#ftm!sam winchester

[l1tw1ck]

In Exchange

Sub!Bottom!FTM Sam Winchester x Dom!Top!Male Reader

☆ Word Count: 3,617 ☆

AFAB Language Used

blacked out every time i wrote this like jekyll and hyde 😭 /j

CW: Non-Con, Sexual Coercion, Drugging, Blowjob, Cum Swallowing, Creampie, Pregnancy Mention, Masturbation, Cunnilingus, Puppy Play (Collar, Puppy Sam), Nipple Sucking, Riding, Corruption

“Excuse me, are you [Name]?” Sam walks up to you as you're smoking outside a bar.

“What's it to you?”

“I’m Joseph Johnson. I'm a detective.” Sam shows you his badge just long enough for you to believe him. “I’d like to ask you some questions about the recent incident.”

“Then you’d better give up and ask someone else.”

Sam looks at you in dismay. “You're the only living witness, we won't be able to get anywhere without you!”

“I’m not sharing anything without something in return.”

He perks up. “I've got about 60 buc-”

“I'm not looking for money. I want you to get on your knees and give me a blowjob.”

He looks at you in shock. “Are you serious?”

“Completely. Make your choice, Sherlock.”

There is no choice. He needs this information in order to save the town. He has to do it. “Fine…Just don't make me swallow.”

You stub out your cigarette. “You're not in a position to make demands, sweetheart. You're gonna swallow it if you want me to talk.”

Chills run down his spine. You're so assertive, it's…..sexy. He almost slaps himself. He lets out a big sigh. “Okay.”

You smile. “Hold on.” You enter the bar and come out a few minutes later with a bottle of beer. It's already been opened. That makes Sam suspicious but in your defense, he doesn't have a bottle opener on him. Against his better judgment, he chugs the bottle.

He notices the chilling grin on your face but hopes it's not because you drugged him. You lead him to a secluded alleyway. “Kneel.” You unbuckle your belt.

“Here? Are you serious?”

“Didn't you hear me, pretty boy? Kneel.”

Sam frowns and gets down on his knees. He gulps upon seeing your hard cock. He’s never seen one in real life before, after all, he's never gone far enough for that.

“Open wide.” You tug on his hair. He looks at you with contempt but opens his mouth anyways. The feeling of your cock entering his mouth is completely foreign. It's way different than sucking on a popsicle or some other iced treat. It’s warm and pulsing. And it's thick, so thick his jaw hurts. “As I thought, you look much better with my cock stuffed in your mouth.”

Sam shivers. He can't believe that turned him on. His body suddenly begins to rise in temperature, as if he's come down with a fever. You don't seem to care about his reddening face as you slowly drag him back and forth on your cock. He stops worrying about it, even as he starts to feel more aroused than he should. He just closes his eyes and discreetly ruts against his hand as you do all the work for him. He feels so wet that his slick is probably bleeding through his underwear. He desperately needs to touch himself but he's sober enough to feel embarrassed about doing so. It's so hard for him to feel pleasure through his pants that he's started whimpering. You don't know why he's doing that but you're not complaining about the new sensation you're feeling.

“Shit- I’m already gonna come-” You moan. “Your mouth is amazing, sweetheart, you're better off selling it than being a detective.”

Sam moans as you come in his mouth. His mind is so hazy and high on whatever you drugged him with that he actually feels happy to swallow your seed. He’s completely out of his mind.

You pull him away from your cock and pry open his mouth with your thumb to make sure he's swallowed everything. “Good boy.”

He looks at you almost demurely.

“It’d be a shame to stop here, don't you think?” You run your fingers through his hair. The drug seems to have kicked in completely so you know he’ll agree.

“Mhm..”

“It’d be nice if I could fuck that sweet ass of yours...”

“Not there...” He shakes his head.

“Why not? I’d make you feel real good.”

“Isn't my pussy better?” Sam smiles, unbuckling his belt.

“It definitely is.” You smirk.

Sam shakily gets up on his feet and drops his pants and boxers to his ankles. He walks over to the wall and bends over, giving you a drunken smile. You look at his pussy and feel your cock immediately come back to life. He's so wet that his slick is on the inner corner of his thighs. You can't wait to dive into that.

You stick two of your fingers inside him, not caring for how that makes him feel, and explore his insides. He's soft, warm, and oh so fucking wet. Sam moans, too drugged to consider the fact that he's in public.

“Th- there!” His voice and legs are shaking. “Yes-yes-yes–”

“Already gonna come, darling?” You find his g-spot and immediately cause him to squirt. You watch in awe, painfully hard thanks to this mesmerizing display. You pull your fingers out and slowly inch your cock inside him. “Sorry, I just couldn't wait any longer. You don't mind, right, baby?”

Sam moans, eyes half lidded. “Mm- deeper~”

“The drug’s really changed you…or maybe it's just allowed your real personality to show?” You smirk, going deeper as he requested. “I might have to keep drugging you if it means I can fuck this sweet pussy of yours.”

He shivers, leaning further against the wall as you make him experience his pussy stretching to accommodate your girth for the first time. “Bi- big~” He bites his lip, absolutely blissed out.

“You like how big I am? Or how good your cunt feels stretching to fit me?”

“Ye- yes~ so good~” He answers both of your questions. “My pussy feels so good, [Name]~”

“Yeah? I’ll make it feel even better.” Once you bottom out you start fucking him at a rough pace. The warm and slippery feeling of his cunt is making you too aroused to control yourself. You cover Sam’s mouth with your hand, knowing he won't even try to keep quiet. Your hand quickly becomes drenched with his saliva, a constant vibration thanks to Sam moaning. You can still hear his moans, albeit muffled, but at a much better level that suits your location. “You're such a good boy, you know? Taking my cock so fucking well. If we were at my place, I’d be happy to hear you moan.”

Sam’s body reacts to being called a good boy, his cunt clenching around you once again.

