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Virgin!Reader wants to lose her v-card, but doesn’t want it to be to a complete stranger. Not being in a place long enough to actually get to know someone she "man up" and asks her best friend (one of the Winchester brothers) to take her virginity — while hoping he doesn't find it weird or ruins their friendship.
(I don't mind it, but I would really like it if he wasn't secretly in love with her already... idk, sometimes it just makes it feel like then it's for him and not her)
⋆｡ ˚ just once
summary ˚˖𓍢ִִ໋ when you finally work up the courage to ask your best friend to take your virginity, he agrees—not because he wants you, but because he cares enough to make your first time safe and good
pairing ˚˖𓍢ִִ໋ dean winchester x reader ( f )
wordcount ˚˖𓍢ִִ໋ 922 genre ˚˖𓍢ִִ໋ soft smut !!
warnings ˚˖𓍢ִִ໋ explicit sexual content, loss of virginity, soft and gentle sex, use of condom, emotional vulnerability, best friends having sex with no romantic feelings involved, mild anxiety
notes ˚˖𓍢ִ໋ ִ❀໋ consider supporting my work .ᐟ
you’re both sitting on the edge of the motel bed, the neon sign outside flickering through the thin curtains. your hands are shaking in your lap. you’ve rehearsed this conversation at least twenty times in your head, but now that dean is actually looking at you, patient and a little confused, the words feel too heavy.
“dean… i need to ask you something weird.”
he raises an eyebrow, beer bottle halfway to his lips. “weirder than the usual crap we deal with?”
you let out a nervous laugh that dies quickly. “yeah. probably.”
you stare at the ugly carpet for a second, then force yourself to meet his eyes. “i’m still a virgin.”
the words hang in the air. dean doesn’t laugh. he doesn’t look disgusted. he just nods slowly, waiting for you to keep going. he probably already knew.
“we never stay anywhere long enough for me to… you know, actually trust someone. and i don’t want my first time to be with some random guy in a bar who doesn’t give a shit.” you swallow hard. “so i was thinking… maybe we could do it. just once. help me get it over with.”
dean is quiet for a long moment. his green eyes search your face carefully. “you sure about this?” he asks, voice low and serious. “you want me to be the one?”
“i trust you,” you say simply. “and i know you don’t… feel that way about me. i’m not asking for anything more. i just want it to be safe. and kind. i don’t want it to suck.”
dean rubs a hand over his jaw, thinking. then he nods once. “alright,” he says. “if you’re sure. we do this your way though. slow. you tell me to stop at any point and we stop. no questions.”
relief floods through you so fast your eyes sting. “thank you,” you whisper.
he stands up and pulls you gently to your feet. his hands are warm when they cup your face. “no need to thank me, sweetheart. just breathe.”
he kisses you first—soft, unhurried, nothing rushed or hungry. it’s strange at first, kissing your best friend, but his mouth is gentle and patient. he waits until you relax into it before deepening the kiss, tongue brushing yours carefully.
clothes come off slowly. dean talks you through every step, murmuring quiet reassurances when your hands start shaking again. when you’re both naked he lays you down on the bed, covering your body with his own. his weight feels grounding instead of scary.
he spends a long time touching you, fingers sliding between your legs, stroking until you’re wet and breathing heavier. every time you tense up he pauses, checks your face, waits for your nod before continuing.
when he reaches for the condom you almost cry from how careful he’s being. “you still good?” he asks, rolling it on.
“yeah,” you breathe. “just… nervous.”
“that’s okay. we can stop anytime.”
he settles between your thighs, one hand holding himself up, the other brushing hair from your forehead. the head of his cock nudges against your entrance and you tense. “easy,” dean murmurs. “relax for me. breathe out.”
you do. he pushes in slowly, inch by inch, stopping every time your breath hitches. the stretch burns, but it’s not unbearable. dean’s jaw is tight, clearly holding himself back, but his voice stays soft. “you’re doing so good,” he whispers when he’s halfway in. “taking me so well. almost there.”
when he bottoms out you both stay still for a moment. you feel so full it’s overwhelming. a tiny whimper slips out of you.
dean presses his forehead to yours. “you okay?”
you nod, arms wrapping around his back. “move… please.”
he starts slow, gentle rolls of his hips instead of thrusting. every stroke is careful, measured. the pain gradually fades into something warmer, deeper. your legs wrap around his waist without thinking. “that’s it,” he murmurs against your neck. “just feel it.”
the longer it goes on, the better it feels. soft moans start falling from your lips. dean keeps his pace steady, never rough, never rushing. his hand slips between you to rub gentle circles over your clit and your back arches.
