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Shemale Delight
I have always considered myself a, women only, kind of guy. After an experience I had 10 years ago, I have added shemales to my list. Anyway, I love to take road trips and visit different cities, usually out of state. I go on-line to do some research about different cities to see what kind of si... Read full Story
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Shemale on Shemale
We were in the back of a taxi, our tongues deep in each other's mouths, tasting and sucking and swirling. My hand slowly moved up her perfectly toned thigh and under her skirt. I lightly caressed her half hard cock through her thong, barely touching her, just tenderly stroking with my fingertips. Sh... Read full Story
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First Time Having Sex With A Shemale
Ok let's begin so I was walking down the street going to the store one day I saw a woman and her daughter moving into a house they had some heavy boxes that they need help with. At first I thought she was white girl but when I got closer to them they we're Asian becuase i only saw the back and they ... Read full Story
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How I got started dressing
I was a sophomore in high school and like any teenage boy I was extremely horny. I masturbated atleast once a day usually 2 or even 3 times because I had so much time on my hands. I started off watching plain straight porn but I watched so much of it daily that I started to get bored of it. I just u... Read full Story
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A girl from the bar!
This guy picks up a chick in the bar and takes her to a private room, the only thing on his mind is to fuck her, but there’s a surprise that the chick has prepared for him! When I stepped down to the hotel’s bar I didn’t even notice that girl at once. I sat my ass down on the so... Read full Story
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My beautiful tranny!
This guy picks up a girl and takes her to his place. Can you imagine his surprise when he finds out that this girl has a dong? Hi! My name is Andrew! I’m a 5.4 feet tall, with some cute beer belly, crew cut light brown haired guy, blue eyes. My friends say I have a big noseJ but it’s ... Read full Story
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His first anal!
Andrew was a very simple guy. He was not aggressive, very quiet and nice. Actually he was not quarrelsome, just a man of peace. But we all know that still waters run deep. Over the past few years, Andrew had longed for being penetrated. Vehemently. He needed to be bent over something and fucked thor... Read full Story
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Italian hoe!
Verona is a nice city. Here, a motherland of Shakespeare’s “Romeo and Juliet”, there are lots of places of interest to see and enjoy. Verona has much more to offer. The city, also known as Urbs Nobilissima, is the second biggest city in Veneto (after Venice). It is one of the citie... Read full Story
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Fucking with Gina!
Hi! Here I am with my own story! I’m a young white guy, a good looking son of a bitch! When I was a college student, one of those numerous young people who always rush for something, then I was a focus of interest for lots of chicks around! But then something changed. Changed a lot. As I remem... Read full Story
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A new girl around!
You know, things, I’m gonna tell you about started when I was a teen. I was like every teen guy, I loved web porn, looked at porn on the internet, surfing porn sites through the web space and masturbated a lot. I loved and now love to watch lesbian porn: it was so hot watching girls having sex... Read full Story
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My first ass fuck! From Anita
Hi! My name is Anita, I live my life always wearing lace and satin. I have always loved the way those materials feel against my soft skin. I have long red hair and bright green eyes. My friends used to call me Charles but about 12 years ago I had this epiphany of feeling that being a woman was just ... Read full Story
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Trance club
It was the worst day in my life. My girlfriend Ally and I had been quarreling and rowing for several weeks, we were on the verge of breaking up. I just wanted her to be happy. I lived my life for her. I guess I stood no chance to make her smile at me again. We broke up. Ally said everything was chan... Read full Story
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First work day!
Having just graduated from college in Miami I took up fashion as a career! Impressed? In fact, I managed to land a job as a clerk in ready-made clothes shop. Sounds not as impressive as I’d like to have but that is just a beginning. You think there are no other interesting places in the whole ... Read full Story
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In the bus
Everything can happen in a bus, you are going to read something that happened in real life and it’s for you to choose whether you believe it or not. I was looking forward to meeting her in the bus. I’d changed my working schedule since the first time I saw her. I did everything just t... Read full Story
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Lift!
