Trans On Sissy Stories

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Orientation
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Re-tooled

by Sissyhalo on Mar 13, 2018
Transsexuals & Crossdressers

Re-tool your life. Re-tool yourself. Sick of not getting what you should? Sick to fucking hell of all these assholes getting with hot people they really don't deserve? Sick to hell of Liberals and Feminists making impossible to jump through hoops so that only the privileged people get to be happy? Sick of being a goddamned incel? Look we all know that...

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...

First Time Sissy Maid

by bart2077 on Sep 13, 2017
Transsexuals & Crossdressers

I had been fantasizing for many years about serving a dominant Mistress, watching lots of movies online, and generally lusting over the doms I saw posting ads. At the age of 28 I finally found the courage to answer a rather intriguing post by an older woman and her trans partner who were looking for a sissy maid for ongoing service. I answered the ad, includ...

Fetishville (Adding Encouraged)

by VioletWinters on Sep 26, 2017
Fetish

Welcome to Fetishville! I am Violet, the mayor here. I know you're eager to start so let's get to it. To begin with your adventure, press the "Start Game" button on the right and find your fetish. It is pretty straight forward. If your fetish involves dominating, select [Dominant]. If it involves being dominated or being submissive, select [Submiss...

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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...

Samantha Meets a Dom Master

by SamanthaSatine on Sep 16, 2017
Transsexuals & Crossdressers

A true story - I am the main character and all the various activities described were undertaken with my consent...no harm came to me in any way... ***** The date was fixed. The room was booked – neither of the willing parties could accommodate, a not unusual event in the world these two inhabited from time to time. The morning of their meet had now arriv...

Bar Table Fun

by princess_nicole on Sep 13, 2017
Transsexuals & Crossdressers

Up to Miss Kate's door i walked, then knocked on the door happily. i hadn't been to Mistress's home for a couple weeks, and was thrilled to finally be back to see Her. She opened the door and smiled at me, i smiled back and lowered my eyes. "Come in sissy", She ordered. i quickly scampered inside and set my bag on the floor. She closed the door and came ove...

Blackmailed!

by 57 on Sep 26, 2017
Miscellaneous

Who you're isn't important. But what you have in your power is a very important thing, at least for the people who's involved in the files that you have. You have pics, videos, and everything that could be very valuable since these pics and videos could destroy lifes, ruin marriages, end political and professional careers, etc. You plan to use these incrimin...

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le reportage

by isis13 on Jan 12, 2020
Fetish

Je viens de sortir de L'universiter avec mon diplôme de reporter à 21 ans et je décide donc d'allez chercher du travail mais aucune entreprise veux de moi donc je décide de moi proposer pour une personne locataire un journal sur le web après tout ça reste un journal je dépose donc mon CV. JE m'appelle clément je recherche un travail dans le journalisme depui...

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Making Holly

by Sissyhalo on Sep 19, 2017
Transsexuals & Crossdressers

My name's Jamie and I moved back to my hometown. I had a lot of bad memories here and most of them stemmed from being bullied in high school and a lot of that came from Holt Thompson. A loud mouthed jock in school he was the center of the basketball team and really, really arrogant. I was a geek, a comic kid and dungeons and dragons kid and all that stuf...