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….

Victoria Lawson isn’t sure if she can take the thick dick she’s being presented with. But once she wraps her big lips around it, her pussy starts to water, wanting…

Gypsy and Daisy are all set to have the perfect fourth of July party. When they go to pre-heat the oven though, the only thing that is hot in the…

Uploaded: 2024.03.08 2024 Show more…

Starring Digital Playground’s newest sensation, Shay Jordan and an entire cast of young, gorgeous, almond eyed beauties, Jack’s Asian Adventure will please your pallet. Jack uses the tried and true…

Eden Sin has always had dreams of becoming a star, and even though she just got fucked by a stranger in her raw pussy and now has his jizz all…

Kylie Rocket is training hard with her coach Bruce Venture for her first boxing fight. When Bruce deems Kylie ready, they go to the desk to strategize. Kylie is feeling…

Keiran Lee and his wife were just looking for a relaxing couple’s massage, but they walk into some kind of nude new age hippie massage. Under any other circumstances he’d…