Free Shemale Stories

My first time

My mother always said she wanted a daughter….my guy name was Adrian, so you could see where she was going with that. I was also a real sissy as a kid, terrible at sports, threw like a girl, did very few real boy things. My best friend and I discovered porn and masturbation together. My mom... read more

shemale lover October 22, 2012 100%

Highway in Heels

Highway in Heels By Sabrina G. Langton *Stories from the real world 1 This story is autobiographical. When I was 20 years old I used to drive a van for my parents from Brooklyn to Tarrytown New York once a week to drop off merchandise for retail shops in the area. I always had a full van on ... read more

Brina Giselle August 28, 2023 100%

He caught me in his wife's cloths

I do odd job's and I was about to do one for my wife's best friend Tina and her Husband Phillip. I went over and looked at the job. I told her it would take several days and that I could do the work while her and her husband were at work. That way I wouldn't be in anyones way. Well the first day of ... read more

shemale lover June 15, 2014 89%

Her First Encounter

Chrissie took him back to her apartment. He sat on her couch and sipped at his drink while easing slowly toward her on the couch. He put his arm around her shoulder; Chrissie felt so excited and felt her cock hardening. He started kissing her and pulled her close.Chrissie sucked on his tongue.One... read more

shemale lover October 27, 2015 97%

Karen In The Middle

Karen was on her hands and knees looking up at me as John pull up her skirt. He gently pulled her panties to the side and slid his condom coated greased cock inside her. She let out a moan as he slowly penetrated her ass. I admired her shoulder length brown hair, her painted eyes and red lips as she... read more

shemale lover January 11, 2012 100%

Campground Tour

I wanted to do something a little different the other night, so I decided to go somewhere I'd never gone as Karyn before. We have a resort area with several campgrounds not too far away, so I decided to take a late night stroll through one of them. I dressed down just a little – spiked stil... read more

shemale lover March 2, 2012 66%

A Job in the Theatre Chapter 12

Paula could feel her stomach as they pulled into the circular drive. She was nervous about seeing Sarah for the first time, almost more than seeing Ted. They got out of the car and were about halfway to the door when Sarah appeared. Paula smiled hesitantly. She could see Sarah's eyes go straight ... read more

shemale lover March 14, 2012 100%

Ana in Action

I had fantasized about him for months. I just wanted to know what it was luck to have him pulsing inside me, to feel his body pressed against mine in sheer lust. I just had no idea that it would actually come about and that my wife would be the hook up. You see, Jim has been one of my wife's drinkin... read more

shemale lover November 23, 2012 100%

Paula Herts UK and girlfriend in the woods

Paula and Girlfriend in the woods My ex gf used to have me dress up, go for a drive in the car, maybe to a truck stop or to the local woods. The 1st time she did it she had me dress up in sexy red lingerie, parked up near a local woods where people go to walk their dogs etc. She had me get out... read more

PaulaXD56 October 19, 2021 100%

Growing up CD Part 2

After we left Max, Peter and I fought over who would get to take the magazine home. We decided to tear out some pages so we could have some each. We agreed to catch up the next day and go to his house as his parent were going away for the week. That night after dinner I told mum (dad had left ... read more

shemale lover December 10, 2011 50%

Sex Ed Chapter Two

Over another drink, I learnt how David Lawrence had been dressing up as a girl since he was a teenager, always keeping it secret from his family and what few friends he'd had. He was shy around women and sex and had never had a girlfriend, instead he'd buried himself in his studies and dressing as a... read more

shemale lover March 10, 2016 100%

Wish cum true

My wife and I have had a strong and open relationship from the start. We have accepted each other and all our wild passions, and we have always been open about our sexual desires. Having said this I will try to express what happened the other night with the same intensity I experienced. I came ho... read more

shemale lover September 26, 2011 100%

Dressed in holiday style Part 2

I was up by 1 p.m., showered, changed into some fresh panties and donned some hated boy clothes to hit the streets. I stopped by a local coffee shop (not the national chain-brand type) and over a mocha latte the barrista was kind enough to give me a few pointers about where she thought the best holi... read more

shemale lover November 20, 2011 100%

Danielle's First Time

Danielle was born in the winter to 1976, but she was born a male by the name of Daniel. Daniel looked like a normal male child aside from liking girly things. Whenever Daniel would play dress-up he'd always dress in his mother's or his aunt's clothes and his parents thought that was cute until Danie... read more

shemale lover February 3, 2012 100%

Unexpected Secret

My neighbor and I get together almost every day after my husband goes to work. We have become very good friends. We go shopping, watch soaps, play cards, and cook together, all kinds of stuff. Her name is Linda. She recently revealed to me that she has a secret and isn't all that she appears to be. ... read more

shemale lover February 10, 2012 85%

Pippa's Story

I was just entering my prearranged destination. It was 11 pm and just before I paid the admittance fee, I stopped to look at myself in the mirrored walls. Reflected before me was a sexy, if a little sluttish looking woman in her thirties. The only discrepancy being that I was actually a 37-year-o... read more

shemale lover April 4, 2012 100%

Nikki in the Woods

About four days had past since my last fuck when I heard from the same guy again. I bumped into him at some local shops and we got talking and I could tell by the bulge growing in his jeans that my presence was having an effect on him. He hinted that he could go a quickie and luckily I had what I ne... read more

shemale lover June 12, 2012 75%

Online Mistress Chapter 1

My name is Kayla Andrews, I’m a closet sissy gurl who loves the color pink and everything femme! Nobody knows about my little secret except for my private online world. Recently I put out a craigslist ad for an online mistress and I got a response from a beautiful blonde woman who was looking for a... read more

CandyShopKayla February 16, 2016 100%

Kayla is back and horny AF!!! Needs boipussy filled!!

This goes out to all my friends and subscribers...Sry to u all I Haven't posted in a while. Life got busy. But I'm back and horny and craving cock pounding my pussy and in my mouth! I wanna taste ur delicious cum!! Feed me daddy! I want ur big hard cock inside my sexy little sissy pussy wh... read more

Sissy Kayla June 27, 2017 46%

Used in a hotel room

This is a recurring fantasy I have about being used in a hotel room. I’m working on making this a reality but for now this will have to do. I travel a lot for work and end up in many cities across the world. Usually I am out and exploring bars and restaurants. Always ends with me jerking off alo... read more

slvr2291 January 11, 2023 100%