Jack is really busy casting for music videos and now he’s landed Digital Playground’s super fine contract star, Sophia Santi alongside Selina Draagen, Alyssa Chase, Carli Banks, Marlena, Christina Brooks…
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…
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…
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…
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 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…
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…
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…
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…
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…
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…
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…
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…
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…
“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…
