Cherry Pie
A wondering happy birthday to my sweet Cherry @soapsgf who wanted some soft and sweet romantic smut with big dicked Simon. This one's for you, darling <33
Pairing: Simon Riley x fem!reader (Cherry)
Summary: It's been a while since you've been intimate with a partner, and Simon takes good care of you.
CW: MDNI 18+ content, NSFW, cunnilingus, fingering, consent checks, first time between partners, big dick Simon, unprotected piv, creampie
Word Count: 4.2k :))))
Simon was your first partner after a long, long stint of failed dates. You’d met him by chance, out one night with a group of friends when you’d bumped into a solid mass of muscle walking out of a bar. He’d caught you, set you right on your feet with a few words of being careful of your surroundings before seemingly melting into the shadows, despite his size.
The next morning, you’d stopped by a local cafe. The barista called your name and you grabbed your drink, spinning around quickly only to have a heavy set of hands grip you tightly. Panicking for a moment, you looked up, ready to try and fight off your attacker, when you took in the strangely familiar face.
“You’re… you…”
“That’s twice within twelve hours, sweetheart. Starting to think you’re making a habit of this.” His voice was accented, deep, and gravelly, making your hair stand on end.
“I didn’t meant to— I’m sorry—”
“It’s fine, doll. You couldn’t take me out even if you tried.” He huffed out a chortle at that and you felt your face shift into an expression of mild amusement. Then, with a surge of confidence you weren’t even aware you possessed, you met the heavy gaze of his dark eyes.
“No, but I can give you my number, and then maybe you can take me out instead.”
The man blinked, the smile still ghosting on his cheeks as he tilted his head, watching you. Suddenly, it felt like he was scrutinising every aspect of your appearance and you ducked your head, feeling your face heat.
“Ah forget it, sorry, I just—” You’d moved to exit the cafe, but a firm arm wrapped around your waist.
“I’ll take you up on that offer, if it’s still on the table.” Blinking in surprise, you looked up at him. One corner of his lips was twitched up into a smirk, his brow slightly raised and you couldn’t help but feel your lips pull into a grin as you nodded.
“Name’s Simon.” He told you as you quickly scribbled your number on a piece of paper. As you handed it to him, he opened in and frowned slightly. “No name?”
“Take me on that date, Simon, and you might be lucky enough to get it.” The smile that broke out on his face made your stomach flip, and somehow you knew this was the start of something.
•
Several months down, you and Simon had settled into a steady routine. Whenever he was back from deployment, he slotted himself neatly into your life, as if he hadn’t missed a beat. It was refreshing, to have someone like him, someone who was willing to work through things, instead of ignoring them.
Including sex.
You’d first breached the topic with him a few months in. He’d come back from deployment and there was something about him in his gear, still sweaty and dirty from his time out. Simon had stood there, leaning against your doorframe as you’d opened the door and you felt your heart rate pick up.
The look in your eyes had clearly sparked something in him, and he surged inside, kicking the door closed and pressing his mouth to yours. He steered you towards the couch pressing you against the back of it before one of his hands ran up the back of your leg roughly, hitching it around his waist.
In a moment of panic, realising where this was going, you broke the kiss, a firm hand placed in the centre of his chest. Though his brows furrowed, he acknowledged the look on your eyes, and slowly let you down. Fear bubbled inside you at the thought of possibly upsetting him, but he placed a reassuring hand on your cheek.
“It’s alright, doll. Just talk to me.”
“It’s… been a while.”
“We don’t have to do anything,” He said gently, thumb stroking your cheekbone. “Not until you’re ready.”
“But you want it—” A thumb pressed against your lips, stopping your words before you could finish your sentence.
“It doesn’t matter what I want, lovie. If you’re not feeling it, or you’re not ready, I’m not going to force it.”
Swallowing thickly, you looked up into his earnest eyes and realised that, yes, he’s different from the rest.
“I still want to kiss you, though.” Your words were softly spoken, but were met with a chuckle as Simon tilted your head back, cupping your head.
“Kissing I can definitely do for you.”
