Jack’s at it again! In his playground, Jack is busy casting for music videos. The delicious girls will do ANYTHING for stardom! Some suck, some fuck, some masturbate but they…
Lynn Vega is sick of having her stepson’s girlfriend sneaking out of her house at all hours of the night. It’s the last straw getting woken up by Anya Ivy,…
When Ember Snow started seeing her sugar daddy, Brad Newman, she had no idea their encounters would be so satisfying. The petite, Asian teen dresses in black lingerie and a…
Digital Playground presents DP Star: Season 2, hosted by last year’s DP Star winner and contract girl, Eva Lovia and judged by industry legend Nikki Benz, renowned producer/photographer Holly Randall…
All his life, Danny D’s monster cock has been making life complicated for him. Even now on his wedding day, two of his wife’s bridesmaids, Jenni Lee and Scarlet Red,…
Cheyne came into Dr. Milano’s office for a routine flu shot. Now Cheyne really doesn’t like needles so Dr. Milano had to put him at ease. We all know the…
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….
Lola is a Helicopter Parent who just wants the best for her son. Now that he’s in college, it’s even more important to be vigilant with him. When he invites…
Riley has a theory: all male professors are pushovers. This explains her abysmal attendance record and her short attention span in class. Watch Riley put her theory to work and…
Blonde beauty Kendra Sunderland wears the sexiest crop top in this POV interview scene. She smiles and shakes her big boobs for the camera. What a cutie she is when…
All day, Victoria’s been struggling to understand the simple things in her textbook, with some encouragement from her stepmother Uma. It got even harder to focus when her boyfriend showed…
It’s Mother’s Day, and your buddy’s mom Sybil deserves a nice massage to make her feel appreciated. Her own son is nowhere to be found, which makes it pretty easy…
Smoldering hot European brunette Heather Harris needs a place to stay, but the rent her new roommate, Jordi, is demanding, is too high. Heather tries negotiating with Jordi, but her…
Syren De Mer never thought that it would be so hard for her to get pregnant. Unable to hold back her tears, an upset MILF cries, holding a negative pregnancy…
After a long week making her rounds, Dr. Jaclyn Taylor loves a good stiff fuck to help her relax and really forget her troubles. This weekend, she had a date…
Hot MILF Jeanie Marie Sullivan tries to bond with her horny stepson Oliver Flynn by playing video games with him. The game heats up and she can’t resist playing with…
Rhae Woods is enjoying her free time by going to the bathroom and use her brand new dildo. She doesn’t hear Ace Hardz come in and keeps going until Ace…
Alli Rae wasn’t expecting to be asked to babysit Ryan Ryder, after all he’s a grown man who should be able to look after himself! Ryan’s just coming off of…
Long-time girlfriends Cherry Kiss and Haley Hill thought their romance lacked spice, but really, all it needed was extra sugar! Enter busty baker Alexa Tomas with the recipe for romantic…
Fashion designer and model Ivana Vaughn (Emma Hix) will stop at nothing to be queen fashionista, with her latest ultra-provocative fashion line turning heads throughout the industry. Ivana’s archrival, Armand…
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 new POV Playground, YOU will…
August Skye is feeling a bit neglected since her husband’s friend Ryan has been visiting. Ryan is just about to leave back home and gets a surprise, his friend’s wife…
When Lacey London’s dad catches her giving Damon Dice a blowjob in the living room, he kicks Damon out, which really pisses Lacey off. As Lacey chills in her room…
Lola Blond is a gorgeous housewife who makes sure the laundry is ironed when before her husband gets home. Today he surprises her with a hard cock as soon as…
