It’s that magical time of year again: holiday parties, office shenanigans, and receiving a big, fat Christmas bonus. At least it should be, but after last year’s messy holiday bash,…

Your doctor is overloaded with clients, so he sends Nurse Chloe Cherry to tend to you while you wait. It sounds like the doc’s gonna be a while, so why…

What the fuck! Chloe Lamour and her roommate have a lot in common already, with their brunette hair and big round tits, and now they’re both wearing the exact same…

On this very special episode of Yoga Freaks, Jade Jantzen enters the studio ready to give it her all. Yogi Master Xander blindfolds his young student to enhance her experience,…

Pussy Payment Sexy blonde Venera Maxima checks into the Fake Hostel, and after letting Steve Q sniff her panties, the ever-horny vixen helps herself to his long, thick cock! With…

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…

Jimmy Michaels has to make a shirt for a home ec assignment, starting with measuring the person who will be wearing the shirt: his own stepmom, Sophia Locke… Uploaded: 2024.03.06…

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All the screamin’ hot sex in Digital Playground’s award winning Jack’s Playground series are now shot in POV perspective for your ultimate enjoyment. In Jack’s POV Playground, YOU will get…

Your dad is a deadbeat and his new girlfriend is hot af. You know she deserves better…better like your bigger harder cock pounding out her sweet MILF puss. Don’t let…

The grand finale brings us Deja Vu. A nineteen-year-old cutie with a petite little frame. Deja takes on T.T. Boy in a wild interracial closer that provides a fitting send-off….

Beautiful and busty Kylie Paige is a mathematics whiz who is a big slut underneath her nerdy demeanor. While she acts like a know-it-all, Kylie just wants to get at…

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Tyler is having a hard time learning French. Luckily his teacher, Cassie Del Isla, believes that no student should be left behind and she is willing to take out-of-the-box measures…

Seeing her ex, Eddie, with his new girlfriend was the motivation bootylicious brunette Mandy Muse needed to go out and get him back. Mandy’s feeling better and looking hotter than…

Katrina Colt finally found a nice and relaxed place to stay with a nice landlord. He confesses to her that he’s also a big fan of her work. Katrina is…

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Latina stunner Mary Jean is dragged to a mysterious and sexy masquerade party by her friend, who quickly disappears in the crowd. Mary Jean goes off exploring on her own,…

John (Charles Dera) and Emma Smith (Ryan Keely) are looking for a new country home so they can finally move out of the big city with their teen daughter, Charlotte…

Kawaii Boku, the sweet little Asian brunette, invites her boyfriend up to play with her at her parents’ house. He plays with her cunt hard and then she sucks his…

Social media influencer Kenzie wants to make the leap to professional slut, but not all of her followers believe that this tiny girl is able to take a porn-sized cock….

In an underground sex world, a masquerade ball is taking place with Abigail Mac’s body as the prized possession. Her tantalizing legs and voluptuous breast are everyone’s desires, because she’s…

The sexy Phoenix Marie thinks she has the house to herself today, but she’s surprised when her husband comes home early to watch a sports game, with his friend Johnny…

Sometimes Susie gets really horny working all day as a nurse, so she changes into some more comfortable clothes during her lunch breaks, and follows the doctors to a secret…

Hot babe Victoria Lobov tries to take a nice, relaxing bath, but her husband’s sneaky brother, Jmac, slips inside the shower with her. After a moment of shock and hesitation,…

Brick Danger just got a new job at the prestigious company Goldmilf & Ballsachs, one of the leading voices in sex-related investments. He’s nervous on his first day, and as…

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It’s day two here with We Live Together, and our girls are waking up after a long day of orgies, filming, and figuring out how they mesh with one another….

When big-titted, blonde gyaru Kyouka is asked to take care of an important customer while all the other girls at the brothel are sick, she calls up her nerdy friend…

Now that Jessica Jaymes has learned to love her husband’s mistress, sexy slut Jaclyn Taylor, the two busty beauties have come up with a sneaky plan to scare the jizz…

Look who’s back!! Super sexy Cody Lane is here again for some hard oily action. This girl’s body is out of this world and that ass!! Man, that ass is…

Sophia Locke is back on Device Bondage, which started her journey with Kink. Today she is reunited with The Pope and begins her day in a predicament position with her…

When Antonio’s latest patient is down for the count, sexy nurse Misha Cross takes the chance to make her move. She straddles the big-dicked doctor, making her lusty intentions clear,…

Uploaded: 2024.01.07 2024.01.01 Show more…

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….