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 Digital Playground’s award…

Jack is really busy casting for music videos and now he’s landed Digital Playground’s super fine contract star, Sophia Santi alongside Selina Draagen, Alyssa Chase, Carli Banks, Marlena, Christina Brooks…

Shot entirely on HD, Jack’s Teen America 19 features Jesse Jane and Sophia Santi in intimate and seductive hardcore action! The Jack’s Teen America series arodies beauty pageants and Jack’s…

Jack’s casting again! This time he’s looking for leg models… sexy, leggy vixens who want to be in fresh, up and coming music videos. In volume 3, Digital Playground’s contract…

Jack is really busy casting for music videos and now he’s landed Digital Playground’s super fine contract star, Teagan Presley. She takes a big cock in the butt and we…

Naked Aces is a gorgeous tribute to powerful, sexy women. The A-list cast are frocked in revealing velvet bikinis and sport an arsenal of weaponry. Digital Playground’s contract superstar, Shay…

Shot entirely on HD, Jack’s Teen America 18 parodies beauty pageants and Jack’s lovely contestants all compete for the crown. They take off their clothes, they masturbate, they suck, they…

Jack’s Playground 34 features Digital Playground’s exotic contract superstar, Katsumi. She’s a panty hose model by trade but she’s eager to make the switch to music video queen. She demonstrates…

With six lovely ladies competing for the same title, it’s a tight race to the finish and Digital Playground contract stars, Jana Cova and Lacie Heart, are off to a…

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 and true…

With five lovely ladies competing for the same title, it’s a tight race to the finish and Tiffany is off to a succulent start. She charms the judges and Scott…

“Deeper 3” is beautiful, erotic and cinematic homage to the greatest horror movies ever made. Starring Digital Playground’s contract superstar, Jesse Jane® in 2 twisted and mind-blowing fuck scenes, Deeper…

Jack is really busy casting for music videos and now he’s on the hunt for big, beautiful boobies. They bounce, and they shake. In volume 3 of this delicious show,…

Jack’s Playground 32, features Digital Playground’s contract babe, Sophia Santi, eager to make it in the music video scene. She shows her distinct talents and raw, exquisite beauty in two…

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…

With five lovely ladies competing for the same title, it’s a tight race to the finish and Bree is off to a succulent start. She charms the judges and Scott…

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 shake and Robby finds pleasure deep…

After sneaking off to the private office where he could have the object of his lust all to himself, this young man fucked this posh kimono-wearing girl hard and raw,…

Most teachers don’t want to be in charge of keeping the students out of the condemned old building on school grounds, but Mr. Ichizuka was more than happy to get…

Season 3, hosted by 2015 DP Star winner and contract girl, Aria Alexander! Join judges and industry legends Nikki Benz, Tori Black and Keiran Lee in the search for porn’s…

“Jack’s Playground 31,” the superstar edition, stars the lovely Jana Cova in two delectable scenes, Devon in all her naked splendor and DP’s original contract star, Rocki Roads in brand…

“Jack’s Playground 31,” the superstar edition, stars the lovely Jana Cova in two delectable scenes, Devon in all her naked splendor and DP’s original contract star, Rocki Roads in brand…

“Jack’s Playground 31,” the superstar edition, stars the lovely Jana Cova in two delectable scenes, Devon in all her naked splendor and DP’s original contract star, Rocki Roads in brand…

“Jack’s Playground 31,” the superstar edition, stars the lovely Jana Cova in two delectable scenes, Devon in all her naked splendor and DP’s original contract star, Rocki Roads in brand…

“Jack’s Playground 31,” the superstar edition, stars the lovely Jana Cova in two delectable scenes, Devon in all her naked splendor and DP’s original contract star, Rocki Roads in brand…

“Jack’s Playground 31,” the superstar edition, stars the lovely Jana Cova in two delectable scenes, Devon in all her naked splendor and DP’s original contract star, Rocki Roads in brand…

With five lovely ladies competing for the same title, which girl will take the honors? Will Brooke or Jamie get to deliver their acceptance speech? Did Jack vote for one…

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 his camera….

Jack’s at it again! But this time, it’s professional… and even kinkier than before. Jack turns what he knows best into a career. Welcome to Jack’s answer to getting a…

Jack’s at it again! But this time, he’s focusing in on hot babes with BIG, FUN ASSED… It’s more cushion for the pushin’…. Forget professional… this volume is all about…

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 his camera….

Jack’s at it again! But this time, it’s professional… and even kinkier than before. Jack turns what he knows best into a career. Welcome to Jack’s answer to getting a…

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 his camera….

“Hard Candy” is Robby D’s tribute to gorgeous, young girls and their insatiable and deliciously naughty sex drive. From playgrounds and bubble gum to punk rock and high heels, Robby…

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 his camera….