“dean—”
“i’ve got you,” he says quietly. “let go if you can.”
you come with a surprised cry, thighs trembling around him. dean follows a few thrusts later, groaning low into your shoulder as he spills into the condom.
afterward he stays inside you for a minute, breathing hard, before carefully pulling out. he disposes of the condom and comes back with a warm washcloth, cleaning you up without a word. then he pulls the covers over both of you and tugs you against his chest.
“you alright?” he asks, voice rough but gentle.
you nod against his skin, tears suddenly pricking at your eyes. not from sadness—just from how safe you felt the whole time. “thank you,” you whisper. “really.”
dean presses a kiss to the top of your head, his hand rubbing slow circles on your back. “anytime you need me, i’m here,” he says simply. “friendship doesn’t change. not over this.”
you close your eyes, listening to his steady heartbeat under your ear.
for the first time, losing your virginity didn’t feel like something you had to survive. it just felt like being taken care of by someone who truly mattered. and even though there was no romance, no spark, no “i’m in love with you”, it was still perfect in its own quiet, honest way.
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SUMMARY : your boyfriend calls and soldier boy makes you answer.
WARNINGS : lust. smut. unprotected p in v. cream pie. cheating. homemade porn. strong language. sob!reader. praise kink. size kink. soldier boy’s cockiness. soldier boy being ruthless. mentions of soldier boy being technically challenged.
A/N : soldier boy can fuck the morals out of me 🤷🏽♀️ yeah, i said it.
I shouldn’t be here, you thought to yourself. How did I get here? The last thing you remember is being at the party, and now you’re in the middle of Soldier Boy’s bed. Your face rubs against his mattress as his pillow cushions your belly. His fingers squeeze your hips while yours grip the satin sheets, hanging on for dear life as he rams into your cunt at an unearthly pace.
Your eyes roll to the back of your head as his bellend strokes your G-spot. His grunts encourage your walls to embrace him tighter, causing his cock to twitch inside you. It had been a while since he fucked a woman with a pussy as tight as yours. Tonight was the first time you met the charmingly handsome supe, and as a result, your dress now lies on the floor of his room, your ass on full display, as he stretches you out. His dick is so deep in your guts, you forget your name.
The giant room feels smaller as the outside world fades away, the air thickening with the smell of sweet sex as your bodies move as one. Moans fall from your lips like they never have before. Not only did he have the looks and the superpowers, but he knew his way around the bedroom. Your toes curl as the pleasure becomes overwhelming. Tears cloud your vision as you feel your high approaching quickly.
Just as you were about to finish, your phone interrupts. Startled, you jump and search for your ringing device. The light from it shines from the nightstand, illuminating the dimly lit bedroom. You want to grab it, to turn it off, but you don’t want to disrespect the anti-hero by doing something other than focusing on his best work. So, he does instead.
“Who’s Jack?”
Oh fuck!
“U-uh...” You forgot all about him. How did you forget?! You were the worst! “M-my b-b-boyf-friend.”
He tosses it on the bed beside your face. “Answer it.”
Your eyes widen, horrified. “Wh-at?”
He responds with three deep thrusts, emphasizing each word. “Answer. It. Now.”
“Ok-kay.”
With a shaky hand, your finger slides across the screen, and the call begins. “Hello?”
You try your hardest not to make a sound, and Soldier Boy knows it.
“Put it on speaker.”
So you do.
“Where’d you go?”
“I was—pulled into a-a meeting.”
“A meeting? I thought you said no business tonight.”
“I—” The man behind you rams you so hard that a gasp stops you from talking.
“Y/N, you okay?”
“Y-yeah.” Your voice cracks. “I’m fine.”
“Doesn’t sound like it.” He says, unsure. “And what’s that noise?” He refers to the skin-to-skin contact.
“Nothing.” You quickly mute the call, and you let out a cry as he brushes your cervix.
“Nuh uh. Turn that off.”
“But—!”
“Do it.”
