She’s new to the whole waitress thing, so her boss has her complete some training in the backroom. While wearing her cute little uniform, Jessie gets down on her knees…
Keiran just moved next door to a wholesome couple, Monique and her husband. As he’s unpacking, he pops over to their place to borrow a hammer, and that’s when he…
August is happily married, but her husband’s loser brother is always hitting them up for money. Today he walks in on her in the shower, but before she can kick…
Morgan is getting all settled into her new dorm room with the help of her Mom’s boyfriend, Danny. Morgan takes the opportunity to get to know Danny a little better,…
Hoping to see her lover Dr. Peaks, Rachel Starr is a bit disappointed when male doctor Johnny Sins arrives to examine her. When the male doctor realizes that nothing’s wrong…
It’s Darcie Dolce’s day to relax, so she’s paying a visit to nuru masseuse Ayumi Anime. After Darcie strips down she gets comfortable on the mattress and lets Ayumi go…
Bailey Brooke is a stunning blonde with a big ass to boot. She requested to be fucked in her own home, and had a “Cribs” style walkthrough with Sean Lawless…
Erik Everhard can’t believe that his accountant Wilford is married to such a smoking hot babe. Luckily for Erik, Aria Alexander’s husband totally takes her for granted, leaving the door…
Katana Kombat’s wedding is coming up quickly and she’s freaking out. Luckily, her maid of honor has arranged for a special massage to help her deal with her wedding day…
Weed Princess called someone over to fix her sink. The plumber was one hour late, so once he got there she was already irritated. She demanded to get a discount…
Rachel Rivers is having car trouble and she needs to drive 4 hours to get back home. It’s late at night and she doesn’t have anywhere to stay until the…
Even in the middle of a gold rush, there’s more than one way to strike it rich. Mysterious newcomer Maria (Kimmy Granger) goes looking for Sade Freeman (Adria Rae) at…
Alexa Johnson is adrift in the seas of her own inflamed desires. She’s wet and eager for a partner, but her man is away on business. This afternoon, she’s just…
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….
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…
Kimmy goes kawaii and shows off her sexy body in a skimpy outfit. She strips nude and begs her man to fill her with cum. Uploaded: 2024.02.13 2024.02.13 Show more…
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…
Tyler is sick of his neighbor September disrupting the neighborhood. He shows up at her place to tell her to keep it down, but instead is treated to a sneak…
Haley Spades is an insatiable slut so she requested to get DP’ed by two other girls. Yes, Bella Blu and Demi Morgan got strapped with dildos and went ass to…
Jay’s birthday is coming up, and Sydney is doing everything at hand to be the coolest stepmom about it. She wants to throw a big party for him and she…
