Jack’s Playground is a collection of Jack’s personal videos, homemade in Santa Monica, California showcasing his uncanny ability to persuade girls to perform sexual acts in front of his camera….

Student Eva Lovia is leaving for boarding school in France. As she breaks the news to her boyfriend, this might be their last night together. A final farewell fuck before…

The skies are a whole lot friendlier when a group of the world’s most beautiful stars pose as slutty flight attendants and sneak onto a plane to shoot a reality…

After Keiran Lee spies on his brother’s wife, Kendra Spade, have a sexy, soapy bubble bath, Kendra grabs a razor and makes a move to shave off her beautiful bush….

Get an up close and personal look at Phoenix Marie’s sexy, barefooted at-home workout. Phoenix teases you by showing off some of her favorite exercises, before deciding that her pussy…

Evelyn Claire comes home to a special surprise from her boyfriend, Seth Gamble. He planned a super special evening for Evelyn, complete with wine, snacks and hanging lights to get…

This cute little Asian girl with a short hairstyle and tiny titties loves getting tied to this pink chair as her male friend spreads her pussy apart with two fingers….

In its glory days, Lenina Crowe’s free-use hotel (where a customer could have sex with any employee they desired) was a beloved, happening establishment full of potential. Today, it’s but…

Shayna is too young to grasp the irony of the pink walls surrounding her as TT Boy hammers home his hog in her pink rose bush. She only sees the…

A cozy afternoon on the couch turned into something much steamier when Ryan Ryans couldn’t keep her hands off her girlfriend’s body. Shyla Jennings tried as much as she could…

Jack’s Playground 34 features Digital Playground’s exotic contract superstar, Katsumi. She’s a panty hose model by trade but she’s eager to make the switch to music video queen. She demonstrates…