Have you ever been stuck in a lift with a pretty chick who later turns out to be a shemale? Well, it’s going to be a nice time, I assure you! Today was fucking damn day! It’s been one of ugliest days in my life. My company sent me, as a representative to take part in some high level f... Read full Story
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Two hot CD lesbian sluts share an intimate moment
Her name was Kelly, we had met online in one of the gay chat rooms I like to frequent and for the next couple of weeks we had developed a friendship, exchanged pics and fantasies and I was really, really into her. we had a lot in common, more than just the mere fact that we were both gay CD’s ... Read full Story
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Miko and Mali; Thailand's finest teen sisters
Last August my friends and I went on a “lads holiday” to the beautiful country of Thailand. We had booked a fortnight, which was to consist of five nights in a city hotel in Bangkok, and the remainder in a stunning 5* resort in Phuket. It was my first time in the country, my friends hav... Read full Story
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T*GIRL AT THE BUS STOP
The radio was loud and the top was down when I first saw her. She looked so beautiful sitting there at the bus stop.I remember her legs, they were long and tan and clad in silky smooth thigh highs. Her skirt shifted when she crossed her legs and I could see the garters clinging to her tan skin. S... Read full Story
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Tranny Gas Station Attendant
This happened about ten years ago and I thought I'd share it with you all for your enjoyment and mine! Like I've said before, although I'm bi-sexual, I don't walk around checking out other guys, nor do I like to be intimate with one. Sure, some might consider taking a cock in the mouth or ass intima... Read full Story
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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 ... Read full Story
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Caught!
Let me start out by saying that I was very much in the closet about my dressing and the fun I have when I'm dressed when this happened. But more and more I kept fantasizing about one of my male friends. He's very good looking and keeps in shape by jogging every day. Several of the times we've gone o... Read full Story
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My lesbian shemale adventure
My name's Kimmi and I used to be a stripper. I'm a genetic girl, and I always had a wild streak. Guys liked me 'cause of my long blond hair, slender build, and sense of humor. They also liked my 36C breasts :) I danced at a place on Sunset Blvd in Hollywood (this is a true story, so I won't use the ... Read full Story
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First time tale
I am confused sexually. I'm straight but curious I know I want to be with a real woman I always go out with a real girl and sometimes I get a date but most of the time I get played out. For about a year I have had this fetish for transsexuals I don't know why but I started looking at pics online ... Read full Story
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A Halloween Hoodie story
This is the story of my first time going out dressed; it was halloween last year (2009). I figured i'd have less to worry about walking around dressed in a gothic tartan corset, spider-web mini-skirt, fencenet tights and about 10 armbands and bangles. It wasn't exactly brilliant but it was the excit... Read full Story
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The switch
HI have been married for 12 years now. Trim and dapper, this 35-year-old's marriage was satisfactory enough and I played the role of husband well. Sex with the wife was still good, with both making out at least once a week or on rare occasions, once monthly. Twelve years on in this heterosexual rela... Read full Story
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A Trip to the Beach
I had known Stacy for about three years, but I had never known about her little secret. That day when it was revealed changed everything for me, and for Stacy too. We were the greatest of friends, spending almost all our time together. We had come as close to each other as lovers but as two women, n... Read full Story
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Job Description
My life changed recently and I’m still trying to figure out if it’s for the better. My name is Don and I’m 18 years old and fresh out of high school. My grades weren’t good enough to get me a scholarship and my parents make too much money to qualify for government money. So a... Read full Story
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The Picnic
Going for a picnic was not my idea of fun. I was not a miserable person and liked being outdoors but the idea of eating on the ground where there would be ants and flies and thing like that did not fill me with joy. However, my boyfriend had promised me that it would be fun and so I took his word fo... Read full Story
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My lesbian shemale adventure
My name's Kimmi and I used to be a stripper. I'm a genetic girl, and I always had a wild streak. Guys liked me 'cause of my long blond hair, slender build, and sense of humor. They also liked my 36C breasts :) I danced at a place on Sunset Blvd in Hollywood (this is a true story, so I won't use t... Read full Story
