Dochinpira 12: Dangerous Pheromones 1995 on netflix

Jin, the unstoppable gigolo, becomes infatuated with a beautiful woman named Emi he spots on the street. But not only does she reject him, he also ends up, as usual, being chased by punks from the Gokuraku gang. Later that night, Jin meets Norishiro at a bar, who happens to know Emi. She offers him a deal: if he can seduce Emi within five days, she’ll pay him 1 million yen. Jin goes to the club where Emi works, only to find out she has a boyfriend, Toshio, a civil servant who is drowning in gambling debt, owing 10 million yen to Fujita of the Gokuraku gang. Now he demands Toshio provides Emi for prostitution. At first, Jin wants nothing to do with Toshio’s mess… but something changes within him.