The first time Dean does it, he's seventeen and Dad's been gone long enough that the cash has all but run out. "I'll be back in a couple of days," Dad says over the phone, like it's nothing, like Sam's stomach isn't growling audibly over the TV's laugh track. "If you're that hard up, go do what you need to do. But you should have been more responsible with that money, Dean. I gave you plenty."
He waits til he's hung up the phone to swear, then sits down and starts pulling on his boots.
"Where ya going?" Sammy asks, muting the TV and sitting up interestedly.
Dean shrugs on his coat and gives Sam a smile he hopes isn't too phony. "I'm gonna go get us some grub," he says, turning away from Sam's eager eyes. "I'll be back in a few. You stay in the room, lock up-"
"I know, Dean," Sam sighs, turning the volume back on and drooping back. He rubs his stomach absently, and Dean curses his dad under his breath one more time before he pulls the door closed behind him.
He heads to the nearest dive, where he flashes an ID as fake as the bartender's tits and buys himself into a card game with the few bucks he had stashed away for emergencies. For awhile he's up, almost enough to start thinking about cashing out and hitting the nearest 24-hour diner, but then he gets a crap hand and finds himself up shit creek without a paddle, nothing but three bucks to his name and the bartender calling out for last rounds.
One of the men he's been playing gives him a sympathetic look. "Tell you what, son," he says, rubbing at his mustache with work-rough fingers. "Come on over here, let me buy you a drink."
Dean almost declines, but the man gives him a look that suggests there might be more to that offer and Dean figures anything, even charity from a stranger, is better than heading back to that motel room empty-handed. He follows the man to the bar, and he shoots back the whiskey the man buys him with an easy smile that, he hopes, makes him look young and charming and desperate.
"Might be I'm readin' this wrong," the man drawls after a moment, looking at Dean keenly, "but I'm thinkin' you need this money more'n I do."
"I don't make a habit of accepting hand outs, sir," Dean says automatically. He feels a flash of guilt, because Sammy, but it's the truth, and he's gotta say it at least once.
The man smiles, his dark eyes lighting up. "Well, that's all right. I'm gonna give you the chance to earn it back." He nods towards the back door, and Dean's spirits rise.
Dean figures there's a craps game or something going in the alley behind the bar, so it takes him by surprise when instead the alley's quiet and empty, and it downright startles him when the man starts trying to get handsy with him. He shoves the guy off and presses him up against the wall, his eyes going hard. "What the hell, man?"
The man looks affronted. "What'd you think I wanted with you, boy? A chat?"
Dean's hands are shaking where they're balled up in the man's shirt, his throat dry and his pulse hammering. "You think I'm just gonna- I'm not-" He can't get his mind and his mouth to agree; everything's befuddled and strange, nothing making any sense.
"Oh," the man says softly, pity stealing into his eyes. "You never done this before?" When Dean doesn't answer, he slides his hands up and lays them gently over Dean's. "All right, easy now. I'm gonna make this nice and easy for you. Look here." He reaches up to the pocket on the front of his shirt and pulls out a fifty dollar bill, holding it right in Dean's face. "Fifty bucks, and all you gotta do is stand back and let me make you feel good. How's that sound, huh? Ain't gonna get a better deal nowhere else, I can tell you that much."
Dean wants to tell this man to go fuck right off…but he's transfixed by that fifty dollar bill. "You're not putting anything in me," he finds himself saying, his face hot, and the man just laughs and tucks the cash into Dean's back pocket.
"No," he agrees, loosening Dean's hands from his shirt and carefully maneuvering them so that it's Dean with his back to the wall and his breath coming too fast, "you ever do that, you be sure'n charge more for it. Don't let nobody talk you down past two hundred dollars, son, not for that." He licks his lips and presses in close, breathing Dean in. "Bet you'd be worth every damn penny, too."
The words make Dean shudder, as do the man's rough fingers working at his fly. He closes his eyes when the man starts touching him, embarrassed by the way his body is reacting without his permission. When the man drops down to his knees and starts working Dean with his mouth, his mustache tickling Dean's skin, Dean has to cover his face with both hands. The noises he makes are muffled, but he can hear them still: choked off moans, throaty desperate noises that make him seem like he wants this, like it isn't just the money in his pocket keeping pressed against that wall.
When he comes, it's with a stifled sob and a hot, sick feeling churning in his guts.
Later, when he's schooled his expression into its usual mask of playful disregard, he lets himself back into the motel. Sammy leaps up and runs over, grabbing the paper bag out of Dean's hands and digging into the chow Dean scrounged up with such enthusiasm it makes Dean's heart hurt. His mouth full, he grins up at Dean, and Dean can't think anything but that it was worth it.
