I don't own Supernatural.
/
The first time he does it, it's because Sam's just outgrown his last decent shirt and they're officially going to be out of food the next day. John's been gone for nearly a week and a half, and they have a payment due in two days. There are quite literally no other options, it would seem. All the bars know he's too young, there's no one he can play poker against, and John took it out of his skin the only time he stole.
Sam looks at him in blatant horror when he comes out of the bathroom in a tiny bit of eyeliner, a pair of Sam's black jeans that he'd managed to wriggle into and could get out of decently fast, and a Ramones shirt that hugs his body like it's a second skin.
"Dean?" he asks, almost gingerly, but Dean just grabs his coat (John likes to believe it's his coat. Sam and Dean both know that it's actually Dean's, now, because it's the Father Coat, and Dean's the stay-at-home dad of the house) and heads out the door.
"I'll be back in a bit- don't set the motel on fire and stay put."
He doesn't slam the door behind him- he shuts it gently, as though that might help him feel less guilty. It doesn't.
He stakes out a nice place on a corner by a bar, settling against a wall and getting comfortable. He has no idea if anyone will take, but he's hoping (and kind of praying, if he was being honest with himself) that he can get enough to at least get Sam a good shirt, a few packages of cheap ramen, and enough to tide the hotel owner off for a day or so.
The first hour is slow, but it's early evening so that's not surprising at all. Dean's been around enough bars to be anticipating the later crowd.
The kind of people he's expecting start showing up about eight. He watches them from under heavy eyelashes, and knows he's got one, at least, when one of them stares a bit too long at him. They're all businessmen, this is business bar, and he smiles slyly at the man, who, of course, blushes and hurries inside. He settles back against the stone of the wall, waiting as patiently as he would on a hunt. It's a virtue, patience.
He tries not to smirk when, 45 minutes and at least one beer later, the businessman comes out and awkwardly walks over to him.
"Uh, h-hello."
Dean gives him a lazy smile. "Evenin'."
The man swallows hard, following the way his body is angled in a long, lean line away from the building he's leaning against.
The smirk grows. "Likin' what you see?"
Another swallow, mouth falling open just a shade with a bit of a staggered intake of air. Dean pushes off, lazily hooking his fingers in the loops of the man's slacks, tugging him in. "What's wrong? Cat got your tongue?" he drawls, and feels the man shift, looking at him far more hungrily than before.
"How much?" The voice is surprisingly deep, and he appreciates it.
"Take a guess, sweetheart," he murmurs against the man's ear, pleased that they're about the same height. He's 17, just about done growing now. This guy can't be more than maybe a few years older than him, just out of college- he looks like a tax accountant or something.
"I-I've got 200 on me," the man stutters, and Dean's grin goes feral.
Perfect.
And he's even pretty good looking.
"Lucky you," Dean says, pulling back to see that the man's pupils are blown wide. "Let's get this show on the road then."
\/\/
Okay, so he really hadn't been expecting the sex to be that fantastic. He's been with guys before, and none of them had made him feel that good. Hell, he hadn't felt that good with a lot of women.
They're sprawled in a bed in a motel that rooms are bought by-the-hour in, and Mr. Tax-Accountant guy (who gave the name of Jimmy- like anyone'd believe that) is clearly having a crisis of conscience. Dean doesn't really give two shits about that, because, hello, he has been paid and can now buy food.
After he showers.
Repeatedly.
With a lot of hot water and scrubbing because he feels absolutely filthy.
Damn, the sex was good though.
/\/\
That night, Jimmy gets home to a crappy apartment, curls up, and wonders what the hell possessed him. In a few days, he'll go to church and beg forgiveness, shaking like he's about to break apart.
An angel by the name of Castiel will happen to be watching him, as fascinated by humans as ever, come down, and curl around him in a massive hug that will reaffirm Jimmy's faith and build an incredible, unbreakable bond between the two of them that will literally survive until the end of time.
After John has gotten back, Sam has a whole new wardrobe, they've feasted like kings, and the nice lady in the office has been paid, Dean will also go to church, curiously the one across from where one Jimmy Novak is praying desperately and about to receive the peace he so desperately needs. He'll kneel down, swallow awkwardly, and for the first time in his life, pray for the strength to do what he knows he'll have to now. Because there's no way he'll let Sam play poker in shady bars now he knows what he can do with tight clothes and a bit of burned plants dabbed around his eyes.
The priest will give him an odd look, because this strange young teenage boy is quietly crying in his church, but he'll stay away until the tears are dried up, and the massive brown leather jacket is settled on still-thin shoulders. As the boy is leaving, he'll ask, "Are you alright?"
And the saddest, most tired eyes he'll ever see, eyes that will haunt his memory until the day he dies, will turn to him and smile, and say, "Never better."
\/\/
Fast forward several years. Dean dies. John dies. Dean comes back. Sam gets superpowers that nearly kill him and, oh, happen to have been given him by a mother-killing demon. Dean dies again. He goes to hell.
And an angel drags him out.
An angel, clothed in a man by the name of Jimmy.
From Illinois.
Who looks like a tax accountant.
Which is why Dean sits bolt upright one night, eyes wide in realization to see Castiel, angel of the friggin' Lord, smiling down on him with the smuggest, stupidest smirk on his face.
"You absolute bastard," he hisses. "You knew, didn't you?"
And Castiel just smiles, and disappears in a rush of wings.