Posted originally on the Archive_of_Our_Own at https://archiveofourown.org/ works/11793300. Rating: Explicit Archive Warning: Underage Category: F/M Fandom: Supernatural Relationship: Sam_Winchester/Original_Female_Character(s) Additional Tags: Dubious_Consent, Watersports, Humiliation, Age_Difference, Frottage, Anatomy, Wincest_Adjacent Series: Part 2 of Playing_Bingo_II Collections: SPN_Kink_Bingo_2017, SPN_Kink_Bingo Stats: Published: 2017-08-16 Words: 2037 ****** Wanna Bet ****** by octopussy_(deannawincester) Summary Sam makes a bad bet with a study buddy and she gives him an anatomy lesson he wasn’t expecting. Written for SPN Kink Bingo 2017. Square filled: Humiliation. Notes Sam is 14 in this story and his study buddy is 16. See the end of the work for more notes “It’s the same hole,” Sam insists, not sure why he knows this but somehow absolutely positive he does. “Uh, no, it’s definitely not,” Courtney says like she’s trying not to sound condescending and completely failing. “Don’t you think I’d know? Considering I’ve got a cunt and you don’t?” Sam flushes hot. He knows the word, but he’s never heard anyone, much less a girl, use it so casually. “But it’s–it’s not like you can see it, right?” “I can prove it if you don’t believe me.” “What?” Courtney leans in and Sam’s suddenly hyper aware of how much older she is than him, how long her sleek hair is and how prominent her nipples are in a tank top with no bra on. Which doesn’t mean that she’s right, just that she isn’t going to skip a beat here and Sam’s literally never discussed vaginas one-on-one in someone’s bedroom with the door closed. “You wanna watch?” Sam has no idea what to do with this situation, not with any single solitary part of it. It made sense to help Courtney out in math—he’s a grade ahead and she’s a grade behind and she’s nice to him whereas no one else at Grant High acknowledges him—and it made sense to study at her house instead of in the air conditioner–less double wide they’re renting. But at some point studying became dinner around her family’s table where Sam was by far the youngest, then Courtney putting on something more comfortable which mostly meant taking off her bra somehow without pulling off her shirt and Sam didn’t even know that was possible. And now somehow they’re off of geometry and here instead and Sam has no idea what to say, pulled up short and completely stalled with his sheer inability to predict how this evening has gone and could continue to go. Is he really going to watch a girl pee to prove a point? “What do I get if I’m right?” Apparently he is. “What do you want?” Sam can tell that Courtney can tell he’s not backing down at this point. She and Dean have the same sly gotcha grin. “Your walkman,” Sam decides. He has to share his with Dean and it hasn’t had anything but Metallica in it for a month and a half. “For two weeks,” He adds hurriedly, not wanting it to sound like he wants to steal something from her. Enough people already think they’re thieves and Sam hates to remember that sometimes those people are right. He’d never steal if he didn’t have to. “Okay,” Courtney agrees. “And if I’m right, you let me piss on you.” “What?!” Courtney didn’t pause or stammer or blush. Sam has never seen her look more serious. She shrugs and takes a sip from the soda she’s been nursing since dinner. Sam watches a drop of condensation fall off the can and leave a dark drip on the fabric right over her breasts. “If you really believe you’re right, what’s the risk?” Sam can’t think of any answer that would get him out of this and Courtney knows it. She finishes off her soda in one big mouthful and unfolds off the bed, holding out her hand. She’s probably shorter than Dean, but she’s taller than Sam and standing next to her with clammy palms makes him feel tiny. “C’mon, follow me.” Courtney’s room has an attached bathroom—Sam didn’t even know there were houses like that, not houses normal people lived in anyway—so there’s no real risk of being seen walking hand-in-loosely-held-hand, but Sam still double checks over his shoulder that Courtney’s mom hasn’t poked her head in the room or something before he closes and locks the bathroom door. There’s just enough room for Sam to sit right in front of the toilet and Courtney insists. Sam folds his legs up under him and realizes with a hot rush of embarrassment that he’s actually hard now that it’s processed that a girl, a girl almost Dean’s age, is gonna show him what’s between her legs. He absently wonders about the circumstances the first time Dean saw someone’s pussy. Courtney shimmies out of her shorts and underwear in one go seemingly without a hint of self-consciousness or a thought that Sam’s never seen the full length of anyone’s leg from ankle bone to hips, especially not up close. Her shorts left pale little imprints of their seams on her thighs and her panties left the distinct impression of a bow on the flat of her stomach. She has to side step past him because of the close quarters and she does it without hesitation, but Sam closes his eyes like he needs to preserve her modesty even with her crotch passing a couple inches in front of his face. His stomach flips in a good-weird-sexy lurch he’s never felt before when he realizes that the strong, earthy smell he smells is her. Courtney plops down and scoots backward so that she’s straddling the toilet bowl and leaning against the lid, pelvis tipped upward. Sam glances between her legs and has to look away immediately with sheer self- consciousness. She’s just . . . displaying herself and he’s sitting on her bathroom floor next to an overturned cosmetics bag hard in his jeans. She doesn’t say anything but when he finally works up the nerve to look at Courtney again, she’s watching him with a sort of condescending older-and-wiser expression that Sam immediately dislikes and finds arousing. “Look,” she says. Sam does. He thinks wildly that she probably has more hair in the cute, dark little thatch over her pussy