Shemales Porn Stories
Page 11

My New "Girlfriend"

Let me introduce myself. My name is Kevin, I'm 23, I live alone in a two bedroom apartment and I work full time as a store manager. My last relationship lasted 3 years and we were together since high school but both of us split about a year ago. 

It was a long day at work today so I went to a local bar to hang out and meet hot single women. Once I arrived at the bar, I could see three hot looking women glancing at me, checking out my slim, somewhat muscular body. I walked over to one of the prettier looking ones and I said, "Hey beautiful, can i get you a drink? She replied, "I don't know..... Continue»
Posted by adblman 1 month ago  |  Categories: First Time, Masturbation, Shemales  |  Views: 3938  |  
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Dirty TS Supprise

True Story I'd been out drinking with a few mates first the pub then we hit the clubs. It was late and I had work then next day so left my mates and went to get a taxi home. walking up the street for a taxi I noticed a woman standing on the corner. The girl was facing away from me but looked hot from behind short skirt, fishnet stockings and high heels looked like a total slut my kinda girl. As I passed by she asked if I had the time of course I stopped and used the oppertunity to chat her up. She was stunning long dark hair brown eyes and tanned skinned after chatting for a few minutes she as... Continue»
Posted by crbigboy 2 years ago  |  Categories: Anal, Hardcore, Shemales  |  Views: 3930  |  
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MY FIRST SHEMALE ENCOUNTER

I remember the first time I found myself in bed with a shemale. I had just broken up with my girlfriend. I was lonely, I was horny, and
I had zero intention of finding myself in another relationship with a woman. When I told my buddy, Bob, he told me he knew just where to take me to solve this. So he took me to this club over in West Hollywood. The place was FULL of gorgeous women. My head was swimming - they were almost all slender and dressed in very sexy attire. Short skirts and sheer nylons everywhere.
"Wow!" I told Bob. "These chicks are all drop-dead gorgeous. What's the catch? Are the... Continue»
Posted by madnessx 2 years ago  |  Categories: Anal, Masturbation, Shemales  |  Views: 3912  |  
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Moms sissy becomes a young slut for a black man

I have always loved the feeling of something lacy or sexy on my body. I call it a passion of some sorts, wearing these things made me feel very special and desirable. I was raised by my mom and the closest f****y we had was my Aunt Trish and her two daughters. To start my collection of these things to wear, I would take things they left lying around the house and later claimed as my own since I assumed they were things that were lost. My mom was always working or going to my aunt's house on the beach for the weekend. I never was a problem k** and always made good grades in school. Mom never re... Continue»
Posted by momandboys 1 year ago  |  Categories: Gay Male, Interracial Sex, Shemales  |  Views: 3889  |  
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Jasmine cuckolds me

Hello, my name is Tim. I am a 30 year-old married man. I have been married for five years to my wife Danielle. She is an absolute beauty of a woman. I remember when we were married, I felt like I was the luckiest man in the world. Since I am no hunk myself, standing at just five foot six and extremely lanky, I felt like I didn’t deserve such a nice, gorgeous wonderful woman.

Let me describe my wife to you. Danielle is five foot seven, fair with blonde hair. Her bright blue eyes and charming smile are a delight to behold. Although she is 28, she has the body of a twenty year old, through reg... Continue»
Posted by leokingin 2 years ago  |  Categories: Fetish, Lesbian Sex, Shemales  |  Views: 3856  |  
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April My Shemale Love

April My Shemale Love


It seems that I dream of April quite often. She is the most beautiful girl I have ever seen. April lives in my building, next door to me. She is incredible. Her face is gorgeous. Her brown eyes are striking. She sometimes wears her long brown hair in a ponytail. I love the way it sways from side to side as she walks by. I love watching her walk. Her body is amazing. You should see her breasts. She has a full bosom. And they bounce when she walks. I love to see... Continue»
Posted by palitro1 11 months ago  |  Categories: Shemales  |  Views: 3853  |  
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my aunt made me a transvestite

My aunt and uncle lived two doors down from me when I was growing up. They had a son one year younger than me. We played together all the time and I was at his house or him at mine all during the summer months. My aunt was a big woman, she was 6ft. tall and weighed around 165. She was even taller in her 3 inch heels. She had long auburn hair with beautiful waves in it. She wore a 9 1/2 shoe. Her hands and feet were large, but so sexy looking with nail polish on. Her blue eyes would melt you. She had a great mirrored vanity she would sit at for hours and try different combinations of makeup. Sh... Continue»
Posted by momandboys 1 year ago  |  Categories: Fetish, Shemales, Taboo  |  Views: 3853  |  
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my first time




My mother always said she wanted a daughter….my guy name was Adrian, so you could see where she was going with that. I was also a real sissy as a k**, terrible at sports, threw like a girl, did very few real boy things.

