Shemale Boss Stories

41,656 results
Orientation
Length
Source
Infinite Scroll

Another Day, Another Dollar

by Svenskaflicka on Sep 13, 2017
Group Sex

"Claire! I've got a special assignment for you!" I walked into my boss' office. Joanne was arranging some papers on her desk. Due to the warm weather outside, she had opened a window, and now the wind was messing up her papers. Finally she placed a large blue jelly dildo on top of them as a paperweight. "As I was saying," she says. "I've got a special ass...

A Night Out With Friends Ch. 02

by wyo_girl on Sep 14, 2017
Erotic Couplings

Thumbing through the mail I'd just carried in, I tossed my keys and handbag onto a chair. I'd seen an orange envelope hiding amongst the bills and catalogs as I'd pulled it all out of my mailbox and I wanted that envelope! Nick hadn't been able to come see me for a couple of weeks and work was keeping me at home too. My hope was that this was a card from him...

Fancy Series: Tickles Your Fancy

by badgirl298 on Sep 13, 2017
Celebrities & Fan Fiction

*~* Giles circled Willow, a small bundle of burning herbs in his hand. His face was lined in concentration, focusing on the book he held in his other hand. As he ended the the spell, the Watcher said."Let the demon depart!" He scrutinized Willow, looking for evidence that the spell worked. There was small surge of energy that went through the young redhead,...

Bargain Basement Bitch

by English Bob on Sep 14, 2017
Loving Wives

Jasmin Lacey sat behind her desk, a very wide smile pasted across her pretty face. To anyone within her office at that time, it would have been obvious why she looked so happy: kneeling between her open legs was her husband and sometimes secretary, Ben. Ben's head was buried between her thighs and he lapped contentedly at her wet pussy while Jasmin built ste...

Lisa Gets What She Wants

by clintorres on Sep 16, 2017
Interracial Love

It's Friday afternoon, approaching three-thirty, and I've mentally checked out for the week. "C, please come in here," my boss Lisa calls out from her office, jolting me back into real time. Grabbing my electronic notebook, I quickly move to her doorway, and tap softly on the frame. Still gazing down at the document in front of her, and without looking up...

Fire In The Hole!

by English Bob on Sep 17, 2017
Loving Wives

Fortunately, there wasn't too much damage and nobody was hurt. The fire that had started in our kitchen hadn't spread to the rest of the house and, by the time the fire department arrived both my wife and I were waiting on the front lawn still dressed in our night-clothes. We watched the fire fighters work quickly and heard the occasional snigger and giggle...

The New Boss

by mrshyboy on Sep 14, 2017
Group Sex

Anna and Kayleigh had worked in the same office for the last few years. Both in their mid 20s they did almost everything together, worked, exercised, double dated and cried over failed romance together. Lately they'd shared more than a kiss, but didn't consider themselves together as a couple, more as friends in need. Everything was going smooth and norm...

Natural in Nature Ch. 01

by slickorslide on Sep 1, 2017
Exhibitionist & Voyeur

Chapter 1: Heading Out Throughout the years, there have been many stories, books, and movies with the theme of being stranded in the wilderness. Swiss Family Robinson (Disney-ized version of the theme), The Blue Lagoon (with a young Brooke Shields), Cast Away (with Tom Hanks and that annoying volleyball), and the reality type shows Survivor and Lost. It was...

The Bad Apples

by Mabthorn on Sep 1, 2017
Humor & Satire

"Fucking webslinger, get your crotch outa my face or I'll tear it apart!" Komodo was baring his fangs at Spinner. Spinner was, as always, hanging down from a beam, his crotch directly in front of Komodo's nose. And he had a boner. Nice. Leaning against the bar, I watched the action. "Come on, big boy, we all know you want this bone," Spinner taunted, swing...

Unbound, Unmasked Ch. 01

by darkknight0307 on Sep 17, 2017
BDSM

Author's Note: This is the first chapter to a story I have been working on. I've got about fifteen thousand words going, with about five and a half chapters done. The goal is to publish, but wanted to post the first chapter up to prove I'm not dead. All Characters are Eighteen Years of Age or older. ----- I liked what I saw when I looked in the mirror....