Disclaimer: Wait, you mean they DON'T belong to me…awww man, stupid dreamland…*sniffle* Well that Eric Kripke sure is lucky!
Spoilers for season 2, episode 11 and season 4. (Few different episodes in season 4)
Breaking Point (Version 2)
For 60 years in Hell, he never broke; he endured the torture. His time was up too soon, all because a man had shot him in this crazy town while they packed to leave. Leaving Sam sooner than expected, with no way or time to find a way to get out of the deal. He knew he was barely holding on each time he was made the offer, but he kept tough. No matter how bad the pain is, it's only physical and he never gives, he's a Winchester, physical pain is what he knows.
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Then, he's back to the Wednesday he died. Time restarting and the 60 years of Hell are erased, they practically never happened. But Hell remembers.
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When his deal is officially due and no way out is found, this time he knows it's real.
No redo will work, no more time loop, though he doesn't really remember the 60 years anyhow.
But Hell remembers him, they remember the one that never broke, that got away. During those 60 years they tried to break him, but now they are more determined. They deploy all tactics, use everything they have.
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The other 60 years were painful, but only physically. This time, they use every trick they know. So many and so emotionally draining that everything seems real, even if his sanity could have told him otherwise.
*tactics used*
"What about Sam, the reason you sold your soul. So that he could live. What if we took him anyhow. What if we sent a demon after him, brought him to Hell to endure the pain with you?"
Images of Sam dying. Coming to Hell. Being tortured with worse devices than what they used on him. Sam screaming in pain, begging for them to stop, but they refused to give Sam the same offer unless Dean took the offer himself.
"If you take our offer, the pain stops for the both of you."
*tactics used*
Images of everyone he had ever saved in his lifetime, killed instantly, without thought or hesitation.
*tactics used*
His dad (Which was really Alistair, making him hallucinate to see his dad) "I am a torturer son. It's okay to torture these souls. After all, they were Hell worthy. Besides, the pain stops the day you take your rightful role and help me with the torturing."
His weak, pain filled refusal, "That's not who we are dad."
His father's face, filled with shame, disgust, being let down. Then a smirk and pleased scorn, "I was hoping you'd turn me down. Now I can show you how I really feel towards you."
Intense pain and his father's laughter is the only thing he is aware of.
*tactics used*
Seeing Sam die. Sam coming to Hell with black eyes, "This is what I am Dean. All because of you, you brought me back. You changed me. Now I am forced to live in Hell. I hate you Dean, I hate you. Why did you do this to me?"
His weak, broken reply, "Don't say that Sammy. I did this for you. This isn't who you are."
"This is exactly who I am. I am this monster because of you. I could have been normal. If you hadn't picked me up at Stanford, if you had listened to dad, if you hadn't brought me back changed; I would be normal. Could have been safe, happy. Died normal, died happy, and went to Heaven, like normal. You took that all away from me!"
*tactics used*
"This is what you made Dean." Sam would tell him, right before he began for the day. Dean could have handled the pain, but not the emotional torture.
*tactics used*
Never able to help those who needed him, but forced to watch their pain and suffering. To lost in pain and thoughts to protest too much. Tears became a constant mantra running down his face, the only way he knows that this is real. He didn't realize that although the pain was real, hallucinations were forced upon him almost daily. As far as he knew, Alistair only came in once a week; Alistair came in everyday.
"Your dad caved, be a good soldier and follow in his footsteps. You will be pain free, the only thing you have to do is inflict the pain on someone else. Those that deserve to be here, those that were evil before death."
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Indescribable pain, will with weapons and foreign instruments no mortal could think of, used daily. Used daily by Alistair, faceless people from his past that also informed him of how he had ruined their lives, his dad's face, but more often the face belonged to Sam.
The weapons were designed to bring maximum pain in the least amount of time as possible; the faces that did the torturing there to make him break.
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If it weren't for the fact that each new day his body reformed so that the pain could restart, taking away every injury inflicted during Hell, nothing would have remained. If it did, it was nothing more than a lump of blood, scars, burns and various other injuries to far injured to recognize. Yet, he could still fill every wound inflicted upon him. Not one thing ever passed, the pain remained.
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So after the constant mantra of chants and 30 years of holding on (plus the other subconscious 60 years), he breaks.
He learns the right methods in the most gruesome and painful techniques. The longer he hears the agonized screams, the more he enjoys it. He enjoys it because it's not his voice screaming for the pain to stop. It's not the people he saved screaming, or doing the torturing to him. His dad and Sam have stopped torturing and taunting him. He doesn't see a friend or himself screaming for mercy, he sees a stranger. A stranger that will feel all he went through.
He doesn't realize they needed him to break, needed that first seal to break so that the Apocalypse can begin. They need him to stay in Hell so that when the last seal is broken and Lucifer walks free, he will not be able to stop him.
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After 10 years of inflicting pain the soul he sold is beginning to fade. His reasons for inflicting pain lost in the agonizing screams he has become accustomed too.
Then, in the tenth year, he once more eludes Hell. Raised before his soul vanishes, his body unmarred with any scar except a hand print. Saved by an angel called Castiel.
This time the memories remain, and he only remembers the second time in Hell. The taunts, torture, offers and the fact that he broke after 30 years.
+++END+++
Please let me know what you thought and thank you for reading.
I also plan on doing a sequel, maybe, on Dean's emotions, etc, of how he felt for breaking, how he was broken and how he feels. Let me know if you think it is a good idea.
Chow, Siara