Krissy Lynn is a hot as shit stripper who gets a visit from nerdy boyfriend Danny D and his mean girlfriend. Danny D’s girlfriend is attempting to give him the…

Sitting in her CEO office, Sasha Rose is expecting a very important package. But when it arrives, she might have to sign off on the delivery guy too! After all,…

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…

Xander Corvus bust in through his girl Teanna’s bedroom window and buried his face right in that juicy ass. Teanna tried to focus on her homework, but there was no…

Alexis Fawx is pampering herself today. First, we see her outside in a cute bikini, enjoying the sun and getting herself all wet. When she goes inside, she’s greeted by…

Olivia spends most of her days bored and horny at home, dreaming of her next hard fuck. So when a hot, young stud moves in next door, she wastes no…

When college dean Jasmine catches frat guy Jordi initiating a pledge on campus, she is absolutely furious – she will not tolerate this kind of behavior at her school! While…

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…

Kimberly Kendall is a student at the ZZ Private Academy for Slutty Schoolgirls, and she’s got a huge crush on her teacher Danny D. She heard from another student that…

Has it been days? Months? Years!? Xander Corvus asks himself how long he’s been walking in this vast desert instead of dwelling on his impending doom. The blazing heat finally…

Anissa Kate is the baddest bitch in the neighborhood and Bambino has come crawling to beg her to let him join her harem. Unfortunately, it’s pretty obvious that he’s not…

Bridgette B works from home, which allows her to be the perfect stay-at-home mom to her adult son. Little does he know that she’s not really a “consultant,” and her…

When Darla Crane gets home and sees her stepson Logan Pierce filming a home made sex tape with his new girlfriend Alice Green, she’s not mad. In fact, as a…

Whitney Wright is a magnetic, dark haired beauty, and she rightly wants to immortalize her good looks by hiring a photographer to snap some juicy photos of her wearing nothing…

It’s a beautiful day for browsing in a charming china shop, but of all the lovely items in the store, Annie finds herself most interested in the handsome owner. Distracted…

Mila is an Asian girl with the tightest pussy around, so her college friends aren’t letting her get out of class without taking all their cocks! First they squeeze her…

Trying out all the new sex dolls available is exciting enough, but when you get to do it with your sexy sales rep? That’s even hotter! Courtney Cummz sucks and…

Jesse Jane receives a text and sneaks out of bed and from her sleeping husband. She greets her late night client, Keiran Lee, at the front door. Keiran wants to…

Nolina Nyx’s daily jogs have not only caught the attention of Will Pounder, but of a disgruntled neighborhood wife too, who doesn’t appreciate how Nolina flaunts her hot body for…

It’s a steamy day in the carpentry workshop for Nikki when his wife Zazie shows up in a flirty outfit, feeling pretty hot herself! Zazie teases her husband by perching…

It’s that dreaded time of year when the annual employee survey comes back. Boss Monique is less than satisfied with the results, especially the trust and team satisfaction portion. So…

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…

After a desperately dramatic attempt at stealing Martins car, street girl Nikky fucks him and gets the ride she really wanted.

Personal trainer Quinton James challenges his smoking hot client Alexis Fawx to do a series of squats onto a suction cup dildo, then rewards her hard work with a well-deserved…

Valentina Nappi is the best accountant there is, but her best client Isiah Maxwell is spending all his money on big booty strippers. She can’t lose him as a client,…

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….

Baby Got Boobs Vol. 20 Ashley is a wild cowgirl working the mechanical bull, but she’d rather take Robby for a ride. There’s nothing quite like getting bucked and fucked….

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…

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…

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…