“I wish I could have you, a cute puppy like you should have an owner. Although, I don't know if I have the strength to actually let you go.” You pull down the collar from the back of his shirt and bite him, making a mark that’s sure to last a while. You can tell just by hearing him and feeling the way his cunt reacts that he liked that. “How about you touch yourself for me, pup? I want you to feel extra good.”

Sam brings his hand down to his t-dick, gently stroking himself and accelerating the amount of time it’ll take him to have an orgasm.

“Look at you, following orders so well.”

He whimpers in response.

“You’d be better off belonging to me than some agency, don't you think?” You move your hand away from his mouth.

“Ye- yes- wanna be yours!” He moans, squirting again on your cock. In his current state of mind, he feels overjoyed at the idea of abandoning his dangerous “career” for a life full of pleasure and submission. He won't have to think or put his life on the line anymore. Right now, he doesn't have the ability to think rationally and being your dog is all he wants. “Tak- take me! I wanna be your puppy~!”

You bury your head in his shoulder, slowing down. “I’ll hold you to that. Gonna make sure you can't change your mind and leave me.” You come inside of him despite knowing he wouldn't want this if he was sober. At this point you don't care what he thinks, you just want him. Maybe the whiskey you had earlier is finally getting to you...

Sam wakes up on his motel bed, feeling something inside his underwear, a painful feeling in his neck, and a sharp headache. He closes his eyes and tries to recall what happened last night. He soon starts to remember everything, even after the drug kicked in. He should be angry but he isn't. He's horny. He sits up on the bed and looks around.

“Dean?” He calls out. No response. He leans back and brings his hand into his pants, sliding his index and middle finger down his slick cunt. He feels your cum and pushes it back inside him, fingering himself with your cum. He doesn't want to get pregnant but he can't help himself. Just doing this makes him so horny…He feels like a perv.

Sam leans back and moans, feeling extra sensitive. He remembers how you made him squirt for the first time and how it’d probably feel even more amazing if he could do it sober. He starts to think about all the compliments you gave him and how you wanted to make him yours. He knows he should be focusing on hunting, especially because of his powers, but he can't help but yearn for a safe life with you. He doesn't even really know you. He did a background check on you but he didn't look at anything that would’ve given him any information about your personality. He can't believe that a one night with you is making him feel like this. Making him want to relinquish his autonomy to a stranger.

He murmurs your name, absolutely enamored with you. Are you even human? You have to have some special power to make him so infatuated with you. Right?

Before he can reach his climax, the sound of the doorknob twisting stops him. Sam quickly takes out his hand and rubs it on his clothes. Dean opens up the door and immediately looks at Sam.

“Where the hell were you last night? And why are you in the same clothes?”

“I- I uh…got drunk.” He looks at him sheepishly.

“Why?!”

“[Name] didn't want to talk unless I won a drinking game…I won.”

Dean looks surprised. “That guy must be even more of a lightweight than you are.”

Sam laughs awkwardly.

“So what's the story?”

“I don't know–” Sam stops thanks to Dean’s expression. “Yet! I’ll call him today.”

“You got his number?”

Sam vaguely remembers you putting something in his pocket. He digs into his right pocket and pulls out a piece of paper. He opens it up. I’ll talk. I left you hangover medicine, the morning after pill, and a pregnancy test. Let me know the results when the time comes. [Your Number]. “Yeah. I got it.” He turns to the bedside table and sees a bag with the logo from the local pharmacy. His heart flutters from your consideration. Which is ironic, considering what you did to him.

“Good. Take a shower and eat something, then call him.” Dean grabs the remote, gets onto his bed, and turns on the tv.

At around 11, Sam called you and now you're sitting outside a café with “Joseph” and his partner, “Francis”.

“There's two of you.” You raise your eyebrow. “Looks like you're not Sherlock, but one of the hardy boys.” You chuckle.

Sam laughs awkwardly. “This is my partner–”

“Wait, let me guess, Frank?”

“Francis. My friends call me Frank.” He smiles, impressed that you got the reference.

“Joseph and Franics. Interesting coincidence.” You’re tempted to inquire further but you decide not to. You're not too excited to recount the story but you’d rather just get it over with.

“And that was it.” You lean back into the chair. You noticed Sam was staring at you the entire time but you ignored it, you don't want to bring anything up with Dean around.

“Thanks for telling us. We’ll get to the bottom of this.” Dean stands up and shakes your hand. “Alright, let's go.” He turns to Sam.

“I- I actually have something to do, go without me.”

“What? What the hell could be so important?”

Sam looks away and doesn't answer.

Dean sighs heavily. “Fine. But don't let me find out you're trying to meet some girl or something.” He shakes his head and walks over to his car.

“So, what’s more important than your investigation?” You tilt your head in interest.

“I remember what happened last night.”

“I sure hope so, that's the whole reason I’m here.”

“No, I remember that you drugged me.”

You’re a little surprised, that wasn't supposed to happen. You know he won't turn you in though. You’re sure of it. “Are ya gonna turn me in, Mr. Hardy?” You smile teasingly.

“Not if you do something for me in return. It's only fair, right?”

You give him an amused look. “Of course, puppy, it's only fair.”

Sam blushes at the name.

“So what do you want me to do?”

“Drive me to your place and you'll find out.”

“Alright, we'll have to make a quick stop though.” You grin and lead him to your car.

Sam enters your home, anxious for two reasons. One, because you went to a sex shop and told him what you bought is a secret. And two, because he's about to request something that nobody in their right mind would do after being taken advantage of in such a way.

He sits on your bed and watches you as you place the bag on your desk and reveal what you bought. A collar that closely resembles one for a dog, but clearly made to be worn by a human. Sam’s entire body heats up.

