Crossdresser Chastity Stories

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From a Husband to a Dutiful Sissy Ch. 04

by Sissy_Chantel on Sep 18, 2017
Transsexuals & Crossdressers

A quick note about this chapter. It runs a tad long as I want it to really set things up for Chantel's future, not just some sissy maid for her now Mistress wife, as cool as that can be, but to develop a more varied sissy, crossdressing, maid and slut story. I hope it works for my readers. ***** Chapter Four: Moving on to reinforcing my new lifestyle Satu...

My Wife and I Became Sluts Pt. 01

by mandiejune on May 22, 2018
Transsexuals & Crossdressers

My wife Carol was away for a week due to business conference. She was blonde 25 years old 5' 5" with very sexy body and 36C breasts and very sexy bum. We had been married for 3 years and had no children. I was called Tom and 28 years old and 5' 6" and thin. I was IT systems designer and worked from home. I was also a crossdresser that my wife and Mistress al...

Ms. Jay's Shoe Store Encounter Ch. 01

by jojo23456 on Sep 16, 2017
Transsexuals & Crossdressers

Ms. Jay woke up thinking it would be a fine day to miss work and go shopping for that new pair of high heels she so desperately wanted. After eating breakfast she prepared to go looking as sexy as she could, she wanted all the men to turn their heads to watch her hip movement. Arriving at her favorite store," Bells shoes for Large Women," she noticed anoth...

Last Minute Crossdressed Sex

by Lovinhose on Sep 14, 2017
Transsexuals & Crossdressers

I like to write and share my experiences with the world, and I prefer writing about REAL experiences, thought at some point, as in the past, when I hit a 'dry spell' and have no true story to write, I will write a piece of fantasy fiction. I am happy to say, however, that this story, while nothing special, IS TRUE, and I am happy to share it with you all. Al...

Gender Change: Magic Closet

by Zekar on Jan 26, 2017
Fantasy

There is magic in the world. Narnia was just the tip of the iceberg when it comes to the magic that a wardrobe or closet can do. You find yourself directly in the crosshairs of such a magical encounter. Whether malicious or benevolent, that is up to you... This is merely the introduction to a much more interesting tale. (Dear reader, if you like this story a...

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A special Christmas

by Chuveiro on Dec 17, 2018
Fetish

It was already December and I was home alone. Mommy had gone shopping all things she would use on Chiristmas dinner, which would be at our house. I went to my room and got my clothes and toys. I was a sissy, but nobody in my family knew that. The only person who lived with me was mom but she was so old she couldn't notice anything. I dressed up and started t...

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An influential Dare

by femboyslut122 on Apr 20, 2015
Fetish

As a college student most of Kyle's time was spent in class or doing work for class. He knew that others found a better balance, or lack thereof, between class work and a social life. Because of this Kyle always looked forward to the last Saturday of each month. He and his friends would get together once a month to catch up and dick around while playing tabl...

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Girlfriend's Suprise ...

by Shelly7 on Feb 6, 2020
Transsexual

My name is Johnny and I am a lonely 18 year old geeky kid, I never had a girlfriend and was always feeling left out, I had a few geeky friends, all of who was also just like me. I have a confession though ... I have always been attracted to penis's, I never liked boys or men per say, just to their parts. There had been many times when my best friend Cho and...

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the corporation

by davidigor on Oct 21, 2014
Transsexual

you arrive to the building, you've been requested to come here to sign a contract for working here the call didn't give you too much information and you can't remember having asked for a job here... but you need the money so you decided to come here the building is a big one in an important neighbourhood... but strangely, the door is in a small alley in a si...

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The Club of Fools Ch. 05

by sublocked on Sep 19, 2017
Transsexuals & Crossdressers

Author's Notes as before: (1) This is fiction; (2) Do not read this chapter out of context. Read chapters 1-4; (3) Jason is a masochist; (4) Victoria is a sadist and possibly a psychopath, her actions illegal; (5) Do NOT ever attempt "breath play" as it is described herein; (6) Do NOT ever leave anyone in bondage as severe as this for as long as this a...