Shemales Porn Stories
Page 8

Deer Hunting with Daddy

Every year, a group of my f****y members, mostly uncles and male cousins, all pack up our gear and head into the mountains every fall for the yearly deer hunt. I had been going since I was 5. All the younger cousins slept inside an uncle's trailer, while the adult's and older cousins slept outside in a tent. This tent was huge and was intended to hold up to 10 people.

One year, when I was 8, I was having trouble sl**ping. I left the trailer and went to the "grownup" tent. As I got closer, I could hear strange noises...grunting and moaning noises ;-) I quietly unzipped the tent, but only en... Continue»
Posted by cdsexslut 3 years ago  |  Categories: Group Sex, Shemales, Taboo  |  
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The heavy girl in the bar.

This is one of those stories from my past that I wouldn't consider rather astounding except for how it ends. It was a monday about 2 years ago. I was recently single and pretty horny so I figured my best bet aside from dating websites would be to go out to a bar and find a girl to hookup with. I hopped from bar to bar in town and everything was pretty empty with mostly men. I got to the last bar I would visit for the night, it was a bit more upscale than usual but there were a few women there. I flirted with them but they turned around at the bar and started ignoring me as if I didn't exist wh... Continue»
Posted by experiencedjojo 9 months ago  |  Categories: Fetish, First Time, Shemales  |  
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A Wife's Revenge

"What the hell is this!"

Michael Landers turned slowly toward his wife. She had been changing the sheets
on their bed when she came across an unexpected surprise. When the couple
finally stood face to face, Michael noticed his wife of three years staring
back, her left arm pointing straight at him with a purple bra dangling off her
index finger.

"Well, um, it looks like a bra," Michael answered.

"Ya think? Gee Michael, I never would have guessed if it hadn't been for you.
What I really want to know is who it belongs to and what it was doing underneath
your pillow."

"Wha... Continue»
Posted by lana100 7 days ago  |  Categories: Shemales  |  
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My shemale mother!!!!!!!!

I know there is a similar story similar to these but be assured, the other story only served its purpose as a catalyst for this one. This is a pure fantasy, the top fantasy that has been lingering in my mind for several it is....

I am 35 years old and had always been living with my mother, who is almost 50 since my father left us 20 years ago. I am not sure of the reasons but I do know that my mother is an average looking woman with nice looks and a not so fantastic body. Her pear shaped figure is a norm for any woman with Indian origin and what I do know best is her mammary g... Continue»
Posted by yarracuda 4 years ago  |  Categories: Fetish, Mature, Shemales  |  
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The special overnight bag

I did not want to have another boaring sales trip,so I packed up my special overnight bag for this trip. All the items a gurl would need to have a special trip. Inside were a few skirts some stockings and two wigs ( I can never decide)a few items so I could get clean and my laptop and camera.
After my sales meeting I went back to the hotel,took a long bath,cleaned myself and shaved everything smooth. Put on my make up ( this time I got my eyes perfect !) put on my stockings slinkey red skirt and this time I opted for the long black wig.

I felt so slutty walking down to the bar in the hotel... Continue»
Posted by sodeep2 1 year ago  |  Categories: Anal, Shemales  |  
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My Parents Had Gone Away on Vacation

My parents had gone away on vacation for a week. I was thrilled!

On my own for a whole week, free to do whatever I liked. And truth be told, what I liked was being nude, as well as dressing in women’s clothes. The first day they were away, I began enjoying my newfound freedom.

I am very slight of build, feminine really. My body is hairless save for in my crotch.

After dinner, I decided I wanted to enjoy myself nude. I turned off all the bright lights in the house, and left on a few lights that were dim. All the blinds in the house were open. I stripped off all my clothes and walke... Continue»
Posted by ssup28 4 months ago  |  Categories: Shemales, Voyeur  |  
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The Day Lana Turned Me Into Her Daughter!

When I was much younger my neighbor, Lana, a divorcee, kept an eye on me while my folks went out of town. It was she whom formally introduced me to cross dressing and it was quite to my surprise. Back then I could actually pass for a woman due to my build. My hair was shoulder length and my body was small framed with feminine features.
I used to try on my mother's panties and clothes even though they were too big for me. Lana, on the other hand, had a great body. She was athletic and did not have a huge chest or big ass. She had great curves and was well defined. When my parents asked if ... Continue»
Posted by lovetopleaseu 2 years ago  |  Categories: Fetish, First Time, Shemales  |  
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Leila Has a Big Secret

I'm an ordinary guy, nothing special about me at all. Well, maybe my choice in women could set me apart from most.

