Videos Tagged with ifuckedtheboss.com

Big-titted stripper Victoria gets big cock

Sun 16 Nov 2025 16:38:26 +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.

Work her butt

Wed 10 Apr 2024 03:56:31 +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 butt-ravaged boss?

Sat 06 Apr 2024 06:10:24 +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 early years 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.

Severance pay: Layla's muff

Wed 03 Apr 2024 04:54:39 +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.

Big Titted bosses with pierced cunts love hard cocks

Tue 02 Apr 2024 10:35:14 +0200

Thanks for picking me up and bringing me home, 54-year-old Deb says to Tony at the start of this scene. "Would you like to come in for a while?" She pushes him down onto the bed. You see, he's already "in." "Is this your bedroom?" he asks stupidly. "How do you like it?" she asks. "I love it," he says. "You're gonna love what we're gonna do with it. Or in it," she says. "I've had my eye on you for a long time," she says. He can't believe it, although what did he expect when this busty MILF accepted his offer of a ride? Did he think she thought he was being a Good Samaritan? Ah, we get it! She's his boss! And he's been flirting with the young girls in the office, perhaps not even thinking about fucking the boss, not knowing about her big, fake, DDD-cup tits and all those piercings on her pussy, not knowing she's horny for cock all the time. Miss Deb is a wife from Spokane, Washington. She's a MILF. A super-MILF, we say. "I wear low-cut, tight tops to show off my tits and short skirts to show off my legs," Miss Deb said. "When you have great legs, they should be shown off. I've noticed that men don't get that far, nor do they make eye contact." Nope. They just fuck her.

Sindy Swank means business

Tue 02 Apr 2024 08:18:59 +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."

How to succeed in business by fucking your boss

Sat 30 Mar 2024 03:53:02 +0200

Jarrod has a problem. He's been called into the office of his boss's wife, and even though she's a hot, tight-bodied MILF, and even though he's had his eyes on her ever since he started working at the company, he's in trouble.

"I hate to have these kinds of conversations, but I had to have you in here," Diamond says. "You're just not producing like you used to. I'm probably going to have to let you go."

But Jarrod is going to get one last chance to prove his worth, and it doesn't involve working. It involves eating Diamond's pussy and working it over with his cock. By the time this video is over (and Diamond has cum about 20 times), he has not only earned his place in the company, he's earned his place in Diamond's tight, juicy, pink cunt.

Diamond said it's important for you to grip your dick tight while you're jacking to this video "because then you'll know what it feels like to be in my mouth or pussy. I've been told I have the tightest pussy ever, and when I suck cock, I suck extra hard so you can feel the pressure around your dick. So, c'mon! Tighten that grip around your cock and work it hard. Stroke that big thing!"

We didn't need to be told, but thanks, Diamond.

The lawn boys Double penetration Kelly Leigh

Tue 26 Mar 2024 04:52:44 +0200

Kelly Leigh is a no-nonsense woman, so when she drops the drinks she brought out for her lawn care boys, she makes up for it by dropping to her knees and sucking their cocks. Would most women do this? No. But most women are not Kelly Leigh, who sucks dick like she's making love to it, enjoys being called "a fucking dirty whore" and takes cocks in her ass as casually as most women take it in their pussies. "I want your fucking cock in my ass!" she screams. There's DP action here, too, because Kelly is that kind of woman. A porn star, of course, but one who doesn't do it for the money. She does it for the sex. And if you need proof of that, just watch this video. "I love acting like a slut," Kelly said. "I love getting DP'd and sucking balls and doing all the things that women my age aren't supposed to be doing. Sucking two cocks, getting fucked in my ass, cum facials. I love it all, and the sleazier the better. I feel proud when I hear people say that I'm the sluttiest porn star they've ever seen, but in my mind, I can be even sluttier!" Kelly also said, "I laugh when I see those porn prima donnas who are worried about their hair getting messed up during a scene. It's sex! Your hair's supposed to be flying everywhere. Besides, it's gonna be full of cum soon, anyway. That's the whole idea!"

Put it in the bushy hole!

Sun 24 Mar 2024 03:56:09 +0200

It's another day at the office for 54-year-old Persia Monir. She's typing away, tits bulging above her tight blouse. She's called to the boss's office for some dictation, but when she gets there, the boss is playing golf, and not very well. So she gives him some pointers on putting. Turns out the boss isn't very good at putting, but he is good at putting his cock in Persia's mouth and pussy.

Make that hairy pussy. Very hairy pussy. The hairiest we've ever featured.

Anyway, back to Persia's golf lesson. The discussion comes around to Persia's tits, which she says get in the way when she golfs. Meanwhile, the boss is getting a hard-on, and Persia has noticed. She's noticed because his cock is pressing against her ass. Before long, his cock is pressing against her tonsils then it's pressing against the inside of her pussy.

Persia became a stripper when she was 34 years old (she told us she started stripping to support her golf habit; when Persia is playing regularly, she's a scratch golfer). She loves fucking on-camera.

"I think I look better now than I did when I was 18," she said. "I'm not going to be old and wrinkled. I refuse. What's the point? And I've always worked out, too. Swam, tried to eat right."

She fucks a lot, too. It keeps a woman feeling young.

The buttfucked boss is Rita Daniels

Fri 22 Mar 2024 06:13:08 +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 littles only knew! Actually, they do.

Make Americans fuck woman politicians' assholes again

Mon 18 Mar 2024 06:14:56 +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.

Bethany gets a creampie from her boss

Sun 17 Mar 2024 08:41:37 +0200

Bethany James, a 64-year-old divorcee, plays out a favorite fantasy: boss fucks his sexy employee. The boss is Mr. DeSergio. The sexy employee is, of course, Bethany. In real life, Bethany is a retired executive who worked for the State of Ohio. She was more the boss, less the employee, and she enjoyed more than her share of business trips during which she picked up strange men, took them back to her hotel room and fucked them. "I once picked up two fabulous men in a downtown hotel in Chicago and took them back to my room," she said. "We fucked all night, then we never saw each other again." Here, Bethany fucks her boss, filling her mouth with his cock then getting fucked in her pussy. She's wearing pantyhose, for those of you who are into that (we know a lot of you are), and at the end, Bethany gets a creampie in her pussy. "Nice and messy," Bethany said afterwards. "Just how I like it." A creampied 60plus...just how we like 'em!