Sorry about Jack’s 20, folks. I bitchslapped Jack to make sure that won’t happen again.

Jack’s POV You don’t know Jack until you’ve seen it like this. All the screamin’ hot sex in Digital Playground’s award winning Jack’s Playground series are now shot in POV…

Jack’s POV 6 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,…

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 14 With its unique camera work, Jack’s POV 14 brings you into the action and doesn’t loosen its grip until you’re completely drained. Jack’s POV 14, starring Digital…

Ride The Curves With Reckless Abandon Jack is really busy casting for music videos and he’s scored some super fine ass for volume 38. Digital Playground’s amazing contract super stars…

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…

“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 Playground: Asian Adventure 4 Digital Playground’s Asian sensation, Shay Jordan is back for more… with a cast of eager-to-please, exotic nymphs, Jack’s Playground: Asian Adventure 4 will surely satiate…

Jack’s POV 15 With its unique camera work, Jack’s POV 15 brings you into the action and doesn’t loosen its grip until you’re completely drained. Jack’s POV 15, features Digital…

Save the best for last. In the ninth installment of Jack’s Big Tit Show, Jack is on the hunt for big, beautiful boobies, using his trusty music video ploy to…

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…

Jack’s Playground: Big Tit Show 4 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…

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…

My First Porn The My First Porn series is a comical sex-spectacle of Jack directing his first porn movie. Digital Playground and Robby D. are proud to present The A-list…

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…