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Sam loved having his own room. He'd never had a space to himself in his whole life. Even at college he'd had roommates; first in the dorms, and then the apartment with Jess. Being able to shut the door and have time alone without needing to be constantly alert to the possibility of someone else walking in was an amazing feeling, and one he relished in. Especially because it finally allowed him to do some exploring.
Sam wasn't sure he'd call himself transgender. The few precious moments he'd been able to spend online doing research, or that one LGBT rally on campus he'd been to had only given him the barest sense of what that word meant, and John's man's-man upbringing hadn't left Sam with much ability to feel confident enough to do much else. “Boys don't cry.” “That hair makes you look like a girl.” “Stop being such a sissy.” And if John wasn’t enough, Dean sure as hell made it a point to remind Sam that gender variance was not allowed - pointed barbs letting Sam know exactly when he was stepping too close to that line. So Sam kept his feelings to himself and learned to let the insults roll off him without reacting. He deserved an Oscar for how nonchalant he’d learned to look.
He’d just begun to talk to Jess about it when she died. She’d been so sweet and supportive and even went with him to buy a few more feminine clothing items, happy to pretend that they were for her so Sam wouldn’t be afraid of people knowing. Jess had even snuck a mini skirt (that Sam had been too embarrassed to admit liking) into the basket and presented it to him with great flourish. She helped teach Sam to shave his legs, and wolf whistled when Sam modeled the skirt (which made his long smooth legs look amazing). Sam blushed, and decided right then he was going to start growing his hair out.
Jess had tried to convince him to use Halloween as an excuse to finally try going out in public wearing feminine clothing, but Sam’s adamant hatred of the holiday trumped the excitement of a socially acceptable reason to go out in a skirt. And then Dean showed up, Jess died, and Sam tried to forget how amazing that week of exploration had been. There was no way in hell he was going to risk Dean finding women’s cloths in his duffel. So he shoved that part of himself as far down as it would go, trying to forget how he felt right for the first time when he modeled that skirt for Jess. He still grew his hair out though - not so much that Dean would be suspicious, but enough that it made him feel pretty.
But now Sam had his own room. Now Sam had places he could hide feminine clothing where he was sure Dean wouldn’t find them. He could lock the door and not worry about Dean barging in. Sam was tired of hiding, of pushing those thoughts and feelings down so deep he felt like he might choke on them. So, once they’d been in the bunker long enough to establish routines that Sam could predict, he went shopping.
Sam decided to go with a thrift store - there were less roaming “helpful” employees. His face was already hot with embarrassment as he entered and tried to look subtle and nonchalant as he meandered over to the women’s section. The ache of Jess’ loss had dulled over the years, but it flared up with a vengeance as he looked over the racks in bewilderment. He had absolutely no idea what he was doing, and he missed the silent support and chattering distraction of Jess’ presence. He started to feel horribly uncomfortable and quickly picked out a few short sleeved shirts (his arms were way too long and bulky to fit anything else) and camisoles with built in bras (no way was he buying lingerie by himself) and a short skirt that reminded him of the one he had at Stanford. As soon as enough items were in hand for an outfit, he payed and fled.
The nice (ish) whiskey he brought back to the bunker effectively distracted Dean from asking what had taken him so long at the store, much to Sam’s relief.
Over the next few weeks, Sam felt like he was walking on eggshells, just waiting for Dean to walk in, holding Sam’s new cloths, and demand an explanation. Sam had put them on a few times when he was sure Dean would be out for the evening, and it was like a band had released from around his chest as he looked in the mirror. Like he could breathe for the first time. He desperately wanted to try on some makeup, or shave his legs, but the cloths were risky enough as it was and he didn’t dare try anything further.
At least, not at first.
The longer they stayed in the bunker, and the more time passed without Dean finding out, the bolder Sam became. A small amount of drugstore makeup found its way into a hidden drawer in his desk as did, eventually, a few simple bra and panty sets. Thank god the Men of Letters were paranoid secretive bastards - there were plenty of hiding spaces. Sam desperately wanted a pair of shoes that would go with the small wardrobe he was accumulating, but his feet were just too large to fit the sizes at most stores, and like hell was he going to risk ordering some online. So, for now, he went without. More and more, he was starting to think of himself as a girl in the privacy of this thoughts, and Sam knew that was dangerous territory he could never wander too far into. He drew the line at using female pronouns in his own head, knowing that it’d be too easy to slip in front of someone else. And that absolutely could not happen. Ever.
Of course, with the Winchesters, no secret remains that way forever.
Dean had said he was going out for the night and Sam had done his best to not look too eager at the prospect of an evening alone. It had been a long while since Dean had spent the evening at a bar, and Sam was almost itching with the need to be out of his stupid man cloths and be herself HIMSELF. Sam waited twenty minutes after Dean left before heading to his room to change.
Dean’s favorite bar was swarming with cops when Dean pulled up and he cursed in irritation. A quick conversation with the distraught looking bartender told him that a bar fight had gone wrong and one of the participants had died, so the police were interviewing everyone and the bar was likely going to be shut down for the night. Then one of the cops had frowned a little too hard at Dean’s face and he quickly drove off in the Impala. They were usually safe, but it had only been a few years since the Leviathan doppelgangers were all over the news, and Dean wasn’t willing to risk being recognised. Dean contemplated trolling for a different establishment, he’d driven half an hour to go out after all, but the paranoia that the cop had recognized him and maybe called around to ask other places to keep a look out caused him to decide against it. Instead he turned back onto the highway toward the bunker.
