#his confused eyes really got me | Explore Tumblr Posts and Blogs

rowarn · 3 months

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IF YOU NEEDED ME !

simon riley/reader – 7.1k words sale of a lifetime mini series !

tags: smut, childhood best friend!simon, virginity for sale trope, unrealized feelings, soft!simon, protective!simon, virgin!reader, afab!reader, no prns for reader

cw: loss of virginity, cunnilingus, wet & messy, fingering, creampie, mid-sex love confession, a little arguing but nothing crazy tbh, petnames (love, lovie, sweetheart)

; he remembers the way you would look at him when you were children, all smiles and bright eyes. he never thought he was deserving of such happiness. but now, with you shyly covering your bare breasts, in his bed, he feels like he’s the only man deserving of you.

or.

he may not have been the first man you picked to give your first time to. but looking back, you realized he was the only right choice in the end.

Meeting some unknown, shady guy out on the street outside of a seedy bar wasn’t the smartest decision you’ve ever made. Nor was it how you actually intended to spend your Friday evening. But it was the only option you had at the moment, so you swallowed your nerves and forced yourself to stay put at the spot the guy had chosen despite the fact that being out on the street made you feel x10 more nervous and vulnerable.

You could hear the loud music and chatter inside the bar every time the door opened to let someone in or out. There was a chill in the air that had you contemplating actually going inside and just telling the guy to meet you in there – you were about to give the bastard your damn virginity, the least he could be was accommodating to your temperature struggles. Plus, you could really use a drink.

A car, expensive by the looks of it, pulling up to the curb had you pausing in that train of thought. You recognized him from his profile picture when he stepped out of the vehicle – Lucas, you recall being his name. Whether that was really his name or not didn’t matter; all that mattered was he brought what he promised.

“You have the money?” you asked when he approached you, giving him a tight-lipped smile as a greeting.

“Yeah, got it in the car. All cash, I hope that’s alright,” he grinned, a sight that made a shiver go down your spine. His tone didn’t match the smile, all transactional and dull despite the glimmer in his eyes.

He wasn’t necessarily unattractive but he certainly wasn’t your type. There was a look in his eyes, one that made your skin crawl because you felt like you were nothing but a piece of raw meat in front of a starving, salivating predator.

“We should get going,” he said, hurrying to open the backseat of his car for you.

You paused, “Aren’t we going to go inside or something?”

He looked confused, grip on the door tightening for a moment before he bursted out laughing. When he saw the shocked look on your face he sobered up, “Sorry, sorry, that was rude of me. Sweetheart, this isn’t a date. I’m just here to get what I paid for.”

“Oh…” you swallowed around the lump in your throat at the condescending tone, humiliation making your cheeks burn, “Right.”

Tears stung the back of your eyes and you quickly averted your gaze so he wouldn’t see how much that stung. Of course, you knew it wasn’t a date. This was a transaction. But you at least thought you’d get to know the guy who was about to take your virginity. You should have known better.

A man who was paying for your virginity wasn’t bound to be someone you could trust to feel comfortable around. You quietly sigh, resigning yourself to this all for the sake of some fucking money.

You settle into the car, heart jumping into your throat when the door slams. It feels as if you’ve just sealed your fate and you can’t deny that you’re scared.

But there’s an envelope next to you that you can see stuffed with bills and you clench your fists, trying to calm your racing heart by closing your eyes and breathing.

You just hope this decision doesn’t cost you your life or something. You’d hate to imagine what that would do to a certain someone.

Suddenly, the car jostles. Your eyes snap open and you see Lucas is jacked up against the side of the car, a very familiar form caging him in. His scarred hands grip the man’s shirt in tight fists. You can’t hear what they’re saying but you can see Lucas is chattering frantically, gesturing wildly with his hands in an attempt to quell the angry man in the skull balaclava.

You curse to yourself, a different kind of terror shocking through your system. Lucas is thrown to the side and you wince at how hard he hits the pavement before the car door is jerked open.

You can’t even say anything before a strong, rough hand wraps around your arm, yanking you out. You stumble once you’re on your feet, falling right into his chest.

You try to pull away but his arm clamps down around you.

