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…
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…
With the end of Brazzers Hours upon us, your hosts Keiran Lee and Nikki Benz decide to pull out all the stops, with a crazy group fuck fest, complete with…
Olivia is a flat chested bookworm who gets bullied by all the hot girls, resulting in the Kleenex she used to stuff her bra, falling out! Luckily, the school Dean…
Markus’s new coworker Raven is a babe, but everything she does makes him look bad. Her work’s always perfect and the boss loves her. However, when the prim and proper…
Yuri Aine and Yuu Sakuraare dick suckers that are always ready to suck another load out. Looking pretty is a big part of doing their best job as a cocksucker,…
Eligible bachelor Charlie Dean has two sexy suitors, brunette babe Anie Darling and blue-eyed beauty Alexis Crystal, but only one rose left to give. What’s a man to do when…
Nympho Nurses & Dirty Doctors 3 When Xander agreed to partiticipate in a paid memory test with his wife, he had no idea he’d wind up being locked away in…
Jordan’s husband’s friend Marcus has been kicked out of his house and needs a place to stay. He invites Marcus for a few days until his situation gets better. This…
Jack’s Playground 32, features Digital Playground’s contract babe, Sophia Santi, eager to make it in the music video scene. She shows her distinct talents and raw, exquisite beauty in two…
With Aaliyah Love’s regular physician retiring, she got her the choice of two new "doctors". But it’s just naive Aaliyah’s luck that her new practitioners care more about ogling and…
Jane Wilde and Juan El Caballo Loco are two out of control humpers looking for someone new to play with! When they’re taken to the park and let loose, the…
Takaki Hijiriryo just got out of the nail salon, and she’s finally all ready for her big night at the hotel with her new male friend. She’s excited to meet…
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…
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….
Master Robby D. delivers more hot pussy pounding and intense orgasmic blow jobs. This time he turns his attention to some sexy ass mothers we’d all like to fuck. Some…
Musician Luke is composing his next song when beautiful blonde Cecilia arrives for her first piano lesson. Luke seats her on the bench with the proper posture: back straight, chest…
Whitney Wright is trying to get her college roommate, Johnny SIns, to fuck her but he doesn’t want any part of it since he has a girlfriend. She’s frustrated by…
Sensual Foxy Roxy Hart is looking hot in a skimpy bikini, showing off all her curves. That’s okay because this horny redhead can’t keep her clothes on. It’s not long…
Kendra Sunderland is the complete package. She’s got brains, she’s got beauty, and she’s got sarcasm drier than Mars. But nothing in this world is perfect… She’s a clutz. She…
We were driving around trying to find something to do when we ran into Chelsea Rae on her bike. She was having some problems, her chain was jamming, my man…
