Free Shemale Stories

Tranny tricked the Postman

I’d woken earlier than I’d wanted for a rare day off from work and decided to see if I could have a little fun. So I did my make up and found the longest false lashes I had, touched up with the darkest mascara there is… with a touch of glitter… bright red lippy, a naughty smile, get the picture? ... read more

shemale lover December 3, 2014 66%

Sissy Femboy Chrissy in Drag 2: At the Apartment

This is Part 2 to the article I wrote called "Sissy Femboy Chrissy in Drag at the Club." In that story I explained how I am 41 but look, feel and sound younger, that I shave myself smooth and like dressing in gurly panties and other female clothes to be a sissy femboy for older guys. A guy I met on ... read more

Chrissy Tunnell February 3, 2022 100%

Sissy Femboy Chrissy in Drag at the Club

"Can you wear a dress tonight?" "I can't crossdress in public, I'm not 'out' and don't want to be seen that way." "That's okay. We're going to a gay-only club that has a drag queen show tonight, so you'd fit right in." "Cool, but I'll have to change when we get there." "Awesome! See you tonight!... read more

Chrissy Tunnell February 3, 2022 100%

My first time as a Femboy CD

My name is Nick aka. Nicole. I am a 20 year old gay femboy crossdresser and this is a little story of how I started dressing to become Nicole and my first sexual experience besides masturbation. I grew up living in an apartment complex with my mother and sister, who was 2 years older than me. M... read more

Nicole_femboyCD December 3, 2014 86%

My first time as a Femboy CD pt 2

David ordered me to dance for him and I hurriedly got off the floor and walked over to the radio and turned it on. I changed the station from an alternative rock station to a top 40 one, which was better for dancing. After I selected the station I moved to the center of the room and started to dan... read more

Nicole_femboyCD December 3, 2014 88%

How I became a cute femboy CD part 2

The game of husband and wife Kevin and I played went on for a little over 2 more weeks before we decided to go even further, I say we but it was Kevin who seduced me into it. We got together in our game as much as we could and it was a lot. I would always dress for him in various outfits and my ... read more

Cute_Femboy April 5, 2016 95%

My first time having sex with a Tranny

I have been obsessed with Trannies for as long as I can remember. There is something about a gorgeous feminine woman with a big thick cock that drives me crazy! I turns me on so much that I kept pushing myself further with my love for Trans women. I bought sexy dresses, underwear and heels to wear s... read more

Joe22lovests September 15, 2021 100%

Thursday night at the Gloryhole

So I went out to meet some friends on thursday, after a day of drinks we split or seperate ways. I started walking towards union square with the intent of grabbing a few drinks then heading home. As I got there I saw the bars were crowded so I started walking farther into the tenderloin not really w... read more

shemale lover June 19, 2012 100%

My Tranny Experience

Hey all I am about to tell for the first time my tranny experience! This happened last year on a trip with two of my divorced guy friends. We went to Costa Rica on a surf trip and while we were all single guys we took advantage of Costa Rica's night clubs and strip clubs and were having a very fun ... read more

shemale lover August 20, 2012 100%

Manusha Tranny at an adult cinema

Rajeshwari Theater in Bangalore!! An adult cinema which plays B grade sex movies, but more popularly known as a gay paradise for having open fun at the theater. I have been hearing about this from my top friends and CD sisters for quite a long time. Some of them had visited this place and had dif... read more

Manusha Tranny May 6, 2021 50%

A TRANNY FOURSOME & FIVESOME AT A GURLS PARTY DAY

At a recent TV gurls party, I was involved with a 4 and 5 way sex orgy held in a big private house near Brisbane AUSTRALIA. I arrived all dressed & fixed my make-up & hair as we chatted & gossiped over glasses of wine & some lunch. The other gurls arrived as we got re... read more

MISSJENNIFER April 26, 2019 77%

Roberta, Molly and Ed

Friday "Commander Cromartie?" Lt. Commander Edward Cromartie, USN, turned toward the voice that had spoken his name. He saw two female naval officers, a tall willowy light-skin Black woman, and a short Asian one. The Black one was wearing the uniform of a full commander, the Asian of... read more

shemale lover September 4, 2012 100%

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%

The Seductive Seed of a Tranny MILF

The Seductive Seed of a Tranny MILF SugarandSalt Jackson got home and immediately curled up in bed. He didn't want to move for the rest of the weekend. He'd finally worked up the courage to ask a co-worker out at work. She politely rejected the invitation. Then later on in the day, Jackson spo... read more

Gwapo67 May 3, 2022 100%

Joanna's day and night with Tania xxx

It took quite some planning, after our last meet in the lay-by, but at long last we had both been able to get away at the same time. We, well actually Tania, had arranged our meet to be at the Premier Inn at Witcombe, just south of Cheltenham and just of the A46. Tania was arriving just after lunch ... read more

Joannacd1 January 6, 2012 100%

Tranny Fuck

Its about midnight, and I'm horny a fuck. Couldn't find one of my late night freaks to come over and milk the cow, so i headed over to the east side to see what was going on at the strip club. As I get off on the exit, there's this long road that leads to the strip clubs. Its dark, on this side of t... read more

shemale lover July 18, 2013 90%

SHEMALE SEX IS THE BEST

I had been in sex with gays for 1 year, but had always been intrigued by those hot looking chicks who packed more than a pussy between their legs. I had no idea where to find one in Kanpur I was definitely bi-sexual, still seeing whores, and still going to gloryholes for my cocksucking needs. I w... read more

shemale lover March 7, 2014 93%

My Start

In the beginning, when I was younger and trying out my sexuality and starting to understand what I wanted and liked and craved and needed, I played with boys and girls. But in short order, I decided I wanted something in between. Which is how I would find myself sneaking into clubs in Manhattan in t... read more

Giantsquid January 14, 2019 83%

My TV Sex Adventures The Nightclub Whore

The bouncer of the biggest alternative clubs in the city followed me through the 3am streets as I drove to my motel. I imagined how this big guy was going to fuck my brains out. I had just finished sucking his cock in the coat closet and was shocked that he wanted more. I figured it would be a blow-... read more

shemale lover July 6, 2012 66%

Sex with security guard in the apartment..!

I always fantasize about exploring the unlimited possibilities of cross-dressing and exposing myself in public such as dressing up and clicking hot pics in public places, seducing men and get picked up from pubs, having sex in car and on the roadside, etc., and some of my fantasies have already come... read more

Manusha Tranny October 18, 2021 50%