Queenie Sateen enters the living room and sees her parent’s girlfriend, Eva Maxim, who is looking after Queenie while her parent is away on a business trip. Eva is reading…
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….
Ryan has her contractor, Keiran, come over to install a sex swing as a surprise for her girlfriend, but when Keiran sees Ryan’s kinky "playroom" he gets other ideas. Keiran…
Jodie Taylor’s boyfriend has been begging to do it in the butt. So while she’s soaking in the bathtub, getting ready for their next sexy encounter, she decides that they’re…
Aften Opal’s boyfriend, Small Hands, is getting ready for his old college roommate to arrive. He’s making everything perfect for her and it’s pretty suspicious. When it turns out his…
“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…
Olive Glass looks stunning in her bra and panties, slowly peeling them off while she teases the camera and her pussy. Once Olive is down to her black stockings, she…
While most prefer to stay inside when it’s raining, Karma Rx truly embraces getting soaked. In fact, when it rains, she feels compelled to strip and shake her tits and…
Maggie (Romi Rain) and Roger (Danny Mountain) are a sex-crazed married couple… but there is more to their marriage than what meets the eye. After a fulfilling day of separate…
Katya Rodriguez is a badass brunette teen who has no time for her new stepdad, Keiran Lee. So, after Katya slips into some fishnets and sexy gothy boots, she attempts…
Tiffany Tatum is the hot and horny new secretary of Jay Snakes. A big tease, the young temptress comes to work in a short black skirt and thigh-high stockings, giving…
Been watching a lot Penelope Woods videos. Have also been a fan of her cam shows. I’m lucky enough that, after some back and forth, she agreed to meet me…
Jack’s Playground 34 features Digital Playground’s exotic contract superstar, Katsumi. She’s a panty hose model by trade but she’s eager to make the switch to music video queen. She demonstrates…
Cheyne came into Dr. Milano’s office for a routine flu shot. Now Cheyne really doesn’t like needles so Dr. Milano had to put him at ease. We all know the…
Myra Moans has a sexy new outfit that she can’t wait to show her long distance boyfriend. Between the sexy little top and the miniskirt, it’s clear she’s not wearing…
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…
