Free Shemale Stories

Random Thoughts on Tits

Tits. You have to love them! They bounce. They hang. They jiggle. They sway. They tremble. They wiggle. If you're a man (or a lesbian with a strap-on strapped on), you can even fuck them. They can be bound with cords so that, the blood flow to and from them restricted, they turn purple. Clothespins ... read more

shemale lover November 17, 2011 100%

TO BE OR NOT TO BE – PART 2

TO BE OR NOT TO BE – PART 2 by Spanky de Bautumn Part 1. Sunny, Mel, and Shari learn they are going to New York to perform a play off Broadway and are really excited about it. Being a small troupe, we unseen members had to wear many hats. Unfortunately, there was just the two of us, Joe Donn... read more

SpankydeBautumn February 22, 2021 100%

I was Teen Shemale for the US Army

Chapter 1 Reform School Romance! I couldn't believe that all I got from my uncle Bill when he died after all he said to me about my being his favorite grand nephew was an old diary from World War II. I mean I thought we got along pretty darn good, and its not like he had any money or anyth... read more

shemale lover October 22, 2012 100%

Exposure, Disclosure

The Greatest Liar, Exposure, Disclosure © Alexandra Rios 2019 Author’s Note: This is a continuation of the narrative which commenced with “My Awkward Phase”, which I posted here previously. Readers may wish to read that before continuing, although I have written them to stand alone. Natives s... read more

the greatest liar June 18, 2019 100%

Sissy Acceptance *

La primera vez que vi porno interracial algo recorrió mi interior de una manera que nunca antes había experimentado, era como un hormigueo que pasaba por todo mi cuerpo….. hasta llegar a mi ano. No sé que fue lo que me motivo más si la insaciable obsesión por probar una verga negra, ó el hecho de... read more

Sissycrick May 4, 2023 50%

ACROSS THE STREET AND TWO DOORS DOWN by Spanky de Bautumn

Jamie knew he was different. He didn’t fit in with the other boys, but he didn’t feel like he fit in with the girls either, he just knew he was different. He wasn’t into dolls or balls. He was the smallest boy in his class and more than half the girls outweighed him. But the one thing he had going f... read more

SpankydeBautumn January 29, 2021 72%

Susan's First Time Part 4

The shadows of late afternoon crept across the city when Susan paid the cabbie off. Why had 'he' wanted her to come down to this neighborhood? She looked around with apprehension at the garish lights of bars and adult bookstores flashing in the growing darkness. One or two streetlights flickered on ... read more

shemale lover October 14, 2011 60%

Rebound!

It’d been a while since I’d last been out and had some fun. My relationship with James had broken down, and I had decided to move on. I went back to the string of websites and apps that I had previously used and had a look around for a few casual encounters. Soon enough I found someone, they hadn’t ... read more

ATC97 April 5, 2016 100%

Nunca se Olvida

He tenido la oportunidad de tener sexo con varios hombres, algunos mayores que yo y otros muy chicos, no me fijo en estereotipos o personalidad, solo me gusta disfrutar del sexo..... Pero siempre hay uno que te deja enamorado, Daniel su nombre una persona que conocí por medio de un chat. No pas... read more

Carla Travesti October 5, 2020 100%

Camming Down the Rabbit Hole Ch. 08

A familiar sensation greeted me as my eyes opened and a yawn escaped my mouth, that oh so delicious feeling of my morning wood straining against my silk night ware. It was becoming an ever occurring pattern that no matter how large the orgasm the night before I would wake with the hardest of cocks, ... read more

Dani_does_Dallas November 15, 2021 90%

Alex

I'm a straight guy! a few years ago, I stubble the cross shemale p***. now I must say, it felt weird, I mean being used to watching females doing p*** on my life. but I have to admit, these shemales that I was watching were passable, and most of all looked very f*******. shemale p*** made my di... read more

Mike212 May 28, 2018 87%

My Awkward Phase

My Awkward Phase ©Alexandra Rios 2019 The greatest lie is that what happens in high school doesn't matter, because life begins in college. I pretended to agree, although I never believed it, for I was the world's greatest liar. Wannabees I was hanging out with my friends Quinn, Barb and Anne ... read more

the greatest liar June 14, 2019 85%

Chance Encounter Part 3/7

We were passionatley kissing each other for a while and slowly but surely I could feel her wonderfull cock grow hard again………. I told her how good her cock felt and we continued kissing but now she was rhythmically sliding her cock over mine while we kissed. Her luscious balls felt rock hard as w... read more

Katlick October 21, 2019 33%

Am I gay?

Please help me. I'm confused and unsure if I am gay. I feel so ashamed of myself. I don't want to be gay but I was molested by my neighbors at 6 years old and from then on I would wear my mom's panties or sniff my sisters while masturbating. Cumming would always make me feel guilty for what I have d... read more

Chinaysissyslut February 24, 2020 38%

My story; don’t know which one... English version (1)

I notice that the're not many french language readers so have I decided to publish an English version End of the 80s; a tough time for a young reporter travelling thousands of km's for a crumb of titbit. A new event and more pressure every day for me. Seeing me in this floundering state during a ... read more

hippocampus_171 July 21, 2022 100%

First Cross-dressings Loosing Anal Virginity

It happened after a month of me blowing that guy twice...I mean I was so damn excited and was craving for his cock....I was blowing him every weekend in his car after the school...his cock was almost 7 inches and was so thick and that I like so so much the gagging he was giving everytime, that chock... read more

Trapbomb1 July 29, 2022 100%

How it all started!

Hello to everyone who’s reading my story. Before I start I would like to introduce my self and tell you few things about me. My name is Ria Sweet I’m 31 years old and I’m from USA. I was adopted when I was only few months old and I never met my biological parents. The story I’m would like... read more

Ria Sweet August 24, 2022 92%

J'ai enfin goûté la bonne chère/chair

Dépucelée en bon et du forme... Chose jamais osée depuis que je goûte la jouissance par tous les sens et dans tous ses sens... Je la découvris quand elle m'a sourit en guise de remerciement pour lui avoir cédé le passage dans la superette du bled où j'étais pour affaires. Sandales à ses pieds d... read more

hippocampus_171 November 9, 2022 50%

lust of a sex-agenarian nana-pops

Frenzied lust of a sex-agenarian nana-pops; between dream and reality I had never fantasized of a manly man, even after offering my virginity; to a fabulous sissy. Before my new Era, my fantasy preferences were always with glabrous he-she’s, same about my relationships after… BUT BUT BUT… My last t... read more

hippocampus_171 July 9, 2023 50%

Unexpected Twist

I'm a reporter for a regional newspaper in Germany, in my 30's and always in search of a good story. Last summer, while visiting a local pride festival for a short report, I got in contact with the regional queer community. A few months before, a new editor-in-chief took over in our office, a very c... read more

webandy87 November 22, 2023 100%