Crossdressing Halloween Stories

6,808 results
Orientation
Length
Source
Infinite Scroll

Futa,furry and fetishes

by itthatlurks on Nov 18, 2018
Fetish

Welcome to the story, please choose a character. The world building will soon comence tomorrow as I am more interested in where the story goes first. So please be patient with me as this is my first story. For now if you want some of the concept then look to the synopsis. I have returned to the story after several months break and shall be, hopefully, postin...

Open in Reader

Alex Struggles to Accept who He Is

by Shy_n_bi on Jul 29, 2019
Transgender & Crossdressers

Alex never thought he'd be living in this moment, a desire that he kept buried ‎deep within for his entire life and now a near reality! His eyes locked on her every move as his heart raced like he had never felt it race before and the battle between pleasure and guilt had all but began leading from his mind to the pit of his stomach! There he was, nervousl...

Driving Home - Getting Braver

by GeorgiaD on Jul 9, 2019
Transgender & Crossdressers

After my experiences meeting Steve on my way home (see Driving Home), I decided it was time for me to become braver, or rather less fearful of being out in public. Meeting Steve had exposed me to face to face contact with not only another actual human being, but a real guy, for the first time ever. I concluded that it had been Steve's patient, cool manner t...

A Humiliated Tomboy

by humiliationstation on Feb 19, 2020
Exhibitionist & Voyeur

Alex sat on her bed, playing video games. She was a cute high school senior in a baggy hoodie and basketball shorts, her orange hair cropped at her shoulders. She was sucking at her braces in concentration when she was interrupted by a knock on her bedroom door.What's next? Claire, her bully Her best friends Nate and Jane What's next? Claire, her bully H...

Open in Reader

Just Look at Me Now Ch. 02

by GFfan on Mar 2, 2020
Transgender & Crossdressers

When I arrived at my first scheduled play date with the kinky lesbians Jude and Becky, I was extremely well prepared logistically. I had triple-checked the items I'd been instructed to bring and completed all my assigned tasks, including shaving my legs. Emotionally and psychologically, however, I was shakier. I had loved the impromptu feminization we had in...

This to Keep Me Quiet Ch. 01

by MicheleNylons on Oct 5, 2020
Transgender & Crossdressers

Chapter One - It's Not Right Uncle John, For All Sorts of Reasons Author's Note: This is a little two-part tale similar to my early stories. It has all the trappings of a Michelle Nylons story: a little incest, a little blackmail, a lot of sex and a surprising ending. I hope you like it. Crystal Palace sat at the bar watching Melanie Starr singing The Cryi...

Gender Change: Magic Closet

by Zekar on Jan 26, 2017
Fantasy

There is magic in the world. Narnia was just the tip of the iceberg when it comes to the magic that a wardrobe or closet can do. You find yourself directly in the crosshairs of such a magical encounter. Whether malicious or benevolent, that is up to you... This is merely the introduction to a much more interesting tale. (Dear reader, if you like this story a...

Open in Reader

Anime ENT

by akikuka on May 16, 2019
Exhibitionist & Voyeur

They always confused people around them of their true genders as their appearance and figure contrast their true physical self regardless of their claim. It doesn't help that most of them wear female clothing to further add our confusion(and our sexuality). They are called Traps, or Tomgirls if you will. Having the beauty that brings girls to shame, these tr...

Open in Reader

The Slut Couple

by kin1041 on Sep 30, 2019
Swinging

The Slut Couple is inspired by the cover art (made by Chromosomefarm from Hentai Foundry). The idea of a slut couple was interesting and I liked the idea of couples getting into sexy situations but coming out of it still together if not a little twisted at the end. Something like borderline netorare and such. So before we begin; who's the couple?What's next?...

Open in Reader

My Neighbor's Submissive Ch. 01

by marissacd on Nov 27, 2018
Transgender & Crossdressers

Chapter 1 - Exposure They moved in next door shortly after we bought our house about five years ago, a nice couple who were a few years older than my wife and me. My name is Michael. I'm twenty-eight years old, white, five-seven, brown hair, blue eyes and a lean build, suitable for cycling, which I do a lot. My wife, is five-four, slim, athletic and blonde....