Free Shemale Stories

A long fun weekend with Desi

I come over to your place after work on Friday evening. We are going over to one of your friends houses for a get together. I head home real quick and change clothed and get my bag for the weekend. I shoot you a text as I head out the door, "On my way". You are at home getting ready to go ... read more

b0099b June 15, 2016 80%

Milking Time Jordan's Arrival

These stories involves a group of shemales who live on an island that exists in our world, but they chose to remain mostly isolated. That's part of the reason I also call them amazons. The shemales in my stories have genitalia that start at John Holmes' size, and then get much bigger. (This is a... read more

gman57 September 25, 2019 83%

Feeling Womanhood Deeply

It seems somehow that my desire for womanhood is the one thing that everyone says I can’t have, but who are they to say why I should feel a certain way or want certain things? I want the very thing that their closed minds crusade against. It seems that the thing that brings me the most joy is the th... read more

Regina10 August 26, 2021 50%

Vegas Baby: Swinging for the Fences

"Hello," Miss K said as she answered the phone. "Where are ya? You're gonna be here in 5? Alright. You got the address for IHOP, right? OK, See ya in a bit. Bye." "So is this girlfriend of yours on her way?" Jennifer chimed in. "I mean if she doesn't exist, this... read more

shemale lover November 15, 2011 73%

A Fairy Tale Part 2

=-=-Chapter Six-=-= I woke up sometime later and I was feeling better, even a little hungry actually, and I wanted a shower and I needed to pee and...I cocked my head as I heard the unmistakable sounds of Mistress Stacy's bed moving. She had a large one, king sized, with old springs or somethi... read more

shemale lover December 6, 2011 100%

The Greatest Lie Part 3

My weekend escapade with my first real lover, Jake, convinced me that I was destined to live as a girl, despite having been born a boy. Unfortunately, it was my male persona to whom the University of Minnesota had extended admission and a scholarship, and I wasn’t quite sure how they would rea... read more

shemale lover January 19, 2012 100%

bi to sissy caught and turned

It was during a Wednesday nite supper this past April when Penny my wife of seven years, suddenly looked me straight in the eyes while calling me a GAY COCKSUCKER ! Instantly while I swallowed hard and quickly looked away from her, my worse dreaded fears in life had somehow just become reality! So ... read more

redthongthong August 2, 2022 100%