Super Jack Pro
Platform: PC-88, X68000
Publisher: G-Club Software
Year: 1988
Game: Cards, Casino
Difficulty: 3
Nudity: 4
Strip Blackjack with a schoolgirl. Features voiced animated strip scenes and a fairly tough AI, though only one girl to play against. The PC88 version has only monochrome graphics and lacks the voice, of course.
Screenshots taken from the X68000 version