https://www.transhero.com/tags/lesbian-boss/ Mon 27 Apr 2026 07:11:39 +0200 https://www.transhero.com/videos/250855/girlsway-i-really-need-this-job-boss-i-ll-do-anything-christie-stevens-and-evelyn-claire/
In order to keep her cushy job, Evelyn's willing to do whatever it takes -- including seducing Christie to show her exactly WHY her past employers thought so highly of her. ]]> Sat 07 Mar 2026 23:02:50 +0200 https://www.transhero.com/videos/250855/girlsway-i-really-need-this-job-boss-i-ll-do-anything-christie-stevens-and-evelyn-claire/ https://www.transhero.com/videos/209222/my-lesbian-assistant-is-enthusiastic-about-her-job-laney-grey-and-jessica-ryan/
When Laney shows up uninvited to her house on a Saturday night to deliver a file, dressed rather sexily, Jessica finally confronts Laney about her odd behavior. It just seems like that Laney is trying to get closer to her than any boss and employee should be! That's when Laney finally caves and admits that she DOES want to get close to Jessica in a more intimate way. She's been orchestrating things so that they can spend more time together... She just admires Jessica so much and can't help herself around her! Jessica is shocked to hear all this but is afraid of losing a good assistant to such... distractions. She then realizes that there's only one way to get rid of these distractions once and for all! ]]> Wed 04 Mar 2026 04:10:06 +0200 https://www.transhero.com/videos/209222/my-lesbian-assistant-is-enthusiastic-about-her-job-laney-grey-and-jessica-ryan/ https://www.transhero.com/videos/187006/hot-boss-caught-watching-porn-in-working-hours/
Casey isn't impressed with Chanel's work ethics and wants her job. Chanel laughs it off... until Casey reveals that she knows that Chanel uses the company computer... personal use. ]]> Sun 22 Feb 2026 16:06:05 +0200 https://www.transhero.com/videos/187006/hot-boss-caught-watching-porn-in-working-hours/ https://www.transhero.com/videos/121235/assistant-seeks-revenge-on-boss-in-steamy-office-sex-ryan-keely-ryan-reid/
Ryan Reid hates her job as an assistant for blonde executive Ryan Keely, so she takes every opportunity to sneak into Ms. Keely's office when she's not there, helping herself to her lipstick and touching herself in her chair. Ms. Keely suspects her assistant is up to something and orders the brunette around, catching her stealing money from her purse! She tells Ryan to lick her pussy, and the hot brunette does, then decides it's time to get even as she sits on her boss's face. The women lick and finger each other and even 69, then scissor around a vibrator. Has this naughty assistant learned her lesson? ]]> Sat 21 Feb 2026 02:06:32 +0200 https://www.transhero.com/videos/121235/assistant-seeks-revenge-on-boss-in-steamy-office-sex-ryan-keely-ryan-reid/ https://www.transhero.com/videos/204911/karlee-grey-and-jade-nile-fighting-for-the-position-feat-sovereign-syre/
Sovereign tells the girls that she wants to figure out which of them has what it takes to be her new personal assistant, so Karlee and Jade will have to compete for the position. ]]> Fri 20 Feb 2026 12:02:41 +0200 https://www.transhero.com/videos/204911/karlee-grey-and-jade-nile-fighting-for-the-position-feat-sovereign-syre/ https://www.transhero.com/videos/335891/bitchy-boss-enjoys-dominating-a-lesbian-employee-madison-stuart-and-sahara-knite/
Sahara can be a bitchy boss when she needs to be. Today it's Madison's turn to see just how much of a boss bitch Sahara really is.....and she is pretty excited about it! ]]> Sun 08 Feb 2026 18:42:55 +0200 https://www.transhero.com/videos/335891/bitchy-boss-enjoys-dominating-a-lesbian-employee-madison-stuart-and-sahara-knite/ https://www.transhero.com/videos/286923/girlsway-business-woman-has-the-best-assistant-all-over-the-world-laney-grey-and-jessica-ryan/
Jessica Ryan is a busy businesswoman who relies on her loyal assistant, Laney Grey, to help keep things running smoothly. ]]> Mon 02 Feb 2026 13:29:22 +0200 https://www.transhero.com/videos/286923/girlsway-business-woman-has-the-best-assistant-all-over-the-world-laney-grey-and-jessica-ryan/ https://www.transhero.com/videos/164032/pure-taboo-egomaniac-boss-nina-elle-have-sex-at-job-interview-with-a-trickster-girl-emma-hix/
Hot blonde woman, Emma Hix seduces egomaniac boss, Nina Elle for mysterious purposes. She turns on the voice recorder on her phone... ]]> Thu 29 Jan 2026 06:57:45 +0200 https://www.transhero.com/videos/164032/pure-taboo-egomaniac-boss-nina-elle-have-sex-at-job-interview-with-a-trickster-girl-emma-hix/ https://www.transhero.com/videos/221418/girlfriends-films-lesbian-spencer-bradley-really-wants-this-job-and-megan-maiden-s-pussy/
Spencer Bradley enters the company's PR manager, Megan Maiden's room. After couple questions it's clear for Spencer that Megan wants to get to know her in every possible way. ]]> Sat 17 Jan 2026 16:44:38 +0200 https://www.transhero.com/videos/221418/girlfriends-films-lesbian-spencer-bradley-really-wants-this-job-and-megan-maiden-s-pussy/ https://www.transhero.com/videos/111025/horny-boss-amber-michaels-seduces-teen-assistant/
]]> Wed 24 Dec 2025 12:09:57 +0200 https://www.transhero.com/videos/111025/horny-boss-amber-michaels-seduces-teen-assistant/ https://www.transhero.com/videos/70248/girlfriends-films-lesbian-milf-syren-de-mer-seducing-the-intern-percy-sires/
Syren De Mer has a nice and diligent assistant, Percy Sires. But Syren has ulterior motives with her. I agree with the milf, Percy is pretty hot indeed! ]]> Sat 20 Dec 2025 15:13:53 +0200 https://www.transhero.com/videos/70248/girlfriends-films-lesbian-milf-syren-de-mer-seducing-the-intern-percy-sires/ https://www.transhero.com/videos/41116/girlsway-look-how-she-perform-under-pressure-by-lesbian-boss-sovereign-syre-skylar-snow/
Sovereign wants to make sure that Skylar can perform under pressure, so she decides to test this by fingering Skylar as Skylar has to explain various marketing strategies. ]]> Mon 08 Dec 2025 06:53:55 +0200 https://www.transhero.com/videos/41116/girlsway-look-how-she-perform-under-pressure-by-lesbian-boss-sovereign-syre-skylar-snow/