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…

When Giselle gets called into Dean Mountain’s office for breaking her college’s dress code, she can’t quite wrap her head around why – her skirt is a full inch longer…

New waitress Wendy (Lily Bell) gets an up-close look at the bright lights and the dark underside of the casino when her boss sends her to wait on VIP Jack…

Digital Playground presents DP Star: Season 2, hosted by last year’s DP Star winner and contract girl, Eva Lovia and judged by industry legend Nikki Benz, renowned producer/photographer Holly Randall…

My First Porn is a comical sex-spectacle of Jack directing his first porn movie. In Volume 3, watch Teagan Presley doing what she does best. Add Austin Kincaid and Faith…

MILF Angelica Heart is trying for some tranquility and flexibility with her home yoga workout, but the calm is shattered by the noise of her stepson Jordi El Nino Polla…

After a long day, Isis loves to unwind by either hitting the sauna or taking it in the ass. Today she’s in luck, because Johnny and his thick cock are…

The Retreat It’s just a few days. You can live without your phone for a little while… It’ll be good for us. Just think of this as a little reset….

Alex Chance was always complaining that she couldn’t find a cock big enough to satisfy her desires. One quick trip to Courtney Cummz’ sex shop, and Alex arrives home with…

It’s the day of Kelsi Monroe and her fiance’s intimate, at-home private wedding, and there’s only one thing standing in the way of their blessed union: Kelsi can’t take her…

While strolling by the sea, Agatha Vega encounters the charming Kristof Cale. Determined to take a chance, she invites Kristof to get better acquainted in a hotel room. An offer…

With a meteor set to strike and destroy earth in a mere 12 hours, lecherous married couple Violet (Karma Rx) and Aaron (Xander Corvus) and their more conservative counterparts Ruth…

When Nickey’s husband gifts her an at-home session with Danny, a self-proclaimed “professional bed yogi”, she’s instantly suspicious of him. After spending the entire session interrogating him, Nickey finally starts…

Kristof was lying on the sofa when Anissa walked up to the sliding glass doors and started teasing him, pressing her large breasts against the window so he could look,…

Spicy Selena is absolutely irresistible. Watch as she and her lover bask in love’s embrace.

When Shay Sights learns that her daughter is getting bullied by the neighborhood jerk she decides to take matters into her own hands and pay the bully a visit! Shay…

Kendra doesn’t want to play Amber’s game, but she can’t help wanting to settle the score, both online, and with Amber’s IRL boyfriend. Part 2. Uploaded: 2024.02.12 2024.02.08 Show more…

Natalia’s a pin-up goddess and Charles is a greaser—and both are straight out of your 1950s wet dream. Natalia is closing up at the diner when an attractive customer comes…

Jessy Jones’ new stepmother is always on his ass bout chores, but when he walks in on this busty blonde MILF masturbating, he gets a crazy idea! Rubbing her tight…

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…

Uploaded: 2024.03.16 2024 Show more…

Finishing her quick jog, Ania Kinski prepares to invite Michael Fly. After taking a soapy bath, the raven-haired MILF wears a black body-hugging latex dress and lingerie that draw attention…

Diamond Foxxx has injured her ankle and can barely walk. Dr. Ryder gives her a full physical, including a pussy exam, then massages her pretty feet. Diamond gets so turned…