Jack turns 1!…and there’s a whole lotta frosting on deez cakes!

Dr. Hienrich Shizen sez, “Zarez nutting unlucky about zee numba 13…unless you’re zee one taking zee 13 eenchez.”

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

“Trick o’ treat… Jack wants to lick some pretty meat. And Montel ain’t got nuttin’ to say ’bout dat!”

Lets take a moment and give thanks for the sweet teens in Jack’s Playground 16.

Jack’s Playground is a brand new reality series featuring Jack, a trust fund child and aspiring music video director who happens to have a knack for persuading real girls to…

A FantASStic Show Are you ready for some extreme bubble bursting butts?

Teagan Presley & ANAL, does the rest of this description even matter? Jack is really busy casting big, bouncing, beautiful butts for music videos. They shake, they roll and they…

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 the second volume, Digital Playground’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 Jack’s Playground: Leg Show 3,…

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 to the pink treasure nestled…

Mega Packed with Juicy Crack “Check out these packs with juicy crack presented by Jack”

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! Some suck, some fuck and some…

Big, Hot and Kinky! “More Cushin For the Pushin”

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…

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 Jack finds pleasure deep…

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 Jack finds pleasure deep…

When Jack puts his mind to something, the filthy possibilities are endless! In Jack’s Playground: Asian Adventure, Jack rounds up the most kinky, exotic Asians to give him a happy…

When Jack puts his mind to something, the filthy possibilities are endless! In Jack’s Playground: Asian Adventure 2, Jack rounds up the most exotic Asians he can find for a…

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 to bend over for him. These…

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

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 because these young hotties were…

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…

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, get the BEST…

You think you know Jack? These bitches are sucking up his dick and swallowing it deep in their pussies… I think they know a little more about Jack than you…

Jack’s Ultimate Asian Adventure. Digital Playground brings you over three hours of some of the sluttiest and hottest Asians ever filmed. These Oriental beauties will give you a new meaning…

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 Playground’s beautiful contract…

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…

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 Stevens in a…

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 Digital Playground’s award…

Beautiful BiBi Jones drips her young, sweet juices all over thick rods and long, hard members. She shows off her naughty skills as the youngest new nasty girl. She and…

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 perspective for…

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 new POV Playground, YOU will…

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…

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…

Creative pornographer Jay Sin presents sexy, offbeat she-male scenarios in “TS Playground 12.” Bleached blonde and butch, alterna-tranny Danni Daniels dominates skinny Dustin Reeves in a surreal scene — Danni…

Got Long Legs? Just Wait Until It Opens! Jack’s casting again! This time he’s looking for leg models… sexy, leggy vixens who want to be in fresh, up and coming…

When Jack puts his mind to something, the filthy possibilities are endless! In JACK`S ASIAN ADVENTURE 3, Jack rounds up the most exotic Asians he can find for a wild…

“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…

2 seconds will be deducted from your Pay-Per-Minute time for every second watched.Premium PPM allows us to bring you the best Adult content from the hottest studios.A Digital Playground original…