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First time doing that!!
So I love to dress like a girl and have done since I was about 15, but being married and all it’s a bit hard to do it very often,. I’m a local tradesman so am out all day in my van and have a good knowledge of the area I live in, or so I thought. About 2 miles from my house is a crushing site tha... Read full Story
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First time
For as long as I can remember, I've preferred my chicks with dicks. There's something about a sexy babe with perfect makeup and hair and a cock that just turns me on. Maybe that makes me a pervert - I don't care! I remember I was just out of high school, 18, the first time I made it with a tranny... Read full Story
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My First Time Made Me A Slut
A true story of my first time. And why I so need a daddy now. The first time I went out dressed. I went to a bookstore in east Portland. As I got out of my car feeling the breeze up under my very short silky skirt, trying to pull it down as cars were wizzing by. I walked or should I say wobbled the... Read full Story
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The Girl Next Door Ch. 03 by derezzed ©
Chapter 3 – The Night Out Michael woke up on Monday morning feeling quite relaxed. The sun filtered in through the blinds towards him. He felt warm from the gentle rays. As Michael became more alert, he examined his surroundings. The feeling of silk sheets wrapped around him and Alexis's arm casu... Read full Story
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Crossdresser gets dick for first time
I was so tired of just watching porn. So tired of the sissy hypno threads that made me crave men, crave cock, crave being weak, crave being the bitch...only to cum and do nothing about it. But the desire to transition from fantasy to reality was growing stronger and stronger. I decided it was ti... Read full Story
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First Time Outdoor Festival Fantasy
Fantasy Setting: Summer time in the mountains of Colorado the perfect bluebird weekend we all dream of. The day before an underground rave in the mountains all my friends bail on the show and was now left with either not going or going solo. Well I deiced what the hell and I'll go solo an... Read full Story
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Shemale First Time
First time Sex with a shemale. Intro. I have read several stories of first time sex with Transexuals and none relate to my experience. So for those who are truly curious about how to go about it and what it is like this is my tale. I have always been a straight guy as far as I know. Married... Read full Story
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My first time with a guy
MY FIRST TIME WITH A GUY Another true story it’s kind of long but I think you will enjoy it I lived west of Lake Worth Florida. At that time we were surrounded by 1500 Acres of woods. There were 10 of us and we all had dirt bikes and would go out riding all the time.. On Saturdays we had a game ... Read full Story
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My First Time Out Part 1
Shayna paced back and forth throughout the entire Suite while she nervously smoked the long thin cigarette. She occasionally stopped and peered into the mirror thinking that all of her hard work had gone to waste for tonight. She was dressed to kill and had no place to go. The red patent platforms w... Read full Story
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My First Filling
It was my 18th birthday and my friends were getting on my back about still being a virgin. They’d pick on me about having not had sex with a gir yet, but they didn’t know that I fantasied about something other than a girl, I lusted and craved myself a trans partner. All the fun of a girl but with a ... Read full Story
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My First Time Out: The Preparation
Shane, a 24 year old blue-eyed, blonde-haired salesman boarded the airplane enroute to beautiful downtown Salt Lake City, Utah. He had made the trip many times. He always conducted his business in a timely fashion so he could get back to his office making sure not to miss any other business opportun... Read full Story
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MY first time with a Tranny
So one night i was feeling super horny, and was jacking off all day, i went our that night and got home super d***k and super horny. i called up my local chatline and started talking to this tranny that told me she was horny as well, one thing led to another and i gave her my address. we talked on t... Read full Story
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My Knight
I felt good as a looked around the club and watch the Queens on stage perform their acts. I felt like I belonged here among this faction of society. Drag queens and Trannies were my people and the only thing I regret is being in the closet and not having the courage to do it more openly. However i d... Read full Story
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First Time with she-male
