https://www.thepornstar.com/tags/male-boss/ Fri 10 Jul 2026 14:28:35 +0200 https://www.thepornstar.com/videos/450300/unwrapping-santa-s-big-package/
Scott Nails is getting ready for a hectic Christmas. You see, Scott secretly has two wives (younger socialite Violet Myers, and family-focused MILF Cherie Deville) and both are expecting him for the holidays. Today though, he's not fucking either of them. Scott goes to his office holiday party, where he bumps into his on-again off-again tryst, Lily Labeau. Lily knows cheating with a twice-married man is wrong... but Christmas is a time for merriment after all. ]]> Mon 06 Jul 2026 08:48:15 +0200 https://www.thepornstar.com/videos/450300/unwrapping-santa-s-big-package/ https://www.thepornstar.com/videos/474155/naughty-assistant-seduces-boss/
Isiah Maxwell’s naughty assistant, Kayley Gunner, just can’t help herself; she likes to cause drama, and this time her target is her hot boss she’s been dying to suck his dick. Why not in his livingroom? She stirs up resentment between him and his wife, Cali Carter. But, Cali isn’t taking this lying down; she wants to get her revenge of her own with the sexy Kayley and see how he likes being passed up! But it’s bad timing, Isiah comes home and catches the naughty women in action. ]]> Thu 18 Jun 2026 17:59:37 +0200 https://www.thepornstar.com/videos/474155/naughty-assistant-seduces-boss/ https://www.thepornstar.com/videos/473611/office-drama-tiamarie-bangs-girthmaster-s-huge-dick/
TiaMarie hears around the office that her new boss, Girthmaster, has a HUGE dick! Apparently, his third arm has caused a little drama in the workplace amongst the desperate women who’ve already banged him. Girthmaster just can’t keep it in his pants (it wouldn’t matter anyway; he can’t hide the dickprint in his pants). TiaMarie is skeptical and has to see this with her own eyes and feel with her own pussy what all the commotion is about. ]]> Thu 18 Jun 2026 01:24:56 +0200 https://www.thepornstar.com/videos/473611/office-drama-tiamarie-bangs-girthmaster-s-huge-dick/ https://www.thepornstar.com/videos/475203/bossy-babes-office-sex-motivation/
These hot bossy business babes have their own management style - and it works! Whether they’re looking to motivate unproductive employees or to help unwind from the daily office grind, a little bit of sex can go a long way to send everyone home with a smile on their faces. Check out this compilation featuring some of the sexiest bosses you’ve ever laid eyes on! ]]> Fri 22 May 2026 03:34:04 +0200 https://www.thepornstar.com/videos/475203/bossy-babes-office-sex-motivation/ https://www.thepornstar.com/videos/445702/cherie-deville-seduces-her-boss-for-a-sugar-daddy-lifestyle/
Cherie Deville doesn't want to work! Can you blame her? Who does? She's never wanted to, but she hasn't found that special guy that sugar daddy to make her the trophy wife she deserves... yet. Her boss, Mazee, might be the perfect mark, and if she can nab him, she's well on her way to her life of bliss. After office hours, it's time to turn on the charm. ]]> Sat 25 Apr 2026 11:15:08 +0200 https://www.thepornstar.com/videos/445702/cherie-deville-seduces-her-boss-for-a-sugar-daddy-lifestyle/ https://www.thepornstar.com/videos/414316/hot-weatherman-malik-fucks-boss-bunker-on-air-in-steamy-office-encounter/
Weatherman Malik Delgaty isn't happy when the air conditioning in the studio is busted and his boss, Bunker, just tells him to get to work. The sweaty hunk tries to record his segment, but he just can't take the record-breaking heat and pulls off his clothes! Bunker is mad Malik will get them fined for his on-air nudity, but Malik tells his boss "Suck my dick" ... and Bunker has been waiting for his chance. Malik fucks his boss from behind, then Bunker rides him on his desk chair. The boss bottom cums as the on-air talent fucks him on his desk, then takes a facial. ]]> Sat 31 Jan 2026 06:40:07 +0200 https://www.thepornstar.com/videos/414316/hot-weatherman-malik-fucks-boss-bunker-on-air-in-steamy-office-encounter/ https://www.thepornstar.com/videos/188202/busty-boss-raylene-serves-three-partners-in-her-office/