And like an obedient little girl, you do.
“How much longer are you going to be?”
“N-not sure. Oh fuck!” You accidentally breathe.
A sinister smile curls at the supe’s lips as he witnesses your slip.
“What the fuck is going on? What kind of meeting are you at?”
“I-I—” You let out a loud whimper as the tears finally shed when Soldier Boy lifts your hips and drives into your pussy at a rate that leaves you speechless. His balls slap against your clit, and you can’t hide it anymore.
“Y/N!” A string of moans erupts from your parted lips. “Y/N, you better fucking answer me right now! It sounds like you’re—!”
“Getting railed?” The supe asks as he picks up the phone. “Oh, buddy, you have no idea.”
“Who is this?! When I find you, I’m gonna—!”
“Do what?” He laughs as he continues his penetration.
“I’m gonna make you wish you never looked at my girlfriend.”
“Maybe if you fucked her right, she wouldn’t be in my bed now, would she?”
“You son of a bitch—My girlfriend loves me! You’re—you’ve got to be mind controlling her.”
“Sure, pal. My good looks and charming smile got her upstairs, and now that she’s here, with my dick rearranging her guts, she’s a drooling mess with no thoughts besides ‘more.’”
“That’s it! I’m gonna fucking kill you!!”
He chuckles so hard you can feel it, “That’s a good one. ‘Never had someone make me laugh as I fucked their girlfriend before.”
“Once I find you, you’re dead.”
“We’re in my penthouse. Find the elevators and tell the guards that Soldier Boy gave you permission to come up and watch your girl get fucked into oblivion.”
The call goes silent, but you sure don’t. Hearing how he spoke to your boyfriend made your body go hot. You wanted the supe more than you knew possible. If he were anyone else—even though you wouldn’t have succumbed to another—you would’ve been absolutely mortified. Hell, you still might’ve been if you weren’t so fucked out right now. If anything, it brought you to your orgasm faster.
“That’s it, doll.” He stares at your propped-up ass as it bounces with each thrust. “Cum on my dick while your boyfriend listens.”
He brings the device to your face, and you let out a whine, unable to say a word. What you should’ve said was ‘sorry,’ but how could you? Not like this. The man on the other line hears everything, especially the obscene squelching with every violent thrust. Refusing to listen to any more, Jack yanks his phone away from his ear and ends the call. The line drops, and you inform Soldier Boy. He frowns with disappointment, but finds your boyfriend’s silence amusing after realizing who he was dealing with.
“Guess I gotta send him a video.” He shakes the phone and demands, “Get me the camera.”
You don’t want to, but how can you tell him no? You fight off your climax and go to Jack’s messages. After clicking the ‘plus’ button beside the iMessage text box, you select the Camera option, then switch it to video. You explain that all he has to do is point and shoot, before handing your device over, knowing you’ll (most likely) regret it later. With a wicked grin, he starts the video.
“Look at her, Jack.” He points the phone at your sweaty and contorted face before angling it so he captures your body from above. “Doesn’t she look prettiest from behind?”
You move with his speedy rhythm as he holds your suspended hips with one hand. Through the camera, he watches your ass jiggle each time his dick slams in. He bites his lip, enjoying the view. Maybe I should learn how to use this thing, he thought to himself. It would be great to rewatch homemade porn.
“Go on, sweetheart. Show your boyfriend how hot you look cumming on Soldier Boy’s cock.”
You nod, and without wasting another second, you shudder on the supe’s well-endowed phallus. With screams of ecstasy, you cum harder than you’ve ever cummed before, and the camera caught it all. You should’ve been ashamed that it would be forwarded to Jack, your boyfriend of three years, who’s never fucked you quite like Soldier Boy has, but you weren’t; At least not now. That’s something you’d worry about later.
With a heavy grunt and a twitch of his member, he spews ropes of semen into your tight cunt. Your fingertips grip the sheets as you feel every pulse of his dick, spraying its hot contents onto your gummy walls. After you come down, he leaves you whimpering from sensitivity and the loss of his gigantic cock. He moves the camera lower as he keeps you in position, shedding light on your abused pussy. Your lips are red and swollen, but the attention lies on his milky white cum dripping from your overworked hole. What a fuckin’ sight!
