Videos Tagged with ifuckedtheboss.com

Work her butt

Sun 15 Mar 2026 20:34:21 +0200

Here's Alesia pulling the oldest cougar trick in the book: picking up a contractor and getting him to her house under the guise of wanting him to do some repair work when in reality...

"I need work done on myself, not the house," Alesia tells Sergio. "I want you to fuck me in every hole I have."

Now, sure, times are tough, and Sergio could use the money, but he'll worry about the rent later. For now, he has been personally invited to fuck a horny, sexy MILF in her mouth, pussy and asshole, and that's not an offer that comes along every day. So, fuck work, and fuck Alesia!

Alesia is 45 years old and from Pennsylvania. She told us that the first time she had sex was "in a car with a guy I had been with for a month. He went anal without telling me!"

Well, this time, we gave her plenty of notice, and Alesia dressed for the occasion in a sexy dress and pantyhose that the stud rips open to get at her pussy and plump ass. Now, that might sound primitive, but, hey, she's the one who picked up the guy under false pretenses, and, as you're about to see, Alesia isn't complaining about her ruined hose. She's getting everything she wants.

Who's the boss? Dallas is the boss!

Sun 15 Mar 2026 04:11:46 +0200

Dallas Matthews, who's 57 years old, is the boss. Tarzan, who's 29 years old, is her employee. He's brought her the reports she needed, but she tells him, "You're not up to par with our expectations." He needs more experience. "You need to become more aggressive with your clients," she says. And she's going to show him how. By sucking and fucking his cock? Hey, every boss has her own style. Dallas' style includes blonde hair and big tits and a great pussy. "I'm very aggressive when it comes to sex," Dallas said, "but I like a man to be a man. It doesn't matter how tall they are. Sometimes short guys can really strut their stuff. And it doesn't matter how tall you are in bed. It's my legs that are long. If you're spooning, you're just together." Dallas was born and raised in Washington before she moved to Canada and then back to Washington. She's divorced. "I've had quite an interesting life," she said, "I've done quite a bit, everything from construction and house-building to excavation and ranching. Consulting, agriculture, initiating bio-control for the mushroom industry." Dallas likes things that are mushroom-shaped. She works in finance. She was sent our way by 60Plus MILF Madison Milstar. Her boyfriend approves. "This was totally his idea," she said. "Part of me is doing this for him. I'll wink at him. 'That was for you!' I'm being a naughty girl."

The deal isn't sealed, but Rita's holes are stuffed

Sat 14 Mar 2026 02:10:22 +0200

Rita Daniels is the boss, and she calls her star salesmen into her office. She's wearing a short skirt, and her big tits are straining her blouse, which is distracting enough. The guys think they're in trouble. Sales are down. She tells them they're going to have to do a little tag-teaming.

"We're good at tag-teaming," they say.

She asks them what she can do to boost their morale. Will it take a bonus? A free trip?

Rita's tits, pussy and asshole, perhaps?

Yeah, that'll do it. You see, the boys have been talking about fucking Rita's 62-year-old ass. And Rita has been thinking about getting her 62-year-old ass fucked by her star salesmen. She wants them to work as a team? They can do that. They can jam her mouth with their cocks. One can fuck her pussy while the other feeds her his cock. They can take turns fucking her asshole. Because teamwork is all about sharing.

Motivated? Damn, right they're motivated. Motivated to tag-team Rita's ass. But sales? That's another story.

Sindy Swank means business

Thu 12 Mar 2026 13:49:53 +0200

Now this is how you run a business meeting! You're the boss, but Sindy Swank thinks she knows what's best for your company, even though it's been in your family for 54 years. You tell her, "We're going to do things the traditional way," but she counters with, "These days, women have the power." Now you've got her exactly where you want her because she's gonna prove it. And how is she gonna prove it? You know how! This 54-year-old divorcee from Virginia bends over and says, "Pull my skirt off," then demands, "Lick my ass, now!" She thinks she's teaching you a lesson in business, but this is exactly what your cock wanted all the time. "Put four fingers in there," she demands. "Put four fingers in my pussy! Fuck me!" So you slide four fingers into her pussy and when she says, "Keep fucking me! Don't stop fucking me!" the truth is you have no intention of stopping. Because soon, it's gonna be your turn. So she gets down on her knees and sucks your cock and balls. By now, she thinks you're coming around to her way of running a company, but in fact, this is what you had in mind all along. She really stuffs her face into your balls, and then you fuck her mouth, pumping, pumping. When she sucks your balls, your rod brushes against her cheek, and if you don't get into her pussy soon, your balls are going to explode. "Best fucking meeting we've ever had in this company," you say as you fuck her on the table, and this time, you mean it. "Oh, yes, you're the best boss I've ever had!" Sindy says as your balls slap against her asshole. Don't you know it. "I'm proud of my cock-sucking skills," Sindy said. "I practice a lot." She has sex four or five times a week and is very assertive. One time, she hosted a swingers party and only men showed up. "It turned into my first gang bang," Sindy said. "But not my last."

