Sissy Crossdresser Stories

7,061 results
Orientation
Length
Source
Infinite Scroll

Suspected Affair

by 69Jance on Apr 21, 2020
Transgender & Crossdressers

I had suspected for a while but recently found confirmation, not that I would blame her. I know we loved each other but I also knew there were needs the other could not fill. I found evidence she was having that need I could not meet, met by someone else. I was a bit jealous but in a strange way. There was no anger but a bit of arousal as I imagined her love...

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...

Sissy Walk of Shame

by zona_loser on Mar 12, 2019
Transgender & Crossdressers

First off: This is a story about my alter ego a not so bright crossdresser who likes a bit of exposure. It also contains an element of self-bondage but not in the traditional manner. All characters are over 18 years of age and are purely a figment of my imagination. ***** I am a part time mostly closet crossdresser. I don't consider myself gay or bi and ha...

Sarah Helps Clean Out a Garage

by SarahCD on Mar 11, 2019
Transgender & Crossdressers

A friend of mine, Sandy, asked me if I would come over next Saturday and help her clean-out her garage. I had known her for several years and her husband had just left her and so, when she asked me for help, I could hardly refuse. In addition, she is cute and I cannot imagine why her husband would leave her. On Saturday, I went to her house. I only ever we...

From a Husband to a Dutiful Sissy Ch. 17

by Sissy_Chantel on Sep 25, 2017
Transsexuals & Crossdressers

Chapter Seventeen: Wedding Day and Wedding Night. [November 16.] Life is all a hectic fluster, now one day prior to the wedding of Mikel and myself along with Helen and Alan. Crazy, crazy, crazy, but so exciting... I finally find some time to be with myself. I am in the bathroom, naked only my pink fluffy bathrobe on. I'm going to take time to just sit an...

Sissy Crossdresser Needs to Please

by Interested4L8R on Dec 11, 2018
Transgender & Crossdressers

My wife is out shopping. I have just a couple of hours to indulge my fantasy before she returns. Yes, that fantasy. The same fantasy you have. The one in which I open my wife's closet and decide what clothing of hers I'm going to wear. I want to dress up. I want to dress up for you. And my little smooth, shaved cock is quivering in anticipation. What will I...

The Woman Next Door Pt. 01: We Begin

by jableabee on Mar 9, 2020
Transgender & Crossdressers

Do not ever doubt that your life can change in a moment. Mine did. And oh so much for the better. All it took was a knock on the door. On Saturday mornings I take care of my chores: some cleaning, the laundry, shopping, the usual tasks. I'm generally done by noon and then it's time to transform myself into "Barbara", my feminine self. I'll shower, shave, do...

A Panty Boy Confession Ch. 01

by Creativekink on Sep 13, 2017
BDSM

When I moved to Connecticut for a new job, I knew I wouldn't have a lot of friends right away. That was not out of shyness, it was just to be expected with being in a new town. Thankfully my neighbors were very friendly. I was in mid-20s when I moved into the small apartment complex in Danbury. Since it was late in the summer, I made sure to cook outside as...

Discounted Carpet

by Leigh_216 on Jul 31, 2019
Transgender & Crossdressers

My name is Leigh. Well my girl name, I am a cross-dresser. I just feel right to me and I guess that is how I am. All my stories are based on truth; but the places and names have been changed. Friday night and I was ready to hits this clubs but I needed to stop at my Aunt's old house on the east side of town first. Long story short: The family was selling it...

Sarah's Sister-in-law

by SarahCD on Jun 11, 2019
Transgender & Crossdressers

Editor's note: this story contains scenes of incest or incest content. ***** 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...