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…
After a hard workout, Rilynn Rae’s personal trainer Keiran Lee could tell she needed to relax. And what better way to unwind after working up a sweat than with a…
Akitoshi’s horny ways just might have come back to bite him this time! Getting his red-haired tsundere stepsister, Hitomi, pregnant was the only way to avoid his fate, but cosplay-loving…
Emily Willis is a bratty, trust fund beauty who is vacationing in a Spanish Villa run by its manager, Danny D. Petite Emily is making Danny’s life a living nightmare…
Dillion has been getting ready for a big night out with Markus. After finding the perfect outfit, Markus tells her that they are going to miss the dinner if they…
Alli Rae wasn’t expecting to be asked to babysit Ryan Ryder, after all he’s a grown man who should be able to look after himself! Ryan’s just coming off of…
Angela Aspen’s husband kept pestering her to set up a threesome, so imagine his surprise when he shows up to find her and another guy waiting for him to have…
Dakota Sky was over at her friend’s place talking about their shared love of dicks when her friend’s brother Keiran Lee came in wearing a tight pair of shorts that…
Scarlett needed a shopping partner, so she convinced Criss to go shopping with her by promising to buy him some jeans. She had no idea Criss had such a huge…
Officer Ava Adams is walking her regular beat when she spots a young couple getting frisky inside their parked automobile. If there’s one thing an cop like Ava hates more…
After finding out his wife Yukie cheated on him with young stud Taketo while he was away on business, Jonathan is resolved to leave for good. Yukie and their stepdaughters…
“Deeper 2” is an intense sexual experience. Shot with all the magic, artistry and design of Digital Playground’s “Erotique” series while still encompassing all of the hot passion and sound…
Don’t mess around with the pretty Lily Larimar. If she has eyes on you, she means it, and she’ll do anything to get your attention. This time, her target is…
Upon discovering that horny teacher Ms. Brooklyn Chase has been having an affair with their fuck-up of a son, concerned parents Alexis Fawx and Tommy Gunn show up to Ms….
After spending a long day at the gun range, Jessa Rhodes just can’t help but feel as hot for her instructor as the desert where the range sits. Offering to…
Rebellious school girl gets caught masturbating with a remote controlled vibrator while in detention. She gets taught a lesson in orgasmic insemination therapy.
Love is an unpredictable thing. You never know when Cupid’s arrow is going to strike, and for Danny D, it struck him the moment he laid eyes on that beautiful…
The “My First Porn” series is a comical sex-spectacle of Jack directing his first porn movie. Volume 5 features the amazing and oh-so-beautiful Jana Cova in two delicious scenes, plus…
Sierra Skye and Cece Stone are best friends who married some bi-sexual boys that were already sexually involved, so their swinging parties are super hot! The girls had to learn…
After receiving an oily massage, the all-natural big breasted babe discovers a hidden camera! She decides to films herself masturbate, but gets caught by the masseuse and they end up…
Porn superstar Lauren Phillips accepts the Her Limit challenge with taskmaster Vince Karter in this exclusive episode. Even Vince is a little star-struck by the voluptuous MILF goddess, but his…
Dalia drinks plenty of man sauce during this clip. She manages to convince her guy to spend a little time fucking her and even gets him to stick his tongue…
Jessy doesn’t want to take part in his stepfather’s stupid Easter egg hunt tradition. That is, until he sees how much his stepsister Tiffany loves to dress up for the…
Sheena Ryder knows all about the art of seduction. This guy is no match for her sexy ways and Sheena was all about riding that growing boner in his jeans!…
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….
Ramu Nagatsuki serves a lot of purposes at the library, but the most important is tending to all the boners she sees peeking out of guys’ pants. Today she walked…
