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,…

Hot Babes, Bangin’ Sex, And Nasty Jack… Jack’s Playground 31, the superstar edition, stars the lovely Jana Cova in two delectable scenes, Devon in all her naked splendor and DP’s…

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…

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…

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…

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…

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…

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…

Came as a girl, left as a woman! From the playground to my sheets, Addison is a true slut! Allie is a fine “art” piece and painted her ass full…

A Digital Playground XXX Parody Gerald hasn’t visited his quirky father, Mr. Fucker, and his new, young, smokin’ hot wife, Mrs. Fucker, in ages. In an attempt to tighten familial…

A Digital Playground Original Series – 6 Episodes After getting his ass whooped, Santa asks three guys – Tom, Dick, and Harry to save Christmas by using his magical suit….

Loaded Digital Playground’s Loaded tells a fast-paced story about cold-blooded killers, detectives and witnesses, all working against the clock. The action on one day of filming alone was so intense…

Fly Girls The skies are a whole lot friendlier when a group of the world’s most beautiful porn stars pose as slutty flight attendants and sneak onto a plane to…

Gabriella Fox Sexy Hot Directed by Celeste, Gabriella Fox Sexy Hot captures Digital Playground’s fresh new star, Gabriella Fox in two indescribably delectable and ultra-horny scenes. The Sexy Hot series…

Anal Teens From Russia #5 Evil Playgrounds specializes in consistently bringing you the hottest and sexiest talent from Russia! These young Russian sluts are ready to be fucked in the…

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…