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…
Dana is showing Elizabeth around campus, but when they walk past nemesis Amanda at her “Women Power” booth, Dana and Amanda come to blows, and Liz gets mixed into the…
Charles is on a mission. He’s got a tip that a certain massage parlour might be offering sexual services on the side. Naturally, this gumshoe is ready to play hardball…
It’s a hot day and sexy neighbor, Nicole Aria, wants a sun tan. She’s checking herself out with her phone and starts to get horny. Nicole starts masturbating, rubbing that…
Tasha Reign is in the Doctor’s office, hoping he can help her with her chronic cock deprivation. She tells the nurse on duty that she can’t stand the feel of…
Lucas Frost is playing some innocent Bocce ball with his friends, but the game is interrupted when sexy MILF Savanna Samson passes through the field. Lucas leaves his friends behind…
Divorce was supposed to solve their problems. But when Katie and her ex-husband Keiran hit the dating scene they realize: more family, more problems! In this extended family game of…
Big titted Kaitlyn came over for a breast exam, she tried doing it herself but did not fully understand the procedure. Doctor Jordan showed her his technique and took her…
Lonely milf housewife Parker loves the peen so much, she spends her mornings scouring date sites hunting for it. With a neglectful rich hubby at work all day, this babe…
“Deeper 3” is beautiful, erotic and cinematic homage to the greatest horror movies ever made. Starring Digital Playground’s contract superstar, Jesse Jane® in 2 twisted and mind-blowing fuck scenes, Deeper…
Allie Haze had a workout scheduled with her yoga instructor Chris, but as she bounced on her workout ball with all her tight yoga gear on, she was too damn…
Stunning Alyssia Kent and Gerson Denny get soaked from the rain and have to take shelter inside. Amazing Alyssia’s white tank top gets sheer from the rain, Gerson can’t take…
Jack’s Playground 33, features Digital Playground’s one and only insatiable and sexy Devon. She’s eager to make the music video cut and demonstrates her distinct talents on Scott Nails’ throbbing…
In this self-shot sex documentary series from some of the biggest names in the business, Digital Playground gets up close and personal, offering you a behind-the-scenes look at what it’s…
Jewelz Blu is unsatisfied with her boyfriend’s dick. She wishes he had a bigger cock. Flustered by this, he decides to go into the garage and concocted a potion to…
Amy White had a extra sexy afternoon planned for her man Matt Ice. Coming back home with a bag full of naughty surprises, she blindfolded him, and using strawberries, feathers,…
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 and true…
Xander is feeling a bit nervous. He’s been waiting in line hoping to get a glimpse of Monique, who just happens to be signing autographs at the convention. When he…
Nina is out for a little trip on her long board when she skates past Security Guard Sins. Johnny is sick of skateboarders on company property, and decides to make…
Sweet babysitter Nicole is jumpy, so when she starts hearing noises when she’s babysitting alone, she calls Kyle to come home right away. Kyle arrives to find Nicole cowering by…
Kourtney Kai has an affection for making you extra hard with interesting noises and soft-spoken whispers. She talks about the dirty things that she wants you to do with her…
Jessie Rogers is a curly haired vixen that’s ready to get her holes filled. After a bit of a striptease in her red see-through lingerie, she was ready to work…
A group of horny friends lie and cheat as they explore outside the boundaries of their relationships for stimulation, only to discover that what they are seeking may have been…
When Jordan Ash comes home and finds his car all dented up, he asks his girlfriend Tiffany Doll about it. For the second time this year, she’s gotten into a…
