Jill (Gigi Allens) is the finest, most diligent secretary that Brad has ever had. Even when she’s not at her desk, she’s underneath his, working long hours to get her…

Van went the extra mile to do well in his college urban planning course – not only did he spend hours working on his latest project, he invested in a…

Maddy May’s vacation was far from over, but that didn’t give her any joy. Tired of everyday routine, she longed for something to captivate her. So, when her stepbrother asks…

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…

Alex Coal is into her stepbrother, Nathan Bronson, but she doesn’t want to be too easy to get. She decides to send some mixed messages to mess with Nathan before…

Bill Bailey is watching his sexy stepsister Kylie sunbathe by the pool. She looks so good, but he could never fuck her – that would be wrong. Kylie’s dad asks…

MYLF.com – Nicole Doshi – “Learn a Woman’s Touch” Stepmom’s Stamina Training

Roxxxie Blakhart’s classic car is in the shop and she wants to drive it one last time with her family. She owes a couple hundred to get the car out…

When the guys in Mr. Sins’s Sex Ed class weren’t grasping the basics of anatomy, Mr. Sins brought in another teacher Ms. Bentley to help him out. Considering Ms. Bentley…

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…

Alex can’t take it anymore. Anytime he tries to get somewhere with his girlfriend, she shuts him down. Fortunately, Alyssa overhears their plight and would hate for her daughter to…

Mischievous MILF Liza’s new star gazing hobby is a lot less innocent than it seems. While most astronomers set their sights on the sky, Liza has her telescope aimed at…

After Anya and Gina discuss their boring sex lives, they decide that what they both need is to swap boyfriends, and film it to see how each other’s guys actually…