Okama Hakusho(1989)

College student Shinya Okama is initially tricked into working at a gay bar by his friend Tanaka, but he starts to enjoy it when he sees how cute he looks in drag as "Catherine". However, his infatuation with himself is short lived when he falls in love at first sight with Miki, an innocent college girl and regular at the bar who happens to look a lot like Catherine. Although the two of them hit it off right away, Miki only knows him as Catherine, and to top it off, Miki already has a boyfriend. Not wanting to concede defeat just yet, Okama continues his struggle to get closer to Miki while trying to prevent her from making any progress with her boyfriend who just wants to get in bed with her.