#crossdressing sam

[boywifesammy]

i am DESPERATELY looking for any late seasons crossdressing sam fics. looking specifically for a sam that’s been repressing his femininity for a long time and is embarassed/secretive about his cd because he sees himself as too masculine & hard to be fem. bonus points if he gets super euphoric about crossdressing during sex

ideally wincest or sam-centric but i’ll take anything really. pls. help a guy out here

[hedgeyart]

Was doodling Sam and Max at work the other day and taking outfit requests for Max. Somehow this one came out the best. 😂

[morelikesin]

Call me irresponsible

Yes, I'm unreliable

But it's undeniably true

That I'm irresponsibly mad for you

A reimagining of the piece below ❤️

[ghost-facess]

just thinking about sam wanting dean to call him feminine names. sam wanting to be called "pretty girl", "sweetie" and "baby girl".

+ questionable relationship! samdean where dean walks into sam's room and catches a glimpse of pastel pink lingerie, a bralette and a lacy thong, maybe some garters. sam hears his door creak open and jumps, quickly scrambling to grab the pieces of clothing and hide them from view, he turns to dean - “what the fuck dean?? get out!"” and rushes to slam the door. dean blinks as the door is quickly slammed in his face. dean chuckles quietly and shakes his head, his baby brother was into girly stuff? sam definitely didn't have a girlfriend, oh dean would know, so it's got to be for himself.

sure, they made out a couple of times, when sam came to dean when he was a mid-teen, embarrassingly telling his brother that he didn't know how to make out but of course his older brother who's had plenty of short-lived relationships with girls knew how to kiss. dean watched sam's blush grow on his cheeks and thought this was the perfect time to take advantage of sam's innocence.

“sure sammy, come here.” dean says as he reaches out to cup his brother's face and slightly stroke his face. trusting his brother and being oblivious to the taboo situation, he waits as dean leans in and presses his lips to sam's plush ones. sam closes his eyes and moments pass before dean pulls away. dean tells sam to open his mouth before dean moves back in and slips his tongue in. sam cringes and pushes dean away - “ugh, that feels weird, your tongue's all slimy and it's moving all around!”

a few weeks after walking in on sam and his questionable underwear, he sees him actually wearing it this time. “come on sam! hurry up! i'm about to piss myself here!” dean bangs heavily on the bathroom door. dean just thinks sam's taking his time on the toilet, but really he's modelling his new lingerie set. he's looking in the long mirror above the sink, admiring the bralette hugs his chest perfectly, and how the thong draws attention to his ass, lace covering half his cheeks.

“just a minute!” sam yells, annoyed about his interruption but dean isn't having it. “nope! i'm coming in.” “no, dean wait-”

dean opens the door with an annoyed look on his face, pissed off and about to say something, but nothing comes out. he stares at his brother who is just as shocked as him wearing something that a man definitely shouldn't be wearing. before he can stop himself, dean's eyes drift down his brother's body, nipples thinly veiled by the satin triangle material, abs flexed, v-line and bulge in the tiny thong.

none of them speak.

[babyboywinchester]

https://www.tumblr.com/sunbleachedf4wn/763003570311266304/jared-what-about-say-yes-to-the-dress-jensen

hey have you seen this? 👀 dean is horny for sam in a dress confirmed.

Link.

It would be a short episode because that dress would be off in like 5 seconds. I do love me some pretty Sam and adoring/horny Dean.

[morelikesin]

🐶 Y'know, I fall in love with you all over again when we go on dates like this, Max.

🐰 You're getting a pass for that awful pun because you're the prettiest thing this side a' the world, Sam.

🐶 What can I say? I'm as corny as Kansas in August.

🐰 And as normal as blueberry pie.

[impalafullofbees]

Just discovered Weirdcest, this is my contribution! (Sammy lost a bet)

If anyone has any suggestions what I should draw next, that would be great cause I love wincest but don’t have any ideas of what I could draw.

[jkontumblr]

JMark Lopez Sam

[boybasher]

Hard Head 🥀 (my behind the scenes vlog and soft goth lifestyle movie)

[cosmic-kinglet]

So, a certain person's suggestion may or may not have led to me making a pinterest board of casual outfits for each of the T.O.P. boys...with some of the stuff in Eclipse's section being more traditionally feminine outfits. 👀

[ghost-facess]

tell us more about dean feminizing sam while they both get off on it ?

HELLO!

Thank you for this ask!

I honestly haven't wrote anything properly in like 3 years so please bear with me. also I'm new to the fandom so I'm slowly learning their dynamics.

what comes to mind is that sam eventually confides in dean about his kink/fetish(?) and of course, dean is totally open to it which causes sam to be relieved.

while dean is out shopping, he comes across a lingerie shop and you know he's gotta go in. the shop assistant politely greets him, “hello, shopping for your girlfriend?” dean frowns a bit as he isn't comfortable telling the girl that it's actually in fact for a man, but he goes with it anyway.

“yeah, she's into pastel bras and uh, stuff like that.” he coughs and clears his throat.

