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…
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…
Busty blonde Shalina Devine sits down in the waiting room of her hairdresser when she meets Yanick, a fellow client. Her hairdresser, Lorenzo calls her through and Yanick gives him…
Dr. Katja Kassin is treating a patient with a rare complication today. His testicles are so swollen he can barely walk!!! Dr. Kassin knows that this situation is the result…
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….
Kenna James slides up and down the stripper pole in her amazing pink lingerie. She shows us all the special moves that she has on the pole, along with her…
Horny nerds Tyler and Ariana can’t wait to get laid. With grad 1 month away, and top colleges on the horizon, they just have to avoid super bitch Jen and…
Ivy Ireland is folding her lingerie laundry and her stepson Rion King comes in to creep on her. He claims he needs help because he sprained his finger last week….
Erica Fontes is traveling the world, surfing couches and sucking cocks. Her latest conquest is Pablo Ferrari, who can hardly believe his luck when he sees the sexy blonde slut…
As the Tokyo requiem continues, a fiery redhead saves her bed-ridden lover by squirting all over his big cock as he fucks her tight wet pussy. Meanwhile, her busty friend…
Nadia Styles is the evening news anchor over at ZZ News, and ever since their first day on air together, her pervy co-anchor Brick Danger has been trying to get…
Jack is really busy casting for music videos and now he’s on the hunt for big, beautiful butts. They bounce, they roll and they shake and Robby finds pleasure deep…
God bless America, the home of many sexy sluts, including the gorgeous goddess, Ava Addams. Her big tits are plump and perfect, but what really makes her hot as fuck…
