Free Shemale Stories

An Exploit as a Paid Whore

I’m submissive by nature. Big surprise huh? I think most girls like me (I’m a transvestite) are. It’s funny but before I really got into the whole dressing scene and I lived most of my life as a guy I wasn’t all that submissive. In fact I remember being a little above average... read more

shemale lover November 16, 2012 100%

Lady In The House Ch. 05

A story by MicheleNylons (Crossdressed prisoner is forced into prostitution.) From Part IV Then Eddie looked down at my body and noticed the semen pooled at the front of my panties. My semen! He looked down at his tight belly and saw a slimy stain that was the result of my ejaculate spread th... read more

✘Transensual✘ February 25, 2019 100%

Nice to meet you. I'm anese Mistress Ran.

Since I've been in the BDSM world for a long time, I often experience novel-like reality. However I have a deep connection with a man dressed as a woman. It's been since I was a kid. A man who wants to be a woman. A man who really wanted to be born as a woman. I have trained many men li... read more

mig69domina January 14, 2021 33%

by a Shemale Part 3

I woke up the next morning not sure what just happened was real or if I just dreamed it than I looked around. I was laying naked in this mammoth canopy bed the bed spread and canopy were both pink and feminine and I realized it wasn't a dream I couldn't believe I was begging to be fucked. ... read more

shemale lover August 29, 2011 75%

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%

Clothing and the Nude

In The Erotic Eye and the Erotic Senses, Stefan Beyst observes that various gestures and poses have been designed to display parts of the body that would remain otherwise unseen. Erotic art is a striptease, he points out, in which, sometimes, nudity is revealed to oneself, as in a mirror. Whereas, a... read more

shemale lover September 10, 2011 50%

Kimberly Wilder: An Assessment

Pull up a chair. Oh. That's right. If you're reading this article, you're most likely at your computer monitor, which means that you've already pulled up a chair. Okay, good. In this article, I'm going to review the splendid art of a magnificent (and very beautiful, too, by the way) transgende... read more

shemale lover September 19, 2011 33%

Caught cross dressed Part 1

My name is Philip. I am married to a beautiful woman called Helen, and a few days ago... I did something very stupid! My wife, her mother, her beautician, my P.A. from work, and any of their friends, (in fact, anyone that they choose,) are now completely in control of my life. They are my Mistres... read more

shemale lover October 2, 2011 75%

and Daisies and Lollypops

One of the most intriguing television phenomenons of the past 10 years has been The Jerry Springer Show. From trash talking prostitutes to mother-daughter love affairs, the most shocking underbelly of American culture has been exposed to those who would never suspect. One of the recurring themes tha... read more

shemale lover October 24, 2011 50%

Lana: First Encounter

Well, I occasionally surf Craigslist in the Casual Encounters section clicking on the t4m button. More often than not I see the regular posts. No one over 35, big cock, muscular a +, face pic a must, no cock pic, 420 friendly, you must host, etc, etc. I wonder, ‘what are these people thinking?... read more

shemale lover November 11, 2011 100%

The Terrace View Apartments Part 2

The Terrace View Apartment complex was an impressive site, to say the least. It filled up two entire blocks on the far-west side of town. I actually passed right by it at first; thinking that it was a fancy hotel because of the ornate architecture arrogantly rising over the privacy fences that surro... read more

shemale lover November 18, 2011 100%

On the street with Luci

About a week after my fantastic session with Luci and Karen, I was walking down the street in the city. I got a text. It was from Luci. It simply read 'Stay there Ill meet you very soon.' Strange! I looked around and couldn't see her anywhere, so how could she know where I was? I stood and waited... read more

shemale lover January 23, 2012 100%

Been Caught Cheating Chapter 2

I awoke in the morning to voices. It was Angela and her sister Heather! I could here them in the next room talking, but couldn't make out the words. Everything was still dark though. And I was still bound to the bed, and gagged. I had stayed like that all nightlong. Trying to move, I also found that... read more

shemale lover April 23, 2012 100%

Bend That Gender

Shannon's Shocking Discovery Shannon leaned against Marilyn. She was definitely light-headed from her last drink. Marilyn's hand resting on her left hip pulled her closer, a move at once comforting and unsettling. She slid her arm around her new friend's waist, resting her head on the silk covere... read more

shemale lover April 27, 2012 100%

Brazilian Discovery Chapter 3

Chapter 03: Partying in Copacabana On the Ipanema beach, Barbara and Joan were joined by Tereza and Consuela. The beach was less crowded than the Copacabana one. Tereza pulled down her shorts and her T-shirt to appear in a quite hot red bikini, an uplift bra that was supported only by a band arou... read more

shemale lover August 25, 2012 100%

Brazilian Discovery Chapter 4

John, the husband of Susan (see Susan and John series) has travelled to Brazil for a one year training session. Mr Gupta has sent him as the pretty little Joan, in the hope he would lose any interest for Susan and leave him totally free to deal with his senior accountant! The corset maker had bee... read more

shemale lover August 25, 2012 80%

On the Run

“Your first mistake was stealing hundreds of thousands of dollars from me. Your second mistake was thinking you could get away with it.” As I stood trembling before his desk, Mr. Atwater regarded me as if I were a bug on the windshield of his Lexus. “Do you have anything to say for... read more

shemale lover September 1, 2012 90%

Brotherly Love, Sisterly Love Chapter 2

"RACHEL" My twin sister, and sometime brother, and I had been experimenting sexually with each other and crossdressing together for around a month, growing to love and to perfect our new feminine personas until they became the ones we thought of as our true selves. Whenever our parents ... read more

shemale lover September 28, 2012 60%

I Told You

“No, please…” I barely audibly whispered. “Shut up you little cum whore!” “So... ohh god, no... Fuuuuuuuck,” the words leaked through my painted lips. “You want that hole filled too, you little cocksucking bitch?” “No, please! ... read more

shemale lover September 29, 2012 85%

Alanya's Alternative Experiences

When i decided to write my blog i thought i would recall the early times of my crossdressing and how i started and how i felt emotionally. I suppose my first feelings of wanting to experience and develop the feminine side of my personality was when i became aware of the beauty of the a womens body a... read more

shemale lover December 9, 2012 66%