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….
Lezley Zen’s noticed the smell of another woman on her husband’s clothes, and discovered the business card for an erotic masseuse in the pocket of his suit. To find out…
The prissy blonde bosses the pool boy around as if he’s beneath her, demanding fresh towels and oil rubbed all over her flawless body and lady bits. He holds his…
Dr. Olivia O’lovely calls her friend Sergio, asking him to save the life of one of her patients who is in a very critical condition. She knows Sergio hates needles….
Jana Cova is “Porcelain.” This intimate and artful production shines new light on Digital Playground’s exclusive contract super star, Jana Cova. In this glamorous and smart vignette, director Celeste effortlessly…
Freddy is in dire need of cleaning services so he hires a maid to clean his house. However Freddy has an interesting fettish, He likes to watch women clean his…
Lucas Frost is playing some innocent Bocce ball with his friends, but the game is interrupted when sexy MILF Savanna Samson passes through the field. Lucas leaves his friends behind…
Marina (Mia Malkova) tiene una cita con un instructor de Yoga que su amiga Linda le ha recomendado, llamado Arnold (Erik Everhard), y que le ha cambiado la vida. Marina…
Harley King wants her stepbrother Tyler Cruise to give her a big creampie. Tyler has been resisting her charms, so Harley decides to try something different. She grabs finger cuffs…
Roommates Learn To Share Lacey Jayne saw her BF Jmac staring at her roommate earlier, and she’s still mad! She tells him to get out of her room, and Amari…
Keiran’s never given much thought to his teen tomboy neighbor Alex. Little does he know that her idea of a good time is spying on him as he’s jerking off…
Jack is really busy casting for music videos and he’s scored some super fine ass for volume 38. Digital Playground’s amazing contract super stars Teagan Presley and Lacie Heart join…
Jordan Ash just bought himself a sweet new ride, and the best feature of all is definitely the trunk space. His new car has so much storage back there that…
Ivy Lebelle is stunning in lingerie as she poses sexily in her chaise lounge. The dapper-looking Charles Dera can only stand by and watch for so long before he oils…
Jordi has banged every type of woman there is in the world. Teens, MILFs, cougars, kittens… But let me pitch you this scenario. Jordi is playing the role of a…
Aviana Violet always wanted more than just a work relationship with her co-worker Jay. Now that he’s leaving the company for a better job, now is the only chance she’s…
In ancient times, intrepid adventurers would travel many miles for even the most fleeting glimpse of a gorgeous natural rack like the one belonging to the lovely Layla London. Luckily…
Lena is putting in the hours, studying late at night at the library. All that hard work has gotten her exhausted, so who can blame her for nodding off for…
Payton Preslee’s massive tits don’t need an introduction, and neither do her pierced nipples and clit ring. She likes to play dress up too, so here this super sexy cowgirl…
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…
