Sissy Halloween Stories

12,071 results
Orientation
Length
Source
Infinite Scroll

A New Spin on Role Playing Games

by shawnavinyltv on Sep 18, 2017
Transsexuals & Crossdressers

I've always been something of a geek. I love sci-fi and fantasy books and movies; I can recite countless bits of useless trivia back to you about all kinds of movies. So, it was no real surprise that I took to role-playing games, or RPGs, as we like to call them. You know the kinds, Dungeons and Whatnots, all that kind of Tolkien-esque stuff. I had a couple...

Virtual maze

by Sgtwolf on Dec 20, 2019
BDSM

It’s finally here! You scrimped and saved, and the most hyped technological breakthrough in years is finally yours! You open the package and pull out the black spandex full body suit, almost midnight in color except for the neon blue thick line running down the body and each limb. The Virtual Integrated Suit System, or VISS, claimed to be able to perfectly r...

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Amy's Coming Out Party

by Cyndi44 on Sep 16, 2017
Transsexuals & Crossdressers

"What are you going to be for my Halloween party?" A simple question, really, but one I had been avoiding. My friend and co-worker, Jackie stared at me as she waited for the answer. "You know, when I was a kid, I loved dressing up for Halloween. Free candy and all that. Now. I am a 35-year-old man. Who wants to see me dressed up as Superman or Batman. No...

It All Started When...

by crashmatt on Oct 24, 2018
Transgender & Crossdressers

It all started when... well, perhaps that's not a great way to start. It's difficult to say exactly when it started, or perhaps even what "it" is. For the purposes of this story "it" relates to an episode at Halloween, yes I know, another Halloween story. But, you see, in the UK Halloween isn't the event that it is in the USA, and crossdressing for Halloween...

Seven Lessons Ch. 02

by Vertex on Sep 16, 2017
Transsexuals & Crossdressers

Previously... Bryan is an arrogant biggot. This Halloween season, someone has decided to teach him a series of 7 lessons. Yesterday the lesson was acceptance, but as he chose not to accept the lesson, he ended up with no body hair, wearing a bodystocking and being fitted with a chastity device. Will he learn his remaining lessons? That night he had many...

The Cause

by desireethtttv on Sep 16, 2017
Transsexuals & Crossdressers

Often I've wondered why the only thought to stir my sissy cock, some 40 years into life, is the vision of a hard, throbbing, blue veined cock arched just before my eager lips. Was it the spiked heels I pranced around the house in younger years or perhaps the love for the pale yellow slip I stole from my sister and wore secretly under my jeans and shirt while...

Tell Me what You were Thinking Ch. 03

by trixie_leigh on Dec 17, 2017
Transsexuals & Crossdressers

I'm on my knees. It's Halloween. We're at a party. I'm dressed like a slut. Which, I guess I am, since I'm on my knees. Giving blowjobs. It was only supposed to be one. You said a friend of yours from work would help me live out "my fantasy". Really, it's your fantasy for me. My fantasy is much simpler. You let me dress in panties and sleep in lingerie. And...

Who Killed Jenny Schecter? Ch. Adden. 1

by OGSalli on Jul 15, 2020
Humor & Satire

DJ La Pica (Carmen Morales) broadcast her first Top 10 Lesbian Country and Western Tunes list near the end of Chapter 34 of Who Killed Jenny Schecter (see below in case you missed them). Without further ado: "Good afternoooooon, San Francisco! This is your besty former convict galpal, Alice Pieszecki, broadcasting live from the Tower of Power here at Stati...

Creating Ginger Ch. 01

by Ms_Allison on May 12, 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 cuckoldry, dominance and submission. If these are not topics you are interested in, then please move along. In the below story I refer to the male character several ways but try to maintain a consisten...

Cornholed

by LaBlancheTraversee on Sep 11, 2017
Fetish

I'm in Tori's basement - tied to a chair, blindfolded, naked and gagged. My hands are cuffed behind me and my rock-hard cock is locked in the plastic cup of a chastity belt, engorged and aching for the feel of her delicate skin. Fantasies of her jacking me off with her hand send a jolt of electricity rushing down to my cock as thoughts of our earlier phone c...