Jack’s Playground: Leg Show 4 The camera starts at her petite ankle and slowly travels up the milky skin of her calve and around her toned hamstring on a journey…

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 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…

Jack’s Playground: Leg Show 4 The camera starts at her petite ankle and slowly travels up the milky skin of her calve and around her toned hamstring on a journey…

Choc full o’ fun and flavor!

“Exotic waves of molten cum erupt into timid young glesh in this amazing exploitation of carnal voracity”

We be on numba Foh, and dis be Montel’s Wah so deal wit dat you muthafucka!

“Dis one be off da hinges wit lots of titayz and all kinds of juicy young ass.”

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 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 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 Asian Adventure 2 Always A Happee Ending! You like partay?’Playful, powerful and supremely sexual – a revolutionary sex comedy. . . One of the most original series in years!…

You Don’t Know Jack Until You’ve Seen Through His Eyes. All the screamin’ hot sex in Digital Playground’s award winning Jack’s Playground series are now shot in POV perspective for…

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…

Jack Attack Vol. 6 From Digital Playground comes Jack Attack 6, featuring six scenes of couples filming their private moments for your viewing pleasure. Starring Selena Rose, Adrianna Luna, Anikka…

Oops…Jack Did It Again! More D-Cups Are Waiting For You To Unload On! Jack is back and he’s ready to give you more of what you really care about… big…

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…

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…

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…

“Anal explorer Jay Sin continues his journey into an exotic, hidden sexual world in his new lady-boy adventure, “TS Playground 4.” Jay’s signature style of sexy costume play and fantastic…

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…

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…

6th Annual Tranny Awards: The Winners. 6th Annual Tranny Awards: The Winners is directed by Blackula. The performers in this movie won awards at the most recent Tranny Awards in…