Busty student Josephine Jackson gets bored waiting for office hours to start, so she takes a few selfies and even some upskirt pics outside her hot prof’s office. When Professor…
Music can truly awaken the soul, as this beautiful Queen (August Skye) discovers. It leads her to the one man (Seth Gamble) her body desires more than anything. Her only…
Jennifer White is a world famous pornstar that needs no introduction. She’s done it all throughout her career and in this scene we have her eating out Elaina Raye’s pussy….
When a patient came in complaining about her husband’s big cock breaking her vagina, Dr. Jessa Rhodes had to see for herself what all the fuss was about. Telling him…
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….
Blake Blossom is the latest guest on Johnny Love’s podcast. As she sits down to get interviewed, she can’t seem to focus. Instead all her attention is going to Johnny’s…
Power mogul Brooke Peterson (Jessica Drake) is hot, sexy and one very domineering bitch but her husband, Charles (Cheyne Collins) has had enough! After discovering a hidden world of paradise…
Taisa Banx never knew that her husband harbored bi-sexual tendencies until she talked him into a two man threesome. While it started out with the guys just taking care of…
Tan, long-haired, glamorous blonde Bree Brooks wears clear heels with a skimpy bikini, teasing as she shines up her athletic body. The frisky vixen douses herself in hot oil to…
Hiding Her Bikini When Jordi El Nino Polla gets home to find his hot stepmom Octokuro sunbathing naked by the pool, he sneaks up and steals her cast-off bikini, running…
Jack’s casting again! This time he’s looking for leg models… sexy, leggy vixens who want to be in fresh, up and coming music videos. In the second volume, Digital Playground’s…
Lynn Vega is sick of having her stepson’s girlfriend sneaking out of her house at all hours of the night. It’s the last straw getting woken up by Anya Ivy,…
Welcome to The Sessions, a sexy series that allows you into one of the most intimate spaces known to man—the therapist’s office. Be a fly on the wall as patients…
Not all girls like random sex toys shoved up their pussies, but this horny Asian with a hairy pussy loves the clear dildo and long blue device belonging to this…
This Asian couple really knows how to get down and dirty! One minute, they’re looking at a manual together, the next minute, he’s playing with her hairy Asian cunt. She’s…
Japanese female athletes tend to need more deep pelvic stretches, especially before spending the day running on the field. This particular girl also needs to practice her maneuverability in a…
New waitress Wendy (Lily Bell) gets an up-close look at the bright lights and the dark underside of the casino when her boss sends her to wait on VIP Jack…
She’s the fastest runner on the track team, and when she catches her pervy coach spying on her in the locker room, she proves to him that she’s number one…
Shot entirely on HD, Jack’s Teen America 20 features Digital Playground contract stars, Shay Jordan, Sophia Santi and Jana Cova with industry babes Hillary Scott, Holly Morgan and Sue Diamond….
Upon returning to school, Ai Mizushima is confronted by two men who want to give her a deeper appreciation of sharing her tight teen body with at least two raging…
After a photo shoot with Stevie Shae and Annika Albrite, feelings start developing. Stevie has a boyfriend, but she’s strongly attracted to Annika, a feeling she can’t shake. The ladies…
Nicolette has just helped Keiran buy a house. Ever since they met there’s been sexual tension, despite his wedding ring. Once their business is out of the way this sexy…
“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…
While she’s waiting for Coach Venture in his office, Angel Windell phones her friend up. She explains her problem to her friend: She isn’t satisfying her boyfriend in bed, so…
Cleaning is the last thing on cute blonde teen Giselle’s mind as she exchanges passionate kisses with her boyfriend Jessy, until her stepmother Ariella reminds her that she has chores…
