In The Breaking Cage, Dominatrix Karin Calloway introduces new friend Joanna Barnes to the delights and conveniences of having a slave-husband. Karin used her infamous Breaking Cage to turn Joanna's husband Gary into the chastised, feminized, sissy-cuck Donna. Joanna learned the delights of other lovers as sissy Donna learned to serve, obey and endure humiliations and torments.

Todd and Evelyn Grant are white-collar criminals, convicted and sentenced to prison. Yet they are given a second chance by hardened prosecutor Tanika Jones, who offers them a new sentencing alternative. Instead of 15 to 20 in a correctional facility, they are offered a 10-year sentence working in the mansion of Dr. Carl Wilkins and his beautiful wife Albany.

Shy eighteen-year-old Jody has always been in love with his best friend's mom, and she loves the attention. Using her sex appeal, a little gentle humiliation and a firm, motherly hand; she strives to make the pretty boy into the perfect sissy toy.

Michelle and her black lover, Antoine, have plans for Michelle's husband, Simon. A weekend at Antoine's mother's estate turns out to be a turning point in Simon's life. The hapless husband undergoes the initial training to become a WSB. Under the tutelage of senior sissy maids Paulette and Pansy, Simon becomes Simmi, and is on his way to becoming a member of the exclusive WSB Club.

His world is turned upside down when Tim Walker's secret life as Collette, a cross-dressing sissy, is discovered by his coworker. Humiliated and blackmailed, he must become Master Brad's sissy-maid slut. As Brad assumes control, Collette takes over more of Tim's life. It only gets worse when Master Brad enlists the help of some of the office women and takes sissy Collette shopping to a fetish store. How far will it go? How much humiliation must sissy Collette endure?