My MILF Boss Pornstar Pictures

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We have 75 Milf Pictures for My MILF Boss.
Displaying Pictures 1 - 40.
My MILF Boss Alura Jenson 2
Alura Jenson is that kind of mouthy, domineering boss you've always dreamed about. She knows how to take charge like no other. She's interviewing very shy beta-male Chad Diamond and makes fun of him for his stuttering and clothes before spreading herself on her desk and seducing him with her luscious body. Spreading her ...

My MILF Boss Sarah Vandella
Ever since she hired Jake Jace at her company, Sarah Vandella has always wanted to feel his young cock plowing her sugar walls. Today, she gets her chance. She barges into his office and pushes him against the file cabinets with her overtly sexual advances. Subtlety was never Sarah's strong suit. Jake loses all inhibitions ...

My MILF Boss Aaliyah Love
Being the boss can get a bit boring but Aaliyah Love sure knows how to spice things up! She's interviewing potential new hire, Jake Jace and she's wondering if he can adequately FILL the new position. Jake timidly takes off his pants and shows his cock to her. Liking what she sees, Aaliyah hops on her desk, spreads her ...

My MILF Boss McKenzie Lee
Sexy, sultry MILF boss, McKenzie loves being her own boss. Always having eager male employees to bang doesn't hurt either! She's getting a back rub from Jessy Jones and his hands seep down past her blouse and fondle her giant tits. She sighs in relief as he keeps massaging her breasts. Turning around, she unzips his pants ...

My MILF Boss Silvia Saige
Jake Jace is poking around in his boss's office when he finds her sexy lingerie stashed away in her secret sex cabinet. Just then, the boss herself, Silvia Saige shows up and catches him in the act of jerking off! With a coy grin, she grabs his erect cock and strokes him right into her warm mouth and sucks him off. After ...

My MILF Boss Sarah Jessie
Sexy boss, Sarah Jessie just heard about one of her employees jerking off during his lunch break and she's gonna find out who! Calling in Jessy James into her office, she immediately grills him about his inappropriate masturbating and demands to see his cock! Caught red-handed, Jessy sheepishly pulls out his rather large ...

My MILF Boss Veronica Avluv
Queen bee, Veronica Avluv is exhausted after a day of fielding interviews from new applicants. She just wants a serious dick ride before she goes home. Then, steps in Mr. Pete with his big ol' peen! After bossing him around, Veronica puts him right to work by spreading her luscious silk-clad legs and buries his face in ...

My MILF Boss Stevie Lix
Hot MILF boss, Stevie Lix always gets what she wants! After pleasuring herself in her personal, private office, Stevie sends for new hire, Jake Jace up for some hardcore fun. Impressed with his hot body, she grabs his hard dick and plops it in her mouth, massaging it against her cheeks. Then, she strips off all her clothes ...

My MILF Boss Sindy Lange
Sindy Lange just hired a Russian stud as her assistant and she's putting him to work right away...starting with his big cock! She sits on his desk with her legs spread as Markus tries to take a sales call. He's finding it hard to stick to the script with Sindy's silken foot rubbing his crotch. Slamming the phone down, ...

My MILF Boss Dayton Rains
After a long day of interviewing boring new hires, sexy MILF boss,Dayton Rains finally gets a hot candidate in Mr. Pete! Tossing aside his resume, she walks right up to him and asks him straight up if he has a big dick! Before Mr. Pete can respond, she's already fishing out his cock and about to give him a blowjob! Once ...

My MILF Boss Syren De Mer
Serial masturbator, Damon Dice can't stop playing with his penis at work and his smoking-hot MILF boss, Syren De Mer knows it! Bursting through his office, she catches him red-handed and he has no other choice than to satisfy this cougar's every dirty desire. He lays back submissively as she whips out his fat dick and ...

My MILF Boss Robin Pachino
Screaming hot hardcore featuring a mature hottie

My MILF Boss Nina Elle
Jesse Jones has no idea why his scorching-hot boss, Nina Elle called him to her office. His jaw drops when she announces that she has to let him go due to budget cuts. Jesse offers to do ANYTHING to keep his job. Nina's eyes twinkle as she looks at his crotch. Sliding his trousers off with ease, she sucks his big stiffy ...

