Halloween Crossdressing Stories

6,808 results
Orientation
Length
Source
Infinite Scroll

Bound Friends Pt. 02

by jessbbaby34 on Sep 11, 2017
BDSM

Part 2 - Andrea and the FetFair There is an old saying that you can't unring a bell. It may be a cliche, but it also happened to be true. For Andrea that bell had been rung two nights ago. She had discovered a side of her she didn't know existed. A kinky side. And even as the cheap beer flowed and the music pumped in her house full of guests, she found...

Maria's Misconceptions

by gabapentin on Sep 13, 2017
Loving Wives

Like my first story, this comes from people that I've known throughout my life. This one hits a little more towards home tho, it's based on true events. I incorporated some of the people from my first story, because they all knew each other anyway. None of the names of the characters are real, nor are most of the places of business (a few that had no real si...

Golden Buns

by MrKnightlyWriter on May 22, 2019
NonHuman

It was a cold night Cole said to himself as he walked home from work he should have brought his coat, but he stupidly thought that his jacket would be enough besides it was only a ten-minute walk to his boring old home, well it technical wasn't his it was his parent's home, well one of their homes it was a small two floor home simple upstairs, ground floor a...

SEFCC 01: Swedish Erotica Club

by StretchTacos on May 12, 2020
Novels and Novellas

Swedish Erotica Film Critics Club Chapter 01 - Swedish Erotica Club Midway City CA - Apr 1, 1983 What happens after school's out, stays out of school. Erotic Couplings, First Time, Novels and Novellas, Romance, Exhibitionist and Voyeur Copyright 2019 -- StretchTacos All rights reserved, including the right to reproduce this story or portions thereof in...

Life after the Lottery Ch. 66

by drmac100 on Dec 24, 2019
Novels and Novellas

Copyright LATL, 2019. No part of this shall be reproduced or re-posted on any other website. It is for the exclusive use of Literotica.com. Life after the Lottery, CH 66 Upcoming business meeting We all slept in on Sunday. We had been up late, having sex. The girls were all teasing me about the fake porn video they set up. Samantha and Amy kept at it unti...

Girls Wear Swimsuits, Boys Go Nude

by Totzman on Jul 6, 2020
Exhibitionist & Voyeur

Monica Kelly tapped her fingernails nervously on the chair's armrest. She had her nylon-covered legs crossed tightly while she watched the bustling activity of the office workers passing by; mail clerks, secretaries, and sales managers all with somewhere they needed to be. Monica glanced out the window and watched the busy traffic on the streets four storie...

A Shepherd Afield Pt. 05

by BurntRedstone on Oct 7, 2019
Erotic Couplings

Author's Notes: 'A Shepherd Afield' is a continuation of 'A Shepherd in France' which continued the story of 'The Shepherd of Ashburn Court'. Minimal effort is made in this tale to explain the backstory so please read the other stories first. All characters engaging in sexual relationships or activities are 18 years old or older. ******** Chapter 36...

It?s Either Break Up Or Make Up

by felicia_rene on Sep 12, 2017
Transsexuals & Crossdressers

PART 1 Synopsis: I always was put off by the unsuspecting stupid love sick, pussy whipped guy is transformed against his will because the will wants to run off and have an affair, I never understood why they don't just pack and leave. The underlying theme is transformation and sexual punishment of the main character with anti gay womanizing feeling for hi...

The School Tramp

by tawnysuede on Sep 19, 2017
Transsexuals & Crossdressers

(From "Boy" to " Boy oh Boy!!") Chapter 1 - The School Tramp I was a virgin. I did not want to be a virgin. I asked my sister for help, and that was a mistake. Well, at the time I thought it was a mistake, but it turned out to be the best mistake that I ever made. I was nineteen years old at the time and entering my junior year of high school. Yes, my ju...

Murder Misstery

by thrillerauthor on Sep 16, 2017
Novels and Novellas

(c) 2009 by Thrillerauthor When I rolled out of bed that fateful morning, I had no way of knowing that it would be my last day as Matt McCoy. After showering and dressing quickly (how I long for those days!) I bolted out the door for my train, looking forward to another manic day on the floor. Although I was one of the youngest traders at the Chicago exchan...