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…
Gianna Dior has no room in her busy schedule for a massage, but she’s in desperate need of a rubdown, so she’s going to need to multi-task. Stirling Cooper isn’t…
On Madoka’s first day back as a member of the Student Disciplinary Committee, she keeps interrupting a mysterious gray-haired guy as he hooks up with girls all over the school….
Unlucky at work and love, Gary Murphy gains the ability to read people’s minds. In the process of realizing that office politics need a little cleaning up, he discovers the…
All the screamin’ hot sex in Digital Playground’s award winning Jack’s Playground series are now shot in POV perspective for your ultimate enjoyment. In Jack’s POV Playground, YOU will get…
Getting a new tattoo always puts Karmen Karma in the mood for more deep skin penetration! She hit the local adult bookstore before heading home, and now she rewards herself…
Leyla Peachbloom has such a delicious, perky ass, it’s no wonder her man wants to get deep inside of it. As a special treat, Leyla’s decided to experiment with ass…
Mia Malkova just flew in to visit her friend, but she’s stuck at work, so her brother Johnny picked Mia up from airport. His sister is gonna be a while…
Rising star, Xander Corvus and his buddies’ are living it up in Hollywood! His acting career is booming and he’s taking his friends along for the ride. Having caught the…
Remy LaCroix gave her brother and her best friend a trip for their engagement, but her friend’s Ex-boyfriend sent her some dick pics. Remy’s brother saw them so Remy stepped…
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 losing his job due to quarantine Duncan Saint moves back with his parents and younger sister Melody Foxx. Melody hasn’t seen Duncan in years and she’s stoked to have…
Kristen Scott loves posing for the camera and looking pretty, but the only experience she has is some modeling she did for a fashion show at the mall back in…
The sexy Cherry Kiss is just about ready for her massage with Sam Bourne, but after taking her top off and exposing her tits, she climbs onto the table with…
What blonde could resist some hot chocolate while she’s curled up on the couch? Certainly not Jenna Ivory, whose big tits are like the marshmallows melting on top while she’s…
Two sexy Latinas Missy Martinez and Contract Star Selena Roseâ„¢ are getting a tennis lesson until they realize they’re both horny and would rather play with actual balls than the…
Kira is a bit of big spender (when it comes to spending her husband’s hard earned money). When the bills come in, he decides that they have to sell the…
Olivia, a strip club cocktail waitress turned dancer, gets entangled with her married, mob-affiliated boss, Sal, after breaking up with her boyfriend. When Sal’s wife, Gia, spies the two of…
It’s rare for Dr. Piper’s students to visit him at home, but he made an exception for his top student Kacey Lane. While showing him her notes, Kacey caught a…
