A fetish vignette unlike anything you’ve ever seen.

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….

News Anchor Johnny can’t get enough of Weather Girl Victoria’s gorgeous ass– he loves it almost as much as she does! As a prank, he puts porn on the green…

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…

He just can’t get enough of his soon-to-be stepmom’s ass, and well, stepmom knows it! She plans a very special Easter egg hunt for her future stepson – with her…

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…

Ms. Olive arrives at an elite masquerade party only to realize that she is the sole guest that Mistress Jasmine has invited.

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…

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….

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….

Charlotte is not your average college student— she’s rich, she’s popular, and she’s the hottest virgin in town! After her best friend Deeana loses her virginity though, Charlotte can’t stop…

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….

Charlotte is not your average college student— she’s rich, she’s popular, and she’s the hottest virgin in town! After her best friend Deeana loses her virginity though, Charlotte can’t stop…

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….

Charlotte is not your average college student— she’s rich, she’s popular, and she’s the hottest virgin in town! After her best friend Deeana loses her virginity though, Charlotte can’t stop…

Janine’s first interracial and NO CONDOM scene!

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….

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….

Blending rock-n-roll with hot chicks and money resulted in Band Camp, the new, musically inspired trip by Digital Playground’s acclaimed director, Robby D. Harmony unravels and tempers flare as budding…

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…

Five horny teens. 2 sound guys with equipment. 1 contest. 1 winner. Sound familiar? It is. It’s Jack’s Teen America.” Put it in and cast your vote! Jack’s at it…

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….

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….

When Sir Keiran learns that Zoey has been slacking in her anal training, he makes sure that her ass is gaping once he’s done with her!

Teagan Erotique is an erotic feast starring Digital Playground’s Teagan Presley with Jesse Jane and Jamie Lynn, Sativa Rose, Nautica Thorn, Jayna Oso, Sandra Shine and Keri Sable. Directed by…

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…

Inside this mansion, the owner hides a secret treasure that both of these burglar goddesses want to get their hands on. Breaking their way in, they discover together that their…

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….