https://www.fapbox.com/tags/lady-boss/ Thu 04 Jun 2026 09:12:52 +0200 https://www.fapbox.com/videos/33821284/auntjudys-chubby-bbw-boss-lady-megan-milly-hires-you-as-her-personal-assistant-pov/
In this sexy POV Experience, Chubby BBW MILF Boss Lady Megan Milly hires you as her new personal assistant, then gets right to putting you to work. She strips down to her sexy stockings, shows off her big ass, then jacks you off and sucks your cock until you shoot your hot load! Another gem from AuntJudy's Unrivaled Collection of Mature Women and MILFs. ]]> Wed 16 Apr 2025 05:38:41 +0200 https://www.fapbox.com/videos/33821284/auntjudys-chubby-bbw-boss-lady-megan-milly-hires-you-as-her-personal-assistant-pov/ https://www.fapbox.com/videos/33718516/pee-swallowing-girls-strict-training-of-her-staff/
Good staff is hard to find. It is time to educate her staff when water is not served quickly enough and at the wrong temperature. Facesitting seems to be the way to go. Pressing her big butt cheeks on her face makes it impossible to breathe. Testing how long the maid can hold her breath makes the lady boss happy. Now, it is time to show her the correct natural water temperature. She pees into her mouth, and the maid gets a whole load of her golden shower! The truth is sometimes hard to swallow, so even this has to be trained by swallowing the boss' pee repeatedly. ]]> Sat 22 Mar 2025 17:37:45 +0200 https://www.fapbox.com/videos/33718516/pee-swallowing-girls-strict-training-of-her-staff/ https://www.fapbox.com/videos/33717584/builder-fucks-his-big-ass-boss-and-gives-him-a-huge-load-of-cum-brandon-cruz-devil-khloee-the-busty-boss-who-hired-me-to-bui/
The busty boss who hired me to build her deck, acts so horny when she sees me in my uniform, she is a big ass BBW who sucks my dick deliciously, I fuck that pussy without caring if the neighbors see us. She loves my BBC in her pink pussy ]]> Fri 28 Feb 2025 22:18:38 +0200 https://www.fapbox.com/videos/33717584/builder-fucks-his-big-ass-boss-and-gives-him-a-huge-load-of-cum-brandon-cruz-devil-khloee-the-busty-boss-who-hired-me-to-bui/ https://www.fapbox.com/videos/33742613/entertain-us-or-suffer/
LADY BOSS APRIL PAISLEY AND EPIPHANY JONES ARE HAVING A SOPHISTICATED LADY'S NIGHT IN USING PORN SLAVE GEORGE AS A CHARCUTERIE BOARD, WHEN ALL OF A SUDDEN THEY WANNA PLAY A GAME WITH HIM! PAIN FOR PLEASURE IS THE WAY THIS GAME IS PLAYED AND THEY HAVE SOME TRICKS UP THEIR SLEEVES ]]> Tue 18 Feb 2025 21:45:10 +0200 https://www.fapbox.com/videos/33742613/entertain-us-or-suffer/ https://www.fapbox.com/videos/33726641/messing-with-the-maid/
LADY BOSS APRIL PAISLEY IS PACKING FOR A FUN TRIP AWAY WITH HER SLAVE, BUT WHILST THE MAID KELLY STAR MAKES SURE EVERYTHING IS SPOTLESS BEFORE THEY LEAVE SLAVE GEORGE CANT HELP HIMSELF BUT PERV ON THE PRETTY MAID! WHILST THINGS START TO GET A LITTLE HOT AND STEAMY BETWEEN THEM IN THE LIVING ROOM GEORGE ACCIDENTALLY KNOCKS OVER A GLASS OF WATER ALERTING MISTRESS AND SHE CATCHES THEM KISSING. OH NO THIS ISN'T LOOKING GOOD FOR GEORGE AS WITHOUT ASKING MISTRESS FIRST TO DO SUCH PLEASURABLE THING MUST LEAD TO PUNISHMENT, AND LADY APRIL IS GOING TO USE THE PRETTY MAID TO TORMENT AND ALSO PUNISH HIM WITH HER! ]]> Mon 03 Feb 2025 04:27:30 +0200 https://www.fapbox.com/videos/33726641/messing-with-the-maid/ https://www.fapbox.com/videos/33722460/nicole-dupapillon-the-boss-interviews-and-plays-with-her-latest-recruit/
