Shemales Porn Stories Page 2
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»
The Surprise Vacation
CHAPTER ONE - INNOCENT BEGINNINGS
"Did you take your vitamin, dear?" Ellen called from the
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
"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»
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»
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»
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»
This is the true story of when my girlfriend at the time and I had a threesome with a shemale off Craigslist. Enjoy
At the time of this story which was a couple years ago I was dating a girl named Miranda she was sexy,funny and kind of kinky which was everything I looked for in a girl I guess. We had been dating for about five months and after the third months we had begun talking about having a threesome with another guy or girl because Miranda and I are both bi... Continue»
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»
When I was 14, me and my BFF, Ashley, started our very own babysitting service. She made an announcement during church and we immediately started getting phone calls.
One day, Ashley said, "Come here...U gotta check this out." And she pulled out a handful of 20's. "Damn, where'd you get that?" I asked. "Babysitting," she said with a smile. I counted it...just a little over $200. "How'd you get $200 babysitting," I asked. Now, Ashley was the neighborhood nymphette and I was the neighborhood crossdresser and I soon found that babysitting services weren't the only thing that men in th... Continue»
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»
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»
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»
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»
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»
My name is Lisa and I am sixteen years old. I live with my dad and in a pretty nice apartment but we did have a house until my parents divorced and my dad let my mom have the house. My mom was always really rude to my dad and he just let her do whatever she wanted. Well eventually she had sex with a guy at her work and when my dad found out he divorced her. I can tell that its affect him way more then me because to be honest my dad is way to good of a person for her. The only good thing I got from my mom was her looks. Long dark hair, blue eyes and a tiny body that's developing quickly. I get ... Continue»
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»
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»
Being home for a longer stretch than usual, I was supposed to be watching a neighbor’s house while they were on vacation. About three days after they left, I noticed some activity next door.
I grabbed the key and walked over, pausing to listen at the door. I didn’t hear anything unusual, but I quietly let myself in. I could hear music playing softly in one of the bedrooms and saw the door was slightly ajar.
A slim blonde wearing a fishnet halter dress with attached stockings was dancing in front of the mirror. She had a very tight body and I was enjoying the view as she swayed seductivel... Continue»
It had been a long time since I last saw my b*****r.he was actually my stepb*****r, but it didn't matter.we had seen each other naked a lot of times, but still he didn't have any sexual interest in me.but me, I wanted him to fuck me.I was pretty young back then but still I bad lost my virginity and already had 2 daughters.as my b*****r entered my house kt was 11 o clock and no-one was home.but very soon I came home, and after seeing my b*****r I gave him a big hug.this made my books press against him and as my legs were touching his cock I cud feel it growing.I looked at him and blushed, he th... Continue»
I came home early from work one day and didn’t know anyone else was home. As I walked up the stairs toward my room I heard noises coming from upstairs and as I got closer I could hear they were coming from my room. When I turned the corner at the top of the stairs I could see my b*****r’s best friend sitting on my bed, but I did not see my b*****r. That is until I walked a bit farther.
I stood back from the door a bit and watched the show my b*****r was putting on for Jason. My b*****r Steve was wearing my short black skirt and hot pink tank top, the red wig I wore on Halloween. Steve made ... Continue»
Black Man's White Pussyboy
Story from the perspective of a white pussyboy who gets fucked and dominated by a couple of nigger bucks. He also meets another pussyboy but ends up getting fucked by everyone. Good dialog.
I let Jay into the apartment. He was looking for a one bedroom,
furnished place and had called about my ad in the newspaper. I hoped to
rent this place quickly, then I would be full and could devote my time to
some maintenance and repairs rather than showing places. I looked at the
rental application he had filled out just a minute earlier. From the date