At first all that Dean could feel was the awful relief that his Dad had broken too. He thought the world of John Winchester, and knew full well how strong he was, so part of him had feared that his Dad would think less of him for breaking. The news that his father had lasted just five years longer than he had was a welcome relief...one that he instantly felt guilty for. He wasn't supposed to feel better that his Dad understood what it meant to feel like a monster, but he did.
Part of him even wanted to believe that had he stayed in hell for as long as his Dad had, that he would have been strong enough to eventually refuse. It didn't matter that the refusal hadn't lasted, no refusal could last when faced with an eternity of torture alone, but somehow it counted a great deal to Dean. He knew he never would have been as strong as his Dad had after a hundred years, strong enough to drag himself out for a small window of time when the door was open, but if he was even close to being in line with his father Dean felt it was a big success...his Dad's shoes were pretty big ones to fill.
"I really thought I could make it." he admitted quietly, fiddling with the top of his beer can. "Every time I saw one of those bastards that I sent back, I laughed at them and said that I was Dean Winchester, that I was your son and Mom's and I was better than them. Especially at first, I was so damned cocky about it, I thought that I could survive hell, and do it because I was better than all of them. I was down there because I was a good brother, and that stood for something. I saw a few people give in before they were even tortured, the damned demons just had to show them what they were gonna do, and they just gave up. So help me, I didn't feel a bit sorry for those sons of bitches. I thought I was better than them too, I mocked them, Dad." Dean closed his eyes, remembering the days when it felt like he could last forever, and then the day when the reality came crashing down on him.
"One day, I just...I started to crack. I stopped taking it one day at a time and realized that Sam and you couldn't come to save me anymore. You were gone, and I didn't want to think about Sammy down there, and I realized that I didn't just have one lifetime down there but eternity. All of a sudden, it wasn't just getting through the day anymore, and I couldn't do it anymore." He looked over at his father, who looked strong despite his his bowed head and closed eyes. "Somedays I feel like a monster, Dad. I look at Mom and Ben and I feel wrong sitting there next to them, hugging her, playing catch with him with the same hands I used to do those things. Sometimes I just want it to go away, sometimes I'd rather not feel anything than to feel that."