•
The time came a month or so later. Simon had messaged in the early afternoon, telling you to get all dolled up and pretty because he was going to take you out for the evening. He turned up at your doorstep, dressed in cleanly pressed black pants with a black button-down shirt he’d rolled up to expose his thick forearms. You couldn’t help but let your mouth drop open slightly as he leaned against your bedroom door, watching you as you fiddled with your hair.
Turning around, you got a better look at him, allowing your eyes to unabashedly trace over his broad, thick body. Chuckling, Simon stepped forward, making his way over to you. As he stood in front of you, the soothing scent of cologne wafted over towards you. Unable to stop the sound, you let out a breathy whine and he smirked.
“See something you like, doll?” His hands slid up and down your sides before leaning down to press a kiss against your cheek. “Come on, we’ll be late.”
He’d made you feel spoiled, treating you to an exquisite dinner at some ridiculously fancy place. You were unable to stop your eyes flitting over to him and admiring just how damn attractive he was as the pair of you sat in the low ambient lighting of the restaurant. Finally as you were headed back home, you were struck with the idea that maybe, just maybe, you felt ready. Simon had always made you feel safe, why should this be any different?
When you arrived home, Simon knelt down, lifting one of your legs up gently to remove your shoes. Placing a soft kiss to your knee, he gently lowered it back down with a hand on the back of your calf. He repeated the process on the other leg before pushing himself up to press a kiss to your cheek. He made a move to walk away, but your hand on his wrist stopped him.
Though you didn’t talk right away, Simon stood there patiently, waiting for you to find the words.
“Simon...” You murmured trailing off as the words evaded you, choosing to flutter your lashes up at him instead. He looked at you, eyes darkened, tilting his head slightly as he calculated his next words
“What’s on your mind, doll?”
“I want you.” The words were soft, but firm. Simon, the tease that he was, lifted a brow in mock surprise.
“You want me to do what?” He smirked, staring down at you expectantly. The grip you had on his wrist tightened.
“I’m ready. And I want— no— need you to fuck me, Simon.” You could see the change in him, as if a switch had flicked over in his mind.
“Are you sure?” His voice was rough, layered thickly with desire, but still present enough to look deep into your eyes. “Need to hear those words again, pretty girl.”
“Yes, Simon,” You assured him, chest rising and falling as you breathed heavily, “I want you.”
The words broke his resolve and he dove in to seal his lips against yours, moaning softly at the contact. He’d kissed you countless times before, but even you could feel the difference in this one. It was intense and heated, his hands sliding up and down your back and squeezing at your body before he quickly pulled back, panting.
“Anything that’s too much— too quick— too rough, you tell me, promise?” The gruffness made your hair stand on end, and you shivered in his arms.
“I promise, Si.” Groaning, he pressed his face into the crook of your neck, one large hand cupping the back of your head as he nipped along the column of your throat.
“I’m gonna make you feel so good lovie, I promise.” Letting out a soft whine, you ran your hands down his chest, squeezing the soft flesh around his waist as you pulled him closer to you, pressing your hips forward. Simon’s breath hitched before he let out a growl.
“Bedroom. Now.”
The pair of you hurriedly made your way to the bedroom, mouths never leaving each other’s as you finally felt the doorknob and pushed it open. Having barely stepped into your room, he broke the kiss, spinning you around so he could tug down the zipper of your dress. Moaning softly, he allowed his hands to caress your bare skin as he mouthed up your neck once more. The dress fell to the floor, leaving you almost bare compared to his mostly clothed body.
He spun you around and, with frightening ease, Simon lifted you up, hooking your legs around his waist as he strode quickly over to the bed. Placing you down gently, he pushed you back so you hit the pillows. Nudging your legs apart with his thighs, he ran his hands over your legs, cupped your ass before sliding up your back.
“So fucking pretty for me.” He whispered, eyes heady as they stared down at you, hair fanning over the pillow as your chest rose and fell rapidly. Unable to hold himself back, Simon threaded a hand through your hair, gently pinning you to the bed as he lowered his mouth to your neck once more.
Your hands moved to the buttons of his shirt, tugging them open so you could get your hands on the glorious expanse of his chest. His skin was rough, littered with lumps from old cuts and scars, and you wanted to map every bit of it. He seemed to be doing the same to you. His large, calloused hands tracing up and down your body, worshipping every inch of skin as his mouth kissed down your chest and stomach.
