Shemales Porn Stories
Page 12

My first time-an unexpected pleasure

I spent the summer of 1983 in New York with my dad and stepmom. I was 18 and was in between my freshman and sophomore year of college. I had a cool job as a bank messenger on Wall Street and plenty of time on my hands. I used that time to hang out in Times Square which, at that time, was porn heaven. Many hours were spent looking at all kinds of loops in the peep booths. Everything from guy/girl, lesbians licking and sucking sweet pussies to shemales and crossdressers. I had seen my first shemale photo spread a couple years before in an issue of Hustler and was instantly intrigued and turned ... Continue»
Posted by Blackpapi65 2 months ago  |  Categories: Anal, First Time, Shemales  |  Views: 3955  |  
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First time giving a blow job.

I was a bit younger than I am now when I met a boy a bit older than I was who just caught my attention. He was a closet gay, I was bi-curious. He was so attractive. 6'1", 80kg, tan, short hair, brown eyes with a great fashion sense. For now, we can call him, Joey.

My friends and I were out clubbing one night when we stumbled upon Joey on his own at the bar. My friends were more interested in dancing, but I wanted to sit with him and see what was up.
We chatted about minor things like school, parents and our sexuality. He was the first person I told that I was curious and I was the first to... Continue»
Posted by ShulaV 1 year ago  |  Categories: First Time, Gay Male, Shemales  |  Views: 3947  |  
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Dad uses me for his wife

After a long and unstable marrage of 20 years, the divorce papers finally came. My wife and I only had one c***d, William, and he is very gay. My wife was too much of a homophobic bitch to support him. Even when he was younger we knew he would turn out gay. Always wanting to wear girl's clothing, dress differently, speak differently, even walk differently. I always supported him as a dad and as his friend. I never understood and I still don't understand my wife and how she could just leave her only c***d and I. I remember it was his 18th birthday, about five months ago. She came home from work... Continue»
Posted by nicoleinberlin 1 year ago  |  Categories: Gay Male, Shemales  |  Views: 3944  |  
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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 3 years ago  |  Categories: Anal, Hardcore, Shemales  |  Views: 3930  |  
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Down the Path

Down The Path


I hear the knocking on the door. Have my panties on under my shorts and tshirt. Nervously open the door and the man comes by me and I follow him into the living room.

He stops and turns. 'On your knees now'. He moves in front of me showing me his ID so he knows I know who he is in case he gets out of line. 'Tell me why you invited me here.' Looking down embarrassed to have to say it. 'I invited you here to treat me like a faggot Sir. I need a real man to come over occasionally and show me just how much of a fag I am.'

He lifts my chin with his finger then suddenly he s... Continue»
Posted by lookin02 2 years ago  |  Categories: Fetish, Gay Male, Shemales  |  Views: 3936  |  
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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: 3913  |  
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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 5 months ago  |  Categories: First Time, Shemales  |  Views: 3892  |  
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Horse Cock Girl Part 2


Amy woke up around dusk, based on the amount of light coming through her bedroom window. She'd fallen asl**p, her new horse-cock still hard and inside her best friend, Lucy.

Lucy was awake, watching Amy sl**p, and apparently enjoying the cock that was still inside her and hard again. Lucy was bouncing slowly and gently on Amy's cock and smiled when she noticed her friend had awoken.

"Good evening, sl**ping Beauty," Lucy said, in a slightly strained voice. She couldn't keep her pleasure out of her voice.

Amy smiled and pushed Lucy off of her, rolling on top of her and kissing her nec... Continue»
Posted by drew1207 3 months ago  |  Categories: Fetish, Sex Humor, Shemales  |  Views: 3889  |  
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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: 3883  |  
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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: 3884  |  
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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: 3869  |  
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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 1 year ago  |  Categories: Shemales  |  Views: 3858  |  
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My CD / Sissy story and 1st meet humiliation

I recently met up with someone to be a sissy slut for them and wanted to share what happened on my first meet. This is the genuine true story. I use the username indoblu on websites, but my sissy name is Holly so I'll refer to myself from now on as such. I'll mention my history as a sissy before talking about the meet up, skip the first few paragraphs to get to that bit.

I have always known I love girls clothes, lingerie, miniskirts, colourful sheer blouses , anything satin or lace, since a very young age. When I was 18, I finally had a credit card, and bought my own lingerie. I bought clot... Continue»
Posted by indoblu 1 month ago  |  Categories: BDSM, First Time, Shemales  |  Views: 3873  |  
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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: 3854  |  
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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: 3819  |  
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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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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: 3807  |  
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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: 3804  |  
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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: 3805  |  
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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: 3781  |  
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