Dean teaches Sam about fingering at a Halloween party in a smoky basement. the girl he's been necking all night is just drunk enough that she doesn't question Dean directing his little brother to kneel in front of the couch between her spread legs. or how Dean takes Sam's hand in his to show him the right shape to keep the pad of his thumb on her clit while he strokes her insides. or how Dean slips one of his fingers and two of Sam's into her cunt side-by-side and says "yeah, Sammy, just like that"
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โalso don't get me started on how Dean gives hands-on instruction to help Sam hone his skillsโ
please do get started ๐ฅน
1,900 words of oral sex later..... (continuation of this wincest Wednesday post, informed by this halloweencest post too)
I'm going to clean this up (I did not even proof it) and combine it with the previous post as an actual fic, but here I am "getting started"
Sam instinctively knows that he's the youngest in the room. It's a high school party, but everyone here looks Dean's age or older. Eighth grade was middle school in Arizona, but here he's suddenly "freshmeat" without walking in a bullshit promotion.
He's picked his cuticles bloody and knows from the pleasant-and-paranoid fog in his head that he's picked up a secondhand high just from sitting here while three and a half joints got passed from mouth to mouth around him. Dean and "Easy Jean" are making out on the oversized ottoman directly across from him. It's not her given name, of course, but he's heard her introduce herself that way. Not to him. She'd crouched slightly like he was even shorter than he is and shook his hand lingeringly and said, "Hey, Sam. I'm Jeanie."
He hadn't known how to respond since she already knew his name and he'd already known hers too; Dean made no less than three I Dream of Jeanie jokes when he started talking about fucking her. "Easy Jean" Jeanie has full, bouncy tits, wide hips, and a belly button ring with a dangly pink gemstone. He can almost see a loopy scribbled heart dotting the "i".
Dean kisses at Jeanie's belly button ring, pulling down the waistband of her miniskirt to kiss lower on her soft belly. Sam looks away, entire body hot when he catches enough of a glimpse to know that there's nothing under that skirt except Dean's hand.
Glazed, crossfaded eyes seek him out and Dean smiles when Sam meets his eyes. Catches him looking back up even though he knows he shouldn't watch this. There's something slick on his fingers when he motions Sam over.
"C'mere, Sammy."
Sam doesn't so much sit as stumble, landing shoulder-to-shoulder with Dean between Jeanie's spread legs. Dean was right, he can smell her. The rest of her smells like aggressively floral lotion, but her pussy smells... warm, human in a way that Sam only associates with sweat except sweat is so sour and Jeanie's pussy is so, so rich.
"Gonna show you how it's done."
Maybe Sam should've realized what Dean was about to do, but he doesn't until Dean pulls at Jeanie's waistband again, kissing at the secret fold on the underside of her belly. Flipping up the edge of her skirt and exposing everything underneath. He mouths at the swell of her mound, burying his face in her pubic hair. Even with it trimmed close, she has more hair down there than Sam.
The line of her slit looks like a secret Sam isn't old enough to know yet. When Dean strokes soft over it, Sam's mouth goes dry but he's also pretty sure he's drooling.
"See?" he spreads her open, revealing the slick mess of her. Before, Sam'd really only been able to see the cleft of it. Between Dean's hands, Sam can see the nub of her clit and the clench of her pussy and the silken folds of her labia. "Gotta open her up so you can really get in there."
Dean opens his mouth wide like he's eating a peach and the sound is the same too, the mouth movement of trying to get in deeper without dribbling juice. Her pleased gasp turns into a giddy kind of squeal that Sam's never heard before when Dean digs in his his nose. Sam can't see it but Dean's tongue must go right up into her.
There's a hollowness in Sam's ears, the music coming distantly, groggily. Maybe he's higher than he thought and having an extended hallucination of being on the floor between a girl's legs, actually seeing what he sometimes thinks guiltily about Dean doing with his girlfriends.
But Jeanie reaches for him, spreads her thighs wider open like there's no one else in the room and it's normal to invite your boyfriend's fourteen-year-old brother to lick you.
Sam thinks wildly, frantically, that he's never even been kissed.
Dean emerges with his chin soaking wet. With Jeanie's hand in his hair and Dean's hand on his cheek, Sam leans in until he can almost taste her. Can almost taste Dean's spit on her.
"Start low and lick up to here," Dean strokes the hood of her clit and she flinches with a giggle. "Then suck."
Sam's tongue feels enormous in his mouth but small compared to Dean's as he sticks it out to catch a shimmering droplet caught in the hollow of her pulsing hole. He makes a little noise and thinks weakly that it's one that's never come out of him before. She tastes like she smellsโstrong and intimate and incredible.
