Jack’s at it again! But this time, it’s professional… and even kinkier than before. Jack turns what he knows best into a career. Welcome to Jack’s answer to getting a…

When Keiran’s girlfriend falls asleep during a long road trip, Keiran decides to pick up a mysterious hitch hiker. At first, she agrees to stay in the bed of the…

Thihiro Takizawa has a crush on a guy, but she is too inexperienced to do much about it. When he shows up in the locker room making sexual advances, Thihiro…

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Flexible and fit Emily Blacc shows off her moves for Ryan outside in the yard. With her short shorts and perky tits out she teases his cock before getting on…

We love Chanel Preston and her perfect curves. And it’s clear she loves us back by the way she shows off her thick yet tight body for us in a…

Jack is really busy casting for music videos and now he’s on the hunt for big, beautiful butts. They bounce, they roll and they shake and Robby finds pleasure deep…

Jade Maris and Liz Jordan are both dick obsessed. The girls are just doodling when Jade’s stepbrother Juan Loco comes in and announces he’s bored. He asks the girls if…

Xander and his friend are bored and decide to check out a porno theatre. Imagine their excitement when a mysterious woman walks in, sits in the front row, and starts…

Spend an amazing day with the most gorgeous girlfriend ever, Lia Lin. You can enjoy an incredible girlfriend experience from the moment you wake up next to Lia, until the…

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…

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…