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The news of Dean Winchester’s arrival in Hell travel fast, faster than almost any other news since those amusing crusades went out of fashion.

And how could they not? Many here remember John Winchester and they know, from those that went Above, that his oldest son surpasses him. The one who slew Azazel, the brother of the Chosen. No human has killed as many critters as Dean, has sent as many demons back to their caves. No human has stared into the abyss this long and somehow managed to stop it staring back.

A pure soul, a righteous man in hell. Yes, news travels past. Lilith’s new pet has arrived. And he screams so beautifully.

At first, Alastair shrugs and goes back to work. What’s another screaming, gibbering heap of human waste? All the same, all so easy. None of them present a challenge. These days everyone lands in hell, all the sinners and no saints, all average, boring, lying, thieving, cheating humans. It’s like Heaven went out of style and, personally, Alastair is pretty sure Eden’s kinda empty. There’s no souls left for the Great Above.

They all hang around here.

Hang. Eugh. Even his puns grow average. Hell has grown boring to Alastair and though he loves the place itself, his projects annoy him terribly.

He dismisses Dean Winchester.

Dismisses him right up until the moment Lilith comes storming into his workroom, huffing and puffing like those little meatsuits she prefers when she goes Above, screaming about that damn soul who just won’t break.

That’s five years after the news of the Winchester son’s arrival first stirred up the realm and Alastair raises one pale shadow eyebrow. Five years? Maybe there’s something to the hype after all.

When Lilith throws a tantrum that can be heard across several circles and orders him to go and break that little snot, he doesn’t protest too much. A demon’s got to get his kicks somewhere.


Alastair enters the room where the man is tied up and has to admit that he’s something to look at. Pretty little thing, painted in red and black, blood and bruises. Lips split, eyes like the Pit, chest heaving from pain and exhaustion. Quite the picture, young Dean makes.

Lilith stands behind Alastair, bitching and yelling and he can see the defiance, the amusement glinting in Dean’s gaze. He likes pissing Hell’s regent off. So Alastair gently but firmly kicks her out, closes the door and turns to the boy with a grin that’s all teeth.

He holds up his razor for inspection, receives a bored look in return and almost feels something like giddiness rise in him. Not only pretty but defiant.

It’s better than he’s head in several millennia.

He steps up to the rack, closes in until they are chest to chest and leans forward, licking blood from Dean’s chin. “An offer, Darling, before we start playing. I’ll let you off the rack, if you say so. One word, one tiny little word. Just say yes and there’ll be no more pain. For you anyway.”

He pulls back enough to grin at his new toy and receives a bland look in return. “Join your team? Play your game?” Dean asks, his voice rough and deep, pain and the memory of meat-sex. Alastair almost purrs.


Instead of a verbal answer, the tortured soul licks his lips and then spits in Alastair’s face. Or rather, what passes for a face. Hell is all about self image and imagination. You look the way you want to look. It’s how Lilith keeps the illusion of her little meatsuits, the reason why all those tortured souls look like little more than meat.

No imagination, the sinners of this age.

Alastair’s definition of self is mostly made up of hands and teeth, claws, a tongue and a dick. What does he need a face for?

Dean wears jeans and boots and a t-shirt, not naked like most others and he grins crazily and spits the High Inquisitor of Hell in the face.

Alastair has a new hobby.


Every day, or what passes for day in Hell, Alastair returns to Dean’s little home away from home and leans close, licking blood and asking the same question.

“Do you want off?”

The second time he asks, Dean spits again.

The third, Alastair makes sure the boy has no drop of liquid left in him to spare and Dean rasps in that voice of his, “I’d rather go to hell. Oh, wait, I already did.”

He laughs at his own joke until he has to start screaming.

The fourth time, he merely cocks his head to one side and blinks, very slowly.

The fifth time he cusses, the sixth he sings, the seventh he questions Alastair’s heritage and the eighth he asks for a beer.

After that, he just laughs.

He laughs and laughs and laughs and he never stops until Alastair makes him with his razor. They say that everyone in Hell gets tortured but it’s been centuries since anyone’s laid a hand on Alastair. But Dean’s laughter, his mocking green eyes and tilted head, they are a torture of their own. They speak of something Alastair wants but cannot have and it makes him angry.

Makes him very, very angry.

He gets creative when he’s angry.


Five years later, Dean still laughs and whispers start to follow Alastair around, wondering if he’s lost his touch. He rips a few limbs off, restoring his reputation, but the question remains.

Why the hell can’t he break Dean Winchester?


Twenty years and still he laughs.


Thirty years in hell, twenty-five with Alastair’s gentle and loving touch all over his soul and body and mind.

And only then does he think to ask the man the most important question.

“Do you want off?” He asks as always, and as always Dean laughs.

And right into the laughter, Alastair asks, “Why?”

Dean’s mouth clicks shut audibly, the silence after his scorn almost deafening. Beyond their little playground, lost souls howl and Hell keeps turning. Dean lets his head drop to his chest, looks up at his torturer through sooty, sticky lashes, eyes burning green and cold and crazy as diamonds.

Alastair holds in breath he doesn’t need, stills the smoky tendrils of his being and waits, waits for the soul before him to speak.

Finally, after an eternity, Dean repeats, eyebrows raised, “Why?”

He turns to the side to spit a glob of blood on the dirt floor and tilts his head to look at Alastair sideways.

“Why not?”

Bastard goes right back to laughing.


Question: Why can’t Alastair break Dean Winchester?

Answer: He’s already fucking broken.


And Alastair stands there for a moment, stock still, blank with epiphany before he throws his head back and joins Dean’s howling laughter.

Oh, oh, rumors were right, the hype was right and Lilith was wrong.

Dean Winchester is absolutely glorious, a broken thing shaped like a man, broken beyond breaking, laughing for twenty odd years simply because there’s no reason not to.

He’s stared into the abyss the night his Mommy burned and it didn’t just stare back, in climbed inside of him, filled him up with yawning emptiness that never went away.


Why not?

And yes, yes, oh yes, Alastair has found himself a new playmate.

He puts aside his razor, reaches for the chains and leather that bind Dean to the rack, loosens them until he slips free, drops to his knees and moves on his own for the first time in thirty years.

He coughs, spits, rubs at his chest with both hands, traces the lines of his face like he’s forgotten them. He‘s still wearing his armor of mortal garment, still dressed like he was in life, his image of self stronger than that of some demons and he takes only a beat or two to sort himself out at Alastair’s feet.

Then he looks up at the demon, up and up and asks, one hand at his throat, “Why?”

Why’d he let him loose? He still hasn’t said yes.

Alastair snorts and runs his split tongue over wicked teeth. “Why not?” he asks right back and holds out his razor in offering.

Dean hasn’t said yes. But he never said no either.

He hesitates, quirks a grin, and takes the blade.