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The first time Dean has a drink, he’s eleven. He’s eleven, and he’s just back from his first hunt with Dad, the first where he was more than just bait, a gnarly scratch down his left arm where the ghost they were hunting threw him against an exposed nail on the floor. It was a simple salt-and-burn, and Dean had no business getting hurt, Dad tells him, before passing him a glass full of the amber liquid he drinks every night and, sometimes, in the mornings. It burns in his throat, and Dean hates it, but he doesn’t say so when Dad asks how he likes the whiskey—Dean has disappointed him enough for the night, so instead he nods and takes another sip.
After that, alcohol makes more appearances. A sip or two of Dad’s beer to celebrate after a hunt gone well, that eventually become Dean’s own bottle, because he’s 14 now and he’s old enough for that. The whiskey when he gets hurt on a hunt continues, and occasionally there’s a clear liquid that tastes even worse, instead. Dad calls it vodka and he uses it on Dean’s wounds too. It’s a good disinfectant, he says. Dean mentions all of this once at school, and most of the boys in his class think his dad is cool. Dean agrees—Dad is hunting the things that go bump in the night to save all of them. He doesn’t say that, of course. He had once, years ago, and everyone made fun of him. When Dean goes home and tells Dad what his friends had said, Dad isn’t happy like Dean thought he would be. Instead, he sends Dean to bed without dinner with a warning to never talk about their personal lives to anyone, or else. Dean doesn’t want to find out what the “or else” entails, so he turns to just making shallow jokes at school.
Sammy doesn’t get any whiskey when he’s hurt, but then again, Sammy never gets hurt that badly. Dad or Dean are always standing right in front of him when there’s trouble but, most of the time, they make sure the trouble doesn’t get to Sam. If Sam does get hurt, be it a scrape when he falls in the park Dean takes him to almost every day after school, or a scratch when Dean fails to protect him fully during the few hunts his younger brother is allowed on, Dean has instructions to use one of the disinfectant wipes in the first aid kit to clean the wound. They never have a lot of those, so Dean saves them for when Sam needs them, and just fishes the vodka out of his father’s duffel bag to tend to his own wounds.
Dean is also eleven the first time he seriously messes up during a hunt. The shtriga almost gets Sammy, and Dean has never seen Dad so mad. Dean understands; he’s also never been this mad at himself. Sam is his responsibility, and he could be dead right now if it wasn’t for Dad coming back at the right moment. Dean had just wanted to leave for a moment, just to breathe a different air from the one he had been sharing with his little brother for the past three days. But if there’s something both older Winchesters know well is that it only takes a minute: even falling asleep at the wrong time can be dangerous. For days afterwards, even after they leave that godforsaken town, Dean doesn’t let Sammy out of his sight for even a minute — you never know what’s crawling in the night.
The next time he messes up like that, Dean is sixteen. Sammy has just turned thirteen and is starting to protest being called Sammy. Dean has barely stepped foot in their motel room, and he immediately knows something is wrong. It might be because most of Sam’s stuff isn’t visible when he usually leaves a trail of clothes everywhere; Dean thinks he does it purposefully to annoy Dad — it works unsurprisingly well, and usually backfires on Dean. It might be because Sam doesn’t immediately bolt for the shower as he does whenever Dean comes home from hustling pool or whatever odd job he has managed to get for the day — Dean swears Sam is just waiting for him to step through the door to occupy the bathroom for a half hour. Or maybe it’s just because, after twelve years living in each other’s pockets, Dean has become so attuned to his brother’s presence that he feels it like a physical ache when he’s gone. Regardless of the reason, Dean knows Sam isn’t in the room even though he’s still standing by the door. In a second, he’s turning around and running to the reception desk, frantically asking the clerk if she’s seen his kid brother. When she says she hasn’t seen anyone that fits his description since she started her shift three hours ago, Dean almost breaks down crying.
In the week that follows, Dean doesn’t sleep, and he barely eats. He calls Dad at least a hundred times, but he never picks up and eventually Dean gives up. He searches the entire town and describes Sam to everyone he sees. He steals a car and does the same in the towns nearby. Sammy is nowhere to be found. When Dad comes home, he reacts as expected, and Dean’s cheek is still slightly red when they finally find Sam.
