Dochinpira 13: Virgin Palace Breaking 1995 on netflix

Trying to demonstrate his gigolo skills to some rookies, Jin gets shot down by the beautiful and feisty Mao. His next attempt, Ami, turns out even worse, because she steals his money and vanishes. Discouraged and considering retirement, Jin wanders into a bar called “Life Counseling”, where the bartender moonlights as a fortune-teller. The reading is grim: Mao, the beloved sister of a friendly yakuza, is destined to be defiled by a gigolo. When Jin finds Ami again, he uncovers the truth: she’s not only a virgin but is being blackmailed by a gang that forces her to seduce and rob men. Now Jin must dive into the criminal underworld to save Ami… and maybe find redemption along the way.