Virgin Breaker Yuki (1975)

Original title: 玉割り人ゆき

Based on a manga by Kosuke Miki and Tadashi Matsumori, this film follows the adventures of Yuki, who works in a Kyoto red-light district house of ill repute as a "tamawari," or "virgin-breaker." She's the gal who gets first dibs on the new recruits to the brothel (some willing, some not), and it's her job to break them in for future clients. The film finds Yuki involved with a group of political rebels and anarchists after the Peace Preservation Law was passed in 1925 and walks a fine line between black humor and severe cruelty.