Videos Tagged with ifuckedtheboss.com

Big-titted stripper Victoria gets huge dick

Thu 23 Apr 2026 02:48:44 +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.

Put it in the bushy hole!

Sat 12 Oct 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.

Afternoon delight

Mon 23 Sep 2024 03:49:28 +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.

Work her booty

Sat 21 Sep 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.

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

Sun 30 Jun 2024 03:29:01 +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.

Work that boss's butt!

Sat 22 Jun 2024 10:38:14 +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.

Chanel makes the gardener's dick grow

Tue 11 Jun 2024 10:30:43 +0200

I'm a lady in the boardroom, a slut in the bedroom, said 50-year-old Chanel Carrera. "Isn't that what men want?" Here, Chanel is a slut in her backyard garden and in the bedroom, which is definitely what we want. We don't know how Chanel makes things grow in the garden, but she definitely can make our cocks grow in the bedroom or anywhere else. Chanel was born in New York City, lives in Boston, Massachusetts and has our favorite marital status: divorced. That's code for horny as fucking hell. She lists one of her hobbies as "going to swingers' parties in which I'm the centerpiece." But she says this is the most exciting thing she's ever done. "Being 50 and still being able to turn men on and have them want to look at my pictures is the most exciting thing I could have ever imagined," she said. "Do you see how wet my pussy is? That's because the whole time, I couldn't stop thinking about all you horny guys at home looking at me while you have your cocks in your hands, stroking them and getting harder." She must be clairvoyant.

Titty bosses with pierced cunts love hard cocks

Thu 30 May 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.

Jewel's internal affairs

Sun 12 May 2024 10:33:32 +0200

There are good bosses and there are bad bosses. Jewel is one of the good ones. After saddling her new employee with a tough assignment that has him stressed out and working late, she has him back to her office for what she calls "a little de-stressing session." And what does that involve? Hey, it's Jewel! You know exactly what that involves. Tit-sucking. Cock-sucking. Deep fucking on Jewel's desk and office couch. But if a man really needs to de-stress-if he really needs to take a load off, so to speak-he needs to shoot his load deep in a GILF's pussy. And that pussy belongs to Jewel. Yep, it's an internal cum shot and creampie for Jewel, and by the time the dude pulls his cock out of her 60something pussy, her cunt lips are sticky and the cum is pouring down her ass cheeks. "I love creampies," Jewel said. "It's so natural. It's the way most people fuck, right?" Most people, yes, but not most porn people, which is what makes this so special. Jewel, 61 and married, does something that even a lot of experienced porn sluts won't do. But don't call Jewel a slut. She's a lady. A lady who deserves your cum.

Luna's workmate bonus

Fri 10 May 2024 08:30:30 +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.

Bethany gets a creampie from her boss

Thu 09 May 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!

Who's the boss? Dallas is the boss!

Thu 09 May 2024 06:12:40 +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."