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…
This Asian hottie is looking for some fun outside in public. She takes off her jeans and shows off her tight pink pussy before she gets on her knees to…
Derrick is a gymnast and he was feeling tight after one of his practices. He decided to stop by Styles Massage Parlor for the famous Butt Massage. The message didnt…
Poor Vanessa. She never could keep her mouth shut. If she hadn’t written down all her friends’ dirty, slutty secrets – maybe, she’d still be alive! But Vanessa’s friends are…
Attempting to make sense of the heights of lewdness he’s seen and experienced in the home of the man he hopes will become his artistic mentor and patron, Xander returns…
Shot entirely on HD, Jack’s Teen America 21 features Digital Playground’s lovely contract star, Lacie Heart in a slam-min’ romp with Scott Nails, Poppy Morgan & Renae Cruz in decadent…
Bobbi and Sophie are The Anal Penetrator’s biggest fans. They love their music so much, they are actually willing to sleep with the band. Knowing the band’s reputation, they are…
Nekane’s boyfriend showed up for Christmas with a surprise that was for her eyes only! But sitting around the living room by the tree, Chad had to wait even longer…
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….
What does it mean to be the perfect maid? According to Nicole Aniston, it’s not only about cleaning and dusting the household—but making sure to get down and dirty! Watch…
Reyna De La Cruz is having some naughty fun in front of the mirror, taking sexy selfies for her boyfriend while playing with her sweet pussy. Only problem is she…
Ryder Monroe is a senior member of her cheerleading squad, and she’s worried about being cut as the new girls come pouring in. So Ryder works it out with her…
Valentina Nappi visits her friend in LA and takes her car for a spin, but the car ends up running out of gas! She calls roadside assistance and a sexy…
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…
Jack is really busy casting for music videos and now he’s on the hunt for big, beautiful boobies. They bounce, and they shake. There’s more than a mouthful, more than…
Bailey is watching lesbian porn and masturbating in her room. All of the sudden her roommate Noemie walks in to ask her something and catches her. Mortified, Bailey slams her…
Joslyn, a DIY crafting enthusiast, bought the wrong shade of paint for a mason jar vase she’d be dying to make ever since she saw it online. However, when she…
Topaz is the prettiest dark dick sucker in this flick. She maintains eye contact whenever possible – but when this clip concludes even she can’t keep her eyes on the…
All any schoolgirl wants is a big fat dick that will make her eyes twinkle with desire, and send a rush of wetness to her tight pussy. After lecture, another…
Celeste’s Icon features an amazingly beautiful, all-star cast in some of the hardest scenes they’ve ever shot. Digital Playground’s contract superstar, Teagan Presley leads the way, down a revealing and…
Housewife Blair is handing out candy for Halloween. When Sadie shows up on her doorstep, Blair is suspicious – Sadie may be small, but Blair’s not sure if she’s young…
This John has always had a thing for bringing strong women to their knees. When he meets sexy tranny hooker Foxxy, he knows he’s met his match! She spends lots…
Natty’s boyfriend Charlie hasn’t fucked her in a year, but there’s another dick in the house that she just might like even better! Charlie’s brother Jordi seems to spend all…
When it comes to music, guitar goddess Leigh likes it loud. Her older neighbor Tommy, however, feels the exact opposite. While Tommy used to do a little shredding back in…
Wearing nipple pasties is fun and makes this horny petite Asian girl feel sexy as she gets on her knees and services this hairy dick with her tongue. She loves…
