けっこう仮面 ~おしおきパラダイスの巻~

When a Japanese game's title includes a word that can be understood as "corporal punishment" (shioki), it's not hard to guess the theme of the "story". Basically, the player is cast as one of Satan's minions, who also happens to be the new "punishment teacher" in the Sparta High School. As the protagonist arrives at the school, he quickly attends to his "duties". However, the sadist's efforts are thwarted by a mysterious, masked, completely naked woman. The player's job is to make sure this won't happen again - which means defeating the super-heroine, and continuing to torture young girls...

[From Moby Games]