𝕂𝕚𝕟𝕜𝕥𝕠𝕓𝕖𝕣 𝕍𝕠𝕝. 𝟚𝟙
ᴋɪɴᴋᴛᴏʙᴇʀ ᴠᴏʟ. xxɪ. october 21st, 2025. feat. by democracy, dean winchester/virgin!reader. curvy/mid-size reader. loss of virginity. semi-unprotected sex. face sitting!! oral f. receiving. multiple orgasms. slight overstimulation. dean being a sweetie. aftercare. hickies. I'm a munch!dean truther. lots of consent. consent is sexy.
approx. 2800 w this one is big and long like dean
Main Masterlist. Kinktober Lineup.
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ɴᴏᴡ ᴘʟᴀʏɪɴɢ: ʙᴀᴄᴋ ᴛᴏ ꜰʀɪᴇɴᴅꜱ - ꜱᴏᴍʙʀ 0:01 ❍─────── 3:18 ↻ ⊲ Ⅱ ⊳ ↺
"The banishing sigil requires equal parts virgin's blood, holy oil, and consecrated graveyard dirt mixed with black salt. Enough to draw the symbol four times. Got it?"
Sam chuckles. "Yeah, Bobby, we got it."
"Don't come cryin' to me if you muck it up, idjits."
Dean rolls his eyes. "Ah, Bobby, he of little faith—"
The line goes dead.
You sigh, opening your notebook where you keep the apothecary inventory written down. It's all in Baby's trunk, tucked in the corner in small bottles. "We have everything we need. Just gotta get a clean IV kit."
Sam nods. "I have one in the first aid kit."
You sigh, rolling up your sleeve. "Always bleeding for the Winchesters."
Dean's eyes widen, darting between you and Sam. "Wait. What are you...? It's not gonna work. You need a virgin's blood—"
"Got one right here," you deadpan.
"You're not a virgin," Dean says, "I mean, look at you."
"I'm sure whatever insulting thing you're planning to say is very clever, but can we just get this over with?"
Sam prepares the kit.
Instead of being confused, Dean's face has changed to offended. "How come he knows and I don't?"
"Where do you think the last vial of virgin blood came from, De?"
"I don't know!" He pauses, remembering the last case you had that required it. It was a smaller amount then, and because you and Sam were handling the research stuff, he'd been the one to prick you. And Dean never asked.
You decide to let Dean stew with his weird feelings about the virginity problem, offering your arm for Sam to tourniquet your bicep and prick. After he gets the blood he needs, the three of you get the case wrapped up before midnight. Sam decides to go to bed, but you and Dean head a block down from the motel for celebratory beers and pub fries.
He keeps sneaking glances at you across the table, and you know what he's thinking because he's Dean, and you've been hunting with him since he and Sam ran into you on a job back in '06. Two years later, you're inseparable. Sure, demons and monsters and all that suck, but they're the closest thing you have to family.
"Spit it out, Winchester."
"I guess I just don't get it."
"Get what?"
"How you're a virgin."
You blush, then scoff. You know why. You're not quite plus-sized, but there's a little more of you, and in the age of low-rise jeans and flat bellies, it's hard not to feel like you're not enough, or too much, rather. "It's not rocket science."
"I just don't understand," he says. "I mean, come on. You're gorgeous, and smart, and wicked funny. A better shot than Sam, but don't tell him I said that."
You scoff. "You don't have to say that stuff."
Incredulous, he knocks back another sip of his liquor. You went for harder stuff an hour ago, which is the only reason you two are comfortable enough to have this conversation. "I know. I'm not doin' it because I have to, I'm doing it because it's a goddamn crime you haven't gotten laid. Unless it's not your thing. Like you, uh, not-sexual?"
"Asexual," you correct him. "And no, I'm not asexual. I just... Guys don't look at me like that."
"You're kidding, right?"
"Dean, seriously, I'm not..."
His eyebrows shoot up so high they crease his forehead. He stares at you like you're a Martian. "Two guys have hit on you today, just in the time we've been at this bar. Hell, I've been flirting with you since Day One. I just assumed you weren't interested, or maybe you have someone better in mind." Honest Dean comes out when he switches from beers to Long Islands. A small brush of insecurity colors his tone.
You can't believe he thinks there could ever be anyone better. How could you not be a little in love with Dean Winchester? He makes everyone he talks to feel like the only person in the room. It's magic. Not to mention, he's hot as hell and tall and smarter than he gives himself credit for.
"I didn't realize you were interested," you admit.
"Well, I am."
You can't remember your own name right now. His eyes are locked on yours, and the bar is so hot, almost too hot. You're reeling, trying to find a response to his words.
"Even now?" you finally ask.
"If you'd do me the honor," he says, and that smirk of his lights up across his mouth. "I'd love to be your first."
You reach for your coat slowly, the heat traveling from the apples of your cheeks down your neck, and then lower. "Guess we'll have to find another virgin next time we need some blood."
