Office Sissy Stories

94,002 results
Orientation
Length
Source
Infinite Scroll

More Than I Wanted Ch. 02

by gbr2004 on Sep 16, 2017
Fetish

Please read Chapter One before reading this to help you understand what is happening. This story involves man on man sex, forced fem, bondage, discipline and humiliation. If not your thing, please go to a different story. Enjoy hearing feedback and ideas about my stories. Waking up the next morning, the events of my meeting the previous evening come back t...

Mistress Emma's Revenge

by sissymissyct on Oct 15, 2017
Fetish

Hi I'm Ken. Well I was, now I'm called Brenda. Here's a bit of my story for you. I hope you don't make the same mistakes I did. Because until I got caught misbehaving by my mistress, life was pretty good. At 38, I had a great job as an office manager in charge of 25 or so employees, mostly women, a really good salary, a nice office and plenty of job securit...

The Sissymaiden's Tale Ch. 01

by ppeaks42 on Mar 7, 2018
Transsexuals & Crossdressers

The world was not always this way. Though few remember it, and even fewer choose to speak of it, there was a time when things were different. Before disease ravaged the land. Before the great feminization. Before the influx. Before the Femocracy. It was whispered that once white men had been just that: men. It was nearly impossible to believe, seeming more t...

The Anniversary Present

by DrLuverotica on Sep 15, 2017
Transsexuals & Crossdressers

My wife, Jo, is a very hot, very sexy 40 year old doctor. For the past few years I've found it really difficult to please her sexually. That all changed when I bought her a Rampant Rabbit vibrator from Ann Summers for our tenth wedding anniversary. When Jo unwrapped the box containing the 8 inch silicon black vibrator she was giddy with excitement. I was de...

A Downtown Moment

by Sheermistress on Sep 12, 2017
Transsexuals & Crossdressers

I had reason to head downtown for a meeting with some industry colleagues and after my meeting I dropped in to see a friend of mine who I used to work with. Loretta and I worked together for about a year on similar project as contract workers, I moved on to other things and she stayed with the company. While I never went out with Loretta, we did have the od...

FMDM Inc - Jerry's Story

by satinmarabana on Sep 13, 2017
Transsexuals & Crossdressers

"I just want him to get what he needs without destroying my family or our marriage," said Mrs. Farrett quietly. She was sitting in a corporate office speaking to Amber Giles, a woman half her age and twice her breast size. Approaching this mysterious FMDM, Inc. had been her last resort to saving her marriage. "I understand, Mrs. Farrett," said the FMDM repr...

A New Life Ch. 04

by sissycinnamonswirl on Sep 18, 2017
Transsexuals & Crossdressers

The man's Skype camera was still showing black, but I could hear him breathing heavily as he watched me pulling the chains that attached to the clamps on my nipples. I was pulling hard enough and steady enough to begin stretching my titties...as mistress requires me to call them. It was extremely painful as the clamps themselves were little more than metal t...

It's For Charity

by Tomsparty on Sep 12, 2017
Transsexuals & Crossdressers

You gaze dreamily at the little black dress in the charity shop window. It's Christmas, it's party season and you'd do anything to wear the delicate feminine dress. You shrug your shoulders and gaze further into the shop. The company Christmas party is tomorrow and you've no idea what to wear or who to take. You stare once more at the dress in the window and...

Caught Red Handed

by desireethtttv on Sep 15, 2017
Transsexuals & Crossdressers

With Halloween falling on a Monday, my wife Suzie was busy the weekend before trying to find her costume to wear to work. As a dutiful sissy husband that loves shopping as much as any woman, I tagged along, although our choice of stores to peruse is completely opposite. Suzie is a Goodwill addict, with anything at a bargain giving her much pleasure. Me, I'd...

Larry's New Bitch

by sissyneko on Sep 15, 2017
Transsexuals & Crossdressers

I hit a bit of writers block so I grabbed an old half completed story and started back on it. This is the result. I am not the greatest at transcribing the stories as the flow from my mind. While I have given this piece a once over, I am sure that I missed something. If I did I am sorry and I hope that it doesn't pull you out of the story to much. *********...