Strip Poker (Commodore 64)

In 1985, my neighbor got a Commodore 64 from his cousin who must have upgraded to something else. At the time, we didn't have a clue how to use it but after reading a few hand written notes and figuring out how to explore the dozens of disks we realized we had a cornucopia of games (his cousin must have been into piracy). The above gem is one that we eventually discovered and let me tell you, that was pretty exciting for a prepubescent boy.

So basically you load up the game and start out with $100. You lose it all and the game is over but if your opponent (one of two girls though I believe Artworx, the company that made this game, sold expansion disks) lost her money, she would sell an article of clothing. It's hard to describe the excitement of waiting the minute or so for that next image to load after she lost a piece of clothing or the frustration of waiting that minute as she put one back on. Obviously this was well before the days of instant and unlimited porn everywhere you look.