Dean/Cas. High School AU. Song: 'Grand Theft Autumn', Fallout Boy.

"You need him, I could be him / I could be an accident, but I'm still trying."

Dean Winchester was a screw up. By age 17 he'd been expelled twice, gotten into more fights than he could remember, let alone count, and on one memorable occasion wrapped his Dad's Chevy Impala around a lamppost. Pretty much the only thing he considered himself to have done right was raising Sammy (well, that, and rebuilding the Impala).

Point being, he was a screw up. Problem was, it was pretty hard to turn that around when they never stayed anywhere long enough for him to even try.

He hated every small town they moved to. They were all the same: claustrophobic, tight-knit, boring as fuck. In fact, there was only one in living memory to possess something even close to a redeeming feature, and that came in the form of the nerdy little guy with the strange name who lived next door and shared Study Hall with him.

Castiel Milton was weird.

Personal space was clearly a foreign concept. He was the smartest person besides Sam that Dean had ever come across. He could tell a joke without ever once cracking a smile – pretty much without emoting at all, ever – and he seemed entirely oblivious to the fact that both he and Dean were social outcasts. Also, he was hot – in that unassuming, totally unexpected, not-even-Dean's-type sort of way.

Sam had yet to stop laughing at the epic gay crush his rebel of a big brother had gone and gotten on the kid next door.

So yeah. Dean Winchester was a screw up and he was pretty sure Castiel Milton was out of his fucking league.

But hell – when had that ever stopped him from trying?

xxx

Team Free Will. Song: 'We're Marching On', One Republic.

"There's so many wars we've fought / There's so many things we're not / But with what we have / I promise you that / We're marching on."

So this was what it came down to.

What was it he'd called them? One ex blood junkie, one dropout with 6 bucks to his name, one holy freaking tax accountant, and now finally the archangel in witness protection. Team Free Will.

Oh yeah. This was gonna go great.

"So come on, Fearless Leader," Gabriel sniped from where he was sprawled across one of the motel beds, making a godawful mess of candy wrappers and crumbs. "What's the plan?"

Dean raised an eyebrow, regarding his so called troops.

The archangel was flipping incessantly through the few channels available on the cheap TV, seemingly for the sole purpose of annoying Sam. Even as Dean looked on, his brother made a sudden lunge for the remote, only for it to be snatched out of his reach at the last second. And right on schedule, out came the bitchface as the pair promptly devolved into whiney bickering that was honestly the most nauseating form of flirting Dean had ever had the misfortune of witnessing. And then there was Cas, right next to him and too close as usual, head cocked at a damn near painful angle as he studied the ridiculous, passive aggressive mating ritual taking place in front of them like both their brothers were some kind of rare wildlife and he was Richard fucking Attenborough. Dean almost made a joke to that effect, but snapped his mouth closed as he realised what a mistake that would be. Cas wasn't exactly a fan of pop culture references that flew over his head, especially now that Gabriel was around to emphasise his ignorance, and Dean couldn't handle another bitchy angel right now.

His mouth twitched unexpectedly, an odd rush of affection sweeping through him for all three of his stupid, clueless allies.

"Dean?"

He blinked, Sam's voice calling him back to attention. They were all staring speculatively, waiting for him to answer, probably wondering at the inappropriate and quite possibly dorky smile he was wearing.

"Plan. Uh, right..."

Gabriel stopped channel hopping long enough to roll his eyes scathingly. "Smooth, Deano. Clearly I fell in with the winning team."

Dean snorted, still idly regarding the three men around him.

Sometimes he too easily dismissed them, maybe; forgot that they weren't just a quartet of geeks, freaks and screw ups. Hell, Sammy was genuinely as smart as they came, a psychic and a telepath, as dangerous with his bare hands as with a gun, and fucking ruthless when he needed to be. Cas was a freaking rebel angel, who had, in his time, smote Alistair and outwitted Meg, had defied Heaven and killed fellow angels because Dean had said it was the right thing to do. And Gabriel – man, Gabriel was a pagan god and an archangel packed into one lethal, pintsized package.

He grinned again, clapping a puzzled Cas on the shoulder, feeling better than he had in a long time.

"Damn right."

xxx

Dean/2014!Cas. Song: 'You Found Me', The Fray.

"Lost and insecure, you found me / Lying on the floor, surrounded. / Why'd you have to wait? Where were you? / Just a little late, you found me."

"Jesus, Cas, what is all this shit?" He picked up the nearest white bottle, rattling the few remaining pills inside. The label had been torn off.