He’s fourteen when he gets his first handjob, a hurried thing in Carla Mulvaney’s poorly lit basement, striving to be completely quiet so her dad wouldn’t hear them in the room above. The first time he’s paid to get one, he’s sixteen. He doesn’t have to be particularly quiet in the dirty alleyway behind the club, but he also has no urge to make any sound that isn’t usually accompanied by tears, so he remains silent. After a while, he learns that the men are more likely to come back another day if he pretends to enjoy it, so he saves his voice for the johns and goes quiet in his daily life. Dad is never home, and when he is he doesn’t notice; and Sam is just relieved he’s quit his nagging over where he goes when he’s not home.
He’s dropped out at this point, and he doesn’t need to speak much to hustle pool, or to do whatever odd job in a garage he’s managed to find in whichever town they’re passing through. Dad tells him to find a real job if he’s not gonna be studying, but no-one wants to hire the guy who can’t guarantee if he’s staying even for two weeks. His trysts in club bathrooms, dirty alleyways and only slightly less dirty pay-by-the-hour motel rooms pay enough to keep food on the table while Dad is out, at least for Sammy whose growing body inhales enough food to feed a battalion.
Dean finds he can ask for more money if he plays up his youth and innocence, and that the thinner he is, the younger he looks, so he eats only enough to keep up with Dad on the hunts he takes Dean on. He leans against bar counters, nursing a fruity drink and looking coyly up through his lashes at the men who sit next to him and offer him a drink and fifty bucks for his services. He’s not offended anymore when they assume that’s what he’s there for — he’s self-aware enough to know what he looks like and numb enough not to care.
He’s eighteen the first time Sam announces, with all the certainty and straightforwardness only a fourteen-year-old still possesses, that he’s leaving as soon as he turns eighteen, because he doesn’t want to live like his older brother. Dean refrains from telling him he doesn’t know the half of it and puts Sam’s plate of spaghetti bolognese in front of him, dishing only a few spoonfuls for himself. He waits until Sammy is asleep in the room before getting dressed and sneaking out the door. They are renting a one-bedroom this time, since there have been several ghost sightings in nearby towns and Dad figured they might as well stay put until Sam finishes the school year in a couple of months, which means they have a real kitchen, and Dean can give Sammy some real food instead of diner meals and canned crap. It also means Dean doesn’t get a bed, but you win some, you lose some, and it’s not like Dean sleeps much these days. He’s still thinking about what Sam said when he gets to that night’s club, and it’s on his mind all throughout the process of negotiating with a john that will pay more if he pretends to be his son. Dean weighs the deep disgust the mere thought gives him against the meagre salary he gets as a mechanic and decides to suck it up and deal.
Sex is synonymous with gravel under his knees and cement against his back until Cassie, the first person he tries to talk to about his real job since that one time in primary school that branded him a liar for the couple weeks they stayed in that town. She calls him insane and throws him out of the house, stops picking up the phone when he tries to call to offer to show her any type of proof she needs to believe him. From then on, he refrains from having anything that even resembles a meaningful relationship, resigning himself to the johns and the girls he picks up on what he comes to consider his days off. He takes the playful ribbing from Dad and Sam’s reproachful looks when he comes home smelling like sex almost every night, ignoring the twinge in his chest every time they mention it.
They keep changing towns, and Sammy keeps growing, but both John and the johns remain the same. Dean steadfastly refuses to believe Sam when he says he’s leaving for college, year after year, even when he sees the application letters his brother tries to hide from him, like they’re a normal family, in which the word privacy still means something, like they haven’t shared duffel bags, and motel rooms and beds since Sam was still in diapers. Sometimes Dean goes on hunts with Dad, and sometimes he stays back with Sam, but his favourite times are the school breaks, when the three of them pile into the Impala and go after whatever the monster of the week is. That’s when he feels alive, with Sammy at his back and Dad calling the shots, and even the ever-present fights between his brother and his father bother him less then.
The last time Sam mentions leaving, he has a letter of admission to Stanford in his hand. Dad forbids him from leaving, and Dean is powerless to do anything but watch it go down and eventually get between them when the argument seems about to come to blows. Turns out no amount of denial can make time turn back on its heels to when Sammy was the little kid who wanted to be just like his older brother. That night is the first time Dean prays since he last heard Mom say angels were watching over him. Everyone is devout when their world is falling apart, he thinks, as he begs to whoever is listening upstairs that he gets to keep his family together. No-one answers and, in a cold night just like any other except for all the reasons why it’s different, Sam leaves and takes what little was left of the warmth in Dean’s heart. Years later, when an angel tells him he has no faith, Dean can pinpoint the exact moment he stopped believing, as he watched a bus take a left and disappear, eyes prickling, a lonely tear sliding down his cheek.