He throws two twenties on the table, and then he pulls you into the night.
You have your own room at the motel, which is a necessity when you spend the majority of your time with two stinky overgrown boys who argues most of the time. You reach for your key with a shaking hand, a little nervous. Dean's closes over yours, steadying your fingers.
"You okay?" he asks. "We don't have to—"
"I want to," you assure him. "I'm just scared I'll be... bad at it."
He chuckles, unlocking the door and pushing it open for you. "I doubt you could ever be bad at anything."
The door closes. He backs you into it, locking it behind you. As the chain slides into place, he cups your chin, lifting your face to his.
"Tell me to stop if you want to stop," he murmurs. "I swear, I will."
"Kiss me," you plead.
He does.
And holy fuck. It's better than you imagined.
His lips find yours and learn your rhythm right away, falling into effortless form. He cups your face with two big, rough hands, and you scramble to hold the front of his shirt for purchase to stay balanced. It's a world-rocking kiss. The kind of kiss that'll haunt you for days after. When his tongue meets yours, and you moan softly, you feel him everywhere, and your desire becomes a lit match.
You're not a virgin because you want to be. You've just never had the opportunity, and apparently, you're oblivious. But it doesn't matter now because your best friend, Dean, is taking care of you. You'll be okay because this is your Dean, and you trust him.
One hand slides under your shirt, skimming your belly before tugging at the hem. "Lift your arms for me?"
You do.
He chokes on his breath when he sees your bare chest. Ample cleavage spilling out of your bra, breathless, face flushed. Your hair is wild from his hands, and then he's on you again, kissing and cupping your tits through your bra, and when his thumbs roll over the cotton and make your nipples harden, your knees almost buckle.
He reaches for your hips with both hands, starting to tug you up.
"What are you?"
"Hold on tight," he says, and then he lifts you off the floor. Your legs wrap around his waist, and you giggle, then start to panic.
"Dean—"
"What?" he asks, soft, careful. "You want to stop?"
"No, it's not that. It's just that I'm..."
"You're what, baby?"
Baby. Fuck, you love the way he says it. "Heavy."
He snorts. "I've carried Sam out of a burning building and hauled his drunk ass around plenty of times. You're like a feather compared to that giant."
You know he's not kidding. He doesn't seem to be straining a muscle holding you, and so you let all the voices fall away as he kisses you again, grinding his hard cock against your core. You can feel him heavy in his jeans, just as affected as you are, and part of you is amazed that you're making him feel like this.
"Gonna get you ready," he says, his voice thick with want, rumbling out of his throat. He sets you down on the mattress, and you feel him unzip your jeans. Reflexively, you lift your hips, and then he has you down to that bra and your damp panties, which have a very noticeable wet spot on them.
You swallow hard, wondering if you're supposed to be self-conscious, but the way he looks at you with such raw amazement makes you think you don't have a thing to worry about.
He kisses your neck, sucking little marks against your collarbone and the swell of your tits. With three fingers in a smooth flick, your bra is unclasped, and then it's cast somewhere behind him. He marvels at the way your tits fit in his hands, too big for him to hold all the way, and the sound that comes out of him is so deep and primal you ache.
Then he sucks one nipple into his mouth, and you nearly fly off the bed. He just chuckles, tweaking your other one with his fingers, playing you like a violin under him until you're almost begging him to touch you there.
His hand slides into your wet panties, and you sigh with relief. He parts your folds with two thick digits, swirling around your clit, seeing which touches make you moan the loudest.
"Okay?" he asks.
You nod.
He starts working you open, and when his first finger finds your entrance, you could sob with relief. He pushes one in you first, stretching, feeling, working the spots that make you feel like you're floating, and then he adds another, fucking in and out of you at the same speed he's stroking your clit. You bite down on your lip, trying to muffle the sounds, but the closer you get to the edge, the harder it is to keep it down.
"Want to hear you, baby," he says, using his free hand to remove your lip from between your teeth. "Make some noise for me, sweetheart. You close?"
You nod, moaning his name.
"That's good. Cum for me. Wanna feel you squeeze my fingers, okay?"
You nod, and then seconds later, you explode, the coil in your belly unraveling as you grind against his hand, writhing and trembling. He kisses you through it, touching you until your tremors stop, and then he takes his slick hand out of your panties and licks his fingers clean.
"Want to see you," you whisper, your voice small, almost fucked out already.
He steps back, slowly taking off his clothes one article at a time. You've seen him naked before, mostly because Dean has always been very comfortable walking around in any state of undress, but this is different. This is heated, and it's just for you.
When he's down to just his boxer-briefs, his cock outlined in the thin fabric, pre-cum forming a wet spot in the light blue material, your mouth waters. He's big, and you're not sure how he's going to fit, but you want to try, because he's... everything you never dared to wish for.
He lays down on the bed beside you.
"Do you have a condom?" you ask.
