Shemales Porn Stories
Page 5

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 2 years ago  |  Categories: Group Sex, Shemales, Taboo  |  Views: 5726  |  
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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 10 months ago  |  Categories: Fetish, First Time, Shemales  |  Views: 5710  |  
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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 years..here 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 2 years ago  |  Categories: Fetish, Mature, Shemales  |  Views: 5681  |  
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Sissy story

Date: Thu, 11 Aug 2011 16:42:22 -0700 (PDT)
From: Danny Smith <bobber1945@yahoo.com>
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 9 months ago  |  Categories: Gay Male, Shemales  |  Views: 5592  |  
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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 month ago  |  Categories: Anal, Gay Male, Shemales  |  Views: 5547  |  
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Sucking My first cock

It all started earlier this week, I had begun to watch a lot of sissy hypnosis videos and training videos, mainly ones from Polish Mistress.

Every time I watch these videos, I usually would just end up masturbating or going on Cam/Phone with someone. But, after watching a 35 minute faggot hypnosis video, I was completely under the spell of the cock. My inner-desire took over after that.....and well this is what happened.

After being completely hypnotized, I went online and luckily enough found a dom daddy type guy in my area in a chat room. I told him I had never sucked a cock before, a... Continue»
Posted by pantycum666 1 year ago  |  Categories: First Time, Gay Male, Shemales  |  Views: 5450  |  
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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 3 years ago  |  Categories: Anal, First Time, Shemales  |  Views: 5437  |  
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My Neighbor and I first time!

Recently I had a college student move into the apartment next to mine. He was small, shaggy blonde hair, without any facial hair, looks like ever. Skinny with little muscle tone. We started talking while he was taking a break. I told him the normal neighborly bs. Then I went on about my day. Seen him and talked to him every now and then. I found out he just turned 18 and was on his own for the first time. We both enjoy sports beer and junk food.

One day I was walking by his window, I just happened to look in and saw a skinny ass in panties. Pink boy shorts, my first thought was good for hi... Continue»
Posted by thetodd83 1 year ago  |  Categories: First Time, Gay Male, Shemales  |  Views: 5417  |  
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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 9 months ago  |  Categories: Fetish, Shemales  |  Views: 5327  |  
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Seducing Daddy

I had started crossdressing when I was 5 years old when I went trick or treating as Princess Leia for Halloween. The first time I pulled on a pair of pantyhose, I was eight years old. I could not understand how a piece of clothing that I could crumple into the palm of my hand could cover my mother's legs from her toes all the way up to her waist. So I decided to try on a pair...and it was the most exhilarating thing I had ever experienced!

I began experimenting sexually with friends shortly after my twelfth birthday. It was 1984 and my father had recently purchased and brand new piece o... Continue»
Posted by cdsexslut 2 years ago  |  Categories: First Time, Shemales, Taboo  |  Views: 5250  |  
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My son got seriously hot

Well, life sucked after divorcing my little sheboy, he was everything to me, but I had to let him go see the world, he went to college, after leaving his job as a freelance babysitter to find himself, he was very good at his job, he worked as a babysitter for a filthy rich f****y, he used to make over £400 in 6 hours spread over a whole week, sometimes he takes overtime, however this overtime was more like parentsitting than else.

He would stay for a further hour to take care of the parents by getting into naughty games together, the couple were rather young, the man was just midway through... Continue»
Posted by starlight8998 5 months ago  |  Categories: Fetish, Masturbation, Shemales  |  Views: 5203  |  
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How I became gay pt 1

When I was in my teens I was only interested in girls and thought that being involved in a gay experience was completely disgusting. I never would have even thought of it if it wasn't for what happened when I turned 17.

On my birthday me and a few friends got fake I.D.'s and went to a bar in town. We all started drinking and getting as shitfaced as we possibly could. There was 4 of us and my three friends had all spoted the girls they wanted to fuck that night so I was left alone at the bar.

Within a few minutes this girl sits next to me and I immediately started checking her out. Sh... Continue»
Posted by Gayluva67 3 years ago  |  Categories: First Time, Gay Male, Shemales  |  Views: 5174  |  
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Fantasy cums true

I was on a business trip staying in a nice Hotel. After a business meeting in my room I called down for room service. The maid came up a few minutes later and I let her in. She was stunning, 5' tall with black hair and the bluest eyes I have ever seen. Under her uniform you could tell she was very well endowed at least a 34 DD. She came in and took care of the room. Thru small talk I found out her name was Terri, she was 28 and single. I thanked her and gave her a tip when she was done. As she left I had to watch her walk down the hallway, her little heart shaped ass swaying back and forth.