It all started one rainy afternoon in Northern California as I was driving home after a party I'd attended alone the day before.

I'd stayed over at a friend's house and after a nice leisurely breakfast I headed home so that I would be back home before dark. I had to be at work the next day and wanted plenty of rest.

I was driving along Highway 1 when I first saw her. And boy, was she a vision. It had been raining all morning and the woman who stood there beside the road w... Continue»
Posted by drew1207 1 year ago  |  Categories: Fetish, Sex Humor, Shemales  |  
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Sissy story

Date: Thu, 11 Aug 2011 16:42:22 -0700 (PDT)
From: Danny Smith <>
Subject: A Sissy Story Part 2

I got very excited writing the following story

I always considered myself straight. I was married and at 55 my k**s had
flown the coop. But over the last few years I began to fantasizing about
cocks and being submissive to a more masculine man. I was 6' tall fairly
trim at 175, but with a small 3.5inch cock. I never thought a lot about the
size of my cock until one evening while I was traveling I visit an adult
video arcade. When I entered one of the video booths, I s... Continue»
Posted by aimen72 1 year ago  |  Categories: Gay Male, Shemales  |  
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Crossdressers First Time

I was in my mid 40's and divorced and living a great life. I ran my own successful business from home and lived in a large house in its own grounds at least 5 miles from my nearest neighbour.
Whilst I was single I had an active sex life having been lucky enough to know 3 ladies who were unattached and had no need for a long term relationships but were happy to meet up for sex or go away for a break all no strings attached. They all knew of each other and I was aware they saw other men or ladies if they wished.
Debi was 50 a successful lawyer and very dirty. Helen was 60 a retired busin... Continue»
Posted by maninnylons 7 months ago  |  Categories: First Time, Gay Male, Shemales  |  
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My sexy wife has a secret

My wife, what can I say she is tall and leggy with thick, natural wavey orange red head with beautiful porceline skin and just enough freckles to tell you she is a ginger. Add to that smokey green eyes and thin sexy lips and you can see why people refer to her as Gorgeous Gwen.
From the time we started dating my friends all expressed their envy at me landing such a smoking hot piece of ass. She is a freelance writer for fashion magazines and on-line blogs so she is pretty dressed up where ever she goes.
I got home one Friday evening from an afternoon shift. I knew she was home because ... Continue»
Posted by triphammer73 1 year ago  |  Categories: Anal, Fetish, Shemales  |  
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Sissy for BBC use and a b u s e

My Dear little sissy s****r, lezzie lover and slutty confidant...

Thanksgiving saw me full of BIG BLACK mouth, my sissy pussy and my belly were full of so much BBC and SPERM from Big Black Daddy Dick (s) annnnd I was good little bitch in the Doggy position for the Black Daddys' and their DAWG POUND(ING). I finally hooked up with my own BBC GANGBANG SQUAD from the adult bookstore. They used me for well over 24 hours of serious sissy-slut abuse, degradation, domination, humiliation and more, much, much more! I can't wait to tell you about it. I wish you were with me so w... Continue»
Posted by santtxx 10 months ago  |  Categories: Hardcore, Interracial Sex, Shemales  |  
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Dinner with Brooke

Brooke texted me on my way home from work, “I’m making dinner, come down when you get home.” I replied back, “Sure, I’ll stop and get some beer.” “No bother,” she said, “I already grabbed some. Just you is all we need.” This was always nice to hear, and it was always nice to see Brooke. I felt so comfortable with her especially since the many last encounters. But I never think any more than what it is. Just dinner.
When I got home, I went upstairs, dropped my bag and headed down the front stairs to her apartment. Her door was cracked open a bit so I knocked, saying hello and opened the door.... Continue»
Posted by ahsleymills 3 months ago  |  Categories: Fetish, Lesbian Sex, Shemales  |  
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Tranny tricked the Postman

A true story…

I’d woken earlier than I’d wanted for a rare day off from work and decided to see if I could have a little fun.
So I did my make up and found the longest false lashes I had, touched up with the darkest mascara there is… with a touch of glitter… bright red lippy, a naughty smile, get the picture?

