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….
This horny Asian hottie has never trimmed her massive bush. She lets it grow wherever it goes and she spreads her legs to let a man finger her hole and…
Ricky Johnson lives a pretty boring existence. He flips burgers by day and watches TV at night. He has no idea a one night stand is about to change his…
Jay Smooth is roommates with sexy little minx Mackenzie Moss. When she sneaks into her room one afternoon for some well-deserved “self-care”, little does Jay know that Mackenzie is actually…
Carolina Sweets is a petite brunette with just a little paunch beneath her pierced belly button and firm titties. She plays shy, but keep in mind, Carolina came to us…
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…
Little ladies want to prove they can suck cock too! These petite blonde cuties drop to their knees and bury the bone in their pierced mouths. It takes two of…
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…
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