“sure sir, right this way.” she beams and directs him. it's a big shop and she lets him browse in private. dean strolls, taking in the displays and finds a cute matching pair of a light blue plunge bra and brazillian panties. plunge will show off his chest well, he thought.

while dean would LOVE to spend all his money on sammy, he's got to be realistic and be ready to take the clothes back if it isn't sam's taste.

still, while he's there he can't help himself but take a look at the costume section and his eyes come across one of those sexy schoolgirl outfits. he tries to ignore the shame come across as he picks up a medium and takes both to the counter.

back at home, dean plonks the gift bag on the bed next to where sam is sitting and demands he try it on, trying to stay cool but in truth, he's quite excited. sam gives him a questionable look but rummages in the bag and pulls both sets out, with a little smile. sam looks up to dean with a grin and takes the costume set with him into the bathroom.

during their make-out session, dean is lying on his back, head between the two pillows as sam sets his arms on dean's bare chest, hips rolling onto dean's clothed crotch.

“shit..... sammy.” groans fall from dean's mouth as he looks over his brother with hooded eyes. “you look like such a slut in this.... reminds me of my high school days when I'd make 'em dress up.” sam's bangs are wet and stuck to his forehead, nipples hard and visible thin shirt, pleated skirt not reaching past his mid-thigh.

dean gives his brother's ass a harsh slap. “speed up the pace, you're like a virgin.” sam growls at this and now starts to harshly grind down, grabbing the other's short hair in protest. “shut up you fucker.” he moans out.

“yeahh... baby girl, just like that. just like that.”

[deeranger]

Oh, such a pretty thing 😍

[coupleofdays]

Some of you may have heard of the "programming socks" meme, the basic joke being that crossdressing makes you a better computer programmer. I, of course, began to wonder what Kevin Flynn would make of it. I think that at first, he would just find it funny. But in the back of his head, he begins to wonder if there might actually be something to it. So one evening Alan walks into Flynn's office and sees him working late at the computer, tapping the keyboard intensely, wearing knee-high socks and a cute skirt. Flynn enthusiastically tells him that he doesn't know exactly why, but for some reason these new clothes gets him really focused when programming. He suggests that Alan should try it as well ("maybe you could borrow some of Lora's stuff"). Alan politely declines, and chalks the whole thing up as another one of Flynn's tech guru excentricities (Lora later tells him that she agrees with Flynn, she always gets her best work done while wearing a skirt. Alan still declines the offer to try).

Later, Kevin shows up on the Grid in a full Sailor Scout outfit, feeling that it really makes his User powers stronger than ever before. Tron and Clu are a little surprised by the new look, but they just figure it's some kind of typical User fashion they haven't seen before. And they can't argue with the results. Clu might even consider trying wearing something similar, if it could make him more efficient. Tron politely declines Flynn's offer to try it.

Much later, when Sam find Kevin in his hideout, the elder Flynn is wearing a rather fetching dress with matching accesories, and tells him that it really helps him focus on his zen thing for some reason. Sam is somewhat taken aback at first, but figures that his dad has just been stuck on the Grid for too long and has gone a little loopy. He politely declines Kevin's offer to try it himself (even when Quorra agrees with Kevin that Sam would look good in high heels).

[morelikesin]

An idea I had for a few months and decided to complete in time for the 36th anniversary of Who Framed Roger Rabbit 🐰👠

Transcript for the second image below the cut!

🐶 "What do you think? It was a tight fit but it don't look half bad! You know your opinion is the only one I care about. Speaking of which, you look darling, darlin'. Fits you well! Hey, Max, you're doing that thing where you space out - you okay? Earth to Max? You got a fever or somethin'?"

[deeranger]

YES

sam in a skirt but not a short hottie one he'd probably like something kinda long and boho

[loving-family-poll]

Ultimate Incest Tournament - Final

Propaganda under the cut:

Sam/Dean:

I'm sorry but they have it all. children of metaphorical incest just continuing the cycle in any way they can. they are brothers and mother + son and wives and each other's scorned lovers and life partners they've had multiple infidelity arcs they are sexually psychopathic together they have forsook life and morality and the earth itself for each other and just love each other so much . They are literally in a heaven of their own making together for eternity, incestuously. Come on!!! Blueprint!!!!! It's not gay if he's your brother!!!!!

dean did stuff to sam's dead body in ahbl. i just know it

Messed-up, isolated sibs with all the daddy and abandonment issues. Their lives are so claustrophobic with the brothers no more than five feet apart in the car, a motel room, or standing next to civilians (face it, they are frigging magnets). Can't leave out that they are always touching each other to check for wounds which is a huge PLUS for any shipper.

Sam and Dean ARE literally the blowjob brothers. They walk into a situation and everyone goes well well well if it isn't the blowjob brothers....... And they say. Yep. That's us. And then they fix the situation with their epic love story

THE classic, iconic, show shopping, never done before etc. etc. incest ship. It changed fandom and it changed the world

Cersei/Jaime:

they're literally womb-to-tomb lovers. they feel that the rest of the world is beneath them and they're the only ones that matter. the fact that they're twins is fundamental to their attraction to each other

they’re blonde they’re evil they crossdress they’re fucked-up mirrors of one another they serve cunt they’re both bisexual probably and they’re TWINS who FUCK. who said that.

"if I were a woman, I'd be Cersei."

"I'll kill [...] the whole bloody lot of them until you and I are the only people left in this world."

"I am sick of being careful. The Targaryens wed brother to sister, why shouldn't we do the same? Marry me, Cersei. Stand up before the realm and say it's me you want."

"'Do you have a little wife, ser?'" No, I have a sister."