Jack’s Playground: Big Ass Show 9 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…
A FantASStic Show Jack’s Big Ass Show is back with another episode, and although Jack isn’t getting anything once again it seems like where ever he goes there’s girls with…
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: 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….
Save the best for last. In the ninth installment of Jack’s Big Tit Show, Jack is on the hunt for big, beautiful boobies, using his trusty music video ploy to…
Jack’s Playground: Big Tit Show 6 Call Jack “The Titty Hunter”. He’s hunting for trophy titties, and will only settle for his favorites; big, beautiful boobies. They bounce, and they…
The One and Only 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 more than…
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: Big Tit Show 7 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…
Got D’s? Some More Juice For You To Squeeze. Jack is really busy casting for music videos and now he’s on the hunt for big, beautiful boobies. They bounce, and…
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…
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 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…
Real girls uncensored. Jack is really busy casting for music videos and now he’s landed Digital Playground’s super fine contract star, Jesse Jane. She fucks Ben English every which way…
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…
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…
Lock, Load, Explode. 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…
Jesse Jane Image Jesse Jane: Image explores the famous and undeniably sexy image of Digital Playground superstar, Jesse Jane. Her playful fantasies are fulfilled in 4 amazingly provocative scenes. Watch…
Jesse Jane Breathe Me No regret in sex and life is the theme of director Celeste’s latest modern fuck story, Jesse Jane: Breathe Me. Superstar Jesse Jane is determined to…
Jack’s Redhead Adventure These Gingers are ripe and ready to show the world that redheads are much more fun in the sack. They’re known for their mercurial tempers; but did…
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…
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…
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…
Janie Summers Private Lessons Director Robby D. is back, and this time he’s introducing us to Janie Summers, the new newest addition to the Digital Playground beauties. Janie and her…
