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I. 2005

“Hey, Sammy, what’re you reading?”

Sam looks up from the book in his lap and gives Dean a look. “A book.”

“What kind of book?”

“What do you care?”

Dean didn’t, until now. He reaches over to attempt to grab the book, but Sam dodges him easily. “Dude what’s the deal?”

“I just don’t get how this is any of your business. “

“Cause I’m older, so I gotta keep you outta trouble, now c’mon, just show me Sammy.”

“Sam.”

“What?”

“It’s Sam. Watch the fucking road.”

“Fine.” Dean turns to stare down the completely fucking deserted road again. There’s been nothing but corn for the past hour, and before that it’d been wheat. When they get really lucky, there’s some cows to mix things up between fields. “Why d’you always gotta be such a girl about this shit.”

Dean honestly doesn’t give a shit, but he knows the dig makes Sam tense in that self-righteous way he gets.

“You shouldn’t say shit like that.”

Yahtzee. “Shit like what?”

“Like, calling me a girl as an insult.”

“I wasn’t insulting you! You’re just acting like a girl! That’s not an insult, it could be a compliment!”

“From you? How?”

“Dude, girls are cool, I wanna be a girl.”

Sam just sort of stares at him, which makes Dean shift.

“You wanna be a girl?”

“Dude, everyone wants to be a girl sometimes. It’s normal, girls are cool, who wouldn’t want to be one?”

Sam pulls his most ‘how are you this stupid’ face. Fair enough. “Yeah, I don’t think that’s true, Dean. “

Because Dean’s nothing if not committed to the bit, he puts on his worst smile. “Nah Dude, trust me, you still got some growing up to do. Guess they don’t tell you everything in Gender Studies 101.”

Sam goes very quiet for a very long moment. “Dean, I’m a girl.”

Dean frowns at the street, then at Sam. “Like, for real?”

Sam had obviously not been expecting that reaction and freezes for a second. “Pretty sure.”

“Like, taking hormones and changing your name and all that?”

Sam is fucking staring now.

“What? I know people.”

“Name three that you’re not related to.”

There’s a long stretch of silence before Dean decides to let Sam win just for the hell of it. “I think there’s a Biggerson’s coming up, you wanna get lunch?”

“Sure.”

 

II. 2011

“Woah, what the hell.”

Sam looks back at Dean with the kind of amused detachment she’s perfected ever since her soul went off to do its own thing back in hell. They really gotta fucking fix that.

She’s… well, she looks different. There’s something black around her eyes, and Dean can’t really… “Dude, are you wearing foundation?”

“Yeah?” She tilts her head and if it weren’t so fucking uncanny, Dean would almost laugh at her shitty imitation of Cas. “So?”

Sam turns away from Dean to check her reflection in the mirror, and Dean decides to shrug and fucking roll with it, because what the hell else is he gonna do? They got far bigger fish to fry at the moment.

“Not your usual thing, that’s all.”

Sam frowns slightly. “I know that.”

“So, you gonna hit the club?” It’s meant to come off as a brotherly dig, but Deans gonna lose his fucking mind if he has to deal with his soulless sister going off to party. What does he even do if she does? Does he fucking supervise? Whose safety is he concerned about here, because he knows Sam’s extremely good at taking care of herself. Now more than ever.

Thankfully, Sam shakes her head. “I was just curious. I always wanted to try, it seemed like the right time.”

Spoke too fucking soon. “You always wanted to try?” Dean decides to get in the fucking car at last because he’s not having this talk in a Walmart parking lot. “Make-up?”

Sam nods. “It never seemed right before; I think. Not a whole lot of time to figure myself out on the road.”

“And now you’ve got time?”, Dean summarizes as he slams the door shut.

“Now I don’t give a shit about other people.”

“Fair enough.” Dean squints at Sam and, “Doesn’t look half bad, honestly.” It’s subtle, not the heavy shit a lot of women put on. It softens her, makes her look younger, like there was never any demon blood or fucking Lucifer or Hell.

Every single one of Sam’s expressions is smug now unless she’s trying to seem less like a fucking weirdo. She’s not trying now. “I thought so too.”

“You like it?”

“I don’t like anything anymore. But objectively, I look fucking amazing.”

And, shit, what’s he supposed to say to that. “Right.” Dean starts the engine, and they drive out of town. At one point Sam pulls out some wipes to remove the make-up, slowly, methodically, the way she does everything these days. When Dean turns to look at her again, he can see his sister for a split second, before the blank indifference of Sam’s expression registers.

Right.

 

III. 2014

Sam realizes she and Cas barely spend any time alone together. She now knows it’s at least partially thanks to the fucking Gadreel mess, but even before then… Cas tended to stick with Dean. Being alone with him for what may be the first time in ages was… weird, especially since this time didn’t involve any vague hostility from Cas.

