When your boss is a hot MILF with big tits like Maya Devine, it’s pretty tough to turn down the invitation to fuck the shit out of her. Our boy McLovin whips out his massive caramel colored rod for this cock-fiend whore to blow. Maya has got some serious cock-sucking skills to go along with her thirst for the dick. Her huge, but slightly lopsided titties make for some great cock-slapping and her shaved clam is just calling for a thick dick to get stuffed up in there. Maya gets fucked like a good whore before McLovin dumps a fresh load of cum all over her face and boobs.

Big titty brunette MILF Stephanie Wylde is a cock hungry cougar who preys on her employees. She won’t let them get away with any kind of insubordination – and she won’t let them get out of her office without pleasuring her tight pussy, either! As her employee Chris Stokes sits on the chair in front of her executive desk, she walks around, staring him boldly in the eye and flaunting her breasts as she sits down on his lap. Soon she is having her pussy licked by the younger stud, who then lays her out on the couch and plugs her shaved mature pussy. She cups her breasts to catch every drop of the creamy cum as it spurts on her face.

Blond cougar Angela Attison is despised by most of her employees, despite her model quality good looks and enormous fake boobs. She’s a real bitch of a boss, consistently criticizing her employees and making life generally difficult. When she walks in to the office and sees stud John Strong making a mess of the filing cabinet, she’s furious! The only thing that will make her feel better is if John squats between her thighs and licks her shaved pussy. John gets Angela’s cunt nice and wet, so she requires him to finish the job; she leads him into her private chambers, where she sucks his dick and then spreads her legs for a good fucking.

TJ is spending his day off at his boss' house fixing the garbage disposal hoping to get a little extra cash — what he gets instead is the complete fuck of a lifetime from his MILF boss.

Nick East isn't the kind of guy who takes a job working for someone else. He normally runs his own show, but when Allesandra needed some temporary help he agreed to give her a hand so long as it was done on his terms. He gets to fuck her as hard as he can every morning before his work day starts and her big tits serve as his own personal cum canvas where she deposits all the cream for her morning coffee. The day she stops trading pussy for office help Nick is done with her… but for now this MILF is paying benefits better than any 401K!

In the United States women can’t be the hungry whores they wish they were once they become bosses because they have to worry about sexual harassment suits. If you go over the border and get a foreign fuck like Heidi Maine to hire you instead then you can bet she will be kneeling between your legs with your bone slamming the back of her throat long before you make it to your first official lunch break. Heidi is a MILF Boss and she knows how valuable time at work is so don’t hold back and drag this out… go ahead and white-wash her face as fast as you can. She has plenty of other people… err, uhmmm, “things”… to do today!

Kendra Secrets is not your typical employer. For one thing, she only hires men… and for another, all the men she hires are young guys in good shape with a big bulge in their jeans. If you fit that description you should definitely send her your resume and ask for an interview because whether she hires you full time or part time you can be sure you will be spending most of your time balls deep in this babe’s box! Her perfectly shaved hairless pussy doesn’t taste a day over twenty-two… and when you get all the way up her ass you will swear her holes are ten years young than she is!

When Andrew applied for this job he had no idea what position he was going to be placed in. He figured he might be a clerk or a stock worker but he never thought he would be offered female cowgirl, doggy-style or full frontal facial as starting positions by a boss as hot as Lena Ramone! It just goes to show you, if you never ask for it you’ll never get it. Just because your boss is a MILF that doesn’t mean she would refuse the chance to have you pump her out and splatter her face with man sauce!

Robin is a thirty-something sweetheart who spent her teen years getting attention from all the popular boys. As she aged she thought she would have a hard time keeping studs interested until she met Andrew Andretti. He is the kind of guy who knows that hot veteran whores have years of experience satisfying men and know things that the teen crowd would take years to train. Why teach some shy chick how to suck you off when you can get a girl who has already been broken-in?!

Ava Devine is the perfect MILF Boss not only because of her huge tits and sexy dimples but because she really knows how to get the whole job done. From sucking cock in the jawbreaker position with the head of your dick pressed against the inside of her cheek to tearing up and drizzling her eye makeup all over her pretty face as she tries to hold back a flood of saliva with your rod ramming her throat. Don’t be shy about asking her for a raise because when it comes to penis nobody can give yours a raise better than Ava!