Lucas is cursing and screaming his head off, words you don’t even bother to try and decipher because you’re too preoccupied with the masked figure that made his sudden appearance. Nerves make your knees shake and from the look of pure rage in his eyes, you know you’re in deep shit.

Lucas opens the car door and slams it before driving off, tires squealing against the pavement before he vanishes. Along with that wad of cash that was going to be yours in just a short time.

Suddenly you’re angry, shoving your hands against his chest to get him away from you.

“What the hell do you think you’re doing, Riley?!” you shriek, shooting him the fiercest glare you could muster.

“I should be askin’ you that,” he sneers, “The hell were you doin’ with that prick?”

“I–”

“Don’t answer that,” he snaps, cutting you off swiftly, “I know what you were doin’. If you needed money that badly you should have told me.”

“It’s not your concern, Simon!” you cry, resisting the urge to petulantly stomp your foot.

You’re so pissed.

Simon Riley and you went way back, childhood friends. The two of you had always been in each other's lives. Simon especially was always there when you needed him, a beacon of safety and protection. Your best friend and someone you loved to the ends of the Earth.

But right now, you’re so angry with him that you can’t seem to think straight.

How dare he show up now, when you’re about to do the most humiliating act of your entire life. How could he show his stupid, masked face here when you didn’t even ask for his help in the first place for a reason.

“You are always my concern,” he shoots back, scarred knuckles turning white from how hard he clenches his fists, “I have always taken care of you. You should have come to me for help instead of puttin’ yourself in danger like this. You didn’t know that guy, what the fuck were you thinking?”

Anger makes your skin hot, sweat beading on your forehead, blocking out the chill that once made goosebumps rise. You feel ashamed that you were caught in this situation – that the man you’ve known your entire life knew you were about to sleep with some random asshole for a fat wad of cash. You don’t like that he’s made you feel ashamed and confronted you with it.

“Just fuck off, Simon!” you shriek, the only thing you can think of before turning on your heel and stalking away from him.

You don’t glance over your shoulder to check if he’s following because you know he most likely is – from a safe distance to make sure you make it inside your apartment alright but far enough that you can’t get mad at him for it. Your jaw is clenched so tightly that you feel a headache radiating down your neck.

By the time you reach your apartment, the anger has simmered and all you’re left with is a festering shame that makes tears fill your eyes. You wrap your arms around yourself and quickly shuffle yourself inside, not bothering to check if Simon is out there or not. All you want is to get a hot shower and crawl into bed for the rest of the weekend.

You do just that, letting the burning hot water scald your skin until you can’t feel any emotions except exhaustion. And then, you crawl into bed and let sleep overtake you without a second thought.

When you wake up, it’s clear that it’s late into the afternoon. The sun is high in the sky and shining painfully bright through the crack in your curtains. You groan and roll over, slapping the bed to find your phone.

You grab the device and unlock it, taking a moment to scroll through your notifications. There’s some angry messages from the guy from last night – cursing you out for setting him up to be jumped. It makes you roll your eyes before a particular notification catches your eye.

It’s from your bank – alerting you of a deposit.

You sit up straight in your bed, brows furrowed before your eyes nearly bug out of your head when you see your bank statement. It’s more than you needed and you know exactly who was responsible.

You jump out of bed, not even bothering to dress out of your pajamas before you’re shoving some slides onto your feet and storming out of your apartment.

You’re so heated that you can’t even remember the walk to Simon’s place, your mind racing a million miles a second. You storm up to the door and slam your fist on it, the hard wood making your hand sting from how hard you pound.

The radiating tingle of pain is quickly forgotten when the door swings open.

Simon stands there, looking down at you expectantly. He leans against the door with his arms crossed over his chest. He wears an army-issued t-shirt that’s a bit too tight. The sleeves stretch taunt around his biceps and you can make out the swell of his pecs. It’s not very often that you get to see his tattooed arms, littered with scars since he tends to wear long sleeves most of the time.

He doesn’t look at all surprised to see you, clearly having expected you. The apathetic look in his eyes just solidifies that you were right all along.

“What the hell is your problem?!” you cry without so much as a greeting.

He sighs, broad shoulders rising and falling with it before he opens the door wide and motions you inside. You duck underneath his outstretched arm, turning to watch as he closes the door and locks it.

