A/N: Hi, guys! First of all, I'd like to give a big thank you to my best friend, Prerana (Keena Wedric-Ames on Wattpad, guys!), and my wonderful editor, resrie71, for looking over this story and offering feedback. This story wouldn't have been possible without you two :)

This story is a character study on Dean that will explore his issues with self-love, sexuality, and individuality. The first three or so chapters will detail Dean's childhood (his age will be indicated in Italics at the start of each new section) and then it'll jump right into Season five, where the boys first meet Cas. From that point, the focus will primarily be on Dean and Cas's relationship, both as friends and as romantic partners.

Trigger Warnings:

Underage prostitution

Brief mentions of thoughts of self-harm

Homophobic language/Bi-erasure

Physical Abuse

I've always considered Dean such an interesting, complex, heart-breaking character, so I can't wait to start exploring the nuances of his actions, thoughts, and emotions. Thank you all in advance for embarking on this journey with me. :)

Enjoy!


Fourteen

.

It's the middle of winter and Dean and Sam are alone in their hotel room. They've just finished their last package of saltines, they're out of cash, and Dad said he'd be back two days ago, but he hasn't picked up his phone in a week. Sam is wrapped in blankets on the room's creaky mattress, looking small and tired while he bites the inside of his cheek and stares drowsily at the wall.

"Sammy?" Dean says, dropping a hand onto his arm. "You good?"

"Yeah," Sam mumbles, nodding his head loosely. His eyelids droop downward and he shivers beneath the thin sheets. "Just hungry."

The last time they ate a full meal was three days ago. Dean throws his arm over Sam's skinny shoulders and pulls him close against his side. Terrified and at a loss for what to do, Dean stares unseeingly at the space above Sam's head. "You're gonna be okay, Sammy," he mumbles into his brother's hair. "You're gonna be fine."

Dean knows they need food and money. If he had a choice between one and the other, he'd choose money, because as starved as the two of them are, sitting outside on a park bench in the middle of winter would be ten times worse. They need to stay in this room, and to stay in this room, they need cash. And to get cash—well, his options are limited, and none sit well with him. He could steal someone's wallet, but Dean isn't all that sly and he can't risk getting thrown in jail and leaving Sam all by himself. He could probably beg for money on a corner somewhere, but this is a poor town with little to spare and it's nearly one in the morning anyway, so the streets are empty. If they owned anything of value, he'd pawn it, but as it stands, the only things they have are a couple of guns and Mary's ring, the latter of which Dean would never sell, and the former of which would definitely stir suspicions, as Dean is still a minor. The only thing he has left to offer are the clothes on his back and—himself.

It's when the motel owner comes pounding at their door shouting that he'll kick them out if they don't pay by tomorrow morning that Dean truly realizes how doomed things are. They've been through bad spots before, but nothing like this.

Dad doesn't answer his phone the twenty-sixth time Dean calls him. Voicemail, voicemail, voicemail. The discarded box of saltines sits on the floor, barren and mocking. Sam keeps shivering and sniffling beneath his arm. Dean's empty wallet gapes at him from the nightstand. The owner's thundering voice echoes in his mind. Cold, sickly dread unfurls in his stomach like poison. The decision looms over his head like fog.

"Sammy," Dean says, "I'll be back, okay?"

Then he pulls on his jacket and stumbles out into the cold, ready to do just about anything for a couple of bucks.

The bar is loud and sour-smelling. He's surrounded by drunk women, truck drivers, seedy men, and depressed alcoholics. He's fourteen and scared and sticking out like a sore thumb.

After being there for less than twenty minutes, a man his dad's age eyes him from across the room and beckons Dean over. His teeth look too white and his eyes are so brown they look black.

When Dean nervously sidles up beside him, the man leers down at Dean like he's a piece of meat. The words spill from his lips like slime. "And what's your name?"

The guy's car smells like booze and cigarettes. There's a pile of fast food wrappers strewn about the backseat. A postcard from Texas juts out of the half-open glove compartment. Two crushed beer cans teeter on the dashboard alongside a pile of loose change.

The reality of what Dean is doing doesn't sink in until he hears the car door click shut behind him and the man starts shedding his coat. The leather creaks as he pushes Dean onto his back and crawls over him, his hungry, dark eyes glinting in the moonlight like gunmetal. He grins and his teeth look sharp and predatory. "Pretty one, aren't you?"

