happy wincest wednesday ry :)

the world is full of pain and suffering. so what are your softest sam/dean headcanons?

happy wincest wednesday, lana! <3 sorry this reply is months late lol. But it is A wincest wednesday (for a few timezones west of me) so...

some of my fav soft samdean headcanons are domestic finale+ winchesters:

I love thinking about Sam having soft fucking feelings about the grey coming in at Dean's temples and in his stubble. The crinkles at his eyes. The low groans Dean makes when he gets up from a chair and the appreciative moan he makes when he settles into the impala or into bed.

I love to think about Dean's soft look when he watches Sam sleep. The way he runs his fingers through Sam's hair when he knows Sam won't catch him. He gets a weird thrill out of the soft look Sam gives him when Dean hands him his reading glasses before he asks.

The getting-older caretaking they do for each other so naturally; so fucking married.

On the slightly spicier side, my pet headcanons are full of consensual somnophilia and lazy morning sex.

i’m sure someone’s had this exact thought before but i can’t stop thinking about 18 year old dean seeing 14 year old sam staying at home every night, no friends, just generally being a loner and it hurts his heart because sam is so cool and smart and funny and why can’t anyone else see that? why does he hide himself away?

but now they’re in high school together, so dean drags sam to a party one weekend even though sam whines about not wanting to go the whole way there because “everyone’s just gonna think i’m dumb and boring, they’re gonna think i’m a baby” and dean reassures him, “come on sammy, you don’t even have to talk to anyone, just come and have fun, i’ll be with you the whole time” but then his plan backfires immediately because everyone at the party is suddenly obsessed with dean’s sweet kid brother, all shy and he can’t hold his liquor and it’s all just so adorable, the girls can’t keep their hands off him and dean just goes a little bit insane with jealousy and territorialism. he grabs sam and drags him back to the car and now sam’s pouty because he was starting to actually enjoy himself, the attention felt good, and “we’ve only been here an hour, dean!” but dean doesn’t care, “we’re leaving, sam, this party’s fuckin’ lame” and sam’s like “this was YOUR idea, you’re the one who said i was antisocial” and dean’s just white-knuckling the steering wheel trying to keep his cool, that’s his fucking boy, no one else’s, see the way they touched him? like they had the right? no fucking way. “it was a stupid idea anyway. you’re just a kid” and it comes out so so angry and wrong and the hurt is so obvious on sam’s face, he’s still young enough that he can’t hide his feelings. but dean doesn’t know how else to be when other people so casually think sam is theirs

wincest is so interesting because there are Endless points in their lives where the relationship could go from gen to full wincest and all of them feel equally true. weecest? valid. awkward coming of age? valid. right before stanford? makes perfect sense. pilot reunion? obviously. pre/post hell? Very valid. late season realization? sure. Literally Any Point during the entire run of the show? Yeah.

like that’s… such a unique ship dynamic. they’ve been so Like That for their entire lives that at any point you could slot in a little kiss or whatever and it wouldn’t feel strange. i don’t think it could feel strange. their love runs so much deeper that classic romance/ sexual behaviours just seem like a given

little sammy rubbing up against dean in the early morning, rutting his morning wood against his leg.

dean tells sam the day after that he’s too old to sleep in the same bed as him but sam refuses. every time it happens sammy makes little noises, wraps up around dean like a koala and talks about how much he needs dean. that it hurts and he needs dean to make it better just so dean will touch him even though he’s perfectly capable of doing it himself.

and of course every time dean shushes him and rubs him slowly through his briefs until he cums, because he’s gotta take care of his little bro ∩^ω^∩

i think dean feels soooo guilty about the incest thing btw while sam is like weirdly chill about it similar to how he is about that guy dying in dean's place in faith. to him, the younger one, who has been obsessed with dean pretty much since birth and never known a life without him it's just kind of the natural conclusion of whatever the fuck they have going on. to him it's like, yeah, obviously. but to dean who is the big brother with the whole "look out for him" thing drilled into him so hard it feels like a colossal failure of his duty and i feel like he would worry so much about it being something he did to sam instead of something that occurred naturally in both of them (he'll get over it though) (mostly)

i love sam's voyeurism. watching dean eat, sleep, fuck. don't even think it's a headcanon at this point. dean makes everythin look like porn and you see sam pulling these faces!!! because of course he notices!!! weirdo!!!

Sam wakes up on his birthday to Dean, presenting him with birthday breakfast in bed, (Sam's favorite; pancakes), which they eat together as they watch some random nature documentary on the Tv. Then, after they spend a while making out in the shower, Dean drives them out to a secluded lake beach a couple hours away where they have a picnic, take Miracle for hikes, make out, swim, make out more, and just spend the day together. At sunset, Dean suprises Sam with fireworks.