My best friend and I discovered porn and masturbation together. My mom didn’t watch what we were doing too closely, so we used to jerk off down my basement like all the time. We would get a Playboy or some other skin mg and just go to town. He would catch his load in his hand and dump it down the sink (what a waste) but I would usually shoot my load on the floor(anoth... Continue»
Posted by adrienneheels 2 years ago  |  Categories: Shemales  |  Views: 3844  |  
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Hotel Encounter.

The man had met her at the hotel bar, away from home on another work trip, a little tipsy, a little lonely. She had smiled at him so sweetly and when she touched his hand it seemed inevitable that there was more to follow. After a couple more drinks he had followed her up to her room, away from the noise and the crowd.
She takes his hand and leads him into the room. They stand, holding each other tightly as they kiss, long and deep. She is wearing a knee length, black dress, belted at the waist with buttons running down the front. He pulls away slightly and then nuzzles her neck, kissing... Continue»
Posted by furrygurl 3 months ago  |  Categories: First Time, Shemales  |  Views: 3843  |  
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Caught in the Act....

One summer, my cousin Nancy came to stay with us for a while, as her parents had gone away on a cruise trip. At 18 years old, she was a couple of years older than me and in the full bloom of her young womanhood, so to speak. She knew it, too, and it was obvious that she had no problem at all in pulling any guy she wanted. Not only did she look good, but always dressed very sexy, just to make sure…

She was another of these girls I adored during my adolescent years, who LUVed to teeter around perched on very fine pointy hi-heel stilettos, and when she walked, her butt swayed from side to side... Continue»
Posted by caroletv31 3 years ago  |  Categories: Fetish, Gay Male, Shemales  |  Views: 3815  |  
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Poker Night Part 3

Everything was black. I couldn't see a thing, but I heard everything. ""Obey! Suck cock! You are a sissy! Worship cock! Obey your master! Obey!" over and over again. Every time 'cock' was mentioned a giant one flashed before me. And every time 'master' was said I saw an image of Craig. I didn't know what was happening, but after a while I accepted it. I woke up dizzy, my mouth open and dry. Sweat covering my body. "What was that all about?" I thought. It was morning. I got out and made breakfast for myself and Craig. "Goooooood morning" Craig said from behind me. I turned around to say good mo... Continue»
Posted by ConvertedGirl914 1 month ago  |  Categories: Gay Male, Shemales  |  Views: 3813  |  
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Alice 1

Alice

My name is Alan Smith, I am twenty two, about five foot six, fairly slim at just nine stone, my hair is dark blonde and fairly long, sometimes I put it in a pony tail. I have a degree in computer science, I work for an I.T. company, travelling around the southern half of England fixing computers and programming. I live with my dad Greg in a quiet suburb in Essex. My mum Elizabeth left us about four years ago, that was such a surprise as mum and dad got on very well, there did not seem any reason for her to leave, but dad and I have ... Continue»
Posted by ratty9uk 3 years ago  |  Categories: Anal, Shemales, Taboo  |  Views: 3813  |  
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An Evening With A Beautiful Woman And Her Cock

An older man finds an older woman and her cock at a Spanish class.

With winter coming to an end I was taking a class in conversational Spanish at the senior citizens centre because I planned to travel to Spain or Mexico next year. The people in the class were about my age, 60 to 70. I was fortunate enough to sit beside possibly the most attractive woman in the class. Unlike the others she dyed her hair a bright red and, come snow or sleet, she always wore a dress. For a number of classes we worked together trying out our poor Spanish until we could both ask where the toilet was, or order a... Continue»
Posted by smallfurrycreature 1 year ago  |  Categories: First Time, Mature, Shemales  |  Views: 3805  |  
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Daddies likkle baby girl