“SAM!” Dean called out when he entered the bunker, dropping his keys into the tacky Batman candy dish Charlie had gotten for them as a joke. He frowned when he got no response and decided to go looking. Dean was so intent on needing to tell Sam they might need to avoid that neighboring town for a while that he forgot to knock.
It was the look on his brother’s face that Dean noticed first. Shock, horror, then shame all flying across Sam’s features.
“Dean! I can explain!”
It was only then that Dean noticed Sam was wearing makeup and, his eyes flicked downward, women’s cloths. All thoughts of needing to be extra careful about police flew out of Dean’s head and he just stared at Sam, trying to find the words.
“Why don’t we…” Dean jerked his thumb towards the common area where there was seating, and booze, and turned around to leave without checking to see if Sam followed.
Dean plunked himself down at the map table, picking up the bottle left there from the night before, and poured himself a few fingers into a dirty glass. He threw back the first and was refilling when he noticed Sam standing awkwardly in the doorway. Dean pushed the refilled glass in front of an empty seat, inviting Sam to sit, as he touched the bottle to his lips. Sam sat, shoulders hunched, staring at his hands. He chewed on his glossy lip, thoughts racing, searching for the right thing to say while waiting for Dean to go off.
After a few minutes of silence had passed, Dean put down the bottle. “I’m waiting for that explanation Sammy.” It wasn’t gentle, but it wasn’t angry either. Not yet. Sam took a deep breath.
“I…. I like wearing girls clothes.”
“Kinky.”
Sam let out a frustrated noise. “It’s not a kink Dean.”
Dean swallowed, like he was about to admit something, before settling with “It’s cool if it is. Just, ya know, put a sock on the door.”
Sam glared at him, exasperated. “It’s not a sex thing Dean! It’s… who I am? I don’t know. It’s not about getting off, it’s about feeling right.” Sam made a frustrated noise in his throat and ran his fingers through his hair. “I just… feel better when I’m dressed like this.”
Dean frowned, “So what. You want to be a girl or something?”
Sam looked anywhere but at Dean. “I don’t know. Maybe.” He made a noise that was somewhere between a snort, sigh, and sob and put his face in his hands. “God I’m such a freak.”
“It’d be okay if you did you know.”
Sam didn’t look up. “If I did what?”
“If you wanted to be a girl.”
Sam’s head flew up to gape at Dean. “What?”
“It’d be okay if you wanted to be a girl.”
Sam’s mouth worked, searching for words. This flew in the face of every fear he’d had of Dean finding out. Dean took another pull of whisky as Sam finally found some words. “But you always teased me! Gave me shit when I wasn’t ‘manly’ enough! You called me Samantha to make fun of me!”
Dean shifted uncomfortably. “Well, I had to do something to keep you from doing something obvious in front of Dad.”
Sam gaped at Dean. “What!?”
Dean snorted. “Sammy, you asked me for a dress like the girl in the pull-ups commercial when you were three. I didn’t know what that meant then, only that Dad would be furious if he ever found out you wanted anything like that. I couldn’t let anything happen to you, so I had to make sure you never said or did anything that would let on in front of Dad or anyone who’d tell him.”
“Dad’s been dead for years Dean.” Sam exclaimed, his voice rising in volume.
“We troll newspapers for murders Sammy. I’ve seen enough about dudes who became chicks getting murdered for it to know what it means, and I just couldn’t let something like that happen to you.”
Sam exploded. “You could have just talked to me Dean! I’ve spent all this time terrified that if you ever find out you’d hate me! We risk our lives every day for other people to be happy! Why the hell can’t I risk mine for something that’d make me happy!?”
Dean locked eyes with Sam. “Would being a girl make you happy Sam?”
Sam deflated and looked away. “I don’t know, maybe, I’ve never really had a chance to try and find out.”
Dean nodded, like he’d made a decision. “Well then, let’s find out. We’ll go shopping tomorrow.”
Sam blinked in surprise. “What?”
Dean took another swig of the whisky and gestured to Sam’s outfit. “You look like a hooker Sam. If you’re gonna be a girl, at least be a classy one.”
Sam’s cheeks flamed. “DEAN!”
Dean snickered. “And your makeups a mess. We’ll have to buy you some better supplies too.”
“What the hell do you know about makeup?” Sam sputtered in shock and disbelief.
Dean stood up, and grabbed Sam’s untouched whisky from in front of him. “Spent the weekend with a girl in makeup school Sammy. The things she agreed to do in exchange for getting to doll me up.” Dean whistled and waggled his eyebrows.
Sam made a face. “You’re disgusting.
Dean laughed and started to head out of the room, glass in hand. “Well my depravity is about to get you a lesson in how to look like a classy dame Sammy!”
“Don’t call me Sammy.” Sam said out of habit.
Dean paused, and then, without an ounce of derision said, “Sure thing Samantha” and left the room.
Sam sat there, in awe, staring at the empty doorway Dean had gone through. Nothing about that conversation had gone at all like Sam had expected. After a few minutes of sitting there in the silence, Sam picked up the whisky bottle and took a large swig. The chair screeched along the floor as Sam stood to go to bed. The tightness that had always lived in Sam’s chest loosened as Dean’s promise of shopping and support echoed in the silence.
She smiled.