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….

Eva Lovia is sunbathing in her tiny purple bikini and is a perfect view on the rooftop deck. She gets a boob massage and squirts everywhere when her pussy is…

Jack’s Playground 32, features Digital Playground’s contract babe, Sophia Santi, eager to make it in the music video scene. She shows her distinct talents and raw, exquisite beauty in two…

This pudgy little Asian girl loves having sex, and things get spiced up to her liking when her male friend ties her to the bed with red rope. Next, he…

After receiving a very special package from deliveryman Keiran, Kelsi makes him oil her up so she can slip into her brand new catsuit. Lucky for us, the suit doesn’t…