https://www.transhero.com/sites/i-fucked-the-boss/ Wed 15 Apr 2026 03:11:56 +0200 https://www.transhero.com/videos/318966/boss-giving-you-a-hard-time-fuck-her/
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!" ]]> Sun 15 Mar 2026 02:37:06 +0200 https://www.transhero.com/videos/318966/boss-giving-you-a-hard-time-fuck-her/ https://www.transhero.com/videos/382655/bombshell-dallas-matthews-bangs-with-her-29-yo-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." ]]> Sun 08 Mar 2026 03:48:40 +0200 https://www.transhero.com/videos/382655/bombshell-dallas-matthews-bangs-with-her-29-yo-boss/ https://www.transhero.com/videos/345985/huge-titted-mature-elektra-gets-her-both-holes-drilled/
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. ]]> Sat 07 Mar 2026 03:42:55 +0200 https://www.transhero.com/videos/345985/huge-titted-mature-elektra-gets-her-both-holes-drilled/ https://www.transhero.com/videos/217888/the-lawn-boys-dp-kelly-leigh/
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!" ]]> Mon 02 Mar 2026 08:18:58 +0200 https://www.transhero.com/videos/217888/the-lawn-boys-dp-kelly-leigh/ https://www.transhero.com/videos/379989/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. ]]> Tue 24 Feb 2026 07:48:46 +0200 https://www.transhero.com/videos/379989/chanel-makes-the-gardener-s-cock-grow/ https://www.transhero.com/videos/182730/horny-boss-gets-licked-and-fucked-in-the-office/
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. ]]> Mon 09 Feb 2026 21:57:44 +0200 https://www.transhero.com/videos/182730/horny-boss-gets-licked-and-fucked-in-the-office/ https://www.transhero.com/videos/156033/severance-pay-layla-s-pussy/
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. ]]> Sat 07 Feb 2026 09:02:02 +0200 https://www.transhero.com/videos/156033/severance-pay-layla-s-pussy/ https://www.transhero.com/videos/350554/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. ]]> Mon 02 Feb 2026 03:16:40 +0200 https://www.transhero.com/videos/350554/big-titted-stripper-victoria-gets-huge-cock/ https://www.transhero.com/videos/386598/mature-office-worker-bethany-james-fucks-hung-boss/
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." ]]> Sun 01 Feb 2026 14:02:40 +0200 https://www.transhero.com/videos/386598/mature-office-worker-bethany-james-fucks-hung-boss/ https://www.transhero.com/videos/313283/alesia-pleasure-assfucked-hardly-bcs-her-husband-can-t-do-it/
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. ]]> Tue 27 Jan 2026 02:09:28 +0200 https://www.transhero.com/videos/313283/alesia-pleasure-assfucked-hardly-bcs-her-husband-can-t-do-it/ https://www.transhero.com/videos/138348/65-yo-busty-boss-fucks-hard-with-her-big-cocked-employee/
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." ]]> Sun 25 Jan 2026 00:11:42 +0200 https://www.transhero.com/videos/138348/65-yo-busty-boss-fucks-hard-with-her-big-cocked-employee/ https://www.transhero.com/videos/315545/amazing-ebony-diamond-showing-her-riding-skills-on-white-dick/
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!" ]]> Sat 24 Jan 2026 00:46:41 +0200 https://www.transhero.com/videos/315545/amazing-ebony-diamond-showing-her-riding-skills-on-white-dick/