Tranny Stories

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The Private Transvestite Detective

by MicheleNylons on Sep 16, 2017
Transsexuals & Crossdressers

The Private Transvestite Detective (Or The Undercover Dick) With apologies to the writers of the various movies from which I borrowed some inspiration (and a few good lines). Chapter One It was late Friday afternoon and I sat behind my desk smoking a cigarette, leaning back in my chair with my high-heels resting on yesterday's newspaper. I contemplated m...

I should have Kept My Mouth Shut

by submissiveanne on Jan 28, 2019
Transgender & Crossdressers

This is a story that takes place years after the events of "Ramona Changed Me". *** Sometimes I have a big mouth and don't know when to not say something. This got me into trouble. I was 26, this was like 2005 and working at a job where I was assisting in the repair of plumbing damages. A vendor or someone goes into work on a home, they damage the sprinkl...

Finishing School For Ladies Ch. 08

by MicheleNylons on Oct 9, 2017
Transsexuals & Crossdressers

Chapter Eight -- Passport To Eternity "So are you seriously thinking about getting tits?" Sally dropped her newspaper and snuggled up to Valerie. "But I thought the whole tranny deal was only for two or three years? Just until Tony stopped looking for you?" Sally said inquisitively. "Well it was. But now I don't want to live any other way. I can't tell yo...

Once Upon a Tranny

by Art on Sep 14, 2017
Transsexuals & Crossdressers

Once Upon a Tranny Art Kautz Copyright March, 2005 Bob was having a time with the winter traffic. It had snowed last night, the roads were slick, and all too many people were driving like they had never seen the stuff before. He had started out early in what turned out to be a vain attempt to get to the office on time. Conditions were worse than he had expe...

How I Became A Filthy Tranny Slave Ch. 02

by beyondkink on Sep 13, 2017
Fetish

This is the continuation of the story "How I became a Filthy Tranny Slave" where a young man who lives out his fantasy of dressings as a transvestite and being defiled is abducted Ch. 02: Tranny Slave Is Imprisoned When I woke up from my drug induced coma it took a few minutes to adjust and analyze my new setting. It feels like I had been out for days, pos...

The Benefit of Plasma Television

by Kitkat103 on Sep 12, 2017
Toys & Masturbation

MaloMarz6969 -- Lol what a freaking idiot. So what are you up to? Sbarron85 -- Just waiting for Matt at his place. He is supposed to be working late. MaloMarz6969 -- Aha. I did not know that office drones had to work so late, honey its 11pm! Sbarron85 -- I know that, what are you implying? MaloMarz6969- Well I think he is out too late to just be desk joc...

The Initiation Ceremony

by DrLuverotica on Oct 21, 2019
Transgender & Crossdressers

FRIDAY A.M "Don't forget I'm out at Carrie's hen party tonight." Jo said, as she was just leaving for work. "Carrie, your secretary?" "That's right, Carrie my very sexy secretary." "Will you kiss a girl and like it?" "You wish!" "A boy can fantasise." "Well let's hope Carrie's got some nice fantasy games lined up. Or a male stripper or two." And with...

I Is for Irene

by BethanyJ on Sep 16, 2017
Transsexuals & Crossdressers

*** A series of stories with transgender themes which I hope will be of interest to those who like women, or would like to be a woman. Which includes me! *** It was all down to 'Jennie', really. If she hadn't reacted so clearly and positively when I'd suggested we should meet, things could have - indeed would have - turned out oh-do differently. I'd actua...

M Is for Mandi

by BethanyJ on Sep 16, 2017
Transsexuals & Crossdressers

********** A series of stories with transgender themes which I hope will be of interest to those who like women, or would like to be a woman. Which includes me! ********** That night, that Friday, had been highlighted on the kitchen calendar for weeks, though my wife didn't know the reason why. OK, so she was off to her sister's for the night and that wa...

The Virgin Tranny & the Bride Ch. 04

by yano on Sep 25, 2017
Transsexuals & Crossdressers

Continuing the story of young transvestite Roberta and her adventures with Margaret and John. I have also received the following letter which is a little worrying. Dear Yano, I'm very sorry it has taken me so long to send the next part of my story, things have been very strained over the past few months and particularly between me and Margaret since I got...