Free Shemale Stories

Late Night Snack (Touch me in the morning)

I was awakened abruptly by someone banging on my door at 1am. At first, I thought it might be Harry, the man who replaced Mr. Cobb in my bed a few nights ago. He had been persistent and horny constantly. I think it was because fucking trans women like me was new to him and he hadn’t got enough of th... read more

Regina10 March 28, 2024 100%

Late night park visit

It was 11pm on a Friday night, I was driving my car back from a failed meetup with a guy I met online a couple of days prior. I thought it was going to be an amazing night, so I spent close to two hours getting my makeup and hair sorted to look pretty for him when we met. I was wearing a short black... read more

Natalie Bishop October 8, 2018 95%

Ladyboy Loves Up The Midwest

When Jasmine, a Thai ladyboy, moved into a small town in Iowa the locals didn't know what had hit them. She was instantly the talk of the town; initially for being so different and exotic but once she opened her club her reputation spread right across the county and state line. It was only a real... read more

shemale lover October 8, 2011 80%

Thai Ladyboy Interview

An Afternoon With Some Thai Ladyboys I spent this afternoon with 6 Thai ladyboys. No, don't go thinking that I tried them out. I didn't. I spent a few hours chatting with them, finding about them, trying to understand what makes them tick and learning about their experiences and the guys who util... read more

shemale lover August 11, 2012 71%

Thai Ladyboy goddes in Tokyo and a cheap love hotel

This is a real account of my meeting last week with a beautiful Thai ladyboy working at a flashy show at a night club in Tokyo. Written as a not to her. Hope you like it. You sexy ladyboy goddess, I must say you have the most beautiful body. When we first started drinking wine and talking ... read more

lblover77 October 9, 2012 100%

ladyboy Yaqi

After graduating, she began to wear women's clothing to work all day for a month. After Yaqi went to work in this company, she had to wear tight dresses and stockings and high heels every day. After a long time, she also got used to the close-fitting feeling of wearing pantyhose. More importantl... read more

Victor Chen March 23, 2023 100%

My amazing Filipina girl

Today's post is not a usual ladyboy sex story that we all got used to, but something more romantic, down-to-earth and non-porn. Thanks British Buy for sharing this story and being so brave in making your fantasies real and finding your true love. I wasn't looking when I found her. I wasn't reall... read more

shemale lover January 25, 2015 60%

Thai Ladyboy

One year ago, when I was 19 I went back to Thailand. The year before was to see the sights and explore the country, the second was more exploring and more fun, the third and final time was to get with as many ladyboys as possible. I had always been curious about trans women. Im not attracted to ... read more

BEN437 November 19, 2018 90%

Thai Ladyboy

One year ago, when I was 19 I went back to Thailand. The year before was to see the sights and explore the country, the second was more exploring and more fun, the third and final time was to get with as many ladyboys as possible. I had always been curious about trans women. Im not attracted to ... read more

BEN437 November 19, 2018 100%

Smoking ladyboy in latex indulges my fantasies

Our reader, Matt J, have recently visited Pattaya and, as you can see from his story, it was a very fruitful visit! He had a petite ladyboy Lo spend a night with him during which he came countless times, and now he says he'll be coming back for more. Who wouldn't? ;) I recently indulged a few of ... read more

shemale lover March 1, 2015 100%

Ladyboy surprise in Bankgkok

A few years ago I went to Thailand for the first time, my first stop was the bustling city of Bangkok. I had heard stories about the nightlife, the girls and the tourists. The country had never appealed to me that much but through a twist of fate I ended up visiting the city of sin for a couple of d... read more

Gracemel121 March 25, 2021 96%

Ladyboy Switch Story

I am messed up with how I feel about this. I still love looking at women. I love tits and arse. I like the soft feel of women – kissing them and feeling their bodies. I don’t look at men in public and get turned on – men with clothes on do nothing for me. Put me somewhere that I can see those same m... read more

shemale lover February 27, 2015 81%

Wedding Night Surprise

its my big dream to marry one women in our night wedding in the bed when i start to make her naked a discover i big dick between her legs wow she demand me to hide this secret and i accept ans she abuse to take me and more...... read more

BIG DICK HUSBAND December 6, 2018 37%

My late night dinner with Keilana Love

I maneuvered my car through the heavy traffic. I was on my way to see Keilana Love, the love of my life and the most beautiful woman in the world. Work had kept Keilana and I away from each other for the last two weeks. Longing to see my darling lent urgency to my trip. Keilana and I had planned to ... read more

shemale lover February 4, 2012 62%

Lay.. BJ Report #3

Lay Report #3 Real TS Encounters Lay Report (BJ Report) #3 Hey, So this is my 3rd official “Encounter Report” lets just say. This was early Saturday morning June 25th, 2016. Unfortunately, this report will not be that interesting/informative. I am writing it just because it did happe... read more

cngwriter August 2, 2016 80%

Late night hotel halls

I am 46 years old and travel quite extensively for businss. I dress in my hotel room at night when i travel. I sometimes entertain in my room. Sometimes I get very bold and wander out to the soda machine dressed sexily. Its about as bold as I ever get. I am quite tall and do not pass in public. Bu... read more

shemale lover April 24, 2012 100%

Late Night BJ

A few nights ago I was feeling horny and desperate for something to wrap my lips around. Flicking through the pages of various sex sites I found out there was a dogging spot close to where I lived, feeling a little nervous I decided to give it a go and see if my luck was in. I went to my 'slut' ward... read more

shemale lover May 18, 2012 100%

My First Night of Being a Sissy Cumdump

Well I first started dressing when I was about 14. One thing that I always noticed is that putting on slutty clothes makes me an absolute whore for cock and cum. Throughout High School I dressed in my alone time but never acted on my slutty urges from fear of being caught by my parents. When I moved... read more

shemale lover December 8, 2013 93%

A LadyBoy For My Wife

I have been happily married to my sexy Thai wife Lisa for three years now. My wife is Thai is petite (5'1") with a stunning figure, a tight ass and long waist length black hair. We had met in a bar in Thailand and subsequently we were married back here in the UK. She was very loving with m... read more

shemale lover June 23, 2012 81%

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%