Shemales Porn Stories
Page 2

How it all began

My mother had 4 c***dren, 3 girls and a boy. I was the youngest. My s****rs were 5, 4 and 2 years older than me. Being the youngest I had to do as my older s****rs told me, including being dressed up as a dolly to play with when I was 4. When the oldest started wearing make up at 11, I was used for practice by all three of them, so I learned how to apply it myself.

When the oldest graduated from high school and went into the Army I was the same size as my youngest s****r and took to trying on her clothes. The feel of her bra’s & panties was awesome compared to my cotton tee shirts & briefs... Continue»
Posted by Andii18 4 months ago  |  Categories: First Time, Group Sex, Shemales  |  Views: 11720  |  
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My sister, my first, the tranny

A little something different to spice up your lives

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It was the first week of June and school was out for the summer, I was 18 and had just finished my senior year. One night while we were eating dinner, My Mom and step dad informed me that they were going away for two weeks. When they got married they did not go on a honeymoon, so they wanted to take one now. Jack, my stepdad, told me they were going to... Continue»
Posted by 6270daniel 12 months ago  |  Categories: First Time, Shemales, Taboo  |  Views: 11260  |  
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The Babysitter's Secret

Author's notes: I first published this story on Literotica in April of 2007. It has since been republished on various sites, both with and without my permission. I am the original author of this work and can easily verify this fact if necessary.

This story is a work of pure fiction. All similarities to persons living or dead is purely coincidental.

The Babysitter's Secret: Part 1

The story that I am about to tell you took place on a day that started out
very ordinary, but would end up as the least ordinary day of my life.
Until that particular Winter day, I thought ... Continue»
Posted by Desangel 3 years ago  |  Categories: Anal, Hardcore, Shemales  |  Views: 11078  |  
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Surprise



The Surprise Vacation


CHAPTER ONE - INNOCENT BEGINNINGS

"Did you take your vitamin, dear?" Ellen called from the
bathroom.
I rubbed sl**p from my eyes and picked up the pill bottle,
rolling a big tablet into my palm. "My horse pill? I'm doing it
now."
"Have you noticed any difference yet?"
"Nah. Vitamins are pretty much all alike." She'd gone on a
minor health kick a month before, insisting that I needed to lose
a little weight and take better care of myself. I hadn't
actually made it to the gym to work out like she was th... Continue»
Posted by klammer 1 year ago  |  Categories: Anal, BDSM, Shemales  |  Views: 10890  |  
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Going swimming with sibling

I am 18, I have a younger sibling who is 2 years younger than me called Emily. Even though she is younger than me and we both come from the same parents, she has a better body than me. She is curvy, taller than me, wider hips, small waist, amazing big round ass and huge tits. I'm a D but she is an E, almost F. She turns me on a lot, I know it's wrong but I get horny thinking of her naked.

We both love our swimming. Even though this is an awkward sport for me as I am tiny and it is hard for me to hide a big 8 inch cock. I usually tuck it between my legs pushing up against my ass, on top I wi... Continue»
Posted by shemalecharlotte 1 year ago  |  Categories: Masturbation, Shemales, Taboo  |  Views: 10704  |  
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school teen gay crossdresser first time sex

A young cross dresser's first gay experience
I was just a young boy then, senior in high school, horny as hell and dreaming of my first gay experience since sitting in my new red lace thong and white lacy bra and discovering the one porno in the house everyone kept hiding from me. I guess they thought my s****rs panty drawer held no interest for me......they were wrong.

It had been a great afternoon jacking off in my new bra and panties and watching my first porno when it happened, I saw the most beautiful thing ever, Peter north titty fucking a hot blonde and cuming all over her face. I w... Continue»
Posted by allisontranny 6 months ago  |  Categories: First Time, Gay Male, Shemales  |  Views: 10682  |  
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Caught by Neighbor

Caught by Neighbor


- 1 -

It was a beautiful warm day, and I had it to myself. My wife Sam was interstate on business for the week, and not due back for another five days. For me that meant housework to be done, but plenty of time to enjoy my own space, and entertain one particular hobby. I smiled to myself, and not for the first time, I stopped in front of a mirror and pulled my tracksuit pants down, admiring the bright pink, silky panties that I'd been walking around in all day.

