Dean Winchester was one of a kind. Alastair decided. Sure, he didn't last as long as old John, but the kiddo had become something else outside the rack.

He remembered the first time he placed the kid on the rack. Dean was quite the smart-ass. Cursed at him and even cracked jokes while the torturer's favorite knife and or scalpel sliced his skin. And whenever he asked the boy if he wanted the torture and pain to stop every after the session, the smart-ass always answered no. Alistair would always smile at him. He was a very patient demon. Like father, like son after all. Their hatred for demons was perhaps their driving force.

But this was hell. And everyone was bound to break, the Winchester was no exception.

John lasted for one hundred years on the rack before he managed to escape hell and disappear to God knows where. All because of the great yellow eyed demon and his great plans of psychic children and his great plans for Sam Winchester. Pfft, so much for greatness and grand plans… all in the trash.

Dean Winchester, on the other hand… only lasted for thirty years being tortured on the rack. Not even close to half the years his father stayed. But Alastair can honestly say he had more fun with pretty boy than to grumpy old man.

Pretty boy had a lot more issues than John. And Alastair, upon learning them, immediately dwelt on it.

Hidden anger and resentment for his father, some jealousy directed to his younger brother, the heavy burden he shouldered, hatred for demons and of course, the love and devotion he gave for his family. Alastair turned them all against pretty boy. And it slowly cracked the mask Dean Winchester constantly wore. The psychological blows plus the physical eventually wore him down and made Dean finally say yes.

Now, the next ten years with pretty boy was the most memorable. In the Pit, holding the knife meant power, and Dean surprisingly was very good with torture weapons.

The first soul Dean caused second death was a mess. The kid lashed out. Poured every pain he suffered in a single slash. No art, no beauty… only a bloody mess. And after that, he watched pretty boy crumple to the ground and cried like a child. Oh well, Alastair understood. It was Dean Winchester's last hold to his humanity.

"It's alright son. Let it all out."

The second soul on the rack was officially Dean's start of being Alastair's student.

"Let's start with something small."

Pretty boy picked up the scalpel.

Alastair then started his long (but interesting) lecture about the ways of torture, pain and the human body. He guided Dean's trembling hand. Slowly and strategically removing skin, cutting flesh and breaking bones in the most painful way possible while the poor soul strapped on the rack screamed and pleaded.

There were those rare times that a soul in the rack somehow manages to reawaken Dean's humanity. Usually, it was the younger souls.

"Kid, we don't have all day. Actually, we do… But nothing would happen if you don't start something."

Dean was just staring at the young soul, unable to move and start. The said soul hd started to scream and plead.

"I-I can't…" Dean said quietly.

Alastair sighed and immediately pinned him on the wall, "I think you have forgotten kiddo. These souls are here for a reason. They deserve to be here… just like you. Now, if you don't start cutting,"

Dean whimpered.

"I'll gladly put you back there… and remind you once again."

Pretty boy's response was n immediate no. After Alastair released him, h hurriedly took a knife from the work table and started cutting the kid.

Alastair had managed to break his soul to little pieces and mold Dean Winchester to what he wanted… a son… an apprentice. Unfortunately, everything was short lived. The pesky angel suddenly came one day and took his priced possession away from him. They took their Righteous Man.

The angel named Castiel managed to pick up Dean's soul and patiently put him back together. The angel boy managed to restore the Winchester's decomposing earthly body. Castiel whisked his apprentice out of hell where he should belong. Needless to say, Alastair was beyond furious… angels… and their 'holier than thou' attitude. He sneered.

But it seemed like Castiel had forgotten a small piece of Dean's soul in hell. And this… was going to be his connection to his son... his student.

Dean would come back in hell, whether he likes it or not.