. her body was lax and hot, his for the taking. Right now she felt like he could do anything and she would welcome it. “Are all older guys like this, or is it j-just you?”

He chuckled darkly against her neck, "There's a reason why women often prefer older men, doll- but M’gonna say for greeds sake, s’just me." He suckled at her skin, his hands sliding down to grip her thighs and push them back farther, opening her up even more to his slow, deep thrusts.

“Oh, shit.” Her mouth fell open and he welcomed it, sliding his tongue back inside her mouth and humming at the taste of her against him. The fact there was not a single barrier, albeit risky for the first time fucking, made it even hotter.

His movements became gentler, his hands caressing her skin instead of gripping it. "You like that?" he murmured against her lips, his hips rolling into hers instead of thrusting. "You like knowing that there's nothing between us?" He pulled back slightly, looking down at her with a heated gaze. "I want you to look at me when I ask you something," he said, his voice low and commanding as he took her eyes. "Are you on any birth control?"

“Y-Yeah. Uh-huh.” Her eyes wide, she looked up at him hazily as she wrapped her legs further around his hips. “Don’t pull out when you cum. Please- I know m’crazy, but I need… need it.” Y/N knew she was insane for it, but their connection was so strong, every thrust inside of her, hitting places she didn’t know existed prior to this… she needed it.

His expression softened, a coo leaving his mouth as he nodded at her. How precious. "Alright, sweetheart. I promise I won't pull out." A dumb decision on his part too considering they’d just met but in the midst of it all, it was all he wanted to do. His hips began to move again, his pace quickening as he felt the heat of her around him. "You're going to take it all then, aren't you?"

“Yeah.” She mewled. From the sounds and feel alone she knew she was making a mess on his cock, but she had a feeling he was enjoying it every time he snuck a glance between them. “Take everything you give me, Daddy.” It was a risk, but she wanted to see what he’d do.

His face contorted with pleasure, his brow furrowing and his jaw clenching. "Good girl…" he hissed, his voice low and gravelly. He buried his face in her neck and thrust into her with more need, his movements becoming more urgent. "You're going to make me cum, doll."

“Cum.” She begged. “Cum in me. Then fuck it into me. Please.” Her nails dragged over his toned back as she clung to him, his bed creaking as he fucked into her welcoming, wet pussy.

He let out a primal grunt and slammed into her one last time, his cock pulsing as he filled her with his hot, thick cum. He held himself inside her, his hips jerking as he pumped his load deep into her cunt. "Fuck, baby... I'm going to fucking fill you up."

But he wasn’t done. Not in the slightest.

With his cum still pouring into her, he reached under her and grabbed her thighs, spreading them wide apart. Observing the mess he made, he fixed his fingers on her clit as he fucked the cum into her just like she asked. “I gave you what you wanted, darling. Give me what I need too, mm?” His lips brushed her cheek, feeling the beginnings of her orgasm. She just needed a little extra, and he was more than happy to provide.

Y/N squirmed slightly as she felt it creep up on her faster than she could anticipate. The pulse of his cock as it dribbled the last of his cum inside of her, the feel of his facial hair brushing her tender skin and his fingertips rubbing quick circles over her clit, it was impossible to keep from holding back. Heat boiled in her stomach as she tried to tell him, but it came on quicker than she could speak.

A broken moan left her lips as her body shook under him, eyes burning with tears of pleasure as he fucked her messy cunt and continued the circles until she pushed his hand away, grabbing his face and kissing him far more messily than she would have done in any other capacity- but this felt right. Fucked out and wobbly, melting into the bed as he slowly stopped the thrusts and stayed buried in her.

“Mm- baby. Sweetheart…” he pulled back to look at her. “You alright? Tell me how you’re feelin’.” He needed to check in on her, make sure she was feeling properly taken care of. Just by the look of it alone he had a feeling she felt that way, but he wanted to hear it from her pretty lips.

“I’m so good.” She grinned, drunk with the pleasure as she looked up at the handsome man. He was everything that she had dreamt about when she woke up sticky between her thighs. Aged like a fine wine.

“Can we go again?”

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