Halloween Sissy Stories

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Black Licorice

by EROTICbearscribe on Oct 19, 2020
Transgender & Crossdressers

My name is Jamie. I am 19 years old. This is the story of what happened to me Halloween one year ago. It was the last week of October and the leaves had turned brilliant shades of orange, red and yellow. The nights were getting cooler. Everything you could imagine was pumpkin flavored. Usually I get psyched for this time of year but things were different f...

Spellbound & Sissified

by EROTICbearscribe on Oct 19, 2020
Transgender & Crossdressers

SISSY FOR A SPELL The Omega Psi Phi Fraternity loomed in front of him. The lights were on in almost every room. Frank's hopes, that maybe the brothers of Psi Phi were at the Halloween party across campus being thrown by their sister sorority Sigma Gamma Rho, were dashed. He took a step forward. His hand was shaking and the child's Jack O' Lantern bucket...

Sissy, Hypnotized

by Slipperylock on Apr 8, 2019
Transgender & Crossdressers

It had taken six months to get to this point. As I stepped out of the bathroom, I caught sight of myself in the full-length mirror, and shivered. I was shaved below the eyebrows, hairless and smooth, except for a cute landing strip above my locked chastity cage. Other than the cage, I looked like a thoroughly average 21 year old boy, my small and skinny fram...

House Rules Ch. 09

by EROTICbearscribe on Jan 22, 2020
Transgender & Crossdressers

AUTHOR'S NOTE: This story contains characters and references to events in two previous stories I have written: Just Across The Hall and PIXIE: Sissy Stripper. It is not necessary to have read these two story chains. This chapter of House Rules could stand on its own for entertainment purposes. If, however you want context, please read the other two stories f...

Panty Posers Ch. 04

by EROTICbearscribe on Sep 21, 2020
Transgender & Crossdressers

I must tell you of an experience Daphne and I had one Saturday night. I know, I know. You're dying to find out if I ever finally met Daddy. All good come things to those who wait. I really am a sissy tease. Aren't I? I think you'll enjoy this side trip though. *** It was a lazy Sunday morning. Daphne and I were sipping coffee and nibbling on some danis...

Sissy for a Day

by silkstockingslover on Oct 16, 2018
Fetish

Summary: With his wife's help and support, a man becomes a sissy for black cock. Note 1: This is a Halloween 2018 Contest Story. Be warned: this story involves sissy sex, obsession over black cock and a bukkake. If this isn't your thing, please don't read any further. Note 2: This is dedicated to the real Paul who requested this story. Note 3: Thanks to:...

Barbie's BBC Beginning

by jacki697 on Jun 9, 2020
Transgender & Crossdressers

I had always been curious about men. I had always wanted to experiment but alas I was way too scared of being "gay" to ever follow through on any of my urges. Chalk that one up to 18 years of living in a conservative Christian community. Instead I left my sexual urges to the alone time I had to indulge in my other fantasy of crossdressing. I loved the thrill...

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...

My Sissy Cuckold Life

by SissyCuckMike on Jan 2, 2021
Fetish

Hello everyone, my name is Mike and i am now a sissy cuckold. If you don't know what a sissy or a cuckold is i will explain, a sissy is like a cross-dresser but usually dresses up in pink frilly women's clothing and cuckolding is similar to a hotwifing where she goes out on dates and fucks other men without her husband/boyfriend around but with cuckolding it...

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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...