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….
Scarlett Mae answers the door to the census investigator looking to inspect her vagina. She lets him in and shows him her perfect pussy before allowing him to inspect it…
Kylie Page is your typical bad babysitter, putting the little one to bed early so she can get herself off. Unfortunately she is interrupted when his father Keiran comes home…
Kendall shows up to her friend’s house, but her friend isn’t there yet! Who opens the door? Her friend’s hot dad. Does he mind if she waits? Not at all….
Instructor Duncan Saint must teach his boss’ teen Alina Belle how to drive, but driving isn’t the lesson the curvaceous babe is interested in. Will her dick-riding skills prove better…
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…
Chloe Couture is an adorable blonde, who’s often mistaken for being under-age. Tired of having to prove she’s a woman, Chloe has decided to show the world by agreeing to…
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…
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