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….

Lily Glee has a date tonight, and she has not idea what she should wear. Luckily, she can ask her roommate, Tyler Nixon, for his opinions. She shows him her…

Young Bella Elise Rose is at one of her parents boring dinner parties when something in the room catches her eye. Ryan Mclane is the manager of the catering service…

Cute, young couple Mary Rock and Josh are hanging out and watching a movie. Meanwhile, Mary’s sexy stepmother, Nikky Thorne, is soaking her gorgeous body in a warm bath. When…

Stunning Alyssia Kent and Gerson Denny get soaked from the rain and have to take shelter inside. Amazing Alyssia’s white tank top gets sheer from the rain, Gerson can’t take…

Shot entirely on HD, Jack’s Teen America 20 features Digital Playground contract stars, Shay Jordan, Sophia Santi and Jana Cova with industry babes Hillary Scott, Holly Morgan and Sue Diamond….

Anya Krey is a complicated woman with many needs. With a husband who is abroad more than he is home, she finds herself with some of her most demanding desires…

Gorgeous, curvy Bailey Brooke is cooling down in an outdoor shower, it’s hot outside and Bailey is just trying to beat the heat. When Quiton James stumbles upon big-breasted Bailey,…

Red-headed Gala Brown is sunbathing on the beach when Stallion jogs past her – Stallion hasn’t noticed beautiful Gala yet, but she’s going to change that. Tanned Gala takes off…

Curvy and delicious Ella Knox has one fetish – to be fondled, fucked, and admired in a pair of beautiful, sheer panties. Gorgeous Ella shows off in a pair of…

What’s more dangerous than a conman? A gang of con-women! Federal Investigator, Emily Willis, is hot on the trail of a con-gang that has been wreaking havoc across the city,…

Casey Calvert is so horny, so she really needs to let off some steam. Thank goodness her sexy cleaning guy Seth Gamble is in the kitchen scrubbing the floors. Casey…

Amazing Lauren Phillips strolls into the room, oozing with sexuality and confidence. Busty Lauren blesses you with a striptease that you won’t forget – she fondles her incredible, big breasts…

In Part 4 of Fleeced, Investigator Emily Willis finally gets the breakthrough she needed! Beautiful Emily is hot on the tail of an infamous, all-women con gang and she won’t…

Lika Star has the house to herself, but she’s hard at work. Ever the dutiful maid, Lika works to get the house in order just to the owner Alberto Blanco’s…

Day jobs pay the bills, sure. But we all need our real passion – a way to give our lives a healthy dose of vigor. Lacy Lennon is a teacher…

Enjoy Digital Playground contract stars Jesse Jane® and Stoya in LUST, a provocative, playful and passionate film by Celeste. Lust is an anthology of lushly sensual affairs, featuring Jesse Jane…

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…

Going door to door, Riley Reed needs to hit her sales quota before the night is up. At the last stop, her wet mouth is more convincing than her talk…

Alberto Blanco has a special Valentine’s Day gift for his stunning wife, Baby Nichols, and she’s got something for him, too! Nichols greets Alberto clad in lacy, black lingerie and…

Blonde athlete Macy Marx is here to show all her fans an exercise routine they can do at home to really work up a sweat! After changing into her tight…

As soon as Timo saw Foxy Di come out of the shower with her chest dewed with droplets, and a gorgeous flush on her skin, he had to have her…

Natalia Starr knows what she wants and she’ll do whatever it takes to get it. For quite some time this seductive siren has had her eye on security guard Brad…

Lucas Frost was planning on going out, but when he spots his hot blonde stepmom Nina Elle sunbathing nude and playing with her pussy and a fat butt plug, he…

Jessa Blue has fixed her man, Damon Dice, a home-cooked breakfast, but not even the smell of bacon tempts him out of bed as fast as the sight of her…

When Donna’s man got home, she was hiding out in the bedroom, waiting to spring a sexy surprise. Donna hopped out of a wooden chest wearing her most cleavage-revealing top,…

Blonde Britney Amber and her husband, Steve Holmes, have a sinister plot to fill young, beautiful women with Steve’s seed. So, when Steve catches petite Eliza spying on him over…

The best way to wake your husband is by gently dragging the tips of your fingers down his chest and then wrapping your hands around his throbbing prick. Courtney woke…

In The Breeders: Part 3 blonde Gia Derza approaches her professor, Steve Holmes, with a question about DNA. However, Steve is upset with his wife and he’s ready to take…

Gorgeous Gia Paige has a kink for dressing up – she can’t help but come home, get out of her drab work clothes, and into something a little more deviant….

Longhaired Nicole Pearl is putting on a sexy show for her webcam when Raul Costa catches her. Petite Nicole has already gotten herself warmed up, what’s the harm inviting Raul…

It is gorgeous Marica Hase and her husband’s anniversary and Marica’s husband has a special gift for his beautiful wife. He leads dark-haired Marica by the hand to her handsome…

Blonde Kristina Shannon is nerdy on the outside but underneath that reserved exterior is a sexy, secret obsession! Tanned Kristina used to steal her mother’s stockings and try them on…

After a hard day’s work, Ferrera Gomez and her partner Clarke Kent don’t hesitate. The busy couple knows that in a modern world, you must take your tender moments whenever…

Whenever Tyler Nixon comes home to find his girlfriend Tiffany Tyler wearing her high leather boots, he knows he’s in for some really hot sex. This one night, Tiffany didn’t…

Starring Digital Playground’s newest sensation, Shay Jordan and an entire cast of young, gorgeous, almond eyed beauties, Jack’s Asian Adventure will please your pallet. Jack uses the tried and true…

Starring Digital Playground’s newest sensation, Shay Jordan and an entire cast of young, gorgeous, almond eyed beauties, Jack’s Asian Adventure will please your pallet. Jack uses the tried and true…

Starring Digital Playground’s newest sensation, Shay Jordan and an entire cast of young, gorgeous, almond eyed beauties, Jack’s Asian Adventure will please your pallet. Jack uses the tried and true…

Starring Digital Playground’s newest sensation, Shay Jordan and an entire cast of young, gorgeous, almond eyed beauties, Jack’s Asian Adventure will please your pallet. Jack uses the tried and true…

Starring Digital Playground’s newest sensation, Shay Jordan and an entire cast of young, gorgeous, almond eyed beauties, Jack’s Asian Adventure will please your pallet. Jack uses the tried and true…