Sissy Shemale Stories

7,624 results
Orientation
Length
Source
Infinite Scroll

How I Became Sissy Willow Ch. 04

by willow619 on Sep 12, 2017
Transsexuals & Crossdressers

It was now Saturday afternoon. Last night, after I'd returned home from work I had been dressed in women's clothes by my wife, Allie; introduced to her lover, Mike; been made love to by him myself; been subjected to physical and emotional torture by the two of them; and had it all captured on video. This morning I had had all my body hair removed and had pa...

Lois Lane's Night Out

by exxxidor456 on Aug 13, 2017
Fan Fiction

As with all my stories, I welcome other authors to add chapters! Remember to like and bookmark your favorite chapters! Regular chapters with 5+ likes get a sequel, chapters with 10+ likes get two. End chapters get an epilogue with 10+ likes. Chapters with the most likes & bookmarks get updated first! All characters in this story are at least 18 years old...

Open in Reader

Kinky Bride Confessions Ch. 8

by yano on Sep 16, 2017
Interracial Love

Wedding Day Preparations - Part One My girlfriend Emma continues to describe her first porno wedding and her first day at the Kinky Brides Group. "The morning of my kinky wedding I met Bree at 10am and then went to the appointed meeting place to be collected by Mr. Belston. Bree and I carried an overnight bag, each of us telling our parents that we were st...

The Suitcase Ch. 01

by SissyGeorgina on Sep 19, 2017
Transsexuals & Crossdressers

Enjoy the story, more to come, as soon as I'm able. It all started when I was 25. After graduating with a 2:2 degree in English from Plymouth University, I'd moved to London and gotten a job as a journalist for the Evening Standard. The pay wasn't great, and I was making next to nothing after paying off my rent, travel and living costs. I certainly didn't...

Allyson's First Blowjob

by sissymaidallyson on Sep 16, 2017
Transsexuals & Crossdressers

I have been a closet cross dresser for many years. A few people knew but it wasn't well known and that is how I liked it. I enjoyed dressing up and prancing around my flat in ladies clothing but I always had fantasies about going further. I kept stopping myself from doing anything further but there was that burning desire to be truly slutty inside of me. On...

Money Shot Pt. 02

by GavinIsaNuisance on Jul 27, 2020
Transgender & Crossdressers

This story is entirely fictitious. Any similarities to persons or things living or dead is purely coincidental and completely unintentional. All persons depicted in a naked/sexual nature are 18 and up. Tanya introduces a newly sissified Danny into the world of erotic photography which gets them into a hot offer they can't refuse. Author's Note: So, I establ...

My Wife, My Tormentor

by Sissyjackie2008 on Sep 16, 2017
Transsexuals & Crossdressers

I am excited by the . One of the most humiliating experiences I sufferer was caused by my first wife. I had been a crossdresser since I was little. Actually my mother started me when she dressed me as a girl for Halloween. When at 7 I started to protest, She said she had no daughter and once a year I could let her have fun. I could never refuse her so I re...

Made to Obey Ch. 11

by madetoobey on Aug 21, 2019
Transgender & Crossdressers

Reprise: I'd been caught wearing my Sister-in-law's underwear and jerking off to shemale porn by wife (Ruth), Sister-in-law (Esther) and their mother (Donna). I'd been forced into a chastity cage and made to wear panties all the time. Humiliation was now a frequent event. Esther, who had investigated my internet usage on my laptop to see if I'd visited shema...

Heidi’s Submission

by TimT1972 on Sep 19, 2017
Transsexuals & Crossdressers

Eighteen year olds are the same the world over. The handsome, tough and sporty are nearly always the most popular. Adam was none of these, he was rather effeminate, of slight build and definitely no sportsman. As such, he never had that many friends. His home life wasn't much better; his father was dead, he had no siblings and his mother worked every hour Go...

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...