He wanders into the kitchen and you realize you can smell bacon. He doesn’t seem at all surprised by your outburst nor does he seem interested in acknowledging your question.

“Are you hungry?” he asks, only solidifying how unperturbed he is by your display of anger.

“No!” you snap, “I want to know why you did that, Simon!”

He sighs again, much louder but doesn’t respond. You stand in the doorway to his kitchen, watching him plate his lunch – which is actually just breakfast food. He places the dish on the table and pauses, looking up at you.

“You needed the money, I had it,” he offered with a shrug of his shoulders.

“I was handling it on my own,” you say, “I-It was my problem to solve.”

“By sellin’ yourself to some prick?” he snarls, the anger he was masking coming out in a flurry.

“I wasn’t selling myself–” you refute but he slams his palms down on the table. His cutlery clatters with the action and you jump.

“I read that post you made,” he hisses, teeth bared, “There’s no fuckin’ reason you should be selling your virginity for some cash when I was right here the whole time!”

Your cheeks burn when he brings up your virginity, crossing your arms over your chest protectively, “I-It’s mine to sell if I want to! I needed that money!”

“And now you have it,” he says with finality.

He takes a seat and you stand there, fuming. Your jaw is clenched, teeth grinding together as your mind races to find a rebuttal. He begins to eat, taking large, fast bites that just shows how he’s been conditioned to eat quickly by the military.

“That’s not the point, Simon,” you huff, growing less angry and more frustrated by this conversation. You were just going around in circles.

“Then what is the point?” he snaps, snatching his empty plate and angrily tossing it in the sink. He turns to you again, a frown evident on his face, “You got the money you needed safely. That’s all that matters.”

“It’s too much money, Simon!” you cry, “I was selling something in exchange for it!”

“I care about you,” he says, “That doesn’t matter to me. What’s mine is yours, you know that.”

You silently glare at him, wishing that the heated stare would get through to him. He stands unbothered, staring blankly at you with his fists clenched by his sides.

You hang your head, sighing, “I-I can’t take your money, Simon, alright? I’m already in debt and I’m not going to be in debt to you of all people.”

“You feel like you owe me, is that it?” he asks.

You nod your head, heart rate spiking when he stalks towards you. You’re close enough to smell his body wash and aftershave, a painfully familiar scent that you adore. He stares down his nose at you, brown eyes lidded and lazy.

He reaches out suddenly, rough hand gripping your cheeks, smushing them together until your lips pucker, “Then give me a kiss as payment.”

“H-Huh?” you whimper dumbly, eyes wide in shock as his face grows closer and closer.

“It can be payment for a kiss, lovie,” he coos, syrupy sweet and soft, “Will that make up for it, then?”

The air in your lungs suddenly doesn’t feel like enough. This is a man that you’ve known almost your entire life so you’ve obviously thought about him in a romantic sense at some point. Hell, when you were a teenager you even had a crush on him. But he never once looked at you any other way than as a friend so you quickly got over it – or maybe that’s just what you told yourself. Because as you stand there, staring into his eyes, you realize that kissing him would feel like a dream come true.

You find yourself nodding despite the inner turmoil going on in your head. Simon huffs through his nose before leaning down and pressing his lips against yours.

There’s a shock of electricity that goes through you at the contact. Your eyes flutter shut as you lean into the kiss, letting him take over. He works his lips expertly against yours, eventually abandoning his hold on your face in favor of wrapping his arm around your waist. You gasp into the kiss when he suddenly yanks you closer, your body pressed close against his.

He’s warm and sturdy against you, a solid form of muscle that makes you feel safe and content – just as he always has. His hands are big and rough as they grip your hips, kneading the soft flesh there as he gets lost in kissing you.

“S-Si,” you find yourself muttering without realizing.

He hums in response, chuckling when you continue to mindlessly kiss him. He pulls back, one hand coming up to wrap lightly around your throat, thumbing at your jaw as your eyes slowly focus on him, “What is it, sweetheart? What do you need?”

“I-I don’t…” you swallow thickly around the forming lump in your throat, “I don’t know. I just…”

“Show me,” he breathes, softer than you’ve ever heard his voice.

The sweet, tender look in his big, brown eyes is what gives you the courage to grab his wrist, leading it just under the hem of your shirt so he can touch your bare stomach. You give him a shy glance from under your lashes, hoping he’ll get the hint that you want more.

