#transfem dean winchester

[platonic-soulmates-gencest]

I read about crossdressing Sam so now I'm bringing you crossdressing Dean! (kinda nonbinary actually)

It's already canon that Dean has tried out lingerie and liked it. So my take is that it goes downhill from there. He's hiding it ofc. How could he not? But those years when Sam is at Stanford and John ditches him, Dean gets a bit bolder about his habit.

At first, he starts wearing skirts and dresses inside his motel room. He's alone. Nobody's seeing him. It's fine.

Then he gets greedy.

He knows he has a pretty face. It's not hard to put on a wig and some make up.

It's easy actually. Dean loves the feeling of it.

Making his body look more female is a big hurdle though. He would intentionally get skirts with tight waistbands and he would tie all his dresses with belts as far as they could go. He tries corsets. He finds scarfs to hide his adam's apple. He wears jackets with long baggy sleeves so his biceps won't stand out. He wears long dresses and skirts to hide his thighs. But there's no way to fully hide his legs under the knee so he shaves. And he LOVES the smoothness there.

He knows that he's playing with fire. John might ask him on a job any minute. What if Dean got hurt? What if John had to take his pants off and he show his shaved legs?

But Dean is addicted. He doesn't stop.

Then he gets Sam back and he has to hide it. His shaved legs, all the girly clothes he has collected. And it's hard to part with this part of him but he does. Because he can't have Sam leave him again. He wouldn't survive that.

So the clothes get tossed aside. He stops shaving. He even stops wearing lingerie. It's not safe with Sam there.

Then, many years later, in the safety of the bunker, Dean tries on the lingerie again. It's easier to hide now that they have a whole hideout as their home base. Sam doesn't notice.

Until Dean messes up on a hunt and Sam has to undress him and he SEES and Dean wants to find a hole and crawl and never come back.

Sam would have teased him if he hadn't already seen the lingerie collection in the bottom of Dean's closet, if he hadn't found the makeup supplies in the back of the bathroom cabinet, if he hadn't seen Dean stare at shops with female clothing with fire in his eyes.

"Dude, we've saved the world how many times now? I think you are entitled to wear whatever you want."

And Dean knows its genuine but he still feels disgusting doing something like this. He doesn't buy clothes still.

Not until Sam shows up with a red dress that has Dean pretty much salivating and practically forcing Dean in it.

Dean cries because it's been so long.

Sam keeps buying him clothes and slowly Dean is back on his routine.

It doesn't stop at shaving his legs this time though.

He lets his hair grow out. It gets longer than Sam's and it looks so good with his new clothes.

So it might have taken him some years, but Dean is finally letting himself dress as he wants, all thanks to Sammy's support.

[boywifesammy]

imagine repressed & closeted transfem dean who never figures it out. imagine the sheer amount of guilt, fear, self-hatred and disgust he’d feel at what he is. big, clunky, dangerous. he takes comfort in his power, but it makes him feel sick. when he looks into the mirror and sees his hard edges, his body feels like it’s trying to rip open from the inside, yet he has no idea why.

dean plays his father’s wife until he dies. he takes care of sam and raises him as if he’s his own son. he’s a housewife in everything but reality. he desperately wants family, desperately wants to nurture, but his body isn’t built for that.

he’s taught by john and the world that he has to be strong. he has to be a man. he can never show emotion, because it’ll only be a weakness, and weakness is deadly. dean can never have a family because his body is wrong and he can never love like a woman because he cannot be weak.

so dean holds tight to those little moments of female connection with sam and his father like a dirty secret. he lays in bed at night and pretends he doesn’t think about being softer and lovelier. he stares at himself in motel mirrors until it makes him sick. he builds muscle and crops his hair short because this thing inside of him terrifies the hell out of him and he has to do anything to keep it at bay.

women comment on his looks a lot. when he’s young, they call him pretty, beautiful, gorgeous. they compliment his soft green eyes and plush lips and spattering of freckles. secretly, dean loves it. it makes that thing inside of him flare up in joy, which is why he knows that this is dangerous, and not something to be indulged. he stays up at night obsessing. shaves every morning and runs his fingers over his soft cheeks, flutters his long eye lashes, tries to find the soft edges of his cheekbones.

this thing is slowly eating away at him. the closer he gets to it the more volatile he feels. he jerks off under the blankets with a hand over his mouth to stifle the gasping, whimpery sounds he makes. the sound of his own voice scares him. his throat chokes up when a guy hits on him and john gives him a glare. one time he puts a finger up his ass and comes so hard that he sees stars, not because of the stimulation, but just from the idea of being wet and slick and pliant between his legs.

