Jimmy Michaels stumbles upon a workout video tape featuring the one and only Luna Star. Jimmy can’t keep his eyes off the bombshell as she stretches out her perfect body,…
When stepmom Alexis Fawx has had enough of being treated like a maid by her lazy new stepson Jimmy Michaels, she decides to show him her other side, going through…
Detective Ariella Ferrera may be a loose cannon but she gets results. Unfortunately for her, Captain Sean Michaels has had it up to here with Ariella’s insubordination and reckless policing….
Sean wants to be cured of his pussy eating addiction. Dr. Riley Reid, his psychiatrist, decides that the only way to cure him is to show him that getting could…
Happy Saint Patrick’s Day! Today we celebrate with comely lass AJ Applegate as she offers her own "pot of gold" to Irishman Sean Michaels. Top of the morning!
Mr. Gunn is usually a patient teacher but if there’s one thing that really sticks in his craw, it’s an ignorant slut like Jean Michaels disrupting his lectures on Shakespearean…
Holly Michaels is one of the hottest nurses to ever step inside a hospital. All of her patients can’t help themselves but want to get a piece of her fine…
After ‘The Disappearance’, Cali has so many questions. Why was she chosen to be left behind, and where have the rest of the world’s women gone? One thing she realizes…
Katie Morgan is a hot blonde with a body that won’t quit. Her new stepdaughter is not the nicest to her boyfriend, Jimmy Michaels. Jimmy wants to get busy and…
Some people say you can fuck your grief away, and that’s exactly what queen cougar Sally D’Angelo does at her husband’s funeral. Yes, she’s sad. Yes, she cries. But with…
Osa Lovely has a peculiar seduction strategy when it comes to Jimmy Michaels, who just happens to be dating Osa’s boyfriend’s daughter. After she bakes a majestic laptop made completely…
Casca Akashova is a big breasted blonde babe with a real desire for cleanliness. She’s a clean freak! She even irons her towels. When she walks in on Jimmy Michaels…
Horny MILF Cory Chase has some movers coming over today and she’s eager for them to handle more than her boxes. When a pair of movers arrive, including Jimmy Michaels,…
Charlotte Rayn is enjoying a movie night with her new husband when her new stepson, Jimmy Michaels, tries to butt in and watch alongside them. Jimmy’s dad would rather he…
The highlight of London Rose’s day is when young stud Jimmy Michaels sneaks past her clueless husband to give her the sexual satisfaction she craves. However, on this particular morning,…
Jimmy Michaels is supposed to be training under the watchful eye of his stern football coach, Coach Peepers (Jay Slayher)… but he’s a little distracted right now. Jimmy’s cute girlfriend…
While Jimmy Michaels is stuck cleaning up the mess his roommate (Bailey Base) left in the kitchen, Bailey’s being lazy. Bailey’s feeling horny, however, and masturbates until she decides to…
Sexy home care nurse Lacey London has her hands full with an aging patient, but what makes matters more complicated is the rivalry between stepsiblings Tori Montana and Jimmy Michaels…
Michelle Anderson has a laugh when she catches Jimmy Michaels humping a pillow, and she pulls out her phone to record the oddly intriguing sight. Not long after, however, curiosity…
Valentina Nappi gets her ass oiled up stretched out by Sean Michaels’ big cock during an unconventional yoga session. A good hard fucking in the ass will leave Valentina feeling…
Shot entirely on HD, Jack’s Teen America 18 parodies beauty pageants and Jack’s lovely contestants all compete for the crown. They take off their clothes, they masturbate, they suck, they…
Don’t miss Digital Playground’s Exclusive Contract Star, Stoya in her debut boy / girl scene. Jack’s POV 9 is off the hook sex! All the screamin’ hot sex in Digital…
Shot entirely on HD, Jack’s Teen America 19 features Jesse Jane and Sophia Santi in intimate and seductive hardcore action! The Jack’s Teen America series arodies beauty pageants and Jack’s…
Jack is really busy casting for music videos and now he’s landed Digital Playground’s super fine contract star, Jesse Jane®. She fucks Ben English every which way in true gonzo…
The “My First Porn” series is a comical sex-spectacle of Jack directing his first porn movie. Volume 6 features the amazing anal queen, Delilah Strong in a butt scene with…
The “My First Porn” series is a comical sex-spectacle of Jack directing his first porn movie. Volume 6 features the amazing anal queen, Delilah Strong in a butt scene with…
The “My First Porn” series is a comical sex-spectacle of Jack directing his first porn movie. Volume 6 features the amazing anal queen, Delilah Strong in a butt scene with…
The “My First Porn” series is a comical sex-spectacle of Jack directing his first porn movie. Volume 6 features the amazing anal queen, Delilah Strong in a butt scene with…
The “My First Porn” series is a comical sex-spectacle of Jack directing his first porn movie. Volume 6 features the amazing anal queen, Delilah Strong in a butt scene with…
Jack is really busy casting for music videos and now he’s on the hunt for big, beautiful butts. They bounce, they roll and they shake and Robby finds pleasure deep…
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…
Jack is really busy casting for music videos and now he’s on the hunt for big, beautiful boobies. They bounce, and they shake. In volume 3 of this delicious show,…
The “My First Porn” series is a comical sex-spectacle of Jack directing his first porn movie. Volume 7 features the lovely and sweet Gianna in a tempestuous fuck scene with…
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 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….
