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’s a sexy lifeguard like Korina Kova supposed to do when her beach is completely empty? Korina oils herself up, then takes the opportunity to get herself off by the…

Bubbly blonde Addie Andrews teases the camera in her sexy string bikini before stripping down and sliding into the pool. She skinny dips and shows off her hot bod for…

Jack is really busy casting for music videos and now he’s landed Digital Playground’s super fine contract star, Sophia Santi alongside Selina Draagen, Alyssa Chase, Carli Banks, Marlena, Christina Brooks…

Myra Moans is trying to make a vid for her social media to talk about her favorite makeup products. Her stepbrother, Jimmy Michaels, keeps getting in the video frame. Myra…

Who wouldn’t want to get wet with the gorgeous Penny Pax? The smoking hot redhead drenches herself in oil, teases through bubbles and gets her ass and pussy pounded while…

Busty tanned MILF Candi Kane has underestimated just how much work goes into gardening, but her friend’s son Jordi is old enough to help out! After accidentally spilling water all…

The virgin Seth Gamble is caught having sex with an apple pie and gets his chance to experience a real woman when Tasha Reign comes over. Moments later she realizes…

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…

Jasmine is a nymphomaniac, and she can’t hold down a job because she spends too much time having sex and getting fired for fucking in the workplace. Nick’s a business…

Tina Kay is hired as a sales consultant to help fire up a failing sales team. Danny D quickly learns that Tina’s methods are anything but conventional! Sex sells, as…

Niki Snow has been waiting for this moment for years. Its finally her chance to prove how well she can be a BANG girl. Her costar lifts her skirt of…

Cherie Deville is an unconventional sex therapist who meets her daughter’s boyfriend, Kyle Mason, for the first time. Cherie’s daughter is embarrassed by how open her hippie mother is when…

Business negotiations with such a strong-willed, beautiful woman like Simon Kitty requires your personal attendance… and all your vigilance and stamina. Having to fly over to your sister company has…

Kali is trying to cool off on a hot day and her step brother, Sean, is ready to help. Sean suggests a game where he blindfolds Kali, feeds her a…

When Molly (Jane Wilde) takes on her friend Alice’s repeating day burden, she thinks that it will all be hustling mobsters and robbing banks. Though she’s not wrong, what Molly…

What Jade wants, Jade gets. When her boss was too busy on a call with suppliers to pay her any mind, Jade decided to hijack his attention by any means…

Heather (Skye Blue) thought she got everything she wanted: Maxine’s man, her money, and her jet! All that’s left is to slip into a flight attendant uniform to taunt the…

Keira Croft is a gorgeous exotic beauty that loves to show off her perky tits and curvy body. She plays with her nipples and gets her pussy extra wet before…

A shady enterprise known only as The Company, run by a mysterious Employer (Ivy Lebelle), is in the business of training assassins-for-hire. When Mason Reinhart’s (Scott Nails) target (Aidra Fox)…

Meeting guys in hotel rooms for group sex isn’t something this beautiful long haired brunette Asian girl does often, but she really loves the feeling of six hands on her…

Parker has been bullying professor Alexis Malone’s son so she confronts him on it, asking him to stop. But just like a bully would think, he wants something in return….

Liv Revamped is stripper at heart and begins working the pole like you wouldn’t believe, but all she wants to do is to get rammed. Luckily, we gave her a…

Luna is a horny maniac who loves to go into stores and make a mess— by masturbating in the aisles, that is! While the shopkeeper is helping a customer, he…

In the heightened sensual state Keisha’s in today, just pulling her panties down the crack of her ass and between her legs sends a shiver of delight up her spine….

Sexy brunettes Maddy May and Kuleana are both present at the illustrious annual Blanket Bastion event (hosted by the Pillow King, Michael Vegas). The goal of the event is to…

The stern new warden at the ZZ Prison has a special disdain for notorious inmate AJ Applegate, who he’s locked in solitary confinement with Markus Dupree as her personal guard….

Josephine Jackson gets out of bed and heads to the bathroom, stripping out of her PJs and freshening up in the tub when her roommate’s boyfriend, Angelo Godshack, accidentally walks…

Jessy visits the doctor for a physical. The only catch? The doctor is his stepmom, and she is horny as hell.

Ava Sinclaire is a voluptuous seductress who overflows with appeal, Maestro can’t fight being magnetized by her beauty. Looking fabulous in her blue and rhinestone covered bikini, this fuckable babe…