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 his camera….
Double Dick for Discount Realtor Danny D finds himself in an odd situation when sexy Ema Karter and her hubby Jordi come to check out a house he’s selling. Ema…
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, YOU will get…
Cam star Kayley Gunner has the best fans and she returns the love in her latest unboxing vid by testing out all the sex toys and lingerie they gifted her….
Shot entirely on HD, Shay: Sexual Freak 3 features Digital Playground’s newest contract star, the lovely Shay Jordan, in a plethora of deviant and mischievous erotic play. Sexual Freak 3…
A man plays with this beautiful little 18+ teen Asian hottie. First he pinches her nipples and and plays with her beautiful tits. Then he spreads her twat and demands…
Mike is an international playboy based in Paris who is in “the pleasure business” and makes his living by providing his business associates with stunning escorts and playmates during their…
The sexy Hime Marie wants to get her living room cleaned up, while lazy boyfriend Kyle Mason tries to watch TV. Watching Hime repeatedly bend over in her tights gets…
Sarah Vandella walks in and finds Maci Winslett naked and making out with her new husband, MILF Sarah says “let me show you how to do this!” Joining in on…
Sex goddess Jasmine Jae just married the love of her life, but during their honeymoon she wants to assure him that she’s not going to get fat or become a…
Lola Fae is a fun-sized petite cutie that is ready to be dicked down by a big black cock in her tight little asshole. She prefers a dick sized between…
I was spying on my stepsister Patricia Acevedo while she was modeling her outfits for a TikTok. She caught me filming her naked, she got angry and scolded me, but…
Shot entirely on HD, Jack’s Teen America 21 features Digital Playground’s lovely contract star, Lacie Heart in a slam-min’ romp with Scott Nails, Poppy Morgan & Renae Cruz in decadent…
Keiran and Romi have just moved to suburbia and are ready for a quiet, normal life. A few days after moving in they throw a halloween party so they can…
Morgan is getting all settled into her new dorm room with the help of her Mom’s boyfriend, Danny. Morgan takes the opportunity to get to know Danny a little better,…
Ariella Ferrera has been married to her new husband for a couple of months. During that time, her stepson, Jordi, has become obsessed with her and her superb cleavage. When…
Natty’s boyfriend Charlie hasn’t fucked her in a year, but there’s another dick in the house that she just might like even better! Charlie’s brother Jordi seems to spend all…
Petite blonde Baby Kxtten craves rough, hardcore sex. The deviant cutie meets hung studs Brian Ragnastone, Deny Lou, Mark Dozer, Michael Fly and Thomas Lee for an epic anal gangbang….
Today Kira and Missy are celebrating their stepdads birthday! What better gift to give than a blowjob? Mom is out of the house, so he wants to get naughty. He…
Jack’s at it again! But this time, it’s professional… and even kinkier than before. Jack turns what he knows best into a career. Welcome to Jack’s answer to getting a…
That’s an understatement! Inked beauty Tigerlilly makes her HussiePass debut this week, and we paired her up with our good friend Damion Dayski for this week’s tattooed interracial MILF update!…
Bonnie Rotten and her squeaky-clean husband check into a hotel for a romantic getaway, but they have no idea what’s in store for them! When the hotel receptionist, Quinton James…