Raylene knows how to do business, especially the risky kinds of deals with male clients. Her definition of customer satisfaction is definitely something I can get behind. Or in front, if you know what I mean. ]]> Thu 11 Dec 2025 00:40:30 +0200 https://www.thepornstar.com/videos/188202/busty-boss-raylene-serves-three-partners-in-her-office/ https://www.thepornstar.com/videos/134943/kayden-s-pussy-goes-from-pink-to-red/
You have a luxury bitch like her teasing you, you better show her who's boss. You make her never forget who's the alpha male here, even if her pussy will never look the same again! ]]> Tue 02 Dec 2025 23:41:59 +0200 https://www.thepornstar.com/videos/134943/kayden-s-pussy-goes-from-pink-to-red/ https://www.thepornstar.com/videos/391737/best-of-isis-love/
Isis Love’s favorite things include sucking, fucking and wrapping her beautiful tits around hard cocks. Watch her show off her skills in this fantastic compilation of all Isis’s hottest moments. Get you goon on as she takes you down a perverted memory lane that you can stroke to! ]]> Thu 21 Aug 2025 03:44:50 +0200 https://www.thepornstar.com/videos/391737/best-of-isis-love/ https://www.thepornstar.com/videos/405372/clumsy-office-girls-ass-pumped-by-boss/
Steve Q is having trouble with his new office hire Canela Skin. Canela can't seem to focus, and when he takes a work call, she starts yakking away on her cellphone too! Steve asks for quiet, but his employee starts whistling. At the end of his rope, Steve turns around to find Canela using the scanner to take pictures of her big ass! Steve tells Canela she's fired, but she hikes up her skirt and begs to keep her job. At the sight of her delicious big booty, Steve decides to fuck his employee, first pulling down her panties and so he can eat her pussy and ass. Turned on, Steve takes out his hard cock and fucks Canela doggystyle, then takes off the rest of her clothes so he can enjoy her big, fake tits. Canela goes ass to mouth and gives her a boss a blowjob, then continues taking his dick until he blows his load on her face! ]]> Sun 17 Aug 2025 15:01:01 +0200 https://www.thepornstar.com/videos/405372/clumsy-office-girls-ass-pumped-by-boss/ https://www.thepornstar.com/videos/335368/reality-kings-big-naturals-boardroom-to-bedroom/
When Juliana Dreams and Ashlyn Peaks catch Mick Blue checking out during the meeting, they get his attention by drawing boobs on the presentation. Then the curvy babes take out their own huge tits and shock Mick by sucking them! The hotties suck his cock, then bring him into a bedroom where they make him watch as they rub their big boobs together and trib. Then it's time for Mick to join in as the business babes use his dick and get fucked! ]]> Fri 25 Jul 2025 00:44:02 +0200 https://www.thepornstar.com/videos/335368/reality-kings-big-naturals-boardroom-to-bedroom/ https://www.thepornstar.com/videos/91661/mick-blue-is-the-hoe-now/
Anikka Albright and Peta Jensen worked at an office with a dickhead boss. His name was Mick Blue and he was always groping up on his female employees and trying to fuck them. He was married, as were most of these women, but a man's dick has needs. He came into Anikka's office and was grabbing at her assistant Peta's tits. He made her really uncomfortable, but slightly horny. Anikka decided to find Mick's address, and the two of them went and surprised him at his house. They gave him a taste of his own medicine. Anikka and Peta sneaked into his house and ambushed him. They had their way with him, told him they owned him now and then left. Hot chicks in charge! ]]> Wed 23 Jul 2025 17:01:21 +0200 https://www.thepornstar.com/videos/91661/mick-blue-is-the-hoe-now/