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…

When Jessie Volt’s pen leaked in her pocket and stained her blouse, it was very nearly a dress code disaster! Convinced she had enough time to whip off her shirt…

A guy pretends to be gay to get close to Maryam Hot and then fuck her.

Katt is a new member of an exclusive tennis club, and she wants a massage after practice. Once Jessy gets a look at her jiggling in that little uniform, he…

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…

Jack is really busy casting for music videos and now he’s on the hunt for big, beautiful boobies. They bounce, and they shake. There’s more than a mouthful, more than…

Jordi is trying to impress his girlfriend with his sexual prowess. However, an overly eager Jordi is only able to produce a single, sad bubble of cum, prompting his girlfriend…

The My First Porn series is a comical sex-spectacle of Jack directing his first porn movie. Volume 8 is 3 full hours and features Digital Playground contract stars Sophia Santi…

Colombian doctor Ashley Sanz got horny seeing a well-hung patient. She fucked him immediately.