than he does on his entire body. At first, he can’t even distinguish an opening of any kind except for the shadow of her asshole, just the shape of her swollen, pink pussy lips. Then, Courtney reaches down and spreads herself open with the fingers of her left hand. Her pussy’s shimmering and the wetness makes a small noise like the click of Sam’s throat when he swallows hard. “This is the vagina,” Courtney says, sliding the pointer finger of her right hand all the way in. As she pulls out, she changes the angle of her hand and flexes so Sam gets a real good look at the dark pink of her insides. Her finger comes out sticky looking. “Now watch,” she demands. Sam couldn’t do anything else if he tried. For a beat, nothing happens that Sam can see despite his fixation on her pussy. Then all the flesh between her spread lips seems to lift somehow and Sam sees it, the little pinprick of a hole above her vagina, for just a moment before she starts pissing. Sam’s heard other people piss a hundred times, hazard of living in motel rooms with paper thin walls and passing through more gas station bathrooms than the average trucker. He’s never thought twice about it, but now the sound has him pulsing a little in his jeans. After a moment she bears down and the flow stops. “See?” “Uh huh.” Sam’s stuck staring at the liquid caught in her pussy and dripping from her lips. When it finally occurs to him to look up at Courtney’s face she’s grinning. “So,” she prompts, eyebrows raised expectantly. “Huh?” Sam feels muddled, confused. “Was I right or was I right?” Oh. Right. Sam nods jerkily, suddenly afraid but not sure he’s as afraid as he was before they closed the bathroom door behind them. “Well, go on then. Why don’t you sit in the tub? Take your clothes off.” “We didn’t–I didn’t–” Sam stammers. No, no, he can’t be naked in front of her. “Do you want to get piss all over the clothes you have wear home?” “No.” “No? Well you’d better take them off. If you make me hold it much longer you’ll have to wait while I drink something.” Oh right, she never finished. She’s squirming a little, but Sam’s looking at her pussy as he stumbles out of his jeans and she doesn’t seem to leak a drop even with her legs spread. He didn’t even know that was possible. The tub is cold when he sits down and even colder when he leans back, gooseflesh forming everywhere, even down close to his crotch where he feels overheated. Now that he’s sitting down with his legs stretched out in front of him and his little cock—is it little? He doesn’t actually know for sure, just that it’s little compared to Dean from what he’s seen and that means it’s probably little compared to what Courtney’s seen—standing up against his stomach and he wants to cover himself, but he didn’t think to do it before and now she’s seen him plus if he covers up it will look like he’s embarrassed and, well maybe he is, but he doesn’t want Courtney to know that especially since she looks anything but embarrassed even with piss trickling down her crossed legs and her nipples hard when she pulls off her tanktop. She steps over him, foot slipping just a little bit on the ceramic, and barely has time to get her other foot in the tub before it starts again. The stream hits Sam’s stomach, angles down until it splatters right over his cock. He can’t help how he gasps like he’s being shocked. It’s hot and then instantly cold and strong, distinct smelling and it feels incredible against his dick and makes him dirty-sick all at once. Courtney huffs out a little laugh above him. She’s got her hands braced on the walls and her tits look full and huge from underneath and she’s definitely angling her pelvis like she’s testing what makes Sam react the most. He didn’t know girls could aim. She gets him all over his chest and thighs, but seems focused on his dick. Probably because it makes him squirm with the strange not-enough feeling. When he thinks it’s almost over, Courtney suddenly drops down into a squat, smashing her wet pussy over his dick. Sam yelps, grabbing onto the nearest parts of her—a hip and a forearm—just to try and keep his handle on things as his stomach swoops and he comes, spunk making a wet sticky mess that squelches as she rocks, grinding herself down. Her breasts swing dangerously close to knocking him in the face. Her eyes are closed and she’s making short, stunted noises like this hurts. Sensitive and through his aftershocks, the motion of her on him pinches and she feels heavier than he could’ve imagined. When she finally climaxes, his soft dick has somehow slipped between her folds and he feels every throb. They both stink, the mix of sex and urine nothing if not pungent. Courtney stills and opens her eyes with a giggle. “Whew,” she says with an exaggerated fan of her hand like she needs cooling off as if it’s not freezing there in the bottom of the tub with a scant puddle standing around Sam’s ass. She stands up suddenly and a few drops of her come or his come or her piss drip onto Sam’s stomach. She turns just enough to reach the knobs. “Better wash up, huh?” she asks, not really asking. The bath water is too hot when it starts to come up around his balls, then it’s too cold when Courtney plops in, back against the wall behind the tub and shins pressed against the side. Apparently not everyone is as good at getting the perfect bath temperature as Dean. Sam pulls his knees up to his chest to give her space and ignores how his butt starts to inch down. The sound of the water running is deafening and Sam hopes to heaven and hell and god that Courtney’s parents are watching television or something so they don’t hear. “First time touching someone else?” Courtney isn’t really asking, again. She knows, Sam can hear it. Sam nods tensely. “It won’t always seem so awkward,” she says with a shiteating grin that reminds Sam of nothing so much as his big brother. The water’s getting even colder and Sam suddenly feels very young. 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