Baka to Hasami

Yousuke is enjoying a care-free life, living off of a wealthy woman. One day, management of an establishment that forbids sex between staff and their clients, finds out that he's been sleeping with the girls! Yousuke receives punishment as payment for breaking the rules, by having his virgin ass stuffed with a dildo and being forced to wear a chastity device. Yousuke, who's been kicked out of his home as a result of what's happened, confronts the man who is the source of his issues and tells him that he'll be the next one to take him in.

(Source: Core Magazine, translated)