Dean's always known he wasn't the person he pretended to be. Ever since he was young, when his eyes would linger on the wrong people, he'd watch the wrong shows, he'd think the wrong thoughts, wrong, wrong, wrong. Even Sammy did better than him.
On his 17th birthday, his dad sent him to a church to salt and burn two nuns who were in love before death. Dean got the message louder and clearer than any belt buckle on his back or fist in his face.
So he kept it down. What kind of man was he, really? He flirted with women at bars because that's what men liked, wore the flannel his dad wore because that's what men wore, talked about whiskey and cars and guns because that's what men talked about. And what chance for experimentation did he get when all of his time was spent hunting or preparing for hunting with a father so overwhelming he could barely breathe?
But his dad's not here. He's doing some kinda solo thing and didn't really give a shit where Dean went. He hasn't seen him in weeks. Sammy's off at Stanford. He's alone. There's no one to lie to, no one who will remember him a year from now. He can be the horribly wrong thing he is and no one will give a shit.
It was late, the moon barely shining through the window as Dean sat at a barstool, psyching himself out. In a momentary lapse of judgement while looking to have a night out, his mind had not thought 'Dean, you are a heterosexual man who doesn't belong in a gay bar', it had thought 'Dean, you should definitely go to the gay bar'.
And there he was, hiding in the corner while trying to pretend he wasn't hiding in the corner, nursing a shitty beer and thinking about everyone seemed so happy and open and how he really should leave because someone like him shouldn't be here even if he did maybe like men, and—
A man sat down at the stool next him and flashed him a smile and all his spiraling was temporarily replaced with 'Holy fuck, is that guy good-looking'. He really should leave.
You smiled at him again, and turned to face him before asking if you could buy his next drink. You called him handsome, too. Fuck. He should say no. He should leave and go back to his motel and forget this ever happened.
"...Yeah," he finally got out in a gruff tone, before averting eye contact. God. He isn't used to something like this. He can hear his dad's voice ringing in his ears clear as a bell and he's acting cagey. You can probably tell he's acting cagey. You should leave. He doesn't want you to leave.
"So, what's your name?" you ask as you gesture the bartender for a drink, biceps flexing. Dean stares at the strong line that is your jawline. He quietly mutters that it's Dean, and you chuckle. "A pretty name for a pretty face," you reply (with a wink) and Dean feels his face get hot.