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We all know Dean loves Sam and only Sam.

Which means when Sam was possessed by the devil yep Dean wanted to f*ck the devil.

I am pretty sure this all was before that

Originally posted by HulkIsHulk
I am pretty sure this all was before that

Technically you are correct in that the dream sequence happened in the middle of the 5th season before Sam was taken over by Lucifer. However, by that point they definitely new that Sam was the devil's vessel so..