For as long as I can remember, I've preferred my chicks with dicks. There's something about a sexy babe with perfect makeup and hair and a cock that just turns me on. Maybe that makes me a pervert - I don't care! I remember I was just out of high school, 18, the first time I made it with a tranny. S... Read full Story
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First Time with she-male
For as long as I can remember, I've preferred my chicks with dicks. There's something about a sexy babe with perfect makeup and hair and a cock that just turns me on. Maybe that makes me a pervert - I don't care! I remember I was just out of high school, 18, the first time I made it with a tranny. S... Read full Story
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First Time Sissy Maid
I had been fantasizing for many years about serving a dominant Mistress, watching lots of movies online, and generally lusting over the doms I saw posting ads. At the age of 28 I finally found the courage to answer a rather intriguing post by an older woman and her trans partner who were looking for... Read full Story
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Castro - shemale goddes
Nobody would have believed the scene was true, her slender, smooth and tanned legs crossed in such a deliberately provocative way as to reveal a glimpse of crisp white panties. Her tightly fitting, classically styled little black dress cut to ensure firm large breasts were displayed to maximum effec... Read full Story
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Reshooting the Scene, Chapter 1
I have been a porn aficionado since I was a teenager. My first dabblings were with Hustler magazine and a *very* hardcore mini-novel called “Her Busted Asshole,” which told the raunchy story of Ginny Cummings’ sexual coming of age. In addition to the very graphic story, it had full color glossy p... Read full Story
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First time
For as long as I can remember, I've preferred my chicks with dicks. There's something about a sexy babe with perfect makeup and hair and a cock that just turns me on. Maybe that makes me a pervert - I don't care! I remember I was just out of high school, 18, the first time I made it with a tran... Read full Story
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A First Time for Hannah
At age 24 and after years of dressing in private, I finally decided I needed to get out. I had been scouring online personals for some time but never got further than exchanging a few emails and trading pics. I had been in touch with other CDs from all over the country and had even considered travel... Read full Story
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Best session with a T Girl
I like T-Girls. Recently had a chance to go to Costa Rica for work. While I was there I decided to see what Costa Rica had to offer in this department. There is quite a good amount of girls to select from. I started texting this Tgirl and we set a time. I got ready and headed over. It was a Hotel th... 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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Ginger's First Gangbang
I had been enjoying regular meetings with my older lover, Mr Webster, for some time and the routine typically consisted of meeting up and heading off in his car for sex at some secluded spot in the countryside. He liked me to dress as femininely as possible, in pretty dresses, skirts and heels and a... Read full Story
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First Time With a Shemale
I was living in LA and pretty fresh out of school, not to mention pretty naive in the peripherals of human sexuality. I'd been with a few girls growing up, but nothing ridiculous. I liked going out with my buddies, and we'd drink and there was the occasional recreational use of ummm, how should we... Read full Story
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Slut /W Bad Boy
I was excited as always because I was about to go out in public and hopefully I will meet some horny man with some money and get laid. Now, to make sure that I am a picture of femininity, I double checked my makeup in several mirrors from many angles. My lips were perfect and I made sure my cheeks b... Read full Story
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Girl from Uncle
Tonight, I have to tell it all. It’s no secret that my uncle and I had a very special bond he had been eyeing me with those adventurous eyes from the time that I was 14 years old. And frankly I enjoy his ogling. I could feel my nipples get so hard when he looked through me with those alert and spark... Read full Story
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My First Time
This is my first ever story written about my first ever sexual encounter with a transgender woman. I really hope you enjoy and want to leave me some feedback… I have slept with many women in my life. I have been married, had more girlfriends than I can remember, several fuck buddies and far too m... Read full Story
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Shemale Ride Along (Part 3)
It was the last day of classes. All of the finals were finished, and everyone was celebrating. My finals had been particularly rough. It was the last semester of my freshman year and I didn't study as much as I should have. The problem was that I lived next door to a girl that I had been having... Read full Story
