Sissy Boss Stories

46,032 results
Orientation
Length
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Infinite Scroll

Fukee Sukee Beach

by JamesMiehoff on Nov 19, 2018
Erotic Couplings

Copyright (c) 2018 James Miehoff, All Rights Reserved. This work may not be published whether for fee or free without this copyright. --------- This is one of a series of stories set in what I call Universe-J. Universe-J is very much like this universe with a few exceptions. First the people tend to be a little more sexual and less hung up on sex that...

The Last Range War

by Egmont0409 on Aug 31, 2017
Humor & Satire

A SATIRE, perhaps historically incorrect in places. INTRODUCTION In 1912 a rancher's son Lee Stanton, aged twenty-two who was heading home after failing final exams to qualify as a pastor, unintentionally started an escalating feud between the Stanton and Murphy families that probably was the last of the range wars. You won't find it in history books beca...

I"M Not, Really, I'm Not Pt. 02

by gbr2004 on Sep 14, 2020
Fetish

It's Saturday and I can't stop thinking about having to go out this evening and having dinner with Mr. Grant but I know there is no way out of it. I'm watching a game on tv when the doorbell rings. When I answer it, there are two men standing there. One is holding a couple clothes bags and the other several boxes. 'Are you Steve?' and when I answer in the a...

And He Called It Research

by thornapple on Sep 14, 2017
Novels and Novellas

Philip Johnson Prologue The offer of impressive things for free creates greed. Start by throwing in a generous amount of free vacation with impressive free goodies, and all worth tens of thousands of dollars. Add a few vital ingredients like...well let's throw in a great amount of nudity. Add a lot of passion and lust, and cook the recipe in a hot tropi...

Sissy Awakening Ch. 02

by Torbjornson on Oct 19, 2020
Transgender & Crossdressers

- A Sissies Choices - It was sometime in the middle of the night I woke cold, just laying on top of the covers I realized I was hungry as hell too. Still wearing the clothes they had put me in when I left the spa, I wrapped a blanket around my shoulders and headed for the kitchen. Standing there hungry but not wanting to really make anything I saw the jar...

Trip to LA Pt. 03

by gbr2004 on Mar 3, 2020
Fetish

This story contains forced fem, gay sex, discipline among other fetishes. If not your thing, please pass by this story. ***** I force myself out of bed and can't stop thinking about last night and even worse thinking about it continuing today. I go take a nice hot shower and that help some but when I come back into the room and see the pink pumps and the s...

Legally Binding

by MistressMtoyou on Aug 31, 2017
Fetish

As I explained in my first story (My first submissive), I'm fortunate to have a high paying job at a large well known firm. While my employer is equal opportunity and all of that, even the most open minded employer wouldn't react well if they learned they had an amateur dominatrix on their senior staff. Accordingly, before going much farther with my little h...

Steve to Stevie to ?? Ch. 08

by gbr2004 on Sep 19, 2017
Fetish

Ms Storm has exposed me to my boss, showing her that I'm nothing but a sissy faggot. It was so embarrassing. Then she watched as my Mistress took my virgin asshole. Ms Storm talked to my boss, Ms Hunter, telling her that she wanted her to keep me in line at work and make sure that I remembered my place while at work. She gave Ms Hunter permission to use me i...

Sissy Masochist

by _pdy_ on Sep 24, 2019
Transgender & Crossdressers

I'm writing this because, personally, I really enjoy writing about my sexual desires and turn ons. I find it very taboo to express these secret thoughts for strangers on the internet to see, and to be completely honest, I have a massive hard on as I write this. Well, not massive, quite the opposite actually, but you get the point. Reflecting on my previous...

Sissy Joanne Parr Fantasy Fucking Ch. 01

by Sissy Adele Howells on Aug 18, 2017
Fetish

Joanne Parr was 26 years of age. She had an obsession with the Barbie doll . She wanted to look like Barbie, as well as dress like her. One day in the office, I was so jealous of her. How dare she wear pretty dresses, when they would look much better on me. I want to be the new Joanne Parr, but I needed help to allow my kinky fantasy to take place. Georgina...