Diamond Jackson - Diamond Jackson and Kris Slater in Tonight's Girlfriend (Tonight's Girlfriend)

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Scene Description

I've been hanging out for a few days with my boys for one of their bachelor parties. The bachelor had a great time, but now it's time for me to have my fun. I call my favorite porn star, Diamond Jackson, over for the night. I've been a very bad boy during this bachelor party and tonight I want Diamond to punish me for it.

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Diamond Jackson and Kris Slater in Tonight's Girlfriend (Thumb 01)
Diamond Jackson and Kris Slater in Tonight's Girlfriend (Thumb 02)
Diamond Jackson and Kris Slater in Tonight's Girlfriend (Thumb 03)
Diamond Jackson and Kris Slater in Tonight's Girlfriend (Thumb 04)
Diamond Jackson and Kris Slater in Tonight's Girlfriend (Thumb 05)
Diamond Jackson and Kris Slater in Tonight's Girlfriend (Thumb 06)
Diamond Jackson and Kris Slater in Tonight's Girlfriend (Thumb 07)
Diamond Jackson and Kris Slater in Tonight's Girlfriend (Thumb 08)
Diamond Jackson and Kris Slater in Tonight's Girlfriend (Thumb 09)
Diamond Jackson and Kris Slater in Tonight's Girlfriend (Thumb 10)
Diamond Jackson and Kris Slater in Tonight's Girlfriend (Thumb 11)
Diamond Jackson and Kris Slater in Tonight's Girlfriend (Thumb 12)
Diamond Jackson and Kris Slater in Tonight's Girlfriend (Thumb 13)
Diamond Jackson and Kris Slater in Tonight's Girlfriend (Thumb 14)
Diamond Jackson and Kris Slater in Tonight's Girlfriend (Thumb 15)
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Diamond Jackson in Seduced by a cougar

Diamond Jackson - Seduced By A Cougar

27th August - Ryan locked his keys in his car and went to a nearby house to use a phone to call for help. After making the call, Ryan hears the bad news that it's going to be at least two hours for someone to get out there. The good news is that he's stuck with the lovely Diamond and she knows just what to do to pass the time. ...Read More
India Summer and Diamond Jackson in My Friends Hot Mom

Diamond Jackson - My Friends Hot Mom

15th August - Diamond Jackson & India Summer really want to make sure that their kid's soccer team wins this season so they invite the new referee over to try and persuade him over to their side. They offer him everything from sticky buns to clothes, but he doesn't budge. Finally they give him something no man can resist: their two lovely pussies. ...Read More
Diamond Jackson and Kyle Mason in Seduced By A Cougar

Diamond Jackson - Seduced By A Cougar

31st May - Diamond Jackson has been dying to take ballroom dancing lessons, and she finally landed an instructor to come to her house and show her some moves! Her instructor, Kyle, arrives and shows her some basic steps to the seductive art of salsa. But apparently he does it so well that he gives himself a boner in the process! The hot cougar can't help but notice the bulge in his pants, especially when he's pressing up against her while they're dancing, and she takes full advantage of it — the way a cougar should. The busty black goddess is no sooner on her knees sucking Kyle's big dick and showing him how to do the sideways hokey-pokey! ...Read More

Diamond Jackson in My First Sex Teacher

Diamond Jackson - My First Sex Teacher

2nd October - Diamond Jackson consoles her student after he's been dumped by his girlfriend. Diamond decides that the best way for him to get over his ex is by fucking some new pussy. Being the loving educator that she is Diamond offers up her pussy to help her student in his time of need. ...Read More
Ariella Ferrera and Diamond Jackson and Bambino in My First Sex Teacher

Ariella Ferrera - My First Sex Teacher

7th April - Arielle Ferrera gets called into the college because her idiot stepson Bambino did something stupid in class — he pulled his big dick out on a dare! His professor, Diamond Jackson, has a talk with Ariella and him about all this and cautions them that she may need to involve the dean. She has her student show his stepmom exactly what he did, but nobody can believe how massive his cock is when he wriggles it out of his pants! Professor Jackson and Ariella confer in private and make a determination: they're willing to is willing to overlook things if Bambino fucks them in a professor-stepmom threesome! Do you think he'd dare?! ...Read More
Diamond Jackson and Bambino in My Friend's Hot Mom

Diamond Jackson - My Friends Hot Mom

10th April - 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 to relieve some of her stress by giving her a massage … on her big tits! He's not so sure of it, but when Mrs. Jackson tells him her husband is away at a poker game for hours and her son's out being a dumbass, Bambino's all in on the hot MILF's pussy! Ebony hot mom Diamond's sexy stockings and dirty talk get Bambino's big dick so hard that he's working with more wood than the coffee table! ...Read More
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Diamond Jackson - Bra Tug of War

Diamond Jackson - Big Tits In Sports

22nd January - Diamond and Isis have battle long and hard throughout the season and today is the championship match. The are experts when it comes to bra tug of war. When the last tug ends up being a tie the two girls do whatever they can to persuade the referee to lean towards them. Their tits are out and their pussies are dripping with wetness. ...Read More
Diamond Jackson - Weremilf

Diamond Jackson - Milfs Like it Big

31st October - Diamond Jackson is usually a great mom, but every time there's a full moon, the mystical power of the Weremilf takes over and she has to find some dick! She tries getting herself off with a big dildo, fucking her pussy until she cums, but there's no substitute for the real thing, so Diamond goes downstairs to find her daughter's study buddy Brick Danger. She gives Brick an incredible deepthroat blowjob, and then he eats her ebony pussy until it's dripping wet. He fucks her deep in every one of her holes, and after some sweet anal sex he gives her the big facial cumshot that she craves! ...Read More
Diamond Jackson - One Ride Two Brides

Diamond Jackson - Real Wife Stories

8th October - Rick decides to satisfy his craving for Yankee pussy by ordering himself an American mail order bride. In his excitement, he orders himself not one, but two wives, and has them compete over who will get to be Mrs. Anthony. ...Read More

Diamond Jackson - Dick Crazy Milf

Diamond Jackson - Brown Bunnies

30th August - Diamond Jackson...........WOW! That is all I can really say after watching the Best Milf in the business, do her work. This is a fine example of experience taking over. From the beautiful throat gaging blow job, to the deep hardcore ass fucking I guess the best way to describe this scene is.....FLAWLESS!!! ...Read More
Diamond Jackson - Corporal Pleasurement

Diamond Jackson - Big Tits at School

19th November - Diamond Jackson's heard all kinds of rumors about one of the teachers on her staff. It seems Mr. D's been leaning a little hard on his female students, and it made her eager to see for herself what his unique take on discipline means. Diamond called him into her office to make a close appraisal of his technique, and get a little taste of his open palm spanking her thick mocha ass. All that filthy foreplay got this Milf Ms. Jackson so excited, she spread her legs wide open to fuck his massive rod. ...Read More
Diamond Jackson - Anal Creampie In POV

Diamond Jackson - Brown Bunnies

22nd November - Today's BrownBunnies features the always sexy Milf, Diamond Jackson. The lady is a motherfuking handful I tell you. She loves to suck dick and loves to be fucked deep, in both holes. This Milf will talk dirty to you just the way you like it. Hell, you might bust a nut before the action starts. JMac gave to her just how she loves it! He fucked her deep and hard. Gaping that asshole out, leaving it full of cum. Enjoy! ...Read More