I think I have a winner here:
He is My Master. Ugh. Yeesh. The title says it all. I felt like I needed to scrub away the filth of misogyny for hours after that one. I know that Anime isn't known for it's progressive attitude towards women but the whole series was an experiment in inventing new ways to make rape, molestation and pedophilia seem harmless and flattering. And it lasted for 12 episodes >.<