When Connor starts a new job, he's pleased to find he's the only male in an office full of attractive women. But then he starts getting mysterious, anonymous messages telling him to do some very taboo things. Intrigued, he follows the instructions....

When burly tradesman Tyler finds some women’s clothes hidden away at the empty school he’s working on, he can’t resist exploring his secret sissy fantasies. But the strict Headmistress catches him in the act and punishes him in a most unexpected way–forced to fully feminize, he is spanked over her desk and made to satisfy both her and himself. But who’s enjoying it more–the hot but stern Headmistress, or big, butch Tyler, all dressed up as a girl?

“I’m Peggy by name and Peggy by nature,” the dominatrix said as she bent him over. Darren looked up at the sexy yet terrifying woman who towered over him in her thigh-high leather boots. How on earth had his bachelor party stag night ended up like this? And was he really going to submit and let her do that to him?

The mystery of the femdom office continues as Connor is trained as the submissive, sissified office toy. Under her desk, Connor must show his absolute devotion to his demanding Mistress and the other women, as they torment and use him at work. To keep him in line, his dominant Mistress places him in male chastity, further controlling him with tease and denial and ensuring that he can only find satisfaction at her command.

A disastrous first attempt at femdom leaves Jonathan bruised and humiliated, and he’s at rock bottom. Then, sexy, sophisticated, and wealthy Mrs. Cavendish comes to his rescue and promises to make everything all right again - at a hefty price. She demands total obedience and utter control over him.

Trevor and Anna struggle to make their femdom play fun for both of them. Anna struggles to feel confident in her dominance as Trevor uses his safeword whenever their play veers from his carefully constructed scripts. Finally, Anna's had enough, and she gives Trevor an ultimatum: try femdom for real for three months or give it up entirely. In addition, she wants to train with a real dominatrix, the seductive Mistress An-Li. Trevor agrees to Anna's demands, and in doing so unwittingly seals his fate as her caged, sissy slave.

Toni’s twin brother Riley has just graduated from art school, and Toni invites Riley to live with her in California until he can find a good job. Toni has always wanted a sister, and Riley has always been a bit of a femboy anyway, so Toni puts her plan into action. She manages to enlighten Riley about the nuances of presenting his feminine side and immerses him in the pleasures of catering to his feminine persona.

It’s Christmas break. Gorgeous Piper loves nerdy Jake’s passion for buying her clothes, but her intuition tells her he does it not only because he loves her so much but also because of his hidden desire to wear them himself. She buys her love everything needed for crossdressing and transforming Jake into Jackie, her girlfriend. That afternoon, she enlightens him in the nuances of presenting his feminine side and immerses him in the pleasures of catering to his feminine persona.

At the Sissy Dollhouse men are captured by the beautiful dominatrix Tanya and turned into mind controlled transgender dolls using seduction, drugs, hypnosis, surgery, and hormones; then they are used as programmable prostitutes for fulfilling the fantasies of rich clients.

A geek named Joss, working on his PhD thesis on motivation, rents a house away from the noise and takes in a roommate named Marcy to help pay the bills. Little does he know how lucky he will be to have Marcy as his roommate. She is another PhD candidate, also working on a thesis about motivation. Gorgeous and intelligent, Marcy motivates Joss to discover things he never would have dreamed of, and they learn about motivation, love, sensuality, and femininity. She soon has Joss fully crossdressed and feminized to experience life as Jossie, a desirable girl rather than his geek self.