Well... I couldn’t help myself. So here’s part 3 to this.
Sam walks in wearing something Dean’s never seen and Dean does a double take. He stares at him.
Them! Them, you idiot, your nonbinary sibling, not your brother, them, them, them.
Sam sighs heavily and says, “I’ll change.” They’ve half turned around when Dean finally finds his voice.
“No, it’s fine, just give me a sec. Lemme see.”
Sam hesitantly turns to look at him, spreading their arms self-deprecatingly. Their face is flaming. Dean looks them up and down carefully.
Sam’s holding the tag in his – their their their their their – hand. It’s an XL.
The dress is floor-length. It has two slits on the sides, making it essentially three-quarters around the back and a separate piece in the front. It’s form-fitting from the hips up, emphasizing the curve of Sam’s ass and waist. They’ve filled out the front so it doesn’t hang all baggy off of their chest. It has spaghetti straps that go over their shoulders and meet in the back. Their arms, neck, and chest down past their collarbones are entirely bare. Dean feels a sudden, odd, almost parental urge to force them to put on a jacket or something.
He glances down at the floor. He can see through the slits in the dress that Sam shaved their legs. Interesting. They’re also wearing a pair of black strapped pumps with a four-inch heel.
He looks back at their face. Their hair is slightly longer than he remembers and pulled up into a ponytail. They look really… cute.
“Does it make you happy, Sam?” Dean asks when he’s satisfactorily completed his examination.
Sam looks a little surprised, a little shocked, a little embarrassed, and a lot joyful. Like they weren’t expecting Dean to ask but it’s the best thing he could have done. “Dean,” they say eventually in this tone like they’ve discovered all the secrets of the universe. “This is the best thing I have ever worn.”
Dean makes eye contact and smiles. “Then fuckin’ wear it, Sammi. Your gender is your own. I have no place tryna tell you how you can or can’t express it. If it makes you happy then wear it.”
Sam hugs him hard enough to crack a few ribs. “Sammi,” Dean murmurs eventually, sounding pained even to himself. “Gonna want those lungs to be functional. Try not to crush ‘em.”
Sam nods and lets him go. “I- sorry. I love you, Dean.” They nearly sprint out of the room. Dean follows.
Sam makes their way into their bedroom and Cas is waiting for them there. Dean watches with fondness as Sam launches themself at the angel. Cas hugs them happily.
“He liked it,” Sam whispers, sounding giddy. “He fucking likes it.”
Cas is grinning at Dean over Sam’s shoulder. “I’m so glad, Sam.”
Dean’s heart is about twelve sizes too big for his chest. Or maybe his chest is compressing. Either way, it’s uncomfortably tight, and Dean almost hates it, but the look on Sam’s face wipes that into oblivion.
Sam lets go of the angel but they don’t really look embarrassed, just happy, and-
Holy. Fuck.
Sam’s looking at Cas with this expression like he’s the only thing that matters in the universe and Dean would be jealous if he wasn’t so shocked.
Holy fuck my sibling is in love with an angel.
He looks away. This is suddenly too private for him to see. He starts to walk away but Sam grabs his wrist. “Dude,” they say. “Been tryna break you of this habit forever. You can’t just fuck off when something happens that makes you feel stuff.”
Dean sighs. “But why?”
Sam laughs. “You’re stupid and annoying and my best friend and I love you. And you’re not getting on my case for wearing a dress, so props to you.”
“I like dudes,” Dean says and it’s so weird and it doesn’t sound right and his voice cracks but it’s also real. And Sam nods.
“Yeah, I know. Waiting for you to figure it out but I know.” They don’t look smug or anything, just sympathetic, like they know how hard it is for Dean to admit that.
Dean glances between the two of them, Cas where he’s sitting on the couch with his hands folded in his lap and Sam where h- they are standing in front of Dean looking adorably eager and Dean’s about to spontaneously combust. He swallows hard, taking Sam’s hand, and leads them into the kitchen.
“Dude, are you in love with Cas?”
Sam freezes. “Um.”
Dean honest-to-God laughs. “Holy shit, you are.”
“Maybe,” Sam admits.
Dean doesn’t know what to do, but he does know what to say. “Dude. Fuck him.”
Sam shakes their head. “Oh my god. No. I’m-”
“A bottom, yeah I know. But like. Sleep with him, dude.”
Sam sighs. “I don’t think she’s interested.”
Dean stares at them. “You don’t think he’s interested? He takes you shopping for shit like this outfit every single day. He spends most of his time with you. If anyone’s interested, it’s him. Go for it.”
Sam bites their lip, looking vulnerable and almost scared. “Are you sure? You really think so?”
“Dear god. Yes, I do. Just go.”
Sam swallows hard, nods, and goes, and Dean watches them disappear into the other room.
Two days later, he walks in on them mostly naked making out with Cas.
He hightails it out of there.
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