“So pretty…” His thumb gathers your mixed juices, and you whine, wanting more. He brings it to your luscious lips, and without hesitation, your mouth opens wide, accepting his digit. You keep eye contact as you wrap your mouth and tongue around his thumb, licking and sucking it clean. He smiles with delight as he makes the speedy decision. “‘Think I might keep her around for a while. Thanks, Jack.”
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Warnings: praise, pet-names, degradation, explicit references to piv (missionary, riding, cowgirl), fauxcest (use of ‘dad’/‘kid/kiddo’), ben refers to reader’s v as ‘she’, bit of brat/brat-tamer and sub/dom dynamics, slight dumbification, hint of free use (ben for reader), mentions of mirror sex, talking you through it.
will talk you through it — even if, at times, it’s just talking during it.
loves to tease you, in whatever way; overstimulation, edging, talking
asks you questions he knows you can’t answer
he’s heavy with the praise, with the caveat that it’s so disgustingly condescending
he’d absolutely refer to himself as your “dad”
(gross? yes. will he stop? no)
definitely will talk to your pussy as well
pet names galore: “doll” “dollface” “sweetheart” “pretty” “pretty girl” “good girl” “honey” — even “kid” or “kiddo”
will also use some less savoury pet names — “slut” mostly, but he can get creative
(he’ll usually throw in a bit of praise around it so you don’t get too mad, not that he doesn’t like it when you do)
he won’t shy from outright degradation, but it’s for his meaner days
if you’ve been a brat, or you’ve picked a fight, he’s so much worse
he’ll probably be sweet from time to time — given it lets him fuck you longer
he’s much sweeter, almost soft, when you’re making love, but if you’re fucking? you’re getting fucked
see below:
“so fucking wet f’me, doll.”
“what happened to all that big girl talk, hm?”
“thought you fuckin’ hated me, what happened to that?”
“gonna put it in pretty, hold still.”
“christ, relax a little, would you kid? that’s it, good girl.”
“perfect fuckin’ pussy, know that?”
“don’t need me — fuck, is that right?”
“look at the state’ve you. god, do anything for this dick, wouldn’t you?”
“now, c’mon pretty, cum f’me, all over dad’s cock.”
“jus’ the prettiest slut, ain’t you?”
“what? no snarky comeback from little miss feminist?”
“did I fuck all that big talk out of you?”
“too dumb for my cock to use that smart mouth, huh?”
“well? I’m listening, sweetheart. c’mon, tell me how dumb you are over dick.”
“think you can give me one more. c’mon pretty, be good for your dad.”
if you haven’t pissed him off, it’s a whole lot more praise — it’s still condescending, but a little less so
especially if you’re on top
when you’re on top it’s not really a different story
loves to lean back, let you get off, whilst giving you the full running commentary
for example:
“that’s it, honey.”
“know it’s big, but look at you. fuck. taking me so well.”
“wish you could take a look at this view princess, so fuckin’ pretty.”
“jus’ taking what you need from dad’s dick, yeah?”
“shit, already making a mess. you gonna clean that up later?”
“selfish little whore. been waiting for this, hm? been a good fucking girl for this?”
“y’know your tits look so perky when you bounce like that. christ.”
“c’mon kid, keep going, know that pussy just loves bouncing up and down on dad, don’t she?”
“wanna see you make a big fuckin’ mess all over my cock, sweetheart.”
“that’s it, keep going... knew you just couldn’t wait to cum f’me, always such an eager fucking slut.”
“gonna give me one more, ain’t you? turn ‘round and let me see that ass while you ride my dick.”
“gonna miss ‘em tits, though.”
“god. remind me to get a mirror next time I’m out. just gotta see both.”
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MDNI (18+!) nsfw under the cut!
CW: spoiling, oral (fem!receiving) sugardaddy!Ben
w.c: something close to 2k
Part 2
The first time Soldier Boy hands you his black card, he does it like it means nothing.
“Go buy yourself something nice,” he says, leaning back against your kitchen counter like he owns the place. Which, honestly, he practically does by now.
Your dad laughs from the dining room. “Careful, Ben. She’ll bankrupt you.”
Ben snorts. “Sweetheart, if Dior and Prada couldn’t bankrupt me in the eighties, your daughter sure as hell won’t.”
You roll your eyes, but your fingers still close around the card.
That’s the problem with Ben.