You want him.

Simon, in all his experienced wisdom, understands immediately what it is you’re aching for. His hand travels up further, pausing at your ribs, just under the swell of your breast. Your heart hammers in your chest when your gaze meets his. His eyes are lidded, long lashes obscuring his pupils but still burning into you.

He stares deep into your eyes, waiting for any sign of hesitation as his fingers creep higher and higher. You suck in a breath when he cups your breast in his palm, squeezing lightly to feel their weight.

A large, calloused thumb creeps up, passing ever so softly over your nipple until the bud peaks and hardens under the attention. You sigh at the feeling, new shocks washing over you that you’ve never experienced before.

Sure, you played with yourself plenty – you had a healthy masturbation life, you’d say. But you’d always just been focused on reaching an orgasm, never on the build up. You imagine, however, it would never feel as good by yourself as it does with him.

He pinches your nipple between two fingers and you whine, lips parting as the sound escapes. Simon takes the opportunity to slide his tongue into your mouth. Your hands grab his shoulders, desperately clinging to his shirt as you lose yourself in the sloppy kiss.

Drool drips down your chin – it's messy and hot between the two of you. His hand switches to your other breast to give it the same attention as the other. You tremble in his arms, overcome by the insatiable throbbing between your thighs.

You shift on your feet, the fabric of your panties stick uncomfortably to your core. You’re so wet, wetter than you’ve ever been in your life. By the time he pulls back, there’s a string of saliva connecting your lips to his.

“You want more?” he asks, voice gravelly as he speaks, as if he’s drunk. You nod your head and he clicks his tongue, “You gotta tell me, sweetheart.”

“I-I want more, Si,” you whisper, feeling your cheeks burn as you admit it.

“Let’s go,” he hums, taking your hand in his as he leads you around the couch towards the hallway.

“Where?” you ask dumbly, hoping that making some kind of conversation would ease the nerves steadily building in your chest.

“The bedroom,” he responds, stroking his thumb over the top of your hand as if he can sense that you’re nervous, “Wouldn’t want to be stripped down in the middle of the living room, I imagine.”

“N-No,” you squeak, cheeks burning even hotter at those words.

You’re going to be naked. In front of another person for the first time. In front of him. Simon.

“There now, lovie,” he whispers as he shuts his bedroom door behind the both of you. He takes your waist in his hands, kneading the soft flesh there, “It’s alright.”

“I-I’m just–”

“Nervous,” he finishes for you, smiling softly when you nod, “I know. We can stop anytime you’d like.”

“I don’t want to,” you rush out, hands coming up to press against his firm chest, “Just…d-don’t be upset when I don’t know what I’m doing.”

The tender way he looks at you sets your heart pounding like a little rabbit. A ghost a smile appears on his lips, “I would never do somethin’ like that.”

“I-I know, I just…” you look down at your feet only for him to catch your chin in his fingers, pulling you to look up at him.

You swallow thickly around the lump in your throat, holding your breath as he descends down. His lips find yours all over again, as exhilarating and mind-melting as the first time.

Just the sweet, deep kiss he gives you has your nerves dissipating a bit – back to normal levels. You no longer feel the desire to flee, you just feel an intense longing and anticipation. You crave more from him.

As if sensing this, his fingers find the hem of your shirt. He slowly starts to pull it up, agonizingly slow. But you’re grateful for it, it gives you time to prepare before you’re bared completely to him. You lift your arms for him, a sign that you’re still okay with this.

He pulls it up over your head and lets the fabric drop to the floor. But he doesn’t look down, he continues looking in your eyes, softly pecking your lips as his hands cup your breasts once more.

When you sigh and lean into his touch, he finally lets himself break the eye contact. He sucks in a sharp breath when he sees how pretty your tits sit in his hands. He touches them softly, sweetly brushing over your nipples in admiration.

“Perfect tits, lovie,” he coos, chuckling when you whine in embarrassment.

His head descends, pink lips parting to take one of your nipples in his mouth. It’s hot but his tongue is soft when it circles and flicks at the bud. He sucks, popping off lewdly before switching to the other one.

