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 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…

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…

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…

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…

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…