“Just a little something to remember me by.” You hand him the collar

He frowns slightly, he doesn't want to leave you. He doesn't know why he's so obsessed with you but he brushes away the thought and puts the collar on. He looks adorable. “Now you have to do my request.” He unbuckles his belt and unzips his pants. “I want you to eat me out.” He's been fantasizing about this in the shower. He can't leave this town without experiencing this at least once.

You lick your lips. “That's it? If that's what you want, I’ll be glad to do it.” You pull his pants and underwear off for him and kneel in between his legs. You slowly drag your tongue up his pussy, tasting him for the first time. You let out a soft noise of pleasure before wrapping your lips around his t-dick and slowly easing two your fingers into his cunt. Sam throws his head back and moans unabashedly as you suck him off, his body heating up. This is so much better than just fingering himself. Your mouth feels so good.

“Like that- yes~” Sam rolls his eyes back. It won't take long for him to come. “[Name]~!” He gasps when your fingers reach his g-spot. “Oh my God–” He falls back onto the bed, quickly climbing towards his orgasm. You add a third finger and continue to finger his wetness while sucking his cock more passionately. Sam can't even manage to get any words out, he feels too fucking good to even think about anything. He instinctively wraps his legs around your head and squirts, drenching you. He takes a few moments before letting go of you.

You pull away and lick your lips. “Now, how about a round two?”

Sam nods, removing his clothes. “I wanna ride you.”

“I’d love that.”

Sam hovers above your hard length, his left hand holding it in his place and his right on your shoulder. He lowers himself onto your cock, gasping when he feels you stretching him open. Despite his memory being mostly clear from that night, the pleasure he remembered wasn't enough to prepare him for this. “Fuck–!” He moans, continuing to lower himself down. Tears run down his cheeks thanks to the painful pleasure he's experiencing. “You're- so, so big-” He's breathless.

“You're adorable, puppy.” You hold his cheek in your hand. “I know you can handle it though, keep going.”

Sam moves further down until you're completely inside him. He looks at you, tears still streaming down.

“Good boy.” You kiss him. His eyes widen for a moment before closing his eyes and reciprocating the kiss. You briefly pull away to open your mouth and Sam is quick to catch on. You return to kissing him but now with your tongue. Sam considers himself a master at kissing, since it's the most he’s ever done. At least when it comes to receiving.

Sam finds himself grinding down on your cock, finding pleasure in the way you feel inside him.

You pull away from him and move down to his neck to bite and kiss it. You now move even further and wrap your lips around his nipple, happily sucking on it while your hand goes to massage his other breast. Sam whimpers and squeezes your cock happily. He could get used to this. Just being a dumb, slutty puppy for you to use sounds great to him. Sorry Dean and the greater good, Sam is giving up on being a hunter and choosing to become a simple toy.

You reluctantly leave his breasts and look at Sam with a smile. “Why don't you try riding me now?”

“Okay..” Sam places both his hands on your shoulders and slowly rises. He whimpers at the feeling. He never had the confidence to try using a dildo so he had no idea how intense this would feel. He quickly lowers himself, missing the feeling of your entire cock inside him. Even losing a few inches is upsetting for him.

“You don't want to do it anymore? Is it too hard for you, puppy?”

He looks away from you. “I want all of you inside me…”

“Aw, you can't even stand a few seconds? I promise you won't even feel it as long as you keep up a fast pace. It’ll feel much better than just having me inside you…although I do enjoy having you keep my cock warm.”

Sam tries riding you properly but he's still feeling weak and can't do it fast enough. He stops and looks at you.

“Let me help you.” You grab his waist and lift him up and down at a fast pace. Sam rolls his head back and moans in pleasure. “See? It feels good.”

“So- so good!” He cries. He feels so good that he barely even feels the painful slapping of his breasts against his chest. He can't even focus his sight, pain is nearly obsolete to him. He brings his hand down to his dick, stroking it as best he can. You can tell he's about to come.

“Come on, puppy, come for me.” You smirk. It doesn't take much longer after that for Sam to come. He squirts, making a mess on your body. “Good boy. Now it's my turn.”

Sam gasps as his body is suddenly pushed onto the bed, your hands squeezing his wrists tightly. “Just a little more, I know you can take it.” You roughly thrust into his cunt, indulging in the lovely wet warmth of his pussy. Sam doesn't mind, on the contrary, he’s happy to be used just to get you off. “You're so obedient, sweetheart, so perfect.” You start to act more like a dog than Sam, your horniness compelling you to rut into him like a wild beast. He can barely handle it thanks to the previous activities but he's fighting to stay awake. Seeing you in this state is much too arousing to miss.

“Tha- thank you~” He smiles stupidly.

Just hearing him say that with an expression like that makes you come. You briefly grip his wrists harder then loosen it as you come down from your high. “I don't want to let you go..”

“Me neither…I like being your puppy.” His eyelids start to feel heavy. “Wanna keep getting used…” He falls asleep. You kiss his forehead and pull out. You've never given an unconscious person a bath but it shouldn't be too hard.

Dean pounds angrily on your front door, a gun in his pocket ready to shoot you if necessary. Thanks to an eyewitness report from the café employee, he found out where Sam went. He doesn't know what's going on but he's furious. He hasn't answered his calls and he hasn't seen him since yesterday.

You open the door. “Ah! Francis. Here to pick up your partner?” You pause.

“What the fuck did you do to my brother?”

“Nothing he didn't like.” You reply plainly. “He's perfectly fine and drinking some tea. I’ll show you.”

Dean looks at Sam in shock. He's just wearing a big shirt and probably underwear. “Sam! What's going on?”

“I’m sorry, but I want to stay here. I love [Name] and I don't want to leave him.”

“WHAT?!” He's completely taken aback.

“You heard him. You’ll have to head back on your own. I’ll get his stuff for him.”

Dean doesn't trust you at all. He's going to be doing a lot of research on whatever monster you might be. He's convinced you're not human. “I’m staying longer. You probably did something to him…I don't trust you.”

