Shemale Boss Stories

41,656 results
Orientation
Length
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Infinite Scroll

Sam

by Pars001 on Jan 20, 2020
Sci-Fi & Fantasy

Samuel Ray walked out of his house waving to his neighbors. Getting into his car he stretched his six foot frame out behind the wheel. Moving away from his house and neighborhood, little did he know it would be the last time he'd see either of them. High in orbit above the earth, an unearthly craft was hiding among the satellites. It's sleek black skin abso...

Switching Drivers

by MartinFaust on Dec 31, 2019
Erotic Couplings

"It's just something I want to try out. Penny was talking about it at the party last night." I was laying on my side in bed, looking at her, mirroring me. Our "Talks", when they were in bed, usually involved something about our sex life. They were admittedly, until this very moment, also usually brought up by me. It's not that I was unsatisfied with our s...

Control - Pope's Pleasure Protocol

by pinkysurprise on Jan 28, 2020
Celebrities & Fan Fiction

Jesse moaned as someone kissed her neck, trying hard to ignore the knocking on her office door. But the sound was insistent, and reluctantly she was pulled from her dream. She found herself laying on her couch, sleeping under her leather jacket. The details of the dream were fading already, leaving only impressions. Blonde hair. A nipple stiffening in her mo...

Jack

by Sophiem98 on May 4, 2020
Erotic Couplings

**This story is based off of a dream I had a while back, and I was encouraged to write it down. It's my very first story, so please be kind. And thank you for taking the time to read it.** *** Sophie had done it. She had made a Literotica profile. Oh lord. If her mother knew, she would kill her. Actually, scratch that, her mother would think it was funny....

Dinner with my boss.

by ghost12_spirit on May 11, 2020
Erotic Couplings

Please note that there is no one in the following story under the age of 18. -------- It had been the third long day in a row. Corporate meetings in the dead of winter, it was dark when I got up, and it was dark when the last meetings finished. I am younger than all of the other managers and the only male in a group of twenty-five women, all in their lat...

Cumming to Work Late

by WomenWearThePants on Apr 15, 2020
Toys & Masturbation

Lane was wet. Her alarm had gone off and she woke with her leg thrown over a pillow, her phone nestled between her sopping pussy and the pillow she had been fucking in her sleep. The vibration, although not quite against her pussy how she needed it to be, only encouraged the blood pulsing pleasurably. Groggily, she reached into her bedside table and palmed...

Sam's Boss - A MFF Threesome

by Bearfactz on Jul 2, 2019
Group Sex

Sam had been working long and hard hours as her boss had driven through a new contract to a tight deadline. Despite all the pressures he'd always been very good to his P.A. and she'd reciprocated by working some anti-social hours to help him meet his delivery schedule. She was looking forward to the weekend and some much needed 'me-time'. "Sam, I'd like to...

On the Hunt Ch. 05 - The Walk

by Lisa2506 on Aug 6, 2019
Exhibitionist & Voyeur

Hi Madam Lisa here. I would like to welcome back and thank the readers that have made it this far. This is part 5 of my ongoing real life story. If you have not read parts 1 through 4 please do it will help you follow along. All participants are over 18 and have consented to their rolls. *** Recap: I was spit roasted at the gym, Lots of sex after diner. Ma...

Monster Musume: Stress Relief

by Venus444 on Jul 16, 2019
Celebrities & Fan Fiction

Working as an agent upholding the Cultural Exchange Interspecies Bill and being leader of the MON squad is a thankless, taxing job. Kuroko Smith was an overworked yet dedicated woman who saw to it that she got the job done with as little paperwork as possible...which was an impossible job considering that liminals were a hassle to deal with on a daily basis...

Administrative Assistant Pt. 01-02

by DZiegler on Oct 21, 2019
Sci-Fi & Fantasy

Administrative Assistant (Pt. I) - CoWorkers Fluttering between open and closed, my eyelids betrayed my true thoughts about the meeting I was currently sitting in: Pointless. Unnecessary. Aimless. Unproductive. I was representing the engineering team in the, now bordering on three hour long, meeting regarding a large new account that the sales boys had man...