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….

Jana Cova is “Porcelain.” This intimate and artful production shines new light on Digital Playground’s exclusive contract super star, Jana Cova. In this glamorous and smart vignette, director Celeste effortlessly…

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…

From the makers of 2007’s Best Release “Babysitters”, 2008’s Best Seller & Best Release “Cheerleaders”, and 2009’s 1 hit “Nurses”, comes the bigger, sexier “Teachers”! Textbooks, homework, detention, lube, dildos…another…

Jack is really busy casting for music videos and now he’s landed Digital Playground’s super fine contract star, Teagan Presley. She takes a big cock in the butt and we…

We have the amateur couple Whipped Creamy on and they show they will fuck anywhere, including the great outdoors. She starts stripping, gets his dick hard, and makes sure to…

This Asian hottie with tiny tits and a hairy pussy is ready to get fucked hard. She doesn’t waste a minute sucking her man’s dick and gets it nice and…