The sound of his zipper is impossibly loud in the silent car. He tugs Dean's shorts down to his ankles in one rough pull.

"You ready?" the man purrs. It isn't a question. Suddenly, rough hands are everywhere, touching, prodding, grabbing, ruining him. The man grins and undoes his belt. "Here we go, sugar."

Startled, Dean gasps in pain. God, it hurts it hurts it hurts it-

"Ah…fuck. Yeah, that's good, angel."

Dean can't think, can't speak. His senses are drowned by the sour smell of liquor, the burgundy color of the backs of his eyelids, and the terrible, burning ache spreading low in his body like fire. His head thuds rhythmically against the car door as the man pounds into him, hard enough to guarantee he'll be limping later. He grips Dean's hips with bruising force.

"Ah…ah…that's right, take it, yeah."

He can't breathe and can't think and the guy just keeps grunting and calling him sweetheart and Dean would give anything in the entire world to just fucking die already.

Afterwards, Dean can't bring himself to think about what he's done—can't force himself to relive that pain and hatred and sour twist of lost innocence—so he just takes his money, runs to the 24-hour truck stop, buys all the food a twenty-dollar bill will get him, and rushes back to Sam. On the way to their room, he drops some money on the check-in counter and wins them another night in shelter.

"Dean," Sam says in awe, his eyes widened at the pile of food Dean unloads onto the bed. "Where did you get this stuff?"

He says the line he's been rehearsing all night. "Begged on a corner till some old lady gave me cash."

"Really?" Sam says, around a mouthful of granola bar. "That's all you had to do?"

He doesn't meet Sam's eyes. "Yep."

"Maybe I should try that sometime then."

"No," Dean snaps, whipping his head up to stare at Sam. "You don't ever worry about earning money, you got that?"

Sam frowns, the Nature Valley bar frozen by his mouth. "Why?"

Dean's hands start shaking, so he hides them in his jacket pockets. "Because that ain't something you need to worry about, alright? That's on me."

"What about Dad? When is he coming back?"

Dean clenches his jaw and looks away. He'd like to know the answer to that question too. "I don't know, Sammy. I guess when he's finished with the hunt." He sits down next to Sam and unwraps a fruit pie with his shaking fingers. He tries to smile reassuringly. "Until then, I'm gonna take care of us."

Dad comes back a day and a half later. He doesn't apologize for leaving them high and dry, he just knocks back a beer, ruffles Sam's hair, and asks Dean his usual post-hunt question.

"You take care of Sam, Dean?"

"Yes, sir."

In no time, it's back to the usual routine—drive, hunt, sleep, repeat. Sam more or less forgets what happened, the earth keeps turning, and John never bothers noticing that Dean can no longer look him in the eyes.


Fifteen

.

It's the middle of December, and the thin, worn-out old hoodie Sam's had for three years isn't gonna cut it anymore.

"Dad," Dean says, once Sam's left the motel to do research at the library. "Sam needs a new jacket."

John looks up at him tiredly, his left cheek smudged with ink from the broken pen he's been using to annotate a book on werewolf lore. His eyes are red-rimmed from this morning's hangover, and the difficulty of this month's case clearly hasn't helped anything. "What's wrong with the one he has?"

"It's old and thin. He keeps telling me it's fine, but I tried it on yesterday and it feels like tissue paper."

"If Sammy says it's fine, then it's fine, Dean," John says dismissively. "And if it's that big of a deal, let him wear yours."

"I do. But mine's just as bad, so it doesn't really make a difference."

"Well, what the hell do you want me to do about it, Dean? Knit you a new one myself?"

Dean forces himself to stand his ground. "I just need a little money. I'll find one real cheap, I promise. I'm just worried that he's gonna catch a cold or something, and it might turn into pneumonia—"

"Wait a minute," John interrupts. "You want to go shopping? We're in the middle of the biggest damn case in months, and you're asking me about money?" He laughs in disbelief and shakes his head. "Can't believe your nerve, boy."

"Dad—"

"If you need it so bad, go shark pool. I showed you how to, didn't I?"

"Yeah," Dean mutters. It's true, John did show him, but he's nowhere near as good as his father and he almost always ends up losing money rather than gaining it. "But why can't I just use the credit cards? I won't spend a lot, I promise."

