Shemales Porn Stories
Page 8

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: 5486  |  
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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 2 years ago  |  Categories: First Time, Gay Male, Shemales  |  Views: 5438  |  
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taken in the woods and turned into a cock whore

Hello make sure you follow all disclaimers if you are under the legal age to view these items leave now; please leave feed back at Kellylbue66abc@yahoo.com

We just moved to an apartment in cherry hill nj which was nice from philadelphia.I got the place with my girlfriend and the place is a lot bigger and actually has a separate bedroom
which I can use for my office. I really liked the place cause it backed up to an area of woods and a little creek down this large hill. The apartment complex manager said it was called
a green acre site so nothing can be build on it and from time to time th... Continue»
Posted by kellyblue66abc 1 year ago  |  Categories: Anal, BDSM, Shemales  |  Views: 5439  |  
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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  |  Views: 5331  |  
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dressup sissy introduced to cock

When i was a teenager i lived next door to a guy named Gary. we were friends for years but drifted apart as he was 3 or 4 years older than me, so when he discovered girls i didnt see him for a while. However, one summer he and his then girlfriend had a fight, so being at a loose end he would invite me over to watch movies and play video games.
one day we were watching a movie, when Gary suggested watching some of his dads pornos. i eagerly said yes. so for a few days we would watch porno from about 10 am till 4 pm when his mom came home. his dad seemed to have hundreds of movies. one movie w... Continue»
Posted by hornyTVluvr 1 month ago  |  Categories: Fetish, First Time, Shemales  |  Views: 5329  |  
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The neighborhood sex slaves Part 2

Jack and the girls had gone home about an hour ago and I was in the gym working out when I heard the front door open. Kelly came bounding in calling out my name.

I told her I was in the gym working out.

Kelly sauntered into the gym wearing my favorite little black skirt and red tube top with a "cheshire cat" grin on her face. My cock stiffened a little when I saw her. She came over to the bench where I was now sitting up, straddling my legs and sat down. She looked at me in my eyes and said "I've missed you honey", "Did you miss me?"

Wrapping my arms around her waist, smiling, I said ... Continue»
Posted by Bigrodtaz 8 months ago  |  Categories: Anal, Shemales  |  Views: 5314  |  
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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: 5290  |  
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Bela



1_Revelation

”I like cock” she said in that strange nasal tone of voice. I looked at her askance.
”What?”
”Cock. I love it.”
”Thats what I thought you said” I said. Why was she telling me this?
Irena had asked if I could take Bela up to the hills and I’d agreed readily enough. Who wouldn’t want the company of a pretty young girl on a hike in the Upper Vidalen National Park? The sheer beauty of Norway laid out before our eyes.
I reached back and grabbed the thermos. I needed a moment to gather my thoughts.
”Tea... Continue»
Posted by Ijhel 19 days ago  |  Categories: First Time, Shemales  |  Views: 5278  |  
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"When I became a girl..." Pt 1

My name is Gabriella. Let me start by saying that I always felt like I was different growing up.  I was raised by a single mom because my dad left the country before I was even born and we never found out where he went or if he was even still alive. I was actually born a boy and I was known to be a very cute baby boy throughout my first two years of life. Even though I couldn't remember their first two years of life, as it usually happens to most people, I had still seen pictures of me from back then. In a few of them I was dressed in light blue and one of the pictures even showed my uncircumc... Continue»
Posted by adblman 3 months ago  |  Categories: First Time, Gay Male, Shemales  |  Views: 5223  |  
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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 COCK...my 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 5 months ago  |  Categories: Hardcore, Interracial Sex, Shemales  |  Views: 5217  |  
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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 1 year ago  |  Categories: Fetish, Masturbation, Shemales  |  Views: 5211  |  
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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 1 year ago  |  Categories: Anal, BDSM, Shemales  |  Views: 5203  |  
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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 2 years ago  |  Categories: Anal, First Time, Shemales  |  Views: 5198  |  
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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 1 year ago  |  Categories: Fetish, Gay Male, Shemales  |  Views: 5190  |  
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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 4 years ago  |  Categories: First Time, Gay Male, Shemales  |  Views: 5181  |  
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Camping and a Spit Roast

I went on a camping holiday with a small group of friends and it was awful, it was raining, muddy, and there was nothing to do but go to a pub that was nearby. So one night everyone's passed out d***k, and I'm wide awake so I go back out to the pub, and I stay there with my thoughts for a little while, everyone's leaving and it's all feeling very glum, then two girls walk into the pub. The one girl is fairly tall with a very curvaceous body and a noticeably large behind, while the other was relatively short with a much skinnier physique.

I don't really pay much attention, but then they stan... Continue»
Posted by wherethewhitewomenat 2 months ago  |  Categories: Anal, Group Sex, Shemales  |  Views: 5178  |  
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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 1 year ago  |  Categories: Interracial Sex, Shemales, Taboo  |  Views: 5175  |  
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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: 5173  |  
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Completely Fooled

I could not have expected the encounter I had the other night. Having recently separated from my wife a buddy and I went out to a local pub for a few beers. While we were sitting at the bar deciding what beer to try next a very hot redhead comes over and sits next to me. We exchange hellos introduce ourselves. Soon begin to talk about the different complexities of the beers we are tasting. She is so sexy with small b cups and a perfect mouth. After a few beers my buddy decides to take off leaving Veronica and I to get ourselves. She is just a darling; her smile, her laugh, her sensual demeanor... Continue»
Posted by IndieMe 6 months ago  |  Categories: Anal, Hardcore, Shemales  |  Views: 5160  |  
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My First Time With A Boy!

These stories always start out with "the summer after high school" or "my first semester of college" but it doesn't gravitate to the true experience felt when actually going through changes in your life....hormonal changes. So let's just say for the sake of this story, that I was a teen....and he was a teen, and a teen is 13-19 years in age. But none of that matters. What's important is that this time of my life was full of huge changes. Cross-dressing was not new to me at this point, and by now I had well broken into the habit of using my mom's make-up. I mean, every time I looked in th... Continue»
Posted by Ivygurl86 1 month ago  |  Categories: Anal, First Time, Shemales  |  Views: 5095  |  
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