Crossdresser First Time Stories

351,031 results
Orientation
Length
Source
Infinite Scroll

Literotica Monthly Awards 2020: July

by Literotica on Oct 5, 2020
Loving Wives

Manu and I would like to thank all the authors who submitted during the month, and all the other months for that matter! We've tallied the reader's votes, and are happy to announce the winners of July's Reader's Choice Awards. First Place ($150 Cash Prize Winner):S'mores Ch. 04 - Forever Please by BookwormmomSecond Place ($100 Cash Prize Winner):Home for Ho...

Crossdressing, Piss and Sex

by Lovinhose on Apr 14, 2020
Transgender & Crossdressers

This is a work of fiction, a fantasy that I would love to come true. It also contains 'pissing' (aka 'watersports'), crossdressing, and a crossdressers sex with men, so if you are not into these subjects, this story might not be for you, you have been warned. Also, comments are welcome, but please note, I'm NOT a professional writer, if I was, I wouldn't be...

Literotica Monthly Awards 2020: January

by Literotica on Jul 14, 2020
Mature

Manu and I would like to thank all the authors who submitted during the month, and all the other months for that matter! We've tallied the reader's votes, and are happy to announce the winners of January's Reader's Choice Awards. First Place ($150 Cash Prize Winner):Home for Horny Monsters Ch. 49 by writerannabelleSecond Place ($100 Cash Prize Winner):Sound...

Literotica Monthly Awards 2020: March

by Literotica on Jul 14, 2020
Exhibitionist & Voyeur

Manu and I would like to thank all the authors who submitted during the month, and all the other months for that matter! We've tallied the reader's votes, and are happy to announce the winners of March Reader's Choice Awards. First Place ($150 Cash Prize Winner):When Angels Cum Ch. 19 by CapDragon121Second Place ($100 Cash Prize Winner):Chasing The Last Roa...

Perfection

by ValoryG on Apr 23, 2019
Transgender & Crossdressers

It all starts, innocently enough, when Joanna's looking for a dresser. On one hand, she can just go to a big box furniture retailer and get an inexpensive, functional one that looks decent (and build it, of course). Or, she can browse around online and find a new or used one with a more elegant pedigree. Joanna, by the way, is a very practical, elementary s...

A Sissy Story

by PinkRebecca on Feb 21, 2020
Fetish

You always were a normal boy growing up, weren't you? Played some sports, although not to an extent where you stood out anywhere or made any teams. You had a normal friend group, as far as you knew atleast. You liked girls, like most of the boys around you, although you lacked the curage to talk to them. Well not to talk to girls in general but in a romantic...

Open in Reader

Bra Zen

by ValoryG on Jul 10, 2019
Transgender & Crossdressers

Millions of women are familiar with the Bobby Braxton brand of bras (BBBB), one of the brands under the corporate ownership of Simone International. Where Simone's bras from all its lines cover the spectrum from teen training bras to 48DD harnesses, the Bobby Braxton line, Simone's most expensive, specializes in sexy, fancy, often elaborate brassieres rang...

Second life of Emily

by Alexia Wright on Jun 3, 2015
Fetish

I have always wanted to get fucked by another man. Being 5'6" and weighing little over 60 kilos, my effeminite and near hairless body bore no signs of an able bodied alpha male, so i decided to explore my inner girl since my mother and sister are the only people i live with. It started with simple things, like my sister's school clothes, then her under...

Open in Reader

A Sissy in the 22nd Century

by JerkGently on Jul 1, 2020
Transsexual

In a future not too far flung, humanity has progressed to a stage where almost all production and provision of society’s needs is automated. With no need to work, all citizens are instead driven to find lifestyles that fulfil their own and each other’s fundamental desires. This is achieved by the medium of an overruling system of artificial intelligences and...

Open in Reader

Craigslist CD Hookup

by Lovinhose on Sep 16, 2017
Transsexuals & Crossdressers

I have been crossdressing since I was a kid. I started out with a pair of my mother's pantyhose, as most other crossdressers start out the same way. Once you get bit by the bug, you're hooked. This is my first story, but I have so much to tell that this certainly won't be my last. All of what I tell you here will be 100% true. I will not dramatize or sensati...