I'd never tried this line before. I just tried it with AA and my two check-raise attempts failed horribly. It made me feel pretty stupid because I'm sure this player was donkish enough to call me all the way down with second pair, but I got greedy. I guess this would work better against a known floater, and against calling stations I should just let them call.

Could you explain what history you had with this guy. Did you check-raise him on the turn with a monster, earlier in the session?