This book contains Jessica Whip's entire Feminized Sissy series, which consists of the following five manuscripts: Feminization Erotica: Worthless Little Sissy (Feminized Sissy Series Book 1), Feminization Erotica: Sissy Caught in Web (Feminized Sissy Series Book 2), Feminization Erotica: Sissy Maid Gets Owned (Feminized Sissy Series Book 3), Feminization Erotica: Sorority Sissy (Feminized Sissy Series Book 4), Feminization Erotica: Undeserving Little Sissy (Feminized Sissy Series Book 5).

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.

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 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.

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.