Crossdresser Proper Lady Stories

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My Little Adventure

by CorsetCutie69 on Sep 13, 2017
Transsexuals & Crossdressers

Let me start by saying that I have been crossdressing for over 20 years and I didn't really feel like a lady until just last week. I should rewind about 3 weeks so that I can explain what happened leading up to my little adventure. I frequently shop at several local lingerie stores and adult boutiques. Three weeks ago I went into one of my favorites. A nice...

My "Uncle" Caught Me in Pantyhose! Pt. 06

by JHouston on Sep 16, 2017
Transsexuals & Crossdressers

"You will make a hot little sissy in those heels and dress." said a man's deep voice behind me. I was startled. I was shopping alone in a boutique and adult novelty store near my new rented apartment. I had just moved in two weeks ago to be closer to my new college, and, I was picking out a few sexy outfits for crossdressing fun. I turned around to see a t...

Neighbor to Lover Pt. 01

by sarahchica96 on Oct 2, 2018
Transsexuals & Crossdressers

Introduction It was the summer I (Alex) and my twin sister Gina graduated from Business school, ironically Gina and I joined our family real estate business. This was a way of our parents keeping us busy and stop our procrastination about searching for jobs elsewhere. It was also the time my crossdressing persona met our neighbour Mr Parker. Backstory......

Crossdresser In Picnic Area

by Lovinhose on Sep 13, 2017
Transsexuals & Crossdressers

This is my first attempt at a fictional/fantasy story. All my stories thus far have been true, honest, and accurate, as much so as I can recall. But I kind of ran out of true stories that were worth sharing (for now, but I've got some 'irons in the fire' and hopefully I'll have another true story to share fairly soon). The story I will tell here is something...

Sarah was a Bad Girl

by SarahCD on Jan 8, 2019
Transgender & Crossdressers

I first published this experience a few years ago. I prefer to call them 'experiences' since the term 'story' implies fiction to me. My experiences are based upon my real life. Since I started posting my experiences my writing skills have improved a little. While, I cannot change what actually happened to me, I have added some more details and corrected some...

From a Husband to a Dutiful Sissy Ch. 02

by Sissy_Chantel on Sep 18, 2017
Transsexuals & Crossdressers

Chapter Two: My reveal, a true reveal for the sissy in me. I reach to the bottom of the stairs and at the front doorway entrance, Helen and Jenny are standing and looking at me in my black maids dress, white tights, black velvet 5 inch spike heel pumps, wig and makeup. The look on their faces seeing me dressed as such is priceless. This is the first time He...

The Glass Door

by JackOLantern on Oct 16, 2018
Fantasy

((Author's note: I have made this story open to the public. I encourage people to post their own chapters and threads. If you are a potential writer want an idea of how the mirror works, read the first handful of chapters in my main thread to get an idea. You are under no obligation to make it function in the same way unless you want to, however. Have fun wi...

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Home Again

by PeggyBuxton on Mar 6, 2018
Fetish

The senior year at the university was over at last. Tom had already broken up with Carrie. She was his mother's age and married. It wouldn't have lasted no matter how good the sex was. There had been two others before her, both similar ages, both married. He was handsome and could have had his pick of beautiful coeds. They never seemed to offer the same exci...

Sex Ed

by britneyfan on Sep 13, 2017
Transsexuals & Crossdressers

My husband and I had quite an open marriage. We were both fairly sexually adventurous and this was reflected in how we both considered it to be ok for us to be going out and sleeping around provided we were completely honest about it and came home and told the other one all about it. In fact, after a while, we found that this recounting of our bedroom exploi...

Ugly Duckling to Sissy Princess

by JHouston on Sep 18, 2017
Transsexuals & Crossdressers

All names have been changed to protect the guilty. ***** Being a very short guy (5'3") with a small frame has been a major handicap in my quest for female companionship. Having a micro penis was the nail in my coffin. Throughout my youth, I was ignored or rejected by girls. I had my first girlfriend in college, Caroline Fletcher. She was smart, beautiful,...