... Continue»
Posted by tittie-baby 1 year ago  |  Categories: Shemales  |  Views: 5171  |  
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The Room Mate

The Room Mate
My wife and I have been happily married for about nine years now. We had never slept with anyone else during our relationship. I have greatly enjoyed my time with her. However a few weeks ago a coworker of my wife’s moved in with us. Her name was Denise and she had just lost her job, car, and about everything she owned in about three days. We were glad to help her out in any way we could. We set up a second bedroom in our modest apartment.
At first things were normal, at least for having another person living with us. Then something happened, something I did not expect. I need... Continue»
Posted by raastible 1 year ago  |  Categories: Anal, First Time, Shemales  |  Views: 5166  |  
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My first time with a shemale



Let me tell you a little bit about myself I'm five feet 10 inches tall around
220 pounds, brown hair and eyes very muscular, I'm an ex-professional boxer.
Around 10 years ago I I was working as a bouncer erotic a nightclub in Fort
Lauderdale, when one night I heard a commotion in the parking lot. There were
several men beating up a beautiful woman, when I tried to break it up I ended up
getting very banged up myself.
Her name was misty, she thanked me for helping her and a... Continue»
Posted by palitro1 8 months ago  |  Categories: Anal, BDSM, Shemales  |  Views: 5170  |  
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mommy's new girl

It's true that I had become accustomed to drama in my f****y. My father was loud and mean, especially when he was d***k, which was most evenings and every weekend. He would back my poor mother into a corner of the kitchen and berate her, towering over her in that threatening way that I knew so well, telling her she was fat and ugly and stupid and spending too much money on me. He would get louder and louder until she finally began to tremble and sob – then he would storm out of the house in disgust, as if her crying gave him the right to leave his "silly emotional wife" and visit his drinking ... Continue»
Posted by momandboys 1 year ago  |  Categories: Fetish, Mature, Shemales  |  Views: 5137  |  
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Mom Transforms Son into a Transsexual.


I'm a very sensitive white teenage boy who's always been close to my Mother,but my Dad looked upon me with disgust calling me fairy,sissy,faggot, and other choice words, Father was a Marine he is six feet seven inches tall, black hair, Blue eyes, and a Alcoholic. My Mommy is six feet three inches tall, 42DD 28 44 inch frame, long red tresses that flowed over her Boobies and she like to show them off. My parents divorced two years ago he drifted off into alcoholism some place, I was watching porn on Moms computer checking out Shemale and Cross dressing web sites when all of a sudden I heard... Continue»
Posted by sissytimmy 8 months ago  |  Categories: Interracial Sex, Shemales, Taboo  |  Views: 5115  |  
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SUBMISSIVE HUSBAND CD



SUBMISSIVE HUSBAND

Chapter 1

Aas is usually the case, three years of marriage our love making had grown
a little stale. I decided that we needed something to spice it up and I
broached the subject of adult videos to my wife to see if she would like to
try something different. She was initially hesitant about anything
"pornographic" but I told her it was just "soft porn" and thought we ought
to try it just once. My wife is very strong minded and was raised very
strict so I knew it would be a big job to sell her on it but I kept after
her. She finally agreed and I stopped ... Continue»
Posted by aimen72 9 months ago  |  Categories: Fetish, Gay Male, Shemales  |  Views: 5066  |  
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Me, Mom and the Hair Dresser

Growing up as a only c***d I was smothered by my Mother, I don't know if it was normal ,but at 14 she was still breast feeding me,bathing me, and sharing one bed . I was a very shy boy, we moved every year so I was always getting beat up at the new school. I had no thoughts until my 14th birthday. It's funny how these things change so fast,I had received my first computer, I was looking up and typed in the words "Mother and Son" I was directed to a porn site one of the pictures was of a mature woman pegging a teenage boy wearing lingerie I got my first erection. So when Mom called me for break... Continue»
Posted by sissytimmy 7 months ago  |  Categories: Gay Male, Shemales, Taboo  |  Views: 5045  |  
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my girlfriend Allison has got a cock

MY GIRLFRIEND ALLISON HAS A COCK
I met Allison at a club she was by herself at the bar and when I looked at her I was smitten I knows that sounds cliche but it was like that for me! I sat down a few seats down and ordered a drink a whiskey sour I believe it was took a few pulls to get up my courage then I offered to buy her a drink and she looked over at me with these incredible sea green eyes and actually smiled at me "Ok " she said and ordered white wine which she sipped so sexily I asked her if I could sit beside her and she patted the seat next to her I couldn't believe my good luck to ... Continue»
Posted by pesty 1 year ago  |  Categories: Anal, Hardcore, Shemales  |  Views: 5014  |  
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