Riley has spent his whole career working on commercial cargo boats and the odd fishing vessel, but his dream has been to work on yachts. One day, the crewing agency gives him a call. There’s a yacht with an opening in Norway, and Riley doesn’t hesitate to accept the job. But the crew was expecting a woman for the interior crew, not a man for a deckhand.

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.

What happens when a guy is caught looking in the panty drawer of his girl roommate? He's given the time of his life when she feminizes him and turns him into her girlfriend to party with. She teaches her crossdressing girly-boy new ways to have, and give, pleasure. His new life is far more exciting than he ever would have imagined as they both pleasure real men, each other, and themselves.

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.

When Russ loses his third girlfriend in a row to his overly voracious need for getting down and dirty, he complains to his friends that a girl wouldn’t ever have this problem. Case in point: His friend Krystal, a lesbian who sleeps with dozens and dozens of hot dates. But since he’s not a girl, Krystal proposes an alternate solution: Why not go see a fortune teller and see if a little hypnosis can cure him of his appetites?