Crossdresser Chastity Stories

7,593 results
Orientation
Length
Source
Infinite Scroll

Diary of a Panty Lover's Wife Ch. 02

by xd_hubby on Apr 24, 2018
Fetish

10 days. That seems to be about the right amount of time. If I can convince my husband to hold off orgasm for 10 days, I can get him to do just about anything I want. I don't necessarily get off on making my husband do things--I'm no dominatrix. I just like sex. But I've learned over time that to get the sex I want, I have to play into his fantasies a bit....

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...

Sarah has Sex at a Nudist Beach

by SarahCD on Jun 4, 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 detail and corrected some...

Recruiting of a Sissy Maid Ch. 01

by Sissy_Chantel on Oct 11, 2017
Transsexuals & Crossdressers

[Welcome to my next story. This story has become a little different in how I planned to write it as compared to my previous stories. It has been fully written up already, as of this first uploaded chapter. Doing it this way allows me to better proof read and adjust for future chapters before uploading each. I will submit uploads on a regular basis for my rea...

A Surprise Relationship

by canuckCD on Sep 13, 2017
Transsexuals & Crossdressers

This is a fictional story, although it is based on people I did know. "Tony" and his twin sister "Kim" are based on a set of twins I knew, who were almost identical. I did have a relationship with "Kim" for almost two years, however, the relationship with "Tony" is pure fantasy. WARNING!!! This story starts with a chapter that describes violence against one...

Love Your Readers: Categories

by Tx Tall Tales on Dec 9, 2019
How To

============================ Help Your Readers. Categorized Your Story Correctly. In Love Your Readers, I wrote about things you do to improve the reading experience for your readers. In Love Your Readers: Categories, I'd like to share my ideas on making it easier for the readers to decide to give your stories a read, by placing it in the right category....

Aphora's Mission Ch. 06

by ValoryG on Sep 15, 2017
Transsexuals & Crossdressers

By all accounts, we were saying a final goodbye to Earth. Even though I wasn't close to my parents (my father a doctor and my mother a marketing professional) I figured my mother would miss me. And I would miss them somewhat, especially at Thanksgiving- and Christmas-time. We six didn't see ourselves as the homesick type, and I personally hoped that Aphor...

The Girlfriend Ch. 01

by nikkiesilk on Mar 26, 2019
Transgender & Crossdressers

"It looks like Sam has a girlfriend at last." "Huh, what?" My attention was fixed on the rugby on the TV and I really wasn't paying attention to my wife. "I said, numbnuts, that a giant sinkhole has opened up in the high street and swallowed the pub and all the customers." "Oh, OK." Rolling her eyes, she said, "What did I just say?" The game was on a kn...

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...

Sarah Wore a Bikini to the Hot Tub

by SarahCD on Feb 11, 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 detail and corrected some...