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…

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…

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,…

Jack’s Playground: Big Tit Show 6 Call Jack “The Titty Hunter”. He’s hunting for trophy titties, and will only settle for his favorites; big, beautiful boobies. They bounce, and they…

Katsuni Minx Digital Playground’s Katsuni was the inspiration for this passionate film. Written and directed by Celeste, Minx is based entirely around Katsuni’s own dominant sexual persona and many fantasies…

Jack’s POV 6 All the screamin’ hot sex in Digital Playground’s award winning Jack’s Playground series are now shot in POV perspective for your ultimate enjoyment. In Jack’s POV Playground,…

The Comedy is in the Commentary 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…

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 Playground: Big Ass Show 9 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…

“Eastside Connection” Starring Digital Playground’s newest sensation, Shay Jordan and an entire cast of young, gorgeous, almond eyed beauties, Jack’s Asian Adventure will please your pallet. Jack uses the tried…

Jack Attack Vol. 6 From Digital Playground comes Jack Attack 6, featuring six scenes of couples filming their private moments for your viewing pleasure. Starring Selena Rose, Adrianna Luna, Anikka…

The One and Only 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 more than…

Oops…Jack Did It Again! More D-Cups Are Waiting For You To Unload On! Jack is back and he’s ready to give you more of what you really care about… big…

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…

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…

Girl Next Door Likes It Dirty #26. Want her to get naughty? Just add oil.. Petite but curvy, Kylie’s body is a sexual playground.. When it comes to dick, Kallie…

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…

There is nothing better than a group of beautiful women sharing their most intimate moments. If these beauties don’t get you off, nothing will!

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

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…

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…

Mademoiselle Digital Playground’s sexy and elusive contract star, Sophia Santi plays a sex-inspired Mademoiselle in this lofty production by Robby D. Sophia appears in various states of undress and desire…

Lock. Load. Explode. Naked Aces 2 stars Jesse Jane in a masterful comedy about hot chicks with itchy trigger fingers. The A-list cast are frocked in revealing velvet bikinis and…

Lascivious Liaisons Digital Playground’s luscious Jana Cova plays the head mistress in this kinky, fetish, Hollywood throwback. Director Celeste has created a visual and sexual feast with a super fine…

Jesse Jane Online Exclusive Digital Playground contract star Jesse Jane finds herself infatuated with a budding online relationship, but as the requests become kinkier and stranger, she begins to worry…

This assignment will leave you begging for more. Jesse Jane Homework gets an A+. Another class act from Robby D. and the Digital Playground girls. Jesse Jane leads an ensemble…

Jana Cova Video Nasty Jana Cova and Shay Jordan make crazy-sex together in Digital Playground’s brand new Video Nasty Series. Jana is delicious in three heart pounding, charged scenes, making…

Jack’s Redhead Adventure These Gingers are ripe and ready to show the world that redheads are much more fun in the sack. They’re known for their mercurial tempers; but did…

Jack’s POV 2 All the screamin’ hot sex in Digital Playground’s award winning Jack’s Playground series are now shot in POV perspective for your ultimate enjoyment. In Jack’s new POV…

Jack’s POV 14 With its unique camera work, Jack’s POV 14 brings you into the action and doesn’t loosen its grip until you’re completely drained. Jack’s POV 14, starring Digital…

Real Girls Uncensored You don’t know Jack until you’ve seen through his eyes. Don’t miss this all-star cast that includes Hannah Harper, Lacey Maguire, Annette Schwarz, Rachel Roxxx & Britney…

Jack’s POV 10 Don’t miss Digital Playground’s Exclusive Contract Stars, Teagan Presley and Jana Cova in a very personal, off the hook sexual experience. All the screamin’ hot sex in…

Jack’s Asian Adventure 2 Always A Happee Ending! You like partay?’Playful, powerful and supremely sexual – a revolutionary sex comedy. . . One of the most original series in years!…

Jack’s POV 9 Don’t miss Digital Playground’s exclusive contract star, Stoya in her debut boy/girl scene. Jack’s POV 9 is off the hook sex! All the screamin’ hot sex in…

Jesse Jane Kiss Kiss Starring Digital Playground contract superstars Jesse Jane and Stoya, Kiss Kiss documents very sexy and private encounters taking place in the suburbs of a bustling tourist…

Jesse Jane Scream Enjoy Digital Playground contract star Jesse Jane in this wonderful and sexy horror spoof. Set in another era, 6 erotic stories unfold in an eerie mansion. It’s…

Girls Just Want To Have Fun Raven Alexis arrives in the land of opportunity to escape from an abusive lover. Her innocence and girl-next-door looks are only a disguise as…

Raising Your Temperature is Their Specialty. From the studio that brought you blockbusters “Babysitters” & “Cheerleaders”, Digital Playground presents its 3rd installment of the hit vocation series. The sexy nurses…

Stoya Scream Visionary director Celeste takes viewers on a pulse pounding journey of sex and fear featuring Stoya, 2008’s Best New Starlet. Stoya: Scream is set in another era, 6…