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….

Winter Jade has some shocking purple hair and an even more shocking sexual tension that she wants to get out! She swirls her cute petite body around and strips down…

Jack’s Playground 33, features Digital Playground’s one and only insatiable and sexy Devon. She’s eager to make the music video cut and demonstrates her distinct talents on Scott Nails’ throbbing…

Jill Kassidy has to spend a whole weekend with her busty stepmom Lela Star and neither of them wants to be there. But the fact that the concierge, Keiran Lee,…

When Sean moves into his new neighborhood, it doesn’t take long for him to be welcomed by the sexy neighborhood slut Eva. She brings a whole new meaning to the…

With six lovely ladies competing for the same title, it’s a tight race to the finish and Digital Playground contract stars, Jana Cova and Lacie Heart, are off to a…

Cleo Vixen is a naughty teen who’s already transferred schools once, and the university dudes have already banged her pussy a few times, but something she’s new to is porn….

Tyler gets tricked by these guys out at the pool. They offer to help her with the suntan lotion and she agrees before finding out that they meant the high…

This slutty Asian is rubbing her clit through her clothes. Her man comes in and catches her on the couch so she peels off her shirt to let him play…