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Diamond Jackson is a newly divorced milf eager to find a young, thick cock to fuck, so she drags her married friend Simone to a bar to help her pick up guys. With none in sight, Diamond is getting hornier by the minute. So when Simone steps out to call her husband Diamond quickly seduces...
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Diamond Jackson is doing some yoga in her yard when her neighbor sneaks in to watch her. He confesses that watching her do those sexy poses turns him on. Diamond takes this as a compliment and decides to ride his big cock.
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The Window Watcher Danny D’s job as a window washer isn’t always rewarding, but his luck is about to change. Busty businesswoman Patty Michova is feeling flirty and she likes the way Danny handles that squeegee. She gives him a little tease of her big tits before sucking his massive cock through her expertly cleaned...
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Diamond Jackson’s new husband convinces her and his son, Justin Hunt, to spend some quality time together watching the game. Diamond is more interested in Justin than in the game, and tries to get him off with her husband right beside her. Starting out with an innocent handjob, she fakes a chill to be able...
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Milfy Diamond wants to get her son onto the college soccer team, but he hasn’t made the cut! Determined, Diamond drags him over to Coach Dupree’s house to demonstrate his worth. While her son fumbles with the ball, Diamond decides it’s time for more desperate measures. Sneakily, Diamond gets on her knees and sucks the...
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JMac and Levi sneak into their friend’s house to play a prank on him. They are out to embarrass their friend by raiding his mom’s pantie drawer. Their friend’s mom, Diamond Jackson, comes home early and catches them in the act. She decides since they want to see her panties so badly that she might...
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Our boy Juan is in the shower fantasizing and jerking off. His stepmom Diamond comes into the bathroom and ready’s herself for a shower. Not knowing what to do, he peaks through the curtain as the buxom cougar takes her clothes off. Mesmerized by her big giant titties and slamming body, he decides to try...
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Diamond Jackson took her student’s phone away for having it in class. She also found pics of his dick on the phone. She can’t believe how big it looks in the pictures so she makes her student whip it out to prove its length. Once she gets her eyes on it she can’t help but...
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Fine, I’ll Fuck Your Son Courtney couldn’t get Marcus to give her the D. In desperation Courtney walked down the hall to her new step-son’s bedroom. When Courtney rolled down his boxers, the surprise of her life awaited her in the form of a foot-long dick that made her wet. Courtney hopped on and rode Danny...
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Diamond always rides her staff hard, and today is no exception. A perverted employee is spying on her and she’s ready to put him through the ringer. Once he gets a taste of her wet pussy he’ll remember who’s in charge!
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All this work on her wedding is stressing her out like crazy, but her wedding planner, Diamond Jackson, knows just how to help! Undressing her blonde client, Diamond fingers and licks every inch her sweet, wet pussy. It’s been a while since Aspen has had her pussy played with but even longer since she’s been...
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Diamond Jackson has a problem student in her sexuality class. He thinks he knows it all when it comes to pleasing women, but Diamond has a few tips for him to learn.
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Diamond Jackson is tired of her lazy-ass, good-for-nothing son. He’s supposed to be fixing a coffee table for her, but instead she finds his buddy Bambino doing the handiwork in the living room. He said he’s doing the dirty work because he owed her son a favor, but Diamond still isn’t pleased. She asks Bambino...
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Diamond Jackson and Nikki Benz are enjoying a friendly tennis game when suddenly they’re approached by a ball boy, Jordi El Nino Polla. Jordi tries every excuse and chance he can get to be closer to the action—that is, closer to the ladies’ tits and asses! Diamond and Nikki serve up some hot fucking to...
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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 be anything but relaxing as Diamond demands a proper fucking from her willing masseuse.
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