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.

Brandon tells his wife, Ellie, that he wants more from her in the bedroom. It turns into a big fight, and Brandon assumes he’s going to spend the next week sleeping on the couch. So he’s surprised when Ellie initiates some intimacy… and she throws a finger into the mix, putting it somewhere it’s never been before. It feels weird, but not unpleasant. Maybe Brandon even likes it. So he lets her do it again the next night, and the next.

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.

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.

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.

Patrick is unaware his new wife Elizabeth has always prefered men with a strong feminine side. When businesswoman Elizabeth hears him telling his best friend he only married her for a huge payout in a future divorce, she springs into action. Her plans for his gradual feminisation change to something more rapid and girly.

After allowing his marriage to grow stagnant, Brad is faced with a tough decision. Wear a chastity cage or lose his relationship with his wife, Melissa. Melissa has issued him this ultimatum after years of growing unhappy in their marriage and because she believes that wearing a chastity cage will help turn Brad back into the loving, supportive man she married.

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 Lawrence gets a mysterious invitation back to the house that he and his ex-wife Vanessa used to share, he’s surprised to hear from her for the first time in a year. Surprised, but also hopeful that she wants to take him back. To his delight, she does. But she doesn’t want him back as the man he used to be. Instead, Vanessa has plans to turn Lawrence into the perfect partner with the use of a chastity cage. He accepts, not knowing the allure of the chastity cage or the control that he has just surrendered to his ex-wife. Two things that he will quickly learn.

It encapsulates five titillating reluctant feminization stories of men submitting to sissification brought upon by domineering t-girls and femdom.