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….

Bianca Benett loves Paula Shy, and she wanted to show it with a sensual fuck on their vacation down south. After coming upon Paula relaxing outdoors, Bianca put the moves…

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…

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…

August Skye is on a business trip with her co-worker Ryan. They booked the closest room to their weekend conventiion, but the only room has one bed. See Ryan is…

After a long day, Maddy likes nothing more than to kick back and relax. Especially if it involves gorging down on Isiah’s gargantuan meat stick. All that she asks is…

When Van Wylde’s girlfriend, Kayla Kayden, brings him home to meet her stepmom, Cherie Deville, and her step-grandmother, Van could never have imagined what would be in store for him….

Uploaded: 2024.03.12 2024.03.12 Show more…

Jaclyn’s fiance doesn’t want to pay for her to get a personal trainer before the wedding, so he asks his buddy Keiran to help her out. As Keiran is perfecting…

Hey Big-Dick, Can Ya Make me SCREAM!? Ophelia Purr has an exciting challenge for Charles Dera: She wants to get fucked. Moreover, she wants to get fucked so hard it…