"The IRS has been watching our asses since Ohio. We need to keep a low profile, so we can't go off on spending sprees in every town we touch, just because you wanna buy new digs."

"Dad, it's not about buying new—"

"I'm done talking about this, Dean," John says with finality, picking his pen back up and resuming his reading. "Now, why don't you make yourself useful and start cleaning those guns."

"I'm gonna go shoot some pool," Dean tells Sam three nights later as he pulls on his jacket and grabs his keys. "Don't wait up, okay?"

Sam looks up from his battered copy of The Half-Blood Prince and nods. His bangs are hanging in front of his eyes and he's wearing one of Dean's old ACDC t-shirts with the hem tucked into his pajama pants. It's three sizes too big and his skinny frame is practically swimming in the extra material. Dean can't help the jolt of fondness he feels at the sight.

"Don't go to bed too late, alright, Sammy?"

"Okay, Dean," Sam says, and goes back to reading.

His target is a lanky, oily-haired guy who's playing pool on the other end of the bar. He's probably in his forties. Dean catches his eye and winks, and in an instant, the man's at his side, buying him a drink.

"I'm Steve," he tells Dean. "What's your name?"

Dean slides closer and offers a coy smile. He feels disgusting. "Whatever you want it to be."

The man eyes him predatorily. "You interested in a date, sweetheart?"

Dean takes his cue and bats his eyes. "Fifty?" he ventures sweetly.

Steve grins. "My rig's out back."

...

Afterward, Dean stumbles out of the truck, half dressed, with his boots in his hands and fifty bucks shoved crudely into his shorts. His partially buttoned shirt hangs off his bare shoulder and his hair sticks up in odd places. As he crosses the parking lot, someone calls him a whore.

When he gets back to the motel, everyone is asleep. On autopilot, he tucks the money into his duffle bag, kisses Sam's forehead goodnight, places a glass of water and aspirin by Dad's bed for tomorrow's hangover, and locks himself in the bathroom.

Dean climbs into the shower and scrubs his skin till it's raw, then cries until he feels like vomiting.

The next morning, when John's out hunting for booze, Dean walks Sam to the Walmart down the street and buys him a new winter jacket, a pair of mittens, and three wool scarves.

"Dean," Sam says in amazement, when they're on their way back to the motel. "Where did you get the money for all this?"

Dean forces a smirk and heaves the bag casually over his shoulder, as if he goes shopping like this all the time. "Told you I was gonna shoot some pool, didn't I? Turns out I'm pretty damn good at it."

Without warning, Sam stops him on the sidewalk and tackles him in a hug. Into Dean's chest, he says, "You're the best, Dean." His arms are wound so tightly around Dean's waist that Dean can barely breathe, but it's a good feeling.

Smiling, Dean settles into the embrace and ruffles up Sam's hair with his free hand. "Anything for you, Sammy."


Sixteen

.

Sam and Dad never get along. They're always at each other's throats about something or another, and right now it's the fact that Sam would rather go the seventh grade dance than their witch stakeout.

"I already told you the answer, Sam," John says flatly, from behind the Galena Gazette. His reading glasses are perched on his nose and his index finger is carefully tracing the lines of this month's obituary column. "No means no."

"Dad," Sam pleads, still holding the bright pink flyer with School Jamboree! written across the top in bubble letters. "All my friends are going and I promised Sandra I'd take her. Besides, all you and Dean are gonna do is stake out the witch's lair and look for charms, so it's not like I'll be missing much."

"You won't be missing much?" John repeats, lowering the paper. He takes off his glasses and rubs a hand over his face, indicating that what's about to come next is going to be a long, reprimanding lecture. "Tell me, Sam, what's more important to you: dancing around in your school gym for two hours, or saving the lives of every man, woman, and child in this town? Would you rather drink punch and talk with your little friends, or take down a group of monsters that could wipe this town out like a grease smudge? Is this jamboree so goddamn important that you'd risk the possibility of your brother or me getting killed because you weren't there for backup? Is it really that important, Sam? Because if it is, then by all means, put on your best jeans and go." He picks the paper back up and straightens it out, his eyes returning to the article he left off on. "If it isn't, however, then I suggest you iron that frown out of your face and help your brother pack the trunk, because we're leaving in a half hour."

