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.

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.

For years, Fabian has been curious about the lives of the women all around him, but they never seem to want to talk to a too-curious man about it—there's always a bit of the experience he couldn't get to or questions that would seem too inappropriate. But now, he has a brilliant new cover plan that will help him get to the bottom of things: He's going to write a book about it! Purely for research purposes, of course.

When Ben invites his best friend, Jesse, for a weeklong getaway to his family’s beachside vacation home, Jesse is thrilled! It’ll be the perfect way to spend some quality bro time together, away from jobs, chores, and Ben’s nagging mother, who is always asking him when he’s going to find a nice girl and settle down. He’ll settle down later - when he finds the perfect girl.

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.