“So” They’re driving, which works well-enough for forcing conversation. “How’s the human thing working out?” Sam pulls a face. Not her best work.

Cas gives her a look that Sam doesn’t really know what to do with. If this is anywhere near what Dean feels like, being stared at by Cas (it’s not, not really, but Sam likes to pretend sometimes, to make it easier for Dean to pretend like there’s nothing different about him and Cas), if it’s anything close to that, Sam suddenly understands a whole lot about how people have historically reacted to being seen by angels. Be not a-fucking-fraid indeed. “I understand a lot of things I didn’t before,” is what Cas says, eventually, with the delicate phrasing of someone who has thought about his answer a great deal, “when Anna Fell, she… talked about wanting to experience human emotions.”

“You experience a lot of emotions, then?” Sam guesses, trying for light conversation, but stumbling just before the finish line.

“An exhausting number of them.” Castiel sounds aggrieved by the entire thing. “But that was nothing new.”

It takes Sam everything she’s got to not turn and stare at Cas because what the hell is that supposed to even mean. “Wait, what?”

“I feel… a lot of things, Sam,” Cas says, and he sounds like he’s smiling, but Sam’s not her brother and she’s not turning around in her fucking seat to stare at the angel next to her. “But most of them, I’ve been feeling for years. Humanity only gave me the context I needed for them.”

“Makes… sense?”

“Anna would have been better at explaining it,” Cas sounds almost sorry for being unable to describe… understanding emotions. “She had a way with words. We talked about… humanity, though not long.”

Sam hmms, because it sounds like Cas is about to tell her some kind of story.

“Her experience was different to mine. She chose to Fall, and all that came with it. She chose the body she’d grow up in, the woman she’d become.” Cas sounds wistful, almost. Sam wonders, what the relationship between Cas and Anna had been. She’d barely known either of them, at the time. “It was important to her, that she be born as a woman. I never understood that, until now.”

“Are you a woman?” It’s the first question that comes to mind. The thought makes Sam feel… vaguely like something is attempting to rip out of her.

“No, but this taught me that I will likely never be one. Not the way Anna was.”

“Huh.” Sam’s not sure what else to say to that.

“Angels don’t have… we predate the modern western construct of gender, and most versions that came before.”

“Makes sense you wouldn’t get it then.” God, she wishes she didn’t.

“It would, wouldn’t it?” The smile on Cas’ face isn’t visible, but Sam can hear it.

“What do you mean?”

“I’ve wondered in the past, if… certain things, if they would be easier, if I’d taken a female vessel instead of Jimmy.” Sam can imagine what he might mean. “At the time I chose him based on proximity and how likely he was to say yes, but many people would have been fit to be my vessel, not just Jimmy and Claire.”

“Right.”

“Some of them are women. I wouldn’t choose another body now, of course, not as long as I can remain within Jimmy’s, but I am glad his body is mine. I… doubt I would feel as attached, had I chosen a woman as my vessel.”

“So, you’re telling me that you’re… a man?”

The shifting sound of his coat implies a shrug. “We are all still unique beings, Sam. And I still don’t know if I understand it. Gender. It seems silly, sometimes, especially…”

“Dude, yeah, Dean’s got a whole thing, don’t worry about it.”

Cas’s relief is palpable. “Okay.”

“Like, he’s overcompensating and got a whole lot of complexes about it, and Dean is…”

“He’s Dean.” Cas sounds fond.

“Yeah, that. Like, nobody expects you to be like Dean, he’s… doing the most. At all times. Nobody is expecting you to live up to Dean’s insane idea of gender. Dean doesn’t expect you to live up to his insane idea of gender.”

“Okay. That’s... good.” Cas does sound genuinely relieved.

“So, you’re... not really a man? Man-adjacent?”

“I… suppose so.”

“Cool.” Sam looks towards Cas, but only for a brief second. “Hey. Thanks for telling me, man.”

“Of course. Thank you for listening.”

 

IV. 2019

These days, they rarely all take the same car anymore. It’s easier to have at least two cars at their disposal, so Cas takes his truck, and Dean takes the Impala and they split on whatever case it is they’re working.

This time the truck’s got a busted tire and there isn’t enough time to fix it before they have to hit the road again, which means Cas and Jack are herded into the backseat.

Dean and Sam are bickering in the front when Jack turns to look at Cas from his phone’s screen. He’s gotten really into TikTok lately, which Cas knows is an app popular with young people these days but doesn’t comprehend much beyond that. There are videos, and a lot of floating text and weird faces.

“Dad can I tell you something?” Jack’s voice is small, like he’s scared of the answer, for whatever reason that may be.

Cas freezes, then turns to look at Jack. The fear in Jack’s voice makes him run through several worst-case scenarios in his head, but he tries not to let any of them show on his face. “Of course,” he tells him, keeping his own voice low so it doesn’t disturb Sam and Dean in the front.

