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.

Tom McCallister has been in love with his best friend Lyla for as long as he can remember, but what would be the point of telling her that? He's known that it's hopeless ever since she came out to him as a lesbian during their freshman year of college. Lyla likes women, and Tom is definitely not a woman. But when Tom loses both his job and his girlfriend on the same day, Lyla is still the first person he turns to for support. She tells him to drop everything and fly out to see her in New York, confident that some friend time is exactly what he needs to get through his slump.

Drew Crossfield is a fashion designer with a secret desire that he's never dared to explore, no matter how badly he might want to. When famous style icon naTasha notices him, there's no turning back. She knows a closeted sissy when she sees one, and she’s determined, from the start, to change this drab dresser into the feminized glam girl of his dreams.