Sissy Secretary Stories

20,580 results
Orientation
Length
Source
Infinite Scroll

Jasmine Fucks My Wife

by cuntenslaver on Sep 12, 2017
Transsexuals & Crossdressers

Hello, my name is Tim. I am a 30 year-old married man. I have been married for five years to my wife Danielle. She is an absolute beauty of a woman. I remember when we were married, I felt like I was the luckiest man in the world. Since I am no hunk myself, standing at just five foot six and extremely lanky, I felt like I didn't deserve such a nice, gorgeous...

His Sissy Bitch Ch. 02

by keptsissy on Sep 18, 2017
Transsexuals & Crossdressers

The next day at work I felt my face flush every time I saw him, felt embarrassed and felt like stammering every time I spoke with anyone in the office. His office is across from mine, he's my boss and I have to see him daily. It felt like everyone in the office knew! I was so nervous I didn't speak to anyone, avoided everyone as best I could. He didn't say a...

My First Time as Sara... Pt. 05

by Sexy_SaraCD on Sep 18, 2017
Transsexuals & Crossdressers

I've become Sara now for just about a year. One year of exploring deeply who I was, my past, my history and who I've become at this moment. I was no longer just John, the meek man who was dumped by his fiancé for not being man enough. That skin was shed. Instead I became Sara. I became empowered and in charge of my life. It was as if panties and heels, cut...

Lessons: First Time

by InYo on Sep 13, 2017
Fetish

I found her name in the back of a local swingers newspaper, in small print, at the bottom of a column. "Mistress Jade, Private training sessions, Become the man I want you to be." I clipped the ad and carried it around in my wallet for almost a month before I got the courage to call. A formal sounding older woman, who told me that the Mistress was busy with...

Subliminal Obsessions Ch. 03

by Sissyhalo on Sep 13, 2017
Transsexuals & Crossdressers

*Before... She shows me our profits and stuff...and stuff meaning gifts with cash transfers and e-notes sent for who. I'm floored, literally floored I've never had this much money in my life. I'm not rich but holy fuck...I can...I just sit and stare and look at the screen. "What are you going to buy first Nikki?" "Bills, bills and some savings but the r...

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...

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...

Meet the Danvers Ch. 02

by eeric on Nov 26, 2019
Interracial Love

Jim Danvers sat behind his desk on the third floor. He had been the office manager for the last five years, and the last couple of years had been quite profitable for the company. "Have to congratulate you again Jim, another year, and we've seen nothing but increased revenue streams and productivity from your floor." Charles Vanderholm stood up. The man wa...

A New Start

by Stoked Flow on Jun 20, 2020
Transsexual

You spent most of your time at home playing video games and browsing the internet. You decided to take it easy after high school before deciding college was right for you. That was a couple years ago and now you sense a growing frustration within your mother. One afternoon after dinner, you found yourself suddenly sleepy and crashed onto the sofa. Your next...

Open in Reader

Chantz and Brittany's Toy

by humbleslave on Sep 16, 2017
Celebrities & Fan Fiction

This is a continuation of Being Brittany's Bitch. Please read that first in order to get a feel for the whole story. * I had just been delivered back to Brittany and Chantz by my former wife dressed (technically) in an open, low cut, white blouse, short black skirt, and 6 inch black platform heels. My mussed hair and glasses were stained with my own cum f...