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HOW ONE PEEPING TOM MORNING TURNED ME INTO A SHEMALE SISSY BITCH
It was while cutting across his back trailer park lawn around 7pm on misty July Saturday evening, when I first discovered that Mr. Parker was really a fag. How else could you describe a man wearing a long blonde wig on his head while below he wore only a large somehow stuffed pink lacey woman's bra ... Read full Story
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My wonderful life with Pat : Pat birthday
Today we will received a friend of Pat for her birthday Charles and Pat are friends since the kindergarden Today Charles is married with Suzanne. Charles has followed the Pat sexual changes from young man to lady shemale. Before being with Suzanne Michel had participated to several parties... Read full Story
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Steve
So on AFF, I used to be gold but guys will just hit you up, sooo I got hit up by an 8in boy. Wasn't sure I'd want to prep up an 8 so I didn't get all ripped up, but nice profile and a fucks a fuck sometimes. What to wear to get cum in tonight? Still pretty warm, I'll go mini with tighter leotard (mo... Read full Story
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Catching up with the biggest cock
I have recently written with an account from my diary about the biggest cock that I’ve ever seen and someone saw the experience and wanted to know more as I had said that I met him a few times. So, I can bring that right up to date now because I have recently been to see him again. But let me go bac... Read full Story
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Shemale Ride Along Part 2
Note: This is a sequel to my previous story, "Riding in Cars with Shemales." If you would like some back story into how Terra and Matt met, please read it. If not, you can probably still enjoy this one by itself. * It was a wonderful day in May. The sun was shining. The sky was clea... Read full Story
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Be My Bitch
After a long day at work, I get in my car, and look forward to the long drive home. It gives me time to unwind and relax. I try to forget about the hectic office and concentrate on my beautiful girlfriend waiting at home with that warm smile that she greets me with when I get there. However, tod... Read full Story
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Gangbanged By 3 trannys
Gangbanged By 3 trannys This is a story about the night I was Gangbanged by 3 trannys. I was at a Transgender after hours clubs that was filled with hot ass Tgirls. This tall white gorgeous woman was eyeing me the moment I walked in. She was wearing this fitting blue dress that showed off ... Read full Story
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Two CD's the first time we meet.....
We are meeting for the first time since talking online. I want to dress for you gurl, I want to feel as you do, I want to be your slut, your slave of desire. My panties are a sheer white, my hard cock can be seen ever so pressing against them, I rub myself for you as you watch, drooling now. Hand... Read full Story
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First Sexual Crossdress Experience
How my secretary found out I'm a bi TV and how me and my TV friend educate her into some of the more zany aspects of TV sex. *** As I laid back against the wall of the toilet with my nylon-clad thighs spread wide and my erect cock jutting up lewdly from between them, the wooden door in front o... 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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First time
I was the only boy in my family. Tall, slender, and somewhat effeminate. Many said I looked like my mother, who I adored. As a youngster, I longed to dress like my sisters, who wore such pretty things. One day, when I was alone, I snuck into my sister's room and admired all of her pretty things. On ... Read full Story
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Double Take
Sandy Lane glanced at his Rip Curl watch as he paddled back towards the lineup. Less then twenty seconds remaining in his heat. Sandy had one good wave under his belt, but unless he nailed another one, there was no way he was going to make it into the finals. He glanced over his right shoulder, a... Read full Story
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Sissy Slut and Stepdads
Frank was pumping me hard and his huge cock seemed to have grown and become extra hard. I am so thrilled that way he enjoys fucking my ass with such passion. I would almost think he was in love with me if this relationship wasn't so bizarrey. It’s ironic that as a male I always get total humiliation... Read full Story
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First time with big surprise
My first story translated into English, I hope you like it. It was late at night, I had been drinking with friends and was on my way home. I am a man in his early 30s, smartly dressed and looking quite attractive. The night was beautiful, clear sky, warm and in the city were some people on the ... Read full Story
