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.

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. 

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. 

Harry has spent his entire career working toward his next big promotion, but on the day before his performance review, he discovers that it's going to be denied to him—the company wants a woman for the job instead. Gender diversity in management is important, but that doesn’t change the fact that Harry is crushed to lose his job and everything he's worked so hard for.

When Charlie’s friend Vanessa crashes his gaming party and whines about the boys never wanting to have a night on the town, Charlie shoots back that he’d love to go out if he could get the kind of romantic attention she does for just one night. Without missing a beat, Vanessa offers to give him just that chance and see just what it’s like to be a gorgeous girl on the town. With his soft looks and slender body, she thinks she could make him into a rather pretty girl.... Why not, Charlie wonders? It might be fun.