SM Choukyoushi Hitomi: Bangai Hen Super Nintendo

This game is an adult point-and-click adventure game, which follows various escapades involving the protagonist, Maki, and the transfer student Hitomi (seemingly unrelated to other characters named Hitomi in the series). Throughout the game there are several quiz battles, where the questions mostly center around obscure knowledge regarding the previous title in the series, SM Choukyoushi Hitomi Vol. 2. Getting at least 5 out of 10 questions correct will force the opponent to strip and the game to progress; otherwise the protagonist will have her own clothes forcibly removed and the game has to be reset and started over from the beginning. However, due to shoddy programming, the same question can be asked multiple times per quiz (sometimes right after that same question was already asked).