I'd been cross-dressing for many years before I met Sam, but it really wasn't her thing. So I tended to ... Continue»
Posted by Femluver 2 years ago  |  Categories: Anal, Gay Male, Shemales  |  Views: 10314  |  
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A young cross dresser's first gay experience

I was just a young boy then, senior in high school, horny as hell and dreaming of my first gay experience since sitting in my s****rs red lace thong and white lacy bra and discovering the one porno in the house everyone kept hiding from me. I guess they thought my s****rs panty drawer held no interest for me......they were wrong.

It had been a great afternoon jacking off in my s****rs bra and panties and watching my first porno when it happened, I saw the most beautiful thing ever, Peter north titty fucking a hot blonde and cuming all over her face. I was besides myself I could not believe ... Continue»
Posted by alex_boycd 4 years ago  |  Categories: Gay Male, Shemales  |  Views: 9963  |  
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My Boss Tricked Me

I work for a cell phone company. Part of my job is to travel to cell phone towers and fix any problems they might have. I enjoy it but am on call most weekends. Now I consider myself a man in public but at home I love dressing up as a slutty tramp. I love the feel of lingerie on my body. I had a few experiences with a man but it was mostly mutual masturbation. My crossdressing is a secret to everyone except the few I have met online.

Most Friday nights me and the coworkers go out drinking. Just a bunch of guys out having a good time. One particular Friday I got really d***k and my superviso... Continue»
Posted by sissysadie 1 year ago  |  Categories: Fetish, First Time, Shemales  |  Views: 9834  |  
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A Visit to the Doctor

I hadn't been to the doctor in years. But after a minor health scare with a friend, I decided I should go and get myself checked out. I made myself an appointment with a doctor nearby for the following week and waited nervously to go.

I had been born a male, but for years I have been presenting myself as female. I was really passable too, the only problem was my, well, you know. Not many people knew of horrid past, and I wasn't going around screaming it from the mountaintops either.

On the day of my doctor's appointment, I put on pink lace panties that covered most of my ass, a matchin... Continue»
Posted by Bangbangtrain 1 year ago  |  Categories: Lesbian Sex, Shemales  |  Views: 9740  |  
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Horse Cock Girl 6


A few days after going to the club with Lucy and Scarlet, Amy was on her lunch break at work, thinking deeply. A lot of things that had happened or been said that night had stuck in her head and it had been bugging her since. Everything she was thinking about was to do with her relationship with Lucy and Scarlet.

She'd been thinking about something since even before the club: marriage. She loved Lucy and believed that Lucy lover her too. She was, however, wondering if, were she to ask Lucy to marry her, Scarlet might get jealous. Amy didn't want that, because both she and Lucy loved Scarl... Continue»
Posted by drew1207 3 months ago  |  Categories: Fetish, Shemales, Taboo  |  Views: 9631  |  
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Sissy out of control in the toilet

I'd describe as a fit rough looking submissive guy. Recently love to dress in panties and stockings and get interfered with....

One of the first and hottest experiences was in a quiet public toilet. It was about 3.30 on a summer afternoon and I'd had no luck down a nearby cruising area - which was unusual as it was normally reliable. The lack of action was most probably down to feeling slightly inhibited by what I was wearing under my shorts.

As I entered the cottage (as we call public toilets in the uk) and judging by the scurrying that occurred I'd interrupted a scene.

I went in ... Continue»
Posted by skins4skin 1 year ago  |  Categories: First Time, Group Sex, Shemales  |  Views: 9619  |  
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Baby Sitters Secret


The story that I am about to tell you took place on a day that started out very ordinary, but would end up as the least ordinary day of my life. Until that particular Winter day, I thought I knew who I was. I was Peter Fuller -- respected educator, devoted husband, loving father. I had never cheated on my wife, I had never lied to a friend, and I had certainly never slept with a girl that young before. All of that changed within a matter of hours. But you know what? I wouldn't change what happened for the world.

Years ago, I moved to the small town of Emberton, Rhode Island to take a job ... Continue»
Posted by drew1207 2 months ago  |  Categories: Anal, Fetish, Shemales  |  Views: 9596  |  
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Feminized my Mother

My Mother divorced my Father when she found him in their bed fucking a neighbor girl he was eventually sent to prison, ever since then she's been on this anti men kick. When I was 14 I came home from school and saw My Mother rinsing some dishes in the kitchen so I snuck up behind her and grabbed her boobs, she slapped me and said go to your room or else.