“Lemme taste that pretty pussy of yours.”
Pulling up, he lifted your hips and tugged your underwear off, before pausing, eyes drawn down to the drenched fabric. Running a thumb over it, you watched as his face pulled into a smirk before he tucked the panties into the pocket of his slacks.
“Still feeling alright, lovie?” A brow was raised in question as he looked at you, fingers tapping on your hip as he waited for a response.
“Yeah. Please.” Reaching for his hands, you squeezed them gently, causing him to let out a chuckle.
“Good girl.”
Settling down between your legs, he pushed them apart before dragging his tongue up your wet slit and moaning as he did so. It was wet, messy, and sloppy, but god it felt good to have someone tonguing your pussy like they knew how to.
Drawing your lip between your teeth, you cut off a moan that was threatening to break free when Simon pulled away to stare up at you.
“None of that now, doll. Let me hear you. All of you.” He grunted, sealing his mouth back over your cunt with determination. As he moaned, the vibrations ran through you, making you shiver and gasp. Hearing the sound of your breath hitching, he dug his fingers into your hips, pulling you harder against his mouth. That action made a moan break from you, hands threading through the short, blonde hair as he ravished you.
It wasn’t long before you felt the familiar, toe-curling feeling you’d only been able to give yourself and your breathing change, morphing into soft pants and pleas as your fingers tightened in his hair. Instead of changing his rhythm like you’d had other partners do, Simon kept the same, allowing you to press and roll your hips over his mouth and you needed to find the right spot.
When you did, your whole body twitched as you let out a moan, arching your back as your legs shook. Simon practically growled into your cunt, eyes flashing open to stare up at you, taking in every slight reaction you gave him. Looking down, you stared into his eyes, dark and hungry which caused your stomach to flip.
Brows drawing together, your body shivered and you reached down to grip one of his hands as your mouth dropped open as you felt your orgasm wash over you with a cry of his name. Simon grunted, letting out a moan of his own and held you tight to his mouth as you climaxed.
Breathing heavily, you groaned softly, pushing at his head, but he refused to move, mouth moving down so the ridge of his nose pressed against your clit as he tongued your cunt. He pressed a thumb to the hood of your clit, flicking over it as his other hand kept tight hold of your leg, pressing his tongue deep into you.
Groaning at your taste, he didn’t stop until he felt your walls shaking around his tongue and your hands tugged more viciously at his hair as you moaned loudly. Managing to get your foot into his shoulder, you shoved him back, looking down to see his smug grin, chin wet and shining with your slick.
“Still good, lovie?” Though his face was feral, his voice was soft and questioning. Choking out a laugh, you clapped a hand over your eyes.
“Yeah… just… fuck.” He hummed in approval, pushing himself up to slide up next to you, his hand tracing lightly up your thigh.
“Need a break?” The smug grin was back as he looked down at you, earning him a slap to the chest.
“No, but I can help you—” Before you could even begin to reach down for his trousers, he gripped your hand and pinned it above your head.
“No need, pretty girl. This is about you.”
“But you—” He pressed his mouth to yours, kissing you deeply as you tasted yourself on his lips. Tracing a hand over your chin, he pulled away, looking down at you.
“This is about you.” He repeated, with more sincerity. “For you, at your pace. Do you want to keep going?”
“Yes!” The reply was quick your mouth, barely before he’d even finished the question. A wolfish grin spread over his face and his hand gripped your hip.
“Good fucking girl.” He groaned, hand moving to trail his fingers between your legs. Circling your clit slowly, he breathed soft words of praise into your ear as you whined for him, rolling your hips to meet his rough digits.
“Look at you. So soft for me. So pliant. You’ve been desperate for it, haven’t you? Don’t worry, doll, I’m gonna make it so good for you.”
As if it were the easiest thing for him, he brought you closer to another orgasm. You could feel the heat coiling in your gut as he kept rubbing over the sensitive bud, pinning your legs apart with his.
“Don’t hide from me, pretty girl. Let me see everything. Wanna know how good I’m making you feel, how wet you are for me.”