"Good, huh?" Dean strokes the back of his head, wraps his fingers in his hair to suggest how he should move, guiding his tongue up her slit to the hardness of the underside of her clit.
"Suck," he instructs, breathless, and Sam latches on. There must be a right kind of sucking for this, but Jeanie squirms and her thigh wraps over his shoulder and she says "fuck" all gaspy so what he's doing must be ok.
Smelling her and working her in his mouth is all-consuming. She shakes around him and it's heady and powerful doing that to a girl. An older girl. Dean's girl.
Dean's fingers move from his cheek to his ear and Sam's throbbing in his jeans. Weird that he hasn't really been hard, but he is now that the rough pad of Dean's thumb is rubbing his earlobe, fingers curling around to brush the sensitive place behind.
"Yeah, just like that, Sammy," his brother's breath is hot and so, so close. His hand disappears, but Sam can feel it on Jeanie's body below his chin, rubbing like he rubbed Sam's ear. "Don't forget the rest of her."
When Sam stops nursing at Jeanie's clit she whines. He's a little cross-eyed but he can see where Dean's rubbing: her asshole. Dean pushes against it with the broadest part of his fingers, smearing wetness into the wrinkles of it, but not quite penetrating. It flexes under his fingers and Sam sucks in a breath that probably gives away the worst, most abhorrent thoughts he's ever had about Dean. If he looked up, Dean would be looking at him with full knowledge, he's sure.
"Put your tongue in." Dean instructs quietly, like they're telling secrets after lights out. "Pussy first, then in here." pushing in enough that Jeanie starts to open to him.
It feels awkward, tilting his head to get the right angle. Her hole is further into the folds than he expected so he has to press his whole face in. He can feel when Dean slides a finger into Jeanie's ass. She arches up, but Sam can't hear what she's saying, just the wet sounds of his mouth and Dean's hand.
She's so hot inside, every bit of her quivering and clenching around his tongue, like she's directing how Sam should fuck his tongue in and out. Just when he's getting a rhythm, Dean tugs at his hair, leading him further down. Sam's terrified of the taste, of the filth of it, but he's too far gone to put up any resistance, mouth swollen and feeling years older than it did walking into the party a couple hours earlier.
Her asshole mostly tastes like skin and the spitty, slick mess that's soaking into the ottoman under her. It's darker and stronger and Sam finds that he likes it. Wonders if Dean likes it or just does it because. Wonders if his would taste like this too, if Dean would like it.
Dean moves beside him, pushing Jeanie's legs further apart. He sneaks his face in above Sam, slipping his tongue into her body where Sam's just was.
Jeanie whines and they move in tandem. Sam's not sure who's touching him, but he now knows what Dean sounds like when he gives head and there's no coming back from that. Some of Dean's spit hits his cheek and Sam goes dizzy with how urgent his arousal feels.
There must be some cue Sam misses with his face buried, but Dean pulls back. Puts a hand on the back of his neck until Sam does too.
Dean's looking at him when he lets him up. The expected hesitation doesn't even flicker across Dean's face before he leans in and puts his tongue in Sam's mouth. Sam's helpless noise is a yes and a cry for help. He wants Dean to lick Easy Jean from the backs of his teeth where it's making them itch, but he's certain he should feel more... familial about it.
"Good job, kiddo." Dean's eyes are clear and his voice is confident. Sam wants to disappear. Wants to kiss him again.
But he falls back on his ass when Jeanie drags Dean up by his shirt saying, "Fuck me, baby. I need you in me." and expertly opening his jeans. Sam's way too close to them, but he doesn't move, just sees. Dean's dick looks huge, but maybe Sam's is just small, and his pubic hair is a longer tangle than hers. He's never noticed if his own dick smells different when he's hard, but Dean's does. Dean smells like sex and Sam wants to throw up; he's close enough that he could touch Dean's privates without even fully extending his arm.
"Your boy did so good," Jeanie pillowtalks Dean.
"Yeah? You like his lil mouth?"
His little mouth, like he's a kid. And he is.
"Mmmhmm. You're a good teacher," it comes out as a gasp when Dean fucks deep into her with a squelch.
Is Sam supposed to jerk off? Is he supposed to leave? Are other people watching them do this horrible thing? Will they call him easy in the halls at school on Monday?
He freezes and stares at the glimpse of Dean's dick he gets and the shallow part of every thrust. At the way Jeanie's pussy clings to it like begging him not to pull out. Sam wonders if her asshole would do that too. Wants to ask Dean to show him.
