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,…
“Montel’s War” 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…
Cumless: A Digital Playground XXX Parody Charlotte is not your average college student – she’s rich, she’s popular, and she’s the hottest virgin in town. After her best friend Deena…
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…
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…
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…
Wednesday XXX: A Porn Parody Duh-nuh-nuh-nuh. Snap. Snap. While the rest of The Addams Family might be creepy, kooky, mysterious, spooky, and altogether ooky, but Wednesday Addams has long been…
Sexual Fantasies 13 ** Locked Out Lust**: Gorgeous Arya Fae is on a date with Ryan Mclane and can’t wait to show him her place. They two are touching and…
POV Perfection Vol. 2 Up close and personal encounters with the busty bombshells that we all want a piece of. You will get the best action, the most delicious tease…
Blonde Bombshells Digital Playground’s best golden beauties. . Hot Blonde in Black Fishnets Nikki Benz Takes a Big Cock from Behind – Duration: 16 min – Starring: Nikki Benz Busty…
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…
Fuck Me Silly Vol. 2 Introducing Nicolette Shea to DP. Watch her get soaked with busty brunette Angela White and of course, the man himself – Keiran Lee. Ariel can’t…
A Digital Playground Original Series The ladies of sorority Delta Pi Chi just moved into the neighborhood and the community is not thrilled! These sex-crazed sorority sisters party loud and…
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…
