Shemales Porn Stories
Page 13

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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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: 3932  |  
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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 4 months ago  |  Categories: First Time, Masturbation, Shemales  |  Views: 3926  |  
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The perfect first time

It took me some time to realize and accept I was gay. For a long period of time I was masturbating fantasizing that I was a girl, but on most cases I was making love with another girl; that to my mind was a proof that I was not gay. Several times I was wearing my s****r’s underwear and clothes but I never pictured me with another man; not to mention that I had never fingered my ass.
It was summertime and I was 15; at that time we were living in Cyprus (my father was a diplomat and we moved in several countries around Europe). As my father was stationed in the capital city (Nicosia which is lo... Continue»
Posted by georgette32hk 14 days ago  |  Categories: Anal, Gay Male, Shemales  |  Views: 3921  |  
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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 3 months ago  |  Categories: Anal, First Time, Shemales  |  Views: 3921  |  
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Shemale Summer

Once again, this is not a story written by me! It was stored in my computer for ages and decided to share it with you. Hope you like it!


One hot summer day, my friend Sam and I were scoping out the babes at our local beach, as usual. I saw this really hot, busty blonde a few towels down giving me the eye.
"Hey, check her out!" I said to Sam. He peeked up from beneath his Ray Bans and shook his head.
"Forget that one," he said. "She's not your type."
"What do you mean?" I said. This girl would be anybody's type—even blind men!
"Just take my word... Continue»
Posted by freegre 2 months ago  |  Categories: Anal, First Time, Shemales  |  Views: 3912  |  
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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 6 months ago  |  Categories: First Time, Shemales  |  Views: 3893  |  
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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: 3881  |  
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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: 3871  |  
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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: 3866  |  
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Surprise

It had been quite some time since I had tasted the flesh of a young buxom female. I needed to have a good-looking lady at my side and soon. I decided to go dancing in town at one of the local bars. I don't usually hang out at these kind of places; however, It may be time I started. It sure is hard to find a date now a days. I went to the Lighthouse Bar. It usually is happening all night until about 4:00 am.
I dressed in my tightest jeans and my best button up shirt. I looked for a lack of better words--tuff. All I had to do was get some chick on the rebound or something, buy her a fe... Continue»
Posted by freegre 1 month ago  |  Categories: Hardcore, Shemales  |  Views: 3864  |  
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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: 3841  |  
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Sissy Cum Slut Stephy

I have been cross dressing and playing with men for many years now. One of My first experiences being gangbanged by an unknown amount of guys was at a book store. I was about 18 at the time and it kind of traumatized me as it was pretty much a gang fucked. I was dressed up in a white sundress with lace top stockings and white strap on high heeled sandals all borrowed from my older s****r. I had my make up done up just right and looked great. I have long blonde hair and was dressed to kinda sexy and all keyed up being out dressed in public so I decided to go find a guy for some Sexual explorati... Continue»
Posted by SissyCumSlutWhore 1 month ago  |  Categories: Anal, Group Sex, Shemales  |  Views: 3847  |  
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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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Getting Fucked By My Shemale Gym Teacher

My name is Heather and I am seven teen years old. Like most people in my school I actually liked coming everyday because it gave me something to do and I got to hang out with my friends. My least favorite part of the day was gym class because I found it pointless. It wasn't like I couldn't do what we were asked because I am in decent shape I just hated being all sweaty for the rest of the day. I have blonde hair, blue eyes and am thin with decent boobs and ass I guess lol. Our gym teacher Ms.Hanson could be a bitch sometimes but all in all was pretty cool. She always hung out and joked with us... Continue»
Posted by xXSecondCitySaintXx 1 month ago  |  Categories: First Time, Hardcore, Shemales  |  Views: 3817  |  
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He caught me in his wife's cloths

I do odd job's and I was about to do one for my wife's best friend Tina and her Husband Phillip. I went over and looked at the job. I told her it would take several days and that I could do the work while her and her husband were at work. That way I wouldn't be in anyones way. Well the first day of the job I showed up just before Tina left for work. Pillip was already gone. We chatted a while the she left for work. Tina is really very hot and I have wanted to fuck her for a long time. Sense i knew that was not going to happen I thought I would do the next best thing. I went stra... Continue»
Posted by firstknightd 4 years ago  |  Categories: Shemales  |  Views: 3818  |  
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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 4 years ago  |  Categories: Anal, Shemales, Taboo  |  Views: 3813  |  
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Schoolgirl Sissy Crossdresser and Her Black Daddy

WARNING: This fictional story contains graphic sexual/profane terms and scenes. This is a work of fiction, a fantasy, and is meant to be enjoyed by horny fucking perverts like myself.


I can't believe this is happening right now. Here I am, a 16 year old white boy dressed in the sluttiest schoolgirl costume and makeup I have ever seen, being barebacked by an older, married black man. How'd I get so lucky?! Let me start at the beginning...

It was summer time. As always I spent my summers hanging out and occasionally mowing neighbors lawns for some extra cash. Although I wasn't exactly th... Continue»
Posted by AllisonCumms 1 year ago  |  Categories: Anal, Interracial Sex, Shemales  |  Views: 3814  |  
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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: 3810  |  
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