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).

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.

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.

Dress like a girl to join an elite society? A master’s degree student wants to join an exclusive and elite secret society where the members network and become huge successes financially. The only problem is that he has to pay his dues first. Can he do it? Membership requirements: A good person, unbiased, non-judgmental, with no homophobic or gender-slandering tendencies. An understanding of the importance of balancing masculine and feminine energies. Dedicated to helping other members. Able to keep secrets.

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 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.

Prom is approaching, and Jeremy has his eye on Amanda. Well, every guy has his eye on Amanda, and a few of the girls too. She’s the hottest girl in school, so Jeremy doesn’t actually think he has a shot.

A house that turns boys into girls? A college student is looking for a house to rent and comes across an unbelievable deal. According to the gorgeous girl vacating it, the place is enchanted and has a closet with women’s clothing and accoutrements that can never be emptied. She also claims it turned her from a boy into a very special girl while she lived there.

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.