Boss Lady Stories

105,242 results
Orientation
Length
Source
Infinite Scroll

There's No Stopping Jennifer

by alexcarr on Sep 13, 2017
Erotic Couplings

There's no stopping Jennifer. I was going to show Jennifer. She was always moaning and badgering me until I had reached my wits end. Crude or not I just had to say something really vile to get her off my back. IA newspaper office is forever frantic but with the assistant editor on one's tail is so annoying. It is not like I have anything against female bo...

The Unwitting Guardian Ch. 10

by Arraiga on Sep 26, 2017
Sci-Fi & Fantasy

Author's Note: I don't think I can apologize for how late this is, cuz it is reaaaaaaly fucking late. I just havent been hit with that writing mood for forever, and then I was worried this might not live up to the massive expectations you guys might have of me [ ;) ]. Anyway, I decided to post this with the assurance that there won't be such a long wait for...

Rebecca Becomes a Party Girl Ch. 05

by edisonCaroline on Mar 6, 2018
Group Sex

This story is a continuation of the characters and plots developed in the story "Rebecca Becomes a Party Girl," Chapters 1 through 4. This story will make more sense if you have read those chapters first. ***** I. Rebecca Starts a Movement Rebecca was walking back to the ballroom of the firm's reception with Karen and Jordan, thinking about how the three...

My Niece Jennifer Must Pay! Ch. 06

by JRob on Sep 25, 2017
Mature

Thanks to Robyn for the suggestion on the topic of this story. She's a wonderful friend. And of course to my niece Jennifer for the motivation to write. * My niece Jennifer was only 19, cute as a button, but over the last three months she'd learn that asking her uncle for help out of a jam was just something family does. What she also learned, though, was...

The Girls in the Black Bikinis

by free1radical on Sep 25, 2017
Erotic Couplings

* * * This is a sequel to "The Girl in the Black Bikini" which I wrote inspired by the works of Chloe Tzang. I combined two different story ideas into this one. Hopefully it still makes sense. Thanks Chloe for your suggestions to improve this one. * * * Two years had passed since that wonderful tryst with Chloe at her beach condo in San Diego. We had exch...

Big Tits Tanya in a Cuckold Session

by KatieBoobs on May 11, 2020
Group Sex

Big Tits Tanya in a Cuckold Session My boss, Timothy, summoned me to his office. When I opened the door, he was seated behind his desk speaking on the phone while there was a brunette lady seated on a couch at the far end of the room. The office was a beautiful, spacious work environment that allowed Timothy to have a mini-bar, a cooker and a miniature gol...

Petra Ch. 02

by Iread2relax on Sep 17, 2017
Non-Erotic

Two weeks off! Wow! What will I do?" Petra thought after her boss left. She looked around her small apartment and decided to clean. So not wasting a moment, she started cleaning. Not that she had much, but over the years she had acquired some things. Soon she had two piles. One pile was things for the dump, and the other were things she could donate to the...

My New Daddy Ch. 07

by sissytoy20 on Mar 21, 2018
Transsexuals & Crossdressers

After Boss zipped up his freshly cleaned cock, glistening with my spit, he took me up to the 30th floor. My brain was still buzzing with my anal orgasm when he took my arm and basically forced me to walk out of the elevator. I stumbled on my heels beside him, reaching back to finger my cum-filled asscunt. I dug out some of Boss' load and licked it off my fin...

Spanking New Secretary’s Kink

by welshman on Sep 12, 2017
Fetish

"Discipline, an office needs discipline." she insisted. ~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~ It has been about two months since her second interview for the position she now holds. Impressing him in both her secretarial abilities (complemented by immaculate references) and her attire, a stylish business suit embellished by a long narrow display...

Kim Ch. 07

by Mikro on Sep 14, 2017
Erotic Couplings

Chapter 07: The Decorators The decorators had been in all week Steve the young apprentice and Boss as I called him. I hadn't had sex for a couple of weeks and was feeling really horny. I had taken a week off work, ostensibly to let the decorators in but also because I had been working non stop for 6 week's, unusually long for me but it had been a very prof...