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…
Ri-Ai Saotome is a horny slutty Japanese newbie with big round tits and an extra hairy cunt. She wants to make a good impression with her first time on camera…
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…
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…
Stepmom Taylor Vixxen is folding laundry when she hears her Stepson arguing from his bedroom. She starts thinking to herself, even though she shouldn’t intervene in his affairs, she is…
Paige Owens has a mouthful of Isiah Maxwell’s hard cock when the doorbell rings – she forgot she scheduled 2 booty calls today! Not one to waste an opportunity to…
Busty professor Bridgette B is waiting for you to finish your exam. But, like the dirty pervert you are, you can’t finish because you’re distracted by her tempting titties! Will…
Scarlett Bloom thinks she’s hit the jackpot when the dude she met at the club takes her back to his lavish home…only he blows his load moments after she pulls…
Danny has decided to take his relationship to the next level and finally move in with his girlfriend. The one thing he isn’t quite ready for is meeting her daughter,…
Nurse Connie Carter has a bit of a a weakness for badboys, but working as a day nurse in a sleepy little suburban borough, the last thing she ever expected…
Walking into a new flame’s apartment, this guy was so surprised to see every manga and toy on her shelves, a perfect collection that got him so excited to fuck…
Curvy masseuse Lela Star has invented an entirely new massage technique that only involves using pressure from her huge ass to work her clients’ aching muscles. She also has a…
Red is definitely Addis Fouche’s color as she sunbathes in a bright one-piece. Addis needs some more oil, and as she rubs it on her smooth skin while chatting with…
It’s 18-25 only in the city’s most popular club, and Danny D’s got a fake ID! Determined to get in and flirt with some pretty younger women, there’s only one…
Danny is on his way over to Michelle’s house to fuck her brains out, but discovers her husband is working from home that day. Before leaving he intercepts a mail…
Devon puts in long, hard hours working at a secretary for multiple businessmen. She brings them coffee, answers their phones, lets them play with her huge tits, and sucks their…
As Jennifer lounges seductively on her suede leather sofa, the angelic beauty is indulging in her naughtiest fantasies. Missing the feeling of a lover’s touch, she feathers her fingertips across…
Tanned brunette teen Darcia Lee just can’t stop peeking at her silver fox stepdad Yanick Shaft and fantasizing about feeling his strong hands on her body. Darcia’s signals grow more…
The sexy Emily Addison sneaks over to her hated sister’s home to help herself to some jewelry and other belongings. The casual thievery is going well, until Emily gets caught…
The sexy Annabelle Rogers is having a blast in the pool, playing with her big wet tits. Once she gets out of the water, she decides to tease the viewer…
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….
Nothing better than having a maid coming by and helping me clean around the house. This time around they sent the most beautiful young blonde with a perfect ass and…
Famed monster hunter Gerald of Vulvia can’t stay out of trouble. He’s always on the hunt for his three favorite things: money, combat, and – most important of all –…
