Free Shemale Stories

My new Experience with Amy Cute Shemale in Pune

Hi friends i am back with new story. I am mad shemale lover. and keep on finding new shemales for me. This time i got new website to search for shemale www.massagerepublic.com I saw an advertisement of Amy and i liked her. called her and fixed appointment. went to her hotel, which was ok ok ... read more

Stud4Shemale February 20, 2021 33%

Girl from Uncle

Tonight, I have to tell it all. It’s no secret that my uncle and I had a very special bond he had been eyeing me with those adventurous eyes from the time that I was 14 years old. And frankly I enjoy his ogling. I could feel my nipples get so hard when he looked through me with those alert and spark... read more

Regina10 February 14, 2024 87%

Backsliding: Tim's Story

Every man has a weakness, but not everyman knows what that weakness is until it is too late. The story I'm about to tell is something I'm not entirely proud of. My name is Tim. I'm a 22-year-old college student at California State University. I'm almost at the end of my senior year studying to be... read more

shemale lover February 9, 2012 75%

Bangkok Night with Thai Ladyboy Dancer

I was visiting Thailand back in the 90s and was blown away by the “Potpourri” of sites, sounds, and smells (not all of them good) of this city. Beautiful women were at every corner and very friendly to foreigners. I went out with a group of guys on the town after dark to check out the go-go bar scen... read more

AllenB April 20, 2022 100%

My Afternoon With Venus - Part I

It was a stunningly bright and clear Saturday morning when I left my house to head out and run some errands. Nothing big, just little odds-and-ends that had been building up that I needed to deal with someday and it seemed like this was as good a day as any ... little did I know how good the day wou... read more

funpics March 23, 2018 100%

Mai

When I was twelve I met a new classmate named Dave, he and I became great friends hanging out, joining clubs and what ever else high school kids do. His family was from the Phillipines and he and his sister were the first generation born in this country. His sister Mai is the focus of this story. ... read more

Zöe from Kingston August 9, 2018 95%

TG girlfriend is my new neighbor

With Christmas and New Year’s over, the weather here in Florida has become cooler, 45 degrees last night and it will be in the mid-sixties for the rest of the week. We live in a sub-division right off the waterway, very private. My neighbor usually comes down around Christmas and stays until tax ti... read more

Jon Paul January 17, 2022 100%

Sports Bar Pre-drink

Sitting on the chair leaning against the bar, Steven sat quietly sipping on his rum and coke. It was a fairly quiet night at the local sports bar he often ventured to after work to wind down from his work shift. Steven looked up at the door as a small group of women walked through laughing and ta... read more

Master VeeJay September 27, 2019 100%

How I became a ladyboy convert

Our friend Brian went to Thailand 3 years ago and had his first experience with a ladyboy details of which he would like to bring to Your attention now. He proudly tells he became a ladyboy convert after his first time and we have no doubt he did! On a trip to Thailand about 3 years ago I had my ... read more

shemale lover February 7, 2015 86%

Chinese Apple Turnover

I crashed harder than anytime ever in my life and my dreams were fucking vivid. I dreamt of being fucked. And of sucking huge cock and getting face fucked so hard that I was cock drunk and high from holding my breath so much. But so really horny from him doing that, so into that cock. Of Jax f... read more

ASSEaster5678 January 9, 2019 100%

Vegas Encounter- part Deux

Tuesday morning, it’s early and dark. Jack is in an Air BnB home in Summerlin, a suburb of Las Vegas. He met an online friend Diane and her friend/roommate last evening and we all slept in the King-size bed. I look around, Diane is sleeping curled in a ball on her side, but Holli is not here. M... read more

Jon Paul December 22, 2023 100%

Aby my trans daughter

I am 50 and great shemale fan. I met Aby through PlanetRomio during covid lockdown. I was alone at home that time and i was searching for some good trans or shemale. So Aby so my profile and sent me message. I immediately replied. we exchanged our contacts and then shifted our chat to Whatsapp. ... read more

Stud4Shemale January 3, 2022 91%

Big cock shemale from Pune, India

I just saw her profile on Planet Romeo, her name is ID is Kaynat / Muskan. I saw her photos and got attracted to her. I am always a big fan and lover of Shemales or TS. I called her and fixed appointment by negotiating with her for 2500 INR. I went to meet her, she stays in a condominium in ... read more

Stud4Shemale May 22, 2017 56%

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%

My first night was making love to a man

First .... My name is Lely Bella Calistia, of course it's the name when I decided to become Shemale. My age is now 28th, I became a shemale when I was 24th, when I first chose to be a shemale because I was obsessed with my ex girlfriend, after parting ,, .. maybe because I really miss her an... read more

Bella Calis March 13, 2018 75%

Exposure, Disclosure

The Greatest Liar, Exposure, Disclosure © Alexandra Rios 2019 Author’s Note: This is a continuation of the narrative which commenced with “My Awkward Phase”, which I posted here previously. Readers may wish to read that before continuing, although I have written them to stand alone. Natives s... read more

the greatest liar June 18, 2019 100%

My Sugar Daddy Fucked My Girlfriend...And I Joined In

I am a shaved-smooth, boyish bisexual male slut. At 43, I still look and feel young, and I enjoy the feel of and attention from older men, the older the better, 55 and up, with gray hair, wrinkles, and very hairy chests and bods. My Daddy, a 70-year-old White man that fits this description, "owns" m... read more

Chrissy Tunnell April 12, 2022 100%

Trannies in Space

There was no spaceport on Jansen's Planet. There had been, but whatever calamity had befallen the world generations ago had also destroyed its port. It was one of so many planets out in the Barrens that had fallen on hard times. So Dekker set down the Barnabas in a clearing in the forest, a remna... read more

ASSEaster5678 January 25, 2019 66%

The New Housemate's Secret

https://chyoa.com/chapter/Introduction.150836 The New Housemate's Secret How will you discover the hot new tenant's secret? Chapter 1 by Bauer1 The doorbell rings, a soft knocking accompanies the bell to break the silence of the house. You look up from your laptop nestled snuggly in your la... read more

Acche April 4, 2019 91%