https://www.thepornstar.com/tags/ifuckedtheboss-com/ Fri 17 Apr 2026 09:06:57 +0200 https://www.thepornstar.com/videos/427266/big-titted-stripper-victoria-gets-huge-cock/
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. ]]> Wed 04 Mar 2026 16:48:53 +0200 https://www.thepornstar.com/videos/427266/big-titted-stripper-victoria-gets-huge-cock/ https://www.thepornstar.com/videos/91217/jewel-s-internal-affairs/
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. ]]> Fri 27 Dec 2024 16:40:53 +0200 https://www.thepornstar.com/videos/91217/jewel-s-internal-affairs/ https://www.thepornstar.com/videos/81979/big-titted-bosses-with-pierced-cunts-love-hard-cocks/
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. ]]> Sat 21 Dec 2024 11:09:07 +0200 https://www.thepornstar.com/videos/81979/big-titted-bosses-with-pierced-cunts-love-hard-cocks/ https://www.thepornstar.com/videos/173706/luna-s-workmate-bonus/
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. ]]> Tue 03 Dec 2024 19:46:41 +0200 https://www.thepornstar.com/videos/173706/luna-s-workmate-bonus/ https://www.thepornstar.com/videos/101449/who-s-the-boss-dallas-is-the-boss/
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." ]]> Mon 02 Dec 2024 17:02:36 +0200 https://www.thepornstar.com/videos/101449/who-s-the-boss-dallas-is-the-boss/ https://www.thepornstar.com/videos/125361/the-buttfucked-boss-is-rita-daniels/
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. ]]> Wed 13 Nov 2024 05:50:23 +0200 https://www.thepornstar.com/videos/125361/the-buttfucked-boss-is-rita-daniels/ https://www.thepornstar.com/videos/178564/chanel-makes-the-gardener-s-cock-grow/
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. ]]> Thu 07 Nov 2024 21:04:55 +0200 https://www.thepornstar.com/videos/178564/chanel-makes-the-gardener-s-cock-grow/ https://www.thepornstar.com/videos/152792/work-that-boss-s-ass/
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. ]]> Sun 03 Nov 2024 14:31:36 +0200 https://www.thepornstar.com/videos/152792/work-that-boss-s-ass/ https://www.thepornstar.com/videos/73971/who-s-the-ass-fucked-boss/
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. ]]> Tue 08 Oct 2024 22:09:19 +0200 https://www.thepornstar.com/videos/73971/who-s-the-ass-fucked-boss/ https://www.thepornstar.com/videos/87691/sindy-swank-means-business/
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." ]]> Sat 05 Oct 2024 14:33:32 +0200 https://www.thepornstar.com/videos/87691/sindy-swank-means-business/ https://www.thepornstar.com/videos/63443/make-americans-fuck-female-politicians-assholes-again/
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. ]]> Fri 04 Oct 2024 19:26:22 +0200 https://www.thepornstar.com/videos/63443/make-americans-fuck-female-politicians-assholes-again/ https://www.thepornstar.com/videos/61891/bethany-gets-a-creampie-from-her-boss/
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! ]]> Fri 04 Oct 2024 19:11:49 +0200 https://www.thepornstar.com/videos/61891/bethany-gets-a-creampie-from-her-boss/