Boss Lady Stories

105,242 results
Orientation
Length
Source
Infinite Scroll

New Virgin Escort's First Date

by KissedMany on Sep 12, 2017
First Time

Arrangements Are Made for the New Escorts First Date Fran, the co-owner of Midnight Magic Escorts, was calling Clare, her newly hired virgin escort. The young music student's New York City escort licence had been approved and Fran had staged a bidding war among her wealthy clients as to who would take the newbie's cherry. She was not surprised that somebody...

Taming the Boss Pt. 01

by romantictales on Aug 24, 2020
Fetish

Hi everyone! This is my first story, and English is not my native language either. So any suggestions and help in editing will be highly appreciated. All characters are imaginary and aged above 24. ________ In terms of material pursuits, John Davies was an extremely successful person. At 32, he was already the CEO of a million dollar business employing mo...

Jack to Jacqui

by MarkThyme on Sep 16, 2017
Transsexuals & Crossdressers

Redundancy and divorce are two of the most catastrophic things that can occur to anyone. It is not entirely unusual for one to follow the other, but the hurt and feeling of devastating rejection are doubled when it happens. Jack Larbury went through just that. After 20 years, his job was gone as the company he'd joined as a 16-year old went through a proces...

First Day of a New Job

by vanessa65 on Sep 25, 2017
Illustrated

Having just opened the garage door, Vanessa wondered if there was anything she had forgotten. She was nervous about today. It was the first day of a new job as an assistant with a consulting firm. At the interview she had met the man who would be her boss, should she be the successful applicant. She remembered being quite impressed with him. Her new empl...

Carol's Hotel Experience

by eeric on Sep 12, 2017
Interracial Love

If you have the time you can e-mail me at the address in my profile and tell me what you thought. * * * * * My name is Carol and I'm married to David since 10 years back. We have quite a nice life together. David has a good job at a medium sized company who handles public relations for other businesses. He creates slogans and that kind of things. David i...

A Lovely Day for a Walk

by Rikki on Aug 19, 2017
Exhibitionist & Voyeur

It was a lovely day for a walk in the woods, thought Jane Allen as she stopped her Ford outside the entrance to the park. Locking the car she put her small backpack on her shoulders and set off along one of the walking tracks. Dressed in grey slacks and a powder blue twin set that looked good with her shoulder length blond hair, Jane certainly didn't look li...

The Boss

by amorprohibido on Sep 17, 2017
BDSM

The Boss.... Amanda made her way into her Boss's office to translate, he barely looked up to acknowledge her just began jabbering, and she in turn began to write. Pompous Jerk, Amanda thought to herself but she needed this job and her mouth had gotten her in trouble before. For some reason everything in her rebelled against this guy. But for Amanda that h...

The Fall Guy Ch. 05

by The Wanderer on Sep 16, 2017
Non-Erotic

I thank my LadyCibelle and Techsan for their patience, proof reading, editing skills and of course encouragement they always give me. As I've been known to fiddle with stories, after they've seen it. I take full responsibility for the content and any cock-ups in this story. While I'm at it, I think from now on I'm going to thank all my friends out there, w...

What a Day - Pam Ch. 01

by up-for-anything on Sep 16, 2017
Romance

What a day. My first day at my new job and before the day could even come close to ending; I had my cock buried in some lady's pussy. I think her name was Pam. She was a forty something with a short spiky haircut that was to covey that she was young and hip. She had a French manicure and what appeared to be, and felt for that matter, an excellent boob job. T...

The Librarians Apprentice Ch. 02

by MrRusty2000 on Aug 30, 2017
Group Sex

Part 1 Jimmy had been servicing the needs and desires of Miss Pringle, the library manager, for nearly a month. Even after all this time and hundreds of ejaculations into her various orifices, Miss Pringle was still never familiar with him but always very stern and bossy. After he'd done her most perverted demands she would revert back to form within second...