Shemales Porn Stories

My step mom turned me into a sissy slut for dad

When I was in High school I would spend the summers with my dad and step mom. She was so hot and always dressed sexy, They were always very playful about sex, not like my mom and step dad. I loved the atmosphere.
During the week they would work all day and I would have the place to myself. I would always go into their room and see what I could get into. I found some picture of the 2 of them nude. Well after that I was always in their room jacking off to the pictures of my step mother naked. Little by little I would find other thing to help with my fantasies. I got into her dressed and wou... Continue»
Posted by firstknightd 2 years ago  |  Categories: Shemales, Taboo  |  Views: 21061  |  
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Auntie's Panties

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Auntie's Panties




I've always had this serious thing for women's' underwear. Even as far
back as grammar school I loved to sit on the ground in the school yard
to watch the girls jump rope and show off their frilly little panties,
just for me.

I was always so jealous of my s****rs! They got such pretty, pink
ruffled undies to wear while I was stuck with boring white BVD's. It
was so unfair, I thought!

I loved the exciting feel of their lace and silky nylon dainties, so
cool and silky and smooth to the touch. By... Continue»
Posted by aimen72 8 months ago  |  Categories: Fetish, Gay Male, Shemales  |  Views: 14296  |  
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A little favour

Day 1 – Friday

My neighbor Kathleen called me up one Friday evening and asked me if I could come over to her apartment and help her with something. She lives in the apartment next to mine, so I went over there. She was sitting at the kitchen table talking to a girlfriend. They were finishing up a bottle of wine and opening up another one. Kathleen invited me to grab a glass and sit down with them. We sat around the table talking and drinking wine. We drank that bottle and then another one. I was definitely feeling no pain.

Kathleen spun one of the bottles on the table. It stopped and poi... Continue»
Posted by stig1963 3 years ago  |  Categories: BDSM, Fetish, Shemales  |  Views: 14107  |  
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Photographer's Assistant

By Teresa Wood

Photographer's Assistant

It had been my mom's idea that I get a part time job, but I certainly
didn't argue with her. I was going to be sixteen in a few months and there
wasn't any other way I would ever get a car. Not that I really needed one. It's
not like there was anywhere I needed to go.
My name is Louis, just plain `Lou' to my friends or at least the casual
acquaintances I've made at school. The truth is that I'm a loner, I just prefer
my own company, and so my list of true friends is pretty short. Not that I'm
disliked or anything. I'm quiet and most of the... Continue»
Posted by jayymie 2 months ago  |  Categories: Anal, First Time, Shemales  |  Views: 14022  |  
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Adventures in Babysitting

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»
Posted by cdsexslut 1 year ago  |  Categories: Group Sex, Shemales, Taboo  |  Views: 13675  |  
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The pretty girl with her thumb out

It had been a couple of years since my wife left and I was finally starting to enjoy trips by myself. So that fall I through some stuff in the car and headed out to see things and clear out my mind some.

As I turned at the freeway ramp there was a young woman standing at the side with her thumb out. So I quickly pulled over and, with a smile, she hopped in. As we chatted I learned Chris had recently turned 18 and was using her new status as an adult to head north to see a friend. That worked out great since it was the direction I was already going for my trip.

Chris had long blonde hair ... Continue»
Posted by need2try 7 months ago  |  Categories: First Time, Gay Male, Shemales  |  Views: 13621  |  
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Neighbour fucked my s****r - but it was me

When I was 16 I stayed home alone for a week when my parents were on holiday. My s****r Jenny had just left home - she was 18. I'd been crossdressing for several years already, and I loved nothing better than to turn myself into a pretty teen girl in private. Fortunately for me, Jenny had left some of her clothes behind.

One night that week, I decided to play some dress up. I went into Jenny's bedroom and opened her drawers and closet door. I knew her clothes so well. What would I put on?

First I chose one of her bras. It was pink and heavily padded as Jenny had small tits. I put it on m... Continue»
Posted by pollyperverse 8 months ago  |  Categories: First Time, Gay Male, Shemales  |  Views: 13349  |  
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Caught cumming

When we moved into our new house I got first pic of bedrooms, instantly I chose the bedroom in the loft with a nice big skylight, I love having the sun in my room and when it's raining I like watching it drop all on the window.

