Shot entirely on HD, Jack’s Teen America 18 parodies beauty pageants and Jack’s lovely contestants all compete for the crown. They take off their clothes, they masturbate, they suck, they…
The young journeyman is back, bringing his special brand of bondage and domination to horny ladies everywhere. Whether he’s tying up French maids, mounting dildo-riding sluts after-hours at the office,…
Just when Sabina Rouge thinks she’s carved out some alone time to masturbate, her mother barges in and explains that her stepsister, Eliza Ibarra, will be spending the night with…
Bree Daniels has a supermodel body and a gorgeous pixie cut! She has a well-trimmed bush, a perfect set of tits and legs for days! This redhead is a cock…
Karmen Karma’s ass is back! And you know what they say about Karma, what goes around she’ll fuck because she’s down! Watch Karmen shake her moist ass before getting absolutely…
Every woman’s got a secret, and overachieving good girl Scarlett is no exception. As she interviews for a position as Sean’s personal assistant, we viewers get a glimpse of what’s…
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…
Bridgette has planned a getaway to catch up with her old college roomate, Karma RX. Unfortunately, her misbehaving stepson, Ricky, is tagging along. Ricky is a horny little rascal and…
Being the big boss’s daughter has come with all kinds of perks for Casey Cumz. Not only does she make her assistant Bill Bailey do her dry cleaning, and slip…
Big titted Kaitlyn came over for a breast exam, she tried doing it herself but did not fully understand the procedure. Doctor Jordan showed her his technique and took her…
Keiran Lee can’t seem to catch a break. First, his date orders a crazy expensive lobster, then she says no to anal! But his luck is about to turn around…
Digital Playground’s Katsuni was the inspiration for this passionate film. Written and directed by Celeste, Minx is based entirely around Katsuni’s own dominant sexual persona and many fantasies she dreamt…
Teagan Presley & ANAL ” does the rest of this description even matter? Jack is really busy casting big, bouncing, beautiful butts for music videos. They shake, they roll and…
After ruining his lady-love’s lingerie, Van Wylde called a special service specializing in lingerie emergencies. But while trying to order replacements, Van didn’t realize he’d really reached a high-class escort…
Busty blonde Miss Jackson is at the health spa waiting for her next massage appointment. She passes the time by taking a dip in the jacuzzi pool and as 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…
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….
On the first day of their tropical vacation, lesbian lovers Mischa Cross and Tyra Moon were planning on getting lost among the palm trees, turquoise waves, and white sand beaches….
Nicolette and her husband are staying in a hotel while travelling, but her husband is more interested in catching some shut-eye than fucking. Fed up with her solo masturbation efforts,…
Hot, slender brunette doll Angel Windell teases in sheer, white pantyhose and a matching top. She peels off her shirt to flaunt her natural titties. Award-winning director / stud Mick…
With all the pressure of homework, studying and loosing her virginity to her boyfriend, Steve, Bree has decided to eat her lunch in the teacher’s lounge. So, when her favourite…
Kira Perez sits on the couch, watching her stepbrother, Ethan Seeks, talking to his girlfriend on the phone. The call ends and Kira asks if Ethan has ever thought about…
Sexy Japanese model gets covered in warm oil that makes her body glisten and shine. The guys spread apart her pussy and hold her up while they make her cum…
Gina Valentina is dating a hot rebel biker dude that has a nerdy twin bruther. She catches him peering in on her while she’s showering and tells him to get…
What’s playing through Sierra Nevadah’s head as she enjoys a solo adventure on the sofa. Time seems to stand still as she licks her finger and slides it up and…
This pig-tailed athlete has had trouble concentrating on the field. She confesses that it is because she has been daydreaming about boys, and spent all night in a fruitless attempt…
