Curvy brunette Tru Kait is the perfect caregiver. She’ll tell you exactly how much hydration you need while her perky tits poke through her knit sweater top, hiding nothing. She’ll…
Lily has hired handsome private chef Mike to cater her party. When she checks on him in the kitchen before the guests arrive, the food isn’t the only thing that…
Jillian is pissed off because her Dad got her a gift certificate to a budget massage place instead of her regular Norwegian spa. She’s trying to make do with the…
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…
Dr. Kinski has a couple suspicions about her patient Danny when he walks through the door. He was supposed to be totally healed months ago, yet he’s shown up to…
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…
Jack is really busy casting for music videos and now he’s on the hunt for big, beautiful butts. They bounce, they roll and they shake and Jack finds pleasure deep…
Courtney is a wealthy MILF who enjoys all the finer luxuries in life. When Van the Milk Man brings her weekly delivery, she invites him upstairs for what seems as…
Demi Sutra and Quinton James are just roommates and nothing sexual has ever happened between them before but when Demi finds herself hungry for a good pounding after a sexy…
Ellena Woods wants to show you her tight teen body, but not right away. First, she wants to tease you with peeks at the luscious curves of her figure, and…
Alexis Monroe is an absolute dream. Her flowing blonde hair falls just below her ripe fake titties. Her tiny blue bikini is a tease as she strips it on and…
Kara Faux is super excited about getting her first full-body massage, now that she’s old enough to be naked in public! She starts flashing her titties on the way to…
Starring Digital Playground’s newest sensation, Shay Jordan and an entire cast of young, gorgeous, almond eyed beauties, Jack’s Asian Adventure will please your pallet. Jack uses the tried and true…
Lichelle and Richelle were having some fun by the pool when Alec showed up looking for Lichelle’s brother. He said that her brother owed him some money and that he…
With Veronica Rayne set to move in with his father, Keiran Lee comes over to over to help Veronica pack up her things. But when the two discover Veronica’s old…
Kim Bella always wondered why she was still required to work even after the dad came home. But this naughty babysitter soon came to understand. He wanted to bang her…
Fiery Latina Katana Kombat moved to a new continent to find love with reserved Euro stud Jay Smooth, but he hasn’t shown her the passion she hoped for. Jay wants…
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….
What happened when Katrina met Leigh? A whole lot of sucking, slobbering and ice fucking! Watch as these two alternative pussy princesses get to know each other by fucking the…
Mike is an international playboy based in Paris who is in “the pleasure business” and makes his living by providing his business associates with stunning escorts and playmates during their…
Breathtaking beauty Athenea Rose is receiving a sensual massage from inked-up stud Angelo, who drizzles oil all over the raven-haired stunner’s big boobs and gently caresses them. After rubbing Athenea’s…
