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…

When Mike Mancini interviews busty brunette Alyx Star for a babysitting job, he finds out its not children that she’s interested in, but the midlife crisis father that needs some…

Ricky Spanish may be an adult, but his mom doesn’t trust him home alone. The last time he was home alone, Ricky masturbated in the living room and the neighbors…

Hot sex is about to get hotter! Smoking hot big tit babe Skylar Snow is ready to fuck and suck! Deep poundings and cumfilled orgasms are about to get hotter!…

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…

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…

Lily Love is a slutty lesbian babysitter who has always had a bit of a crush on her employer Elexis Monroe. One day, when Lily is all alone in the…

Cassidy’s been entrusted to look after Mick’s house while he’s away, on the condition that she follow one rule: no boys allowed! No problem for this young slut, because right…

When Diamond Jackson caught her slutty babysitter Trinity St Clair fucking her boyfriend Jessy, Trinity thought she was done for. But Diamond, cock-hungry MILF that she is, just wanted to…

Last time we saw Cassidy Klein the Slutty Babysitter, she had just gotten caught in the middle of a wild lesbian love romp with her sexy girlfriend, teen slut Alli…

Alura Jenson is as busy as she is sexy, which means this MILF loves a good, reliable babysitter like Quinton James to take care of the house when she’s away….

When Aria Alexander took a gig babysitting for a hunky single dad, she could only dream it would lead to the hottest sex of her life. When Rob came home…

Sweet babysitter Nicole is jumpy, so when she starts hearing noises when she’s babysitting alone, she calls Kyle to come home right away. Kyle arrives to find Nicole cowering by…

The Tranny Nanny agent inspects each shemale that walks through his door for sexual virility, and a willingness to perform on demand. He’s a lot more thorough and generous than…

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…

Promising he’ll be a perfect gentleman, and never rat her out to his wife, this dad gets his way and gets to have sex with his shemale babysitter. It’s their…

Babysitter Megan Sage loves making money. So, when Tommy Gunn returns home and pulls out a wad of cash but only gives Megan two bills from his stack, she’s not…

When Veronica comes home early from a date to find her babysitter Megan and her boyfriend Markus experimenting with anal sex, she is initially shocked. Once over her initial surprise…

Adria knows the importance of balancing business and pleasure. Romi’s hired her on as a babysitter for the evening, with one rule – no friends over. Adria decides a little…

After bedtime, naughty babysitter Alina Lopez has the house to herself, letting her snoop into the affairs of sexy DILF Stirling Cooper. Alina’s been trying to attract his eye ever…

From the studio that brought you blockbusters “Babysitters” & “Cheerleaders”, Digital Playground presents its 3rd installment of the hit vocation series! The sexy nurses of Coos County General Hospital are…

From the studio that brought you blockbusters “Babysitters” & “Cheerleaders”, Digital Playground presents its 3rd installment of the hit vocation series! The sexy nurses of Coos County General Hospital are…

From the studio that brought you blockbusters “Babysitters” & “Cheerleaders”, Digital Playground presents its 3rd installment of the hit vocation series! The sexy nurses of Coos County General Hospital are…

From the studio that brought you blockbusters “Babysitters” & “Cheerleaders”, Digital Playground presents its 3rd installment of the hit vocation series! The sexy nurses of Coos County General Hospital are…

From the studio that brought you blockbusters “Babysitters” & “Cheerleaders”, Digital Playground presents its 3rd installment of the hit vocation series! The sexy nurses of Coos County General Hospital are…

From the studio that brought you blockbusters “Babysitters” & “Cheerleaders”, Digital Playground presents its 3rd installment of the hit vocation series! The sexy nurses of Coos County General Hospital are…

From the studio that brought you blockbusters “Babysitters” & “Cheerleaders”, Digital Playground presents its 3rd installment of the hit vocation series! The sexy nurses of Coos County General Hospital are…

From the makers of 2007’s Best Release “Babysitters”, 2008’s Best Seller & Best Release “Cheerleaders”, and 2009’s 1 hit “Nurses”, comes the bigger, sexier “Teachers”! Textbooks, homework, detention, lube, dildos…another…

From the makers of 2007’s Best Release “Babysitters”, 2008’s Best Seller & Best Release “Cheerleaders”, and 2009’s 1 hit “Nurses”, comes the bigger, sexier “Teachers”! Textbooks, homework, detention, lube, dildos…another…

From the makers of 2007’s Best Release “Babysitters”, 2008’s Best Seller & Best Release “Cheerleaders”, and 2009’s 1 hit “Nurses”, comes the bigger, sexier “Teachers”! Textbooks, homework, detention, lube, dildos…another…

From the makers of 2007’s Best Release “Babysitters”, 2008’s Best Seller & Best Release “Cheerleaders”, and 2009’s 1 hit “Nurses”, comes the bigger, sexier “Teachers”! Textbooks, homework, detention, lube, dildos…another…

From the makers of 2007’s Best Release “Babysitters”, 2008’s Best Seller & Best Release “Cheerleaders”, and 2009’s 1 hit “Nurses”, comes the bigger, sexier “Teachers”! Textbooks, homework, detention, lube, dildos…another…

From the makers of 2007’s Best Release “Babysitters”, 2008’s Best Seller & Best Release “Cheerleaders”, and 2009’s 1 hit “Nurses”, comes the bigger, sexier “Teachers”! Textbooks, homework, detention, lube, dildos…another…

From the makers of 2007’s Best Release “Babysitters”, 2008’s Best Seller & Best Release “Cheerleaders”, and 2009’s 1 hit “Nurses”, comes the bigger, sexier “Teachers”! Textbooks, homework, detention, lube, dildos…another…