Free Shemale Stories

Loosing my virginity to Shemale Preet

This story is of may be 2017. When a shemale escort took my virginity n fucked me. I am not new to shemales. I hv been attracted to shemales since 1999 when first time I got internet at home. Suddenly while browsing i saw shemale website n instantly i was hooked to it. Well how I met my first ... read more

Stud4Shemale February 20, 2021 100%

Male or Shemale, Still a Slut

Part 1 My name is Brandon. I'm 18 (still in high school), 5'5", white with black hair, and rather feminine. I'm really slim with barely any body hair. All this has combined so that I'm not so popular with the ladies, which sucks cause I am one horny son of a bitch. Luckily, I'm rather fond ... read more

shemale lover December 20, 2012 100%

How Sia Shemale Pune fucked me ...

I met Sia through ts-dating . Called her n went to meet her. When I saw her I could not believe that she is shemale n has got cock between her legs. My god so beautiful feminine. Her implants are very sexy n make her more beautiful... Then I paid her n we went to comfortable small bedroom. I d... read more

Stud4Shemale February 19, 2021 50%

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 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%

A Little Girl Forever

Since I was a little girl I dressed in my sister's clothes, she knew it and she kept clothes for me and sometimes she bought clothes thinking about me. She was my accomplice and still is. When I was alone I dressed totally as a woman and I felt totally satisfied and realized as such, this included m... read more

Mabel Cecilia May 6, 2019 78%

Hung Trans Lesbians Fuck Two Ladyboys

Note 1: If you like Transsexuals, Trans Lesbians, Asian Ladyboys, Big Cocks, Extreme Cock Sucking, Anal Fucking, Anal Fisting, Semen Swallowing, Role Play, Orgies, BDSM, Cock Sounding and Foot Fetish this story is for you. Note 2: All the characters are over 21. The names are fictitious, but some... read more

darrell January 3, 2022 100%

Lesser of Two Evils

My name is Eric. At 21, I was working as the IT guy at a prominent Caribbean cruise company. My days were usually pretty boring. Fixing computer problems were usually a no brainer for me. People are so stupid when it comes to how they use their machines that I assume there will always be a need for ... read more

shemale lover March 27, 2013 84%

My Shemale Fantasy

Allow me to introduce myself, i’m a young European man, in my early twenties, writing my first erotic story. This has been a fantasy all my life, it probably will remain a fantasy, but that doesnt mean i cant write about it. Ever since i was old enough to realize my raising sexual interest and... read more

Jakester April 10, 2013 94%

The Girl Next Door Ch. 03 by derezzed ©

Chapter 3 – The Night Out Michael woke up on Monday morning feeling quite relaxed. The sun filtered in through the blinds towards him. He felt warm from the gentle rays. As Michael became more alert, he examined his surroundings. The feeling of silk sheets wrapped around him and Alexis's arm casu... read more

StevelovesTgirls June 11, 2019 100%

The game show,

One day i was looking through a number of competitions and trying to find a way to make some easy quick money. A number of applications were sent, mostly for junk i didn't need or for competitions I knew I had no chance of winning. For example, the types you get $30,000 for answering the easiest que... read more

chris1989r January 24, 2022 100%

First time shemale encounter

Lets start off by saying this a very true story, one that i love to re-live over and over. lets begin I was in el paso, texas..my girlfriend at the hotel. Something in me decided to go to the strip club. So i did. After a few dances, i decided to leave. I had always heard in mexico it was very ea... read more

iloveshemales112 December 17, 2011 80%

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%

Real Story with a Shemale Escort

One day I dreamt about a big black cock fucking me on doggy style. The dream felt so real that it made me to ejaculated in my sleep without even touching my cock. It was the first time this happened to me and I was surprised because I’d never felt gay. My underwear became a mess filling the whole su... read more

GusDark August 28, 2023 92%

A Shemale Vacation Part 2

We sat there staring despondently at the ground. We had searched through all our bags and pockets and had nothing like the money we needed to pay for the hot sex sessions we had each enjoyed with the hot, hung Dutch whore. The guy, the pimp, who had previously been all smiles and friendly encouragem... read more

shemale lover September 5, 2011 100%

Miss Bernie

My name is Bernice McDonald and I am the very happy owner/ operator of a couple of children's day-care centers. I love my life and I love this work. I love children and since I have one of my own this helps satisfy my need to nurture. I have not always felt or recognized this need. I was born in... read more

shemale lover February 22, 2013 93%

Mommy Adriana, I Will Obey You

Finally we were on our way home. Interestingly neither Mommy Adriana nor Mistress Andrea had cuffed or gagged me. So I just sat in the back of our car. During the short drive I had some time to think about what had happened in the past two days since my wife, err Mistress Andrea, and I had picked up... read more

shemale lover December 18, 2011 50%

The Visit

A visit to a hooker, where I describe my bisexual experiences *** It was a weekday, I had bummed off work and had made my way to Ipswich for a visit to Rona, my favorite hooker. She was a lovely woman in her forties, with a fantastic figure, not slim but not fat and with huge tits. She... read more

shemale lover January 26, 2012 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%

Sissy Slut and Stepdads

Frank was pumping me hard and his huge cock seemed to have grown and become extra hard. I am so thrilled that way he enjoys fucking my ass with such passion. I would almost think he was in love with me if this relationship wasn't so bizarrey. It’s ironic that as a male I always get total humiliation... read more

Regina10 November 30, 2020 90%