Free Shemale Stories

HOW MY AUNT AND SISSY NEPHEW CHANGED MY LIFE FOREVER! (fictional

It was the very first night of my month long North Carolina July summer vacation stay when my Aunt Meg suddenly entered the bedroom that I was temporarily sharing with my younger cousin Rudy. Being so openly effeminine in his body language,voice and looks, I had already planted such dirty thoughts ... read more

CDDIXIE4U January 8, 2019 91%

My Seductive Secret (True Story)

During my childhood, me and my brother used to play with two other boys who were our neighbors every weekend. One day we decided to wrestle, and I took on the youngest one, (he was about 2 years younger than me, like my brother) and we wrestled in the shed while my bro and his bro (who was my age) w... read more

Chickzdigmeyup June 18, 2019 91%

fuck by my best friend's family

= Part 1. Alice's father = My name is Onikky 28-year-old Shemale from ASIAN, this story only shares the first experience of making love. The story begins when I first moved to a big city, looking for a new atmosphere, I don't have a place to live that I know is only my friend's name Alice who ... read more

Onikky June 25, 2019 80%

Wife makes me dress like a slut

Back in the 80's my wife and I did a lot of drugs ...she was super hot with long legs and loved to dress in stockings..short skirts...high heels and lots of makeup...and WOW could she suck and fuck !! One night when we were really loaded, she got me to let her dress me in her lingerie...panties,bra,... read more

Diana58cd March 24, 2020 75%

Emily's First Daddy

This is a story how a curious male can become a sissy slut seemingly overnight. So I was in an online adult chat just talking with random people and happened to mentioned where I live. Then all of sudden, I got a message from a man calling himself bear daddy. He introduced himself and said he was ... read more

User Removed October 21, 2019 100%

Sissygurl

Sissygurl development A true sissy always wants to always look as sexy and desirable as possible and with a body that looks fabulous in your sexy sissy outfits so you will be super motivated to stay sleek and slim. Now let’s talk make-up. Besides the essential stuff to have in your make-up kit... read more

amberdoll July 22, 2020 100%

Sissy Femboy Chrissy in Drag at the Club

"Can you wear a dress tonight?" "I can't crossdress in public, I'm not 'out' and don't want to be seen that way." "That's okay. We're going to a gay-only club that has a drag queen show tonight, so you'd fit right in." "Cool, but I'll have to change when we get there." "Awesome! See you tonight!... read more

Chrissy Tunnell February 3, 2022 100%

Meeting Amanda

I’m a happily married man. My wife Tess and I have been together since we were teenagers. We were each other’s first real lovers and being in our mid-thirties by now, we still madly in love with each other. Tess and I always are very honest and open to each other. Both in normal life and sexual... read more

rforasht July 20, 2022 100%

She also conquered my soul...

Initiation in a new era... Almost three months since I offered my virginity to a wonderfull he-woman, Selmi... unfortunately I had to cancel the second day we planned to spend together with my LORDESS because I quitted the town where we met the day before. Since, only few summer fling messages...... read more

hippocampus_171 November 22, 2022 50%

Jesse in a dress

Jesse sat primly, as been instructed, gracefully crossing his smooth, shapely young legs reveling in the sensation of the light-taupe silk stockings, sending yet even more flurries of butterflies through his tender tummy. He gently draped the flaring of the soft pastel-yellow floral summer dress ... read more

ALEXEAMES January 13, 2024 100%

My pink panties

My pink panties .... You pointed to the bed and said to put on the lingerie that you had picked out for me. There on the bed was a pair of pretty pink panties that had a bow on the front, a pink lace bra, a pink lace garter belt and a pair of fully fashioned stockings. What a lovely feeling ... read more

amberdoll July 9, 2018 50%

My pink panties

.... You pointed to the bed and said to put on the lingerie that you had picked out for me. There on the bed was a pair of pretty pink panties that had a bow on the front, a pink lace bra, a pink lace garter belt and a pair of fully fashioned stockings. What a lovely feeling rolling the stocking... read more

amberdoll November 7, 2018 66%

sissygurl

Sissygurl development A true sissy always wants to always look as sexy and desirable as possible and with a body that looks fabulous in your sexy sissy outfits so you will be super motivated to stay sleek and slim. Now let’s talk make-up. Besides the essential stuff to have in your make-up kit... read more

amberdoll February 16, 2023 100%

Horny Writing A Strange Habit

I enjoy watching videos which I can Vicariously live. This is nothing more than my horny hobby, an amalgamation of various thoughts. My form of hands free edging. Spell checked only, "No I haven't proof read a first draft, not trying to publish masterful works here." Hope to hear from those w... read more

Araina March 8, 2021 100%

NERVOUS MEETING

On a cool fall evening I was walking about town when I came across a sign outside a coffee shop saying, "lonely? stop in for a cup and new friends". It was plain except for the light rainbow in the center of the sign. Being curious and also a bit lonely myself, I stepped inside. It was nothing m... read more

77James January 3, 2022 33%

De la pucelle quinquagénaire à la mature disponible...

***Prologue - Confessions: Depuis que j’ai offert ma virginité, je me mets chaque jour un peu plus dans la peau d’une femme. Le petit bled où je vis m’interdit de m’exhiber socialement. Totefois je me suis faite une complice, mon épileuse qui me reçoit après la fermeture . Depuis mon nouveau début,... read more

hippocampus_171 January 11, 2023 50%

From a 50's virgin to a Mature good for all

***Prologue - Confessions: Every day since I offered my virginity, I put myself in the shoes of a woman. The little town where I live forbids me to show myself socially. However I made myself an accomplice, my epilator who receives me after closing. Since my new beginning, male masturbations are not... read more

hippocampus_171 January 11, 2023 100%

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%

Danielle Works a Saturday

It had been a few months since his wife left him. Well "ex-wife" as the divorce had been recently finalized. It was her choice; she walked out on *him*. She said she got tired of "Danielle", even though she was entirely responsible for Danielle's "birth" to begin with. ... read more

shemale lover June 18, 2012 100%

Jo, Shemale Goddess! Part 2

Jo chuckled as the man in the sharp business suit looked hastily away when she looked up and caught him staring at her legs, again. Her 'Rupaul' legs as men with a history of watching men dressed as women called them, or her 'Naomi' legs as the newer ones to the scene seemed to think. Both divas had... read more

shemale lover September 5, 2011 0%