“That's fine.” You smile. You have something else to worry about. “So…who's Sam?”

Sam and Dean both look at each other. Looks like they're going to have to reveal the truth, at least partially...

[your-unfriendlyghost]

how the pilot of supernatural probably went idk

context: Dean arrived at Stanford to see that Sam's transitioned. He's ftm in my head but you can interpret it however lol

Yup 100% how it went on the drive to California. i think.

[forcemasc-ed]

[boywifesammy]

sam winchester would NOT have a binder… he binds with ace bandages and packs with socks 👍

[vampyreblogger]

as a trans man i was worried that growing my hair out would make people think i was detransitioning but i just had one of the most validating interactions in my entire life

me: wow my hair's getting quite long now

my mum: yes... it's almost at sam winchester length

me: haha yes i suppose

my mum: or even... gerard way

[fizzy-dizzie]

Okay I'm only up to season 2 but that doesn't mean I don't see the light.

Gay fuck. Look at this little gayass. What the fuck, honestly like what a transgender. What a transgender fuck, a little transgender trans tranger.

Have you ever seen more of a trans man?? Like be fr a transgender male is right in front of you and he is not more trans then this little shit right here.

Gay people everywhere in this show honestly it's like a goddamn disease. The PRIDE disease, damn I fucking love gay people. The little slurs.

TRANSGENDER MALE GETS TOP SURGERY (GONE RIGHT) HE BECOMES COMFORTABLE IN SELF (CRAZY)

Could one say 'silly goose'? Would that be out of the question? Would that be so crazy??

[supernaturalscribe67]

Against the Grain

Words: 3,059

POV: 3rd Person

Pairing: Dean Winchester x Trans!FTM!Winchester!Reader [Platonic]

Warning(s): Fluff, Language (?), a brief mention of blood

Summary: Ever since the reader has come out to his brothers has transgender, they have been nothing but supportive. The only thing that Dean hasn't been supportive of is the reader's inconsistent facial hair growth. So, Dean comes up with a way to help him by teaching him how to shave.

A/N: I've officially hit over 30,000 words on my blog and I honestly have no idea how to feel about it...Feedback is greatly appreciated! Much love!

~.~.~.~.~.~.~.~.~.~.~.~.~.~.~.~.~.~.~.~.~.~.~.~.~.~.~.~.~.~.~.~.~.~.~.~.~.~.~.~.~.~.

Are suits always so itchy?

Granted, he didn’t know if he would feel the same if they had gotten his outfit from a retailer that specialized in men’s formalwear instead of the old Goodwill a couple of towns over, but they needed something quick and easy. It didn’t help that he wasn’t able to wash it between cases either, but he was thankful nonetheless. Sam and Dean had promised that they would take him to get fitted for a professional suit on their way back to the bunker. 

James Garrison would kindly pay, of course. 

When (Y/N) came out to his brothers as transgender, he didn’t know what kind of reaction he was expecting from them. All of the negativity that was brought upon them from early childhood had clouded his judgment on how they would respond to such dramatic news. He had kept it a secret from them for about three years as a result of the anxiety, already having trouble coming to terms with his new self-discovery. Alas, two years ago, when he had gathered up all of his courage and sat his brothers down to explain in grave detail what was going on inside of his head, they were nothing but supportive. 

It was an adjustment at first, with Dean having the hardest time with getting pronouns correct and slipping up on the name change, but (Y/N) could tell that he was doing his best, and that was all that mattered. He got better after a couple of months and had abandoned (Y/N)’s deadname and old pronouns completely in favor of his newly updated ones. (Y/N) could tell that Dean was proud of himself, and he was proud of him too. Sam, being the nerd that he is, wanted to learn more about transgenderism. He would ask his brother questions and scour the endless medical journals available online if (Y/N) couldn’t answer the ones that he had. He even went as far as to help (Y/N) find the perfect binder and get him set up with an appointment to start testosterone. Thanks to Sam, (Y/N) had been on testosterone for almost a year-and-a-half. 

With the use of testosterone came changes, changes that he wasn’t necessarily expecting. He was constantly starving, constantly horny, and hair was growing everywhere on his body. Everywhere. Even though he didn’t mind the hair growth in some places, one place that the hair seemed to be lacking in growth was on his face, the place where he had wanted it to grow the most. He had a couple of scraggly pieces here and there, most of the hair growth being on his sideburns and underneath his chin, none of the patches consistent in length. Still, every time he looked in the mirror, he couldn’t help but smile. He had finally started to feel like his true self. Like he was starting to morph into the person he was destined to be.

And he couldn’t be happier. 

(Y/N) emerged from the poorly lit motel bathroom, combing the sides of his hair with his fingertips. Sam and Dean stood in the center of the room, clad in their mock FBI uniforms. When they heard (Y/N) exit the bathroom, they turned their attention to him. It was the first time that he felt confident enough to dress as an agent on a case, and he was a little uncertain about his appearance. He wanted to make sure he looked professional enough to pass. It was a big change compared to when he only had to wear a blouse and pencil skirt. He didn’t miss those days. 

With his arms held out in a grandiose gesture, he gave a small smile. “What do you think? Do I look okay?” He asked with a tone that indicated his uncertainty. 

Sam and Dean eyed him, their gaze scanning from the top of his head to his shoes. Sam nodded. 

“Yeah, you look great,” he commented, a smirk curled up in the corner of his lips. 

Dean, on the other hand, furrowed his brows. “You look like a douchebag.” 

Sam slapped Dean’s shoulder. “Dude,” he hissed. 

“What?” He held his hands up. 

(Y/N) frowned and looked down at himself. “Why do I look like a douchebag?” He asked, his shoulders slouched to show his disappointment. 

“You don’t look like a douchebag,” Sam shook his head rapidly. 

“Yes, he does! It’s because of that little neck beard you have going on.” Dean gestured to his face. 

