Sissy Halloween Stories

12,071 results
Orientation
Length
Source
Infinite Scroll

Miss Guided

by MissMarianne on Mar 12, 2019
Transgender & Crossdressers

My name is Susan and my husband Charles, we are both 25 years old and have been married for one year. Recently Charles has been very depressed and He lost his job when the company moved to Malaysia. Lately his performance in bed has been sub-par and , in fact, he can't get it up most of the time. We feared he was becoming impotent but the doctor said the pro...

Katelyn's New Sissy Pt. 01

by bluesbirds on Dec 25, 2018
Transgender & Crossdressers

I remember she made me try the Sissy Peni-Pacifier in the store. It was a humiliating day outing, meant as "my" Christmas gift. Dressed up in a tiny bright red sexy elf costume with marabou trim around the edges that ended at my sissy clit, black fishnet stockings and 4" black heels, with a ridiculously large shiny red bow in my hair, surrounded by mirrors a...

Creating Ginger Ch. 08

by Ms_Allison on Aug 31, 2020
Transgender & Crossdressers

Author's note: This is a story of a loving, married couple who wanted to expand their boundaries. It involves crossdressing, gender play and their foray into dominance and submission. If these are not topics you are interested in, then please move along. ~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~ Michelle awoke to the smell of coffee, which as of late had become her...

The Writer's Secret Ch. 01-02

by AnnMichelle on Sep 13, 2017
Transsexuals & Crossdressers

Hi everybody! This is one of the many stories I've written over the years. I've decided to clean them up (read: edit the heck out of them) and start sharing them. This one has some light-femdom, a pretty willing husband, and a few fun surprises. Enjoy! * Loren had no idea what he was getting into when his agent suggested he write transvestite fiction. Nor...

Curse of the Were-tights Ch. 01

by prettypolly on Sep 16, 2017
Novels and Novellas

Chapter 1: Never Cross a Witch "I get the impression you don't believe me." I was getting inpatient, and was starting to feel very uncomfortable. I crossed my legs and pulled my skirt down a little subconsciously. I shifted on my chair. Opposite me sat Katherine ("with a 'K'", she said when she introduced herself ten minutes ago), drinking a gin and tonic...

Aficionado Gets in Trouble Ch. 03

by His_fag_wife on Sep 23, 2019
Transgender & Crossdressers

As his WhatsApp call rang to the contact simply named Master, Pete had no idea what faced him. His senses were full of Marks cum, the distinctive metallic taste, it's manly musky aroma were overwhelming for him. He was still high from the poppers and thought he should just sit for a few minutes to recover a little, although the nearly full bottle of poppers...

Signing Myself Into A New Life

by Gretatv on Sep 14, 2017
Transsexuals & Crossdressers

This is a little fantasy of mine and dedicated to my Mistress. There is some explicit language and scenes in the story and you know the drill, if you are underaged or don´t like to read (bi)sexual acts than don't bother. This story is explusively mine and can only be copied after contacting me. I haven't written in years and I hope I haven´t gotten too rust...

Seven Lessons Ch. 01

by Vertex on Sep 16, 2017
Transsexuals & Crossdressers

(1) - Acceptance Bryan was king of the road warriors. Speeding around the country in his sleek, powerful Mercedes selling whatever his latest job demanded. He was damn good at it too, always raked in huge amounts of commission until some faggotty client bitched about a one-sided deal he had put together and then it was off to another company. Talking of bi...

Sara becomes The Bride

by Sexy_SaraCD on Sep 14, 2017
Transsexuals & Crossdressers

Becoming Sara has been the most amazing experience I have ever had in my life. Between the clothes and living as her all the time, to becoming the thing men fantasize, it has been an amazing transition. While I had some good friends, girls like myself that I met at one of the trans bars in town, I did lack male friends. I was never a sociable person, very...

Becoming Mindy

by mindyrose on Sep 18, 2017
Transsexuals & Crossdressers

Hi. This is my story from an unsure, shy, awkward boy that was pretty feminine to a proud, confident and comfortable transgendered girl. If you're not into reading about transgendered people and their stories, as well as their sex lives, then please move on. I know I made some foolish decisions, but I am a completely healthy person today and those decisions,...