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….

Uploaded: 2024.02.24 2024.02.23 Show more…

Tina Kay is a sex fiend that can’t get enough of her boyfriend’s cock. She gets dressed up in a leather dress to seduce him before they take their time…

Oh lock up. You’d think being behind bars would be a time for repenting but not when you are incarcerated with Briana Banks, Violet Monroe, Lily Cade, Lily Lane and…

The party is hours from now, but I had to come early to take a peek at the sexy Anya Ivy. She’s so hot and wants me to play pool…

This nasty little Asian just can’t get enough dick in this final scene from “Bukkake 10 Nintai X Nakadashi,” in which this tiny little 18 year old set of holes…

Kali is having a wild night in her kitchen – dancing and baking up a storm. She’s got the music jacked and not a care in the world. That is,…

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…

Italian beauty Valentina Nappi oils herself up over and under her bangin’ full bodysuit, spread out on a massage table, ready for Kyle Mason’s warm hands and hard cock to…

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…

Self-isolation is tough for a real nympho like Tina Kay. She misses fucking her boyfriend so much she records a dirty little video for him where she covers her sexy…

Karla doesn’t like darts, but she LOVES dicks. So when her man’s friends come over for a friendly game, she lures them away for some REAL fun.

Bodacious porn star Vanessa Sky wears shiny latex, a black miniskirt and a red top with high-heel boots. The stylish brunette sucks her finger and shakes her shapely hips, pouring…

In Part 2 of Something Borrowed, Something Blue – beautiful and bubbly Aidra Fox arrives at the wedding to be a bridesmaid. Dark-haired Aidra is hopelessly romantic and has no…

Dylan Phoenix has been so bored and horny since coming home for the summer that all she wants to do is stay inside and rub her sweet pussy and play…

Jay Snake has a big exam, and the more he tries to remember what he studied, the more he panics, and the less he can actually remember! His teacher takes…

Eva Generosi is sitting by the pool waiting for professor Tony Rubino, who is going to help prepare her for the English exam. He brings up some questions to her…

Kira Noir and Paige Owens, both alone and horny, decide to reconnect via a video chat. Things start innocently enough, but after Kira wins a high stakes online game, she…

Xander and Aaliyah are trying out a little something special for Xander’s birthday. Aaliyah brought over some rope from a sex shop, and she lets Xander tie her up for…

Blonde bombshell Olivia Austin blows bubbles by the pool while showing off her ample assets before getting a good, hard fucking from Jay Smooth.

Krissy Lynn’s son has had some trouble making friends, but he seems to have connected with Ricky Spanish, who has come over to hang out and is staying for dinner….

Sit back and grab your cock as you watch this horny Asian hottie get her hairy pussy worked by a man with toys in tow. He gets her dripping wet…

Van is interviewing Alena to see if she would make a good stepmom. Even though she wants his permission to marry his dad, but the interview has to go both…

After a busy night at a fancy restaurant, the wait staff wants to loosen up before heading out for the night… until they get busted by their foul-tempered Head Chef,…

Like a gem, Nichole Saphir’s alluring beauty glows in her skimpy top, skater skirt, and bedazzled heels. Starting with a sensual strip tease, the tattooed blonde enticingly undresses, revealing her…

Harley Dean is a gorgeous, tattooed black nineteen year old that we hope to see more of! She loves to fuck and she’s all about showing it off on camera….

From the makers of 2007’s Best Release “Babysitters”, 2008’s Best Seller & Best Release “Cheerleaders”, and 2009’s 1 hit “Nurses”, comes the bigger, sexier “Teachers”! Textbooks, homework, detention, lube, dildos…another…

Nikki Nicole takes a peep at her stepbrother showering and notices his big dick. She walks in the bathroom and boldly takes off her clothes and tell him to make…