(Y/N) slowly ran his fingers through the hair under his chin, neck, and sides of his face. “What’s wrong with my facial hair?” His voice was quiet.

“(Y/N), don’t listen to him, there is nothing wrong-” Sam began. 

“Sam,” Dean interrupted before looking back at (Y/N). “Look, FBI agents need to be clean to make it more believable. You look like a kid who just got out of a nightlong session playing that…that…War of Worlds or whatever.” 

“World of Warcraft?” (Y/N) arched a brow. 

“Yeah, that. You gotta shave it.” 

“I don’t know how,” 

Dean opened his mouth to speak, but Sam was quick to interrupt. He was sending Dean the deadliest of glares. “Dean, we don’t have time for him to do that. He looks great. He doesn’t need to change anything. Let’s just go, and, if it makes you feel any better, we can say he’s a rookie.” 

Dean sighed. “Fine.” He mumbled before he turned back to (Y/N). “But when we get back, I’ll show you have to shave properly.” 

“Okay,” (Y/N) nodded. 

Dean and Sam then turned and made their way out of the motel. (Y/N) stopped for a moment and returned a hand to his face. He felt the patches of long hair caress his fingertips while the patches of stubble made his hand itch. He scowled.

“I’m not a rookie,” he mumbled to himself before he followed after his brothers. 

“Alright,” Dean grumbled as he pushed the stopper into the sink. He proceeded to fill the basin up with warm water. “Now, one thing that you need to know is that you never, under any circumstances, share razors. Lucky for you, I packed a spare one.” He smiled as he pulled a new razor out of his pocket, handing it off to (Y/N). 

(Y/N) glanced down at the razor. It was one of the cheap ones. One that you would find in a pack of ten or fifteen in a Walmart. The plastic was still hooked onto the side of the blade. (Y/N) took off the plastic bit and tossed it into the small trashcan in the corner of the room. 

“What happens if you share razors?” (Y/N) asked. 

“You can get an infection. You don’t know how clean someone else’s face is, and if you nick yourself, then you’ll be in a lot of pain. Trust me, Sammy and I learned a lot about that when we were younger.” He chuckled. “Okay, the first thing you want to do is get your face wet.” 

Dean set his razor to the side and dipped his hands into the warm water. He leaned his head downward, brought his cupped hand up to his face, and wet his jaw. When he pulled his hand away, droplets fell into the sink below. He then looked at (Y/N), who raised his brows before he followed suit. He dipped his hands into the water, lowered his head, and brought some water to his face. His facial hair clung to his jawline as water dripped from his chin. 

“Right, what I like to do now,” Dean reached down and picked up his razor. He looked in the mirror and tilted his head to the side so that he could fully see the right side of his face. “Is…make a mark on both of my sideburns where the hair meets the face.”

Dean reached the razor up and cut a small portion of his stubble near the hairline. It was only about an inch or two worth of hair. When he was done with the right side, he turned his head and did the same for the left side. He rinsed the razor in the water. 

“You got it?” He raised a brow. 

(Y/N) looked at himself in the mirror, turning his head from side to side. He furrowed his brows and hesitantly reached his razor up. He stopped before the razor could touch his face. “Where do I cut?” He asked timidly. 

Dean sat his razor down and turned to his brother. He looked in the mirror, into his eyes, before he looked back at the side of his head. “You’re gonna wanna cut right…” he trailed as he reached up and ran his finger along the side of his face, about a third of the way down his ear. “Here.” 

(Y/N) reached his hand up and allowed the razor to levitate above the spot Dean had pointed. “Here?” 

“Yeah, right there. And don’t be shy about it. You’ve got this.” 

(Y/N) glanced at Dean before giving a small nod. He then turned and looked in the mirror. He brought the razor to his face and made a small mark on his sideburns, the same as Dean had done with his. Once he was done with the first mark, he looked at his brother. Dean smiled softly at him, confirming that he had done it correctly. (Y/N) then tilted his head to the other side, repeating the process. When he was done, he rinsed his razor, just like Dean had, and looked towards him expectedly. 

“Good, good,” Dean nodded before he reached over to the corner of the sink. He picked up a can of shaving cream, popped the top off, and sprayed a dollop into his hands. He held out the can towards (Y/N), who held out one hand for him. Dean sprayed some of the shaving cream into his hand before he set it on the counter and placed the cap back on. “Now, you want to make sure to cover every part of your face where the hair grows. Just watch and do what I do.” 

(Y/N) gave a small nod and watched as Dean began to apply the shaving cream onto his face, starting with his right cheek before moving down his jawline and to the other. (Y/N) followed his movements exactly. The shaving cream felt different against his face, it was wet and cold, yet soft at the same time. He remembered times at the end of some school years, when he was younger, when the teacher would give them shaving cream on their desks to help clean the surfaces. He remembered drawing faces in the shaving cream, pictures of cartoon ghosts and cats. They proceeded to apply the shaving cream over their cupid’s bows, onto their chins, and their necks. When Dean was done, he rinsed his hand in the water, (Y/N) followed. 

“Alright, the moment of truth,” Dean smiled at him as he picked up his razor. “We’ll start with the face and then make our way down to the neck. Just follow my lead, okay? I’ll go slow.” 

“Okay,” (Y/N) nodded and picked up his razor. 

Both of them turned to face the mirror. (Y/N) stared at his reflection for a moment, a part of him noting how humorous he looked with the beard of shaving cream before his eyes shifted over to Dean. As Dean began to shave his face, (Y/N) copied his movements. Every time Dean rinsed his razor in the sink, (Y/N) did as well. Everywhere Dean put his razor, (Y/N) put his. 