Still, he decides, he won't do that again. If Sam knew what Dean had done for that cheeseburger he wouldn't touch it, much less look at Dean so appreciatively. So Dean makes a joke about Sam making himself sick from eating too fast, and he slinks off to the bathroom where he runs the hottest shower he can stand. Under the spray of the water, he tells himself over and over, like a mantra: "Never again."
X
Unfortunately, there's a lot more cash to be made with Dean's body than with his mind. He's okay at cards, but he's got nothing on his dad (and Sammy beats the pants off of them both, though neither of them willingly admit as much), and while he's a pretty damn good pool shark, it's not the most consistent work. After Sammy's gone off to Stanford and Dad starts sending Dean off on jobs on his own, money gets tighter and earning it becomes a question that nags at him almost constantly. It's a lot faster and easier to earn a few bucks in a truck stop bathroom than it is to hustle pool or swindle credit card companies, and what nobody but Dean knows isn't gonna hurt, or so Dean figures. If he's on his own, he can put gas in Baby and food in his stomach however he pleases.
And, besides, the work isn't exactly a hardship.
At first, Dean has strict rules. He finds enough lonely older men who are willing to fork over some cash just to touch him, and it almost seems like its own kind of hustle, that he's the one getting paid and the one getting off. In the bigger cities, though, he learns that that's a lot harder to sell. So he bends the rules a little bit, does some touching of his own. Nothing major, just a few handjobs here and there. It's not so bad. It's not that different from jerking himself off. He deals with it.
The rules get muddier the more he does it, though, and in a few years' time he's taking a finger or two in the ass for an extra twenty bucks, or using his mouth and his hand for an extra thirty. It's still just work, it doesn't mean anything, and Dean very strictly doesn't think about it after the deed is done and the money's sitting pretty in his wallet.
The first time he has sex with a man, he's twenty-three and broken down in Northern California, surrounded by redwoods and silence. He uses one of the cell phones Dad bought him to call a tow truck, knowing full well he doesn't have the funds to pay for it, and hopes against hope that he can do some work around the shop or something in exchange for the part he needs.
The guy that picks him up looks to be in his mid-thirties or so, handsome despite the dirty coveralls and the grease staining his skin. He gives Dean a look when Dean hoists himself up into the tow truck, then turns his eyes back to the road and pulls out on to the highway. "Gonna be about seventy for the tow," he says, yawning. It's late, sometime around three in the morning. "Sound of it, I'm thinking you'll need a new starter. Run you about twenty bucks, fifty for the labor."
"I can do that myself," Dean butts in.
The driver gives him an appraising look. "Uh huh," he says, disbelieving. "Well, you're free to use what you need at the shop in the morning. We'll call it an even hundred."
"Sure," Dean says, nodding. "Only I, uh. Well, I'm kind of down on my luck at the moment, and…I might not look it, but I'm one helluva mechanic. I was hoping…if you've got the work, you know, maybe I could help out around the place until you feel like we're even."
"Well," the driver says, dragging the word out and frowning, "not much work to do, if I'm honest. And I got employees, you understand." He contemplates for a moment and then steals another glance at Dean. Whatever he sees must make him bold, because he sets his gaze fixedly on the road and says, carefully, "Could be I've got some work of a different sort, if you're interested."
Dean's played this game enough times now that he knows all the rules, so he swallows back his nerves and leans forward a little, dropping his voice just enough that he could still back out if it turns out he's reading this wrong. "Yeah? I think we could work something out."
The way the man's fingers tighten on the steering wheel tells Dean he hasn't read it wrong at all. "Next truck stop sound all right to you?"
"Sounds just fine," Dean smiles, already buzzing beneath his skin.
Nothing about this hook-up goes like the ones Dean is used to. The driver- who introduces himself, with almost endearing awkwardness, as Tim- ushers Dean to the slim backseat of the truck once they're pulled over, where he insists on kissing Dean and touching him through his clothes for the better half of an hour. He pushes Dean back against the seat and covers him with his body, easing between his legs and grinding patiently, like he's in no hurry at all. It's already more than Dean usually does (he has a pretty strict no-kissing rule, and he's never had a man lie down on top of him, either) but he doesn't try to stop Tim or reroute the direction this thing seems to be taking. Maybe it's because the guy suits a type Dean tries to pretend he doesn't have (dark hair, pale eyes, stubble), or maybe it's just because he's lonely. Either way, he cants his hips upward as Tim ruts against him, surprising himself enough to make his stomach clench, but not enough to stop.
It's pretty obvious where this show's headed well before Tim breathes, "Let's get these jeans off you," but the sight of the condom and the lubricant still send a stab of panic through Dean's chest. The prep work isn't anything he's never done before (and God, it feels good, whether he wants to admit it or not), but he's still terrified when Tim works his way out of dingy gray coveralls and his underclothes, coming back to Dean in nothing but his socks.
Tim lines things up, kisses Dean deep and careful, and presses in so slow and gentle that Dean imagines he must know, must see on Dean's face that this is new and frightening territory.