“Simon…” Your back arched, hand reaching out to grip his body for support. He drew you into his chest, fingers unrelenting between your legs as he held you against the firmness of his chest, covered by a soft layer of fat. Tipping your head back on his shoulder, you gasped out another moan as you came yet again.
“Fuck yes. My good girl. Look so pretty when you come for me like that. Gonna finger you now, yeah? Stretch that tight cunt out nice for me.”
Mewling in his arms, you turned your head, shaking it slightly.
“Cock, Simon. Want your cock.”
“I know you do, greedy girl. But patience for me, yeah?”
“No!” Whining, you pressed your hips back against his. Letting out a huff, Simon moved quickly. Pushing you down onto the bed, he nestled himself between your legs, dress shirt crumpled as your eyes trained down to the swelling bulge in his pants. Smirking, he raised a brow.
“Yeah, pretty girl. That’s why. Gimme your hand.” Grabbing your wrist, he pulled it down so your palm was pressed against his crotch and he thrust his hips forward. Squeezing your hand around him, you took in the full weight and thickness of his cock, and swallowed thickly.
“Fuck you’re big.” You blinked your eyes up to him, and the corner of his lips twitched into a wider smile.
“Exactly, my pretty doll. Need to make sure you’re all nice and lax for me. Need to get that pretty cunt all soaked and messy before you even think about getting my cock.”
Releasing your wrist, he turned his attention back to your pussy, where one of his thick fingers circled your entrance, collecting your slick. Smirking darkly, he leaned down and spat directly on your cunt, making you jerk and moan at the feeling. Spreading his saliva, he plunged his finger into you, and the pair of you moaned in sync.
He was a vision between your legs. Still mostly clothed, but looked debauched with his shirt pulled open and the sleeves rolled up. The black ink on his tattooed forearm rippled as he thrust his fingers into you. Grunting, his jaw clenched as his eyes were trained on your pussy, watching the wetness soak his finger.
“Look at you, so fucking eager for it. Can feel you clenching around me. Think you can fit another finger?” Without much preamble, he slid in a second finger with a low breath. “Good girl. Good fucking girl. God, you feel so good. Can’t wait to feel this tight little pussy round my dick.”
Squirming underneath him, you clung to the sheets, keeping your legs spread for him as your eyes rolled back into your head in pleasure.
“Fuck, Simon… oh my god.” The erotic, slick sound of his fingers entering your cunt repeatedly filled your ears. Panting, you reached out a hand and gripped his shirt.
“No no no, not done yet. You’re getting another in you. Come on, pretty thing. You can do it, you can do it, I know you can. Be good for me, yeah?”
You couldn’t resist. Between the sound of his voice, the way he pinned you so easily against him, the way his fingers curled inside of you…
A third finger pressed at your entrance and you sucked in a breath, eyes flashing open as you stared into his eyes. The fist you had clenched in his shirt tightened, pulling him down as you grit your teeth. Simon lowered his head, pressing his forehead against yours as the third finger slowly pressed in.
A guttural moan broke from your throat at the burn of the stretch, but also from the orgasm that he pulled out of you. Swearing, Simon grunted, his fingers plunging into you a little faster as he took advantage of your climax.
“Good girl. Fuck, look at you. Shit, the sounds you’re making…” His voice cracked as he moaned, breathing turning shaky as you writhed in his arms, pussy pulsing around his fingers.
With a low growl, Simon pulled his fingers out of you with a wet sound as he yanked his belt off with one hand and pushed his pants down. Gathering yourself enough, you pushed yourself up onto your elbows to watch him. As his cock sprang out from his underwear, you let out a shocked gasp, eyes widening as you took in his cock.
It was long and thick, with a ruddy head. His balls hung heavy, making you shift your legs wider in anticipation. The action wasn’t missed on Simon, and he grinned hungrily. Spitting on his hand, he used the combination of your slick and his saliva to pump his cock as he ripped at his shirt, pulling it open so you could admire his soft belly.
The main that left your lips was whiny and pathetic as you stared between his gorgeous body and that glorious cock of his.
“Simon please… fuck please don’t tease me.”
“Believe me, doll. Couldn’t tease you right now even if I wanted to. Need to feel your pretty pussy wrapped around me now.”
