As she excitedly begins preparing, Laura starts to notice that Jake's presence in her life is becoming much more intense and her dependable pal Jake suddenly becomes her sexy, gorgeous lover, leading to some hot erotic activities that result in an awakening within Laura. Laura is having an early mid-life crisis. Fast approaching her 13th birthday, nothing has gone quite to plan.

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.

Matthew Angel is stuck. He's 41 and spent his life denying who he is and what he truly wants—until he stumbles upon a unique offering at a specialty charity auction: a Christmas Daddy experience.

Oliver likes writing, reading, and the feel of satin and lace against his body. He also talks way too much when he’s nervous, knows more trivia facts than any man should, and is about as good at dating as he is at skiing - which is to say, completely and totally inept. David’s never been with a man before, despite recognizing that some men make his pulse race and his body heat. But no one has ever made him as hot as his newest ski student - adorable, athletically challenged Oliver.

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.