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

Jack’s Playground: Big Tit Show 4. Big Tits, Blonde Chicks Perfect Size For Handy Guys!.

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…

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 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…

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 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…

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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’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!

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…

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…

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….

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 Rick Patrick give…

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…