In Book One Of The Lost In The Hood series, Jordan Jones, a software developer, has a secret. He likes to crossdress and fantasizes about wild kinky sex - public sex, humiliation, and being treated like a whore. For the most part, he can control his wild kinky sexual urges. But, dressing as Jennifer, his cross-dressing persona, he's been unable to control. He's getting married next week to a wealthy woman he loves, adores, and is his best friend. So, this is his last weekend as a bachelor, and he plans to dress as Jennifer. This is the last time he vows.

His crossdresser friends, whom he plans on meeting later Friday night - doubt it. That is, as soon as he finishes the project he's working on. He transforms into Jennifer in the company gym, which he thinks is safe to dress in due to his software skills. He controls entry. Or so he thinks.

Jada, an ex-con, hacker, and a private investigator hired by his wife to check up on Jordan, override Jordan's hack and catches him cross-dressing. Jada blackmails him into being one of her prostitutes, or she'll not send a good report to his future wife.

Jennifer finds herself lost in the hood, fulfilling her wild kinky fantasies.

In Book Two, Jennifer is left after having public sex with two strangers in an alley - Lost In The Hood. Jennifer has only one way to go. Through the door that a stranger came from and left evidence of their recent sexual encounter all over her face. Jennifer begs for help and receives it.

Once she’s cleaned up and ready for round two, she meets up with Jada, the woman blackmailing her, and Fat Tony, the man that hired her to have sex with him in the alley.

Fat Tony appreciates her extraordinary sexual performance and refers her to another client—a businessman with a wild, kinky request. He wants public sex, and in the nightclub, under the table.

After pleasing the businessman, Jennifer meets a couple - a transgender dominatrix and her submissive male for round three. Jennifer is indeed a sissy crossdresser.