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My amazing Filipina girl
Today's post is not a usual ladyboy sex story that we all got used to, but something more romantic, down-to-earth and non-porn. Thanks British Buy for sharing this story and being so brave in making your fantasies real and finding your true love. I wasn't looking when I found her. I wasn't reall... Read full Story
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Soo, my ladyboy friend in Bangkok
This shemale story is not your usual one as it's written by a lesbian girl Jamie and it involves a very sensual description of sex with an Asian ladyboy. Enjoy reading! Well as an openly gay Lesbian woman (submissive as I say) a long way indeed. My friend in Bangkok, Soo is a beautiful, articula... Read full Story
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My second time with ladyboy Nan
If you like the idea of a girl going at it with a ladyboy and follow the ladyboy stories section of our blog for some time, you should remember the story about Thai ladyboy Nan that our reader Julia wrote. Well, this is her second report and I hope you enjoy it as much as the first one. This time... Read full Story
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Sleazy shemale fantasies
Sifting through the comments that readers leave at Trans Ladyboy, i have found two really hot shemale fantasies that I would like to devote separate space to. They are both written by two horny guys, wyocock and Eddie, who dream about being with shemales all days long (the only difference is that E... Read full Story
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Thank you for Paradise
This hot shemale story was sent to me by our forum member Leeya and i'm anxious to share it here with everybody. It's a classy story about a guy who went to an Asian country on a business trip and met a very beautiful womain in a very romantic atmosphere... Little did he know that this young voluptu... Read full Story
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Foursome with two ladyboys
It's been quite some time since I posted a new shemale story here. Hope all of You who have experience with shemales will finally have some courage to write about it and share it with us. Let this sizzling story by Tommy be an inspiration to You. Who wouldn't want to be in his place in this crazy fo... Read full Story
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Shemale girlfriend
This true life story was posted at our forum by a new member bigbell609. Although it is a pity that he couldn't be with Kristin anymore, his first experience with his TS GF was very remarkable and romantic. Who of us wouldn't love to be in his place... I've been married for a few years now. My wi... Read full Story
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Lakeside Awakening
If anyone had told the way I’d meet my soul mate a few years ago, I never would have believed it. It was my senior year of high school and I had recently gotten out of yet another bad relationship with a girl. Lina had been a pretty, chubby blonde with a nice personality but a nasty temper. We... Read full Story
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The House
I knew that the only reason I was going in to the Big Brother house was because I was a shemale. I did not really mind that was the reason as it meant that I could still appear in my favourite TV show. I did not want to become a star, like many of the contestants did but it would be nice, just to se... Read full Story
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My first time with a shemale escort
This story that was posted at the forum today by our new member got me hard as hell. He writes about his first experience with a tgirl and i can't be more positive that most of us would like to experience this too. Enjoy reading... I recently had my first experience with a shemale. Here's how it ... Read full Story
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3 tgirl story
Kristin made sure everything was ready. Her parents were out of town, and said she could have 2 friends over. She decided on her best friends Taylor and Siera. She also planned on showing them that she was, in fact, a shemale. The 2 arrived around 630 to 7. Her cock grew hard when she looked at them... Read full Story
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A slave for three beautiful shemales
Here's another great story that was submitted by one of our readers. Enjoy reading. I used to be a bouncer at a night club and one day after my shift a very foxy black busty babe approached me just outside the club. She was wearing hot pink track pants and itty bitty tube top that was some how ho... Read full Story
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Party with my best friend
To continue the topic of shemales fucking girls, I am publishing this awesome story of a young girl getting fucked by her high school friend! Enjoy reading! My name is Cindy, and I am 18 years old. I have blonde hair and brown eyes, and boys think I am very sexy and attractive. But the story I am... Read full Story
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Tranny Lisa's first sexual experience