The sensation makes you squeeze your thighs together, imaging what that would feel like around your clit. Your hole clenches around nothing, drooling messily into your panties. The fabric was so wet by now that it couldn’t soak it up anymore, leaving it to slick up your thighs instead.

Your core ached, a feeling only Simon would be able to soothe.

“Please, Si,” you finally break, whimpering pathetically.

He detaches from your breast, lips wet and swollen from the worship he had been giving your now sore nipples. His pupils were blown wide, black swallowing brown and you were sure that yours looked the same.

He stands to his full height, nudging you backwards until your knees hit the bed. They buckled at that, leaving you to fall back against the bed. Simon’s bedding was soft, the scent of detergent and his own body wash filling your senses. You relax at the familiar, comforting scent, sinking into the blankets with a bashful smile on your face.

To Simon, you’re an ethereal beauty. You take the air right out of his lungs with the way you look at him.

He remembers the way you would look at him when you were children, all smiles and bright eyes. He never thought he was deserving of such happiness. But now, with you shyly covering your bare breasts, in his bed, he feels like he’s the only man deserving of you.

He scooches you up the bed, crawling on after you until he’s on top of you. Though you’re still wearing your pants, you feel so vulnerable beneath his weight. He’s heavy and warm and he smells so good. You can’t focus on anything except for him – he’s all around you and it’s exhilarating.

Feeling bold, you reach up and tug at his shirt. He pulls it off with ease, revealing his toned, scarred upper body. You can’t help but trace over some of the ones you’re familiar with – there’s one from a time he fell out of a tree trying to rescue a cat that you had been crying about. He fell out of the tree on the way down, a jagged branch stabbing into his upper arm and slicing it open. There was another one from when you were teenagers, some other kids jumped him and he took a stab to his shoulder trying to protect you. You kiss that one and he softens, as if he’s remembering it too.

He’s always been there for you, an overwhelming presence that you simply couldn’t live without. The fact you’re here, in this bed, about to give him your virginity is something that you never would have expected.

And to think, you were planning to sell it off to some random loser.

“I’m glad you stopped me,” you find yourself whispering.

He looks confused for a second before he hums, nodding in understanding, “I am too.”

“I-I want it to be you, Si,” you whisper, the confession leaving you embarrassed. It’s true, all this time, you realize, he’s all you’ve ever really wanted. You had just buried it deep down so you no longer felt those sparks towards him.

“I’ll take care of you,” he whispers back, as if the two of you are sharing some secret little moment that no one else can hear about even though it’s just the two of you in this room.

“You always do,” you respond, the words making his dark eyes light up.

He kisses you deeply, moving his lips slowly against yours. When your hands come up to grip the back of his neck, he takes that as his cue to move down to your neck, then your collarbones, down the center of your chest between your breasts, the spot between your breasts, and finally your navel.

You lay back, head in his pillows with your hands on either side of your head. You watch him, breathing labored as you wait for his next move. He pauses in his path, looking up through his lashes at you before his fingers find the hem of your sweats. You swallow thickly, holding your breath when he slowly begins to pull the fabric down. You lift your hips to help him, pulling your legs free while being careful not to kick him by accident.

He keeps his gaze on you until you’re settled back down into the bed and the pants are forgotten on the floor to be collected later. Then, he looks down.

Even though you still have your panties on, you know that the white cotton is soaked through and hides absolutely nothing from his view.

You watch as he licks his lips, as if his mouth is suddenly bone dry. His hands are burning hot when he touches you again, sliding over your thighs to your hips. He leans down, pressing his lips against each of your thighs.

His thumb reaches down, stretches over your pubic bone to touch the sticky fabric. You nearly jump at the sensation – someone’s fingers other than your own touching you there for the first time. Simon’s fingers.

As if he can’t help himself anymore, he tugs the waistband of your panties and yanks them down your thighs. You squeal when you’re jostled under the force.

He holds the material up and you’re mortified to see just how wet they are. He runs his thumbs over the crotch and you whine, drawing his attention from them. He drops them to the floor and returns his hands back to you, gripping underneath your knees, so he can spread you all the way open.

Your hands fly to your face, covering your eyes in embarrassment at how exposed you are. He doesn’t seem to mind, pressing a kiss over the top of your hands before moving back down your body.