"God damn," Tim gasps, once he's fully inside and Dean is wincing with the discomfort of it, "anyone ever tell you how pretty you are?"
"Just fucking move," Dean grits out, his eyes squeezed shut and his nails digging into Tim's sides.
Tim huffs a laugh and drops a kiss on Dean's collarbone. He's still gentle as he begins to pump his hips, kissing Dean's throat as he moves. Dean shifts his own hips, circles his legs around Tim's waist, and the pain transforms into something new and different, something like scratching an itch, sharp and satisfying. He doesn't even realize he's making any sounds until Tim whispers, "shh, shh."
It doesn't last long, once the actual sex starts. Tim finishes up with a groan and pulls out of Dean slow and easy, though it still makes Dean hiss and fidget, his ass uncomfortably stretched and sticky. After a short break, Tim gets Dean off with his hand- which is a kindness Dean doesn't expect- and when it's all done they half-lay, half-sit in the backseat for a moment, catching their breath. Tim gives Dean his T-shirt to clean up with, and when they feel they don't look like they've been fucking, they head to the washroom to clean up some more.
"I can put that starter in for you," Tim says, as they walk back to the truck. "It's no trouble."
Dean laughs, then bites his lip at the ache that stirs inside him. "I'm good," he insists, although he does let Tim help him back up into the truck.
On the road, Tim steals a couple of glances at Dean, then finally says, as they're pulling on to Tim's lot, "Where you staying tonight, anyway?"
"Only a couple hours til sunrise. Figured I'd catch a few in the backseat of the Impala, then get to fixing her up and get out of your hair."
Tim shakes his head. "Perfectly fine bed in the trailer, room enough for two. I don't see any sense in you sleeping in your car." He shuts off the ignition and looks at Dean seriously. "No obligation. But I'd like it, if you came in with me."
Dean should say no. He should, but he doesn't. Instead he nods and swallows. "Yeah," he says, his face warm. "Sure."
They go another round once they're in Tim's trailer, the damn thing rocking so chaotically Dean worries it might fall apart any moment, and Dean doesn't know if he's in Tim's bed because he's paying off a debt or because he wants to be. The distinction keeps him up well after Tim is softly snoring beside him, one arm draped possessively over Dean's stomach.
In the morning, Tim takes Dean to one of the local diners and buys him breakfast, then drives them (in a rust-pitted '79 Camaro, which he speaks of fondly all morning) back to the shop, where he helps Dean fix up the Impala despite Dean's protestations. It's all right, though, joking around with Tim and cracking a few beers, working with the radio up and a nice breeze rolling through the shop. It's surprisingly pleasant, even, and Dean doesn't argue when Tim suggests they change the oil and give Baby a quick tune-up, too.
It's a Sunday and they've got the shop to themselves, so they eat lunch right there amid the greasy car parts and oil stains, Tim ordering a couple of cheesesteaks and the best onion rings Dean's ever eaten. There's an awkwardness that descends after the grub is gone and they're kicking back in a couple of creaky lawn chairs, looking at the Impala and sipping beer. There's nothing left that needs doing, but there's a companionable air between them that they both seem loathe to break. Eventually, once the radio hits a commercial break, Tim clears his throat. "So," he says, fiddling with his bottle. "Where you headed, anyway?"
Dean shrugs. "East, I guess. Unless some work comes up."
"Stay," Tim says all at once. "I mean, if you don't have any good reason for going. You were right, you're a damn fine mechanic. I could make some room for you on the schedule." He pauses and then rushes onward, his eyes darting across Dean's face, trying to take in his reaction, "You could stay with me awhile, until you work up enough money to find something of your own. Or…or you could just stay. I like you, Dean. I mean that."
"I'm…" Dean stands up and shakes his head, setting his beer down and fishing his keys from his pocket. "I'm not gay, man. This is just…" He shakes his head again, his hands shaking horribly. "I'm sorry you got the wrong idea, but I'm not…"
Tim's brow is furrowed as he stands up slowly. "Did I...Look, I didn't mean to-"
"Seriously," Dean says quickly, opening the Impala's door, his heart hammering in his chest, "thank you, for…for everything, but I-I gotta go." He slips into the car and starts her up like nothing, and drives away so fast he leaves Tim behind in a cloud of dust.
X
Dean stops turning tricks entirely when Sam joins up with him again, not that he'd done it much after that incident with Tim, anyway. The worry of Sammy figuring out what his big brother does in the dark overrides the occasional grumble from his stomach, and with Sam around it's a lot easier to hustle and pickpocket like they did as kids.
One morning, after they spend the night roughing it in the Impala because they're too broke for a room, Sam turns to Dean and asks, with a laugh, "Man, how did you manage on your own for so long?"
Dean doesn't let anything show on his face, just smiles and stretches. "I got by," he says, stifling a yawn. "That's all that matters, right?"