Definitely Dean!He was being tortured for 40 years!I think that Dean's torturing methods were very mild compared to Alistair's when Dean was in hell!

i meant tortured only in 4x16 but it was defo Dean!
although Dean was the torturer, Alistair knew what buttons to push to make him feel pain..

I can never give sympathies to Alistair.

I thought the same thing as toti8! But I still say Dean, and I agree with lucysmileyface.

It was probably a walk in the park for Alastair. It just seemed like physical pain washed off him. The way that Alastair psychologically twisted the knife? Dean had no defense against that. What he learned was the worst torture possible. Sticking a knife in Alastair just doesn't compare.

i agree fanfly, the psychological torture was way more painful..bruises and wounds heal eventually, the mind one the other hand never rests

Dean... Alastair probably knew that it was another way of torturing Dean, making him go down that path... telling him the things he did, Alastair seemed like he relished the pain. And everyone knows that with Demons it's this attitude: "You may beat me to Hell and Back, but the bruises will heal, and it'll only hurt you more to hurt me."

=( my poor baby .. ♥

teehee ;]

I thought the same as toti8, but my answer was Dean anyways x)

It was Sam using his "demon" powers that made Alistair talk, not Dean's torturing skills.

Alistair was a manipulative bitch XD Dean's nightmares weren't because of him being tortured but because he was the one torturing.