India is getting ready for the honeymoon of a lifetime. She’s left Jessy and Kimberly in charge to house sit so everything goes smoothly as she’s away. They have some…

Daya Knight is just enjoying her afternoon jog when Danny D starts following her. After seeing those big tits bouncing he can’t help himself. Lucky for him Daya loves a…

After a series of home invasions, Ani and Martin team up to take the night shift for the Neighborhood Watch they organized.

When Luna Star is trying to complain to her sister-in-law, Gabriella Paltrova, about her husband, Gabriella is far more interested in checking out her phone and listening to music on…

Angel is outside by the pool enjoying her day topless. When Parker sneaks into the backyard to get a good look. Carelessly he forgets rule number one of creeping and…

Johnny Sins has been in a coma for months, unaware the apocalypse has wiped out every other man on earth. Dr. Peaks, Dr. Rain, Dr. Aniston and Dr. Starr have…

After a fight breaks out in a bar, Robby Echo comes to the bartender Alissa Avni’s defense while his friend captures it all on film. Alissa rewards Robby with some…

Jeni has her eye on the perfect dress for the summer. Unfortunately, so does Lyra. Their argument quickly turns into a tug-of-war of who saw it first. Things escalate quickly…

Jessy is failing his human anatomy class, so his teacher Ms. Breeze decides to help him out. Using her shy stepdaughter Charlotte as a live model, Ms. Breeze teaches Jessy…

Lysagna Del Ray is cute and sexy all at the same time. Her small tits, firm ass, and lovely feet receive compliments from Maestro. The tattooed blonde, wearing a skimpy…

Kimmy’s best friend has already celebrated her bachelorette party last week but, it just wasn’t wild enough for her, so she’s arranged a naughty party with just their close friends….

Danny D and his asshole friends are always giving Kayla Kayden a hard time just because she’s got big tits and gorgeous long legs. But when their boss takes off…

This slutty Asian has a nice handful of tits and a big hairy bush. She’s in the bedroom with two guys at the same time and she spreads her legs…

Mikage Sakata is always getting ready for sex or having it, and this is one of those moments when she’s in the bathroom making sure everything is clean and ready…

Uploaded: 2024.02.20 2024.02.20 Show more…

Johnny Sins is in trouble with his wife and he doesn’t even know why! It’s too bad he can’t read women’s minds… except, when Johnny, wakes up the next morning,…

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: 2024.02.09 2024.02.07 Show more…

I got my camera out just in time for this beauty to wake up from her slumber. She stripped into some booty shorts but once she found out I was…

There’s nothing like a day of catching rays, swimming, and pounding Ella Knox’s wet pussy in the pool! Johnny Sins might just be the luckiest guy in the world right…

In this self-shot sex documentary series from some of the biggest names in the business, Digital Playground gets up close and personal, offering you a behind-the-scenes look at what it’s…

Uploaded: 2024.01.06 2024.01.03 Show more…

Eliza Ibarra and Seth Gamble have decided to skip town for a few days to get a little rest and relaxation. However, these plans are put on hold when Eliza…

Karina King and Renato go to a shoe shop where they meet Barbie Roux, a salesgirl. Attracted by her natural sensuality, Karina longs to see her again. After overcoming her…

It’s Luke’s busiest day of the year, and his boss decides to dump Candi on him for a rundown of the company. Candi has to spend the day at her…

Peter can’t get a job, and he’s feeling pretty down about it, especially since India Summer made it clear that he needs to. For follow-through, India decides to lift his…

It’s the beautiful Devon Lee fellas!! Devon has a beautiful face and awesome big boobs but her best feature has to be her perfect peach shaped ass!!! We knew you’d…

Mechanic Abigail Morris has been getting dirty and working up a sweat when girly-girl Theodora Day comes in to pick up her car. Abigail checks out her panties and her…

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…