My name is Lisa, I am a 25 year old well hung little lady. Looking at me you would never believe with my perfect girlie body what I have in store for you. The things that I can do and teach you would blow the mind of the most advanced sex addict. Run your hand down feeling my feminine curves, a litt... Read full Story
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The Anniversary
After ten years of marriage, Anne and Edward were still very much in love. They had no children and still had a very active sex life. They tried to keep things interesting by trying new positions, techniques and playing games. They often role played and wore costumes which was a lot of fun. Howev... Read full Story
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Lesbian adventure with a shemale
My name's Kimmi and I used to be a stripper. Guys liked me because of my long blond hair, slender build, and sense of humor. They also liked my 36C breasts :) I danced at a place on Sunset Blvd in Hollywood. The stage was gorgeous, had a generous runway, and beautiful lights. I loved dancing there, ... Read full Story
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My three times with shemales
Hello, I first became attracted to Shemales while watching a girl on girl porn movie. A surprise was there was a sexy girl that dropped her panties and out came a huge cock. I was stunned but really arroused. I then became curious and surfed the net for Shemales. I kept thinking something was wro... Read full Story
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Suffered for years
I am one of those guys that have suffered for years, 29 now, I have fantasized about shemales since I was about 15, wouldnt dare come out in school, got a blue collar "macho" job, met a woman at 21 fell in love, (i am very straight yet extremely bi-curious) got married, have a step son, lo... Read full Story
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Giving shemale a blowjob for the first time
I've been fantasizing about a shemale cock for a long time. Get me right, I am a straight man and all, but somehow the idea of sucking a girl's dick always turned me on. I'm not a big fan of anal sex and I don't think I'd love someone's cock in my ass, I'd rather prefer to give shemale a blowjob. ... Read full Story
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Winter Heat
I saw him in the breezeway, the open hall between the apartment buildings. My not-so-new neighbor. Been keeping an eye on him for a couple of months. He has a girlfriend, but nothing committed, and we flirt casually. He’s cute – six-three, so he’s tall, but it’s not string-be... Read full Story
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The Peep Show
Alice had been to Amsterdam a few times before and had always had a great time there. As a shemale she often felt uncomfortable in certain places, talking about what she was, but here, everything was much more relaxed and she felt able to be honest with people and she found that she was more accepte... Read full Story
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The Hot Girl at the Bar
My girlfriend and I broke up the week before, so I was pretty depressed. The guys at work decided to take me out to the bar after work to get wasted cause that’s what we do. So we all packed into the truck and headed to the bar. When we got there we were the first ones in that night so we sa... Read full Story
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Shemale Love Story - part 1
Let me tell you a story of a shemale and her lover. Some background is required here. My girlfriend (we'll call her Lisa) was at the time about 27 years old and had been single for sometime after a bad experience with a man. She is a stunning girl, and most people would not know she was transsexual ... Read full Story
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Ladyboy Surprise - Part 1
It has been many years now, but I can't seem to forget what happened to me. I was as a young seaman in the Navy. I still wake up at night rock hard thinking about it! I am happily married now to a good woman and have a few kids, but I can't get this image out of my mind. We had been out to sea fo... Read full Story
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The Breast Fantasy Come True
As a gay man, Paul had always only been interested in having relationships with men but he loved breasts. There was something about them that he really liked and having a few friends that were female made him even more curious and he asked them questions about them and one of them even let him have ... Read full Story
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My Preference for Girls didn't change
When I decide to finally go into my transition, I kinda felt I might think differently about boys. Well I guess I do some. I like gay boys or more feminine boys now than before I started trans, but I find I still like girls. Most trans girls I know now prefer to have sex with boys. Maybe I'm confuse... Read full Story
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Sexy Masturbation In Free Shemale Chat Rooms
Having had a long day at work and driving home enjoying the wonderful early fall sunset, I was starting to be kind of romantic… Maybe not that romantic, but I felt like having a nice girl next to me to cuddle and scoop with. The more I was thinking about cuddling and scooping, the needier I w... Read full Story
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