Platform: Atari 2600
Without a proper censorship board, and no ESRB to be found, the 1980's were filled with some hilariously primitive attempts at interactive adult entertainment. The most well-known example of these being Custer's Revenge in which players take on the role of a naked General Custer who must dodge arrows in order to have sex with a Native American woman tied to a pole.
It'd be easy to get offended at the nature of the title, but developer Mystique also produced General Retreat in which the gender roles are reversed. Now, before you go praising them for being progressive enough to let players control a woman taking sexual advantage of a man, it was designed as the cheapest possible follow-up for their line of adult games.