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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…

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28 min
Hot Teen Blonde Ashley Alexander gets filled up with her friend’s dad’s cum
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Ashley Alexander is over at a friend’s house waiting on her to come home, when her friend’s dad Scott see’s her on the internet he has some questions to ask….

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Aaliyah had a whole erotic surprise worked out for her boyfriend this evening, and she pulled it off with ease. As soon as Logan opened the door to their bedroom,…

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Jack’s Playground 32, features Digital Playground’s contract babe, Sophia Santi, eager to make it in the music video scene. She shows her distinct talents and raw, exquisite beauty in two…

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43 min
Abbie Maley Gets Her Pussy Wrecked After a Hot Shower
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James Deen walks in on Abbie taking a shower. Once Abbie is done with her shower, she joins James in the living room where she starts giving James a sloppy…

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Shawna Lenee isn’t above using her big tits and oozing sexuality to sell cars at the dealership. After giving up her gig as a porn star, she’s been doing whatever…

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Make You A Man
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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….

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36 min
Sexy MILF Andie Anderson has an intense affair with her son’s friend
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Andie Anderson hasn’t had sex in a very long time because her husband won’t fuck her anymore. She is in desperate need of some cock and an orgasm! She figures…

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Nurse Sarah provides her patients with the very best care, but she expects them to thank her with a hard fuck once they’re all better. After tending to Mr. Lee…

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Digital Playground presents DP Star: Season 2, hosted by last year’s DP Star winner and contract girl, Eva Lovia and judged by industry legend Nikki Benz, renowned producer/photographer Holly Randall…

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Newly stated doctor Savannah Stern is having trouble this morning with a reoccuring patient. He has griping about chest pains and has been to her office three times now and…

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27 min
Stuck On The Cock
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Kenzie Reeves has the hots for her new tutor, Alex Legend, and she has decided to tell him. But he denies her! Embarrassed, she gets up to leave and accidently…

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When it comes to sex, aggressive Adriana isn’t afraid to get a little messy – she’s not satisfied until she’s drenched with sweat, spit and spunk. When makeup starts streaming…

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Bitchy boss Diamond Jackson is so uptight that upper management has decided to pay for her to get a nice relaxing massage. Unfortunately for them, the massage turns out to…

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Chrissy Davis is the talk of the town following a very public mental breakdown and first-degree charge. She’s quickly alienated by her high society friends and left alone to suffer…

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Keiran hires masseuse Subil to help him relieve his tension. He’s never heard of the Russian massage ‘strokemoff’, and decides to give it a try. After a while of sensually…

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22 min.
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52 min
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When Molly (Jane Wilde) takes on her friend Alice’s repeating day burden, she thinks that it will all be hustling mobsters and robbing banks. Though she’s not wrong, what Molly…

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35 min
Fucking On The First Date
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Ricky Johnson’s first date with the stunning Kenna James is off to a rocky start when he spills her drink on her and burns the appetizers. Lucky for Ricky, Kenna’s…

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