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Crowley should have known better then to put all his chips on something Lucifer had created, but Dean was always too smart to hand his soul over willingly. The omega had unwittingly been bonded with a demon before, which Castiel broke with a bond of his own… which he then broke in his search for power, just as Crowley had planned.
Dean was paranoid then, clutching his broken soul inside of him, desperately putting up barriers to keep from being hurt again. Castiel never stood a chance of winning him back, either. And so, the Mark of Cain. The Mark had done more then just making Dean rely on the alpha for his addiction… It made him a demon, someone who could have a real bond with the King… could breed and would kill for him.
The situation was perfect… until it wasn’t.
Even as the moose ‘cured’ his squirrel though, their bond still existed and though Dean suddenly fought against it… Crowley was determined to have his demented fairy-tale ending.