Halloween Sissy 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...

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...

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...

Halloween Problems

by Haley_Hazel on Oct 22, 2019
Fetish

Your not that old... So it makes sense you'd want to celebrate Halloween still as an adult. The thing is, you don't care about candy, and costumes, and spooky stuff. Nope, not you. YOUR into this holiday for the skimpy outfits, and parties... for the easy woman at those parties who are even better than candy! So as you walk downtown ignoring the kids in thei...

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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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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's life

by cdbaby on Apr 20, 2018
Fetish

INTRODUCTION: (sorry the way it was originally seemed unclear) Sissies, they're all over the world, and beyond. Discover their origins, their fears, their lusts.What's next? halloween vinny Messaging with a dream Trendsetting slumber pary Are you my Mummy? What's next? halloween vinny Messaging with a dream Trendsetting slumber pary Are you my Mummy?...

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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...