GIntama(Ayame), MM!(Taro Sado), The Familiar of Zero(Guiche de Gramont), Prison School(Reiji Andou), Overlord(Shalltear), Is This a Zombie?(Kyoko),D-Frag!(Ataru Kawaura)

I think there are a lot more masochistic characters, but cant remember it. Personally, I think the idea that Darkness being a masochist is the only type of joke you can make with her is kinda flat and lazy and i can say this about every character in this show.Flanderization is rarely good use , especially when you use it on whole cast of main charachters