Jack nods, and a smile grows on his face. “Thank you, dad.”

Castiel… Castiel leans towards Jack to gently wrap an arm around his shoulder, to briefly squeeze. Jack is rarely comfortable with being touched by anyone but those closest to him, but now he leans into the partial hug, lets his phone fall to the side. “I’ve got this friend,” he tells Castiel, after a moment. “We… we met online. They’ve got more than one father too.”

“They?”

Jack nods, slowly. “Yeah, they’re nonbinary. They said they don’t really understand gender, so they’re not a man or woman.”

Castiel nods. He doesn’t tell Jack that he’s aware of the wide spectrum of human gender experiences, at least in theory.

“Dad, I think I don’t understand gender either.”

Castiel looks down at Jack, who looks like he’s much smaller than before. “You are still very young, Jack, and you have had other things on your mind.”

Jack nods. “I thought so too, I was thinking... it seems weird to say I’m a boy now, right?”

Cas tries to wrack his brain for a smart answer, but he’s falling somewhat flat. Conversations on gender identity were not a part of his parenting curriculum, at least not in any of the books covering toddlers. He’s had similar conversations, but they’d always concerned angels and not humans. Or Nephilim, for that matter. But Jack likely isn’t looking for advice. “If that’s what you think,” he says, carefully.

Jack nods, slow and measured. “I was thinking, there’s so many genders and sexualities and I’m only two years old, it makes sense I won’t get it. So, it makes sense I don’t have any of that yet, you know?”

“That does sound reasonable.” And like Jack has put a lot of thought into it, too.

Jack smiles. “Lee said I could pick my own name, but I think I still want to be Jack, because that’s the name my mom picked for me.”

“It suits you very well.”

Jack’s smile widens and he brightens up. “Thank you, Dad.”

He continues to lean against Cas’s shoulder for a few more minutes, before remembering his phone. He tries to explain TikTok dances to Castiel for a few minutes before giving up and plugging in his headphones to keep watching them.

 

V. 2021

It’s another long midnight drive. Castiel doesn’t recognize the mixtape Dean has put into the tape deck, but he does recognize a few of the songs from the various tapes he’s given him over the past weeks, months, years.

Dean’s been mostly pensive, but eventually he seems to muster up the courage to say what’s been on his mind. “Cas you ever wonder what it’d be like if you were a woman?”

That’s… far from what Castiel had been expecting, and he has to let the question sink in. “Not in a long time,” he says eventually, thinking back on his own confused jealousy at the open affection between Dean and every woman he’d ever desired. Jealousy was a sin, and it had, perhaps, been one of Castiel’s first ones.

“Yeah, Sam says it’s not really something a… how’d she put it… cisgender guy,” Dean says it slowly, like the word is foreign to him, “thinks about, at least not a whole lot.”

“Is it something you think about?” Castiel asks, even if he can assume the answer from the tension in Dean’s expression.

“I mean, it’s fucking weird,” Dean starts, and then keeps going like he’s been holding the words back his entire life. He likely has. “Like, women are hot, objectively, so I just thought it was… normal jealousy? But I guess that’s not a normal thing to be jealous about, and I don’t wanna be like that, it’s more like… knowing I can never be like that, like I’m doing something wrong.” Dean lets out an aggrieved sigh. “Same thing with guys, honestly. Like, I wore my dad’s jacket for ages but it never fucking fit, you know?”

“You haven’t worn that jacket in years.” Not since the apocalypse.

“Feels like I still am.” Dean breathes out sharply, a huff that’s too angry to be a sigh. “I wanna fucking stop wearing the jacket.”

Dean’s always been more comfortable talking in idioms. “What would you want to wear instead?”

“Fuck, I got no idea, Cas.” Dean slumps, like he’d much rather have this conversation anywhere else. “If I knew I—I think I’d have stopped trying, you know? Like, Sam just knew what she wanted.”

“Sam spent many years thinking about what she wants. And I think if you asked her—”

“Yeah, I know, she’s still figuring herself out.” Dean breathes. “I’m fucking forty and I got no fucking clue who I am. Ever since… ever since the mess with Chuck. I was just this—I was just this guy he made to do what he wanted; you know. Gave me my fucking dad’s jacket and I said ‘Yes, sir’ and put it fucking on.”

“But you no longer are,” Cas says, as gently as he can. There’s not a lot about the past year that he’d like to relive.

Dean nods, slowly. “Yeah.”

“We should take a detour,” Cas decides, then. “To find you a new jacket.”

Dean doesn’t quite smile as he turns his head to look at Cas, but he’s no less radiant for it. Cas gently puts his hand on Dean’s shoulder.

“I love you so fucking much,” Dean breathes out. It’s still hard for him, saying that, so Cas smiles.

“I know.”

Dean shoves his arm off, but he's smiling now. Giddy.