You peek through your fingers only to find him already staring at you with a sparkle in his eyes. He carefully spreads your slippery folds apart with his thumbs, the movement causing a wet, sticky sound to emanate from between your legs. The little bud of your clit is hard and twitching as it’s exposed to the cool air of the bedroom. When he’s sure you’re looking he leans down, pink tongue hanging out of his mouth. You stop breathing as you watch a fat glob of spit roll down the surface of the smooth muscle and splatter right on your clit.

“Si-!” your squeal of his name is cut off when your eyes roll back in his head as that sinful tongue slides right over your bud.

Your whole body twitches at that, hands falling away from your face so you can reach down and grab his hair. It doesn’t even seem like he notices your grip, focused on slurping up that sensitive nub into his hot mouth.

You choke out a moan, tilting your head back into the pillows as your back arches. It feels just as good as you thought it would when he was giving the same, lewd treatment to your nipples.

He continues to suck and lick your clit until your mind is completely blank and all you can think is him. Then, all at once it stops and he pulls back, letting your bud slip from the heavenly clutch of his lips.

“You ever have somethin’ inside you, lovie?” he asks, bringing up one of his fingers to swipe through the folds of your entrance, as if to show you what he intends.

You swallow to moisten your throat before nodding, “J-Just my fingers.”

“How many?” he asks, growing more confident in prodding at the tight little hole.

“T-Two,” you breathe, any embarrassment you felt long dissipated in the face of true pleasure.

“Alright, lovie,” he hums, “Just lay back, I’ll take good care of you, yeah?”

You nod and do as he says, turning utterly boneless against the blankets. The sweat already slicking your skin despite the fact you’ve only just begun makes the fabric stick to you.

He prods at your entrance for only a second longer before finally, he pushes his thick middle digit inside you. Your cunt is so wet and pliant that it hungrily swallows it up to the very last knuckle. You clench around it intentionally, getting used to the feeling of the foreign finger inside of you for the first time.

It feels so different compared to your own, thicker and rougher. The sensation is so strange but you can’t say you don’t like it – in fact, it feels amazing. You already want another, feeling like one just isn’t enough to give you that unknown feeling you’re chasing. It’s like you have an itch that needs to be scratched and only Simon can do it for you.

As if sensing this, ever the reliable one, he carefully introduces a second finger. The stretch is unfamiliar, a burn around your entrance following as he reaches the last knuckle on that one too. His middle and ring finger stuffed snuggly inside your gooey little cunt as you whine and squirm from the feeling.

Once you’ve adjusted, he slowly begins working them in and out of you. You slick up his fingers easily, streaks of creamy white coating his skin and making his mouth water. When he crooks his fingers up suddenly, prodding at that tender little spot inside of you, your entire body twitches and the most beautiful moan rips from your chest.

He can’t resist leaning down and trapping your pulsing little clit under the flat of his tongue. He doesn’t slurp it into his mouth like before, instead, he just licks over it, pressing it down with the muscle. Your eyes are rolled up and your mouth hangs open as you moan and moan, tugging mindlessly at his hair as he works you towards your orgasm.

It grows and grows, the unrelenting pleasure of his fingers fucking deeply into you and his tongue lapping sloppily at your clit like a mutt driving that knot in your belly to tighten. Drool spills out around his tongue, slipping down to meet his fingers where he easily fucks it into you – the added lubrication not needed but so very welcome with how much wetter and messier it makes you.

“S-Simon…” you pant, gasping to catch your breath as the pleasure makes it hard for you to even think.

He glances up at you through his lashes but doesn’t offer any other acknowledgement. There’s a knowing look in his eyes that tells you he knows exactly what he’s doing. He’s going to wring this orgasm out of your little cunt whether you like it or not.

And fuck, do you love it.

The orgasms you brought yourself in the deep of the night, little hands stuffed down your panties as you played with your clit and stuffed yourself with your own fingers was nothing like what you were experiencing now. Simon’s thick fingers and hot tongue were torturing your little clit until your entire body started to lock up.

You looked at him desperately, unsure what was even going through your mind besides him and how fucking good you felt right now.

Just as you teetered on the edge of this orgasm, he suddenly changed up and swallowed your twitchy little clit into his mouth. He sucked, sending you flying over the edge with a shrill wail of his name. Your legs kicked and twitched, heels hitting him on the back as you trembled and shook through the orgasm that he eagerly fucked out of you onto his fingers.

