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….
A sexy divorcee yearns for love, but is looking in all the wrong places. Her ex has already moved in between the legs of a much younger busty blonde, and…
Gina and her boyfriend Dean are enjoying a casual date night when it occurs to Gina that maybe things between them have gotten a bit stale. When she brings her…
Amanda is on the web surfing and having fun. She stumbles upon a webcam chat room and picks up a video chat with Justin. After a good visual teasing, she…
Billy walked into his friend’s house hoping to get his text book back, and found a stripper pole right in the middle of the living room. Luckily his friend’s mom,…
Maya Bijou loves a challenge, especially when her costar uses her shirt in ways she could only imagine. Taking his cock from the top and behind she doesn’t quit until…
Charles returns home from a long day of work and in need of some alone time. He’s shocked to discover Hadley sitting on his couch. He’s never met her before…
Sexy babe Scarlit Scandal is completely unable to sleep at night. After trying to fight it for a while, spending nights tossing and turning in her bed, Scarlit chose to…
Ryan Keely has invited her college friend Katie Morgan over to visit. While Ryan currently has her own boyfriend (Alex Legend), she still has eyes for Katie as well, and…
This John has always had a thing for bringing strong women to their knees. When he meets sexy tranny hooker Foxxy, he knows he’s met his match! She spends lots…
Lady Dee spent a quiet afternoon in her hotel room while her lover was at a business conference. She took out her massive dildo to occupy her time but decided…
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…
Lisey dotes on her girlfriend Osa, serving her breakfast in bed. Osa enjoys being fed strawberries, but she has a taste for something sweeter. The only thing better than a…
Jack is really busy casting for music videos and now he’s on the hunt for big, beautiful boobies. They bounce, and they shake. There’s more than a mouthful, more than…
Alex can’t take it anymore. Anytime he tries to get somewhere with his girlfriend, she shuts him down. Fortunately, Alyssa overhears their plight and would hate for her daughter to…
Keiran is shocked when he walks into his kitchen one morning and finds his son’s girlfriend Lana cooking breakfast in her panties. Lana wanted to surprise her boyfriend with breakfast,…
Danny D is a little obsessive when it comes to his cleaning. So much so, in fact, that when he finds a couple crumbs on his spotless counter, he decides…
Let’s get real – you may be texting an invitation for her to come over and watch a movie, but what you’re really thinking is "please bring that precious punani…
Sexy and horny Jada Kai is on a phone call with her boyfriend (Jackie Knight), who’s been out of town. She teases him by telling him about the lingerie she…
You’ve loved Hannah in everything and now you can enjoy her work as you never have before, with all the production values Digital Playground is famous for. Hannah Harper is…
Spring break is finally here for Professor Danielle Renae. She’s got one last task of grading and then she’s off. She’s also feeling so horny after class with nobody around…
