Lesbian Boss Stories

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Lactating Breasts, Office Girl

by HeyAll on Sep 25, 2017
Lesbian Sex

The prominent tech CEO, Ms. Meyers, had cut her maternity leave short for an urgent business matter and extra help was required. That was how Abbey landed the job of executive assistant at the last minute, despite her relative inexperience at the highest levels of the corporate world. Abbey was nervous meeting the boss for the first time after having been h...

Letting Go Ch. 02

by ShoneyB on Sep 16, 2017
Lesbian Sex

Chapter 2: Toe Fucking at Lunch (This story continues directly after the events of Letting Go I) .................... She had to run to catch her bus. Her skirt was short and she was wearing no knickers, her knees were weak after the morning love games, her loins tenderized from the breakfast spanking, and, to make her vulnerability even worse, her heels...

The New Assistant

by PandoraSharp on Jul 14, 2020
Lesbian Sex

*Author's Note: For those who have read my first submission, this one involves the same characters; however, it would take place at least a year prior to that story. Also, this one is a lot more story driven than "Mark's Surprise". Again, comments and constructive criticism are greatly appreciated. Hope you enjoy. *** I return to work on Monday with drea...

Exotic Seduction

by Bakeboss on Sep 16, 2017
Lesbian Sex

As she stood waiting for the door to open, Britney realized how nervous she was. She knew she was in awe of her boss, I mean who wouldn't be. In her mid forties and running a big company yet she could easily be mistaken for a thirty year old. Britney had no idea what her Mrs. Carlson wanted her to do today, she just hoped she didn't screw it up. The door op...

A Valentine's Date Ch. 01

by jsmangis on Feb 6, 2018
Lesbian Sex

This is my entry into the Valentine's Day story contest. It is a tale that takes place in the high fashion industry, and how love sometimes finds people in places and ways they never expected. * Sally Hemmings sat looking at the Valentine card that had been left on her desk before she arrived at work that morning. It was very beautiful and ornate, and smel...

Archer's Lane Case 01 Ch. 06

by KatPissinger on Dec 10, 2018
Lesbian Sex

The next day, she found Kathleen on the upper deck, where she was trying to enjoy the last rays of sunshine that shone down on the Atlantic from a cloudless sky. Her boss was wearing a tight bathing suit and a gigantic sun hat, and the bright sun made her pale skin seem even paler. "Ah, there you are," Kathleen greeted her happily, when she noticed Eliza. "C...

The Internship

by hr6183 on Sep 19, 2017
Lesbian Sex

I was out of school for the summer. Being a 20 year old college student, I always needed money to pay for school. Fortunately, daddy was able to find a job for me at this real estate investment company. He was friends with one of the people who worked there. Apparently, I was going to be an administrative assistant for a woman named Jan. I didn't know much a...

Iris' New PA

by MELD9003 on Sep 13, 2017
Lesbian Sex

Hi readers, This is a follow up story to Kate, Fiona & Iris; a story I wrote a few months ago. (Incest/Taboo category) Hope you enjoy it. MELD. ******************************* Hearing the knock at the door, Iris adjusted her glasses and sat up straight in her chair. "Come in," she said in a friendly tone. The door opened and in stepped Jane, one of...

Customer Service Manager

by HeyAll on Jul 16, 2019
Lesbian Sex

Usually the first day of a new job feels like a whirlwind, but for newly promoted Olivia Wong, the first day was a hurricane. She had taken a flight across the country with her famously strict boss and spent an uneventful night with her at a hotel. In the morning, after breakfast, they drove a rental car to their destination. Upper management at the corpo...

Red Lipstick Innocence

by HeyAll on Sep 25, 2017
Lesbian Sex

Faye was a virgin. In college of all places! It wasn't that she was a prude, and she certainly was no hermit hiding away in her dorm room. In fact, far from it. Faye was a typical, everyday, outgoing college student. She was relatively popular from all the clubs and activities she participated in and was active in community events too. She remained a virgi...