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…

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…

That’s right!… Best gonzo series muthafuckas!!! To celebrate, we added a bootylicious sista to commemorate da festiviteez.

Numba nine, numba nine, nine titties, nine inches, nine pussies…I said nine mutha fucka! Oh yeah…and nine money shots!

Save the best for last! Jack says dee cups will surely keep you up!

Blu-Ray Version. 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…

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,…

Real Girls Uncensored You don’t know Jack until you’ve seen through his eyes. Don’t miss this all-star cast that includes Hannah Harper, Lacey Maguire, Annette Schwarz, Rachel Roxxx & Britney…

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 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: 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 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…

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…

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…

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 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…

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…

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…

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…

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…

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…