dean loves women and it makes him feel sick to the very core. he wishes that he loved women in a normal way. instead, he sees their curvy bodies and an awful, disgusting mixture of greed-lust-jealousy rocks through him. it’s all a strange, roundabout way of wrecking himself, because it’s extremely easy to play the role they want him to play, but god if it doesn’t hurt like hell.

dean loves fucking women. he’s desperate in bed but he’s always sure to be gentle with his thrusts. it makes him feel less disgusting. he likes shoving his face into a chick’s pussy, eating her out until she’s dripping, or nuzzling into the crook of her neck as he fucks her wet cunt. he likes listening to their gasping whines and moans. the feeling of it all makes his teeth clench with guilt; her cunt on his dick, his strong thighs, the way she keeps moaning his name. but it’s so easy to pretend in moments like these.

dean puts his face into her hair, and smells her citrus shampoo as she wails out cries. he doesn’t imagine being her, but he focuses on her noises, on the softness of her body and the wetness of her pussy. he always cums silently, his entire body quivering and shaking, because he’s too scared of the noise that’d come out of his mouth if he opened it.

when rhonda hurley makes him wear her panties, he nearly throws up on her carpet from how hard his heart is beating. they’re silky on his dick. rhonda calls him pretty, beautiful, she strokes at his flaccid penis through the panties and kisses messy lines up his belly. dean is hard and shivering by the end of her teasing, leaking through the panties and flushed from head to toe.

rhonda is both the best fuck that dean ever has and his worst fears coming to life. she calls him good girl as he fucks her. it ends embarrassingly early. when dean cums, it’s with a gasping cry of her name and a girly little keen that haunts his nightmares. he doesn’t remember ever cumming so hard in his life. he shook with aftershocks for minutes after, dazed and disgusted with himself.

rhonda gives dean her number. he never calls her back. after dean leaves that town, he burns the panties and stops shaving his stubble so short. memories of rhonda make him angry. he sinks into hunting and drinks until he’s cross-eyed. dean takes solace in the horror of violence. he bathes himself in that disgust and he feels right at home in the middle of it.

sometimes, dean can’t sleep at night from how sick he feels. he tries to figure out why, but he can’t place the reason. it eats him up inside. makes him feel like a monster. he thinks that he may just be a disgusting freak of a man.

as dean gets older the comments about him getting pretty melt away. he knows he’s objectively extremely attractive, in a male model sort of way, but it doesn’t match up with the images in his head.

the thoughts get more and more humiliating as time goes on. he’s not a twink anymore and he can’t be fantasizing about being fem, but he can’t stop it. he stays up at night itching in his own skin, brutally aware that he’d look hideous and disgusting in anything girly. his body is too big and bulky. he’s a freak for being into that sort of thing.

dean eventually admits to himself that he might be a little gay. he keeps it on the dl, visits gay bars when they hit more liberal cities, and doesn’t ever repeat the same place. he likes being dressed up and bent over. he chalks it all up to a crossdressing fetish, and while that’s humiliating and sickening, it’s easier than having to deal with whatever it is that’s going on with him.

dean aches inside perpetually because he is flawed. he wants to hold his child in his arms and wear dresses and flirt shamelessly with men. he knows he’s a freak for it but he’s accepted that he’s going to perpetually live with this pain.

he gets older and older and the dysphoria gets so fucking bad that he can’t even look in the mirror anymore, but it doesn’t matter at this point. he’s completely disconnected himself from his body. he’s a sick, perverted freak in the body of a man and none of it feels right. he uses his body like a tool, a weapon, and he purposefully keeps it masculine and well-toned to push back any illusions that he’s anything but a man.

and sometimes, he’ll go to gay bars and let himself get railed to incoherence. he’ll drive three towns over while sam’s asleep and put on his makeup in an alleyway nearby. he always looks for men bigger than him. men who’ll call him pretty and beautiful and treat his ass like a cunt.

and if he’s lucky, maybe they’ll let some other words slip. maybe they’ll call him babygirl or darling or play with his pecs like tits as they pound him deep. and sometimes, if he’s really lucky, he’ll get to wear something pink and lacy. sheer panties. a bralet. stockings or a necklace.

he always cums in the first few minutes on those nights. he doesn’t mind being fucked until the other guy finishes, as long as he keeps calling him a good girl for taking it.

