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www-zoloft-com · 3 days ago

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My first post so i’m so sorry if it sucks :(

Basically the gist of this is that I’ve been collecting imagines in my drafts of Roomate!Simon Riley x F!Reader and all of a sudden this actual full blown fic happened. So yeah, welcome to Roomate!Simon Riley taking your virginity.

Warnings: Minor DNI 18+, Oral F!Receiving, Fingering, Unprotected P in V (wrap it before you tap it folks), Size kink if you put on glasses and squint, an over usage of the word baby, attagirl, etc. (i like pet names), possibly dirty talking i dunno, no use of Y/N, tried super hard not to describe what exactly you were wearing or looked like so, um talk of shitty guys, virginity taking (obvi), mentions of overstimulation but it’s not a big part or nothin, I don’t know what else but if I’m missing something I apologize!

P.S. this was supposed to be dirtier but i don’t know what happened. Simon just became a whore for your pussy.

Word count: 4k and some change

Roommate!Simon Riley who finally gets to fuck you

He knew you were a virgin, you’d told him in a game of truth or dare during a particularly bad storm. The power was out, you’d had some wine, it wasn’t like he’d care anyway, but he did. He thought about it every night when he was alone, hand wrapped around his aching cock as he fantasized milking you dry.

And now, here you were, splayed out in front of him.

It was accidental. You’d just gone on your fifth absolutely atrocious date of the month and walked into the apartment practically sobbing. Ghost pried and pried until you told him what had happened.

“He kept feeding me alcohol and I didn’t care cause I just wanted to fucking do something, anything.”

He’d furrowed his brows, hanging your jacket on its hooks. “What do you mean, do something?”

“I’m so tired of being the only fucking girl that’s a virgin. It’s humiliating. The second a guy finds out they just fucking drop me like some bitch ass pussy.” You always had a potty mouth when you were angry. He normally found it funny, cute even, but all it did right then was make his heart clench. “And of course he was getting me tipsy so it slipped out and he literally said ‘fuck, why’d you have to say that,’ then told me to ‘please get out of his car.’ He said he didn’t want that to be on his conscience, that it wasn’t his responsibility. Like how is that even fair to me?”

He tried to open his mouth to console you, to try and make things better, but his dick was getting harder by the minute and you just kept rambling.

“All I want is for someone to want me. To want to touch me and for just a minute I wanna feel something, I wanna feel good.” You were too worked up to feel embarrassed, but the shame was there, rearing its ugly head and leaving you a weeping mess.

“I’m sorry, I-you don’t need to know this.” Little did you know he was standing there with the world’s biggest boner. He tried to be chivalrous, took your purse and sat it on the table and grabbed you an ice-cold bottle of water, he let you cry and rant while the whole time all he could think about was fucking that virgin cunt senseless until you were writhing on the bed screaming his name.

“Maybe it’s my fault ya know,” He froze at that, snapping back to reality. “I mean I’m the one who decided to keep myself pure or whatever the fuck you wanna call it. Maybe I’m too needy now or too desperate. Maybe I need to just give up and back off and accept the fact that I’m forever and always going to be-” He couldn’t stand it anymore. In three quick steps he was rounding the table and by your side, grasping your face and placing hungry lips against your own.

He pulled you flush against him, taking satisfaction in the way you yelped at the feeling of his bulge against your lower stomach. He kissed you fervently, tongue absolutely stealing the breath from your lungs and leaving your body limp. It was like a starving man having his first meal. His grip on your hip was rough as he squeezed the skin, no doubt leaving marks, while his other hand was behind your head, holding you close to him until he was satisfied.

Eventually, when you were shoving your hands against his chest, he pulled back, gasping into your mouth. His forehead laid against yours, eyes closing as he heaved in greedy gulps of air.

“Stop. fucking. talking.” The next kiss was soft, thumb rubbing circles where the bruises would form. “ ‘m gonna take care of you okay,” Another soft kiss. “Gonna give you exactly what you need, yeah?

The air is knocked out of your lungs and all you can do is nod. He bites your bottom lip at your lack of noise, hand moving down to paw at your ass. “Use your fucking words.”

“Yeah-yes.”

“Attagirl.” Both hands were on your thighs now, tugging you up and forcing you to wrap your legs around his waist. He’s kissing you again, moving swiftly down the hall to his room. You’re not as quick as him, inexperienced lips moving slower around his mouth, and your trembling hands grasping at his neck and jawline.

