Lick A Boss

Bobbi Dylan hasn't been meeting her sales quotas, so she is called into her boss' office to explain. Not willing to accept Bobbi's excuses, Diamond teaches her employee that the best way to get ahead is to fuck your boss.

The Return Of Simony Diamond, a Milf Addicted to Anal

Private present your favorite superstar of yesteryear, remember Simony Diamond! In Milf Secretaries, we show this now cougar still has what it takes to be the best in the business. Her big tits still look as good as they once were and this slut can't wait to get herself a taste of cock, she drops to her knees and gives her man a sensual blowjob. Then, she lets him enter her tight shaven pussy taking him hard and fast before opening up that round Milf ass for a dose of hardcore anal! Once her needs have been met, this babe opens wide to take a sticky facial.

Lying Doggystyle

Diamond is no stranger to her sexual side but she is definitely curious about a few things…like her neighbor. When she asks to walk his precious dog one afternoon she gets more than she begs for!

French Service

Aleska responds to a call asking for her French maid services, she answers and heads to an upscale downtown flat. Telling her to clean a few rooms, and that he'll return in an hour, the owner of the flat heads out. Aleska undresses to get into her maid uniform, but then uncovers a few props the owner left behind... soon she can't contain her sexual energy, and plays with the toys herself. To her surprise, the owner comes back too soon, and discovers her mid-play. He has a few extra toys to share with her as well, and soon the two start a new game. Things get pretty dirty, and it's hard too see how Aleska can clean it all up in time, especially with the mess her client leaves on her face.

Game, Set, Match Pussy

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!

Yhivi Does It

When exotic, young Yhivi shows up for a woodworking demonstration, seven guys are already waiting -- and they can't keep their eyes off the luscious booty squeezed into her cut-off jeans. Soon pretty Yhivi's working on a different kind of wood, as she's surrounded by huge, hard cocks! The guys fuck her face, making Yhivi drool sloppily as she struggles to service them all. Finally, the pale slut kneels as the men shoot load after load into her open mouth.

Diamond Jackson and Preston Parker in My Wife's Hot Friend

Preston Parker and his wife are starting to question their marriage. His wife asks her friend, Diamond Jackson, to spice things up for them before their marriage is doomed.

Slam It Harder

Fetish queen Mya Diamond has her filthy desires answered in this double stuffing, eye watering scene.

Diamond Is Your Boss

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!

Sexy Role Playing Game

Christen Courtney feels bad for her stepbrother, Chris Diamond, who wants to play his fantasy role-playing game but doesn't have any friends. Christen decides to be nice and humors Chris, only she decides to make the game a lot sexier considering she's got a dirty imagination and is always horny as fuck! Watch as this hot nympho takes the role-playing game to a whole new level—she's on a quest to find a big dick for her wet pussy to suck and fuck!

Big Butt Wedding Day

It's Simony's wedding day, but she can't stop thinking about the best man. Her husband-to-be just doesn't make her pussy wet like Danny does. Can she really go through life without knowing what his cock tastes like? Or will she give into temptation on the big day?

Moms Twist Of Date

Shy Crystal Rae has invited over Jessy Jones to her house to play some board games. Only, her horny stepmother, Diamond Jackson, can't help but spy on them. When Ms. Jackson gets a whiff of sexual tension between these young lovers, she decides to take over their game and show them how to really play--by getting down and dirty, that is!

Stepmoms Sweet Glory Hole

Diamond is a busy housewife with lots of errands to run, but between grocery shopping and dropping her stepson off at soccer practice she always makes sure to find time for herself. She loves to unwind with a little glory hole action, but today she's in for a big surprise. That mysterious cock she's swallowing is her stepson's! This could be an awkward situation, but Peter's forbidden cock makes Diamond even more wet and eager to fuck.

Rocco's Psycho Teens 9

After voluptuous gardener Kittina's employer calls her ass fat, the gorgeous but distraught brunette seeks confirmation from friendly Chris Diamond, who assures the shapely doll that her round rump is perfect. Kittina thanks him by giving Chris' huge boner a sensuous tongue bath; soon he's pounding her shaved pussy with abandon. Finally, boss Lutro and Chris' hot girlfriend, Cindy Loarn, show up to make it a swinging four-way party with anal fucking and double penetration!

Simony Diamond Knows How to Drain Cum With Her Mouth

Long legged Simony Diamond struts her stuff in Private's classic hit series 'Cum on My Face 6'; but as soon as she catches a glimpse of hard cock, she can't resist. This deep throat expert wraps her luscious lips around his stiff member and sucks him sweetly, using her hands to make him cum. After she has finished sucking his fat cock with a real sloppy blowjob, she opens wide to take a slow motion cumshot all inside her mouth!