Jack’s casting again! This time he’s looking for leg models… sexy, leggy vixens who want to be in fresh, up and coming music videos. In the first volume, Digital Playgrond’s…
Goddess Tina Kay is lounging in the pool and sucking on a long, stiff frozen treat. Sexy Tina has made herself sticky, so she uses the warm water to drench…
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…
Ellie Eilish just turned 19 and she is down to fuck! She twirls around in the park and shows off her pretty pussy! She isn’t wearing any panties and she…
Aspiring artist Cadence Lux reveals her sexy lingerie look in an avant-garde performance art piece. The crowd is mesmerized by her sensual dance moves under the moody light of a…
Freshly fucked by Monique’s stepson, Peta is worried she’s in big trouble when she’s summoned to her boss’s room. But Monique just wants Peta to clean up the mess she…
After getting fired from the sperm bank for being "over-enthusiastic" in her duties, Rebecca More decides to start a freelance sperm bank out of her home. Luckily for donor Danny…
Britney Amber would like to sell her 3-wheeler to her boyfriend’s son Billy, but he laughs when she tells him the asking price of $100,000. Britney learns from Billy that…
A Christmas Surprise From My Boyfriend’s Roommate It’s Christmas, so what better time for the classic gift of cock prank? Mischievous Jordi cuts a hole in a holiday gift box…
Octokuro has a chat with cameraman Raul Costa as he gets set up for today’s shoot. She’s showing off her college student outfit on her channel, and after lots of…
Natasha Nice is due for her daily pampering, but her masseuse had to leave suddenly. Thank goodness the newly hired housekeeper was there to get hands-on training. Natasha’s giant round…
Fashion designer and model Ivana Vaughn (Emma Hix) will stop at nothing to be queen fashionista, with her latest ultra-provocative fashion line turning heads throughout the industry. Ivana’s archrival, Armand…
Jack is really busy casting for music videos and now he’s landed Digital Playground’s super fine contract star, Teagan Presley. She takes a big cock in the butt and we…
The sexy Kendra Spade has invited some of her girlfriends over for a pajama party; romantic movies, popcorn, pillow fights! This catches the attention of her pervy neighbor Kyle Mason…
It’s such a beautiful sunny day, Henessy decides to take a trip to the topless beach. The boardwalk is deserted when she spreads her towel out and lies down to…
“Big Dick” Agent,Cody Lane, was out searching for the next “BIG” thing when she came across the perfect specimen, Billy Glide, for her dick deprived client. Once she saw the…
Parker is printing some pics to give his sweetheart for Valentine’s day when his dad’s girl, Wendy walks in. As Parker is printing the pics, Wendy catches a glimpse of…
Jordi’s girlfriend brings him to Clea Gaultier’s school of etiquette so he can learn how to be a proper gentleman before meeting her wealthy family. Clea is very difficult to…
Take Yukina Mori by the hand, lead her away from what she’s doing, tie her up and gag her. After all, that’s all Yukina desires! The more dicks you give…
They say we’ve all got an angel and a devil on our shoulders, but what happens when the two are left alone in the bedroom? The sexy devil, Abigail Mac,…
Just walking down the sidewalk and pass a hot babe, Ameena, who needs directions to the park. I love these girls that move here from other states. They are so…
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….
Summer Brielle was doing some yoga at her friend’s place when her pervy boyfriend Tyler Nixon came home and started watching them stretch in their tight yoga pants. Summer played…
