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….

Sasha Pearl is hanging out, getting a little sun, when her boyfriend’s son stops by. Like always, he’s upset that Sasha does nothing while his dad works his ass off…

You can’t be bored when you’ve got a hot, perfect body like Tasha Reign’s! Right before she was supposed to film a scene, Tasha whipped out her sweet boobs and…

Jana Cova is “Porcelain.” This intimate and artful production shines new light on Digital Playground’s exclusive contract super star, Jana Cova. In this glamorous and smart vignette, director Celeste effortlessly…

Kira Noir is a hot and naughty lawyer heading to the courtroom. A routine metal detector turns out to be anything but when baliff Kyle Mason finds a butt plug…

Mischievous MILF Liza’s new star gazing hobby is a lot less innocent than it seems. While most astronomers set their sights on the sky, Liza has her telescope aimed at…

Aidra has been housesitting for the Lees for awhile now, but she can’t get Mr. Lee to notice her… That is, until she makes him a solo sex tape. Keiran…

All Natural Facials Kira and her bestie Ryan are always down to try the latest beauty treatments as long as they can keep it all-natural of course! The latest trend…

Beautiful MILF Tucker Stevens gets a sexy and sinister idea when her stepdaughter goes to her doctor’s appointment, leaving behind her young, lesbian girlfriend, Ashlynn Taylor. Olive-skinned Ashlynn is relaxing…

After his wife is killed, the Finisher is on the hunt for the men complicit in her . As he moves in the darkness, picking off the men one by…

Jay’s birthday is coming up, and Sydney is doing everything at hand to be the coolest stepmom about it. She wants to throw a big party for him and she…

Tiny Beauty Has Crazy One Night Stand L.A. is full of influencers, and tonight Rose runs into one of her favorites. Rose isn’t normally one to be star struck, but…

Unfaithful Kendra Sunderland has an insatiable appetite for sex. When her boyfriend Van Wylde has to work late one evening, Kendra is so horny she has no choice but to…

Amirah Adara just can’t do anything right in the eyes of her step-mother Martina Gold. When Amirah joined Martina at the table for breakfast, she caught hell for every little…

I have consulted many ass loving guys and Naomi came up several times. We decided to shoot a scene with Naomi and her perfect ass. We started her of in…

In “Jesse Jane: Sexual Freak,” Jesse Jane® is at an all time high. Her insatiable lust and her pure power are exploited and showcased under Robby’s artful direction. Watch her…

Tom is in his car, watching Claire changing through her open window, when he gets busted by Claires busty mom.

Nicolette has just helped Keiran buy a house. Ever since they met there’s been sexual tension, despite his wedding ring. Once their business is out of the way this sexy…

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…

Baby Got Boobs Vol. 20 Ashley is a wild cowgirl working the mechanical bull, but she’d rather take Robby for a ride. There’s nothing quite like getting bucked and fucked….

Restaurant manager Eva Angelina just got caught stealing money from her boss. Now, rather than fire her, her boss is giving her an opportunity to keep her job. Eva had…

Sia Lust is an adorable blonde teen that just turned 19! She looks a whole lot younger and she loves outdoor and public sex. She wants to get fucked in…

When Ashley comes into town for a visit, she’s out to find some fresh new cock. But when she’s offered a place to stay in her best friend’s house, it’s…

Sexy redhead Lacy Lennon is preparing dinner for her boyfriend, only for him to call and cancel their date over the phone! Worse than that, the no-good boyfriend wants to…

Victoria Rae Black went to the massage parlor with one goal in mind: to catch her friend’s man getting a happy ending to his massage. But when she walked into…

Jenny is super excited to finally get Jordi to take notice of her at the local college. She takes advantage of the situation, making Jordi walk her home. However, Jenny…

Class is dismissed and everyone is checking their grades, which means bad news for Alex who’s failing the class. It’s not his fault though, with a professor as hot as…

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…

Uploaded: 2024.02.06 2024.02.06 Show more…