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….

Keiran was dreading having to do yet another interview for the data entry position in his office. And guess who walked in? His ex Jaclyn Taylor, wearing a low-cut top…

Nina’s had a thing for her best friend’s hot dad for a long time, and she’s picked the perfect day to make her move. The cute teen knocks on his…

Meme Lovers unite! Meme Lover 2: Dawn Of Just is here, jam packed with all the hottest, wettest, sexiest memes you can shake a stick at. PLUS Cara St Germain…

Bill Bailey is a businessman who prides himself on punctuality and professionalism. So when a client invites him over for dinner and then doesn’t show up, leaving him to make…

Cute little Asians are known for following all the rules, but this one is extra fun to play with! Watch her present her hairy pusy with her extra long pointy…

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…

Kai Taylor wanted to show his girlfriend Nekane his favorite action-horror movie, but the fraidy-cat fox was less than enthusiastic. Jumping into his lap during an especially thrilling scene, Nekane…

Ryan Conner can’t stop starring at her friend, Ariella Ferrera’s, new stepdaughter. She’s got the cutest, little ass she could just bite! Jenna Sativa hates her stepmom’s rules, but her…