He suckled your clit, swirling his tongue around it until it was too sensitive and you were tearily pushing him away. When he finally released you, slipping his fingers from your cunt, you were boneless and twitching on the bed. You didn’t even try to close your legs when he pulled away, giving him the perfect view to watch your cute little pussy clench and messily drool cum in the aftermath of your orgasm.

He popped his fingers in his mouth, eyes rolling and lashes fluttering at the taste of your cum tingling on his taste buds. As you came down, eyes closed and breathing heavy, he began pulling at his belt.

You could hear the metal clinking as he dropped it to the floor, peeking your heavy lids open to see him pull the button of his jeans open. As he slowly pulled them down, his underwear went with and suddenly you were more aware than ever.

His cock was something to behold. Thick and veiny, bobbing in the air where it hung – too heavy to actually stand upright. You’d seen dicks in porn before but none of them prepared you for Simon’s. Precum dribbled from the tip, creating a long, gooey string down towards the floor before it broke.

He wrapped a big hand around himself, giving a few good strokes as he reached down to cup his own heavy balls. The hair wasn’t wild or offensive, but neatly trimmed short.

“All good, lovie?” he asked, stepping out of the pool of his jeans and boxers so he could kneel on the bed again.

“All god-good!” you blushed as he laughed, leaning down over you to balance his weight on his elbows.

“You still want this?” he asks, hushed and sweet,

You glance between your bodies to see that intimidating cock, drooling messily over your skin. You realize, quickly, that you’ve never wanted anything more in your life.

When you voice such, he looks relieved, like a weight was lifted off of his shoulders. He sits back on his heels and spreads your legs, pushing your knees up to your chest.

“Hold them there,” he orders, which you follow immediately.

Your elbows circle around your knees, holding yourself open for him as he asked. He whistles low in appreciation when your cum-slicked cunt was spread and exposed for him to prod his cockhead against.

He swipes the tip up and down through your folds, humming appreciatively when your little hole tries to suck him in every time he grazes past it. He nudges your clit, the little bud still hard and sensitive from your orgasm but so eager for more. He couldn’t wait to grant your wish and make you cream on his cock.

You watch him with wide eyes as he starts to push into you. Your jaw drops as you feel that burning stretch, an ache settling between your legs as he continues to sink himself into you.

“F-Fuck, wait, Simon!” you squeal and he halts immediately.

He’s only reached just past the head of his cock but he reaches down to pet your clit. The pleasure shoots through you, making your toes curl and your walls relax around him. He keeps his eyes on your face for any sign that you want him to stop as he moves his hips again.

More and more of his cock sinks inside and his thumb keeps working little circles over your clit until his hips are flush with yours. Your voice breaks as you moan when you realize you’ve taken every single inch of him.

He’s heavy and throbbing inside of you and you clench around him intentionally, forcing a moan from his chest.

He leans down, arranging your knees over his shoulders, folding you up and pressing down on you. He’s heavy and it makes it hard to breathe but that makes it even better – the pleasure of being speared on that fat cock and being utterly helpless underneath this man is better than any fantasy you could have made for yourself.

“Fuck,” he snarls, rolling his hips back before rocking them forward again, heavy balls slapping against you as he does, “Can’t believe you were gonna give this little cunt away to some prick.”

“S-Si,” you whimper, biting your lip at the feeling of him slowly and carefully rocking his hips against yours, “‘M sorry, sh-shoulda been you all this time.”

“That’s fuckin’ right,” he hums, “No one else gets to love you but me, sweetheart.”

“O-Only you!” you agree, nails digging into his shoulders when he hits that spot just right.

He can feel you soaking his cock, drippy cum lathering him up to make every glide of his cock wetter than the last. He sits back up on his knees, adjusting his grip so he can pin your legs wide open, giving him the best view of your greedy cunt swallowing his length up.

He begins to fuck you in earnest, pulling out halfway before sliding home again - nothing like the little movements he gave you to prepare you. He was going to show you exactly why you should only think of giving him this precious pussy for the rest of your life. No one will ever be able to fuck you as good as he can, he’s going to learn your body like the back of your hand and you’re never going to be able to cum as hard as you can with him. You’ll never even want to use your own fingers again when he’s done with you.

