Jack’s at it again! In his playground, Jack is busy casting for music videos. The delicious girls will do ANYTHING for stardom! Some suck, some fuck, some masturbate but they…

Slavic stunner Sybil Kailena can’t find the perfect outfit for Mary Kalisy’s birthday bash. She has emptied her bedroom closet and tried on every sexy garment in there. But each…

I (Luke Longly) pull my step-sister into my parent’s bedroom, because I’m trying to quickly fuck her without my step-mom catching us! I have never had sex before so I’m…

For the first time in Digital Playground history, we will be hosting a nationwide search to find the next DP Star. We were accepting video submissions for the entire month…

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….

The Ski Team is super stoked to hit the slopes – until they realize their broke ass ski coach has pawned their equipment over the summer. These ski babes will…

When it comes to sex, Brandi Love knows a thing or two. Who better to teach you how to fuck than a mature milf? This stepmom’s big tits and hands-on…

Uploaded: 2024.02.23 2024.02.22 Show more…

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….