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.

Max keeps getting into trouble, manipulating his female classmates (he calls it ‘charming’ them). Finally, the school principal can’t take any more, kicking Max out and leaving him with only one option: an all-boys boarding school with strict rules, and no access to women whatsoever. Even the internet at the boarding school has been programmed to block images of women.

Prom is approaching, and Jeremy has his eye on Amanda. Well, every guy has his eye on Amanda, and a few of the girls too. She’s the hottest girl in school, so Jeremy doesn’t actually think he has a shot.

Danny was sure he was going to get the big promotion at work—and then his boss tells him that it’s gone to someone else: Deakins. No, Deakins doesn’t have the numbers that Danny has, but Deakins has a wife, and the company’s clients have wives who want other wives to mingle with at events and company getaways. Stunned, Danny sinks into despair. Finding a woman has always been a struggle with his demanding work schedule. He makes great money… but no woman seems to want a man who spends most of his waking hours at the office.

Sam was just another lazy kid - no direction in life, hanging out at his parents’ house, no girlfriend, listless. His parents gave him choices: move out and work the only kind of job he was ready for, a minimum-wage job, or join the service, or go to a girls’ finishing school. Sam becomes Samantha and goes off to school - a school where the girls are taught how to take care of a man and be the ideal wife.