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….
The sexy Aria Banks has gone through a lot of effort to make a big breakfast for her oblivious boyfriend, and she’s pissed when he refuses to eat anything before…
While Cassidy and Jessy were in the shower fucking, they noticed Jessy’s new stepmother running around cleaning. Did she catch them in the act or no? The answer was clear…
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…
Bobbi Dylan has a major crush on her person trainer, but up ’til now, he hasn’t picked up on the cues. So Bobbi decides that instead of working on her…
One of the boyz finally got home from the big house and this party gets started right quickly. A few bills sent down to the corner bring back some white…
Bonnie Rotten is a mad scientist who has set out to find the perfect sexual partner. So far, she’s had no luck, and every single subject she’s brought back to…
Britney and Sadie are a sexy lesbian couple who are discovering that they’re both open to being with a man. Together, they create a profile on a dating app and…
In an epic battle-of-the-sexes, therapist Phoenix Marie takes on her most macho client’s homophobia. She’s wearing a strap-on as big as his dick! It all starts out with him thinking…
Cherie has cooked dinner for her stepdaughter Jojo and Jojo’s boyfriend Justin, but the teen is not impressed by her stepmom’s cooking. Not only does Jojo complain about the meal,…
On a hot summer’s day, Kassandra Raine’s favorite way to beat the heat is by rubbing oil all over her beautiful natural body. With her skin glistening and her pretty…
Babysitting a rockstar is more work than it seems. Keeping a grown man in line, and on time, is almost a thankless job. But this Tranny has it made! Her…
The stern new warden at the ZZ Prison has a special disdain for notorious inmate AJ Applegate, who he’s locked in solitary confinement with Markus Dupree as her personal guard….
Holly’s ready to make her very first house call. She tells Kyle what she wants to do with his big cock as she waits for the bus, scandalizing a nearby…
Danny D is hosting a game night, but the only reason busty sluts Shawna Lenee and Brooklyn Chase even showed up is because they heard he has a huge cock!…
Jack’s at it again! But this time, it’s professional… and even kinkier than before. Jack turns what he knows best into a career. Welcome to Jack’s answer to getting a…
Ayaka Minami is the most generous squirter in all of Japan. She can swamp a mattress just thinking about sex! As Ayaka fingers herself to climax, the pool of wet…
Cute Colombian Latina Melania loves wearing pink, it matches her tight pussy that she spreads for Sam. He explores her holes with his tongue before getting his rock hard shaft…
Charles is hustling in the airport lobby trying to drum up some massage business. When he sees Alix walk by, he offers her the special airline employee discount to reel…
Savannah Stern was decided to make the cheerleading squad. She knew her teacher Mr. Collins could convince the cheerleading coach to let her be on the team. He didn’t seem…
Jordi El Nino Polla and his buddy are playing video games in the common room at their college when they receive a flirty greeting from pretty redhead Lilly Mays. The…
Bambi Black and her stepbrother are such good caretakers. They help their temporarily blind stepdad into the house gently and carefully, sitting him down on the couch and offering him…
Girls Night Freeuse For All Anna Claire Clouds and Lily Lou are having a chill girls’ night in hopes of helping Anna get over a recent breakup. Anna is still…
