Dean had always done his best with you. Sure, John had dumped the responsibility of raising you onto him, but he didn’t resent it. Dragging you along on hunts, or leaving you in the motel room, trying to shield you from the worst of it—it wasn’t exactly the childhood you deserved, but it was the only life they knew. And Dean? He wouldn’t have traded you for anything.

Still, something had shifted. You’d been pulling away lately, keeping your distance from both him and Sam. Dean tried to chalk it up to you just needing space, but it gnawed at him. Maybe he’d been too harsh, too impatient when you acted out. He hated to admit it, but patience wasn’t exactly his strong suit.

It all came to a head one night in the Impala, parked outside some run-down diner. After weeks of tension, arguments, and awkward silences, you finally cracked. You told them you were transgender.

The silence that followed felt endless. Dean blinked, his hands still resting on the steering wheel. He hadn’t seen this coming—not at all. But the look on your face, the vulnerability there, cut through any confusion.

“Oh,” Dean said finally, his voice cautious but not unkind. “Okay. So… you’re, uh, a guy now?” He glanced over at Sam, as if checking if he was handling this right.

Sam didn’t hesitate. Turning in his seat, he gave you a reassuring smile and patted your leg. “That’s awesome, man. I’m glad you felt comfortable enough to tell us.”

Dean shifted in his seat, nodding as if to back Sam up. “Yeah. Yeah, of course. I mean, it doesn’t change anything, okay? You’re still you. Just, uh… let me know if I mess up or something. I’ll figure it out.”