Disclaimer: I do not own Supernatural.

Warning: language and mentions of torture.

-KANSAS99

Chapter 8- Alastair

Alastair saw it when Dean is torturing him.

Dean even scares him a little when he walks in, but he keeps on his poker face, watching as the man he killed over and over again for 30 years wheel a cart into the dark room. He hates angels. But instead of showing his fear, Alastair sings a little song; it makes him feel a little better. He has nothing to be afraid of, he says to himself. It's just Dean Winchester, he can't do anything.

Alastair chuckled when Dean takes the cloth off the cart, his face blank. "I'm sorry. This is a very serious, very emotional situation for you. I shouldn't laugh, but I mean, are they serious?" Dean gives him a look; Alastair swears he heard screams from Hell in those eyes. "You? Torturing me?"

But he does. Dean nearly breaks Alastair in 2 hours. It makes Alastair ashamed of himself until he sees that the devils trap is damaged. Alastair smirks and gets out of his chains when Dean's back is turned.

The look on Dean's face when he see's him stood behind him is priceless. It makes Alastair grin and enjoy it even more when he punches Dean in the face, so many beautiful memories of torturing Dean flash before him.

That little bastard took 30 years to break.

At first, Alastair thought that he'd lost his touch; he couldn't get any of the Winchesters to break, and it was a pain in his ass.

Alastair remembers exactly what made Dean break. He had cut his stomach open already, his intestines half in, half out of this stomach and blood pouring out. And he was going easy on Dean today.

"We're gonna make Sammy one of us, Dean. When we're though with that little leach, he's not even going to be able to remember what being human was like. You should have listened to your Daddy, Winchester. You can never safe your brother now, because you're dead…" Alastair had said while he walked around the man gasping in pain. Alastair had shrugged and clicked his fingers, now Dean was a good as new.

"When I get out of here, I'm going to kill you." Dean said his pants fast and erratic. "I have saved Sam, he will never be one of you. He's never going to be a demon scum."

Alastair smirks. "Are you so sure about that?" He asks. But Dean doesn't reply. "Say yes, Dean. Take the knife and it can be all over. No more cutting. No more pain. No more protecting little Sammy. You can be your own person. You can do what you want. You don't have to take orders."

Dean is silent before he looks up with tears in his eyes. Alastair can see the pain there, he can see how tired Dean is and he loves it. Basks in the pain, blood and death. Dean hangs his head low, a signal of defeat. "Yes."

Alastair was about to finish the job he started, killing Dean Winchester with his bare hands. Be like he said. He hates angels. And when he thinks he can hate nothing else more, Sam Winchester walks in the room before he can rid of Castiel.

Sam doesn't see that Dean opened his eyes in semi-conciseness to see his brother holding a demon to the wall with his own powers. Sam doesn't see the defeated look in Dean's eyes because Dean realises right there that Alastair was right, Sam was turning into something, and as much as Dean tried, he could never save his brother. Alastair manages to give a smug smile in Dean's direction without anyone noticing, showing how right he is.

Sam never notices how Dean closes his eyes with defeat.

Even Alastair thinks that Sam doesn't know a lot about his brother.

This one was really hard to do, but I really wanted to shed some light on Dean's time in Hell. Hoped you enjoyed it.

Meg is next up.