Shemales Porn Stories
Page 14

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: 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: 3881  |  
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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 2 months ago  |  Categories: Hardcore, Shemales  |  Views: 3865  |  
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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: 3855  |  
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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: 3853  |  
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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: 3847  |  
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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: 3838  |  
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Caught in her undies

I've been home from work for a few days and although I get plenty of sex I love trannies, my wife doesn't know this though. I woke up with the raging horn and decided as soon as she went to work I was gonna treat myself. The minute her car pulled off the drive I was in her knicker draw! Black and pink lacy knickers, matching basque and fish net stockings.....oh and a raging hard on!

Next came the toys. I lubed myself up and popped in the large vibrating butt plug, four cock rings around my balls to stretch them and one around the shaft so I was nice and veiny. Next the porn, shemale of cou... Continue»
Posted by fun_bobby 1 month ago  |  Categories: Anal, Masturbation, Shemales  |  Views: 3830  |  
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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: 3826  |  
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Irresistible



Irresistible



My wedding day... I suppose all brides cry on the day of their wedding. But maybe not for the same reason my bride was crying...

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Becca and I had been engaged for nearly a year. Being that we both came from prominent families we had a huge wedding planned. All of New York society would be in attendance. Her father tried not to show it but he was incredibly perturbed at how much he had to shell out for this huge wedding.

"I don't know where this stupid tradition of the father paying for the wedding ca... Continue»
Posted by klammer 24 days ago  |  Categories: BDSM, Fetish, Shemales  |  Views: 3827  |  
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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: 3808  |  
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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 2 years ago  |  Categories: Fetish, Shemales, Taboo  |  Views: 3803  |  
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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: 3785  |  
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First time with Brooke.

A few years back I lived on the 2nd floor of a four-flat apartment. Downstairs from me lived Brooke. She was an attractive girl, about a year older than me. We were both divorced at the time and she knew I spent most of my nights alone. She would often invite me down for dinner and vise-versa. Other times we would hand out in each other’s apartment watching TV and talking. I liked her but I didn’t feel that she was interested in me. Plus, she had a boyfriend at the time. He was the athletic type that worked in the corporate world. She really didn’t talk about him too much and since he lived do... Continue»
Posted by ahsleymills 3 months ago  |  Categories: Fetish, Shemales  |  Views: 3773  |  
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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: 3773  |  
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My shemale boss part 1

I knocked at my bosses door and on her reply went in. She was standing with her back to me looking out of the window and talking on the phone.

She failed to agknowledge me so I just sat down in one of the leather chairs opposite her desk. I looked at her as she stood by the window and perved over her black stiletto leather knee high boots and tight black leather skirt which covered her ass beautifully.

After about five minutes she turned to me, her black hair to her shoulders and her black shirt partly Unbuttoned showing off her cleavage, it has hard not to get a semi hard on as she move... Continue»
Posted by big_rob49 1 year ago  |  Categories: First Time, Shemales  |  Views: 3771  |  
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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: 3771  |  
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My 1st interracial threesome

I met a guy and he came to my hotel after meeting him on a social network site. He was 6'2 and around 225 pounds military man. We instantly hit it off when he came into my room and gave me a passionate tongue kiss. He then dropped his pants and I sucked his hard 7 1/2 inch cock, he then ate my sweet ass pussy until I couldnt take it any more. Then he topped me and gave me a huge load. About 3 weeks later, he said he wanted some more, I told him that I was super horny and always wanted a 3sum. I was house sitting for a friend and after we emailed each other for about an hour, he agreed to have ... Continue»
Posted by charlie39212 8 months ago  |  Categories: Group Sex, Interracial Sex, Shemales  |  Views: 3762  |  
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The mom who sneaks behind the door.

Hi im james and im 20 years old my mom is in her 50s with a larg rack big booty thin tight abbs and long smooth legs blue eyes and long hair aways weres pantie hoes and skirts and coresets and long red hair.
any way I was on my way home from school at night i got home mom was a sl**p i was on my lap top looking up porn watching this black chick lick a nother chicks ass hole i turnd all the lights off and started rubing my cock.
but as the black chick licked the other chick ass she moand so load some wan els came in will there eyes wure closed she was wearing a skirt and coreset.
she was bla... Continue»
Posted by gothicslave 1 year ago  |  Categories: BDSM, Lesbian Sex, Shemales  |  Views: 3761  |  
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Shemale Stewardess Seduction

Please note that this story is not written by me! It was stored in my computer for a long time now and decided to share it with you. The author's name as well as the site I found the story are not known...


My introduction into the sultry, steamy world of shemales came (and I mean came!) at 35,000 feet, on a plane flight to the Northwest.
I had been working myself to the bone, staying until ten or eleven at night, coming back in at six o'clock in the morning, and I guess the stress was visible. My boss, Terry, a very pretty, sexy lady (who I later found out was a hot-bod t... Continue»
Posted by freegre 3 months ago  |  Categories: Anal, First Time, Shemales  |  Views: 3762  |  
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