Free Shemale Stories

Maddie and the public bathroom antics

I had put on my lingerie and my dress underneath my manly clothes and was preparing myself to go to a public bathroom. The idea was to enter a cubicle, take off my boring man clothes and sit there looking like a sexy sissy where I could video myself on my smartphone. I needed some hot new pics, so I... read more

sissymaddiex January 6, 2023 100%

SISSY MARI DE MAÎTRESSE

Morgan Ashley était une très jolie dame, pas une star de cinéma glamour, mais bien plus jolie que tout ce que son mari mauviette Robin attirerait normalement. À peine sortie de la douche, elle portait un peignoir en velours côtelé rouge et ses longs cheveux roux étaient enveloppés dans une serviette... read more

Femboy 2021 January 20, 2023 100%

LE CONTRAT DE MARGOT

Madame Margot Elizabeth Stott était l'objet de mes désirs, des désirs très secrets ; désire que je n'aie jamais eu l'intention de la laisser - ou qui que ce soit d'autre - le découvrir. Mme Margot Elizabeth Stott avait, au moment où je l'ai connue pour la première fois, environ 45 ans, peut-être ... read more

Femboy 2021 February 16, 2023 100%

Shemale Porn

Nowadays, I masturbate exclusively to shemale porn. Like most guys, I started out reading, then watching, straight pornography. Sure, there was the titillation of happening across a cross-dressing tale in the glossy flesh mags, but they were for a ‘straight’ readership, and didn’t quite scratch that... read more

Daddybear71 May 24, 2023 100%

The Twink and the Bear

He stood there, slowly rubbing his hardened cock in the confines of the public toilet cubicle, trousers around his ankles, his legs adorned in black nylon stockings, held in place by the straps of his delicately laced suspender belt. It was so naughty to be playing with himself in a public place, wi... read more

Daddybear71 March 28, 2023 100%

MON SOUS-DESTIN ⚧️ ⚧️

Quelque part au milieu de la vingtaine, j'ai réalisé que les femmes avaient du pouvoir sur moi. Les commentaires de mes amis parlaient de conquêtes féminines - je n'avais pas de tels sentiments. J'ai été obligé de renoncer à mon pouvoir d'homme et de me soumettre à leur pouvoir de femme. Ma se... read more

Femboy 2021 April 14, 2023 100%

How I sucked my first shemale cock

It was the beginning of the year 2023, in January, three days after New Year's Eve. I was driving home in the morning from a party 100 miles away from my hometown. On the highway, after going half the distance, I received a notification from my dating app, and I was like, "Oh, a new match", I'll che... read more

cock&heels69 May 25, 2023 100%

2.ΜΕ ΕΝΑ ΦΙΛΟ ΓΙΑ ΤΣΟΝΤΑ ΣΕ ΚΙΝΗΜΑΤΟΓΡΑΦΟ Μια φορα με πηρε ενας

2.ΜΕ ΕΝΑ ΦΙΛΟ ΓΙΑ ΤΣΟΝΤΑ ΣΕ ΚΙΝΗΜΑΤΟΓΡΑΦΟ Μια φορα με πηρε ενας φιλος μου να παμε να δουμε κινηματογραφο τσοντα.Δεν ηξερε τιποτα για εμενα οτι ειμαι crossdress.Εγω τις περισσοτερες φορες μεσα απο το τζιν φοραω καλτσες η καλσον ανοικτα απο κατω, σουτιεν η μπουστακι και φυσικα στρινγκ.Η αισθηση του ν... read more

crossofia October 1, 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%

Andy In Pantyhose

He had the house to himself for a few hours. Andy slid his older sister Kelly's taupe nylon pantyhose slowly up his nice, smooth legs, wriggled them up around his narrow boyish waist the band snapping in place. His penis was so stiff against the wispy fabric! He sighed happily. Sitting down on ... read more

ALEXEAMES January 18, 2024 100%

My cross dressing journey

I am a man who likes to cross dress, currently single and living alone in Beijing. I like to dress up as a woman and go out, passing through every street, entering nearby shopping malls and supermarkets, as well as the women's restroom inside, and live streaming on a live streaming platform. I also ... read more

boysgirls February 15, 2024 100%

Two CD's the first time we meet.....

We are meeting for the first time since talking online. I want to dress for you gurl, I want to feel as you do, I want to be your slut, your slave of desire. My panties are a sheer white, my hard cock can be seen ever so pressing against them, I rub myself for you as you watch, drooling now. Hand... read more

kelliecdgirl April 10, 2024 100%

Sweet Encore

I was alone tonight and feeling just a bit paranoid as I listened to the soft music. The soothing sounds put me in a seductive mood, but It seemed that all my lovers were too busy for me, or they had other plans. Uncle Barney and my detective were probably home being dutiful husbands. Bo was under h... read more

Regina10 May 9, 2024 100%

What a sissy crossdresser really craves and fantasizes about

(This is non-fiction) Lots of attention. To be seen and watched. I want the neighbors to see me as I stroll in my yard wearing white vanity fair panties and bra, heels, with a lacy top and a cute bob wig. With my cock raging hard thru the pretty lacy panties, struggling to be free, bouncing around... read more

kelliecdgirl May 21, 2024 100%

Willows transformation

Fern and I had been married for three years. Our sex life had become bland, routine, and, frankly, I preferred masturbation to the work it took to cum by intercourse. I was pretty sure that Fern felt that way, too. You see, my cock is, at best, 5 inches. My touch, or my tongue, on her clit seemed to... read more

shemale lover February 4, 2016 97%

A Night of Lust

I was out at a night club with a few friends, and we were there for for a while before I noticed this sexy, rather short girl across from me at the bar looking over. I could tell, even from this distance that there was something special about her, I wasn’t sure what that was quite yet though. The mo... read more

JessicaEdwards August 7, 2018 96%

Dana becomes a woman

All her life, Dana had felt different. Born a boy, she always preferred dressing in girl clothes and playing girl games. She was mistaken for a girl from the time she was toddling - her feminine face and manner always convinced people. By the time she graduated high school, Dana discovered her ma... read more

shemale lover July 20, 2013 95%

Jordan's First

My name is Jason, I am a 33 year old road worker. The pay is okay but I never had much more than what I needed to live comfortably. I was hoping to save up for a nice vacation and decided the best way to do that was to take on a roommate. I live in a decent sized two bedroom apartment and the seco... read more

Hydra1979 January 25, 2019 95%

Best session with a T Girl

I like T-Girls. Recently had a chance to go to Costa Rica for work. While I was there I decided to see what Costa Rica had to offer in this department. There is quite a good amount of girls to select from. I started texting this Tgirl and we set a time. I got ready and headed over. It was a Hotel th... read more

horny.hiker April 30, 2019 95%

My TS Journey

I'm a straight, married guy in my 30's, at least that how I appear to everyone that knows me. I have an intense obsession with Trans women that I have been indulging since I was a teenager. Over the years this fixation has grown into something that ranged from watching porn initially, to having my a... read more

iconicirish October 26, 2022 95%