I think that Dean's breaking point could have been when he finally realized that he's not getting out of there.
Although, I do think it could also be that Alastair did use Sam in some way or maybe one of his parents, maybe had a look-a-like or an illusion or something, of Sam torturing him or something. And I wouldn't put the Non-con past him either.
Either way, it broke my heart to see Dean in such pain, and not only the physical pain, but the emotional pain of finally giving up, which we have never seen Dean do willingly.
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Although, I do think it could also be that Alastair did use Sam in some way or maybe one of his parents, maybe had a look-a-like or an illusion or something, of Sam torturing him or something. And I wouldn't put the Non-con past him either.
Either way, it broke my heart to see Dean in such pain, and not only the physical pain, but the emotional pain of finally giving up, which we have never seen Dean do willingly.