As it turns out, the stakeout was as uneventful as Sam predicted. Dean is tempted to jokingly give Sam props for calling it, but when he wakes up and sees that Sam has dejectedly buried himself under a pile of his blankets the next morning, he decides he'd better not. John heads out at the crack of dawn to 'talk to a man about a hex', so it's just the two of them.

"You want something to eat, Sammy?" Dean asks, prodding the lump under Sam's sheets. Sam just groans in response and refuses to roll over, so Dean takes the hint and heads to the Gas N' Sip on the corner for their breakfast.

In an effort to cheer Sam up, he adds a National Geographic magazine to his basket of off-brand Cheerios and bottled water. He pays with last weekend's cash (back alley, thirty bucks for a quick blow) and then walks straight back to their room to wake Sam up.

A terrible, inexplicable sinking feeling fills him the moment he returns to their motel. Immediately, without any real evidence, he knows something is wrong. He knocks on the door and it creaks open, unlocked. He steps into the room and sees Sam isn't in his bed.

"Sammy?" he calls, panic twisting in his throat. When no one answers, he drops the groceries and darts to the bathroom, the only other place Sam could possibly be.

Sam isn't there.

A hundred bucks are gone from their stash and Sam's duffle bag is missing.

Dread sinks in Dean's gut like a stone.

When John comes in sometime around midnight, Sam's still gone.

After Dean tells him, John paces for five minutes straight, clenching and unclenching his fists. Finally, he turns to Dean with a cold, furious look on his face. "What the hell have I always told you?"

"I know, always take care of Sa—"

"Shut the hell up with that," John barks. "Clearly you don't know, otherwise Sam would still be here right now."

Dean's throat aches. "Dad, I'm sorry, I didn't mean to, I just—"

John looks at him harshly. "You didn't mean to, Dean? What the fuck is that worth? Your brother's gone and you're fucking sorry? You think that's gonna change anything?"

Part of him wants to say it's John's fault for upsetting Sam and treating him like crap in the first place, but a bigger part of Dean can't help but take full responsibility for letting Sam leave on his watch.

"Dad," he pleads, his eyes stinging.

"Sir," John corrects grimly. He shifts his jaw and turns away. "You know what? Don't bother looking me in the eye until you find Sam."

Dean swallows down the ache in his chest and bows his head. "Yes, sir."

Every night, he goes to bed thinking about Sam. Sweet, smart, good-hearted Sam with his bright future and his big smile. His floppy bangs that he could never keep out of his eyes. His stack of Harry Potter books that he marked up with post-its and highlighter. His perpetually untied shoelaces.

If he's dead, Dean's climbing into his grave and joining him.

When he finally finds Sam two weeks later, he's in Flagstaff, sitting on a patch of grass in front of an old shack, playing with a stray dog.

Thank fucking god. Dean screeches the Impala to a halt and jumps out of the car with his heart in his throat and his hands shaking.

"Hey, Dean!" Sam says, waving. He grins and pets the animal beside him. "His name's Bones. I taught him how to shake and fetch and—"

Dean grabs Sam mid-sentence and pulls him into a suffocating hug. "Don't you ever do that again, you dumbass," Dean growls, clutching Sam protectively in his arms. "I thought you were dead."

Sam looks confused when he pulls away. "Why?"

"Because you just up and left, Sam!" Dean cries. "And you didn't even leave a fucking note. You didn't even call. I've spent the past two fucking weeks imagining every possible way something sneaked in and grabbed you. I thought you were dust, man."

"Oh."

Dean shakes his head. "Get your stuff, we're going."

Sam looks back at the dog. "Can I bring—"

"No."

They don't talk much on the road.

"You and dad must've been on a pretty big hunt," Sam says into the silence.

Dean casts him a sideways look. "What makes you say that?"

"You're all banged up," Sam replies, staring at Dean's profile. "Black eye, bruises all over your arms. What was it?"

Punishment for not keeping an eye on you, Dean thinks to himself.

"Nasty skinwalker who put up a fight," he says instead, keeping his eyes on the road. "Don't worry about it."


A/N: Thank you so much for reading, everyone! Please let me know what you think in the comments, your feedback is food for my writer soul! The next chapter will be up by next Saturday, so make sure to sub/follow!

Until next time, darlings!