He practically kicks the door down, slamming it shut with his foot before laying you down softly against the bed. “Gonna take these off,”

Another nod, heat pooling in your stomach at the deep, desperate rasp in his voice. He works quick, and by the time your bottoms are off, the nerves begin to kick in. Your breathing grows uneven when he reaches for your underwear.

“Anybody ever touched your pussy before, baby?” He knew you were a virgin, but that didn’t mean you hadn’t played around before.

“Just-just me.” He can feel the precum dripping from his throbbing cock.

“Fuck don’t say that to me.” He closes his eyes, groaning as he hooks his fingers into the waistline of your panties and pulling them off your body. He doesn’t throw them down with your pants, instead he sticks them in his back pocket, fingers rubbing the cotton back and forth at the feeling of the slick coating their inside. He starts kissing up your legs, hands gripping your thighs and spreading them wide as his warm lips leave open-mouthed kisses against the inner part of your knees.

You’re not breathing at this point, instead just gripping the sheets in silent anticipation. You thought you’d be more excited, but instead there’s just anxiety and insecurity coating every part of your body.

He can feel the tension in your thighs, can feel it even more as he runs his hands up to your stomach, kneading the soft skin of your belly. “Relax sweet’art, got nothing to be scared of.”

His lips are now just above your pussy, tongue swooping down to run across your clit. You’d touched yourself before, you knew what it felt like, but this was different, very very different.

He groans at your soft whimper, moving down toward your wet slit and beginning to kiss there too.

“Fuck can you just-just do it.” You’re rubbing your hands down your face at this point, trying to fight away the roaming thoughts as the warmth of his tongue teases your pussy lips.

“Gotta take my time, get you opened up.”

“But-”

He looks up, eyes soft and filled with understanding. “Jus’ trust me.” He squeezes your skin for emphasis, smiling that familiar smile and easing some of the stress in your gut. You’re now able to recognize the intense heat pooling there.

Once his tongue finally starts moving inside and his nose begins bumping your clit, your head falls back on the bed, quiet mewls coming from your trembling lips.

He didn’t like that you were so quiet, no, he wanted to hear you fucking sing.

“C’mon baby, tell me what you need. Lemme help.” You wanted to, but the problem was, you yourself had no idea what it was that you needed him to do.

“I don’t know-I just-I don’t know.”

He kept lapping anyway, moving up to sucking your clit. That pulled a sound from you, one he’d never heard before. He loved it.

“B-better, that’s better.”

Your fingers were grasping onto whatever they could find, the pillow, the sheets, your own top, but you still weren’t where he wanted you to be.

“Breathe,” He mumbles the words against your core, leaving you shivering. “You ever had your fingers inside you?”

You’d tried once or twice, but it never felt right, just too uncomfortable and too hard to try more than a few minutes. “Yes.” The weight of your honesty lays heavy on your shoulders. “I didn’t like it.”

He was lazily kissing your clit, leaving strained whines coming from your throat. “Gimme your hands.” You obeyed immediately, letting him take your fingers and guide them to his hair. “I’m gonna try, if you don’t like it, you tell me and I’ll stop right then.”

“Okay,” Your voice is weak, nerves making your body feel on fire. You awaited the uncomfortable intrusion, but instead just felt his mouth again. Felt his lips wrapping around your clit, felt his tongue gathering your slick and spreading it wherever he pleased. It made you forget, only for a moment, made your body relax and fingers go lax on his scalp.

He took that opportunity to put a finger in. His were so much bigger and wider than yours, and that once uncomfortable feeling now kind of hurt.

You couldn’t help but hiss, fingernails scratching at his scalp, but you didn’t tell him to stop, and so he didn’t. He kept scissoring you, until eventually the feeling of his finger was more pleasurable than anything. He could sense the relaxation in the walls of your pussy and in turn added another. This time you let out a moan, hips now grinding up to try and get more from him.

“Attagirl,” He whispered softly, curling his fingers in this spot you’d never even known existed.

Now you were fucking singing.

He moaned in response, who wouldn’t want this right in front of them?

“S-Simon.” You’re saying his name, pleading whines coming from your lips. There was a tightening in your belly you’d only felt a few times before, almost like this coil that could snap at any given moment.

