Tranny Surprise Stories

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There's Something about Sarah Ch. 05

by MicheleNylons on Sep 18, 2017
Transsexuals & Crossdressers

Chapter Five - Redemption Tina and I, rightly in my opinion anyway, decided that we wouldn't move in together. Sure, we would save on rent if we did, but the temptation to constantly give into our urges would undoubtedly distract me from my studies and Tina from her work. Also our relationship was volatile, there were periods of serenity when I thought I mi...

Danielle's First Time

by FellatiaViper on Sep 15, 2017
Transsexuals & Crossdressers

Danielle was born in the winter to 1976, but she was born a male by the name of Daniel. Daniel looked like a normal male child aside from liking girly things. Whenever Daniel would play dress-up he'd always dress in his mother's or his aunt's clothes and his parents thought that was cute until Daniel got a bit older then his father sternly told him, "boys do...

Mistress Chantel, Tranny Dominatrix Ch. 05

by Sissy_Chantel on Sep 19, 2017
Transsexuals & Crossdressers

Chapter Five: Monday Morning You look so Fine. About 7:00am and I awake from the sofa bed of Gillian's place. I feel better after sleeping off the fun Sunday night activities with Kerri and friends. I need to wash up and get home to dress for my Monday schedule at my dominatrix studio. I shower and feel refreshed. As I dry off, there is a door knock and Ker...

The Tranny Lover - Judy, Judy, Judy

by erectus123 on Jan 20, 2020
Transgender & Crossdressers

-------INTRODUCTION-------- All the characters in this story are over the age of 18. It is a true story that took place in the 1980s and 1990s. Most of the people in this story are still alive, but sadly, not all. The word "tranny" was not derogatory back then. If you find it offensive, please realize that it reflects love, admiration, and concern. These...

Mayberry, the Black Goddess

by devoutmalesub on Sep 16, 2017
Transsexuals & Crossdressers

Another lonely night led me to walking down the dimly lit street and wandering into the sex shop. There wasn't too much adventure to be seen there, very comparable to my apartment. I was looking at toys. Specifically, butt-plugs. Not that I didn't already have one; in fact, I was wearing one at the time. The little bell above the door rang. I looked at the...

A Tranny Whores Tale Ch. 02

by KinkStevens on Sep 16, 2017
Transsexuals & Crossdressers

This is a continuation my tales of Elle. based on real events...Please vote AND comment! thx By the time I pulled up near the house it was 4am. I was drunk, completely revved up and ready for some action. I emptied my pockets of everything except Elle's 'offering'. I took my last swig of vodka from the bottle and took one last deep breath. "He we go, aga...

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...

Ellen's Candy

by Jae_one_01 on Sep 16, 2017
Transsexuals & Crossdressers

Sometimes I get in the mood to suck a dick but I’ve never considered myself gay. I’m @ the very least bisexual but I don’t like to limit myself to that either because I think it restricts my sexuality. I get turned on watching all types of sexual situations that you could think of; just let your imagination determine what that means. On that particular Sat...

T Is for Teresa

by BethanyJ on Sep 16, 2017
Transsexuals & Crossdressers

*** Transgender-themed stories which I hope will be of interest to those who like women, or would like to be a woman. Which includes me! *** It was when I was still living at home, or at least staying there in the college holidays, that Mum came home and found me and Jack Horton lying on the living room floor, naked, and giving each other sixty-nine. She k...

Picking an Indy Car Girl in Club

by unique_cabelas on Aug 20, 2018
Transsexuals & Crossdressers

Sam has a little secret, he does not mind getting some of the shemale cock. After a night out with the lads he disappears from the group down the road to a gay night club. Sam has never been in a gay night club and feels a little out of his depth. He has had a few drinks so is feeling relax and sits down scoping out the club. Looking around the club his eyes...