Crossdresser Proper Lady Stories

104,639 results
Orientation
Length
Source
Infinite Scroll

Sissy in The Hart of the Valley

by EvelynT on Sep 16, 2017
Transsexuals & Crossdressers

The story so far; having completed the first date with Harold Plumrose and with over a month until the scheduled second date Sissy Betty Blane spends time at a t-girl club with Cindy. ***** When I got home from the Hollywood Hills I barely had the strength to remove my makeup. I was so exhausted I just wanted to flop on the bed and pass out, but I persever...

From a Husband to a Dutiful Sissy Ch. 01

by Sissy_Chantel on Sep 25, 2017
Transsexuals & Crossdressers

Preface: Welcome to my next sissy story. This one is based around the exciting ideal of a married sissy, crossdresser. It will have many ideas based on my thoughts about how life could be for me as a married, crossdressing sissy maid. I hope you all enjoy it. ***** Chapter One: Sometimes one's most unique secrets do come out. My name is Phil and I've alwa...

Career Shift

by tgirl_Mary on Sep 13, 2017
Transsexuals & Crossdressers

Receptions are not my favourite things in the world to attend. I don't mingle and 'rub elbows' like agents and sales people do. I usually end up at the bar drinking alone, looking at all the phoney people. I am a writer, a sports column writer more specifically. The magazine that I write for is one of the biggest national publications with a huge male reader...

Martin's Halloween Nightmare

by rik581 on Sep 16, 2017
Transsexuals & Crossdressers

Martin's Halloween Nightmare is a short side story using the characters and world of Martin Hastings. An unusual story to say the least. Not for the squeamish. It is not part of the saga itself. ***** "Twisted" Martin sat at the table before the judge with his legal counsel. The courtroom was full of spectators as the drama of the judge's decision loomed...

Life and Time of Lady Vargos Ch. 07

by rik581 on Mar 26, 2019
Transgender & Crossdressers

"The New Bitch of Vargos Manor" Written by: Rikki Lady Vargos begins to exert his new found powers as Lady of the House. He is able to channel many of his frustrations and anger through being tough and almost insulting to those try to accept him as the Baron's wife. As a result, word spreads and Martin is slowly becoming the Bitch of Vargos Manner. "Thank...

A Crack in Reality

by Mr Nice Guy on Aug 20, 2018
Miscellaneous

Something is wrong. There is a crack in reality! Things are changing! Is it human made? Has it always been there? Is someone controlling it? Is there any way to stop it?!What's next? Average Office Worker Alex William Borgman, Mad Scientist Rachel Davis, College Lesbian Goth Girl Daniel, average thief Jason Willows, struggling middle class family member. M...

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The New Neighbour

by seams_straight2me on Sep 14, 2017
Transsexuals & Crossdressers

It was the most exhilarating and exciting sound ever. My first outing dressed up and made up, and the ticking of my stiletto heels on the pavement made me feel alive, sexy, feminine and horny. The nylons with seams as straight as you could wish to see them felt even sexier and better than I wore them indoors. The soft breeze over my smooth legs felt lovely,...

Learning to Crossdress Pt. 01

by crossdressme70 on Sep 15, 2017
Mature

I am a "Closet-Crossdresser" - something my wife would not accept, but a secret I indulge in whenever she is out of the house for a while. This is my story of how a beautiful older lady, who had a "fetish" for lipstick, nylons, high heels, and lingerie, introduced me to the pleasures. It was the late-1980's, we had just moved from a small town in the UK, t...

Gender Bent Society

by turtlerocker on Sep 26, 2017
Fetish

Welcome to GenericVill! A small town in a world that has the opposite gender norms of our society. Some changes from our society is that it is a matriarchy, Girls are considered more athletic, Boys are considered nicer and more emotional, Boys wear what our world's girls would wear, and vice versa, and most importantly, Boys are submissive while Girls are do...

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Weekend Games Ch. 03

by SissyAndi on Sep 16, 2017
Transsexuals & Crossdressers

Disclaimer: My stories contain explicit descriptions of consensual and Non-Consensual sexual activities and are not suitable for reading by anyone under the age of 18, or anyone offended by reading such material. These acts include bisexual activity, cross-dressing and other fetishes and perversions. All characters and events are complete and total fiction a...