First Time Crossdressing Stories

351,059 results
Orientation
Length
Source
Infinite Scroll

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...

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

Lipgloss Dreams Ch. 01

by lipglossdreams on Sep 12, 2017
Transsexuals & Crossdressers

I suppose that my story starts in the same way as a lot of other crossdressing boys with busy real lives: year after year of bottling things up, slowly buying clothes, dressing furtively, shamefully, until things would get too serious with a girl, then - a fearful, hurried purge, a headlong plunge into the cold waters or normalcy. What a deceitful plunge it...

Home in the Hills Pt. 01

by ValoryG on Dec 10, 2019
Transgender & Crossdressers

All names and characters in this story are fictional and have no connection with any actual person living or dead. ***** Jonathon Worley is in his sophomore year at Onanoma State University, majoring - at least for the time being - in art history. He's the third child in his family, and after his parents paid for the first two to go to college, there was...

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....

Jolene's Momma Pt. 01

by ValoryG on Jul 27, 2020
Transgender & Crossdressers

(The names and locations in this story are completely fictional and have no connection with any person living or dead.) My name's Chris. Wife Jolene and I have been married six years now. Live in the small city of Centertown, Ohio. It probably got that name because it's about half way between Columbus and Cincinnati. Being from a midwestern small town, the...

Life and Time of Lady Vargos Ch. 18

by rik581 on May 21, 2019
Transgender & Crossdressers

Chapter 18 "Changes upon Changes" Martin rolled over on his side hugging his pillow trying desperately to fall asleep. Though the curlers that Leanne had tightly wound in his hair for the night were very uncomfortable and trying to position his head to sleep in them was exhausting, it was the events of the day weighed heavily on his mind and kept him awake...

Stacy and Matt

by mattpantyhose on Jan 28, 2020
Fetish

Matt's bliss ended almost as soon as it had begun. The girl he had met and who not only was pretty and smart, but also enjoyed his crossdressing decided that career was her priority after merely few weeks of their relationship; the two broke up as she moved to a different distant city. Matt still had a good job, amazing boss and sympathetic co-workers, but d...

Best Camping Trip Ever Ch. 04

by Lovinhose on Sep 16, 2017
Transsexuals & Crossdressers

*This is a work of fiction. Most of my stories are true, but I do have unrealized fantasies...that I'll try to make reality...hope you enjoy!* *Note-this is part four of my story entitled 'Best camping trip ever for CD'...if you haven't read the first three parts, or at least part two and three, you won't understand what's going on at first. I don't like to...

Caught en Femme

by RisqueRavisher on Sep 12, 2017
Transsexuals & Crossdressers

This is the very first story I've written and uploaded here. I'm sort of nervous because it's probably not the best. Don't forget to rate and whatnot. Give me feedback/tips on things to improve on. I'm always looking to improve. Anyway, enjoy xx ***** "I'm going to be home a little bit later, babe," my wife, Annie, called from the alcove. "I'm going out wi...