Everything with him feels effortless. The expensive gifts. The shameless flirting. The way he looks at you like you’re the only person in the room, even while talking to someone else. He makes indulgence feel normal, expected, deserved.
And maybe it’s pathetic, but you like it.
Like him.
Which is dangerous for a lot of reasons.
For one, he’s your dad’s oldest friend. They’ve known each other forever—military contracts, shady deals you don’t ask about, years of disappearing and reappearing like nothing has changed.
For another, he’s Soldier Boy. America’s former golden hero. Walking ego. Certified menace.
And, unfortunately, insanely attractive.
“Don’t encourage her,” your dad calls. Ben glances at you. “Too late.” His grin is lazy and crooked, like he already knows exactly what effect he has on you.
You hate that he does.
By the end of the week, three shopping bags sit on your bed and your phone lights up.
Ben:
You alive in there or did shopping finally kill you?
Your dad thinks emojis are spyware. I’m not worried.
-----------------------------------------------
You laugh out loud. He knows how to be funny. Atleast sometimes.
Ben:
You free tonight?
------------------
You hesitate.
You know exactly what this is becoming. Not official. Not said out loud. But Ben has started showing up for you. Not your dad. You. Coffee exactly how you like it. Jewelry because it “matches your attitude.” Dinner reservations under the excuse that “your old man hates sushi.”
And every time he brushes your waist or leans too close or calls you sweetheart in that rough voice, something in your chest tightens.
You:
Maybe.
------
Ben:
That a yes?
-------------
You bite your lip. Thinking.
You:
Depends what you’re bribing me with.
---------------------------------------
His response is instant.
Ben:
Use your imagination.
-----------------------
Heat rushes to your face. God.
You really shouldn’t be flirting with Soldier Boy.
Especially not when he flirts back harder.
He picks you up at eight. Because of course he does. Not a driver. Not instructions. Him. He’s standing at your door when you open it, leaning in the frame like he belongs there but then he looks at you and goes still.
“Jesus Christ.”
His eyes drag over your outfit.
You cross your arms, feeling slightly shy under his gaze. “What?”
“That dress should be illegal.” Your pulse skips. “You say that about everything I wear.”
“Yeah,” he says easily. “But I mean it this time.”
He holds his hand out. And after a second, you take it.
Which was a big mistake.
The second his fingers close around yours, your brain goes quiet, because Ben touches like he owns certainty. Like he expects the world to respond to him.
And the worst part?
You do.
Dinner turns into drinks.
Drinks turn into a rooftop bar overlooking the city.
“You’re spoiled, you know that?” you tease as he orders something ridiculous. Because what the fuck is 'The Sacred Mountains of the Pekingese Cloud Gods"? What kind of drink is that?
The place bends around him without trying. Staff move faster and people stare, while some recognize him. Ben ignores all of it, his attention stays locked on you.
He raises an eyebrow. “I’m spoiled?”
“You throw money at problems.”
“And?”
“That’s not the point.”
He leans in across the table. The space between you shrinks. “Sweetheart,” he says, “money exists to be spent. If I want to spend it on you, I will.”
Your breath catches. There it is again.
That.... shift. Heavier. Intentional. Less joke, more truth.
You look away first.
The ride back is quiet, and not comfortable. Tense.
Ben drives one-handed, city lights sliding over his face. He keeps looking at you. Every time you notice, your chest tightens. When he parks outside your apartment, neither of you move.
“Well,” you say finally.
“Wow,” he deadpans. “Compelling conversation.”
You huff a laugh, then the air changes again, making you quickly get out of the car.
“You know, I’m trying real hard to behave myself,” he says.
Silence snaps tight.
Your heartbeat stutters, feeling your palms sweat uncomfortably. “Who says I want you to?”
Then he reaches over, tucking your hair behind your ear, fingers grazing your jaw.
“So pretty,” he murmurs. You stop breathing.
Nobody looks at you like he does. Like you’re something he’s already decided on.
“Ben…” “Yeah, sweetheart?”
Your brain fails. And then you kiss him. It happens before you can think. Ben makes a low sound and pulls you closer to him instantly.
“Oh, fuck,” he breathes against your mouth.
The kiss turns messy fast. Heat. Pressure. Months of restraint breaking. His hand grips your waist hard. Not rough—certain. You can feel how strong he is even when he’s trying not to overwhelm you.
