John wants to hire Kimber James as his babysitter, but first he needs to understand what a transsexual is. The only way Kimber knows how to explain that she’s a…

Babysitting a rockstar is more work than it seems. Keeping a grown man in line, and on time, is almost a thankless job. But this Tranny has it made! Her…

Danielle Foxxx is a hot tranny MILF who’s bi-sexual babysitter has asked for a raise. Danielle will give him a raise, that’s for sure. This super busy pornstar treats her…

Yasmine Lee may not understand a lot of English, but she definitely gets it when her boss starts to flirt with her! The whole reason he hired her as a…

Aubrey doesn’t know why she’s been hired to babysit two legal aged brothers, but her paycheck makes it worth it. But these boys are more interested in banging her than…

When it comes time for Kimberly’s annual evaluation, the dad calls her in from the pool and asks her to perform some special care-taking skills. Whipping out his dick, this…

After her arrival to her new nanny position, the boss runs down all the expectations he has. Among them, Alexis Lissa needs to understand, is her sexual availability to him…

Even though Vaniity only has to babysit on the weekends, her boss has her live in the house full time. Because he has needs beyond someone taking care of his…