She pets Sam's hair and takes up a big fistful of it when she comes. Hangs on, moaning uh uh uh yeah, until Dean unloads inside her with a low animal groan.
When Dean talks about putting his mouth on a girl, he talks about doing it after too. How vulnerable and quivering she'll be inside when he puts his tongue in the space his dick made. Sam braces to be pulled in, terrified of the pearlescent gleam of Dean's cum leaking out of her.
But Jeanie releases him so she can get a hold on Dean's head and ride his face when he starts slurping at her. Sam finally runs, but it's more like an uncoordinated scramble. When he gets out of the basement, he sucks in big gasps of air, frantically scrubbing his face with his sleeve, licking the fabric until his tongue tastes like lint instead of ass. He's crying, but not retching even though he'd probably feel better if he puked.
Kids who are grownups look at him worriedly when they pass and he just wants to escape. But he rode over with Dean. Can't go anywhere without him. So Sam waits.
๐samdean sharing a bed (because it was the only motel room open that night) turns to first time dry humping ๐ and send
picturing sometime in season 3 when their emotions are high all the fucking time because, well, threat of hell.
they get to this motel and it's been a long couple of days spent driving mostly through the night and there are only single-bed rooms. it's probably a double not even a queen so you know they're s q u e e z e d together
they just want to sleep, running on fumes, trying not to make it a thing as they're jostling and trying to get comfortable
they end up awkwardly spooning and trying to keep their hands to themselves so it doesn't get weirder. they're finally moving toward sleep when Dean shifts, hand just barely brushing the small of Sam's back, and inhales the scent of his dirty hair
Sam presses back before he really decided to do it and. Dean is hard. and they both freeze and listen to how loud their breath is.
but Sam reaches back and grabs Dean's hand, pulls it so Dean's arm is around him and grinds back. it starts on their sides all spooned up like that and ends with Sam desperately grinding into the bed with Dean between his legs, Dean's arms wrapped around him and Dean's nose pressed into the curve of his neck. so close together that it's not even like fucking, it's like the roll of a wave as the tide comes in
whatever you do don't imagine Dean putting his dick in fun dip powder and convincing Sam it's ok to lick it off and it probably tastes better than the stick that comes in the package and he should check to see
(is fun dip still a thing? y'all remember this horrible candy??)
๐sam unconscious after a hunt and dean takes him back to the motel but itโs been a while and he hasnโt woken up yet so dean starts to get some ideasโฆ๐
I'm picturing something that needs time to wear off but that Dean knows isn't gonna kill him so there's all this... waiting. Dean keeps looking at Sam's limp body on the motel bed to make sure he's breathing. he is.
Dean showers and Sam's still out. Dean eats and reads some weather reports and watches a rerun on tv and Sam's still out.
Sam's shirt rode up when Dean hauled him onto the bed and Dean starts to look at that patch of pale, vulnerable skin right above his waistband instead of at Sam's chest when he checks his breathing
starts to wonder. does Sam trim? does his dick look related to Dean's? would Sam's jeans really just slip off his hips without being unbuttoned like they look like they would?
Dean watches another rerun and Sam is still out. stomps around and makes a ton of noise because he's bored and his thoughts are starting to freak him out. but Sam doesn't stir
Dean tells himself Sam wouldn't careโhe's private but not so private that Dean's never seen him naked. he lifts Sam's shirt just a little higher and watches his belly move
then freaks himself out and has to walk himself around the entire motel. except what if Sam wakes up and he's not there? so he goes back and all he can see is the low shape of Sam's belly where it starts to become his groin and Dean just has to see...
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๐ dean drops sam off in baby at the edge of a forest and tells him to start running! Goes and parks then starts the chase! ๐
dude, nonnie. how have you read my actual mind
literally yesterday I was mentally writing a fic wherein Dean drives them way way out (in my head it's a cornfield) and parks the car and tells Sam to run because when he catches him, he's gonna rape him
and Sam's eyes get all blown out and his breathing gets wet and heavy and Dean says, "better go while you still can" (and maybe if that Sam doesn't, Dean is gonna hurt him so he won't be able to)
and Sam starts to think he'll maybe get away right when Dean rips him down with one hand twisted in his jacket and the other in his hair
Sam gets all this loamy soil in his mouth and his eyes, scrabbling to try and get away while Dean strips him out of his jeans and fucks into him dry and it's the worst it's ever been and Sam's sobbing
and when Dean's done, he just goes back to the car and waits for Sam because he knows that's the only way for Sam to get back to civilization. and Sam leaks cum and blood all over the seat on the way back to the motel