Free Shemale Stories

In the deep woods

Our forum star, Fran, wrote another little story for all of us and, although it doesn't boast any hardcore action, it's still very delightful. In the course of my job some years ago, it often took me into the deep woods. One day I was off in the foothills and thought I would be by myself so I was... read more

shemale lover March 29, 2015 62%

Kayla and Tracy: The Layover

Kayla and Tracy strode across the marble-floored lobby, their heels clicking across, and suitcase wheels rolling across, in rhythm as they walked up to the desk. They seemed incredibly out of place in the relatively quiet hotel room. Kayla, of course, always stood out, especially when platform heels... read more

shemale lover October 31, 2011 100%

An itch that finally got scratched

Hey all! New to the site, but have been a major fan of TS/CD etc since I was a teen. I remember always fantasizing about what it would be like if I was to ever get an opportunity to make the fantasy a reality. Well, I finally got that chance and took full advantage of the situation and I wanted ... read more

sizeman April 10, 2013 95%

My first foursome with shemales

I just want to say im a straight guy i love women but lately i have had dreams about fucking shemales, now im only 5'9 and have a 5 inch cock 6 inch fully erect. now i watch a lot of lesbian porn and im a little curious about shemales. now some girls i have fucked say im a great pussy lic... read more

LordLucian January 20, 2014 80%

Kiara's Xtra large treat

I have developed an interest in t girls with the XXL tag, black and Latino girls especially seem gifted in that department, so when I seen this horney bunny on an escort page I knew I'd have to check her stats. A dark Latino Kiara boasted an impressive ten inches, I pondered on my way to meet her... read more

Kinky Dee May 27, 2019 40%

Feeling Womanhood Deeply

It seems somehow that my desire for womanhood is the one thing that everyone says I can’t have, but who are they to say why I should feel a certain way or want certain things? I want the very thing that their closed minds crusade against. It seems that the thing that brings me the most joy is the th... read more

Regina10 August 26, 2021 50%

Shemale Free Chat And Sex Adventures

It was another day at work at the mall. Being a security guard wasn't exactly the most exciting job in the world: I'd sit all and maybe get a few calls about some punk kids trying to steal DVDs. I felt like my talents were wasted there - I used to be a competitive bodybuilder, evening getting into f... read more

shemale lover April 24, 2016 42%

A New Girl

Still half-asleep, I purred happily when I heard the curtains being drawn. I could hear the sound of rain beating against the outside of the window, but the poor weather was the last thing on my mind. Still barely able to believe my luck, I slid my hand down the side of my smooth thigh, delighting i... read more

shemale lover April 5, 2012 100%

Super Shemale Tube At The Waiting Line

The restaurant was crowded - everyone in Boston wanted to be there, and I waited for an hour at the bar, hoping to get a table for one. But was I watched my chances of having dinner crumble to dust and glanced at Super Shemale Tube on my phone's browser, a girl sitting next to me asked "Hey, yo... read more

shemale lover March 14, 2016 75%

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%

Yellow Polka Dot Bikini(s)

"She was afraid to come out of the locker. She was as nervous as she could be. She was afraid to come out of the locker. She was afraid that somebody would see. Two, three, four, tell the people what she wore. It was an itsy, bitsy, teenie, weenie, yellow polka-dot bikini that she wore for the ... read more

shemale lover August 22, 2012 100%

Lady and the Cop continued

The next night Regina got a visit from. Larry the cop who openly declared war on shemales and trannies. He was working a homicide where a trannie friend had been killed in her apartment. Larry was a known shemale hater and he never failed to express his opinions. Tonight he was in her apartment to ... read more

Regina10 March 6, 2018 100%

girls need a daddy

Friday July 18 Hello daddy, I have arranged to meet a man next week and we are in 'phone contact. He is coming to visit me and I just need to tell him whether Wednesday or Thursday. I haven't done this yet as once done is done .... I know he wants to take photos of me but I don't know if ... read more

amberdoll July 22, 2020 0%

My first time as a female

I was playing with my tiny dick one morning. Thinking what it would be like to have a pussy and some tits. Wondering what dick would taste like. These thoughts made me feel horny. I got a boner. K sneaked into my parents bedroom. Looking for Mothers sexy underwater. I found her panties and bras. I a... read more

2BWoman September 7, 2022 50%

Groped on the Bus!

In real life I do not crossdress in public, I am not yet comfortable being my true transgirl self, I wear normal men's clothes and I look like a guy. So I look very different from my persona here. So...there I was standing among dozens of strangers at a bus stop. I kept looking up from my phone ... read more

Chrissy Tunnell March 22, 2023 100%

Choosing From Shemale Pics Gallery

"You into shemales?", asked the man in Amsterdam's Red Light district, "We have everything in De Wallen, just ask", he continued to promote his girls, "Maybe the gentleman would like to watch some shemale pics gallery before making a decision?" And I thought - why not. ... read more

shemale lover June 30, 2016 71%

First Time With A Dominant

I had long been interested in BDSM, specifically female domination. After downloading a shemale dominatrix video by mistake, I became interested in a dominant shemale. I consulted the internet looking for something, and when my wife was away for the week for business, I finally decided to go ahead a... read more

shemale lover September 23, 2011 85%

Susan's First Time Part 4

The shadows of late afternoon crept across the city when Susan paid the cabbie off. Why had 'he' wanted her to come down to this neighborhood? She looked around with apprehension at the garish lights of bars and adult bookstores flashing in the growing darkness. One or two streetlights flickered on ... read more

shemale lover October 14, 2011 60%

Stephons first run in with Sora

I'm a young, attractive, slender, african american young man. I'm on my grind everyday. I like to drink, sleep, and fuck. I find that I can make any woman laugh until it is about that time to fuck. This is just one incident that proves this stament. Alright so I'm in one of my classes doing my re... read more

shemale lover May 24, 2012 100%

A True Recall of A Lustfull Evening

A memorable of the best evening of my life yet. My name is Sabrina I've been dressing as a woman often, as long as I can remember. One evening, while house sitting my parent's home, I decided it has been a long time since I was out as a woman, and had a good time. I started to let my inner wom... read more

shemale lover July 15, 2012 100%