Boss And Secretary Stories

359,767 results
Orientation
Length
Source
Infinite Scroll

Kinky Boss Pt. 01: A Finger In...

by freeman64 on Sep 13, 2017
Fetish

An insurance firm had advertised for a man to take care of 20 odd computers, running anti-virus stuff and programming them and taking care of individual needs of staff and what not. And there he was, thinking while waiting to meet the boss' secretary. He remembered his previous slim pay and how he struggled to pay the rent. Right now he needed a laptop, new...

Manipulating Jenny Ch. 04

by BeamMeUp on Sep 18, 2017
Exhibitionist & Voyeur

Summary: Voluptuous 18 year-old office flirt Jenny in stockings and garter belt, helps her boss make a decision, and she learns of another woman wanting to meet her for a lesbian encounter. Tuesday arrives a week after Jenny's 55 year-old grey haired boss says he will discuss giving her a substantial pay rise. He gives her the day off so the staff will not...

Secretaries Club Ch. 02: Trixie

by Liver96 on May 11, 2020
Transgender & Crossdressers

Second chapter of my new series. I had so many ideas at the moment I don't know which one I can start writing, but I guess somehow that's my curse. Maybe a walk with my invisible puppy should clear my thoughts *wink*. Thanks to my good friend Thanos for the help and yes, the fourth satire about the Stones will be about Mind Stone, but I forgot who could be a...

Lessons Ch. 02

by Ebenezer1 on Sep 16, 2017
BDSM

It was time for my second lesson and I was told I had to be in top form. I had corresponded with a woman to be her sex slave. She agreed only if I could prove myself. I had written a long list of kinky things I was willing to do for her. She wanted me tested by her boyfriend. She made it clear if I passed the tests, I would be her slave but used mostly by he...

Secretaries Club Ch. 01: Anna

by Liver96 on May 11, 2020
Transgender & Crossdressers

Secretaries' Club: Anna Hello everyone, I'm glad to finally introduce you a popular fantasy. Secretaries have some kind of turn on (not sure if eyeglasses are the reason, but one of them), but what if you find out things materialize in the wrong way? With luck (and time) I hope to write some episodes about this, once again; thank you Thanos for support (sor...

Secretaries Club: Anna

by Liver96 on Apr 13, 2020
Transgender & Crossdressers

Secretaries' Club: Anna Hello everyone, I'm glad to finally introduce you a popular fantasy. Secretaries have some kind of turn on (not sure if eyeglasses are the reason, but one of them), but what if you find out things materialize in the wrong way? With luck (and time) I hope to write some episodes about this, once again; thank you Thanos for support (sor...

Keeping the Boss Happy!

by SLICKHEAD on Sep 14, 2017
Loving Wives

This story happened year's ago when me and my wife Joyce first got married and the company I worked for was looking for an secretary and my wife applied and got the job in a different division than I worked, So no one knew she was my wife. But I had no way of knowing what was about to happen, It all started when two of the salesmen, Fred and Dave, asked if...

Bound Breasts, Office Toy

by HeyAll on Sep 25, 2017
Group Sex

Shannon was excited to be called into her boss's office for a strategic planning session. It was a right she had earned; she had busted her ass at the largest bank in the city to get the coveted title of Senior Lending Manager at the age of twenty-eight. Before entering his office, she made a quick stop in the restroom to straighten her suit and tidy her a...

Andrew and the Japanese Wife

by AndrewStories on May 7, 2019
Interracial Love

These stories are based on my crazy fun life. More info about me in bio. The tall muscular Andrew Jackson looked over the office of the Japanese company he had just acquired. It was the CEO corner office on the 11th floor filled with expensive furniture. Andrew had never owned companies in Japan before but from what he had read when he had googled Japanes...

Casey's Stories Ch. 02

by mattpantyhose on May 7, 2019
Erotic Couplings

Casey was not only young and beautiful, but also intelligent and successful, a well-educated nerd turned businesswoman; she run a prosperous IT company which was large enough to have a spacious and well-furnished office for the boss. Most of her employees were young men, often students who admired their boss' skill as well as good looks. Casey was aware of t...