AN: This is to be my first multi-chapter fic, I know it's been done before but the idea just wouldn't let me go. This goes AU after S.3, but there's still going to be some SPOILERS for at least S.4 and probably character spoilers for even later seasons.

Warnings: Torture, violence, death, the usual. There's also going to be slash (no wincest), some language and probably OOC:ness. Angst, bad humor and some kissing later on.

Disclaimer: I don't own them or he plot, I'm just playing with the guys and girls for my own amusement, but since the writers decided to kill some of them they're probably happier with me anyway, can't say that for Dean though...

1. In which Dean is in hell

The first thirty years were a blur, sometimes it would seem he had been there forever, that this world of screams, blood and agony was the only one he'd ever known. Other times it would feel like it was only yesterday he held his dying brother in his arms, or heard his screams as he was dragged off to hell. It was always these sad moments with Sam he remembered, moments filled with pain, as if thoughts of happiness was something impossible. Yet he always remembers his brother's name, even in the brief moments when he doesn't remember his own, he clings to that name, to Sam.

Each day he dies all over again, is ripped to shreds only to be put back together again, there is a moment each day when he isn't hurting that much, when no one is tearing and cutting at him, when he's just hanging there, alone in the darkness. Sometimes it feels like just a second, barely a heartbeat between being so thorn up there's nothing left and everything starting all over again. Other times it feels like hours, but the pain never leaves, it's simply a different kind of pain, the pain of thoughts like "I'm going to be here for all eternity" and "I'll never see him again, I'll never see anyone I ever loved ever again", all of it silent thoughts in the darkness, it almost makes him long for Alistair of Meg to come back, start the torture again, almost.

It's been almost a year when he hears her voice during one of those quiet moments, he has lost track of time, he does it all the time, it's all a blur of endless pain, but Alistair keeps reminding him how long he's been down here, always counting the days. This day is number 342, exactly.
"Dean", it says. "Dean, Dean!" It keeps repeating his name but it seems so far away that it takes a while for him to remember he should answer, when he does it's barely more than a sight.
"I'm sorry Dean, I'm sorry you had to come here, I truly am, I'm sorry he's alone up there."

The voice is familiar he realizes.
"Ruby?" Dean forces himself fully awake, as he focuses on the presence of the demon.
"Yes, I've convinced them to let me go topside, I came to tell you I'll take care of him, thought you should know that."
Dean tries do decide whatever to nod or throw some fitting insult at her, but before he comes to a conclusion she continues.
"You mustn't break Dean, no matter how hard it seems you have to quit whining and keep it together, you can't do what he asks of you."

At that he glares at her, he might be damaged, but he would never be that broken, would never take Alistair's offer. A number of replies containing the words "bitch" and "monster" runs through his mind but he doesn't seem to get his brain and mouth to work together and form a sentence.
"And you can't tell anyone I've told you this, ever." And with that she is gone and Dean can feel Alistair's presence getting closer to the room, and the torture continues.

He listens to his own broken screams when Alistair starts pulling his nails out, one by one. He twists and turns when his fingers are broken and his stomach cut open, and when he sees Meg, now Alistair's assistant, coming towards him with a bucket filled of some boiling liquid he starts to wonder if he'll really last for eternity. But when Alistair finally makes the offer he spits in his face and tell him to go to hell, before remembering why he doesn't usually say that, and he keeps doing that for the next twenty nine years.

He hangs on to the thought that Sammy is alive because of this, that it's worth it, and when Alistair offers him to get off the rack if he starts torturing souls he focuses on the disappointment he knows would be in his baby brothers eyes. He tells the demon to piss off, again and again, every day, but it's getting harder, harder to ignore the pain and the anger flowing through him, harder to remember why he refuses.

The smile of triumph on Alistair's face when he finally says yes will haunt him for eternity, to know that he lost, that this monster who he hates above all others has beaten him. Yet he does what Alistair says, he starts cutting the souls up and he finds he likes it. It's like taking revenge for everything that has been done to him and he cannot help but think that if he goes on long enough it will somehow take away the pain. It never does of course, but it eases it, when he cuts into the screaming souls, follow Alistair's instructions on how to do it, then he for a short moment forgets everything else, it's intoxicating.

Sometimes his years as Alistair's student, a position he shares with Meg by the way, seems much longer than his time on the rack. Things happen, he talks to Meg, he learns new ways to make people scream, he hears rumors from the other demons (that's right, the other demons, he's one of them now, when he looks at himself he can see it, the blackness of his soul, the light almost completely gone).

Other times it seems like it's just yesterday Alistair carved him open; it would seem you can have nightmares even in hell.

It's been almost ten years when he starts hearing whispers about the siege, angels trying to fight their way into hell, he doesn't listen, doesn't care, just keeps torturing, keeps training the hellhounds and keeps losing himself in darkness. Until Meg tells him they have come for him, the angels are there to drag him out of hell.

"Just imagine what they will do to you ones they have you. You're one of us now, Dean the demon." She smiles when she says it. Dean doesn't smile, he can definitely imagine what they will do to him, and for the first time in ten years he feels fear again. The hatred, anger and pain where always there, together with a foreign feeling (duty maybe?) that he associated with Sam, but he had forgotten what fear feels like, until now. He sits with Kira, the hellhound who killed him, when Meg shows up again, just sitting there with his bloodstained hand in the black fur and tries not to think about what it might feel like to be tortured by angels.

"I'm going topside, wanna come?"
"What?" Is the only thing he can think of saying and Meg just smiles at him.
"Yeah, Lilith has fixed an escape route, I'm supposed to help with the big plan upstairs, you want in?"
Deans first thought is that Sam is up there, he realizes he has mixed feelings about this, he wants to see him, but something tells him it wouldn't be a good idea. His second thought is that it doesn't matter, he can't stay here, he's doomed if he does.

"Yes, I'm in, what's my part?"
Meg gives him a calculation look and Dean can really see the resemblance to Azazel in that moment.
"You need to keep Sam alive until the final seal breaks."
Dean has heard about the seals of course, the looks on Lucifer's cage, but he never really thought they were real. It is however not in any way a hard command to follow, it's what his whole life has been about.
"Keep Sammy safe?" he states. "That's my part?"

"Yes, you promise to do that, you get out of the pit." There's a pause and Dean sends her a questing look.
"What's the catch?"
"You're going as one of us Dean, I hope you get that, I'm not bringing you back to life, I'm just taking you up there. What do you say, deal?"
Dean has long since came to terms with what he is, he doesn't even think of himself as human when he looks around at the dark torture chamber he lives in, there is simply one possible answer.
"Yeah."

The contract kiss is just that, all business, and Dean wonders how two beings who hates each other as much as they do can function together at all, he killed her father and brother after all.

Meg starts to walk towards the exit when Dean calls out to her.
"I'll need my body, if I am to get close to Sam."
"I'll see what I can do", she says on her way out, after two seconds she's back.
"Oh, and Dean, bring Kira! You're such a rookie, you're gonna need her."

Not even an hour later he feels a tug at his entire being and he wakes up in a small dark place, the only sounds his own desperate breathing and Kira's rushed panting.
"Good girl", he says and his voice sounds unnaturally harsh. "Let's go find Sammy."

Review, please? It would make me so happy to hear what you think. Next chapter should be up soon, as soon as I figure out how to manage chapters...