Halloween Sissy Stories

12,071 results
Orientation
Length
Source
Infinite Scroll

Halloween Party Aftermath

by Sabnock on Oct 19, 2020
Transgender & Crossdressers

Oh my GOD I'm so hungover. I creak my eyes creak open, and immediately regret doing so. Everything hurts. My head is pounding. My mouth tastes like something died in it. I try to sit up, pause, flop back onto the couch. At least I've got blanket. Wait... I'm not in my bed. Where the fuck am I? I rub the back of my hand over my eyes, feeling a weird, heavy...

They're My Sisters Too!

by grgy56 on Sep 18, 2017
Transsexuals & Crossdressers

To recap, I sneaked into my sister's bedroom through the adjoining bathroom and dressed in some of her clothes. My best friend Chris caught me. He was shocked at first but then quickly recovered especially after I sucked him off and he exploded in my mouth. After a short recovery, he ended up fucking me in end. Then with Chris' cum dripping out of my ass ......

Revenge! Ch. 03

by Magnificat on Sep 19, 2017
Celebrities & Fan Fiction

Revenge is a dish best served hot; very hot! Pt. 3 (This is the third chapter in a series of six. Those of you who have read the first two chapters, know what you can expect. However the scenes depicted in this particular episode may not be to everybody’s taste. There’s BDSM, cuckolding, non-consent, anal rape and extreme violence so be warned! I recommend...

Insider Knowledge

by Athena_e19 on Sep 15, 2017
Erotic Horror

This is my submission for Halloween. It contents strong, violent content, and an incest theme. If this is not your cup of tea please move on. To those of you who stick around, I hope you enjoy it, and please remember to vote! Its what make this story count. * A long lean leg slipped from beneath the covers and dipped towards the floor. In the moonlight,...

Good Little Bitch Pt. 01

by Baron_Cumhausen on Sep 25, 2017
Transsexuals & Crossdressers

Chapter 1: Halloween "Seriously!" my girlfriend Claire declared, "Nothing faggy or anything like that, just yoga outfits and a little makeup, y'all will be so cute!" It was Halloween night in Austin, always a major event down on Sixth Street with ten thousand people bar hopping and mingling in the street even when it fell on a weeknight. Today was Friday...

How I Became a CD SLUT Cum Junky

by TonyaTV69 on Sep 12, 2017
Transsexuals & Crossdressers

Here I was all dressed up in a bright pink satin princess ball gown walking into an alterative dance club in Denver on Halloween night. My hair and make up were perfect and under my gown I had on a lace up corset holding some nice fake breasts, fine silk seamed stockings and some sexy black velvet ankle strap wedge six inch high heels. I made my way throug...

A Sissy's New Daddy Ch. 03

by sissyneko on Oct 8, 2019
Transgender & Crossdressers

I hope you enjoy this third chapter of "A Sissy's New Daddy" I hit a bit of a speed bump with this chapter, I wasn't sure where I wanted to go with it. I think I have that settled now. I am foreseeing this as a 9 chapter piece with the next three chapters jumping ahead a bit in time. I hope you enjoy this chapter, and if you haven't already please give the f...

Webcam Mistakes

by chrissycockslut on Apr 3, 2019
Transgender & Crossdressers

I guess I should've been more careful. But what can I say? I was a young man and I was stupid. I had just passed my 18th birthday a month earlier and I had treated myself to my very first, brand new dildo. Nothing crazy, only 5 or 6 inches long and just 1.5 inches girth with a suction cup base, but it was perfect for a beginner. Luckily, I had plenty of ti...

Just Look at Me Now Ch. 03

by GFfan on Apr 13, 2020
Transgender & Crossdressers

Eager as I am to tell you about my first crossdressed Halloween with Jude and Becky, I must save that for a later chapter and fill you in on some major developments that occurred as my first summer of feminization ripened into autumn. Surrounding these landmark events were patterns of submission we had established early on. I wore panties 24/7, and I shoppe...

The Writer's Secret Ch. 11-12

by AnnMichelle on Sep 16, 2017
Transsexuals & Crossdressers

Synopsis: Loren had no idea what he was getting into when his agent suggested he write transvestite fiction. Nor did he realize how eagerly his wife Stephanie would embrace the idea of feminizing her husband. How far would they go? * Chapter 11: Pierced Over the next two days, Loren got used to life as a sexy maid to a woman of whim. Stephanie got used t...