Ok ok i know we all collectively agree Dean is the biggest pining lovesick for Sammy but, this is a headcanon obviously, but a headcanon that is very strong in head, that Dean wouldn't realize he desires Sam in any romantic & sexual way, because he is simply too deep in his unconditional overflowing love for Sam, a love so ancient that he for him is nature, instinct, it was there since he held the 6 month old Sammy in his arms.

So to me it somehow makes sense that Dean wouldn't realize how this love could a nature such as romantic and sexual, something not much meaningful to him to begin with.

And on the other hand, there's Sam who, watched Dean mature and grow, who longed for joing Dean on hunts, who was spoiled rotten by Dean and his love. The way he even said "i studied you". This makes me consider that teenage Sam would be the first one to identify his own desire for Dean.

Also i know it's nothing new but, it would fit so perfectly for his reason to run away from home. Hell even Jared's comment on how "i realized Sam ran away because he loved his family too much" fits here tho I'm sure he did not mean this jdurididk

Anyway, that's about it. Sam want to suck Dean's dick way before Dean could even dare to dream that. Sam would make the first move, kiss Dean, run away, the rest is history with added explicit incest

I love the idea of one of them finding out the other is in love with them because of a Shapeshifter

happy wincest wednesday! care to share a random wincest hc?

[warning for talk of noncon and sam slander. But not really slander. I talk abt a headcanon where sam is a bit of a cunt.]

Okay most headcanons i have are like. not stationary things. like theyre fridge magnets i move around and take off whenever i want yknow? but one ive really liked recently is early season (1-2) sam being very manipulative. whether he does it intentionally or not. this is somewhat based off of how soulless sam acts compared to other soulless characters -- which accidentally kind of implies that sam is naturally manipulative and mean and his soul/conscience is what stops him from being an asshole.

i love sam being a sweetheart as much as the next guy TRUST ME but i also love the idea that him being nice to victims they talk to isnt out of genuine care but is instead a front he puts on to put people at ease, that his kindness is because he knows his real self (his core self being something similar to soulless sam) is unpalatable.

and that he also emotionally manipulates dean a lot, again, either unintentionally or otherwise. i think its a very tasty delicious idea and its so fucking fun to play with. especially when you combine sam being manipulative with wincest (think puppy dog eyeing dean into having sex with him, or unrequited dean in love with sam and sam using that or holding it above dean, or sam testing deans loyalty in fucked up ways) i know this isnt like. Canon. Its just fun to think about!

Happy WW! What do they think their brother (or other family member if you like) does better than anybody else in the whole wide world?

Omg, it is Wednesday. Happy Wincest Wednesday, and thank you for the ask!

I think they each genuinely think the other is The Best Hunter. Of course at this point it's a given that together they're probably The Best compared to other hunters, but individually they judge their own weaknesses against their brother's strengths, and find themselves wanting.

In the bedroom (or impala. or shower. or...general surface), Sam is the best dirty talker Dean's ever had-- because he knows exactly what to say to hit those buttons (and no hangups about the incest kink, obviously), and gets really verbose when he's worked up. Dean eats Sam's ass the best, and unfortunately for the inflation of his ego, he full well knows it (see prev).

there’s nothing I like to torture myself with more than thinking about what a miserable fucking wreck Dean was when sam was at Stanford. like full-blown non-functional disaster. he can barely take care of himself and he’s utterly useless on hunts and he just can’t MOVE ON. he cannot move on. cant let go. how could he? Because yeah he misses Sam and that’s part of it. but the bigger part is that he never said anything. He never spoke up. he never asked sam to stay (and never would have) but all he can think about now is what if I HAD said something. What if I. And what if he. And what if— would it have made a difference? would he have stayed? for me? And it makes him fucking SICK that he could even have a thought so hideously selfish and so he convinces himself that sam is surely happier than he’s ever been. has to be, right? Away from hunting. Away from their dad. away from dean’s neediness. that to imagine his brother being happy without him is the worst and most selfish punishment dean could ever inflict on himself

there’s something about wincest in the pre-slash era (whenever that is) where i think the dynamic is: one of them does not have sex with men. doesn’t think of them that way, because it feels too dangerous, too easy to slip into those fantasies he keeps locked away. and the other one fucks guys, but only ones who are eerily similar, carbon copies to his brother. the type of resemblance that would turn most siblings off. and the roles could go either way, for either of them. just… the dynamics of the different types of desperate “unrequited” feelings and the way they try to get away from them.

like. dean getting drunk and making out with some tall, long haired guy at a bar. nasty desperate hands down the back of the guys jeans, stifling a sigh that his ass isn’t quite round enough to be sam’s. he has blue eyes, not brown, but dean isn’t looking at his face anyway. fucking not-sam rough in the back of the impala, moaning baby and cutting off before brother, saying sam’s name when he cums, trying not to stare at the army figure in the ashtray. hating himself for it, swearing off it, but always crawling back, chasing the high like an addict. feeling deep in his soul that sam was right to leave, that he’s better off without his sick freak of a brother.

