TS Playground 27 Director Jay Sin spotlights the sexiest trans talent from Brazil and the U.S. in TS Playground 27. Femme but very functional beauties tease the camera with their…

Katsuni Video Nasty Katsuni makes crazy-sex and delivers superb anal scenes throughout Digital Playground’s fourth installment of Video Nasty. She proves her pure and delicious nastiness in a sexually charged…

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…

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….

“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: 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…

Fast and furious. The need a deep, hard drilling and power fucking is the only way to go! Beautiful Jesse Jane and sultry, sexy Stoya gear up for an explosive…

Lascivious Liaisons Digital Playground’s luscious Jana Cova plays the head mistress in this kinky, fetish, Hollywood throwback. Director Celeste has created a visual and sexual feast with a super fine…

Jack’s Redhead Adventure These Gingers are ripe and ready to show the world that redheads are much more fun in the sack. They’re known for their mercurial tempers; but did…

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…

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…

A Fun And Sexy Series That Tries Really Hard To Fit In The My First Porn series is a comical sex-spectacle of Jack directing his first porn movie. Volume 11…

Raising Your Temperature is Their Specialty. From the studio that brought you blockbusters “Babysitters” & “Cheerleaders”, Digital Playground presents its 3rd installment of the hit vocation series. The sexy nurses…

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…

Extra credit never felt so good. Everyone remembers their academic life; textbooks, homework, detention, lube, dildos…another typical day at Filmore Bush Academy, where Sex-Ed is a hands-on class. Digital Playground’s…

Shay Jordan’s Juice Director Celeste showcases the stunning Shay Jordan at her juiciest best. Shay Jordan Juice is an amalgam of a dizzying frenzy of tantalizing flesh and mouthwatering fucks….

Sexual Freak 7 Digital Playgrounds contract superstar Stoya is a sexual freak and she proves it in this erotic masterpiece. With Celeste at the helm, the Sexual Freak series has…

Fly Girls The skies are a whole lot friendlier when a group of the world’s most beautiful porn stars pose as slutty flight attendants and sneak onto a plane to…

Bring your sleepover bag Bring your pajamas because Digital Playground brings you Secret Sleepover, and the sexy slumber party is about to start. Seductive Selena Rose looks after her boss,…