“Been thinking about this,” he admits between kisses.
Your face burns. “Yeah?”
“Sweetheart,” he says hoarsely, “you have no idea.”
And you believe him.
But your mind doesent work fast enough anymore to comprehend that he just sank to his knees infront of you. Not until you feel his hot breath brush against your thighs, you squirm.
"wha-"
His rough hands tug at your skirt. "Need to taste you, Y/n." You only hear him mumble breathlessly, and with that, your skirt is off, bunched up on the pavement. Hes insane, does he really want to eat you out in the middle of the street? Feeling like he can read your mind, He licks a stripe of your clothed cunt, making you shiver. The air itself is fresh, so It clashes wonderfully with the warm wetness of his mouth on your pussy. Finally, he tugs your panties to the side and latches his lips to your sensitive clit, moaning against it. Freak. One of his fingers slowly inches inside your tight hole, but you open up with ease just for him.
He flicks his tongue over your clit and curls up his finger inside of you, making your hands tangle in his hair.
He keeps up the rythm until you finally come all over his tongue, leaving you panting.
After that, things escalate without ever officially changing. Because Ben appears everywhere.
Flowers. Packages. Jewelry boxes on your counter with notes.
'Buy something decent for dinner.'
'Saw this. Thought of you.'
Miss me yet?'
He remembers everything.
Your coffee and the way you take it. Your favorite snacks. The way you hate thunder but pretend you don’t.
On a cold evening, a storm brews up. The wind bangs against your windows as you cuddle up under a blanket. And just when you're about to turn on the tv to watch something, the power goes out. Great.
You always were scared of the dark- but you'll live! -right?
Well, twenty minutes later, there’s pounding at your door. Half-asleep and mildly irritated, you drag yourself over to open it.
Big mistake. Again.
Ben stands there soaked from the rain, takeout hanging from one hand and a bag of snacks in the other. You blink at him. “Are you serious?”
“You hate thunder.”
“I never said—”
“You didn’t have to.” He brushes past you like he belongs there, setting everything down on the counter while rainwater drips from his jacket.
“You remembered that?” you ask softly. It’s such a small thing. Barely worth remembering, really.
But he did remember. And somehow, that alone is enough to make the lump rise in your throat.
Ben pauses, glancing back at you like the answer should be obvious.
“Yeah. Obviously.”
“Well,” you mumble, “it wasn’t obvious to me.”
He walks past you without a word, slumping down onto the couch, leaving you standing there. 's not long before you're snuggled up in his lap tho.
Your dad notices the necklace first.
“Where’d you get that?” he asks quietly, but there’s suspicion tucked beneath every word.
Your hand instinctively rises to your throat, fingers curling around the chain. “It was a gift.”
“From who?”
The question hits sharper than it should. Who does he think he is? “Why do you care?”
“Because I didn’t buy it.” Before you can answer, Ben speaks from the couch.
“I did.”
The room goes still.
Your dad turns slowly toward him. “You buying my daughter diamonds now?” Ben shrugs, completely unbothered. “It’s small.”
“It’s still a diamond.”
“And?”
Silence streeeeeeeetches. Your dad looks between you and Ben while suspicion settles in.
Then Ben says, calm as ever, “She’s worth it.” Your stomach drops. Your dad only exhales sharply. “Jesus Christ, Ben.”
But he doesn’t throw him out, not yet, atleast.
Later, you find Ben standing in the kitchen, staring into the fridge like it personally offended him.
“You need to stop,” you say immediately.
But he doesn’t even look surprised. “Stop what?”
“That.”
“What?”
“Looking at me like that in front of him.” Now he looks at you. “Like what?”
You open your mouth—
—and absolutely nothing comes out.
A slow smirk pulls at his mouth.
“That’s what I thought.”
“You’re impossible.” “And you’re cute when you’re mad.”
Heat rushes to your face. You turn to leave before he can see it, but his hand catches your wrist instantly.
You freeze. “You nervous?” he asks quietly.
“No.”
“Liar.”
With barely any effort, he pulls you closer until you’re standing between his knees.
Too close. Always too close.
“You trust me?” he asks. That hits differently.
You swallow.
“Yes.” Something shifts in his expression then. Not softer.
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