Master Sissy Stories

61,161 results
Orientation
Length
Source
Infinite Scroll

The Spy who Fucked Me

by StephanieSeymour on Sep 16, 2017
Transsexuals & Crossdressers

I can't tell you my name, but if you'd probably recognize me if you've picked up a copy of The Wall Street Journal in the past three years. I'm the CEO of a large Midwestern company. Thousands depend on me for their paychecks. Millions rely on me to stock grocery stores with toilet paper and 10 brands of breakfast cereal. A few words from me to the right peo...

One Bath Changed My World

by johnnyt724 on Sep 16, 2017
Transsexuals & Crossdressers

My name is Johnny, by no way do I consider myself a writer in any way. This is a story that I can finally speak about, here is a how One Bath Changed My World. ***** I grew up in upstate New York in a great old city I rather not name here. When I was in my senior year of high school 1984, I started to seriously think about what I wanted to do with my life....

The Deadworld Chronicles: DOR 01

by Roukley on Sep 16, 2017
Erotic Horror

THE DEADWORLD CHRONICLES "Dawn Of The Rising" This is the first chapter of Dawn Of The Rising, book I in The Deadworld Chronicles. Not all chapters will be placed in Erotic Horror so if you find yourself interested in the following, then keep an eye out, for as often as I can I'll post these chapters unedited and roughly written in the style most autho...

Horizons

by falcon29 on Sep 12, 2017
Erotic Couplings

Paul opened his eyes again. The stars were like jewels spilled over the arch of the sky. There was no moon and no breeze disturbed the surface of the pool. Paul was lying in the shallow end with only his face, from nose to his scalp, above water. He treasured these quiet times when he could lie naked in the pool. He and Virginia swam naked all the time. The...

Mando & Lek

by Purple_Raihne on Sep 16, 2017
Romance

(I was writing this story when I was involved with two people. The three of us were the character basis. But they ended up committing to each other and forgetting I even exist, so I have no desire to bother trying to finish this story in the slightest. No names need to be changed as I already changed their names and Marie is my own middle name. To whomever d...

Anniversary Surprise

by patricia51 on Sep 14, 2017
Group Sex

(Note: If you haven't followed Sally from my other stories, well, don't worry. She's pretty self explanatory.) Sally was bored. The slender older ("40's something, if you please!") brunette glared around her hotel room as though it was the room disappointing her. She kicked off her flats and proceeded to scatter her gray business pants suit around the room....

Miss Khandie Ch. 03

by SweetNightingale on Sep 16, 2017
Transsexuals & Crossdressers

(Dear readers, sorry it's taken so long to post this next part, I'm busy with RL shit. Feed back welcome, please please please tell me what you think!) Xoxo Nightingale [1] Alright, so we all know that whatever happened between Frank and I...Will never happen again....right? I love Tanya, not Frank. I hope you all know that. We also know that we were ma...

Humiliation Slut Audition

by trenchantone on Aug 31, 2020
BDSM

It must have been a dozen years since I'd last seen Donna. Knowing that changes had come into my life in that time, I could only imagine how her life had changed. Looking around her waiting area, I had the sense that her architectural business was thriving; the room was nicely decorated. I was looking around because I was nervous. I was surprised when she a...

Where did My Damn Key Go Pt. 02

by PascalSage on Sep 24, 2019
BDSM

It didn't take me long to find something to wear. The lucky choice of attire was a sexy school girl's outfit I used to wear in a lot of my "private" encounters. It was complete with a blouse and plaid mini skirt. To make sure I was up to bitch's standards, I threw on some makeup here and there to give me a bit of an edge. A little bit of lipstick here, some...

Weekend in New Hampshire Pt. 03

by grant50 on Mar 2, 2020
Transgender & Crossdressers

Sam woke up and found that it was still dark. He needed a few minutes to figure out where he was and what he was doing. The first thing that he realized was that he wearing a nightie; then, that he was lying in bed next to his friend; and finally, that his friend had thoroughly fucked him a few hours ago. He actually thought for a minute that he had had some...