He was a feral man now. Fingers squelching in and out of your wet folds, tongue going down on your clit like it was a fucking ice cream cone. Round and around in circles, sucking, biting, kissing, the mixture of that and the movement of his fingers had you writhing, cunt making movie-style noises as your orgasm grew closer and closer.

He could feel your walls start to flutter around him and knew you were almost there. Just a little more.

“Fuck fuckkk Simon,” He’d added a third finger, doing what you thought was filling you to the brim. You tugged, hard, on his hair, pushing his face down as far into your pussy as it could go.

Suddenly that coil snapped, and you let out a to-loud moan, chanting his name like a mantra in between shallow breaths.

“Simon.” Your voice was high pitched and needy, whimpers coming loose as your body shivered with overstimulation.

Simon, Simon, Simon, Simon. He could cum in his pants at the simple sound of your voice.

“Please oh god please, st-” He pulled away immediately, licking up every drop of release you’d given him and letting it rest on his lips. You didn’t have to tell him twice, if you were done then he could be done too, despite how badly he wanted to keep his mouth on your pussy for the rest of his life. The sounds you made, the way you smelled, his dick twitched in response.

“Did so fucking good for me. Sweetest pussy I ever tasted.” He kissed his way up your body, loving the aftershocks that shook your limbs.

He pushed up your shirt with his nose, slipping deft fingers beneath the top and slipping it over your head.

“C’mon, come back to me now.” He was kissing your lips softly, rubbing the sides of your waist to draw you back to reality.

“M’here.”

“Yeah baby, there we go.” He was caressing your skin, drawing you back to his face, his body, back to every part of his being that you felt you were truly seeing for the first time.

“You’re beautiful,” Your voice was a soft whisper as you reached your fingers up to trace his face.

He couldn’t help but to smile, seeing you like this, eyes lidded and face flushed with the post-orgasm glaze, it made him want to fuck you over and over for the rest of his life, but with it there was also a dull ache inside to think that maybe you’d let somebody else see you this way.

“I’m glad it’s you,” Your words make him choke on his breath, the thoughts reeling in his brain pausing for a split second. “I wouldn’t-It couldn’t have been anyone else. Only you.”

Ghost blinked slowly, turning your speech in circles over and over until it made him nauseous. “Glad I can be of assistance.”

“No, no Simon, it's more than that. I only want it to be you.” His lips turned to meet the palm of your hand as he peppered kisses down your wrist, eventually coming back around to touch your lips. He shoves his nose against yours, one hand moving to grab ahold of your face.

“Always gonna be me.” A small kiss as his free hand fumbles for his belt. “‘M always gonna take care of you, always gonna look out for ya.” He was kicking his jeans off now, bulge more prominent within the tight strain of his boxers. “Nobody’s ever gonna touch you again, nobody but me.”

You nod, squeezing his neck softly as you bring his head down to meet yours. “I love you,” The words have been said a million times before. After his deployments, a long day, in between stirring dinner on the stove. You’d both been saying it all along, but no one was brave enough to admit that it was more than surface level, more than just three words in the dictionary.

He found his tongue heavy, brain completely empty as he watched your every move. “Yeah love,” Finally he could speak, he could speak as his fingers unhooked your bra. He could speak as he wanted to see every single part of you, wanted to see you bare and vulnerable in front of him, and then he wanted to hold you like that until you felt like nothing would ever hurt you again. “I love you too.”

You slammed your lips into his as he removed his boxers, his cock standing strong and proud, the red tip leaking precum.

The nerves were back, stomach and pussy tensing at the mere thought of him trying to put it inside you. You didn’t know what the average penis looked like, but his looked fucking big.

Simon could sense the anxiety, could see it as your eyes grew wide and as your forehead creased with worry. “Relax, breathe.” He lifted your legs to rest against his hips, one hand beginning to line up his cock between your folds.

“Simon,”

“If you want to stop, we’ll stop, I promise.”

“No, I-no.”

He kissed you softly, dropping his length to grab your hand and place it against his bicep. “You hold that and you don’t let go. You can squeeze, claw, bite, whatever you need to do, you got it?”

“Yeah,” It was a whimper, a whisper in the wind.

“Look at me alright, keep those pretty eyes on me.” He started to push in, slowly, but the stretch of just his tip already had you crying, eyebrows pinched up and body so tense it felt like you could be snapped in half.