The ex-angel was stretched out on his back on the little pallet bed in the centre of the room. He shrugged languidly, movement opening the loose collar of his hippie shirt. "I don't question anything that gets the job done, Dean." He smiled, and if Dean wasn't mistaken the expression actually looked a little mean. "You taught me that."

Dean flinched slightly, catching the barb even if he had no idea what it meant. He had to look away, ended up staring despondently around the rest of Cas's room: the mess of tattered clothing, empty bottles, blasphemous iconography, weapons, drug paraphernalia, and what maybe looked like a sex toy over in the corner. Ended up flinching again.

"What the fuck happened, man?" He gestured around helplessly, unable to encompass the sheer wrongness he was surrounded by.

Castiel just tipped his head back and laughed; that vacant, unnatural, fucking heartbreaking laugh that had been jarring Dean's nerves since he'd first heard it.

"What happened? You left."

He frowned, a protest forming on his lips about how he'd seen his asshole of a future-self not five minutes ago, but Cas spoke over him.

"Sam said yes and you were gone. Checked out." He waved a dismissive hand, lip curled in what might have been disgust.

Dean flushed, oddly ashamed of something he hadn't even done yet. Not for a moment did he doubt the truth of what Cas said, though. Hell, he'd seen the emptiness in his own eyes right after his future-self had killed a guy in cold blood. 'Checked out' was one way to describe it, he supposed.

But it seemed even worse, somehow, that he could ever just stand back and let Cas become... this.

He bit his lip, damn near to pleading. "Cas, c'mon, this... this isn't you."

Castiel's mouth tipped sardonically, and he rose slowly and unsteadily to his feet, swaying for just a moment before seeming to get his balance and stepping closer. Dean wasn't expecting him to prove capable of any kind of speed after that little display, so he was completely unprepared when Cas's hand suddenly darted out to fist in his shirt and yank him forward.

He had a fleeting impression of vivid blue eyes, the only thing even remotely familiar about this Castiel, and then another mouth was pressed forcefully against his own, lips rough and chapped, tasting of alcohol and bitter pills and other things Dean wasn't sure he wanted to know about.

It didn't last long. He jerked away in astonishment, entire body gone rigid. He was kinda used to Cas's troubled relationship with personal space by this point, but this – him and Cas didn't do stuff like this.

The virtual stranger in front of him gave that nasty smile again, reaching up to pat his cheek. "You're too late, Dean, but it's nice of you to try." He sidestepped, heading for the door. "I always did like past-you better."

xxx

Sam/Dean. Death fic. Song: 'Into the Dark', Death Cab For Cutie.

"If Heaven and Hell decide that they both are satisfied / Illuminate the no's on their vacancy signs / If there's no one beside you when your soul embarks / Then I'll follow you into the dark."

"We did enough, right? To g-get in?"

Sam was bleeding out, right in front of him, and he couldn't stop it. No more deals to be made, no more angels to yank them in and out of the afterlife, no more cheats. They'd run out of luck, out of lives, and this was nowhere near the blaze of glory he'd had in mind. He'd always sort of thought that when they went out for the last time, it'd be together. Not this: Sam lying in a pool of his own blood, Dean frantically trying to stem the hot flood of it while his stupid little brother just went on talking.

"Heaven... Heaven'll take me now, right? After everything?"

Dean wanted desperately to shake him, but settled for snarling furiously, "Shut the fuck up, Sam." This wasn't working. There was too much damage. He couldn't stop it. Tears of bitter failure stinging his eyes, he moved instead to lean over his brother, faces mere inches apart so that Sam couldn't possibly mistake his words or expression.

"Listen. Don't... don't you go anywhere without me, Sammy, don't you dare. Wait for me, okay?"

"Dean –"

He kissed him, hard, to silence the anxious protest, tasting blood on Sam's lips. Lifeblood. Pulling back, he bared his teeth in a pained, vicious smile. Hissed out, "Screw Heaven. Screw God, screw the angels, fucking dicks with wings..."

His brother tried to laugh automatically, blood spilling from his mouth and catching in his lungs, spattering faintly against Dean's cheek. "...Better than the alternative," he managed to gurgle after a few seconds.

Dean snorted dismissively. "Yeah, well screw Hell too. We're done with the whole cosmic chess game. We'll find something else."

"I don't think –"

"Promise. Just you and me, Sammy. Into the dark."

Sam half-smiled, bloodied and beautiful, and Dean had always known something worth dying for when he saw it.

He kissed him again, salt and copper, and didn't let himself open his eyes when he couldn't feel Sam's breath against his mouth anymore. His hand closed around the gun at his belt.

They were fucking meant to go out together.