Free Shemale Stories

Betrayed Chapter 10

I would have loved to be waiting at the gate at O'Hare when Dianna de-planed from L.A. that Sunday night. I had to settle for the Baggage Claim Area. Those people working for the Transportation Security Administration have no sense of humor. I guess at eight dollars an hour, they can't afford one. T... read more

shemale lover May 30, 2012 100%

Bisexual Black Man's Paradise

The name is T.J. Brown. I'm an engineer working at Walpole, the toughest correctional facility in the state of Massachusetts. My days are spent reading books, exercising and occasionally tussling with other workers. The facility is undergoing some expansion and I'm the lead engineer on this gig, wor... read more

shemale lover June 24, 2012 80%

Caught Cheating Chapter 2

By this time, Hailey had taken the bus home and was punching in the code to her apartment building when her phone rang. Removing it from her purse, she answered it. Her friend Samantha was asking if she could go to the mall tomorrow. Hailey said sure but told her that she had to be back before 6 o'c... read more

shemale lover October 7, 2012 100%

My sexy Shemale Cousin

This is 100% True and whyim cumming in my pants while writing it This weekend on my birthday My sexy ass cousin came over I Loved my cousin From the first day i saw her And that was also the first time i beat my dick to her And i Knew she loved me cause i always saw her hold her crotch every tim... read more

TheKingOfLadyboys January 27, 2014 56%

TG Girlfriend moves in (part 2)

My wife Lydia and I have been married about 9 months, we have a very close TG friend, Joanne, that lives next door and every once in a while, we get together, and all go out and enjoy. We have had sex together, and when Lydia is away Joanne, and I are together at every opportunity. Joanne and I work... read more

Jon Paul January 21, 2022 80%

PRÉDATEUR ET PROIE ⚧️ ⚧️

C'était il y a entre deux et trois ans, bien sûr, quand j'ai rencontré Kitten pour la première fois. Ou plutôt Taylor. Ou plutôt sa mère. C'était un vendredi soir et je faisais le tour des bars, faisant passer de l'herbe, des pilules et des trucs plus durs. Je travaillais habituellement d'un bout... read more

Femboy 2021 April 26, 2023 50%

First work day!

Having just graduated from college in Miami I took up fashion as a career! Impressed? In fact, I managed to land a job as a clerk in ready-made clothes shop. Sounds not as impressive as I’d like to have but that is just a beginning. You think there are no other interesting places in the whole ... read more

shemale lover May 31, 2014 100%

Lady Blue

“Blue-eyed boys always get me in trouble,” she said in a sultry tone with an equally sultry smile. I smiled as I looked into those warm brown Latina eyes, so soft yet full of mischief. “I’ll be back in a sec guys,” said Tracy as she got up from the table and headed ... read more

shemale lover November 13, 2014 94%

My Filipina transsexual penpal

I too feel very attracted to Ladyboys, especially Asians. Since I started looking at the Ladyboy sites a part of me feels deperate to one day date, and maybe even be with a transsexual the rest of my life. I feel that I will never be sexually complete until I have finally had sex with an Asian Ladyb... read more

shemale lover July 3, 2015 50%

Victoria

I started towards the local theater in my Chevy Corsica to see the midnight showing of some sort of vampire movie. I guess it was a love story where this one girl falls in love with a vampire and vice versa. Oh well... supposedly the books were popular, so might as well see what all of the hype is a... read more

shemale lover May 8, 2016 95%

Shemale Dating

We arrived late in our hotel room. The date was going well... but I didn't know what to expect, being new in shemale dating - I was excited and a little scared at the same time. She was a beautiful Latina: busty, dark exotic skin, fantastic lips; we couldn't stop kissing each other in the elevator. ... read more

shemale lover February 12, 2017 69%

We’ve First Met Her At Shemale Chat Room

I know it’s lame. Being a regular visitor at a shemale chat room is not something that I was proud of. However, I live in a small town and I can’t just go out and find a shemale. And I craved one so badly! It’s kind of embarrassing for me to talk about it now, but at the time I ... read more

shemale lover August 11, 2011 100%

Down and Out

Our divorce had been final for three months. I was devastated, my wife had been sleeping with her boss for a year before she finally got the courage to admit it and ask me for a divorce. I felt horrible. I stopped exercising and started eating poorly, gaining more than twenty pounds. I felt like a l... read more

shemale lover September 14, 2011 83%

A Slut Awakens

The day began like any other; I woke up, showered, wrapped my towel around myself and sat down to begin applying my makeup. I stared at myself shocked at the transformations I had undergone the past few weeks, my beautiful feminine body so smooth and curvy it could put even the most finely molded ho... read more

shemale lover October 31, 2011 0%

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%

A Lady Indeed

"Blue-eyed boys are always getting me into trouble," she said in a sultry voice. I smiled, as I looked into those warm brown Latina eyes, so soft yet full of mischief. "I'll be back in a sec guys," said Tracy as she got up from the table and headed towards the ladies room. ... read more

shemale lover February 12, 2012 100%

Different

Rosa was hearing things now. she was in the cell her new owner had put her in, a dark, damp, dungeon, and could see almost nothing. tied to the wall, a 10 inch dildo stuffed into her anus, a 9 inch in her mouth, and a chastity device on her newly aquired penis, nipple clamp on her tits, and every on... read more

shemale lover February 21, 2012 100%

A Real Fantasy

It was a boring Wednesday evening. I was away from home on business. With nobody to talk to and nothing good on the TV I decided to go for a walk. I walked for a few blocks and noticed the neighborhood was changing from hotels and bars to strip clubs and adult bookstores. I had never been to a strip... read more

shemale lover May 28, 2012 100%

Big Daddy

BASED ON ACTUAL EVENTS As is the case with most hard drug users, you start off small and end up making your way up. Since I was 15 I had been smoking weed. One of my friends had introduced me to some other drugs like meth or coke a few years later. The weed was still a big influence but it all se... read more

shemale lover June 9, 2012 90%

A Special Girl

Please allow me to introduce myself. My name is Steven Brun. I'm a young Black guy living in the city of Boston. I recently graduated from high school and started college. I go to Boston College. It's a school full of rich white kids but I'm liking it so far. The city is big, much bigger than the sm... read more

shemale lover June 30, 2012 100%