dean always throws up in the club bathroom afterwards. he spends hours wiping off all the makeup from his face and sleeps in the impala for the night. he gives himself another wipe the morning after and tells sam that he was out with a one night stand. it technically isn’t a lie.

one time, sam makes a joke about dean being a woman. he pushes. he calls him a pretty lady, and dean is horrified when his eyes wet a bit at it. he can’t take it. he starts the fight, but sam wins it. he pins dean down and starts to yell at him. then he sees that dean is crying. he isn’t making any noise or shaking, but his cheeks are wet.

don’t, is all he says. it hurts like hell to get out. sam seems confused, but he doesn’t question it. he doesn’t make the joke again. dean forgets about the whole thing and pretends he doesn’t feel the weird looks sam sends him sometimes.

dean dies like that, alone and angry, in a body that’s all hard edges and grief and hatred.

he’s the same in heaven. he can’t imagine being any other way. he doesn’t even know what he wants, what would make him happy. most days, he’s happy with driving his impala aimlessly, drinking while watching sunsets and tuning into the world around him. thinking, and thinking, and thinking. about rhonda hurley and her satin panties and his father and the soft, warm thing buried inside of him.

dean doesn’t know why he feels sick inside when he looks at himself, but he’s too broken to ever figure it out. the only thing that he knows is that he doesn’t feel guilt the same in heaven. that means that when he has those strange dreams of warm kisses, strong arms around his tiny waist, and the warm, beating heat of his child’s heart against his own pillowed chest, he can spend some time in bed in the morning trying to recollect the memories without hating himself for it.

[transchesters]

transfem dean. thoughts?

mixed feelings. i love transchesters in all forms but i think transfem dean has to be a very nuanced thing. because misogyny and toxic masculinity is like the crux of his whole thing. y’know? like i don’t think a transfem lens would fix her. i think it would damage her a lot. i think it would take her a long long time to come to terms with it. she’d hate herself a lot and be even worse to women in general. but i also think that it could be a very good thing for her. like way down the line probably. especially if sam is transfem too in this supposed AU. i just don’t like takes that try to make dean less of an awful man, and i think a transfem lens needs to be placed over her with care and timidness. i dunno if this even makes sense or not. i’m probably not the best person to speak on this also but i love @ardentpoop takes on transfem dean and dean in general tbh. let’s discuss in the notes tho i love to see all the takes!!

[ro-sham-no]

Transfemme dean your beloved, you say?

https://archiveofourown.org/works/55091809

- schizosamwinchester

"Dean had found some shred of himself in his father’s bed, but that Dean had died right along with him."

holy FUCK this is incredible. you've done it, you've captured The Thing.

i love the way you captured dean's internal conflict, especially about how other queer people see right through him (her?). i feel like being seen is one of dean's biggest fears, in general, but especially so for any sort of perception that shows him as weak or "less-than" in a way he doesn't intend.

that fear, to me, is a huge part of why he plays up the whole machismo act, just like you've written about here. he plays up the machismo-ness, but also his overall slob/player demeanor, which is just such a huge flag for "hate me about THIS, not that other thing that you definitely don't know about."

but i really, really love that he just can't fucking hide it. even sam sees it, "well, you are kind of butch. they probably think you're overcompensating." he is a queer, and just his existence, the composition of his skin, screams it out to every person he meets and i lovvve thattt

and then, in the end, having that identity be SO entwined with his dad and how he could be something like a woman but only in his father's bed, that when john dies, all dean has left is being john's eldest son, being sammy's older brother? so, so good!!

[davilishuuu]

When your brother finally kisses his angel and you have to deal with them doing it all the f time

[rivers-oc]

[willgrahamsleftear]

thinking of trans soulless sam. like she’s all instinctual reaction. which means she doesn’t CARE about the fact that she’s closeted and she’s not gonna conceal or be polite about her identity. about who she is.

Dean refers to her as his baby brother and she just snaps back “I’m a girl.” blank stare, maybe a little angry. and Dean is SO confused because Sam had never said anything like that before? and of course Sam continues to correct him, again and again, even more aggressively.

Dean is very quick to change his language when referring to her

and when Sam gets her soul back she’s just MORTIFIED because whatifdeanhatesher but no, he’s just even more overprotective now (if that’s even possible) because she’s his beautiful baby sister now and ohhhhh

ARGHHHH soulless sam I love you so much,,,

[angelarsenal]

OHHH when you get the time, could you maybe draw tgirl Sam again? She is so special to me :3

YESyes always have the time to draw her ....

w a splash of wincest tbh..