I put on some sexy underwear and a black lace top, little skirt with heels and hold-ups… I was on the hunt for cock but how could I trick a complete stranger into some naughty fun with a horny tranny??… I had a plan…

I was expecting a parcel in the mail that was too big for the... Continue»
Posted by JoanneCoxTV 1 year ago  |  Categories: Shemales  |  
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Panty Boys

By Fred Gingerman

Chapter One - Nerds United
My name is Mickey Donaldson. For most of my 16 years, the k**s have called me Mickey Mouse, because of my size and because of my shyness. I was only 5'3" and at 115 pounds, very skinny. My best friend Jeremy Haskins and I were always the oddballs. Jeremy was a little bigger at 5'4" and 120, but we weren't being recruited for our high school football team. Chess team was more like it.
We were pretty much classic nerds. Shy. Picked on. Ostracized. Intelligent.
But we were still 16-year-old boys and our hormones were stirring. Boiling actually. ... Continue»
Posted by BeeJay69 2 years ago  |  Categories: Fetish, Shemales, Taboo  |  
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more than expected teaching a neighbour to drive

It was a glorious summers day and I was chatting with my neighbour. he asked could i give her husband some driving lessons. Well I've met him but he is very quiet and so I thought this would be a good way to get to know him, so
"yes, when is the best time for him to go out" I asked
"He's home now if you've got the time" she said.
"Yes i'm not doing anything. Give him a call and i'll take him now"
So out he comes and I introduce myself and ask if he's driven before. "yes" he said so I gave him the keys and off we set.
His driving wasn't the best and I had to help him out quiet a bit. We... Continue»
Posted by xdrespauline 1 year ago  |  Categories: Anal, Gay Male, Shemales  |  
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Cruising The Drive In

It was a Friday night and all of my friends were at home with f****y. I was really bored and I asked my dad if I could take the van and go to the movies. He said it was ok and told me to be home by midnight.

The van was a 1977 Chevy van, it was brown in color and had the moon windows cut into the side. It had the typical "Captain' s chairs" up front and in the back had what you'd expect from a '77 van. It had a couch that turned into a bed.

Around 7:00pm I grab the keys and tell my parents that I was leaving and that I would be home by midnight. I walk out to the driveway, get in the v... Continue»
Posted by cockwhore_4u 1 year ago  |  Categories: Fetish, Gay Male, Shemales  |  
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The Body Shaper

My wife was always ragging on me about my posture. She said I slouched
and needed to stand up straighter and pull my shoulders back. I tried
to do that, but as soon as I stopped thinking about it I guess my
posture reverted back to what, for me, was 'normal' and then she would
get on me again about it.

We had been married for five years and I think her good cooking got the
best of me as I had gained about 20 pounds since the wedding. My
weight was her other pet peeve. If she wasn't nagging me about my poor
posture, she was on my ass about needing to diet and to start
exercising.... Continue»
Posted by kynthia77 1 year ago  |  Categories: Fetish, Shemales  |  
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My first cock-turned me bi

Most of my life I have been extremely hetero. I mean, absolutely no interest whatsoever in men. I have always loved everything about women, their scent, their soft bodies, their boobs, their muffs, everything. I could go on and on about how much I love women. I never, ever saw myself being with a guy. It just didn't ever interest me.

About 3 years ago, I was on a business trip that took me to Chicago. I was by myself in the evenings for a week. Anyone who has been on a business trip should know that after the work is done during the day, at night there is something about being alone and out... Continue»
Posted by Dionysus2 6 months ago  |  Categories: First Time, Gay Male, Shemales  |  
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My first time with a shemale

This is a true story, probably the wildest thing that ever happened to me. It happened when I was about 19 years old and lived in Hamburg, Germany. At the time I was one of those willowy, thin guys, little body hair and a healthy appetite for sex but not much experience yet. At a young age I discovered how exciting it is when I fondled and fingered my ass while masturbating and I developed a real fascination with anal sex.

At the time I used to visit a club ("disco" in those days) somewhere off the Reeperbahn, the famous red light district in Hamburg. One such Saturday I left the club in ... Continue»
Posted by HOLY-SMOKE 4 years ago  |  Categories: Anal, First Time, Shemales  |  
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