Michael goes to the pharmacy in hopes of finding something to help him please his girlfriend with, but the hot MILF behind the counter shows him that he doesn’t need…

Alex Chance and Tori Avano wanted to make the best of what’s left of the summer, and nothing says fun in the sun like some outdoor anal sex! The two…

Uploaded: 2024.02.09 2024 Show more…

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…

Security guard Jmac is having a snack in the cafeteria when nerdy college student Willow Rider greets him with a flirty hey. She treats him to a look at her…

Two rascally plumbers got Letzy Lizz really horny and fucked her.

Starring Digital Playground’s newest sensation, Shay Jordan and an entire cast of young, gorgeous, almond eyed beauties, Jack’s Asian Adventure will please your pallet. Jack uses the tried and true…

Skyla’s boyfriend is so obsessed with sports he sometimes forgets to give her proper attention. So when his buddy pulls a muscle during the big game Skyla is ready to…

Alexis Tae is missing her man Small Hands, who had to leave for a business trip. But just because Small Hands is out of town, doesn’t mean he stops doing…

Young and horny freshman, Mindy, and the Professor have already had their naughty affair but this time he’s requested her to spy on their rival university, and discover their secret…

Everybody fucks, herself including, but former super-heroine turned private eye Jessica Bones (Alex Harper) is in the business of exposing the sex that people shouldn’t be having. When a wealthy…

Julian also did his part in correcting these porn star wannabes. Erica wouldn’t really hold still at first so Julian took it upon himself to grab her by the feet…

Haley Hill wants to go swinging with husband Charlie Dean, but not in the way you might think. Looking to spice things up in the bedroom, the Serbian babe didn’t…

“Jack’s Playground 31,” the superstar edition, stars the lovely Jana Cova in two delectable scenes, Devon in all her naked splendor and DP’s original contract star, Rocki Roads in brand…

Dr. Star is surprised when Johnny walks into her office this morning. She has been treating him since he was a kid and apparently hasn’t treated him in awhile because…

Marica Chanelle’s big, beautiful breasts are just made to get shown off – and that’s exactly what this super babe is going to do! She gets into a shower, letting…

Uploaded: 2024.03.10 2024.03.08 Show more…

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….

Hopeless romantic Leny Ewin wanted to surprise his fiancee Violette Pink with a sexy surprise, sprinkling rose petals on her bed and covering her eyes with a blindfold. Little did…

My First Porn is a comical sex-spectacle of Jack directing his first porn movie

Delivery driver Selina Bentz sees packages all day long, but when she makes a drop off at Don Diggler’s house, even she’s impressed by the size of his package. When…

The sexy Cherie DeVille and Jenna Foxx have gone without sex for too long and something’s gotta give! The girls catch up with each other via video chat and their…

The holiday season is upon us, and it’s making me so horny! Ok, I’m horny all the time, but that doesn’t mean the season isn’t doing anything to me. Thankfully,…

Jenna Fireworks is a petite blonde with fake titties and a soft spoken voice. However, for her Pretty & Raw scene she wanted to get nailed by two well hung…

Today I picked up dark-haired stud Alex Sen in the Fake Taxi, and just one look at him got my pussy juices flowing! During the ride, Alex told me he…

Dee is taking a luxurious steam in her sauna when she’s rudely interrupted by her son and his friend Sean. Her son is a bit of a prude but that…