Free Shemale Stories

My Ultimate Fantasy...

Let me start with the details... I'm straight, 21 years old, and am probably no more than 7 inches long. But if I may say so myself...it's a perfect cock, thick and veiny and almost always pulsing. I have always loved my cock, and rather recently I began to realize that I could no longer stop at ... read more

bigtranslover December 25, 2013 63%

The Truckers Reststop

I had to work yesterday, it was Saturday,I had made plans to spend the day being the slutty little whore for the whole day, but work got in the way. I came home felt tried so I soaked in the tub, shaving my legs and puss yass and gurly clit. The weather was bad all day, when I finally decided to Fem... read more

bigtranslover February 7, 2014 84%

My Daughter and I Visit a Lesbian Bar

It is an extremely warm Saturday night and my eighteen year old daughter Krissy and I are sitting around in the house having conversation while we drink sparkling wine. Around midnight I suggest it might be fun if we took off our clothes and sat outside on the front porch. Krissy giggles for a few m... read more

shemale lover March 17, 2014 74%

The New Boss

My name is Jacklyn. I am 27 years old and was just promoted to Vice President of BB last week. I'm not a stunner but I have an okay body with a nice shape to it. I begin working here when I turned 20 and found it to be relaxing. However what everyone called the "Upstairs Crew" were very qu... read more

shemale lover March 19, 2014 67%

Alexis

Unexpected pleasure I was at a place in my life where I was done with the whole dating thing. All I did was work and hang out with friends. When a guy came my way to talk to me, I would brush him off quickly and rudely. I had a friend named Alexis. I would say she is one of the most beautiful wo... read more

shemale lover March 21, 2014 93%

Little cock convention

They came from all over the nation to downtown LA convention center. It was the "Little Cock Convention" I watched as men from all races and status came in. Sometimes they came with their wives,friends,Mistresses,lovers, or even their boyfriends. I was on Guard duty and walking the conven... read more

shemale lover July 7, 2014 100%

New boyfriend and first sex with him

Turns out the guy I sucked in the faculty (college) toilet actually suspected I was a trans and that turns him on. And not only he's into trans he also told me he loves BDSM. I don't have to tell you how great this is, but let's start at the beginning. The other day after the "toilet inciden... read more

shemale lover October 21, 2014 88%

My Great Adventure

One morning after dressing in sis’s clothes and she is a hot one.....black fish net stockings and 5” patenet leather pumps and corsets to die for and a pair of padded inserts to enhance her already endowed breasts, I needed some excitement besides the usual pulling of the wang and using ... read more

shemale lover December 19, 2014 90%

First time in Bangkok

If you have read my story about the first time I was with a TS girl then you know my experience was limited to just a few times. So about 4 years ago I went to Thailand to visit my buddy who was working there in a high profile job with the Thai government. We stayed in his apartment on the 40th floo... read more

shemale lover January 13, 2015 81%

Sleazy shemale fantasies

Sifting through the comments that readers leave at Trans Ladyboy, i have found two really hot shemale fantasies that I would like to devote separate space to. They are both written by two horny guys, wyocock and Eddie, who dream about being with shemales all days long (the only difference is that E... read more

shemale lover February 19, 2015 100%

Got more than he bargained for

This story was written for Trans Ladyboy by Brandi, a hot dominatrix and a phone sex operator. She says guys often call her to share their tranny fantasies with her, one of which would be getting dominated by a tranny, and, you know, she's really good at that! Call her for this phone fantasy (1.99 a... read more

shemale lover June 7, 2015 88%

My Preference for Girls didn't change

When I decide to finally go into my transition, I kinda felt I might think differently about boys. Well I guess I do some. I like gay boys or more feminine boys now than before I started trans, but I find I still like girls. Most trans girls I know now prefer to have sex with boys. Maybe I'm confuse... read more

shemale lover November 21, 2015 33%

My First Shemale

Let me tell you a little bit about myself I’m five feet 10 inches tall around 220 pounds, brown hair and eyes very muscular, I’m an ex-professional boxer. Around 10 years ago I I was working as a bouncer erotic a nightclub in Fort Lauderdale, when one night I heard a commotion in the ... read more

shemale lover February 10, 2018 81%

Butt Sluts

My name is Jimmy James. When I started high school, my parents shipped me out to boarding school to teach me discipline. They were mad because I had always been a disappointment to them. I wasn’t terribly manly and I liked to dress in girls clothes. The more often they caught me dressed like a... read more

shemale lover December 22, 2018 91%

Trans Bookstore Adventure

I was walking near the corner of Polk and Post Streets past an adult bookstore when I noticed an attractive transgender standing on the corner. I walked up and struck up a conversation. I told her she was attractive. She asked me if I wanted a date. I asked her if she was functional. Then I asked he... read more

shemale lover August 11, 2011 94%

My first time with a shemale

Let me tell you a little bit about myself I'm five feet 10 inches tall around 220 pounds, brown hair and eyes very muscular, I'm an ex-professional boxer. Around 10 years ago I I was working as a bouncer erotic a nightclub in Fort Lauderdale, when one night I heard a commotion in the parking l... read more

shemale lover August 23, 2011 100%

Meghan Chavalier

Meghan Chavalier is a transsexual entertainer and has starred in 150 adult films, has directed adult films, has written adult films, has appeared as a female impersonator, has written a novel, and has been a professional model. Meghan, has been called the most beautiful transsexual star by "... read more

shemale lover September 1, 2011 20%

Jo, Shemale Goddess! Part 2

Jo chuckled as the man in the sharp business suit looked hastily away when she looked up and caught him staring at her legs, again. Her 'Rupaul' legs as men with a history of watching men dressed as women called them, or her 'Naomi' legs as the newer ones to the scene seemed to think. Both divas had... read more

shemale lover September 5, 2011 0%

Transsexual Actresses Part 1

The adult entertainment market includes thousands of videos and DVD's featuring transsexual actresses. Some of the more popular of these celebrities have their own web pages. Brief profiles of some of these actresses, including a list of their films, appears after the initial list. Adriana Ventur... read more

shemale lover September 8, 2011 57%

Transsexual Actresses Part 2

On the way to Florida, in 1992, Meghan stopped in New Orleans, Louisiana. Her visit to this city lasted an unexpected five years, during which time she began her transformation into a transwoman. A popular nightclub, Papa Joe's, was looking for a replacement for a transsexual who had played Madonna,... read more

shemale lover September 8, 2011 25%