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….
Clea Gaultier is stretching doing yoga when Freddy comes over to join. He notices really quickly that she has a hole in her pants. She tells him to take it…
Two couples go camping in the woods. One couple is carefree and up-for-anything while the other is uptight and has a schedule to keep. It seems like they wouldn’t get…
Five horny teens. 2 sound guys with equipment. 1 contest. 1 winner. Sound familiar? It is. It’s Jack’s Teen America.” Put it in and cast your vote! Jack’s at it…
Violet has no idea how she’s going to go without cock for thirty whole days while she’s under house arrest! As muscular Officer Pierce locks a tracking device around her…
Danny D is ready to embark on his backcountry excursion in the ZZ National Park, but first he must heed the warnings of a stern Park Ranger, who cautious him…
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…
Jasmine Grey sneaks backstage and just wants to meet the band, but her attempt to hide from stage crew member Scott Nails doesn’t go as planned when he finds her…
On a dare, Kylie Nicole breaks into neighborhood tough guy Jordan Ash’s house. But when Jordan comes home and busts her hiding in his pantry, he gives her the fucking…
What better way to spend Mother’s Day than to be spoiled rotten by your hot stepson Tyler Nixon and his cute girlfriend Lana Sharapova? Sexy MILF Sarah Vandella knows this…
Lela Star is getting pretty impatient as she’s waiting for her masseur to show up. He was supposed to be at her place hours ago and now this highly important…
Ri-Ai Saotome is a horny slutty Japanese newbie with big round tits and an extra hairy cunt. She wants to make a good impression with her first time on camera…
There’s a gorgeous damsel in distress on the side of the road. Her car is broken and she can’t get ahold of her boyfriend. A stranger is there to give…
Keiran is having the worst time trying to get some shut eye at the hospital. It makes things even harder when Nurse Jane comes around. It’s bad enough that he…
Daisy and Kinzi seem to know exactly what they are looking for in a new roommate. He has to be clean, respectful, know how to party and especially know how…
Elena Lux wants to go for a relaxing massage, but once her masseur gets her hands on her body she wanted more. Slowly seducing him, she turns around to get…
From the visionary Writer/Director Joone, come the long awaited and highly anticipated sequel to Digital Playground’s “Pirates”. Superstar Jesse Jane® returns as the irresistible Jules – the seductive pirate hunter…
The kids have left for college, and Alison is struggling with empty nest syndrome. What can a gorgeous woman do to satisfy that empty feeling? After a failed couple’s therapy…
Reality Kings stars Ricky Johnson and Morgan Lee are at the beach asking the beautiful people some questions, most importantly: “Smash or pass?” Not only do big-titty babe Alyx Star…
