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…
When she started cleaning up Mr. Maxwell’s lavish home, AJ Applegate never imagined the heat he was packing. But that all changed the day she walked into the bathroom and…
Alyssa Branch has spent the afternoon prepping her hairy pussy for the extreme stretch she’s going to get from her boyfriend by playing with a dildo. When he gets home,…
Hot blonde Candee Licious is enjoying the big outdoors while riding on a quad bike when it breaks down and leaves her stranded. She soon catches the attention of David…
In the cover of darkness, Alyssia Kent’s fingers explore every inch of her fit body, craving a man to satisfy. Like a wish from a magic lamp, Danny D and…
Alexis Fawx is having a lounging yacht day and she’s in no mood for shrimp or champagne. She wants full service and she’s not referring to the bottle kind, she…
Ella Knox looks hot as fuck in her short shorts and thigh high tube socks. Her big tits hang down allowing you to appreciate their natural weight. Ella is high…
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…
Eva Maxim is at the local laundromat, bending over to put her clothes into one of the washing machines. As she does so, another customer, Hailey Rose, can’t help but…
Texas Patti just joined her son’s baseball team and his best friend is very willing to teach her how to hit some balls. But the only balls this busty MILF…
Meet the sensational Jasamine Banks, who gets wet and a little kinky in the bath before she slips in and out of her sexy red lingerie. Jasamine shows off her…
Wax in, Wax Out Kayley has a thing for Adonis, the window washer. Her husband Mick has no idea that she is trying to get some action from this virtual…
Sarah Vandella is in rare form in this XXX hardcore clip. Sure she has her pussy fucked hard and deep but that hardly competes with the fact that she fists…
Brooke Haven and Rachel RoXXX are interviewing for a new position at the office. At first, they found that Barry Lamstein would be best for the job, until Billy Glide…
Platinum blonde, baby blues and butterfly spangled porcelain skin, Hayden is your classic BVHB (Babes Very Hot Babe) and a lady who really gets off, on people watching her get…
Jack’s Playground 33, features Digital Playground’s one and only insatiable and sexy Devon. She’s eager to make the music video cut and demonstrates her distinct talents on Scott Nails’ throbbing…
Legendary pervert Kisaku isn’t gonna let a little thing like his own death get in the way of getting a piece of ass. When his ghost is brought back by…
Daiki Akiba had no idea that what started out as a totally normal schoolday would end with him in the middle of an orgy, getting to fuck his crush, Ami!…
Alexis Tae is missing her man Small Hands, who had to leave for a business trip. But just because Small Hands is out of town, doesn’t mean he stops doing…
When Heather (Demi Sutra) and Sam (Scarlit Scandal) discover their best friend Vanessa (Demi Sutra) is getting married to a guy they absolutely can’t stand (Xander Corvus), they set out…
