Sissies Stories

1,006 results
Orientation
Length
Source
Infinite Scroll

Compromised

by HorribleHenry on Jul 6, 2020
Transgender & Crossdressers

STORY OUTLINE/SYNOPSIS On holiday in Jamaica Sandy Armstrong's eyes lingered too long on three feminine items in a display window. By biometric means he was singled out as a possible sissy or the like, and the information sold to an international organisation. Sandy receives a surprise visitor at his flat in London, a shemale, who seduces him and he eventu...

Don't Lie Ch. 01

by Scribler on Sep 13, 2017
BDSM

All I can say is don't lie to you wife. If I didn't I wouldn't be in the situation I found myself in. It really wasn't that big of a lie but it was enough as far as my wife was concerned. It started a few weeks before we got married, five years ago. My wife Dawn decided that she wanted to tell me everything about her sex life before we got married. She sai...

Fantasy Weekend

by DWornock on Sep 24, 2019
BDSM

MF, MM, MMF, FMF, Fetishes: sexual role-playing, cross-dressing, domination and submission, and pain. The youngest person in this story is a 19 year old receptionist. 4Play has given me permission to make modifications and additions to his story "Date Night." I changed the title to "Fantasy Weekend." I also added the first paragraph to chapter 1, deleted...

It?s Either Break Up Or Make Up

by felicia_rene on Sep 12, 2017
Transsexuals & Crossdressers

PART 1 Synopsis: I always was put off by the unsuspecting stupid love sick, pussy whipped guy is transformed against his will because the will wants to run off and have an affair, I never understood why they don't just pack and leave. The underlying theme is transformation and sexual punishment of the main character with anti gay womanizing feeling for hi...

A Fantasy about Love Pt. 05

by Buzios1971 on Oct 8, 2019
Romance

Chapter 17: The Flare-Up I welcomed my work after all these troubled, but strangely satisfying days. A load had been lifted from my soul and I could dedicate myself to work. When I entered the building, I received more support from my colleagues than I expected -- perhaps I was not such a cold German after all; the influence of Maureen had probably changed...

Soul Sisters

by frezrevup on Sep 19, 2017
Transsexuals & Crossdressers

Novella Length ~ 35,000 words For those that can't wait: Ch.19 - First Date with black man Ch.20 - Sissy Sex Soul Sisters Chapter 1 Lori swept into our lives like the hot August winds of Tucson. My wife, Erin, and I moved there for the fall semester when I got a job as an assistant professor at the law school. Erin found a job at Lori's dad's small acc...

Mistress Maggie

by Joscelyn2tg on Sep 15, 2017
Transsexuals & Crossdressers

My Dear Reader, Welcome to a most unorthodox love story. A story containing romance, transgenderism, spirituality and yes, even S&M. But first allow me to ask you a question, and when you reach the end of this story, it will make much more sense to you. If your soul returned in the body of someone else after you died. And you were allowed to whisper one th...

Doc and the Porn Star Ch. 16-21 - End

by SteveWallace on Jun 17, 2019
Group Sex

Chapter 16 The following week was very upbeat. I let it be known at the clinic and at the partnership offices that I'd gotten engaged, so I was feted and congratulated by many of my associates. Several people wanted to know what my fiancée looked like, and so on Tuesday when I carried my iPad around, as I usually do to do doctor things on; I had Jasmine's p...

Killing Daddy Blue

by WickedDrX on Sep 12, 2017
Novels and Novellas

Wednesdays were always boring for Holly, and this one was worse than most. Her usual trade didn't hit the streets until the end of the week when they got paid, or until the welfare checks came. This wasn't the week for the welfare checks. It was cold, and there was a light mist falling that promised to turn into snow very soon. She could move up a few blocks...

The Domme Diet Plan Pt. 01

by subm_atty on Sep 11, 2017
Fetish

Day 1—The Plan I have been fat as long as I can remember. I have tried various diets with no lasting success. Being uncomfortable with my body was probably one of the many factors that drew me into being a submissive. Two years ago, I met the Domme of my dreams. My Mistress was about 5'10" but towered well over 6' tall in the heels she usually wore. Her hai...