Sissy Halloween Stories Stories

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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...

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...

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...

He Changed Me

by Sissyhalo1 on Dec 23, 2019
Transgender & Crossdressers

I know a lot of these stories are about some guy that watched porn or read it and got hooked or were some short femmy guy that got tricked into getting boned but that's not me. I'm Sam and yeah it's Samantha most of the time now. But before that it was just Sam and I was in my last year in college and to save money to fix my car I moved into a rental house...

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...

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 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:...

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...

Connie Goes to College Ch. 03

by cmorehead on Sep 16, 2017
Transsexuals & Crossdressers

Disclaimer: The following story is not intended for minors. If you are offended by sexually explicit material or it is not legal in your place of residence, please close the document now. If not, I hope you enjoy my attempt at entertaining you with stories of my adventures. In my last chapter, Jeff and I had just made love for the very first time and I w...

Panty Posers Ch. 05

by EROTICbearscribe on Oct 5, 2020
Transgender & Crossdressers

I certainly wasn't in Kansas. I was dressed as a private school girl tease and standing in front of an adult bookstore superstore. What did my sissy sister have in mind? I tried to find some sort of hint but his poker face offered no clues. We were certainly dressed for more than just shopping for DVD's. So I didn't think we were there for the sales. We ha...