“Fuck, fuck, fuck, fuck, you gotta-you gotta relax baby, just-nngh-just breathe.” His eyes were shut too, the feeling of your tight fucking pussy and nails clawing at his arms like he was a scratching post had him so worked up he swore he wouldn’t even last a minute.

“You can keep going, just keep going please.” Your voice was trembling, eyes pouring out tears as he pushed in a little further. He was barely halfway inside and already his orgasm was right there in front of him.

“Ta-mm-Talk to me baby. Tell me about-tell me about your favorite song.”

You laughed slightly, the sting starting to make way for pleasure. “You know my favorite song.” Each word was strained, but it was there, and you were pushing through.

“Okay then-fuck baby I can’t-you’re so fucking tight, you gotta ease up. Squeezing me so hard I’m gonna bust like a fucking twelve year old in a sock.”

The moment you giggled he sheathed himself in fully, laying his forehead against yours when you let out a pained cry. “I know, I know, I’m sorry, I’m sorry.” He was peppering your face with kisses, trying not to moan as loud as fucking possible. He hated that you were in so much pain, hated that he could feel cool liquid between your thighs that was anything but arousal.

“It’s alright, you’re alright, it’s gonna get better, just try to -mm-” He whimpered unintentionally, and it sent something ablaze inside your stomach.

It took a moment, but, eventually, it stopped hurting so badly, and you were able to open your eyes, removing your nails from his arm only to leave deep indents that had even drawn blood. “There ya go, fuck yeah baby, there ya go.”

“You can-ah-you can move.” He was frantically rubbing your skin with his hands, kissing everywhere his mouth would reach.

“You sure, love are you sure?” He was a writhing mess on top of you, legs trembling along with his arm as he tried to hold himself up. You just felt so good, so warm.

“Y-yeah. Please.” The first thrust was excruciating, leaving you groaning against his lips, but the next one was better, and then better and better and better.

Now you were moaning, singing like the songbird he knew you were. “Fuck yeah baby-jus’ like that, keeping squeezing me like that.”

His voice, so high-pitched and needy, unlike anything you’d ever heard him say. It had you practically yelling with pleasure. He was moving too slowly, it was agonizing the way you were feeling.

“More Si-I need more, please.” He whimpered at your words, hooking his arms underneath your knees and pushing them up to your chest. He started pounding into you, hitting this sweet spot over and over again.

“Oh my god Simonnn, Simon, Simon,” There it was again.

“Ohhhh baby oh baby keep singing, fuck, keeping singing songbird.”

He swore he’d never had pussy this good in his life, and it was his, all his. No woman had ever made him whine like a needy teenager, never made him beg for release because of how badly he just wanted to fill you to the brim with his fucking cum.

“‘M close, I’m so close fuck,” He couldn’t help how fast his orgasm built up. You just took him so well, so warm and soft.

You were getting there, that coil coming back more intensely than last time, but you knew he wouldn’t last that long. “Go ahead Simon-you can-you can cum honey. Please, please cum inside me.”

With a grunt he stopped, absolutely losing his shit inside of you as he shook with the force of his orgasm, moaning so loudly into your ear it made them ring. He was getting after shocks himself, twitching on top of you as it hit him full force.

“Oh god oh god oh god,” He was chanting your name now. The sound made you whine as you laid there, cold and throbbing with need. When he caught his breath, he sat up, kissing your lips tenderly.

“C’mere.” With a whimper he turned over onto his back, leaving your walls wrapped around him.

“Fucking use me baby, do what you need, I got you.” You’d never ridden anything before, had not a single idea how to even begin, but he grabbed your hips, guiding you up and down.

“Set your own pace, do what feels good.” You nodded, closing your eyes as you bounced up and down, rolling your hips forward which drew a porn-worthy moan from your chest.

Ghost threw his head back, thumb fumbling to rub your clit. “Attagirl, you fucking ride my dick baby.” Every time he spoke to you, you could feel your pussy clench, and it’d clench tight. You knew this because every time it did, Ghost would whimper so loudly you swore he was a wounded puppy.

You’d never heard noises like this, never heard of another man being so obsessed with a pussy like this. He wouldn’t stop talking about it, mumbling beneath his breath as you continued to ride him.

You finally found a solid rhythm, and when Ghost began putting pressure on your puffy clit you swore you saw stars.

“Fuck Simon, oh fuck I’m so close,”

“Yeah I know I know, just let it go baby, let it happen.” One more roll of your hips and you were falling forward, clenching around him so tightly he came again. You were both moaning, loudly, bodies trembling against each other as you came down from your highs.

