Dressed in a maid costume, the femboy sissy is locked in a chastity belt, his anal training set to begin. His mistress, a cosplaying shemale dominatrix, releases his throbbing cock and replaces it with a thick dildo, making him beg for mercy. Joined by other crossdressers and a trap, they all take turns fucking him, their shecocks sliding in and out of his tight ass. The sissy, now addicted to hard anal sex, pleads to be filled by all of them at once, leading to a wild, messy group pegging session.