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Summary:

"Girl's underwear, Sam, I fucking wear girl's underwear. Happy now?" Dean snarled. He still kept his eyes on the road, features carefully schooled into a mask of indifference.

Continuation to "Just Fine:" Dean and Sam finally discuss the events of that night, and some interesting revelations are made. Not exactly necessary to read that first, but it will improve the experience and it isn't very long. (Not wincest)

This takes place at the start of season 8, but only contains mild spoilers through the middle of season 4. (Specifically, spoilers for one line said in one scene of the episode with no impact on the actual plot.)

Notes:

This story is going to be part of a longer series of one-shots focussed around Dean coming to terms with his identity after purgatory and learning how to take care of himself emotionally speaking, with the help of Sam and yes, also Cas, so keep an eye out for later one-shots if you're a Destiel fangirl! Never gonna be anything sexy or heavy though, 'cause that's not how I roll.

(See the end of the work for more notes.)

Work Text:

Things were tense the next morning.  Sam woke up to find his brother already awake.  He'd opened his mouth to talk to him like a mature adult, but Dean just said, "Breakfast, bitch," and Sam's stomach couldn't help but agree and that was that.  It turned out Dean had found a leviathan case a several hour drive away (how early had he gotten up?), so after the diner they just got in the car, and much as Sam wasn't really one to play fair, it did seem a particular brand of cruelty to start this type of talk in a moving vehicle when Dean couldn't escape.  So the silence between them continued until the tension in the car was stretched as tight as a bowstring and Sam couldn't take it anymore.  "Dean, what you said last night…"

Dean's hands tightened reflexively on the steering wheel.  "Don't, Sammy," he cautioned.  The expression on his face was weary, familiar.

"I just want to know, you said…"  Sam paused and took a deep breath.  "If you're gay, it's not a problem," he finished awkwardly, staring down at his hands.

Dean shook his head, gaze fixed steadfastly on the road ahead.  To Sam's experienced eye, it looked like he was trying to mask strong emotions.  Fear?  "Not gay.  I like girls."

"Bi, then," said Sam, making a dismissive gesture with his hands.  "I just want you to know, it's okay–"

"God dammit, Sammy, I know!  I've heard the speech about a million times, and I know it's okay to be gay!" Dean's knuckles were white where his hands gripped the steering wheel, and his jaw was clenched tight.  Sam almost threw up his hands in exasperation at his stubborn brother.  It was awful to see him do this to himself, when Sam could probably help.  Sam was his brother, who would love him no matter what.  Dean had to know that, right?  Why wouldn't he know that?

"Well, what is it, then?  Because since last night, you've been…"  But it wasn't just since last night, Sam realized.  It was since forever.  Last night was just the culmination of something that had been building a lot longer.  "You've been upset," Sam finished lamely.  "And I know I didn't understand a lot of what you said, but if you help me–"

"Girl's underwear, Sam, I fucking wear girl's underwear. Happy now?" Dean snarled.  He still kept his eyes on the road, features carefully schooled into a mask of indifference.

"Why would that be a problem?" Sam asked casually, doing his best to keep his tone neutral.  This was… unexpected, but still not something Dean had to be so afraid of, right?

Dean cast a glance over at his brother, searching for an ulterior motive, and apparently found none.  He turned his gaze back toward the road, unable to answer.  Taking Dean's silence as permission, Sam continued. "Lots of people do it as a kink."  While the image of his brother in panties wasn't the most appealing, it definitely wasn't as bad as the time Sam was addicted to demon's blood, or released Lucifer from hell, or…  The point was, this was scientific, not supernatural.  "It's a sensation thing, I guess, never really done it for me, but I can see the different pressure, materials–" he broke off as Dean started to talk again.

"It isn't… the 'sensation,' Sam," Dean said awkwardly, and Sam turned his full attention towards his brother.  He owed him that.  When Sam didn't interrupt, Dean pressed on, cheeks burning red.  "I like it… Uh, how I look.  And how it feels, but, yeah."

"Oh," said Sam, feeling lost.  He'd gone into this talk confident that he knew what was going on, that he could do something to make it better, but as usual, he'd misread the entire situation.  How was a person supposed to respond to that?  From their big brother?

