Platform: PC-Engine CD
Game: Cards, Various (Blackjack, Poker, Speed, Babanuki (Old Maid))
You play as a group of three female thieves who challenge random girls to card games. The game you play is randomly selected before the match with the first girl, and the conditions to strip them vary depending on the game you're playing. The opponent girls' clothes fade to transparency and they pose in their underwear once you win, and unfortunately, your characters don't strip if they lose. You can adjust the difficulty and the number of rounds to play, though I have to ask why anyone would want to play 100 rounds of Old Maid.
* - There is apparently a cheat code that allows you to see more of the girls than their underwear, but we've never gotten this to work.