Popping His Cherry

On the 10th year anniversary of slave wades service to the Femdom Empire it was decided that he must finally give up his anal virginity. The one humiliating thing he vowed never to do was anal sex, but he had no choice in the matter, the Mistresses have decided he must cement his devotion by popping his anal virginity! Mistress Chanel decided to do the honors in breaking him in as a new anal fuck toy.