Work Text:
Dean knows he doesn’t exactly cut the image of a night walker. Most people imagine something like faux furs, mesh shirts, caked makeup, waifish figures. He’s “husky”. Wears plaid. He usually has a can of beer in hand and spits a loogie before leaning into windows. He’s not exactly the sort that’s bathed in neon lights. He doesn’t have some torrid affair with an ex cop or a kid at home he’s trying to support.
He’s just a guy that’s good with his body and knows it. He puts people at ease, likes to fuck, would rather do this than hard labor that’s for sure. He doesn’t care if you wanna kiss him. He has his own place he takes his Johns to. He’s got a nice car he fine tunes during the days and a brother he calls every evening and friends at the bar.
This isn’t all said to disparage anyone who does fit that bill. He doesn’t think he’s better than the girls in platform heels or the boys with elaborate wigs. He likes them, they got a fun energy. He just means to say that he wouldn’t ever think he’d find himself in some sort of fairy tale relationship. He wasn’t gonna femme fatale some sexy, gruff PI. He wasn’t gonna be whisked out of his drab life by a rich businessman.
He thought he’d had it all figured out. But then a John just so happened to want to be sucked off in this roadside diner. He was looking for someone “discrete”. Aka he didn’t want the wife knowing. He was into understall, said he knew a place. Understall was easy money. Dean could have fun with a nice cock and not have to look some dead in the eyes dad in the face.
So he took the job. They had a checkered linoleum floor. They had a rotating glass case of pies. Their coffee smelled burnt and there weren’t any waiters on the floor when he came in. It was definitely his kinda haunt and he was determined to at least try a slice after. But business before pleasure, so he hit the head first.
The John was already in his stall when Dean got there. By the look of his shadow on the floor, jacking it to some porn on his cell phone. Dean hoped he came fast. Understall was good, but it killed his damn knees and the stalls were small in this place. He’d be sucking with his arm propped on the can for sure.
The work went fairly quick, that’s not the interesting part of the night. Dude had shaved himself clean and had one of those weird dimples where his cock connected to his body. Dean wasn’t super a fan. Razor bumps weren’t particularly sexy. But his dickhead was fast and his cum tasted fine and he’d already worked himself up so much he was gushing down Dean’s throat before he even had to reshuffle his weight.
What mattered was what came after. Some cute little thing came up and took his order at the bar after a minute of waiting. His hair was a real fuckin’ mess, probably from a long day. He had bags under his eyes from probably a long week. His voice was all gravelly from probably a long life. Dean ordered a coffee while he looked over the menu to get the scent of spunk off his breath, though it didn’t seem like “Cas” (as his nametag said) had initially missed that.
The place had everything a perpetually chubby guy could ask for. He’d got his jeans in the husky section since he was ten and had a respectively inappropriate relationship with food ever since. Dad put him in too many sports to over compensate. Dean developed a thing about sneaking junk food. So now he got hard when he ate stuff that was notably fattening. Go figure.
“Biscuits and gravy. A buttermilk pancake. Two fried eggs. Hashbrowns extra crispy. Whichever pie you’re particularly proud of.” He stirred a little just rattling it off, but went full blown chub when Cas grinned at him.
“Work up an appetite in there?” he husked, implying either he definitely knew Dean had been blowing that guy, or at the least that he’d taken a mondo dump before sitting down. Dean bit his bottom lip, wiggled his ears a little in response.
“What do you think?” Dude better watch out. Dean’s flirting paid the fuckin’ bills. He could take this cutie to the can just as quickly as the last guy. And then they’d see how funny it was to swallow some spunk in a shitty diner.
Those tired eyes woke up a little more as the guy chuckled a little, sucking his teeth at Dean’s brazenness. “I think the coconut cream would stick to your sides real nice.” And then Dean did something he didn’t think he’d ever done. He blushed. He stammered. He lost his words as Cas laughed his way into the kitchen to whip up his meal.
See, Dean was very sure of himself now. He knew what he was, what he liked, where he thought his life would go. He didn’t care, at this point, what others might see. He wasn’t some flashy escort. He wasn’t an all star quarter back. He was over trying to prove something to a fuck off dad, to this idealized version of himself he thought he had to be.
He was self sufficient. He was a good brother. He had some close friends. What the fuck else really mattered in this life? But maybe, apparently, there was still some little sliver of him that needed validation. There was some lonely, angry kid still buried down deep that couldn’t understand what else he needed to do.
And that kid was a little fucked up at the glancing mention that maybe someone liked him like this. Dean was good with his body. Didn’t exactly mean he was all 100% square with it. See, taking tricks isn’t the same as making love. And maybe he’s still got holdups around the latter. Maybe he’s had some dreams sometimes about getting his stretch marks licked. About asking for his squishy tits to get sucked. About having his thighs bitten and his belly outright groped while he’s fucked doggy.
And those dreams make him feel weird. Vulnerable like he hasn’t been for a long time. Scared and disgusted with himself. Wistful for some shit he can’t even imagine. He has this home sickness for a thing that never existed and he’s not even really sure that he wants.
But Cas sits all his plates in front of him and leans back against the counter to watch him eat, asking if there’s anything else Dean desires. They shoot the shit and Dean feels funny, but isn’t afraid to eat his whole fucking meal. He doesn’t even act like it was insane for him to eat that much, or that he’s sick with it, and Cas says the grill is still hot if he really wants to make a night of it.
Dean didn’t think he was that guy, but he asks for the cute waiter’s number. He becomes a regular. He thinks of pretty blue eyes when he fucks his Johns and keeps Cas company on his long night shifts. He dreams of running away together, of making love in some sun dappled kitchen with custard colored walls and a pie cooling on the window sill.
He suddenly wants to be the guy that’s in all those silly romance books. But not because he thinks he has to be. Because he thinks maybe that guy could’ve always been someone like him. He’s worth kissing in the rain and making up pet names for and taking on long, late night drives.
He’s the sex worker that fell in love, when he didn’t think love was a real thing. And it’s so fucking stupid and perfect and amazing. It’s a great story to tell Sammy, though he thinks maybe he’ll leave out the whole dick on his breath thing. Maybe.