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….

Did Adriana Sephora honestly expect, when she went for an afternoon nap in her finest new pair of lingerie, that her girlfriend Celeste Star would pass up a chance to…

Bodacious bombshell Phoenix Marie gets drenched in oil and shows off her ample assets before getting her thick, juicy ass pounded by Small Hands.With these two wet and wild performers…

Secretary Giselle has a run in her stockings – during a very important client meeting. When she’s caught changing her pantyhose in the company conference room, she must be disciplined…

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Danica Dillon is substitute teaching etiquette at a local all girl’s private school, and she’s come prepared. Rocking a suitcase full of dildos, Danica tries to teach those slutty schoolgirls…

Ashley Lovebug knew she would have fun at this party. First off gay sex turns her on and secondly she gets to play with two dicks instead of one! See…

In this self-shot sex documentary series from some of the biggest names in the business, Digital Playground gets up close and personal, offering you a behind-the-scenes look at what it’s…

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…

While Timo was getting ready for work this morning, he found a note from Foxy Di telling him she wanted to get hot and heavy before he left for work….