I awoke the next day ,took a shower, went into my room to get dressed and couldn't find any of my clothes, I knocked on Mother's door, she said "Come in dear" I asked where my clothes were she replied I threw them out your not going to en... Continue»
Posted by sissytimmy 1 year ago  |  Categories: Mature, Shemales, Taboo  |  Views: 9522  |  
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Caught

This is how I got caught masturbating and lost my virginity to my stepmom.
I was still in High School but had just turned eighteen, and was still living with my dad and stepmom, Beverly. I was ashy kind in school and did not get many dates, this lead to lots of jacking off. I did not realize it at the time but not only had my dad married a transsexual, but Beverly liked to sl**p around. I later found out my dad, liked it and enjoy hearing her tell about a how she seduced strait guys.
So I was watching some porn on the internet when Beverly walked in on me. I quickly changed windows and made ... Continue»
Posted by raastible 2 years ago  |  Categories: Mature, Shemales, Taboo  |  Views: 9195  |  
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Mom Loves Not Her Daughters

IT SEEMED LIKE the ideal time. Amy was at school and mom had gone to shop
about an hour before. I had waited purposely to make sure she hadn't
forgotten something so she would return right away.
I'd been thinking about it for a long time. I mean, I'd looked at mom
and s*s's stuff before. But that was only in the bathroom where they
sometimes hung things around or in the dirty clothes or even in the washing
machine if I had to load and unload it.
I went to s*s's room first. It was really pretty disappointing. I
mean, she had panties and one spare little training bra but that ... Continue»
Posted by BeeJay69 3 months ago  |  Categories: Shemales, Taboo  |  Views: 9101  |  
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First time getting caught wearing Pantyhose

When I was 16 years old, I babysat for my moms best friend. I had know Joanne (my moms bff) all my life, she was my second mother. and a single mother at that. And Joanne was smokin hot! Had thee biggest crush on her since i can remember. Joanne always wore pantyhose or stockings, and i mean always, one night i slept over at her house, i peeked in her bedroom and she was wearing a teddy and pantyhose, and ofcourse i had to masturbate, because like i said, she's a woman who gives an instant boner at first sight. Anyways, she had asked me to babysit her 2 boys on a friday night. Not a big deal e... Continue»
Posted by sissypantyhoseboy90 3 years ago  |  Categories: Fetish, First Time, Shemales  |  Views: 8927  |  
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Caught wanking in school

This was my first sexual experience as a shemale, I was still in school, I loved the girls in the school uniform, tight white shirts so thin it would show their bras through and tiny short skirts, some flared and some really tight too, I would always end up getting a cheeky view up some of their skirts and I couldn't help but stare as their tight bald pussies or their tight perfect little asses. I had to wear that uniform too and I always had to wear little panties to hide my big cock.

We had just finished a P.E (Physical Education) lesson and we had all come back to the changing rooms, as ... Continue»
Posted by shemalecharlotte 7 months ago  |  Categories: Anal, Shemales, Taboo  |  Views: 8877  |  
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First Time Having Sex With A Shemale

Ok let's begin so I was walking down the street going to the store one day I saw a woman and her daughter moving into a house they had some heavy boxes that they need help with. At first I thought she was white girl but when I got closer to them they we're Asian becuase i only saw the back and they hair was long that it cover their face so i didn't get a good look until they ask for my help with the boxes and 50" inch flat screen T.V. they had so i said yeah i'll help you then she was like thanks a lot it's was a nice home for her and her daughter. So we finish moviing stuff into the house and... Continue»
Posted by TheGhost08 4 years ago  |  Categories: First Time, Interracial Sex, Shemales  |  Views: 8640  |  
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Met 2 s****rs with a secret

Synopsis: First of all, I want to apologize. I konw it's been a really long time since I posted anything. I just haven't had much time to write. However, I think you'll find this story worth the wait.

This story is about a young man who heads off to college in New Zealand and meets two beautiful s****rs. Before long, a relationship develops between our hero and one of the s****rs. Of course, if you've read any of my stories, you know there's more to this girl than meets the eye . . .

* * *

I want to get one thing out of the way before I start my story: I'm not gay. It's not a denial t... Continue»
Posted by drew1207 3 months ago  |  Categories: Fetish, Shemales, Taboo  |  Views: 8513  |  
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