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?

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....

“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?

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.

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.