Afternoon delight

Thu 12 Mar 2026 08:20:26 +0200

Lin Boyde, a 65-year-old divorcee from Arizona, returns to discipline a younger guy with her mouth and pussy and winds up with a big load of cum all over her face. Lin is a well-sexed woman, and like most well-sexed women her age, she knows exactly what she's doing...exactly how to handle a man who's nearly 40 years her junior. Ironically, in this scene, Lin is a boss who disciplines her employee, but in real life, Lin says she prefers "take-charge men who make romantic gestures."

A cum facial...is that romantic?

"Sex doesn't always have to be romantic," Lin said. "I'm a swinger, and my guy and I had sex in front of a crowd of people in a club. That wasn't romantic. That was hot!"

There's something very horny and sexy and hungry about Lin. It's as if she can never get enough. She doesn't merely suck and fuck cock. She devours it.

"With the right man, I could have sex several times a day," she said.

And for Lin, the right man is easy to find. He has a hard-on.

Severance pay: Layla's muff

Tue 03 Mar 2026 22:43:22 +0200

In real life, Layla Redd, a 41-year-old divorcee from Maryland, is an educator. An assistant principal in a high school. At least she used to be one. She lost her job. Here, she's a boss at a big company. Unfortunately, times are tough, and she has to fire some of her employees. Unfortunately for Juan, he's one of the ones to go. Fortunately for Juan, he's going to get a goodbye fuck before he leaves. No wonder the unemployment rate is so high! Men are getting fired on purpose so they can fuck their sexy female bosses on the way out! Okay, that's probably not the reason. But if Layla were your boss, it could be the reason. "I'm a swinger," Layla said. "I love having sex with other men and having my boyfriend watch. I dress conservatively because I had to at my old job, so a lot of people would never guess at the real me. They'd never think that I would pose nude and have sex on-camera." Layla has perfect B-cup tits that she covers in those conservative clothes. Not surprisingly, she always wears a bra. That's what keeps her tits so beautiful. Her hobbies are traveling, reading and "being lazy," but she says she likes men who aren't afraid to take chances. In this video, Juan isn't afraid to take a chance. Layla obviously likes that about him. That and his cock. And if you're asking us which came first, her attraction to his cock or her attraction to his risk-taking, well, we just haven't thought it through that deeply. And neither should you.

Luna's workmate bonus

Tue 03 Mar 2026 12:56:19 +0200

Luna Azul, 60, pulls the old, "Lady boss catches the young employee at the copy machine and decides to fuck him because he's making copies of pictures of her pussy," trick. You never heard of that trick, did you? Well, you might have heard about a hot female boss, and you might have heard about male employees checking her out behind her back and talking about how much they'd like to fuck her. Well, that's what's been going on in Luna's office, but what the boys don't realize is that Luna wants to fuck them, too. Some of the best parts of this scene come early on, such as when Luna sits on the desk in the middle of the copy room and tells her employee to eat her pussy right then and there, and if they get caught, so what? She's the boss. Another good part is when the employee realizes Luna is wearing pantyhose and the only way to get to her pussy is to tear a hole in them. Which he does, and Luna doesn't mind that she's going to have a hole in her pantyhose for the rest of the day, and who knows? Maybe she'll fuck another employee. Of course, there's that messy cunt that Luna will have to deal with, too, because, yes, the boss takes a creampie in this one. That's what's called an employee bonus.

Who's the butt-ravaged boss?

Thu 26 Feb 2026 14:24:12 +0200

Lauren Taylor is a 56-year-old mother of two. She has a son, and if you think it's easy growing up as the son of a hot mom, think again. "He had to beat his friends up, and then he got kicked out of the group," Lauren recalled. "A couple of them were very blatant. I had a pool, and I'd catch a group of boys watching me swim and lay out. Or they'd come into my bedroom. You know, they'd walk towards that part of the house and just wander in. It was pretty obvious." Lauren's son's friends were walking around with lumps in their pants "and telling me when they were gonna turn 18. It was pretty funny. And I'd say, 'No, you're still my son's friends, so that's not going to happen.'" Lauren's son's friends never got any. But they're over 18 now, which means they can legally view 50PlusMILFs.com. And maybe they're sitting at their computers right now, watching the hot mom from their childhood getting ass-fucked on-camera. In this scene, Lauren is a boss who catches her employee, Tony, using a remote-controlled camera to shoot upskirt videos under her desk. But she doesn't fire him. She has him fuck her mouth, pussy and ass right there in the office. So, to recap: Lauren's son's friends got nothing. Her employees get it all.