He shakes his head. "I mean, I do. In my room. Next, uh, door, but I wasn't plannin' on that part yet. Want to make sure it doesn't hurt. To do that, I need you dripping."
Your breath hitches.
"Sit on my face," he says.
"Dean..."
"If you give me that 'I'm heavy' shit again, I swear to God, I'm gonna fuck you in front of a mirror until the only thing you can say is that you're perfect."
And it's a threat you'd like to see come to pass, one day. But you know he wants this, and you can't deny you're curious about the way that stubble would feel between your legs. You straddle him, and impatiently, he yanks you up and over his shoulders, planting you on his mouth.
And you nearly melt.
Your hands hold the headboard as his tongue spells his name on your clit, sucking and teasing, and then his nose bumps against that same sensitive nub as he devours your cunt, working you open with his tongue. You cum again, and he doesn't let up, doesn't let you recover. Your orgasm seems to last forever, and as he slurps everything you give him greedily, you scream his name so loud that everyone in the motel knows it.
When you finally fall off his face, spent and oversensitive, he kisses your shoulder. His mouth is slick with you. "I think I made you squirt. Like Niagara fuckin' Falls. That was hot."
You'd be embarrassed normally, but this feels too perfect to be embarrassing. He kisses you again, slower, letting you taste yourself.
"You got condoms, baby?" he asks.
You shake your head.
"Let me throw some pants on, I'll go get one—"
"I'm on the pill."
His eyebrows shoot up again, eyes bulging in shock. "I thought..."
"For period stuff, Dean. I need to get you a woman's health magazine."
"Gotcha. No need. Are you saying what I think you're saying?"
You nod. "Want to feel you. All of you. Are you clean?"
"Got tested recently. Sam was giving me shit, wanted to be sure."
"Do you use protection with, um, other girls?"
Now he looks lost. "Other...?"
"Aren't there others?"
He shakes his head. "Baby, you've got me so hooked on you I can't see anyone else. It's been months since I... I mean, come on. Been hung up on you." He says your name softly, and you might cry because of how tenderly the word sounds on his lips. Your name is so beautiful when he says it.
You kiss him again. "I've been hung up on you, too."
He smiles against your lips. "We can come back to this conversation later. I need you, baby. I need this. Fuck. Are you ready?"
You nod.
He spreads your legs further apart and shucks off his boxers before settling between your thighs, squeezing the supple flesh of them reassuringly before he guides himself between your folds. He looks at you as the blunt head of his cock slips against your wet heat, and when you nod, he starts easing inside.
It doesn't hurt, but the pressure is definitely different. He's bigger than your fingers and all of the toys you've experimented with, but it feels nice, being stuffed with Dean. When he finally bottoms out, you're stretched to the brim, nearly overwhelmed with how much he fills you out. You can feel him nudging your cervix; he's so fucking deep, and you're so close just by the way he strokes every gummy spot with his thick length.
He blows out a breath, shaking.
"Dean?"
"Sorry," he laughs, a little sheepish. "Just trying not to cum is all."
"Oh!" you exclaim softly.
An experimental roll of his hips has you both moaning. "You feel so good, baby," he groans, starting to move in and out, slowly stretching you further before sliding home again. "So tight. So perfect. Like you were made to take me. Fuck. That's it. That's a good girl."
You start rolling your hips to meet his thrusts, and you can feel what it does to him as he holds you a little tighter, his control slipping. He starts to fuck you harder, bringing one of your legs up over his shoulder, and the new angle makes you tighten, another orgasm about to make your world burst with stars.
"So beautiful when you cum. Fuck, you're just so beautiful. So good. Oh, baby," he murmurs. "That's right. Just a little more. Hold on a second, want you to cum with me."
He starts getting more frantic now, skin against skin slapping, and you're so wet you can hear it, and he's an animal panting over you, finding the places that make you sing again and again with his cock. His name falls from your lips until you can only make sounds, soft little whimpers.
And then he cums with you, painting your cunt white with hot ropes of his release. You feel it pooling between your thighs when he pulls his softening cock out of you, relaxing beside you on the bed once more.
He pulls you into his chest, stroking your hair. He reaches beside the bed for the tissues with one hand, cleaning the mess between your legs so tenderly before he holds you tighter.
"You alright?" he asks, his lips pressing between your brows.
"Yeah," you whisper, "I'm perfect."
"Good," he says.
"Hey, De?"
"Yeah?"
"Can we do that again?"
He nods, trying and failing at hiding his smile. "If you'll have me, I think I'd like to do this a million times, and other things too."
"Boyfriend things?"
He kisses you as his answer, then whispers his reply against your mouth as he rolls you onto your back again. "Boyfriend things."
I miss Birdie!reader so bad. The friends-to-lovers pipeline for Dean Winchester is my favorite. After Kinktober, we can be right back to the slowburn ;) Thanks for reading!! Feel free to check out my series or other Kinktober installments! And drink some water!! Just because you came to my page thirsty doesn't mean you gotta leave that way.
