IT'S NEVER AS SIMPLE AS ESCAPING THE PAIN
John Winchester may not have been the kind of touchy feely dad that Dean sometimes wished he was, but he was a teacher, a mentor, someone to follow and someone to live up to. Dean had always been afraid of letting his dad down, to be a disappointment. He had always craved his father's approval. Whenever his dad expressed pride in something Dean had done, Dean glowed and felt worthwhile. And so Dean constantly sought to make his dad proud, in order to be able to bask in that brief attention.
Dean rarely heard his father say that he loved him, so to hear that he was proud was the next best thing. Dean learned what to do to make his father voice pride in his eldest son, but he was never sure what he had to do to make his father say he loved him. So Dean stuck to what he knew. He became dependant on his father's pride to make him feel a part of something and, when John Winchester sacrificed his own life in order to save Dean's, it left Dean hollow. Somewhere along the line and hidden deep inside, Dean couldn't help but think that his father's last act implied that he would rather go to Hell than to stick around and watch Dean fail again, by dieing.
It left Dean without someone to guide him, to instruct him in what to do. John Winchester's death left Dean without someone to follow, without someone's praise to strive for…until now.
Now there was someone else who wanted to nurture his skills, who wanted to be his mentor. Someone who was waiting for Dean to do things that he could tell Dean he was proud of. And Dean craved it. Dean simply could not be alone and without purpose. He had been taught how to be the victim and he'd tried to accept that role. Hell, he'd tried for thirty years. But the physical torture was only a part of Dean's hell. There was also his internal torture, like the constant terror, but emotionally it went deeper than that for Dean and it became another reason for saying "Yes." It was the despair, the desperate wish for someone who would tell him he did good, that he was meeting their hopes and expectations. That he made them proud. And so, finally, Dean took hold of what he had to do in order to get off the rack
Alistair was there whilst his father wasn't. He offered to teach Dean, to mentor him; he encouraged Dean to make him proud. Dean hated the agony of constant torture relentlessly visited upon him, but maybe even more than that, he hated being alone.
Dean reasoned with himself that he was only in Hell because of the deal. But in making the deal, hadn't he proven himself willing to sacrifice his own life to save someone else? In another life Dean thought, surely this act alone meant he should have had a place in Heaven, never mind the hundreds of other lives which had been saved because of what he did?
Alistair was waiting for him. He wanted to be Dean's guide, he wanted Dean to stand with him, he wanted Dean to do a good job and Dean, he needed to be needed. He needed a purpose. He needed a father…