Nicole is a very sexy boss and she takes a great interest in her employees particularly if they are handsome and well hung. She meets with Steven her latest recruit to see what he is made of - literally. Lots of sucking, wet blowjobs, squirting pussy licking and fucking in this clip as Steven puts his big Black Cock to good use. Gotta keep the boss happy. ]]> Tue 31 Dec 2024 20:20:09 +0200 https://www.fapbox.com/videos/33722460/nicole-dupapillon-the-boss-interviews-and-plays-with-her-latest-recruit/ https://www.fapbox.com/videos/33748064/auntjudysxxx-busty-boss-milf-maisie-lewis-fucks-her-employee-at-the-office/
Busty Boss MILF Maisie Lewis knows it's not appropriate workplace behavior, but she pulls out her Big Natural MILF Tits, strips down to her sexy stockings, then sucks her employee's cock before letting him fuck her wet MILF pussy and finish up by shooting his load in her mouth! A little taste of Hardcore Home Cookin' from AuntJudy's XXX. ]]> Thu 26 Dec 2024 07:20:47 +0200 https://www.fapbox.com/videos/33748064/auntjudysxxx-busty-boss-milf-maisie-lewis-fucks-her-employee-at-the-office/ https://www.fapbox.com/videos/33811910/boss-lady-admonishes-bryson-with-a-handjob-and-epic-cumshot/
]]> Mon 15 Jul 2024 08:43:04 +0200 https://www.fapbox.com/videos/33811910/boss-lady-admonishes-bryson-with-a-handjob-and-epic-cumshot/ https://www.fapbox.com/videos/33785545/glamorous-lady-boss-offers-her-big-butt-for-fucking/
She is a woman devoted to her work and she is ready to do everything so her company keeps developing. One day she noticed one of her employees started to stare at her booty too much, so she decided to give him what he wanted so badly and even let him cum right in her asshole so he isn't distracted anymore. ]]> Mon 08 Jul 2024 22:19:45 +0200 https://www.fapbox.com/videos/33785545/glamorous-lady-boss-offers-her-big-butt-for-fucking/ https://www.fapbox.com/videos/33776460/auntjudysxxx-your-busty-boss-maisie-lets-you-fuck-her-pov/
Your Busty Boss Lady Maisie gives you a choice between getting fired and FUCKING her wet MILF PUSSY, and you choose the latter! Maisie pulls out her BIG NATURAL TITS, then SUCKS YOUR COCK and lets you FUCK her tight wet pussy until you shoot your load. A little taste of our famously intimate "POV Experience" Collection from AuntJudy's XXX. ]]> Tue 02 Jul 2024 17:25:26 +0200 https://www.fapbox.com/videos/33776460/auntjudysxxx-your-busty-boss-maisie-lets-you-fuck-her-pov/ https://www.fapbox.com/videos/33764478/sexy-assistant-assisting-a-poor-tiny-dick-during-his-job-interview/
The lady boss invited this tiny cock guy to an interview when it was revealed his dick was simply too small for the job! Her assistant came over to help him with his job application, but his small dick was not up to standard ]]> Sat 01 Jun 2024 10:28:24 +0200 https://www.fapbox.com/videos/33764478/sexy-assistant-assisting-a-poor-tiny-dick-during-his-job-interview/ https://www.fapbox.com/videos/33730037/boss-ladies-cast-new-male-model-with-a-monster-cock/
Tim has always wanted to become a Playboy model. Finally he got his casting, and he was so lucky the photographers were beautiful lades who were very surprised and obsessed to see his monster cock. ]]> Sat 06 Apr 2024 04:56:19 +0200 https://www.fapbox.com/videos/33730037/boss-ladies-cast-new-male-model-with-a-monster-cock/