I think Scott is very much like Dave Cheung and Jamal Joseph (creators of Chugworth Academy): he's at his best when he cheerfully and horribly throws all societal conventions to the wind and writes scripts that would be appalling in the hands of just about anyone else.
As a disclaimer, one of the only reasons I really find this really funny is that I've known women who actually were into tentacle porn, which shed a lot of light of understanding on the subject for me. I love panel 3: "Ha! I'm just kidding. Or am I? Who knows?" If this is too far past the edge for anyone, I apologize, I realize it's pretty raunchy stuff.