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….

Johnny Castle is due for an eye exam and decides to visit the new optometrist, Savannah Stevens. Johnny’s vision is perfectly fine, only he’s more interested in getting up close…

Jemma pays a visit to the plastic surgeons and gets the enhancements she’s been looking for!

Dee Williams is the new stepmom to Oliver Flynn’s girlfriend. And Oliver can’t help but check out her smoking hot bod as she bends over sans panties in his face….

Violet Myers is being interrogated by the police because they have evidence that she has been a very bad girl. The interrogator is to go through any means necessary to…

All the screamin’ hot sex in Digital Playground’s award winning Jack’s Playground series are now shot in POV perspective for your ultimate enjoyment. In Jack’s POV Playground, YOU will get…

Pixie-haired MILF Ryan Keely may be a little out there with her holistic yoga sessions, but at the end of the day she’s just wants to make sure her daughter’s…