One day I decided to have the blind open while I went to bed, waking up the next morning I had discovered my favorite place ever. I stripped naked and lay on my bed again, my huge tits flat on my chest as I lay there I began to wank. Where we had moved to was across the road from an all girls school, what I noticed was at the right angle I could see up under the bri... Continue»
Posted by shemalecharlotte 4 months ago  |  Categories: Shemales, Taboo, Voyeur  |  Views: 13075  |  
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Apartment to rent

When my wife suggested that we rent out the guest rooms above the garage to a college student it sounded like a good idea. It was very much like a small apartment, with a bedroom, bathroom, and small living room. No kitchen of course, but we could share ours and it seemed like a good way to make a little extra every month. We'd only recently gotten married and had just bought the house, so we could use the money.

Being my wife's 'project' as it were, I left the details up to her. I was working hard at my new job anyway. We were both just twenty-six then and recently graduated from the unive... Continue»
Posted by Alic91lovesporn 2 months ago  |  Categories: Anal, Hardcore, Shemales  |  Views: 12670  |  
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Mom the shemale bitch

Hi I have always had this fantasy

The fantasy starts out in high school a number of years ago, when I started having dreams of the kinkier kind, but not really understanding why. The dreams were about women that had big breasts and large hips as well as being tall and big boned.

The dreams always started out the usual way with a date, dinner, kissing, and petting, but as soon as I got the breasts out and satisfied that part, the girls were pulling down their pants for me, but not complaining I went straight for my goal.

The problem was that as the pants came down, the package would a... Continue»
Posted by frswriter 1 year ago  |  Categories: Anal, Mature, Shemales  |  Views: 12004  |  
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What If My Mom

Country Boys with a Difference

I loved my b*****r's cock, don't get me wrong, it's just what happened and our Mother loves our cocks as well as she loves our breasts. Let me explain.

It all happened when I was 13 and my b*****r was 11. Ours was a happy f****y living in the hill country of Kentucky, way back in the hills, but we were not 'hill - billy's'. Dad had a good job with General Electric, a aircraft designer and Mom was a teacher at the local high school. I don't know why we got sick but we did.
Bobby and me, boy did we get sick.

Dad and Mom were real worried I got told later... Continue»
Posted by chchboy 3 years ago  |  Categories: Group Sex, Shemales, Taboo  |  Views: 11432  |  
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HUSBAND AND WIFE USED BY MR. BIG BLACK COCK


We had decided to take a trip to Vegas and spend some alone time together.. We started off with dinner, then went to hit the tables.. My husband was on a winning streak. He was up at least $1500. I whispered into his ear have fun I'll be in that cute little shop. ok? Then his luck ran out.. and before I knew it, he had lost the money we had to get back home.I was so mad that i had to just walk away. About 15min. later I went back to where I last saw him but he was not there.Just as I was going back to the room I saw him at the bar with a high roller guy that had taken most of our money at ... Continue»
Posted by goodwifebad4black 2 years ago  |  Categories: Gay Male, Interracial Sex, Shemales  |  Views: 11193  |  
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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 2 years ago  |  Categories: Anal, Hardcore, Shemales  |  Views: 10886  |  
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Our New Life


Our New Life
By C. G. Drought

I was halfway between sl**p and fully awake effort to breathe. It is
being done for me. I can hear a mechanical sound that coincides with
every breath I take in. A click starts it and then the whirring sound
of an electric motor running.

The first few times I awoke to this sound I went through a period of
confusion and it still affects me that way but to a lesser degree. I
know the sound is the motor operating the bellows of the Iron Lung I
am locked inside. The feel of the leather straps holding my arms and
legs tightly to the... Continue»
Posted by klammer 1 year ago  |  Categories: BDSM, Fetish, Shemales  |  Views: 10849  |  
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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 1 month ago  |  Categories: First Time, Shemales, Taboo  |  Views: 10796  |  
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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 3 months ago  |  Categories: Anal, BDSM, Shemales  |  Views: 10413  |  
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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: 10319  |  
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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 2 months ago  |  Categories: Fetish, First Time, Shemales  |  Views: 9762  |  
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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 5 months ago  |  Categories: Lesbian Sex, Shemales  |  Views: 9723  |  
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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: 9565  |  
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