My Boss Stories

337,088 results
Orientation
Length
Source
Infinite Scroll

Lucy's Big Adventure Pt. 02

by mjar65 on Sep 13, 2017
BDSM

NIGHT TWO DM drove me again across the city to the big house. This time when I got to the car he told me with a grin I should be naked for the whole drive. "To help you get in the mood," he explained. I didn't know what to do but it was a good idea and I knew he wanted to see me naked. So I stripped off my dress in the car and sat naked for the entire time....

Senior in the Strip Club

by mmarie3 on Sep 13, 2017
Mature

While in college, my friends had a habit of enjoying after-hours parties at strip clubs. While it was just a way to keep drinking and have fun for them, I became fascinated with the strippers and watching them flirt and pleasure all of the different men-especially the older ones. I hadn't told anyone, but I had a secret fetish for much older men and had slow...

Fun with the Boss

by CAExhibitionist on Sep 15, 2017
Exhibitionist & Voyeur

As agreed, I wore a sheer blouse, jacket, and short skirt with fishnet hose and garter belt, but no bra or underwear, not even a G-string. Sleeping with the boss isn't as bad as I'd thought. It turns out he's a kinky bastard. And of course, my unwarranted promotions sure help things along. Tonight he's taking me to dinner at my favorite, swanky -- and very e...

Ignorant Village Boy Pt. 03

by trishotoy99 on Nov 24, 2017
Group Sex

Handing over the successfully completed construction work was a relieve to all of us and especially our boss the main contractor. He did promised us all a small bonus and a party. We were all looking forward to the bonus more than the party. So we were called to his house to prepare for the party. Some of us were tasked with food preparation and others were...

My New Daddy Ch. 06

by sissytoy20 on Mar 7, 2018
Transsexuals & Crossdressers

When I woke up, my whole body was sore, especially my clittycock. My orgasm had been so intense that it seemed to continue long after I'd squirted my balls dry. Daddy introduced me to his private bath where I soaked in the tub for what felt like hours, then Daddy dressed me in another tight-fitting business suit and we ordered dinner. After the meal, I felt...

Sexy Sally, My Slut Wife

by Jigs on Sep 18, 2017
Loving Wives

Authors Note: This is a story once published at another site under the name Sexy Sally & Boss Bob. For its appearance on Literotica it has been rewritten, its plot amended, and its category changed, although it does return with the original characters and parts of the original story. I have done my best to make it as fresh and interesting to those who may ha...

Cammi Ch. 01: Good Job

by SZENSEI on Oct 30, 2018
Exhibitionist & Voyeur

My name is Cammi. No last names offered. I'm sure you understand. At 19 I began my career as a Secretary at an Insurance Firm. Again no names. For the safety of those that work closely with me. For the first two weeks I learned the ropes. It became more than just getting coffee and ordering lunch. Actual work. Files. Claim reports. I managed to get noticed q...

Lucy's Big Adventure Pt. 04

by mjar65 on Sep 16, 2017
BDSM

After my Boss told me about DM I found it hard to stop thinking all the time about this new Master. I was even more excited to think I had two Masters now and how good I felt about having two Masters to love and serve. Once I had thoughts about being lower than a man all the time and that is what I know is called submission now. But I always believed those...

Separated for a While

by assbr on Sep 17, 2017
Loving Wives

It has been a rock time between my wife and I for the last couple of months. The one thing we always got perfectly was sex, but there was none of that for the last two months, we normally make love two to three times a week. But like I said it's been a dry time. On Thursday in February my wife calls me at work and tells me to go stay somewhere else for a wh...

Confessions of a Phone Sex Girl Pt. 01

by ErikaGrey on Aug 18, 2017
Fetish

Part One - The Empire of Boss Man I started out as a phone sex girl but ended up exploring the industry a tad bit more thoroughly. What I thought would be easy cash ended up turning into a lot of hard work. The money was there. The sex industry is a cash cow. That's no lie. But it takes time and raw effort to make the mula come rolling in. Most women do...