Oops…Jack Did It Again! More D-Cups Are Waiting For You To Unload On!. This show is full of 2-many delicious babes, 2-many horny humpers, and 2-many big boobies bursting out…

“The playground keeps getting better with new hot pussy. This could be the sexiest of the series! Just load up, and get ready for the wet target!”

“Lets listen to these cummentators discuss their thoughts on Jack’s bitches.” And cut the farting.

Analizar Esto Maricon … Did I just speak Spanish?

Montel’s back in da house! What’s da assfuckathon?

Sorry about Jack’s 20, folks. I bitchslapped Jack to make sure that won’t happen again.

Give To The Yummypie.com Telethon

Cousin Nick P., Ph.D., drops knowledge on what it’s like to cut these muthafuckas.

Choc full o’ fun and flavor!

Watch Tera take the double Buda! See Rocki take it in the… barn… and will Tommy ever pop?

Jack be Nimble. Jack be Quick. Jack be Back Muthafucka.

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

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 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…

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…

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 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…

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…

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…

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…

My First Porn 10. The My First Porn series is a comical sex-spectacle of Jack directing his first porn movie. Volume 10 is over 2 hours and features Stoya in…

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…