https://www.transhero.com/tags/tranny-boss/ Tue 14 Apr 2026 21:14:42 +0200 https://www.transhero.com/videos/37618/butler-serves-shemale-boss-in-every-way/
Busty shemale boss gets a shoulder massage from her butler and she wonders if there could be more.A kiss seals the deal and the big tits tgirl deepthroats his big cock.The trans is sucked and gives a double handjob before shes anal barebacked ]]> Tue 01 Apr 2025 08:02:47 +0200 https://www.transhero.com/videos/37618/butler-serves-shemale-boss-in-every-way/ https://www.transhero.com/videos/37098/busty-milf-intern-has-an-anal-threesome-with-big-ass-tranny-boss/
Big boobs MILF intern Summer Hart gets fingered by her big dick tranny boss Izzy wilde and while she was getting dicked down the big dick maintenance worker Kasey Kei found them and whipped her boner out to rail them both in a hardcore anal threesome! ]]> Fri 07 Mar 2025 11:27:52 +0200 https://www.transhero.com/videos/37098/busty-milf-intern-has-an-anal-threesome-with-big-ass-tranny-boss/ https://www.transhero.com/videos/14408/tranny-boss-korra-del-rio/
Korra's a hot TS Babe and Lance is desperate to keep his job and have a taste of the gorgeous brunette. ]]> Thu 20 Oct 2022 10:27:28 +0200 https://www.transhero.com/videos/14408/tranny-boss-korra-del-rio/ https://www.transhero.com/videos/13146/ginger-tranny-boss-seduced-her-worker/
Racy redhead Aspen Brooks is a boss, a sexy busy boss. Kirk Cumming, his handsome and submissive husband, pays her a visit at her workplace. While Aspen rocks her meeting, dirty Kirk sneaks under the table and sucks her nice dick. Kirk's ass is hungry for a good pounding. Aspen fiercely aborts the meeting and rims her man until he asks for more. Dominant Aspen handles the dirty talking even better than she speaks business. Kirk moans and sighs as she bangs him and gives him orders. She demands a good reverse cowgirl and Kirk is quick to obey. Aspen lazes and watches as her boy does all the hard work, like all CEO perverts like to do. Kirk cums all over Aspen's big boobs and she shoots back at his chiselled chest like a pro, right before kicking him out to get back to work. A lesson in time management.Release Date ]]> Thu 14 Jul 2022 08:59:15 +0200 https://www.transhero.com/videos/13146/ginger-tranny-boss-seduced-her-worker/ https://www.transhero.com/videos/16686/introverted-secretary-getting-screwed-by-tranny-boss-kenna-james-natalie-mars/
Kenna is taken to new heights of pleasure as Natalie sinks between her legs and eats out her pussy. She's all too happy to suck her boss' cock, wanting Natalie to feel just as blissed out as she does. When Natalie finally bends her over the desk and slips her cock into her pussy, Kenna is satisfied, knowing she's once again done her job well. ]]> Sat 09 Jul 2022 09:43:50 +0200 https://www.transhero.com/videos/16686/introverted-secretary-getting-screwed-by-tranny-boss-kenna-james-natalie-mars/ https://www.transhero.com/videos/14266/tranny-boss-gagging-on-workmate-s-prick/
Administrative assistant Chad Diamond has had enough of being sexually harassed by TS boss Lena Kelly. ]]> Sat 02 Jul 2022 10:03:07 +0200 https://www.transhero.com/videos/14266/tranny-boss-gagging-on-workmate-s-prick/ https://www.transhero.com/videos/14348/danni-daniels-plays-with-eva-lin-s-butthole/
Asian t-girl Eva Lin let her tranny boss playing with her slippery holes ]]> Wed 22 Jun 2022 10:17:50 +0200 https://www.transhero.com/videos/14348/danni-daniels-plays-with-eva-lin-s-butthole/ https://www.transhero.com/videos/11608/shemale-natalie-mars-hears-roumors-about-her-co-worker/
Colby Jansen is on phone, talks funny things with a friend when his trans girl boss, Natalie Mars walks in. She asks some questions about his inappropriate hookups with colleagues. ]]> Sat 14 May 2022 08:24:25 +0200 https://www.transhero.com/videos/11608/shemale-natalie-mars-hears-roumors-about-her-co-worker/ https://www.transhero.com/videos/11612/big-boobed-tranny-boss-ts-foxxy-banged-hard/
Draven Navarro is in a strange situation with his boss, TS Foxxy. She curious about her employee's falling numbers and he try to answer but keeps failing. The last chance to keep his job is... fuck the hell out of her. ]]> Thu 28 Apr 2022 08:24:48 +0200 https://www.transhero.com/videos/11612/big-boobed-tranny-boss-ts-foxxy-banged-hard/ https://www.transhero.com/videos/11490/older-tranny-boss-having-anal-sex-in-the-office-with-younger-workmate-nikki-vicious/
]]> Fri 18 Mar 2022 07:47:09 +0200 https://www.transhero.com/videos/11490/older-tranny-boss-having-anal-sex-in-the-office-with-younger-workmate-nikki-vicious/ https://www.transhero.com/videos/9474/trans-boss-natalie-eats-out-her-assistants-pussy-and-fucks-her/
Trans boss Natalie Mars had always an eye on petite teen assistant Kenna James When she tells her that she hungry innocent Kenna asks her what she wants to eat to which the shemale makes her spread her legs wide and eats out her pussy and fucks her hard ]]> Fri 24 Dec 2021 07:57:47 +0200 https://www.transhero.com/videos/9474/trans-boss-natalie-eats-out-her-assistants-pussy-and-fucks-her/ https://www.transhero.com/videos/8636/small-tits-trans-boss-natalie-mars-anal-fucked-by-employee/
Small tits trans boss Natalie Mars seduces her employee to have sex in the office and they kiss.The brunette tgirl gives him a blowjob and deepthroats his big cock.The guy asslicks her and then the shemale is anal fucked.Then she anal rides his dick ]]> Mon 29 Nov 2021 06:37:08 +0200 https://www.transhero.com/videos/8636/small-tits-trans-boss-natalie-mars-anal-fucked-by-employee/