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….
Jack’s casting again! This time he’s looking for leg models… sexy, leggy vixens who want to be in fresh, up and coming music videos. In volume 3, Digital Playground’s contract…
Sherlock Holmes (Danny D), a clever and renowned London detective, uses his cunning and superior powers of deduction to investigate crimes that the local police department can’t unravel on their…
Jodie Johnson is looking to choose a new stepsister, but first he gets to go through the potential newcomer’s room and see what she’s all about. Anna Claire Clouds has…
Rob’s breasty mom is making it hard to concentrate on studying – especially for Rob’s girlfriend. When Rob has his backed turned, mommy decides to pounce. Someone needs to test…
Diego stops by Melztube’s house looking for his girlfriend. He suspects his girl of cheating on him. Melztube hates to be the bearer of bad news, but she confirms that…
Leya Falcon’s deadbeat boyfriend doesn’t know how to satisfy a woman, so he’s sent her to the masseuse to let a professional get her kinks out! He insists that she…
Suburban stepmom Eva Notty isn’t your typical wholesome housewife. She dreams about being tied up and gagged while a sexy blonde dominatrix plays with her massive mommy tits. Today’s the…
Jack’s Playground 34 features Digital Playground’s exotic contract superstar, Katsumi. She’s a panty hose model by trade but she’s eager to make the switch to music video queen. She demonstrates…
Alessandra cheated on her girlfriend Amber and got caught. What follows is glimpse into what happens when two fiery women (who aren’t ready to let go of each other), let…
Max Fills is looking to choose a new stepsister, but first he gets to go through the potential newcomer’s room and see what she’s all about. Initially Max is surprised…
Don’t miss Digital Playground’s Exclusive Contract Stars, Teagan Presley and Jana Cova in a very personal, off the hook sexual experience! All the screamin’ hot sex in Digital Playground’s award…
There’s nothing AJ Applegate’s husband finds more valuable and important than her big, juicy ass, which is why he’s decided to have it insured. In order to determine the worth…
Jasmine Sherni has an ass of a goddess. With her soft skin shining in the light, you can’t find anything wrong with her body. Our boy Ace stumbles upon her…
Two beautiful passionate girls from opposite walks of life come together in a battle of lust raw emotion egos and unyielding wills to fight it out in a stealthy boxing…
Cherie isn’t sure what’s going to happen at the doctor’s office today, all she knows is she’s supposed to get naked and wait for the doctor. She’s might be nervous,…
Tiffany Watson and Small Hands are in the middle of a friendly prank back-and-forth, but Small Hands ups the ante when he approaches Tiffany from behind, pokes her ass, and…
Leggy blonde model Brianna Moon is in a photoshoot with photographer Jay Smooth when he asks that she take off her clothes. The sassy Penthouse babe requests that he do…
Eliza Ibarra’s weak boyfriend can’t even win her a toy at the carnival, and he’s way too focused on trying to not look like a loser to notice she’s got…
No Time For Fuckery Alexis has a busy schedule, and wished her stepson Brad did too. He chooses to lollygag around instead of getting done like finding a job and…
Posh Kitten plays tribute to the days of pin-ups and high-heeled honeys. The A-list cast pours sexuality across the screen with smoldering glances and steamy seductions resulting in mind blowing,…
Drawing Hard, Creamy Cum-Clusions Seated on an outdoor bench, Brianna Moore is in her own world, drawing/painting and trying to get inspired, so she diddles her pussy to let the…
Rose Banks’ mom had her classic car redone at the shop. The only thing that was not paid for ahead of time was the custom seats. The mechanic needs payment…
This horny Asian chick has nice round tits and thick bush. She gets with two guys and gives them a double blowjob before she opens her legs wide and takes…
