Real girls uncensored. Jack is really busy casting for music videos and now he’s landed Digital Playground’s super fine contract star, Jesse Jane. She fucks Ben English every which way…
A FantASStic Show Jack’s Big Ass Show is back with another episode, and although Jack isn’t getting anything once again it seems like where ever he goes there’s girls with…
Jack’s Playground: Big Tit Show 7 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…
Jack’s Redhead Adventure These Gingers are ripe and ready to show the world that redheads are much more fun in the sack. They’re known for their mercurial tempers; but did…
Jack’s POV 16 All the screaming 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,…
Jack’s POV 10 Don’t miss Digital Playground’s Exclusive Contract Stars, Teagan Presley and Jana Cova in a very personal, off the hook sexual experience. All the screamin’ hot sex in…
The Comedy is in the Commentary 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…
Jack’s Playground: Big Ass Show 9 Jack’s busy in his playground casting big-ass babes for leading roles in his “music videos”. This time he gets Alexis Texas and Shyla Stylez…
Jack’s Playground: Big Ass Show 4 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…
Jack’s Playground: Big Ass Show 2 Jack’s busy in his playground casting big-ass babes for leading roles in his yet-to-be-seen music videos. The delicious girls will do anything for stardom….
“Eastside Connection” 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…
Jack’s POV 9 Don’t miss Digital Playground’s exclusive contract star, Stoya in her debut boy/girl scene. Jack’s POV 9 is off the hook sex! All the screamin’ hot sex in…
The One and Only Jack is really busy casting for music videos and now he’s on the hunt for big, beautiful boobies. They bounce, and they shake. There’s more than…
Got D’s? Some More Juice For You To Squeeze. Jack is really busy casting for music videos and now he’s on the hunt for big, beautiful boobies. They bounce, and…
Jack Says, “Big Tits Are More Nutritious.” Jack’s at it again. In his playground, Jack is busy casting for music videos. The delicious girls will do anything for stardom. Some…
An All New Series That Tries Really Hard To Fit In.. The My First Porn series is a comical sex-spectacle of Jack directing his first porn movie. Volume 7 features…
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…
Sexual Freak 8 Digital Playground’s best selling Sexual Freak line is proud to offer up Audrey Bitoni in all of her gorgeous, freaky splendor. This exotic brunette delivers her best…
A Fun And Sexy Series That Tries Really Hard To Fit In The My First Porn series is a comical sex-spectacle of Jack directing his first porn movie. Volume 11…
My First Porn 9 The My First Porn series is a comical sex-spectacle of Jack directing his first porn movie. Volume 9 is over 2 hours and features Teagan Presley…