It was a strange sensation, shaving. Since it was his first time, (Y/N) didn’t know how he felt about it. From the curl of his lip when he had to shave his cupid’s bow and chin, to the feeling of the shaving cream slowly running down his neck. It was new, but not disliked. It was easy enough, easier since he was following the live tutorial next to him. He couldn’t help but let his mind wander, though. Let his mind think back to the times when he was younger and watching from some random bathroom doorframe as Dean taught Sam to shave for the first time. Dean held the same expressions on his face back then when he taught Sam as now. A sort of proud, grown expression, giving (Y/N) the first taste of realization that Dean was the one who raised them, not their father. Fathers were supposed to teach their sons how to shave their faces for the first time, not the older brothers. It was almost as if Dean adapted the fatherly role in (Y/N) and Sam’s lives. (Y/N) would never forget that. 

(Y/N) hissed. “Dammit,” he mumbled as he pulled the razor away from his face. 

He looked in the mirror and could see a small, red circle appear on his left cheek. It had been the last strip of facial hair left. He had been doing so well up until then. 

Dean’s head turned towards him before he let out a chuckle. He placed his razor down on the sink and leaned down to snag a small piece of cheap toilet paper. He moved over to his brother and tilted his head so that he could see the nick. Gingerly, he placed the piece of toilet paper onto the red mark. It stuck instantly to (Y/N)’s face. 

“There we go,” Dean smirked and turned back to the sink. “Not bad on the face. One nick is pretty good for your first time. Now, onto the neck.” 

(Y/N) did the same for his neck as he had done for his face, glancing in the mirror at his reflection while, now and then, turning to study his brother’s movements. He shaved his neck without incident, and when he rinsed his razor for the last time in the basin, the water now clouded with a mixture of hair and shaving cream, he felt a sense of accomplishment. He felt proud of himself. When Dean set his razor down, so did (Y/N). They looked at their reflections and examined themselves. 

“And you're done,” Dean nodded. “All we have to do is rinse our faces,” Dean reached over, turned on the warm water from the tap, and cupped his hands to rinse off the rest of the shaving cream. Once Dean was finished, (Y/N) copied. “And we’re done.” Dean smiled at (Y/N) in the mirror. 

When (Y/N) looked at his freshly shaven face, he ran his fingers over the places where the hair had been. The skin was smooth, something that he was going to have to get used to again, and he looked younger, in his opinion. The corner of his lips curled downwards in a frown. 

“I look like a baby,” he mumbled. 

Dean chuckled and shook his head. “No, you don’t. You look like a new man. Hey, facial hair grows back fast, and it’ll grow back a little more even this time. If you wanna keep it, I can show you how to shave around it when it does, to keep you looking clean and not like some homeless guy.” 

“Really?” (Y/N) raised his brows. 

“Of course. As long as you promise not to grow out a lumberjack beard or anything,” Dean dramatically shivered. 

(Y/N) rolled his eyes. “No promises,” he chuckled. 

“Oh!” Dean exclaimed. “Almost forgot. Aftershave!” 

“Aftershave?” 

“Yeah,” Dean reached over to the bottle that sat next to the shaving cream can. It was a small, green bottle of Brut. He splashed some into the palm of his hand before he put some in (Y/N)’s. He placed the bottle onto the counter and capped it. “It helps with those stupid razor burns and bumps.” 

(Y/N) nodded as he looked down at the liquid in his hand. The scent was strong, and he recognized it as something Dean smelled of often. He, once again, copied Dean’s movements as Dean began to massage the liquid into his face and onto his neck. When (Y/N) massaged it onto his left cheek, he felt his skin begin to burn when it ran into the small nick on his face. Dean smirked. 

“Burns, doesn’t it?” 

“Yeah, why the hell does it burn?” 

Dean shrugged. “Not too sure. You’ll get used to it. And once you stop cutting yourself while shaving, it won’t burn as bad.” 

(Y/N) grimaced and continued to rub it in until all he could smell was the Brut and his entire face had been covered. Dean lowered his hands and unplugged the sink. The clouded water began to drain. 

“There, now we’re officially done. What do you think?” 

(Y/N) shrugged. “Not bad. I could get used to it, but I look stupid with this tissue on my face.” 

“Oh, here,” Dean reached over and carefully took the wet paper off of his cut. “See? It’s like you didn’t even cut yourself.” 

“Wow…” (Y/N) turned his face back and forth, examining the spots where the hair used to be. 

“Now you can shave by yourself whenever you want. We just need to get you your own razors, and I can show you how to use an electric one when we get back to the bunker if you want.” Dean crossed his arms over his chest, his smile never faltering. 

An identical smile made its way onto (Y/N)’s lips as he looked over at Dean. “Thanks, Dean. You’re a great big brother,” he spoke quietly. 

Dean tilted his head down, narrowing his eyes. “What was that?” 

“I said ‘You’re a great big brother’.” He spoke a little louder that time.

“Come again?” Dean cupped one of his hands behind his ear. 

“You’re pushing it, Dean.” 

“Alright, alright.” Dean laughed as he reached over and wrapped an arm around (Y/N)’s shoulders. (Y/N) placed his arms around Dean’s torso and hugged him tightly. “For the record, you’re the best little brother a guy could ask for. Just don’t tell Sam.” 

(Y/N) smiled even wider. “I won’t.” 

[mutt-boy]

which winchester brother you are most attached to says so much. dean? oh how is the transition going (ftm). but if it's sam? how is the transition going (mtf).

