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…

Uploaded: 2024.01.05 2024.01.05 Show more…

Remi Jones has been in the industry for 8 months and she loves to travel and get fucked on camera! She knows exactly how to turn guys on when she…

After a steamy night out, Chad White has brought Lily Rader back to his house for what he hopes will be a hot one night stand. They enter the house…

Zaawaadi is missing her man, so she settles for the next best thing: a nice sensual session riding her vibrator. As she rests after her orgasm, her mischievous roommate Jordi…

Katsuni makes crazy-sex and delivers superb anal scenes throughout Digital Playground’s fourth installment of Video Nasty. She proves her pure and delicious nastiness in a sexually charged three-way and in…

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….

After a hard day’s work, there’s nothing better than coming home to the tender embrace of your lover, and Anita Bellini has been waiting to get home to Sabby all…

Nikki Nutz is in the bathroom washing his hands when he realizes his stepsister Leo Ahsoka has come in the other door. Instead of just leaving, he hides behind the…

Honey Gold is everyones dream. She is a seductive cumslut who loves to gag on dick! She can’t get enough of this big dick as she rolls her eyes as…

Uploaded: 2024.01.06 2024.01.04 Show more…

Sex addict and proud nymphomaniac, Harmony Reigns has arguably the biggest and best tits in porn! She’s also a little British cock-whore who absolutely loves to fuck! So when her…

The “My First Porn” series is a comical sex-spectacle of Jack directing his first porn movie. Volume 7 features the lovely and sweet Gianna in a tempestuous fuck scene with…

Jack is really busy casting for music videos and now he’s on the hunt for big, beautiful boobies. They bounce, and they shake. In volume 2 of this delicious show,…

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…

Is it all in Clover’s head, or is his teacher Ms. Leigh Darby trying to seduce him? Poor guy didn’t have a chance in hell of focusing on the pop…

Daiki Akiba had no idea that what started out as a totally normal schoolday would end with him in the middle of an orgy, getting to fuck his crush, Ami!…

C. StyleX is lounging by her friend’s pool, taking some naughty pics of herself, when her friend’s husband shows up. He arrived just in time too because C. StyleX could…

Poor Joe Blow has had a stomach ache for a while now and it’s not going away. Good thing for him, he’s got Brooke Belle as his doctor, although she…

After his accident, Cheyne had to stay in the hospital to recover. It’s been quite a while now and he can’t stand the fact of not having gotten laid in…

This Asian chick likes to get off with other people watching. She’s on the couch in a communal area when her best girlfriend takes and hold her tits as a…

When three estranged sisters, Kimmy Granger, Ivy Lebelle and Ashley Lane, reunite at their stepmother Nancy’s funeral, they are introduced to Ella Hughes and Danny D, a mysterious duo who…

My Wife’s Birthday It’s Cherie DeVille’s birthday and her wife, Alexis Fawx, has planned out a very special and unique finale to a long day of celebration. She already did…

Kimber and her husband, Mick, have decided to expand their horizons and attend one of Mick’s friends Jason’s legendary swinger parties. Mick seems a bit nervous about wife-swapping, but once…

Digital Playground presents DP Star: Season 2, hosted by last year’s DP Star winner and contract girl, Eva Lovia and judged by industry legend Nikki Benz, renowned producer/photographer Holly Randall…

Alexis Fawx is pampering herself today. First, we see her outside in a cute bikini, enjoying the sun and getting herself all wet. When she goes inside, she’s greeted by…

Restaurant manager Eva Angelina just got caught stealing money from her boss. Now, rather than fire her, her boss is giving her an opportunity to keep her job. Eva had…

Watching flurries of white snow through the hotel window, the forecast seems bleak for Lena Paul and Michael Vegas’ anniversary. But tucked under Lena’s trenchcoat, there’s a naughty surprise that’s…

Avery Jane joins us this week to show us her perfect attributes. This girl is the perfect package, she has a huge hair of tits and a perfectly massive booty….

Cheyne came into the Doctor’s office with quite a problem. It seems he couldn’t get rid of his erection. Dr. Calogera took a good look at it but couldn’t deduct…

Villainous femme fetale Rharri Rhound is in big trouble, and under interrogation from Detective Oliver Flynn. Faced with a folder of evidence showing her rubbing her pink pussy and exposing…