Free Shemale Stories

Becoming Carla's Girlfriend

Carla and I were watching Netflix at home just relaxing after a long day of work. I remember laying down next to her and looking at the pink toenail polish on her feet. I taunted her as said "I could do a much better job painting your toes than you could." Carla smirked and said, "It's much ha... read more

lacemint August 19, 2023 75%

Kap 1 - Erste Erfahrungen als Crossdresser

Ich lag also auf dem Hotelbett, genoß es die eben erlebten Orgasmen noch in meinem Körper zu fühlen und meinen Saft auf meinem Bauch zu spüren. Dabei dachte ich zurück an die Zeit wie ich mich zuerst zum Crossdresser und dann zur Transe entwickelt habe. Heute lebe und fühle ich mich als Frau auch we... read more

cindy65 October 7, 2019 100%

On the Run

“Your first mistake was stealing hundreds of thousands of dollars from me. Your second mistake was thinking you could get away with it.” As I stood trembling before his desk, Mr. Atwater regarded me as if I were a bug on the windshield of his Lexus. “Do you have anything to say for... read more

shemale lover September 1, 2012 90%

Whores and Pimps - Part I

Malcolm was a middle manager in a small business in a large city. Malcolm led a pretty boring life; he in his forties, single, devoted to his work, he liked to keep himself fit, all of his family lived interstate except for his older sister who lived nearby, and he led a quiet social life. Malcolm h... read more

shemale lover May 13, 2012 85%

Lady In The House Ch. 08

A story by MicheleNylons (Crossdresser must comply with jailhouse heavy.) "You!!!" Eddie screamed through the bars, then laughed. "Well done girls, quite a show, I really enjoyed that; and so did Michele obviously," he said snickering and pointing at the tent in the front of my skirt caused by... read more

✘Transensual✘ February 25, 2019 100%

The Sex Club

When I got divorced back in 1987 I was a very horny man that had not had sex in many years. I had always liked to dress up in nylons etc and learned long ago that I was Bi and liked cocks and pussy. When I finally got my own place after the divorce I almost always would lay around the house dressed ... read more

crossdresser55 September 11, 2019 85%

Vacation fun

I was staying at a nice hotel for a week while working and in the evening, there was not a lot to do so I decided to go for a little walk along the nice pathway they had at hotel. It was very private and wondered around a bunch of flowers and trees and brush and along a nice little river. I had walk... read more

crossdresser55 September 11, 2019 80%

Langes Nylon - Wochenende in Wien

Als ich nach einer zügigen Autobahnfahrt endlich meinen Zielort Wien erreichte, war ich froh endlich dort zu sein. Wir hatten uns schon länger nicht gesehen und freuten uns sehr auf unser langes Wochenende. Auf der Fahrt hatte ich mir in meiner Fantasie ausgemalt, wie wir die nächsten drei Tage wohl... read more

Nylon_Lottchen February 12, 2020 50%

TV FELLATION SALOPE POUR LES NOIRS ⚧️

Ma femme était absente de la ville depuis quelques semaines récemment et je n'avais aucune relation sexuelle. J'ai essayé de me retenir, mais lors d'une nuit particulièrement excitante, j'ai pensé que j'irais dans un bar comme distraction si rien d'autre. Je me suis habillé d'un pantalon et d'une ch... read more

Femboy 2021 February 17, 2023 50%

SOUMISSION CIEL ⚧️ ⚧️

J'ai regardé les pieds de ma mère se frotter lentement les uns contre les autres, les nylons de ses collants produisant ce son distinct et délicieux pour lequel j'étais si faible. *Suisse* Un pied posé sur l'autre, bougeant doucement et lentement, se caressant dans un mouvement hyp... read more

Femboy 2021 March 18, 2023 0%

Date With A Mistress

It was a sultry afternoon and I was sitting in my study remembering the events of the past weekend. Never before had I thought that I would endever to fulfill my fantasies until I met Angela. Friday Night: It was late in the afternoon when I decided to check the adds on my computer. I was look... read more

shemale lover November 4, 2011 90%

RÉVEIL SEXUEL SISSY ⚧️ ⚧️

Si ses histoires étaient vraies, non seulement beaucoup d'hommes ont eu des réveils sexuels entre la fin de la trentaine et le début de la cinquantaine, mais beaucoup d'hommes de mon âge étaient curieux de se féminiser, de sucer des bites et peut-être même d'avoir des fesses. Mais je ne peux pas ... read more

Femboy 2021 February 17, 2023 50%

My Neighbor

When I got divorced and was finally living alone I had many fun times getting fucked all I could by both men and women. I was always dressed when home and loved to stay that way all weekend long and would just put on some pants over my outfit to go shopping sometimes with a coat or shirt over my ope... read more

crossdresser55 October 29, 2019 92%

Longtime friends

*** This a work of fiction but wishful thinking. Beau and Stephen had been long-time friends, they often spent time together playing golf, gym, and fishing. Stephen had a secret crush on Beau for quite a long time or it was Stephanie, Stephens' alter ego that did have a crush on Beau. He found hi... read more

Stephanie_logan February 21, 2020 72%

MIKEY DEVIENT MÉLODIE

Le tout premier jour où j'ai rencontré Heather, elle m'a clairement fait comprendre que le sexe était très important pour elle. La même nuit, lorsqu'elle m'a vu pour la première fois avec mon pantalon baissé, elle m'a expliqué que puisque mon pénis était bien trop petit pour jamais la satisfaire, el... read more

Femboy 2021 January 20, 2023 50%

the park

I was having lots of fun at the park like always dressed like a sissy and taking cocks deep in my ass and mouth like always. It was late and I was getting ready to head home when I saw something walking towards me. I could not make it out at first but finally saw a very pretty girl about 25 with lon... read more

crossdresser55 September 6, 2019 96%

Karen, My School Teacher Part 1

The Meet By FoxyHosed It all started when we got a new class teacher. Her name was Karen. She was a mature lady and had dark red hair to her shoulders. That first day she wore some short dark blue jeans and a brown blouse. My other classmates started whispering about her. “He-he! Have you seen t... read more

FoxyHosed January 29, 2021 80%

Ado est forcé à poule mouillée

Ma première fois avec un autre homme était quand j'avais 18 ans à la fin des années 80. Ma copine était vierge et le plus loin nous sommes allés baiser et frotter avec nos vêtements. J'emmènerais mes magazines sales là où nous habitions dans les bois et enlèverais tous mes vêtements et me mastur... read more

Femboy 2021 January 27, 2023 50%

SISSY MAID TO BE . . . ⚧️ ⚧️

C'était le vendredi typique quand nous nous sommes réveillés. Il est temps de préparer les enfants pour l'école, puis de s'entraîner où les parents de Lizzy viendraient les chercher et les garderaient pour une nuit au bord du lac. Puis se concentrer sur le travail pour nous deux. Nous av... read more

Femboy 2021 March 21, 2023 50%

I Missed Myself

As soon as Dr. Griffin returned to the examination room, I knew that the news wasn’t good. I could tell by the way he avoided my eyes as he studied his clipboard and fidgeted with his pen that something was wrong, terribly wrong with me. The ache in my groin that I had been ignori... read more

shemale lover March 20, 2013 100%