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

Jack’s Playground: Big Tit Show 6. Big tits are more than a handful. They’re two..

The One and Only. It’s Time For a Titty Smackdown!.

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…

Jack’s Playground: Big Tit Show 7. Big tits are more than a handful. They’re Two!.

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 4. Big Tits, Blonde Chicks Perfect Size For Handy Guys!.

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…

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…

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…

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 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…

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

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

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 yet-to-be-seen music videos. The delicious girls will do ANYTHING for stardom! Some suck, some fuck and some…

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!

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…

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…

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…

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…

“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…

1.5 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.Ghostbusters XXX: A Porn…

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.Janie Summers Private LessonsDirector…

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…

Pornstar Confidential 3 Get to know your favorite stars from Digital Playground. Go behind the scenes and meet some of the sexiest girls in the biz as they answer intimate…