Sissy Halloween Stories

12,071 results
Orientation
Length
Source
Infinite Scroll

Creating Ginger Ch. 03

by Ms_Allison on Jun 1, 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 consiste...

A New Spin on Role Playing Games Ch. 02

by shawnavinyltv on Nov 19, 2018
Transgender & Crossdressers

The next LARP event came by and I was more than ready! I was so horny and worked up I could hardly believe it. The last session had been such an amazing time and this one promised to be more of the same, and then added twist of me being the prize for one of the guys was just well, scary, but also a bit of fantasy come true! I did make sure to do all of my n...

The Vacation from Hell Pt. 03

by JamesMiehoff on Dec 11, 2018
Erotic Couplings

Copyright (c) 2018 James Miehoff, All Rights Reserved. This work may not be published whether for fee or free without this copyright. --------- This is one of a series of stories set in what I call Universe-J. Universe-J is very much like this universe with a few exceptions. First the people tend to be a little more sexual and less hung up on sex that...

Getting Nailed

by jbirdman on Sep 25, 2017
Fetish

This story is not intended for children and if you are not old enough to read sexually explicit material, go away. This story features some elements of female domination (femdom), cross-dressing (CD), mild bondage, Trangender (TG) and a few other fantasies of mine. I hope you find it entertaining, but if you might be offended, stop reading and do something e...

Aficionado Gets in Trouble Ch. 04

by His_fag_wife on Mar 17, 2020
Transgender & Crossdressers

Taryn told me to sit down, which I did with difficulty as I was only just getting used to breathing with the corset on. She knelt down in front of me, but this time it had no hint of submission. She was plainly completely in charge of me at this moment. She took the first shoe off, and prepared the first stocking, rolling it over her thumbs. I put my foot o...

Good Little Bitch Pt. 02

by Baron_Cumhausen on Sep 25, 2017
Transsexuals & Crossdressers

Author's Note: Many thanks to all who've voted, favorited, and commented on Part 1. Your kindness brought me great joy and inspiration. Below is Part 2 in gratitude. I hope you like it as much as the first one! If you haven't read Part 1, I urge you to do so before reading on. ***** Ben and I sat on the bench in the center of the apartment complex. The s...

Halloween Dress-up

by sirhugs on Sep 12, 2017
Transsexuals & Crossdressers

"Tim, can you please come on over? I have to go to a party later, and I'm already dressed in costume." "Why are you dressed up so early?" "I had to take my little brother Teddy trick or treating. But now my parents have taken him to a party at the club." Even though I was a guy, and she obviously wasn't, Sally Brown was my best friend, and had been since...

Don Venuto's Sissies

by marybethsanford on Aug 18, 2017
Fetish

Players: Capo De Matzo, counsel to Don Venuto. Don Venuto also known as the Godfather; Mario Venuto, son of Don Venuto; Ms. Rosa Cappella, professional dominatrix; Carol Evans, mother of Mark Evans; Mark Evans aka Martha Evans; Helen Andrews owner of the Little Miss Muffin Boutique; Ralph Summers, a friend of Mark, aka Robin; Steve Franks, friend of Mark, ak...

Halloween Party

by cuck2serveU on Nov 26, 2017
Interracial Love

Trish and Brent hosted the Halloween bash this year. Once again Jennie was still busy with her new vanilla man so she opted to send a replacement for me to service. Once again it would be a surprise because that's how she rolls. As always, this party is the most expensive of the year because it's held at a hotel in Vegas and there is an entry fee for all cou...

Cindy's Slut Ch. 15

by Bastinado on Sep 15, 2017
BDSM

CH 15 KNOCKING KNOCKOUT I was just about 1/2 way through my third set on the bench press when her legs appeared above my head. She was wearing short-shorts. The legs of her shorts flared just enough that I could see all the way up to her crotch. A glimmer of a small white satin thong was just visible up between her legs. Her midsection was bare, with her 1/...