Free Shemale Stories

First time with ladyboy / bottom

Hi everyone! now it is my turn to share my experience in Thailand. We were on a Christmas vacation on an island, and I didn’t even know ladyboy existed then. At a Christmas beach party I chatted and danced with a woman and we ended up in my bungalow. We kissed a lot and I knew that now I was g... read more

FoxyLover'ts October 6, 2020 81%

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%

Chinese Extremes Part 3

It was time to leave Mistress Ming's house and Lien was dressed, or rather tied up, by the two little sissies. First a brutal corset was fitted around Lien's waist, followed by a broad, black leather collar. Lien's hands were then tied in an armbinder, a black leather sack that held Lien's arms behi... read more

shemale lover January 17, 2012 42%

Chinese Extremes Part 1

Phil had been looking forward to the competition for weeks and now that it was over, he felt slightly disappointed. Not that he really had anything to be disappointed about. He had advanced to the third round in the Karate tournament where he had met an admittedly better opponent. So it wasn't that ... read more

shemale lover January 16, 2012 66%

Chinese Extremes Part 5

One morning Lien was one of three sissy-slaves were cleaning the slave toilets. The two others were using their tongues to clean the floor meticulously. Meanwhile Lien was using her tongue to clean the toilets. She was carefully licking the funnel leading down into the mouth of castrated toilet-slav... read more

shemale lover January 17, 2012 50%

Be My Bitch

After a long day at work, I get in my car, and look forward to the long drive home. It gives me time to unwind and relax. I try to forget about the hectic office and concentrate on my beautiful girlfriend waiting at home with that warm smile that she greets me with when I get there. However, tod... read more

Go Balls Deep or Go Home August 6, 2018 66%

My shemale weekend

I arrived at Chandra's apartment about 2pm. She greeted me at the door wearing a pair of short gym shorts and a tube top. She kissed me and let me in. My cock grew hard immediately and all I did was walked into the apartment. Chandra led me into the livingroom whenre her roommate Jizelle was sitting... read more

shemale lover September 5, 2015 82%

Chinese Extremes Part 4

The ride to Master's residence was completely uneventful for Lien. The whole way she lay in the trunk of his limousine, hooded and gagged, with her legs strapped together and her arms secured with the armbinder. The trip may have been uneventful, but Lien wasn't bored. She spent the whole trip fanta... read more

shemale lover January 17, 2012 66%

Chapter 2 - Cuckold Cruise

If you read Chapter 1, you know how I’ve been a weak, submissive sissy my whole life. My tiny nub of a penis never fully developed has never been inside a woman. I was fortunate enough to find and marry a strong and beautiful woman who accepted my submissive nature but only learned the full scope ... read more

Sissy Annabelle October 7, 2022 80%

Regrets. . . - by Katrina Electrika

When Mariana Cordoba was in her full blossom of being known in The Entertainment Industry, I was in China and Thailand having Lotus Mooncakes on Chinese and Thai New Years. . . The Orient is my Home now in life and I will be going back there very soon. . . but I have to say this, even ask Myself ... read more

Katrina_Electrika November 20, 2018 50%

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%

Me and 2 black men

Hello again this is EvA…I am a 40 year old tranny. I do not consider my self a crossdresser anymore, because I am doing that for so long that I have been transformed to a very sexy and feminine ladyboy. I have been taking also hormones for 4 years, on and off and I already saw many changes&he... read more

shemale lover June 22, 2013 80%

Becoming Alanna Part 2

Walking into room number one, she told me kindly to strip nude and climb into the chair. I did as I was told and hopped in to the chair. I fit my feet and legs into the stirrups and she spread them apart exposing my cock balls and asshole. She looked me up and down and smiled "not much work wit... read more

shemale lover July 12, 2012 80%

16 ladyboys jerked off in front of me! live!

Just got back from Thailand and had a very special birthday present. A big party had been arranged for me at my favorite ladyboy bar and a “competition” had been secretly arranged for me. Had a nice party with balloons, food, drinks etc then a midnight I was told that it was now time ... read more

shemale lover September 20, 2011 0%

Singapore tranny sex

My ship was dry-docked in Singapore for 3 weeks, n i was lucky enough to meet a gr8 girl first nite ashore, Lin, half chinese/ half malay, n fucking sexy. I slept at her flat most nites and the sex was awsome. She shared with a girl called Meena, a hostess on Singapore Airlines, but until this speci... read more

shemale lover November 20, 2011 75%

My Black Transsexual Goddess

Another day in the City of Ottawa, Ontario. Gosh I am bored. I walk through the corridors of the Carleton University library, yawning and stretching at the prospect of an all-nighter because my take-home midterm is due in the morning. As I make my way to my usual spot on the second floor, a wide-eye... read more

shemale lover February 21, 2013 84%

DATES NUITS

My wife, Denise, and I have been happily married for over 10 years. Over the years, we have enjoyed a vibrant and adventurous sex life. As we've grown in our marriage, we have become very open and honest about our sexual fantasies and desires. Through the years, we have come to realize that my w... read more

Femboy 2021 February 7, 2023 50%

Casino Girl

I had been working as a casino dealer for several years and would occasionally meet some very attractive women and chat. Asian women have always been attractive to me, whether the exotic appearance or maybe because my Mom was Pacific Islander, and a lot of people thought I was Asian. Mia was a bit... read more

Jon Paul January 3, 2022 100%

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%

First Time Having Sex With A Shemale

Ok let's begin so I was walking down the street going to the store one day I saw a woman and her daughter moving into a house they had some heavy boxes that they need help with. At first I thought she was white girl but when I got closer to them they we're Asian becuase i only saw the back and they ... read more

bigtranslover May 21, 2011 78%