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.

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.

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.

Ari's boyfriend has just granted her a hall pass to sleep with Hollywood's sexiest actor, should the opportunity present itself. When she suddenly gets her big chance to live out her fantasy, things take an unexpected turn. Dallas Monroe is sick of being labeled a man trophy. He wants desperately to find true love and change his sex symbol image to that of a serious actor.

Luke Godfrey knows me only as Jade, the sweet stripper whose curves he is forbidden to touch. But when he is the surprise guest lecturer in my business class, he finally meets Abby Reynolds - the real me - even though I've done my best to avoid the gaze of this silver fox. Will this hot, high-flying CEO fall for the real me? Will he add "fall in love" to his to-do list? Can I get my startup off the ground without the help of a sugar daddy? And can I find true love - and lose my V-card - too?