"Sam…"  Dean started hesitantly.  "You know how during that Samhain thing all those years ago I said I'd be a hot cheerleader if I could?  And you looked at me like I confessed to killing kittens or something?"

"Oh!"  Comprehension flared like the proverbial lightbulb in Sam's head.  "You, uh… Oh."  Sam looked down at his hands, suddenly ashamed.  He understood why Dean hadn't wanted to talk to him about this.  At the time, he'd assumed it had been a joke and hadn't paid it any mind.  He'd even been concocting a speech about male objectification of the female body.  But now…

"I guess this meatsuit's what I've got, and I ain't complaining," Dean continued, oblivious to his brother's internal struggle.  He spoke casually, but his white-knuckled grip on the steering wheel grew tighter to control the shaking in his hands.  "Other people seem to like it fine.  But it doesn't feel right, not always.  Now, I'm not a chick," he said hastily, casting another glance over at his brother.  "I just– God dammit, Sammy, I don't feel like either, and it sucks."

The silence between them rang louder than a gunshot.  "You know, there's a word for that, Dean," Sam said after a moment, tone still neutral, though the message was clear.  I accept you, I love you, being born with the wrong body doesn't equate to killing kittens.  His brother was his brother (sibling?) no matter what.  This didn't change anything.

Dean's head perked up imperceptibly, jaw unclenching.  It broke Sam's heart to think that Dean might have honestly thought that this admission would lose him his brother, the one person always obligated to be on his side.  "There is?" he asked cautiously, angling his body towards Sam just enough that he could still watch the road.

"Yeah.  There's lots of subcategories, but I think the general term's 'genderqueer.'"  He watched Dean mouth the word, rolling the syllables over on his tongue.  "Like you generally don't feel like either gender label is right for you?"

Dean chuckled dryly.  "Last time I checked I had a dick, so I'm pretty sure–"

"Gender is in the brain, Dean, sex is in the body," Sam interrupted him. "What you feel can be separate from your 'meatsuit.'"

Dean seemed to mull over this new information.  Without saying anything, he stopped and pulled over at the side of the road.  "How do you know this stuff, Sammy?" he asked, finally making eye contact with his brother.

To anyone else, there wouldn't have been any perceptible change in his expression, but Sam saw just how vulnerable his brother looked, all those years of uncertainty and self hatred piled up on his shoulders, and more than anything Sam hated their dad for not being the kind of parent that Dean could talk to about stuff like this.  Or, really, about anything.  And Dean was the last person who should've had to go through that; he had the tendency to get so insecure about even the little things, and he would never be independent.  He needed the people he loved around him to tell him he was okay.  Unfortunately, it was only now that the people who loved him were starting to understand that, because another thing John had taught him was to keep his needs secret.  He learned from childhood to be the untouchable macho man, superman in his palace of solitude.  But Dean never was above it all, never could be.  He cared too much.  Sam wondered what would have happened if their mom hadn't died and he'd had someone to encourage that in him, but that–  that was in the past.

"I had a friend, at Stanford."  Dean flinched reflexively at the mention of Sam's college, but let him go on.  "They were genderqueer and dressed neutrally.  They also preferred us to use only neutral pronouns."  Sam hesitated.  "Would you, uh…"

Dean interrupted him.  "Don't go changing my 'pronouns,' now, Sammy, I'm too old."  He chuckled dryly.

"Then what do you want to do?"

"Nothing, I guess."  He started to put the car back in gear.  "I've lived like this so far."

"But you don't have to."  Sam gripped his shoulder firmly, halting him.  "You know that, right?  I'm not Dad."

After a moment, Dean said, "Yeah, Sammy, I do."  He started the car up and pulled back onto the road.  "Just– just thanks."  Thanking him for what?  For not calling him a freak?  For listening?  For the new word?  All of the above?

"You're welcome, Dean."  Sam sat back in his seat, settling in for a few more hours of driving, Guns n' Roses blaring over the radio.

Notes:

Disclaimer: My personal headcannon, based on what I observe in the show, is that Dean Winchester is genderqueer. However, I am not saying that he actually is, as that is something that cannot be decided by a third party, and I would only be convinced that he is canonically genderqueer if he said something on the show. I hope that my portrayal offends no one, since although a lot of it was taken from experiences of friends who are genderqueer, I myself am not. If you find something you disagree with, by all means let me know! I like to learn from my mistakes.