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…
Jack’s Playground: Big Tit Show 8 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…
Teagan Presley & ANAL, does the rest of this description even matter? Jack is really busy casting big, bouncing, beautiful butts for music videos. They shake, they roll and they…
Jack’s Playground: Big Tit Show 6 Call Jack “The Titty Hunter”. He’s hunting for trophy titties, and will only settle for his favorites; big, beautiful boobies. They bounce, and they…
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…
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…
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 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….
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…
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…
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…
My First Porn 8. The My First Porn series is a comical sex-spectacle of Jack directing his first porn movie. Volume 8 is 3 full hours and features Digital Playground…
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…
My First Porn 2 The My First Porn series is a comical sex-spectacle of Jack directing his first porn movie. Enjoy some first-class, good time Digital Playground humor interlaced between…
Teen America: Mission #23 Jack knows ambitious chicks will do anything to win first place in a beauty pageant. Jack’s Teen America: Mission #23 features Jack and his crew interviewing…
Cockasian 4 Acclaimed gonzo director Robby D. rounds up the sweetest, little Asian hotties around and talks them into taking giant dicks deep inside their tasty fortune cookies. Cockasian 4…
