Halloween Crossdress Stories

5,980 results
Orientation
Length
Source
Infinite Scroll

The Third Apprentice

by wet_special on Sep 15, 2017
Illustrated

The Third Apprentice This is a Halloween story set in medieval times. It is heterosexual erotic horror, and it is illustrated. Here are the disclaimers: No one under the age of 18 is depicted. Themes include strong non-consent, age differences, big breasts, lactation, and mind control. It is historically inaccurate and un-researched. As a final warning, s...

The Magician's Assistant

by Penelope Street on Sep 25, 2017
Erotic Horror

Author's Note: I submitted this story within the Erotic Horror category for two reasons. First, there is at least one scene involving violence and bloodshed. Second, the explicit scenes are intended to be as disturbing as they are arousing, if not more so. Although there are several other possible categories, it is my hope that the majority of readers will...

Sharon Goes Back to School Ch. 14

by RogueAlan on Sep 19, 2017
Interracial Love

Original character by Nick Scipio Story continuation by RogueAlan Welcome back, readers! Apologies for the LONG delay. Chapter 14: Giving Thanks, Receiving Gifts "Morning, babe!" Sharon smiled and stretched beneath the covers, having felt the gentle kiss. "Morning, S-" her eyes snapped open... she had almost said 'Shaun.' She had not said it, had she?...

Flapper Dick Ch. 14

by emap on Sep 15, 2017
Novels and Novellas

I had been planning on ending this at thirteen, you know just say she died in childbirth or something. Except I couldn't do that, so many were saying that I had to keep going on this. In fact one of those is right... OH MY GOD, LOOK OUT BEHIND YOU. So I didn't get you to look, at least that is the lie that I will believe, and likely best to never admit to l...

Flapper Dick Ch. 13

by emap on Sep 15, 2017
Novels and Novellas

Oh no it's the unlucky thirteen, run for the hills. Still there? Dang it, I guess that means I will have to try harder. I will get you to run away, oh yes I will. I seem to have made this one a little long, so nine pages. So tempting to just keep typing stuff up here to stretch it to ten pages. I won't do that, at least not on purpose but maybe I can accide...

Two of a Kind

by StangStar06 on Sep 15, 2017
Loving Wives

Hi folks, please be forewarned. This is a very long story. I haven't written one of those in a while and i keep getting e-mails asking for them, so as fall approaches and we all have more inclination to sit down in front of the fire with a nice long read, I decided to indulge. Those of you who want a quick story with a lot of sex scenes should probably skip...

The Struggle Ch. 05a

by doberinca on Sep 14, 2017
Transsexuals & Crossdressers

Author's Note: This is the fifth story in the chain 'The struggle'. The story started with 'A game within a Game' part 1-2-3. It is divided into 2 parts (A and B). Again thanks to my editor NJLauren! Main characters: Rob - main character Helena - his wife Marion - widow; second 'wife' Cathy - friend (psychiatrist) Michelle - friend Kim - friend...

Cosplay

by Charles Petersunn on Sep 13, 2017
Fetish

This is the story of a girl with a fetish, inspired by the genre of cosplay within Japanese adult video idols. All of the characters in this story were at least 18 at the time of their actions. Finally, most importantly, my thanks to StoryPal for his considerable help in editing. - - - - - - - - - - - - - - - - - - - - Madeline Hemming was one of Dr. Lowe...

Dragons Breath Ch. 03

by acup on Sep 26, 2017
Romance

LEGALESE: Don't read this if you are underage, if it is illegal in your area, if it is offensive to you, or if you cannot distinguish fiction from reality. This is a work of fiction. All sexually active characters are above the age of consent on their planet of origin. Many thanks go to RF-Fast for editing and polishing. Any bad grammar left is wholly on m...

Organism X Ch. 07

by DevilBookCorruptions on Aug 21, 2019
Erotic Horror

Author's Notes: Well this was a doozy. By the end of it, this chapter is 119 pages. This seems excessive, but every time I tried to end the chapter, more material crept up. For the most part, I'm happy with the results. I won't spoil anything, but I will say that I moved the story along in a way that I feel keeps things interesting while still delivering...