Work that boss's butt!

Tue 24 Feb 2026 14:55:26 +0200

Jamie is a hard-driving, bitchy boss, and she's making a lot of demands. This poor guy has a lot of work to do and not much time to do it, but he's distracted by Jamie. You see, she's sitting in the office in a very unprofessional manner. Her legs are crossed, and this poor shlub can see the top of her stockings and her thighs, and Jamie's talking about work, and all he wants her to do is work his cock. "Are you paying attention to me?" Jamie asks. "Have you written down anything that I said?" She takes his notepad to see what he's been writing, and she's shocked. "Wow, 'I wanna pound that ass?' That's what you wrote?" Jamie says, aghast. "'Do you deep throat? I want your ass?' That's what you've been taking notes about the whole time?" Now emboldened, the guy says, "I also wrote, 'I want you to suck my cock right now.'" This kind of stuff can get a guy fired...if his boss is somebody other than Jamie. "You know what I think?" Jamie tells him. "I think you're a very dirty boy. I like dirty boys." Jamie found out about us from a friend she knows online. She has a long list of fetishes and is a very kinky woman. No one really knows how wild her private sex life is. "I like sex multiple times a day," Jamie said. "I can be submissive or bossy depending on my partner of the moment. I'm kind of an exhibitionist. I like men or women getting sexually aroused by watching me. In a video, I can get thousands of people hot." She definitely does that.

Big-titted stripper Victoria gets big cock

Tue 24 Feb 2026 13:53:39 +0200

This real-life 53-year-old Texas stripper tips a huge-cocked hired hand by offering up her big jugs and shaved, pierced pussy. This busty old broad deserves a big cock, which is why we gave her one. "I was hoping to have the real porn stud experience," Victoria said. "I loved when he fucked my tits and came all over my face." Hey, Victoria, isn't 53 a little old to be a stripper? "Don't ask me," she said. "Ask the guys who cum in their pants when I give them a lapdance." We'll take her word for it.

The buttfucked boss is Rita Daniels

Tue 24 Feb 2026 02:25:08 +0200

Rita Daniels, one of our favorite GILFs ever, is the busty boss who catches her young employee, 24-year-old Rocky, talking about her on the phone. He thinks he can say whatever he wants because he's speaking Spanish and he doesn't think Rita understands. But she does, especially when he tells whoever he's talking to that his boss has big tits and he wants to fuck her. Put it this way: No matter what language you're speaking, if you say, "My boss has big tits and I want to fuck her," and the boss you're referring to is Rita Daniels, she'll understand. Rita is fluent in multiple languages of fuck talk. Anyway, before long, lucky Rocky is playing with Rita's big tits and eating her hairy pussy (it's usually shaved; not this time). Then she's sucking his dick, one of the things she does best (the horny-as-hell look on her face when she's downing dick is one of the best things about Rita) and sitting on his cock and then taking his cock in her tight asshole. And then he's cumming on her face. Nobody-and we mean nobody-looks better than Rita with cum dripping down her face. Rita is a mother and a grandmother. If her kids only knew! Actually, they do.

Make Americans fuck woman politicians' assholes again

Sun 15 Feb 2026 18:20:44 +0200

Supposedly, people are tired of politicians who keep doing things the same old way and expect anything to change. But 50-year-old Elektra Lamour is not one of those politicians. She's an outsider, a woman who wants to do things a new way, her way. So when the guy who's applying for the job as her campaign manager shows up at her office, Elektra tells him that she wants to have a more hands-on, one-on-one approach to working with people and getting votes. She wants to attract the blue-collar workers. Or did she say boob-collar workers? Either way, the guy gets the hint, and before long, he's having some one-on-one time with Elektra's big tits, hairy pussy and tight asshole. He fucks her in the ass right there on the office desk and then he cums on her hairy pussy, making a real mess of it. Elektra is married. She's a mother and grandmother. She's been fucking on-camera for nearly 20 years, and she's been an escort, too. She's fucked such stars as Nina Hartley and Ron Jeremy. She loves watching porn almost as much as she loves making it. And she doesn't have to worry about making porn great again because it already is great. At least at 50PlusMILFs.com.