Jack is really busy casting for music videos and now he’s on the hunt for big, beautiful boobies. They bounce, and they shake. There’s more than a mouthful, more than…

Hot blonde and new MILF Angel Allwood isn’t quite ready to have vaginal sex again after giving birth. But she’s horny as hell, and knows her man needs some action,…

Melissa Milano named herself after a Pepperidge Farm cookie. She is firm on the outside and loves having chocolate shoved inside her. Too bad for her no black dick was…

Vanessa and her stepdaughter Jane arrive at the Airbnb for their fun vacation and meet Vince, their handsome host. He charged them a pretty penny for the room and he…

Violet’s blind date Keiran is a total dud. Not only is he rude, obnoxious and cheap, he also had the audacity to spoil the ending of her favorite TV show’s…

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With five lovely ladies competing for the same title, which girl will take the honors? Will Brooke or Jamie get to deliver their acceptance speech? Did Jack vote for one…

This 18 year old little slut gets her ass felt by her girlfriend in this fun scene from “Beach Volley 9.” These horny friends start to spice things up when…

Nathaly Cherie would never try and explain her love of the bad boys. She just goes with what she likes, in this case, studs like Angelo who flood her pussy…

When you’re a horny slut like Alby Rydes, sometimes you just need to get your ass fucked. So Alby called up Bill Bailey, who she knows loves a woman in…

FUCK ME YEAH, now this is what a brotha calls ass. This is some fucking huge white ghetto booty. I fell in love with this monster ass the second I…

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…

Xander is trying out an "all natural" wellness clinic which specializes in holistic, full-body healing. At first he rolls his eyes at the hippie techniques, but he’s not complaining when…

Shay: All-American Girl is a heartwarming and sexy tribute to youth growing up in America. Scott presents Shay with a lovely birthday cake, only to have his cock dipped in…

Aiden Ashley, Charlotte Sartre and Small Hands turn back the clock in this stylish retro-inspired scene… and they will turn heads when things heat up and the two beauties treat…

Scarlett Rose is a wild one. We pulled up on her taking a break from her family vacation. She was looking for a little action and excitement, so we offered…

Ichijo Manami is into rubbing her pussy before she gets fucked, because it really gets her in the mood. These two studs have big dicks that make their way into…

The biggest faux pas for a doctor is misdiagnosing a patient because the results can be detrimental. Dr. Mikayla told her patient he had an STD. When the distraught patient…

Jess (Kira Noir) and Max (Ricky Johnson) are a young, boring couple who have never experienced great sex. They visit a therapist in hopes of fixing their sex life. Linda…

It’s summertime and backyard BBQs are here. Peter is at his friend’s house preparing the coals and the meat to get things going while his friend’s daughter, Leana Lovings, is…

The Official Egypt can never get in the bathroom when she needs to, because her roommate Evelin Stone is always bogarting it! Egypt decides to teach her selfish roomie a…

On the surface, Alena seems like a happy mother and wife. But below that surface is a cock-hungry milf who won’t let anything get between her and a good fuck….

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….

Just when Shimazu, a new teacher and sex trainer at a prestigious private school for girls, thinks that he’s finally got his three pretty students, Yumiko, Tomo, and Asuna, trained…

Giselle is close to getting kicked out of her college class once again for her disruptive behaviour. She continues to take naughty pictures of herself in class while her professor,…

Jack is really busy casting for music videos and now he’s landed Digital Playground’s super fine contract star, Teagan Presley. She takes a big cock in the butt and we…

It seems like Mikey Butders has just stopped caring about school because he knows that he’s about to receive a football scholarship. However his teacher, Mrs. West, is angry with…

Aleska Diamond has had her eyes on her personal trainer Jay Snake for quite some time now. So when she catches him checking out her sweet ass while she’s working…

Alexis Brill was relaxing at home, changing out of her clothes and getting ready to meet her boyfriend for a Halloween party, when she heard a strange noise in her…