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…

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…

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…

Jack’s Playground: Big Tit Show 8. 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…

Passionate & playful, because a girl knows best! Tune in for 4 brand new scenes in this edition of A GIRL KNOWS, the most erotic girl-only action captured through amazing…

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…

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…

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…

Director Jay Sin, the master of playfully nasty anal pornography, turns his camera toward the exotic world of glamorous T-girls and the kinky dudes that love them: TS Playground 25…

Kinky porn pioneer Jay Sin has won ass-obsessed hearts through an amazing career of documenting extreme rectal perversity with the most anally acrobatic ladies in the game. His explosive she-male…

From the master of extreme anal erotica, director Jay Sin, comes a showcase of sultry, feminine starlets sporting huge, throbbing she-cocks! The luscious ladyboys of “TS Playground 23” get off…

(A) Is For Asses Enjoy some of the hottest asses on some of the sexiest stars in the biz showcasing their rumps in scenes taken from Digital Playgrounds best titles….

“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.Riley Steele HoneyRiley Steele…

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.All is fair in…

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.Lost In A Game…

An All New 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 7 features…

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.Stoya Heat”Stoya: Heat” is…

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…

Dogg Piled: Swinger MILF Gangbangs Big butt swing wife MILF, Gracie Playground, was nice enough to show up to her video shoot with her hubby, Brick. Dogg invited over a…

1st Ever T-Girl Adult Parody! Loosely based on the pilot episode of the hit TV show, This Is Definitely Not Ugly Betty: A XXX Tranny Parody starts at the beginning….

You’ve loved Hannah in everything and now you can enjoy her work as you never have before, with all the production values Digital Playground is famous for. Hannah Harper is…

Digital Playground’s contract superstar, Sophia Santi is a sexual freak and she proves it in this erotic masterpiece. With new direction and casting by Celeste, the Sexual Freak series has…

From the deviant mind of Digital Playground’s director Celeste comes Shay Jordan: Slippage. Full of tight ropes, delicious tease, and wet pussies, Shay Jordan: Slippage stars Digital Playground contract girl…

Naked Aces 5 is the debut film for Digital Playground’s brand new, ultra-hot contract girl, Riley Steele, and she shows the world her pure star power in a passionate, almost…

Five average guys are wandering through Malibu in search of a mansion where the All-Stars play, a group of the hottest women known to man. They are on the age-old…

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…

Luscious Digital Playground superstarlet Selena Rose signs up for one-on-one boxing lessons from James Deen. What she doesn’t know is that her “coach” is a fake! James and his buddies…

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 new POV Playground, YOU will…

Gabriella Fox Foxxxy Gabriella Fox, Digital Playground’s sultry Latina contract girl, stars in three of six scenes of the must-own “Gabriella Fox: Foxxxy”. The gorgeous starlet loses all her inhibitions…

Erotique is a unique, stylized vignette film by acclaimed director, Nic Andrews. This underground, erotic-fetish adventure is a showcase for the sexuality and sensuality of Digital Playground’s contract star, Jesse…