[kerryweaverlesbian]

When you're Dean Winchester and you're a masc manly man who shoots guns and drinks beers and doesn't listen to any of that anemic pop shit and your very soul is represented by your hot loud muscle car full of leather and guns. And she's a girl.

[thorsfavoritelesbian1]

gay son or thot daughter

[babyblue-mind]

genderbent winchesters (so trans masc dean and trans woman sam) wip!!! circa s1

they don’t have feet yet because i don’t really want to take reference photos of my feet in the office ❤️

[boywifesammy]

ftm!sam wincest genderbend fic where they get hit with a witch’s curse and dean gets massive bahonkers and a pussy and sam is just… the same. but with a dick.

and obviously they then proceed to fuck on every available surface, ft. sam’s gender euphoria & vague transfem dean genderfuck vibes where dean’s maybe a little too into this whole girl thing.

[transchesters]

meg notices something strange when she’s inside of sam.

sam, who is 6’4” and 220 pounds of muscle, who towers over everyone he meets. sam, who on the inside, is a battered and broken little girl. meg would know. she’s been a battered and broken little girl herself.

so maybe she feels a little sympathy. maybe, as she stares into hazel eyes at this massive body in the mirror, she wishes that sam would just give in to all of this. her demonic blood, her cursed existence. at least if she was a demon, she could choose her body! she could look like meg knows she wants to.

yes, there’s sympathy, but meg is a demon. so sympathy comes with a darkness, twisted and vile. she lets sam be present in her mind as she gazes at her, through her, into the mirror. she makes sam watch as she slowly unbuttons her flannel, revealing her toned chest, her defined abdomen.

“if you were like me, sammy, you could choose any body you wanted,” meg murmurs, her voice lowered since she’s speaking from sam. “you could even take the one i used when we met. that little blonde piece. i know you thought she was pretty. i could take this body, and you could take that one, and we could find your rightful place on the throne of hell.”

she grins as sam constricts and fights against her. “besides. i think queen of hell has a much nicer ring to it than king. the demons wouldn’t question you. they’d call you whatever you wanted. she, your majesty, your highness. wouldn’t that be nicer than what you get now?”

when sam thinks of dean, meg sees what she sees. her brother, in all his glory, and what he would look like if sam said yes. “oh, sammy… you think he would ever accept you?” meg laughs, a throaty sound. she’s not used to sounding so masculine, but she doesn’t hate it at all. “i mean, the demon blood is one thing. it happened when you were a baby, and he still blames you! how do you think he’ll react if you tell him you’re a girl? he’s not exactly an award-winning feminist.”

meg tuts softly, shaking her head. sam’s hair is shaggy and ruffles as meg moves. “he’ll just think you’re an even bigger freak. hell, he’d probably blame me! i mean, you’ve got a girl demon inside of you. that must leave a mark, right?”

—

when all is said and done, when meg is exorcized from his body, sam can’t help but wonder if she was right. here he is, back to thinking of himself as a man. as a younger brother and a son. as a hunter, cursed to live this life. this life where he can’t, by any means, be a girl. he knows what dean would say.

meg was right. sam keeps his thoughts to himself. he doesn’t have time to contemplate his gender. he’s suffered with this secret since he was sixteen, old enough to stare at his female classmates and wish for his body to be like theirs. he decides that he’ll suffer for the rest of his life. he was born a man, and he would die a man. his secret died with jessica, with brady, with all of his stanford friends he had come out to. they were the last, and only, ones to call him “she”.

sam will take it to the grave. he doesn’t need to give dean another reason to call him a freak.

[lochyard]

I love mixing my trans sam hc with wincest because for the past like 2 days I’ve been going mental thinking about how dean would love sam no matter what because deans love for sam isn’t defined by what sams gender is and is instead defined by his undying loyalty to sam,,

[davilishuuu]

Idk how to use this thing but I offer you some winchester siblings + transfem sam🏳️‍⚧️

[punkeropercyjackson]

'Female-coded' makes me loose my mind because when someone who's percieved as male gets mistreated in the way women do,that's transmisogyny.Transfeminism is when you're amab but female in gender but not allowed to be a woman yet still face the bad aspects of girlhood.Calling male characters 'female-coded' is literally just reinventing transmisogyny not only in rethoric but trying to make transmisogyny for cisgirls because y'all want extra oppression as you see it making you more of a woman.And y'all act like xenogender people are the losers doing made up stuff about gender that's stupid and childish