Free Shemale Stories

Winsome Morgan pt. 2

I was so taken by her, and having so much fun toying with this cute little weenie that I didn’t notice that poor Morgan was getting weak in the knees. Just when I realised that she was trembling she said, “Stacey, I need to sit down.” “Of course my dear.” I gently guided her over to the edge of t... read more

lissomlover August 9, 2022 100%

Porn Princess

They say if you are going on a journey of revenge, to dig 2 graves, one for your enemy and one for yourself. I thought I understood the meaning of that saying, but never so much as right now. My name is Dan, and at the age of 21, I had been working for nearly 2 years as a production manager for ... read more

shemale lover September 2, 2012 76%

La pistola NEGRA del Tío, entre Las Bragas de Mi Tía LA PUTONA

Aaayyy.. Yo sabía que la Tía había sido Flor de PUTONA.. pero, jamás me imaginé que me iba a tocar a mí 'hacerme cargo de sus cosas'.. su 'herencia'.. la casa ya vieja, por reordenar destinar y.. LAS COSAS que una descubre ya con los años! Todo estaba igual, pero HORRIBLEMENTE ARRUINADO.. más, e... read more

Ari Riè June 3, 2021 50%

Lope

Je suis une salope C’est un des fantasmes récurrents de la majorité des hommes qui aiment se travestir. Et j’avoue que l’idée m’a souvent excitée. Alors que j’étais avec ma femme dans une boutique de lingerie à Pigalle , des dessous très sexy entre les mains, un homme d'un certain âge a surpri... read more

osvp75 November 12, 2021 100%

Don't Pick on the Less Sexy

Their names were cute together which was only fitting because they were such a cute couple: Eric and Erica. Almost the same name, the same height, even their faces looked similar - his a masculine version of hers. Both were slim and attractive. Her hair was only slightly longer than his, and they ha... read more

shemale lover October 25, 2012 87%

For The Sensual

For the sensual, description is everything. The collar. The collar is custom-made; one of two; her request. This particular one matches the corset. The corset—the "bustier." The collar. Literally, no choker here. She is disciplined. Her collars merely evoke ownership. She belongs. Sh... read more

shemale lover November 14, 2012 50%

Francis to Frances

It was never my intention to go to live with Aunt Matilda and Aunt May, in New York state five hundred miles east of Arlsberg but when I was offered a place at Uni a short bus ride from their place that Dad suggested I should see if I could stay with them. Dad always referred to them as Aunt Mati... read more

shemale lover November 21, 2012 71%

all girls want breasts

All girls want breasts - a lifestyle Sissygurl and her boobs. Let’s start with saying a Sissygurls tits are important to her. Whether you call them breasts or tits it is the same thing. For all women, her breasts are a very important and visible sign of her ‘womanhood’ and regarded as a key a... read more

amberdoll September 14, 2020 50%

Why, She's A "He"!

Tina had mentioned to Dave a bar she’d heard about that catered to certain sorts of sexual adventurers and suggested she and Dave visit one night to check out the scene. A friend had described it to her and said she occasionally liked to go there with her husband. These two were old fashioned ... read more

shemale lover October 26, 2012 50%

Two hot CD lesbian sluts share an intimate moment

Her name was Kelly, we had met online in one of the gay chat rooms I like to frequent and for the next couple of weeks we had developed a friendship, exchanged pics and fantasies and I was really, really into her. we had a lot in common, more than just the mere fact that we were both gay CD’s ... read more

shemale lover June 21, 2014 86%

Tgirl trained to be the town whore to serve ALL Black men

A few years back I spent time on and off with several shall we say more dominating types of gentlemen One of them, who for this I shall call Leroy, just loved when we got together to make me totally helpless. It was our 6th or 7th meeting. Leroy and i had been chatting on Yahoo and when he f... read more

__tiffanylondontv__ September 30, 2014 88%

I Love To Love You

I Love To Love You Baby By Sabrina G. Langton Author's note: I have published this story on two other sites. I always said it was slightly aurobiographical, but reading it back it is a pretty accurate account of my summer of '88. There are only 3 things that I changed. 2 are itsy bitsy tiny deta... read more

Brina Giselle September 24, 2023 100%

First Time I Experienced Eating a Tgirl Out

So this is likely going to seem tabboo for some and if this is not your thing, I respect that but everyone is different. Eating pussy came natural to me like it does for most guys once they start having sex with girls. Other than one time 69ing with a female and having what I would call "incidental ... read more

AllenB October 21, 2022 100%

Would You

'Would you...?' 'Look the part to play the part....' 1 5' 4...dreaded, and to be dreaded....bookish, be-spectacled—damn near owlish....so much so that you might miss the way her tits spoke to you no matter how much she attempted to 'silence' them ....that you might miss the way her sk... read more

shemale lover September 23, 2012 66%

Camming Down the Rabbit Hole Ch. 09

As per my previous mornings recently, I stirred and rubbed the sleep from my eyes, that delicious feeling of my silk night ware stretching over my taught nipples and my morning wood throbbing in its lace enclosure. The urge to touch myself was palpable, it seemed no matter how hard I came the night ... read more

Dani_does_Dallas March 22, 2022 100%

Bikini Boy

I was the boy my father had hoped for after 3 daughters before me. Life in our suburban middle class two-story house was as normal as anyone else's. My dad was a loving father bringing me up and doing the things a father likes to do with his son – baseball, fishing, camping, working the garage... read more

shemale lover June 12, 2012 82%

First Night Nerves

My name is Timothy. I live in a large city in the English Midlands with my girlfriend Debbie. We are both 22 years old and have lived very happily together for over 3 years. We both work in a call centre for a large financial organisation. I am not tall – 5' 4" on a good day – and h... read more

shemale lover September 22, 2012 100%

Whatever It Takes?

It was a classic 'eyes meeting across a crowed room' moment when I met Penny. It was a Thursday night and I was at a corporate function where the firm I worked for were trying to drum up new business. Penny represented one of the companies that had received an invite. I had noticed her as soon a... read more

shemale lover December 13, 2012 100%

Amazon Archipelago

On the northern end of Stuart Island, in the far corner of the San Juan Islands in Washington State, an old lighthouse guards the broad, deep channel between the United States and Canada. No longer manned, the building and light tower stand empty now, replaced by a soulless but efficient solar-power... read more

shemale lover October 24, 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%