Diamond Jackson - Corporal Pleasurement (Big Tits at School)


Scene description

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.

Scene Tags

Big Dick Worship, School Fantasies, Femdom, MILF, Ebony, Brunette, Big Tits, Principal, Ass Worship, Big Tits Worship
Big Tits At School


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Diamond Jackson - Corporal Pleasurement (Thumb 09)
Diamond Jackson - Corporal Pleasurement (Thumb 10)
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Big Tits At Work


Diamond Jackson - Mom Catches The Babysitter

Diamond Jackson - Moms in control

21st December - When Diamond Jackson caught her slutty babysitter Trinity St Clair fucking her boyfriend Jessy, Trinity thought she was done for. But Diamond, cock-hungry MILF that she is, just wanted to teach Trinity how to suck dick properly! Diamond showed Trinity how to give the best blowjobs, with deepthroat gagging and lots of sweet sloppy action. Jessy worked through every hole in the room, fucking both of those sexy sluts in their pussies and tight assholes, and then ending the epic anal threesome with a huge pussy creampie! ...read more
Diamond Jackson - To Prank A Skank

Diamond Jackson - Mommy Got Boobs

30th August - Diamond is a naive sweetheart who is always the subject of her daughter Kat's non-stop practical jokes, so when Bill comes over claiming to be her daughter's boyfriend, Diamond assumes it's just another prank. She decides to test his resolve by coming on to him, but when he doesn't crack, she pulls out the big guns, namely, her big tits. ...read more
Diamond Jackson - Millionaire Squirter

Diamond Jackson - Shes Gonna Squirt

27th December - Diamond is an extremely busy lady in serious need of some cock. She's rich, horny, and on a mission, so she calls up an escort and makes him a deal: if he makes her squirt, she'll give him a car. Get pounding, Toni! ...read more
Big Tits In Sports

Diamond Jackson - Gimme That Dick

Diamond Jackson - Doctor Adventures

9th March - When Erik's busty neighbor Diamond Jackson invited him over for a drink, he didn't expect to get laid. But as soon as he walked through the door, that big-titted slut went straight for his fat cock! She took that big dick balls deep in her throat and tight pussy, and Erik was so shocked that he ended up in the hospital! He thought he was in the clear, but as soon as the nurse left him alone with the doctor, she revealed herself to be none other than his horny neighbor Diamond! One look at her incredible big tits and Erik forgot all of his fear, fucking her titties, her pussy, and even her tight little asshole before busting a huge load all over her face and big tits! ...read more
Nikki Benz - Game, Set, Match Pussy

Nikki Benz - Big Tits In Sports

30th August - 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 the perverted ball boy! ...read more
Diamond Jackson - My Sister-In-Law Is A Whore

Diamond Jackson - Milfs Like it Big

24th January - Diamond Jackson is a busty ebony call girl who loves big cocks, and Erik Everhard is the horny John who called her up. Only one problem, though: Erik is married to Diamond's sister! At first she says he can look but not touch, teasing him in her sexy lingerie, and stripping down to nothing but a pair of heels, some black stockings, and a set of garters. Her tune changes as soon as gets a glimpse of Erik's big dick, though! As soon as she gets her hands on that fat cock, she has to stroke it, suck it, and fill all of her holes with it. Once Erik has fucked her in her mouth, pussy, and tight little ass, he blows a huge load all over her face. Here's hoping they can keep a secret! ...read more


Diamond Jackson in My Friends Hot Mom

Diamond Jackson - My Friends Hot Mom

13th November - Bill stops by to pick up some of his friend's stuff from his friend's mom's, Diamond Jackson's, house. Diamond sure is lonely now that her son is out of the house. Bill decide that all his friend's mom needs is something to help her forget about her loneliness....something like his cock. Bill pounds Diamond all over her couch before jizzing all over her hot body. ...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 - Diamond Jackson Gets Plastered With Cum

Diamond Jackson - Brown Bunnies

18th October - GETTING PLASTERED WITH CUM!!!! That's just the way Diamond Jackson likes it. That's right, this hot MILF returns to Brown Bunnies. From the start you know that Diamond is in charge. She takes gets right to jamming that dick down her throat. THIS GIRL DON'T PLAY SON!!! After some of oral, our boy Sean slid deep in that pink hole, hitting the back that pussy until exploding on her face, giving her a nice frosty glaze of cum. ENJOY MOTHAFUCKAS!!! ...read more
Big Tits In Sports

Diamond Jackson and Bill Bailey in Seduced by a cougar

Diamond Jackson - Seduced By A Cougar

6th November - Diamond is relaxing in her yard when she catches Bill picking fruit from her trees. He's been stealing from her for weeks now, and she's ready to teach him a lesson. When he tells her he's leaving, she threatens to call the cops on him. She orders Bill to take off his shirt . then to stand on the table . then to take off his pants . then to put his penis in her mouth. His punishment? He has to fuck her until he comes on her tongue. If that's what you get for picking some forbidden fruit, gimme summa THAT!!! ...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 Kris Slater in Tonight's Girlfriend

Diamond Jackson - Tonight's Girlfriend

20th August - 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. ...read more
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