You can’t do anything but lay there and take it, take the pleasure and take his cock. He hits so deep, prodding at your cervix in a way that aches but it only feels that much better when it’s mixed with mind-numbing pleasure.

Simon looms above you, panting and groaning as he fucks you like he was made to. He angles his hips just right, blunt nails biting into your thighs where he pins you open, neither of you caring if he happens to break skin while he does. You don’t even register the bite of pain underneath the way his cock prods you g-spot so perfectly.

Your own fingers would have been tired by now, no longer able to work that little spot like you need. Simon’s cock, however, is unrelenting. The pleasure builds and mounts uninterrupted, every stroke of his length sending you higher. His body moves fluidly, rolling his hips tirelessly so he can give you every ounce of pleasure your sweet little cunt needs.

You’re creaming around him, a frothy, milky ring forming around the base every time he sinks in and becoming visible when he pulls back. It’s filthy and messy and makes your cheeks burn but Simon seems to not mind in the slightest.

“So fuckin’ messy, love,” he coos, breathy and slurred, “Look at that, pretty cunt needed some cock, huh?”

“Y-Yours!” you manage to choke out.

“What’s that?” he asks, a crooked, teasing grin on his face.

“Y-Your cock! Only needed your cock, Simon,” you pant, reaching up to grope your own tits, pinching and rolling your nipples meanly. It hurts so good, making you clench around his cock. He moans at the sight, his pretty little virgin tormenting your own nipples.

“That’s right,” he hums, reaching a shaky hand down to thumb at your clit, “Keep pinchin’ those pretty tits, sweetheart. Don’t stop.”

You nod your head, unable to form a vocal response from the new sensation of your clit being played with while he fucks you. It feels so damn good that you could go drunk from it all. Everything in your brain is slow, thoughts of only him and how good you feel are all that’s there. Your entire world, right at this moment, revolves around Simon Riley.

He knows it too, a cocky grin on his face as he works you to your orgasm. You dangle, almost helplessly, staring unblinkingly at his handsome face as he works it out of you.

After what feels like minutes, but is probably only seconds, you cum. Hard.

Your head slams back against the pillows, back arching as you cunt clasps tight around him. You cry out in pure, unadulterated pleasure as he fucks you through it. His thumb keeps working your clit as it twitches and pulses under the digit, cumming nice and pretty for him just like he wanted. Just like you deserved.

You cream his cock messily, it drips down his balls and down your ass to the bedding below. So fucking sloppy and wet, a perfect little cunt made to take his cock.

His brows furrow, mouth falling open as his own orgasm mounts and builds. Now that your well-earned orgasm is out of the way, he can finally let go and allow himself to experience it as well.

“Where do you want it?” he grits out, teeth clenched from the ache of holding back.

His balls draw up, heavy and full. He feels ready to positively explode when you gasp, “I-Inside!”

His head falls back, the loudest, most drawn out moan you’d never expected to come from a stoic man like Simon falling from his lips. It’s deep and primal, full of nothing but euphoria as he spills into you. His load is hot and thick, drooling out of the sides of his cock as he slows his thrusts to milk the least bits of pleasure from the orgasm.

When he comes down, he collapses. Your legs lock around his waist and he draws you tightly into his arms, neither of you caring for the way his weight crushes you. All you care about is being wrapped up in his arms where you belong.

He pulls his neck from your chest and kisses your forehead. Then he kisses your nose. Then your lips.

“Pretty,” he breathes, still drunk on the endorphins of the sex so his lips are a little looser than they’d normally be, “Always thought you were pretty.”

“Really?” you prompt, cheeks heating at his confession.

He hums, “Glad you’re finally mine.”

You beam, “No one deserved me as much as you.”

He nods as if it’s the most obvious statement in the world, rolling off of you with a sigh. His cock unplugs your cunt and a gush of your mixed cum comes out, making you whine. He laughs softly, drawing you back into your arms.

You’ve never felt safer and warmer in your life, knowing in that moment that you should have come to Simon all along. There’s no one in the world who would be there for you, more willing and able than he.

this work belongs to rowarn. do not repost to third party websites or use for character ai. reblogs welcome and appreciated!

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