Office Sissy Stories

94,002 results
Orientation
Length
Source
Infinite Scroll

It Only Gets Better

by ElderDirt on Sep 14, 2017
Romance

Author's Note: This is a story about how a chance meeting led to a much younger woman becoming an intrinsic part of an older bachelor's life. Readers be warned that if you are looking for raunchy and frequent sex, you will be disappointed. The sex that follows is just the spice added to the meat and potatoes of the love story This is my first venture into...

My Father, The Maid

by SissyOona on Oct 16, 2018
Transgender & Crossdressers

I thought it was really weird when I received the random text from my step mother, even though I had known her for most of my adult life as my father's new wife we had never really been close. Hell, for that matter I had never really been close to my father either, he was always pulling long hours at the office when I was young, so he was never around. Nowad...

From a Husband to a Dutiful Sissy Ch. 02

by Sissy_Chantel on Sep 18, 2017
Transsexuals & Crossdressers

Chapter Two: My reveal, a true reveal for the sissy in me. I reach to the bottom of the stairs and at the front doorway entrance, Helen and Jenny are standing and looking at me in my black maids dress, white tights, black velvet 5 inch spike heel pumps, wig and makeup. The look on their faces seeing me dressed as such is priceless. This is the first time He...

Behavior Modification Institute Ch. 10

by NancyPan on Sep 12, 2017
Fetish

Although I continue to receive some demeaning and aggressive comments, most feedback has been positive. I appreciate all who enjoy this story, as we share similar fetishes. If you are not interested in FemDom, male feminization, and sexual humiliation, do not bother to read this series. ***** I was standing with my petticoat and the skirt of the maid's uni...

Lesser of Two Evils

by Andi_Lembke on Sep 25, 2017
Transsexuals & Crossdressers

[So to update you all. I'm sorry I haven't completed any more chapters of NWTBYG or Porn Princess. They're in the works, but creation, and good storytelling takes time, something I have less of now. I left my receptionist job to take a writing gig, and all my writing energy is going into that, but my passion for hot stories smolders intensely under the surfa...

A First Time at the OBGYN

by sissypt on Oct 19, 2020
Transgender & Crossdressers

I had been feeling under the weather but since everything had started getting into the doctors office was not an easy task. I had been staying at a friends house since i got kicked out of my mom and step dads for not "following the rules" there was more to it but that's for another time... Having had a sore throat sucked and with all the covid scare my fri...

Husband Made Slave

by redwolf555 on Jul 1, 2019
Fetish

The woman; Ruth, Mariah, Monique and Lisa, had been have been friends for many years, since high school. Each was 32 years old and each had been married for 6 years. They had been meeting weekly for over 4 years at a small Diner for lunch. The four women chatted for several minutes when Ruth asked, "Lisa, you are looking so contented and happy, what's your s...

Steve's First Adventure Pt. 02

by gbr2004 on Mar 26, 2019
Fetish

Total fantasy. Do not read if not into gay sex, domination and forced fem. ***** After that first experience, things didn't get too crazy like I was afraid they might. I did meet with Daddy several more times in the next couple months. There were more spankings as he taught me it was better to do as told, that if I resisted things would just get worse. He...

Welcome Home, Ma'am

by Miss_Ds_slave on Sep 12, 2017
BDSM

He had been waiting his whole life to find someone like her. He had almost given up any hope that there was someone out there who could give him what he so needed. He had met a few women over the years that had been willing to try and give him what he desired, but it was usually just something they did for him, not something they enjoyed for their own pleasu...

Office Cumslut Ch. 01

by DrLuverotica on Sep 12, 2017
Loving Wives

FRIDAY MORNING "Are you going to work dressed like that Jo?" My wife was dressed in black, sexy high heels, black stockings with a pink 1920s style pencil line up the back of them, pink frilly satin panties (she hates thongs) and matching push up bra. "Yes I am hubby," she purred, as she pulled a navy blue, short pleated skirt over her hips. "Is there s...