[callmehector]

*Everywhere I go by Hollywood Undead playing in the background*

Dean(singing along): 🎶When I start drinking my dick does all my thinking🎶

Sam: De- Dean, you don't have a dick

Dean: Exactly

[cas-coding]

he must have eaten something bad, pain blooming in his stomach, soft enough to ignore, but large enough to make him grit his teeth. dean's eggs were sometimes a little on the raw side, but jack didn't mind, he sometimes liked the watery feel, even if sam said it was bad for him now that his grace had faded.

it was fine, he would be fine. jack just wasn't used to pain, that's all, that must be it. his dads had told him it might be a rough transition, cas especially, having done it a couple times. pain was always worse when you had never felt it before.

nausea bubbles up in jack's stomach, making his surroundings spin a bit before he gets the general message that he should get to a toilet or something a little easier to clean vomit off of than the cold cement that was the kitchen floor. he barely makes it to the toilet in time, kneeling on the cold tile, feeling like a knife had carved sigils into his abdomen. this couldn't be normal, could it?

it's another minute before jack wipes his mouth and flushes the toilet, his nausea having worn off for now as he unbuttons his jeans to take pressure off of his stomach. why did it hurt so bad? what was wrong with him? his hands are shaking, massaging his stomach as if that will do something, calling out for help in a wrecked voice that cracks every other word.

he hears footsteps in response and then he's stumbling to stand up, his eyes catching on red. red blood smeared on the tile where he was just sitting, panic flashing through his entire being. he rushes to check his jeans, see where his injury is, pulling them off and finding them bloodstained, his boxers ruined underneath them, and then he's screaming, shouting for help, footsteps growing more frantic.

sam makes it to him first, taking one look at jack's sobbing figure before wrapping him in his arms and pressing jack's face to his chest. "what happened?" sam asks, his voice shaking from the adrenaline, "where does it hurt?"

"my stomach," jack cries, "and i'm bleeding and i threw up and my stomach hurts so bad, please,"

sam nods frantically and pulls back, holding his hand out. "tell me where it hurts, okay?" he places his hand over jack's stomach, right below his ribs, but jack shakes his head.

"lower," he mumbles, "it hurts in my belly."

sam just nods and lowers his hand over jack's belly button, but jack shakes his head, and sam moves his hand lower, cradling the spot just above jack's waistband. jack nods harshly and sam's eyes flick downward for just a second before he sighs and wraps jack in another hug.

"you're gonna be alright, jack, i promise," sam says, "this is, well, it's normal. plenty normal. it hurts but we'll all help, we'll figure something out. you'll be alright in a week." sam reaches for his phone, dialing dean before he pulls back from the hug and stands up, walking just outside the bathroom.

jack only catches every other word being muttered, something about blood and cramps and i thought his grace would stop it? before groaning and snapping at dean, "just get pain meds and pads, will you?"

when sam bends back down to help jack, he's calmer, more collected, but how could he be when jack was in pain, bleeding out?

"sam, it hurts," jack groans, "make it stop, please make it stop."

sam pauses at that, his eyes fixed on jack before looking away. he picks up jack's bloody jeans and throws them into the bathroom sink before he speaks again, still not looking at jack. "dean's getting supplies now. i'm sorry, jack, i'm really sorry this is happening, but we'll explain later, i promise you're gonna be alright. you just have to trust me," he says, but how can jack trust him if he won't tell him what's going on?

it takes a couple minutes for sam to coax jack off the bathroom floor and into a warm bath, looking away as jack climbs into the bath and sighs in relief. he lets jack rest, attempting to scrub the bloodstains out of jack's jeans and boxers, but abandoning it after a few minutes.

there's a knock on the door and dean cranes his head in, waving to jack gingerly before whispering something unintelligible to sam. he sets a box down on the counter, big purple letters spelling out maxi-pads, count 24, and then sam is leaving the room, taking jack's ruined clothes with him.

"hey, jack," dean says, an olive branch, "how're you doing?"

he can't speak, he's exhausted, he doesn't know what's going on, and so he sighs, trying to convey everything bubbling up inside of him with just one sound.

dean laughs. "sounds about right. so, uh, sammy's gonna grab you some new clothes and then we're gonna have a chat. it's gonna be different, somethin' we didn't think we'd have to talk about for a while with you, but hey, life is a bit unexpected," dean chuckles uncomfortably, looking anywhere but at jack. he rubs the back of his neck and sighs, "y'know, i know what you're going through, bud. i've had 'em before, hurts like a bitch, and i'm real sorry it's happening to you. cas said," dean pauses, "well, cas has said a lotta stuff about you."

jack swallows thickly, turning his head to look at dean. the water in the bathtub moves around him, little waves crashing against his neck, barely above the warm water. "he told you?" jack asks, tears welling in his eyes. he's so tired, he just wants to go to sleep, never wake up, he's exhausted,

"no," dean admits, "but i kinda figured about fifteen minutes ago when sammy called me outta the blue sayin' we needed pads. haven't bought those since 2007," he laughs, but it's not funny.

"what are those?"

dean's silent.

"what have they got to do with you and me?" jack rephrases, and dean exhales heavily.

"you want me to explain it? it's gonna be uncomfortable, i'm guessin', you sure you don't want sam or cas to explain it to you?" there's a hurt in dean's eyes for a second, but jack nods and it dissipates, newfound commitment showing instead. "well, if it's gonna be me, i should explain something.

"i ripped up my birth certificate when i was thirteen. y'know, the piece of paper that says your legal name and that you exist and if you're a boy or a girl. well, the one i ripped up said my name was deanna. said i was a girl."

jack furrows his eyebrows. "but that's wrong. your name is dean. sam calls you dean, so does cas. and, and you're a boy, you're sam's brother," jack says, and dean laughs.

"yeah, they do call me dean, and i am sam's brother," he says, "you're right about that. but there's this thing, transgender, which basically means that i was born with girly bits but i'm a boy 'cause i say so. and i was workin' on bein' a real boy, pumping myself full of testosterone when i died and cas rebuilt me. gave me boy parts an' all."

"girly bits?" jack repeats, clearly confused, "boy parts?"

"well," dean says, looking away, "there's your mom. she's a girl. and there's eileen, also a girl. they've got, y'know," dean gestures to his chest, "boobs, tits, breasts, whatever you wanna call 'em. point is, they've also got, ah," dean stutters, "vaginas. things that make babies. that's how your mom made you.

"then there's boys like sam. they get real tall and have big muscles and jawlines and shit," he continues, "they don't usually have vaginas. they have dicks, er, penises, i mean. they can't have babies, they just kinda," dean stutters, "they have the instructions for making babies. they help girls make them."