Shuffling forward onto the bed, he settled between your legs, tapping the flushed head of his cock on your sensitive clit, making you jerk.
“You sure you want it, sweetheart? Last chance to back out before I’m filling your tight little cunt.” With your chest heaving, you looked up at him through your lashes.
“Fuck me, Simon Riley. And don’t you dare pull out.”
The look on his face turned feral as he hauled you closer, lining his cock up with your wet entrance before pressing in. Your mouth parted wide, but no sound came out as the burning stretch of his cock overtook your senses. Simon let out choked off grunts, fingers clutching into the sheets as he slowly pressed into you.
Shallowly thrusting, he sunk deeper and his hand moved to cup the top of your head, rubbing affectionately before he finally managed to sink in all the way with a low groan.
“I know it’s big, I know. Doing so well for me, takin’ it so nicely.” Resting his forehead against yours, Simon inhaled deeply before opening his eyes, staring down at your face. His expression softened as he reached down to wipe a stray tear with his thumb, caressing your cheekbone in the process
“Simon!” You mewled, rocking your hips as your walls clenched, the initial stretch of his cock slowly fading and the need for more slowly rose in you. However, before you could get a rhythm going, a firm hand pressed onto your hip, halting all movement and you blinked your eyes open.
Above you, Simon’s eyes were squeezed shut with his brows pinched together. His breath was coming out in short pants as sweat beaded on his brow. Frowning, you went to push yourself up to talk to him, but the movement made him release a choked off moan and both of his hands clamped down on your hips, effectively pinning you to him.
“Don’t— fuck— don’t fucking move.” His voice was rough, on edge as his fingertips dug into the soft flesh surrounding your hips. “Jesus fuck, you’re gripping me tight. Don’t— don’t think I’m gonna last.”
Reaching out, you gripped his strong bicep and squeezed lightly.
“It’s okay. Just fuck me Simon please!”
He didn’t need any further prompting. Wrapping your legs around his waist, Simon began to shift his hips forward, dragging his cock in and out of you slowly.
“I know, princess, I know.” His voice was hoarse as he ground himself deep into you, the rough hairs on the base of his cock brushing pleasurably against your clit as he circled his hips.
“My pretty girl,” His chest rumbled as he spoke, almost whispering the words to you, “Takin’ my cock so well. Feels so good, lovie. So tight around me.”
Moaning your assent for him to continue and dragging your nails down his chest, nails that he’d paid for, he finally snapped. Lifting your hips, he angled you how he wanted, throwing one of your legs over his shoulders as he began to fuck into you. It felt like the wind was being punched out of your body with every thrust, but you couldn’t stop yourself crying out with every stretch of his cock.
“Simon… god fuck! Please, need it.”
“Fuck, baby I know. I know you do. Feel so fucking good. So fucking tight and wet around me.” Groaning, he pushed forward, placing a hand next to your head as he folded your body and thrust into you hard. You wrapped your hand around his wrist, using it to anchor yourself as you moved your hips to meet every single one of his thrusts, moaning like you were being paid for it.
“Pretty girl… so pretty on my cock… feels like fucking heaven.” He grunted, panting as he kept his eyes fixed to your face, watching every subtle shift of pleasure that etched itself onto your expression.
“Need to fill you. Make you mine.” His voice was becoming ragged and airy, signalling how close he was to his release.
“I am yours, Simon. Only yours.” Whispering into his ear, you clenched your walls around his cock, making the pace of his thrusts stutter as you felt your final orgasm of the evening get pulled from your lax body, making you gasp breathlessly.
“Oh shit.” Simon moaned, voice cracking as your walls fluttered around him. He grunted, hand gripping onto your hip as he slammed his cock deep into you once, twice before you felt his cock kick inside of you, and he came, his warmth filling you. Lowering his head, he rested it into the crook of your neck as his warm breath fanned over your skin.
It took several minutes before either of you were coherent again. Simon was first, slowly pulling out of you, rolling you over so he could nestle behind you, holding you against his body.
“My good girl. My sweet little cherry.” Soft kisses trailed down the back of your neck as he hummed softly, contentedly, his heart beating steadily against you. This was perfect, you thought, and you couldn’t be happier.
Happy Birthday to you xx
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