Once I had discovered that my role in life was being a sissy girl, I and my Daddy took our relationship further. I started growing my hair, who would take any notice, lots of men have long hair. I also allways had sheer stockings and satin panties on under my trousers when i went to work. I would join in all the macho bull at work talking about girls tits and the usual banter, all the time wearing more satin and silk then there fat ugly wives would ever wear. One day Daddy phoned me to say he was outside my office with a present. I went outside to see him in his car, he handed over a plastic b... Continue»
Posted by igglepiggle 1 year ago  |  Categories: Fetish, Shemales, Taboo  |  Views: 3799  |  
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My First Night of Being a Sissy Cumdump

Well I first started dressing when I was about 14. One thing that I always noticed is that putting on slutty clothes makes me an absolute whore for cock and cum. Throughout High School I dressed in my alone time but never acted on my slutty urges from fear of being caught by my parents. When I moved to college that all changed though. As soon as I got settled into my private dorm room, I thought it would be nice to spend the evening dressed like a little slut. I decided to wear my schoolgirl outfit that night. So I took a nice hot shower and shaved myself smooth from the neck down. I went back... Continue»
Posted by cumslutchloe 1 year ago  |  Categories: Anal, Hardcore, Shemales  |  Views: 3796  |  
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Caught by a neighbour in my s****rs clothes.

It was 10 o'clock on a Friday in late June of 1997. My parents were away visiting relatives for a few weeks. My s****r Kate had gone out partying with her friends for the night and wouldn’t be back till Saturday morning. Which left me all alone in the house.

For as long as I could remember I always loved dressing up in my s****r's clothes. When I was lucky enough to have a whole night with them out of the house, I usually went all out in my s****r's room. ??
I had been shaving what little body hair I had for years. I used to lie and tell anyone who noticed that a lot of swimmers and athlet... Continue»
Posted by kara_zor_el 3 years ago  |  Categories: Shemales  |  Views: 3782  |  
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First Date

My urges to be with a man had been growing every day, so I decided to start an online dating account, to see if any guys were interested in me. In a matter of hours, I received hundreds of messages from interested men. One in particular stood out to me. He was 6'5" and muscular and a former marine. He sent me flirty e-mails and I flirted back and sent him a few pictures. After about the 10th email he told me that he had re-read my profile and he didn't realize that I was transgender. He told me he had never been with a t-girl but that I was so sexy that he didn't even care, he needed to take m... Continue»
Posted by xjessica88x 2 months ago  |  Categories: First Time, Shemales  |  Views: 3780  |  
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Tina trap

A few days after he fucked me so masterfully that day, my friend's older associate invited me to visit him at his apartment. I wasn't sure what to do. Originally I had only had been with the one guy and now he seemed to be passing me on to his business partner. When I asked him about it he told me that he was OK with it. He had done this before: found a young guy and then introduced him to his older business contact.
So I had been used all along. I was just currency.
But I had liked how Mack - the older man - had fucked my ass. And I didn't want to NOT be fucked any more.
I accepted Mack'... Continue»
Posted by dlcalguy 1 year ago  |  Categories: Fetish, Group Sex, Shemales  |  Views: 3772  |  
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Abused as a tranny at a sex party with my mum

This story is a follow up to "Caught wearing my mother's stockings"

I decided to go to the party and be the tranny slut they were looking for. After all, it's nice to be wanted and I really would do anything to keep those photos of me dressed in my mum's stockings, private from my friends.

I've never had anything up my ass before, in fact I've never even had sex at all. This was going to be my first sexual experience. Unless you include being wanked off by my mum or kissing and groping fat girl, Stacey Williams at the school Christmas party. So the idea of being the centre piece at a sex... Continue»
Posted by petearch 3 years ago  |  Categories: Hardcore, Shemales, Taboo  |  Views: 3773  |  
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My First Girly Cock

It was cold. I was running fast so that I could not get too wet by the falling rain. The streets were quiet, because everyone was inside. It was twenty minutes before midnight. I was nervous. It would be my first time I'd have sex with anyone other than a woman. I love women. I'm in love with them. I don't consider myself being gay, but I always had that ardent lust to be with a transsexual woman. I just couldn't get them out of my mind.

This passion started a couple of years ago, while I was surfing on the Internet looking for hot stuff. Immediately I felt something. That first time, when ... Continue»
Posted by jimpgr 3 years ago  |  Categories: Anal, First Time, Shemales  |  Views: 3769  |  
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