"oh," jack says, "i don't get it. you're a boy, so how did they confuse you for a girl?"

sighing, dean rubs his hands up and down his face. "well, like i said, i was born with girly bits. had a girly name and everything. but i didn't feel like a girl, and i told sammy, and he started callin' me dean, sayin' i was his brother. felt right, good, and then i wanted to look like a boy. cas rebuilt my body, did he tell you about that?" dean pauses before shaking his head, continuing, "well, when he did, he gave me boy parts instead of the girl parts i used to have. so when i was born, i was supposed to be a mom, carry babies, and now i have the instructions for makin' 'em, but i was a boy before that, you understand that?"

jack nods. "yeah, i get that. like, if i called sam something not-sam, he'd be confused, 'cause he likes being called sam. you didn't like deanna so calling you that would be mean. you like being called dean and a boy, so people should call you that."

dean smiles and nods, raising his eyebrows. "that's right, kid, and it works that way for everyone. you too," he says. the room falls quiet and dean looks away, mumbling, "you feel better?"

jack nods slightly. "the bath is helping."

dean nods, sighing. "jack, you're having a period."

"what?"

"a period," dean repeats, "it's a thing that happens once a month. 'cause you don't have a baby in you, your vagina starts bleeding, like it's mad you don't have a baby, i guess. for most people, it hurts pretty bad, and there's a lotta blood, and you usually bleed for about a week before it goes away."

jack furrows his eyebrows. "but girls have those, and i'm a boy. i don't have a vagina."

"apparently, you do."

it hits jack like a freight train, tears welling up in his eyes, pain searing through his chest, this time not a pain he understood, not a pain he could explain. it was like it was all wrong, everything was wrong, he was wrong, he can't do it, can't be,

"hey, hey, jack," dean coaxes, "breathe, breathe, you're gonna be fine. i used to get 'em, pain in the ass, and i'm still a boy, right? even if i had 'em, you'd still call me dean, right?"

jack's eyes snap open to look at dean, words spilling out of his mouth. "of course! you're dean, dean, you're dean!"

dean laughs lightly, "see? so if i'm still dean, and i'm still a boy, and i used to have the same equipment you have, then you're still jack, and you're still a boy, so there's nothin' to worry about, is there, bud?"

"well, i don't," jack stutters, "i don't like it, it hurts, and it feels wrong, and,"

"hey, hey," dean interrupts, "we'll figure something out, and yeah, it sucks. but it's gonna be alright in the long run, 'kay?"

jack nods. "okay."

"yeah," dean nods, "i think sammy left some new clothes outside the door, so i'm gonna grab 'em, and then i'm gonna show you how to use a pad. it's a bit trickier in boxers, but it works," he mutters, reaching for jack's new clothes.

jack watches as dean demonstrates for him, sticking the pad in place before folding over the wings and setting jack's boxers down. "dry off, don't worry about getting the towel bloody, 'cause we got plenty, and put those on, and then get dressed like normal. i'll be waitin' in the kitchen with something to help the pain, alright?"

jack nods, and dean shuts the bathroom door softly, letting jack sit with his feelings. dean said they would figure something out, that all of them would figure something out, and that it would only last a week. jack could stomach a week of this, if there was less pain, and then it would go away. it would go away and never ever come back, because they'd figure something out.

that's the only thing motivating him to dry off, dress up, and wander out to the kitchen, pain in his belly starting again, curling up inside of him.

cas is there, not dean, and he's got little pink pills sitting in front of him, a glass of water to his left. jack sits down, looking at the pills, refusing to take his eyes off of them. he thought they had magic to help, not just some stupid medication.

"why didn't you tell me?" jack asks, not really to anyone, but cas answers, filling the space in the air.

"i saw you as a baby, heard kelly name you jacqueline, and i didn't think much of it. but then you were big, looked like you were a seventeen year old boy, and i assumed you changed everything to look like a boy. you liked the name jack and we stuck with it. you liked looking like me and dean and sam, you liked being a boy, and i didn't tell anyone. i didn't tell sam or dean because i didn't want them looking at you or treating you differently."

"but you knew dean used to have girl parts." it's a statement, not a question.

"yes," cas says, "and i could have told him. but i wasn't sure you had 'girl parts' anymore, and you were so happy being a normal boy, and we had so many other things going on," he rambles, pausing, "forgive me. i shouldn't have let this fall on you like this. i can't imagine how you feel."

jack sighs, reaching for the pills. "i feel bad. it hurts and then it's worse than just hurt because it feels wrong, like my body isn't supposed to do this, like i'm not a real boy."

"jack," castiel says, voice stern, "you are a boy, and no one can take that away from you. you are my son, and i love you, and i am so, so sorry. please do not ever doubt that you are what you feel you are."

jack doesn't know what to say to that, and so he simply wraps castiel in a hug, sure that whatever happens, his dads will be by his side.

[homoangel]

hello? 911? dean winchester is mega-aggressing his little brother?

#trans!sam #transphobe!dean #deancrit #trans on trans violence

[hotel-casifornia]

something just irks me about hearing people call sam samantha because like guys :( dont you get it thats his deadname dont call him that its samuel now

[boywifesammy]

A study in Winchester Transgenderism (wincest)

my fic for the 2023 spn pro-ship bang!!

this story is the classic wincest pilot reunion in the stanford apartment except sam is FTM and transitioned during college. dean has ~feelings~ about this, both good and bad… and throughout the fic we see him work through it.

all art done by @outofnowhere82, and beta creds to @angellfag :)

read it here!

[yourlocalholler]

finding joy in the mundane. like journaling my little transgender thoughts and watching the most homophobic show cw ever created

[eroswmorals]

why does sam winchester get to have cute chin length hair and be adorable but when i do it i get misgendered?

unfair