My MILF Boss Heidi Mayne
A lingerie clad blonde bimbo getting her pussy plowed

My MILF Boss Alisandra Monroe
A buxom and curvy MILF boss gets put through her paces

My MILF Boss Claudia Valentine 2
Poor employee, Brad Knight just broke the news to his bitchy hot MILF boss, Claudia Valentine that her own husband has been running up company bills for escort services! Mad as a hornet, Claudia immediately tries to get even by seducing Brad into banging the crap outta her moist pussy. After motor-boating him, she gives ...

My MILF Boss Mercedes Carrera
Mercedes Carrera has a big ol' sexy ass and she knows it too! After discovering that Romeo has been dicking around at work, specifically searching for big bootie porn, Mercedes decides to give him what he wants! After flagrantly exposing her naughty juicy butt to him, she lets him fondle her curvy, stacked body and yanks ...

My MILF Boss Maci Maguire
After completing his TPS reports for his demanding but super sexy MILF boss, Maci Maguire, she crawls across her conference table and grabs his hand and shoves it up her black miniskirt. She's not even wearing any panties! Talon sucks on her huge tits, giving extra lovin' to her sweet nipples while finger-banging her shaved ...

My MILF Boss Ela Darling
Ela Darling never met a house she couldn't sell. Her client, Scott Lyons is getting cold feet when it comes to signing on the dotted line so Ela uncrosses her legs and has already made up her mind to fuck this hapless fella. That should sweeten the deal! Scott lets her keep rubbing his cock from under his trousers, eventually ...

My MILF Boss Addie Juniper
Bitchy hot MILF boss, Addie Juniper is about to fire Kevin Wang but decides to exploit him instead for her own sexual gratification! She lays on top of her desk and stretches out her lovely legs towards Kevin, indicating she wants a foot rub! He starts massaging her feet without hesitation. Then, ever so slowly, Addie ...

My MILF Boss Alyssa Lynn
Talon is busting his ass at work when the boss's spoiled daughter comes dashing into his office barking orders at him - the first of which is to lick out her cunt! Talon wipes his mouth and gets on his knees instantly and gives this bitch the tongue-twirling adventure of her life! Some real afternoon delight happening ...

My MILF Boss Jessica Ryan
Overworked MILF boss, Jessica Ryan is so busy with her job that she doesn't even have any time for dick! While working after hours, she's started by the appearance of Jerry, who's stopped by to paint her office. Jessica's pulse immediately jumps up several notches as she stares at his big arms and his big package. Seconds ...

My MILF Boss Samantha Bentley
Romeo is clowning around in his office when in steps in his hot-ass boss, Samantha Bentley! After reprimanding him for his shitty work ethic, Romeo has had enough of her bitchy nagging and flings her on the couch and unbuttons her blouse. Shocked by his forwardness, Samantha whips Romeo's cock out and swallows it whole ...

My MILF Boss Kali Kavalli
Tax season is here and nerdy accountant, Scott Lyons is tasked with doing his hot boss's tax returns. Kali Kavalli and her hot-ass fucking body is too much of a distraction for Scott, so she pulls him close and plants his face right on her pussy lips. Instantly, he starts furiously finger-banging and licking that cunt. ...

My MILF Boss Cherry Ferretti
MILF bosses get extra bitchy when they don't get the deep dicking they deserve and crave! CHerry Ferretti is on the warpath and chews out her lazy worker, Sonny Nash for not finishing up an important report but Sonny calms her down instantly by fondling one of her juicy tits! Cherry is shocked by his actions but can feel ...

My MILF Boss Nicky Ferrari
There's nothing quite as sexy as a stunning Spanish MILF! Nicky Ferrari fumbles through her English but with big tits like those, nothing gets lost in translation! Tony starts flirting with Nicky Ferrari, touching her boobs and unzipping his fly and whipping out his cock for Nicky to suck off. He fingerbangs that shaved ...

My MILF Boss Avona Dominica
After finding his boss's missing reports, Romeo Price gets rewarded with a blowjob from his hot MILF boss, Avona Dominica! Only this blond cougar has a special gift - she can fuckin' squirt like there's no tomorrow! She unzips Romeo's fly and gorges on his cock, lapping up his nuts and polishing off his cock-head before ...

