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….

Texting a lover is one thing, but when it comes to intimacy, nothing tops the touch of skin to skin. With a seductive dance and a naughty look, Foxy Di…

Kate England is looking for a new and unique experience, so she builds a pillory and offers free anal to any guy who is man enough to accept her offer….

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…

Jmac spanked the hell out of his girlfriend’s thick ass, only it was her mom! Ariella Ferrera is used to her daughter’s boyfriends mixing the two of them up, but…

Kali Roses is jogging when she gets stopped by a panicked man who tells her that she can’t look at the sun! He blindfolds her and takes her to a…

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…

Bill is just trying to eat his dinner but his new step mom, Joslyn, has other plans for him. She wants to wrap her lips around his juicy cock and…