Crossdresser Wife Stories

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Crossdresser Evolution Ch. 02

by pantyhigh on Apr 8, 2019
Transgender & Crossdressers

Recap - Crossdresser Evolution - Ch 01 - How I got started crossdressing I was becoming addicted to this new way of masturbating very quickly, though there was still this feeling of shame surrounding it. I made sure I deleted the browsing history and then went to the bathroom to clean up. There I saw myself in these cum soaked pink panties. I could feel som...

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......

The Ride of a Lifetime

by CuriousJ95 on Nov 6, 2018
Transgender & Crossdressers

Hi everyone, this is my first attempt at writing. I hope you enjoy and I can't wait to get some feedback from everyone. Please be honest in what you think...I can take it. This is a true fantasy of mine. *** I'm a curious man that is married to a wonderful woman but as time has passed our sex life has diminished quite a bit. We still occasionally enjoy...

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...

My First Time CD Sex

by Lovinhose on Sep 16, 2017
Transsexuals & Crossdressers

When I posted my first story, about my most recent experience, I promised to follow up with other stories, including my first time sex as a crossdresser. So here it is. This is the story of my very first time. As I said in my first story, MY stories are totally real, they really happened and happened just as I describe. Nothing at all is made up. I am very l...

Sissy Boi

by DrLuverotica on Sep 12, 2017
Transsexuals & Crossdressers

COFFEE "Thanks for me, Raquel, I'm at the end of my tether and I don't know what to do with Dan anymore." I was meeting Raquel, one of my colleagues for coffee. She knew I was struggling with my husband, but didn't know the problem was in the bedroom. "That's alright, Jo. My pleasure." "Look what I've got to share with you is deeply embarrassing, so I beg...

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...

Evolving Sex Life Pt. 02

by slavecaro on Aug 31, 2020
BDSM

The following Sunday my wife woke me up telling me she needed a new pair of shoes. This has always been code for sex. We began kissing and after several minutes of foreplay, I rolled on top of her and tried to enter her. She pushed me and said, "No, please eat me." I slid down the bed and between her legs. Sometimes she can quickly get to an orgasm and this...

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,...

Dressed for Disaster: The Sequel

by thrillerauthor on Sep 14, 2017
Transsexuals & Crossdressers

FORWARD: This is the third of five episodes of the Dressed for Disaster saga, immediately preceding “Vendetta’s Diary.” Patrick Summers wandered the streets of lower Manhattan in an aimless fog, the chaos surrounding him a lurid backdrop for the turmoil between his ears. He had just suffered two tremendous shocks: his narrow escape from the collapse of the...