My MILF Boss Sabrina Sanchez
Desperate hire, Dick Delaware will do anything to land a job, including fucking his busty MILF boss! After Sabrina Sanchez yanks down her top and shows off her huge tits, Dick gets the message and unsheathes his fat weiner for her to snack on. After drilling her face, he parts her long longs and laps up that mature cunt ...

My MILF Boss Raquel Devine 2
Dick Delaware arrives at Raquel Devine's offices for a job interview. Quickly impressing her and turning her own with his gravely, deep voice, Raquel throws off her business ensemble and gets on her knees. Dick quickly unzips his trousers and Raquel marvels at the thickness of his cock. She sucks him off right and good ...

My MILF Boss Nikita Von James
Heaven-sent blond goddess, Nikita Von James may look super hot on the inside but she's really a bossy bitch! After chewing out her employee, Billy Glide, Nikita uses her power position and easily seduces him into some hardcore fucking! Nikita needs to use both hands to jerk Billy off while tickling his cock-head with her ...

My MILF Boss Abbey Brooks
Goofy grease monkey, Ralph Long has just finished putting the final touches on Abbey Brooks' hot Ferrari, but she still needs a little work done under her hood. As Ralph is thumbing through some papers, Abbey opens up her low-cut top and unleashes her giant, mouth-watering tits. Ralph immediately latches on and sucks on ...

My MILF Boss Layla Rivera
Wondering why her construction crew is spending all of her money, Layla Rivera confronts her foreman, Scott Lyons about her budget. At her house, as he's going over the details, Layla is suddenly drawn to Scott's cock, stroking it above his pants. He takes his hard hat off as Layla lets loose her hot tits from the confines ...

My MILF Boss Alura Jenson
Smoking-hot realtor, Alura Jenson is trying to flip a property but the repairs aren't nearly done! She makes a split second decision with her sub-contractor to seduce and fuck him so he'll get the house ready in time. Alura takes an aggressive approach and climbs on Christian's lap as he undoes her purple lace bra and ...

My MILF Boss Leena Sky
Smoking-hot cougar, Leena Sky catches one of her office peons, Sonny Hicks photocopying his dick! As punishment, she grabs him by the cock and walks him into her personal office to reprimand. Sitting on her desk, Leena spreads her legs and watches as Sonny dips his head in between her thighs and licks her twat and fingers ...

My MILF Boss Ashley Fires
Joey Brass has been trying to impress his boss for months so he can score the promotion that's looming. He knows he's got the skills, but she doesn't seem to notice him. He wants to be sure he's got this in the bag, so he goes to see her one afternoon in her office to make his case. Ashley Fires just found out her husband ...

My MILF Boss Alana Evans
Stacked blond Alana Evans looks completely sensational in her slutty office outfit. She leans over the desk, facing stud Romeo Price, who gets an amazing view of her impressive cleavage. Her skirt rides up at the back, showing off her ass then Alana sits in front of the stud on the desk, showing off her panties, which ...

My MILF Boss Jocalyn Stone
Daniel Hunter is doing his job as the gardener for wealthy wife Jocelyn Stone when she invites him into the house. At first he is worried because he thinks that she is going to sack him - but all she wants to do is suck his dick! Jocelyn has got a voluptuous figure, with a great pair of full breasts and a big ass that ...

My MILF Boss Dallas Diamondz
Dallas Diamondz is having trouble finding a reason to keep Levi on as an employee. She knows he's almost always in late, and never seems to get his work done on time, so she calls him into her office. She remembers the reason she hired him right away, he's easy on the eyes and knows how to flirt just the right way to get ...

My MILF Boss Shay Fox
Young stud Bruce Venture is drinking his coffee out in the parking lot, slacking off, when his busty MILF boss Shay Fox rolls past. She gives him an arch look and orders him to report to her office. Bruce was expecting to get a good drilling down, but instead it's him who does the drilling! Slutty Shay spreads her legs ...

My MILF Boss Amanda Blow
Often it's the strictest and most dominant businesswomen who turn out to be the wildest and most submissive in the bedroom! Stud Billy Glide is aggressively seduced by all natural blond MILF Amanda Blow, who strips right in front of the stud and kneels on the sofa, sticking out her ass and pussy for a tonguing. Billy knows ...

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