Sissy Halloween Stories

12,071 results
Orientation
Length
Source
Infinite Scroll

Roommate Dress-Up

by silkstockingslover on Oct 26, 2020
Transgender & Crossdressers

Summary: Straight guy is feminized by female beauty. Note 1: This story is dedicated to the real Mike who requested this story. Note 2: This is a 2020 Halloween Contest Story so please vote. Note 3: Thanks to Tex Beethoven and Robert for editing this story. Roommate Dress-Up "Shit," I sighed, as I saw my outfit for the wedding... I should have guessed s...

Darling Nikki

by Latexsissy69 on Sep 25, 2017
Transsexuals & Crossdressers

Chapter 1 - The Setup "I'm going to catch him!" Samantha thought to herself as she looked at her disheveled panty drawer. She now had proof that her roommate, Nick, had been wearing her clothes, but had to catch him in the act. She did a search online for ideas on how to catch him. She looked at cameras, tape recorders, etc... but she knew it wouldn't hold...

Groomed to Depravity Ch. 01

by ssamlee2000 on Apr 22, 2020
Transgender & Crossdressers

I kind of liked it. The feeling of black sheer stockings on my legs. I rubbed my legs together to enjoy the smooth, silky sensation. I looked in the mirror and take the sight in: a thin Korean boy, just about 5'6" in height, dressed like a cute skater girl. I was getting ready for the big college Halloween party. As a long-standing tradition, the college he...

Halloween Agreement

by princess_nicole on Sep 16, 2017
Transsexuals & Crossdressers

Halloween was fast approaching. This made me nervous as my new girlfriend had gotten me to agree to a costume I would never have thought I'd wear. A school girl. She said it would be fun, and that nobody judges on Halloween. Not that she had to try convincing very much, I cave in to her every whim pretty much all the time. I guess you could say I have a fair...

Halloween Pool Party Pt. 08

by sissymissyct on Sep 14, 2017
Fetish

Friday morning cam and I was awakened with an electric shock that ran from my tits to my clit. My eyes flew open to see Miss Maddy and her girlfriend each with one of my nipples in their mouth. Pulling at the rings with their tongue, my high pitched squeal announced I was awake. My clitty tried to get hard but had no place to go. I reached to touch it and co...

Futanari Academy Ch. 14

by TheOrcKing on Jun 10, 2019
Transgender & Crossdressers

(All characters participating in sexual activity are age 18 or over.) This chapter is a repost, it has been edited and has undergone very minor rewrites for style and flow. Nothing in the story has been changed. Halloween Special, 2018 Danielle walked up the steps to her friend Maddie's house, still wearing her Westbrook school uniform which now consisted...

A First Time at the OBGYN

by sissypt on Oct 19, 2020
Transgender & Crossdressers

I had been feeling under the weather but since everything had started getting into the doctors office was not an easy task. I had been staying at a friends house since i got kicked out of my mom and step dads for not "following the rules" there was more to it but that's for another time... Having had a sore throat sucked and with all the covid scare my fri...

A Sissy's Halloween

by Evangeline_E on Oct 29, 2018
Transgender & Crossdressers

Disclaimer/authors not: All characters in this story are over the age of eighteen. This is my first story so criticism is wanted as long as its constructive. I make these stories based on what I want and my own sexual fantasies. Thank you 😊 . * To tell this story right I need to start at the very beginning, the time where I first started to question my se...

Sissy Boy Secretary Ch. 07

by Hotenuf4u on Sep 19, 2017
Fetish

Elaine and Tammy had been friends before the unfortunate divorce and still now maintained a good friendship. After all, it was Elaine that helped her get a job as an executive secretary during all of her school breaks, including throughout the summer break. Tammy had known that the company Elaine got her the job at was also Elaine's biggest competitor in the...

Filipina Cuckolds Her Sissy Husband

by nancyvasquez on Sep 14, 2017
Transsexuals & Crossdressers

If there's anything more sexy and exciting for a closeted sissy than dreaming about being a woman on your knees getting ready to serve a big black muscleman, it's actually having the balls to go out there and make it a reality. It happened to me! I was married, to a hot sexy girly-girl Filipina. When we got married I was still trying to be in denial about my...