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…
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…
Got D’s? Some More Juice For You To Squeeze!. “Jack is back with another excellent show focusing on girls with impressive D-cups. There are plenty of titty fucking and pussy…
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…
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 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…
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…
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…
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…
Shay Jordan: Slippage 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…
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….
Porcelain Jana Cova is Porcelain. This intimate and artful production shines new light on Digital Playground’s exclusive contract super star, Jana Cova. In this glamorous and smart vignette, director Celeste…
Stagnetti’s Revenge ** 2009 AVN Award Winner – Best Video Feature** **2009 AVN Award Winner – Best Director: Film, Joone ** 2009 AVN Award Winner – Best Actor, Evan Stone…
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…
Fuck Me Silly Vol. 2 Introducing Nicolette Shea to DP. Watch her get soaked with busty brunette Angela White and of course, the man himself – Keiran Lee. Ariel can’t…
Deeper 11 Beginning with the first frame and continuing until the final credits roll, Deeper 11 is an intense sexual experience. Deeper 11 embarks on a journey, deep inside Digital…
Deeper 10 Beginning with the first frame and continuing until the final credits roll, Deeper 10 is an intense sexual experience. Deeper 10 embarks on a journey, deep inside Digital…
Body Heat 2011 AVN Award winner for: Best All-Girl Group Sex Scene Fire has never been so hot since these sexy firefighters took over the station. Dangerous explosions, life or…
All is fair in love and weddings. Ever what happens when best girlfriends come together to share a special moment: a wedding day? Absolute madness, apparently, and they simply can’t…
Stoya Heat Stoya: Heat is an astounding platform for superstar Stoya to lose all inhibitions and throw herself completely into a world of sex and desire. There is no denying…
Ghostbusters XXX: A Porn Parody Cosplaygrounds sixth original production takes on one of the biggest franchises in cinematic history with Ghostbusters XXX: A Porn Parody. Coinciding with the release of…
X-Men vs. Thor XXX: A Porn Parody Let’s face it, in the world of mutants, it’s really no picnic being Rogue, as the amazing Abigail Mac shows us in Cosplayground’s…
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…
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….