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Captain John’s Playmate
Alessia Travestita’s Adventures – Episode 1 – Captain John’s Playmate. It was forecast to be a gloriously warm and sunny day, clear blue skies with a gentle warm breeze from the South. So I decided to leave the town behind and head out into the countryside for the day, get some fresh air, toning ex... 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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First sexual experience with shemale
For a long time me and my girlfriend had fantasized about a threesome with a shemale. We even brought in her didlo for fun one time and i found myself very excited by it. After that, thats all i thought and fantasized about. Soon it was to a point that I wanted to experience a sheamale alone. My ... Read full Story
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First time dressing up
I was always interested in women's clothing. I don't know what it was but it just made me wonder what it was like to be a girl. When i was 15 i finally gave into my curiosity and wanted to browse my s****rs clothes. I went into my s****rs room when the house was empty and opened up her closet. I saw... Read full Story
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Honeymoon Suite 2
Jason is on the phone with room service, while I am about to change out of my wedding gown. I had just got married, and I was now the blushing bride. Yes I got married. I was nervous now and my pussy was burning, because of the crazy bet we had made about not having sex a week before the wedding. We... Read full Story
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Big Dick Alessia Visits Dallas
Alessia Hung Mature MILF travels to visit a Big Dicked Man and his Sexy Household If you like Transexuals, big cocks, bondage, BBWs, big clits, deep throat, fisting, 69, ass fucking, sounding, piercing, cum swallowing and big loads this story is for you. If not don't bother reading. If you fav... Read full Story
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A Series of Perverse Dreams, Part 3
After my last couple dreams, I began to watch a ton of gangbang and bukkake porn. I had jerked to this kinda stuff before but now I was watching it constantly and this time around, it was to the thought of being the girl in the scene. Something about watching a beautiful woman taking numerous cocks ... Read full Story
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My First Time Out Part 3
Angelo was still working on Shayna's blonde wig. He fussed with it, combed it, and teased it. Angelo knew a romantic style was very important to Sir Dominique. Shayna was escorted to a tremendous makeup table. Saki placed a headband on her that stretched her scalp and raised her non-existent eyeb... Read full Story
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My Awkward Phase
My Awkward Phase ©Alexandra Rios 2019 The greatest lie is that what happens in high school doesn't matter, because life begins in college. I pretended to agree, although I never believed it, for I was the world's greatest liar. Wannabees I was hanging out with my friends Quinn, Barb and Anne ... Read full Story
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Sissie Slut's Windows of Womanhood
I flash back to my first time with a grownup adult at the tender age of16 . I was so nervous now that we were here in the motel room. I was nervous for so many reasons. I lied to my family and told them I was staying at a friend’s house. Instead, I'm here with Mr. Joey in a motel room and he was my... Read full Story
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Alessia Travestita Hung Mature Blonde British Porn Star
Alessia Travestita Hung Mature Blonde British Porn Star If you like Transexuals, big cocks, bondage, domination, deep throat, fisting, spit roast, 69, ass fucking, cum swallowing and big loads this story is for you. If not don’t bother reading. If you like my story please leave comments and ... Read full Story
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First Time With Shemale
For as long as I can remember, I've preferred my chicks with dicks. There's something about a sexy babe with perfect makeup and hair and a cock that just turns me on. Maybe that makes me a pervert - I don't care! I remember I was just out of high school, 18, the first time I made it with a tranny. S... Read full Story
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TG - shemale at the airport
Layovers are a pain at the best of times but the prospect of five hours at the airport was not a good one. My inbound flight had been delayed and I had missed my connection, so there was nothing for it but to wait out the afternoon and catch the next 'plane home to the wife and kids. The only ... Read full Story
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My first time
I was nervous, and had never even gotten laid before. I had jacked off a lot, but I thought about real women when I shot my load. But Dani sure looked and seemed like a real woman, and she had brought me back to her place. When she started kissing me, I didn't even have to think about it - I slipped... Read full Story
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