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…

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…

Save the best for last! Jack says dee cups will surely keep you up!

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,…

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…

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…

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…

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…

SWAMEBUS Debarque A Tenerife! New crew, new vibes, and a volcanic island as your playground: welcome to this new season, which promises to be hotter than ever. The craziest content…

Virgin Threesome Party 3 Two girls for every boy and they’re boys alright with the girls taking control, slamming their holes on the guy’s faces then the other hops on…

Russian Blonds Have All The Fun 2 Young, blonde, and full of fun.

Beetlejuice XXX: A Porn Parody – Part 1 There’s nothing more relaxing than a vacation in a nice modern house with an artsy aesthetic and Rachael Cavalli is ready to…

Beetlejuice XXX: A Porn Parody – Part 2 Tommy Pistol’s title character is finally unleashed and he turns out to not only be the world’s pre-eminent -exorcist, he’s quite the…

X-Men vs. Thor XXX: A Porn Parody Let’s face it, in the world of mutants, it’s really no picnic being Rogue, as the amazing Abigail Mac shows us in Cosplayground’s…

Dirty CopsCan a dirty cop ever be redeemed? Up-and-coming officers Bishop and Jones (Nicole Kitt and Alex Jones) are looking to make names for themselves within the police , but…

2.5 seconds will be deducted from your Pay-Per-Minute time for every second watched.Premium PPM allows us to bring you the best Adult content from the hottest studios.Payback’s A BitchA woman…

Hard Loving Teens 4There is no such thing as too hard!

Anal Pleasure For My Cheating MILF Vol. 1Scene 1: Black Angelika – Fuck Me Through On Our Playground.Black Angelika, a big-breasted hot woman, wears only a sexy baby doll with…

2 seconds will be deducted from your Pay-Per-Minute time for every second watched.Premium PPM allows us to bring you the best Adult content from the hottest studios.Some Tales Should Never…

Once upon a time in the West, there were four badass bitches… Co-produced by Wicked Pictures and Adam & Eve, Stormy Daniels’ epic western saga Wanted is set in 1879…

1.5 seconds will be deducted from your Pay-Per-Minute time for every second watched.Premium PPM allows us to bring you the best Adult content from the hottest studios.

2 seconds will be deducted from your Pay-Per-Minute time for every second watched.Premium PPM allows us to bring you the best Adult content from the hottest studios.Angelina Armani The Big…

Russian Anal Sweethearts 3Young Russian cuties get their tight, firm little asses pounded!!!

2 seconds will be deducted from your Pay-Per-Minute time for every second watched.Premium PPM allows us to bring you the best Adult content from the hottest studios.11 beautiful girls. 1…

In A GlimpseIn a glimpse uniquely depicts the glamour of allure and style which is the exclusive playground of the rich and famous. Taking place in the sweltering heat of…

2 seconds will be deducted from your Pay-Per-Minute time for every second watched.Premium PPM allows us to bring you the best Adult content from the hottest studios.Scandalous2025 AVN Best International…

2 seconds will be deducted from your Pay-Per-Minute time for every second watched.Premium PPM allows us to bring you the best Adult content from the hottest studios.Cock TherapyThese girls sure…

2 seconds will be deducted from your Pay-Per-Minute time for every second watched.Premium PPM allows us to bring you the best Adult content from the hottest studios.Audition Vol. 19, TheThick…

The Marvels XXX: A Porn ParodyCosplaygrounds fifth original production takes aim at the Marvel Cinematic Universe with The Marvels XXX: A Porn Parody (2024)! Blake Blossom steps into spandex to…

All the screaming 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, get the BEST…