It took you longer, mind fuzzy as you grew more and more sensitive by the second. Ghost noticed the difference in your sounds and pulled out, lifting your hips and laying them back down against his pelvis.

His hands started rubbing up and down your back, soothing the vibrating skin. He was planting kisses all over your face, nuzzling his nose into your hair.

“Did so good for me, so so good.”

You couldn’t help but smile, fingers moving to prod at the fingernail indents on his arm. “‘M sorry.”

“Nah, don’t ever fucking apologize for that.” You closed your eyes as his gruff, burly tone came out of hiding, the deep baritone sending shivers down your spine.

“Is that-was I-” You could feel your brain whirring with a million thoughts, and even though you knew none of them were true, you couldn’t help but feel a pit forming in your stomach anyway.

“What?” His tone was tender, one hand moving up to caress your cheeks.

A part of you wanted to spill every thought you were thinking, let him know every doubt and every worry, but the other part of you wanted to keep this sacred, to keep it this beautiful fever dream that could never be tainted.

“C’mon love, talk to me.”

You heaved in a deep breath, angling your head to look up at him. He met your eyes immediately, holding your face to stay staring at him.

“Was that okay?” You watched as confusion etched into his features.

“I don’t know what you mean baby.”

“Was I-ugh-I’ve never done this before okay I don’t-I didn’t even suck your dick.”

Now he was really confused. “This isn’t about me, this was about taking care of you.”

“Yeah but every time-”

“If you’re gonna say some stupid shit about another guy I’m gonna lose my mind alright. Are you seriously sitting here right now and telling me that you’ve been sucking dick and not once have they got you off?”

You shrug, shame flushing your cheeks and making you turn away, but his grip was strong, keeping you facing him.

“Sweet’art you were fucking perfect. Did you not hear me?”

A shy smile tries to sneak through. “I did but-”

“Nobody’s ever made me feel that way, nobody.”

You let out a sigh, laying back down into his warm skin. “I just don’t want you to get bored Simon.”

The belly laugh that escaped was nothing like you’d ever heard from him before. It shook your body, the loud, deep rumble of a snicker echoing off the walls.

“Bloody fucking hell, I’ve lived with you for four years, if I was bored love, I’d be long fucking gone.” He grunted when you slapped him on the chest, holding his hands up in surrender.

“No need to be sassy Riley.”

“ ‘M sorry, ‘m sorry,” He was showering you with kisses again, fingers trying to tickle your sides.

“Ow ow, no no no, I’m to sore, Simon fucking Riley!” He was chuckling again, rolling you over so you were on your back once more.

He wanted to slot himself inside you again, feel your warmth resting around his cock, but he opted instead to just hold you, to listen to what you had to say rather than combat it with sex.

“Listen here Riley. I’m being serious, okay.”

“ ‘m all ears baby.”

There was a fuzzy feeling in your stomach but you pushed it aside, trying to form the courage to draw out your words. “This was amazing, and I’d do it over and over again, but I can’t-if you don’t wanna be with me I need to know. I can’t do the friends with benefits thing okay, it’s not-I don’t have that in me.”

You opened you mouth to speak, and he could see the downward spiral lighting a fire inside your eyes.

“Listen to me and listen to me good. I have spent the last four years thinking about spending the next four years with you. I wake up and I think about you, I go to bed and I think about you. I dream about you, everyone at work fucking hates me cause all I do is talk about you. You’re everything I have. I fucking love you, more than anything on this Earth I love you. You hearin’ me?” His words were firm, tucking themselves inside your heart and making their own home there.

It was all you’d ever wanted to hear from him, all you ever needed.

You took a moment to analyze his features, the scrunch of his eyebrows, the softness laid in his eyes, he was everything. With a shake of your head, you kissed him ever so softly. “Yeah, I hear you.”

He broke out into a wide smile, lips landing on yours tenderly. It wasn’t a feverish need this time, just one person melding with the other until you felt whole again, complete.

He stopped only to breathe, pushing a sweaty strand of hair out of your eyes. “Let’s get you cleaned up, yeah?” You agreed, blinking lidded eyes as he stood up and lifted your weak body from the bed.

“Not a thing I wouldn’t do for you, you know that right?”

“Yeah Riley,” You touched his scruff, four years worth of evidence to his words flashing through your mind. “I know.”

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