Shinjuku Mayonaka Monogatari: Otoko to Onna 1972

Name: Shinjuku Mayonaka Monogatari: Otoko to Onna
Released: 1972-04-19
Cast: Hidemi Hara, Yoshie Kitsuda, Michiyo Mako, Hiroyuki Mikawa, Toshihiko Oda

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Synopsis:

Kiyomi, a popular hostess at a bar in Shinjuku, has a traumatic childhood that makes her only sensitive to sexual intercourse with women. One day, the girl she loved as a junior hostess betrayed her and slept with her man. Uncomfortable with men, Kiyomi "swaps places" during sex with her new girlfriend, a trans woman Kaoru.