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…

A FantASStic Show Are you ready for some extreme bubble bursting butts?

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 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…

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

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…

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 music videos. This time he gets Alexis Texas and Shyla Stylez to bend over for him. These…

Fucking That Big Dirty Ass. Velvet has proven that her body is a playground for unlimited sexual pleasure. You can stick anything you want anywhere you want and she is…

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…

Hot TS Babes Alice and Skye Enjoy His Big Dick Together Cute Little TS Lee Gets Her Ass Hammered Busty Trans Babe Pleasures Herself Lovely Tatted TS Patti Rides His…

TS Playground 36 Director Jay Sin, the purveyor of fun-loving filth, spotlights alluring she-starlets and decadent delights in “TS Playground 36.” Jay’s keen, creative eye captures playful perversion – tempting…

When Jack puts his mind to something, the filthy possibilities are endless! In Jack’s Playground: Asian Adventure 2, Jack rounds up the most exotic Asians he can find for a…

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…

For the anal connoisseur. Jada dresses like a big girl…to take on her big DP! Goodness Gapeness! Bibi Noel is open wide! Holly Michaels’ Ass…is an anal playground! Trinity St…

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…

Creative pornographer Jay Sin presents sexy, offbeat she-male scenarios in “TS Playground 12.” Bleached blonde and butch, alterna-tranny Danni Daniels dominates skinny Dustin Reeves in a surreal scene — Danni…

Classic Jesse Digital Playground brings you one of the biggest sex icons to ever grace the camera in the beautiful Jesse Jane in what are some of her best classic…

Anally obsessed director Jay Sin and his adventurous cast explore the sensual pleasures of ultra-feminine, fully functional Thai T-girls in ‘TS Playground 22,’ the second ‘Ladyboy Edition’ to date for…

“Anally motivated director Jay Sin focuses on the gender-bending world of she-males in his new “TS Playground 3.” It’s full of gorgeous, feminine transsexuals taking on girls, guys and other…

Featuring Deija Delions! Sexy Camila Loves To Fuck Her Boy Deep! Hung Sabrina And Beautiful Jhenifer Team Up To Fuck Their Boy Toy! Introducing Gorgeous Nadia Aleksandra! Superstar Bruna Butterfly…

The best titty surplus store in town.. With the debut of the series “Titlicious”, Digital Playground introduces a new name in hardcore gonzo entertainment for big tit lovers. Featuring bigger…

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…

Pick Ups And Auditions. Nina Rotti She swallows every drop of L.T.’s load!. Nellie Tiger That pussy gets pounded every which way!. Pocahontas Big phat ass for a monster dick!….

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….

Fresh, Big Asses! Cute little black girls, built like race horses. Their shaved pussies take cock for the team. If you like hot and nasty dark skinned cheerleaders, you’ve cum…

Sodomy specialist Mike Adriano welcomes comely cuties to his backdoor playground in Anal Hotties #3, a tour de of wet, sloppy blow jobs, lewd rimming and sphincter-stretching rectal ravaging! A…

Digital Playground girls are the baddest on the block. Digital Playground’s Bad Girls 2 is the new, kinky gonzo from acclaimed director Robby D. Contract stars Riley Steele and Angelina…

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…

When Jack puts his mind to something, the filthy possibilities are endless! In JACK`S ASIAN ADVENTURE 3, Jack rounds up the most exotic Asians he can find for a wild…