sam being into girls with short hair, accidentally hitting on lesbians because he struggles to be attracted to anything not wearing a crew cut, flannel and work boots. he’s sick, he knows, that’s part of why he had to leave. frosh week drunk, he lets a guy flirt with him, because he’s just tall enough, just different enough, that sam can give himself plausible deniability. his lips are too thin, he’s too gentle, he smells like axe and fake leather, but sam needs something, and this is all he can get. it’s going fine, until the guy— too late now to ask his name— goes for sam’s belt and sam feels like he’s going to puke. the wrongness of it comes over him all at once, like a fever or a hex. clarity pierces his drunken state: not dean’s hands, not dean’s voice, not dean, wrong. at least it gives him an excuse to back out, a good reason to lock himself in the bathroom and sit on the floor, trying to determine if the dry heaving is cheap beer or grief.

girls are— safe. long hair, soft hands, sweet and gentle and nowhere close to 6’1. this way, there’s nothing reminding sam of the absence, nothing pushing against the barrier he’s made around what he really wants. he can be normal.

he knows it’s dean after the first strike, knows his footsteps and his breath and the outline of his shoulders, even now, even in the dark. but sam doesn’t stop fighting, because he’ll have to stop touching dean, and sam can allow himself this one thing, after so long. dean’s leather jacket on sam’s bare arms is making him dizzy, and sam lets dean take him down, the beginning and end of sam’s understanding of desire. a reminder, familiar like dean’s rough palms on his wrists, his weight pinning sam, his shit-eating grin and drawled easy, tiger; sam has never been normal.

hi maven it’s demongirlmeg here for ww… who do u think is more guilty about the incest thing and who do u think gets off on it more??? is it the same brother or different??

simple answer if you held a gun to my head and made me pick: dean feels more guilty but sam gets off on it more (secretly)

more complicated answer, part 1, guilt: they feel guilty about it in different ways-- dean in the traditional older sibling way, i mean, if anything bad ever happens to sam it's his fault, especially with the responsibility john laid on him as a child, but if it really is dean himself that is the "source" of the danger? i think he'd hate himself forever. and if he was abused by john/had a relationship with john at some point? moreso, because he'd feel like he was doing to sam what john did to him, even if the dynamic was completely different. even in like a late-seasons wincest AU where they've been making love sweetly for years, i think a part of dean will always feel guilty. the feeling lessens as time goes on, and their age gap--a terrible thing as teenagers, but practically nonexistent as middle-aged adults--becomes less frightening. but it's still there.

sam on the other hand feels guilty about it in a way that ties into the rest of the shame he feels about himself--his blood, his freakishness, his isolation, his (albeit correct) paranoia that there's something wrong with him. being fucked by/fucking your older brother is something that removes him even further from the normal/good world, connects him to sin, to Hell--this is especially potent because sam believes in God growing up, Sam prays. in all forms, he is afraid of being exposed for who he truly is. from the start they knew you were wrong, etc etc. <3

re:getting off on it (part 2): dean canonically has an incest kink. take it up with 3x01 the magnificent seven. though in that situation he fetishizes twin sisters, it's not a far stretch to say he'd apply that same taboo fascination to his sex with sam. i also think that he is deeply satisfied and it brings him (nonsexual) pleasure when sam is taken care of by him, and sure, that would extend to sex in a sorta kinky way. crossed wires & all that.

sam? similarly--he likes being taken care of by dean, he loves how it's dean, his older brother, with his hands on him, it bring out a special vulnerable part of sam in the same weird way dean feels their connection. in the complete opposite direction, sam also feels the weight of their transgression, how much it connects them to evil and monstrousness, and on the one hand, it's a big fuck you to john and their claustrophobic life, and on the other, it feels good to submit to destiny. also also, sam definitely had a vc andrews phase growing up, and that fucked him up forever in the incest kink department lol. he for sure imprinted onto cathy dollanganger and romanticized his and dean's relationship, especially if dean ever did anything to hurt him. as i am also of the camp that dean was abusive to sam (or at least that spn has subtext for that reading), i do think that part of the reason sam just lets dean hit him or stands any other maltreatment is because he idealizes the unhealthiness of incest. so while dean is just like "hell yea incest kink" sam takes it WAY beyond that into fetishizing the context, and subsequentially feels even more shame about it, and thus the cycle continues<3

ask and ye shall receive (asks)! do you have a favourite secret headcanon that you think the world isn't ready for

serious addiction problems dean my beloved. there's the painkillers angle, developed from hunting and swiping whatever he could find. then there's my personal favourite, numbing the pain of losing sam around stanford era just keeps escalating. almost crashing his car, binge drinking, nothing makes him feel alive anymore. nothing can make him forget what he's lost. he's alone away from john for an extended period of time, and he's got some cash from hustling pool, so he'll try something. fuck, he'll try anything.

*over text*

Dean: im smoking

Dean: and thinking about kissing you

Sam: how romantic