“Trick o’ treat… Jack wants to lick some pretty meat. And Montel ain’t got nuttin’ to say ’bout dat!”

Lets take a moment and give thanks for the sweet teens in Jack’s Playground 16.

Jack’s Playground is a brand new reality series featuring Jack, a trust fund child and aspiring music video director who happens to have a knack for persuading real girls to…

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 the second volume, Digital Playground’s…

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…

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 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 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…

Come and play with us. Again Seventeen’s most beautiful models are invited to play. The misbehave themselves in all kind of places making usa of sex toys, their horny girlfriends…

When Jack puts his mind to something, the filthy possibilities are endless! In Jack’s Playground: Asian Adventure, Jack rounds up the most kinky, exotic Asians to give him a happy…

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…

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!

Digital Playground’s Asian sensation, Shay Jordan is back for more… with a cast of eager-to-please, exotic nymphs, Jack’s Playground: Asian Adventure 4 will surely satiate because these young hotties were…

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…

TS Playground 26 In TS Playground 26, outrageous director Jay Sin combines gender-bending transsexual erotica with extreme anal perversion: Four femme, functional T-girls take on adventurous studs for butt fucking,…

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…

In TS Playground 24, distinctive director Jay Sin spotlights feminine, fully functional trans beauties in solo sessions and gender-bent trysts with adventurous, hung studs. Tanned TS Bruninha Almeida joins Spencer…

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…

TS Playground 9

Welcome to Rubber Playground, DDF’s latest playground of sexuality and deep desire. Discover the pleasures of dominance and submission. Unleashing your inner master or slave can be a liberating experience…

Director Jay Sin’s TS Playground video line captures beautifully femme, hotly functional T-girls in every kind of action.

“Director Jay Sin’s ‘TS Playground’ video line captures beautifully femme, hotly functional T-girls in every kind of action. ‘TS Playground’s Best Of TS On Female’ collects the series’ hottest hook-ups…

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…

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…

“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…

“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 Bachelorette Party – The Brides Bodyguard You’re her bodyguard, the one man paid to keep his hands to himself. But this weekend? Temptation comes dressed to kill. Candee’s bachelorette…

Share My Boyfriend Vol. 16 House Party Hotties: We’ve all woken up after a crazy night, wondering how the hell we got there. But you never really expect to have…