Sexy mature Asian brunette is brought into a room by one man who plays with her hairy cunt and fingers her from behind. While her head is down, another man…

You’ve loved Hannah in everything and now you can enjoy her work as you never have before, with all the production values Digital Playground is famous for. Hannah Harper is…

Kennedy Kressler is an outgoing blondie who isn’t afraid to flash her tiny titties in a public park. They stop to get a caricature drawn and her pussy is exposed…

Uploaded: 2024.02.06 2024.02.06 Show more…

Antontio was asked if he wanted to work with Caitlin or Mira. He just smiled and raised one eyebrow. Fair enough Antonio… you want to slam both of their faces…

When Jackson breaks up with his significantly younger girlfriend Kennedy, she’s furious – what could this older woman possibly have that she doesn’t?! After looking into Laura on social media,…

Boob lovers can’t go wrong with the delightful Abigail Mac. She has two stunning tits and she knows how to use them. In this scene, Abigail tries different bras under…

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 Digital…

Nobody enjoys a proper buttfucking more than the lovely Savana Styles. Today Savana will be getting railed by the enormous appendage of one Daniel D, himself a master in the…

“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 original contract star, Rocki Roads in brand…

Trixie thought having less dark studs on her at the same time would make things easier… truth is it just gives them more room to use while they work her…

Ava Addams tiene un hijastro muy caliente, Jessy Jones, que no atiende sus reglas. Ella ha tratado de todo para disciplinarlo pero nada parecer resultar efectivo. Harta de sus travesuras,…

Jack is really busy casting for music videos and he’s scored some super fine ass for volume 38. Digital Playground’s amazing contract super stars Teagan Presley and Lacie Heart join…

Uploaded: 2024.02.15 2024.02.15 Show more…

Uploaded: 2024.01.07 2024.01.01 Show more…

Keiran Lee is a funeral director, and while he was at work one day, his ex, busty Asian Milf Akira Lane, decided to swing by and get a piece of…

Keiran Lee’s younger girlfriend is having a pool party at his house, and she’s used his credit card to pay for it! Keiran’s upset, to say the least, however the…

Aria Valencia is a petite teen that has some rock hard nipples! She has a gorgeous crop top on and the whole time we can see how horny she is….

Ayaka Minami wanted to take a nap, but her lover had better ideas. He offers her his rock hard cock, right before she lays down, and Ayaka dutifully takes it…

I Can Make This All Go Away A high school teacher, Ms. Branford (Sarah Arabic), is in trouble because word got out about her affair with an 18-year-old female student….

Blonde bombshell Rachael Cavalli just finished her lingerie shopping, and she is horny as fuck, when she arrives at her boyfriend’s house, the one answering the door is Tyler, her…

Good friends, Ava Lauren and Sienna West, were just relaxing and talking at Ava’s house. Sienna then couldn’t help but noticed the pool boy, CJ. Well, since their husbands haven’t…

Introducing Julia De Luica and her juicy, cock-craving ass! She shows off her round butt in tight white yoga pants before letting Tony bury his hard cock deep inside her…

Coco De Mal is a thick beauty who loves to get her pussy and ass stuffed with cock! She craves cock night and day and one just isn’t enough! Her…

Sofia Lee and her big natural tits get a massage from Charlie Dean and his skilled hands. Sofia’s in heaven, moaning more and more with every touch. When every inch…

Japanese women are raised to be submissive to the sexual requests of men. But not every J-girl can deepthroat on demand. It’s a unique skill to be able to swallow…

Cali Carter is a hot babe that is feeling horny with all this time spent home alone. She brings out all her fun toys and preps her pussy for her…

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….