Videos Tagged with ifuckedtheboss.com

Big-titted stripper Victoria gets big cock

Wed 14 Jan 2026 13:52:52 +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.

Jewel's internal affairs

Wed 15 Jan 2025 10:28:51 +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.

Who's the butt-ravaged boss?

Mon 13 Jan 2025 06:58:03 +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.

Who's the boss? Dallas is the boss!

Thu 02 Jan 2025 13:06:59 +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."

Luna's workmate bonus

Mon 30 Dec 2024 02:19:39 +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.

Chanel makes the gardener's shaft grow

Tue 24 Dec 2024 22:23:58 +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.

Work her butt

Tue 10 Dec 2024 06:26:10 +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.

Afternoon delight

Tue 26 Nov 2024 22:15:11 +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.

Put it in the bushy hole!

Sun 24 Nov 2024 15:43:10 +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.

How to succeed in business by fucking your boss

Thu 14 Nov 2024 22:17:20 +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.

Boss giving you a hard time? Fuck her!

Fri 08 Nov 2024 17:57:45 +0200

Natasha, a 45-year-old divorcee from Southern California, is the customer service rep who services one of her employees. Natasha knows how to look professional, but she also knows how to work her pussy. We can imagine her as the ball-busting boss, but then it's easy to imagine her as the ball-sucking boss, too. Clearly, Natasha came to work dressed to fuck. And fortunately, someone took her up on it. When this video starts, Natasha is being a bitchy boss, and that might be a turn-off to some but not to one of her workers, who's sitting there fantasizing about her. Her bitchiness breaks him out of his fantasy, and he's thinking, "Fuck, I'm in trouble." She says she's noticed him watching her. He confesses. What else is he supposed to do? Damned if you do, damned if you don't, right? Natasha gets off on getting it doggie-style, rubbing a vibrator against her clit, fucking a long-haired guy with a cane, eating pussy, tattoos and men in uniform. She likes wearing short shorts, tight-fitting jeans and fuck-me pumps in public. "When guys think about their dream girl, they think about a tall, blonde fuck doll," Natasha said. "That's me!"

He's late, but he's on-time for the boss's cunt

Tue 05 Nov 2024 15:35:08 +0200

When this video opens, you might say to yourself, "What the fuck? What are those two chicks, who obviously aren't 40-something, doing in my video?" But then 44-year-old Gina shows up, and everything starts to click. She's wearing a tight leopard-skin mini, a skin-hugging top and fuck-me pumps. Turns out she's the boss of this eating and drinking establishment, and she's pissed off. Levi, the hired help, is late for his shift again.

"You have to respect me and do whatever I tell you to do," Gina tells Levi.

"I think you look hot," he says. "Is that respectful?"

"Maybe," Gina says, and then she loosens up in a hurry. He fingers her hairy pussy and feeds his cock into her mouth. At the end, he shoots his load into her wide-open mouth.

Gina is not the typical mature woman who suddenly discovers sex when she turns 40. A star of well over 200 fuck films since she was in her 20s, Gina says, "I'm easy. I just want hot, steamy sex."

Gina isn't into any fetishes. She doesn't want you to tell her that she's a bad girl, and she has no desire to fuck you with a strap-on.

"I love to suck cock and I love getting fucked hard and long," she said. "I've been horny for as long as I can remember, and I don't think that will ever change. It's just me."