The OVA, which is based on Saikaku Ihara's novel Koshoku Ichidai Otoko (The Life of an Amorous Man), depicts the life of Yonosuke, a libertine whose sole purpose in life is to seek sexual pleasure. At the age of 18, Yonosuke is disowned by his father, which sets him on a 16-year journey filled with changes and wanderings. His life takes a turn at the age of 34 when he inherits his father's enormous wealth, along with his father's forgiveness. When Yonosuke reaches 57 years of age, one of his tailors, Juzo, approaches him before embarking on a journey to Edo. Juzo has foolishly made a wager with a wealthy merchant, betting that he can sleep with Komurasaki, the most renowned courtesan in the city, on their first meeting. If he succeeds, he will win a villa, but if he fails, he will lose his manhood. Yonosuke is taken aback, as he knows how difficult it is to win over high-ranking courtesans. The tayu, or top-ranking courtesans, were not only physically attractive but also highly cultured, educated in poetry, calligraphy, painting, the tea ceremony, and other arts. They would not sleep with a client until the third night, spending the first two nights getting to know each other through greetings and socializing. The lower-ranking men who viewed them as "untouchable" idolized and respected them. Outraged by Juzo's foolishness, Yonosuke takes him to Edo and helps him meet Komurasaki. Juzo's nervousness makes him a laughingstock in the tea-house, and he soon gets drunk. Inadvertently, he spills wine on Komurasaki's kimono. However, the courtesan remains composed and replaces her stained garment with an identical fresh one, unaffected by Juzo's actions.