The King of Minami: Trans Woman Blues (1998)

Sinopsis

#25 in the King of Minami series. A trans dancer named Rio is in debt to Manda after trying to finance a trip to the US for gender reassignment surgery, still illegal in Japan. The owner of a prestigious nightclub recruits her, introduces her to a doctor in Osaka who performs the illicit surgery and even agrees to foot the bill. But when the club owner turns out to have ulterior motives, Rio turns to Manda for help.