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How I learned the pleasures of anal
This narrative is the journey that lead up to my first experience with anal sex. The details I have here are as accurate as I can recall and any dialog is essentially the best of what I can remember now. It of course gets more sexually explicit and graphic towards the end... I was born and grew u... Read full Story
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First Time Being a Woman
My heels clicked on the concrete path as I made my way toward the secluded toilet block in the southern parklands. Tonight would be my first experience being with a man whilst I would be dressed as a woman. I had been dressing now for some time and had fantasised about what it would be like. I didn'... Read full Story
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First cock in skirt
Another little hot story from our forum. A guy who goes by nick Stephen54 writes about his very first experience with a hot CD, getting and giving his first blowjob and having anal sex for the first time. Hello. Was wondering what peoples first time experience was? Mine was back in the 70's, d... Read full Story
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First Encounter (Mexican Travesti)
I grew up near the U.S.-Mexico border and am ½ Mexican Hispanic and ½ Anglo (white). I visited Nogales Senora on the Mexican side on and off during my teen years. As a young adult, I was fearless and sometimes went across alone to visit the strip clubs, get a cheap lunch, or look for Mexican sweetie... Read full Story
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The first shemale experience: Balls deep in ass
A guy from our forum that goes by nick BallsDeepInAss shares his first experience with a tgirl. Good for him for finally putting his cock balls deep in shemale ass! I recently had my first shemale experience. I met her on an online dating service, she was waiting for me at the door in a seethru d... 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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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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My very first experience with my classmate
He was amused by the sight...of me in lingerie..standing on the porch,it was obvious he was in a shock (or state of extacy?) and couldn't take his sparkling blue eyes off my firm body inside the dress...he closed the door behind,like he was worrying if someone could see us ..I don't know why but i f... Read full Story
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A true first time.
I want to preface this reiterating that this is a real story about my first ever experience with a shemale. It's a memory I will hold forever as it was everything I could have hoped for and, as I may share in the future, lead to other experiences, too. A little history of before the first meet ac... Read full Story
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First Time Fantasy
I'd never had a real experience before. Years of wearing panties and fantasizing, but nothing legitimate. I imagine it's the same story as many other panty lovers: started when I was about 13 by stealing some of my mom's things. Bras at first, then panties. Soon I began looking forward to being home... Read full Story
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MY FIRST SEX WITH SHEMALE
This is some of True incidents happen in my life when i take an office trip at last 2 years. After a long flight, I departed, and made arrangements for my luggage to be sent to the hotel, and then went to a restaurant / bar to get a meal and a drink. I am not a good flyer, and get real nervous durin... Read full Story
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A Lady's First Time
When he'd first stepped into the bathroom, it had been Daniel who had stared back at him in the mirror. Now, the face that smiled back was almost complete, and Cassie was nearly ready to go. First had come all the undergarments -- the satin panties that felt oh so right, then the bra that had giv... Read full Story
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First Gay Experience
Me and a buddy decided to go see a rock concert at the Great Western Forum (that's what the Staples Center was called back then). I was 21 at the time, horny all the time and could never get enough pussy. So we go to the concert in our own cars since his brother lived nearby and he was going ther... Read full Story
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Amanda and Me Chapter 2
I rolled over after reading Amanda's note with a big smile on my face. I couldn't believe that after all the time I had spent masterbating to shemales and fantasizing about meeting one it had actually happened. Not only had it happened but it had been the most amazing sexual experience of my life. ... Read full Story
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Nicks Shemale Experience
Nick had discovered he had a thing for shemales 4 months ago after stumbling across some pictures on the Internet of a really hot ladyboy from a porn link site. This sort of thing had never turned nick on before but looking at pictures of the small-breasted brunette really made his dick hard. It did... Read full Story
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Lana: First Encounter
Well, I occasionally surf Craigslist in the Casual Encounters section clicking on the t4m button. More often than not I see the regular posts. No one over 35, big cock, muscular a +, face pic a must, no cock pic, 420 friendly, you must host, etc, etc. I wonder, ‘what are these people thinking?... Read full Story
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Danielle's First Time
Danielle was born in the winter to 1976, but she was born a male by the name of Daniel. Daniel looked like a normal male child aside from liking girly things. Whenever Daniel would play dress-up he'd always dress in his mother's or his aunt's clothes and his parents thought that was cute until Danie... Read full Story
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My first TG lover
I first met Holli at the gymnasium of our apartment complex. Since it was around 6:00 am on a Sunday morning, I didn’t expect to see anyone that early. At first just like we all do, the customary good morning, small talk, and it usually stops there, but there was just something that drew my attentio... Read full Story
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A Shemale Vacation Part 3
At the French border, it was discovered that we had no passports. We were taken from the train and into a room for questioning. All four of us, Josh, Olly, Harry and myself, were terrified. Sure, we'd been in a sticky situation before on this trip, sticky particularly for me rather than the others, ... Read full Story
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Anal Queen
Amanda fell to her knees in the darkened theater and slowly unzipped my pants. My cock throbbed. As she pulled down my underwear, I felt my manhood spring forth. Amanda took the whole sausage into her warm, soft mouth. I could barely see her face in the darkness, but I could feel her between my l... Read full Story
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My 1st Time was Not the Only Time.
One late night after hitting the slopes and partying I left my friends birthday party feeling extra horny. It was about 6 or 7 in the morning now and after having no luck finding an escort I responded to an ad on craigslist posted by a trans woman. I figured two things, this dick isn't going to suck... Read full Story
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BANGING AROUND BANGKOK
BANGING AROUND BANGKOK: THE AMOROUS ADVENTURES OF CAITLIN "MEOW" MORRISON after living and working in Thailand/SE Asia for many years i decided to write an erotic story based on some of the people i have known, venues and places i have been, and the P4P night-scene where i spent way too much... Read full Story
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My first time with a shemale
My girlfriend had been out of town for a couple of weeks and i was so horny and wanted to get upto something kinky. I called a shemale site from la costa del sol called taiakshemales and arrange to meet one of the beauties. I was very nervous as i drove to her house as i never touched a dick befor... Read full Story
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My Dream Cums True
Me and my girlfriend would always talk for hours about our secrets and feelings and as the night would progress we would get into more sexual subjects but this night would change our lives forever..... ''so what's a sexy secret you have that no one else knows about?'' I asked my girlfriend. ''... Read full Story
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First time and what great fun
My name is Jakub, or Jake as my friends call me. At the time this little adventure took place, I was 20 years old and I guess I was a pretty lonely guy. Overall, I am a pretty average dude: 6 feet tall, slim body and average looks, the only thing about me that’s a bit different than most peopl... Read full Story
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My Overseas Experience With A Bunch Of Shemales
I spent my first year in the states and then got transferred to thailand where my story really begins.We landed in bangkok and after we got settled in we headed downtown because we knew this place was full of whores. We spent the whole night drinking and fucking. I saw some of the most beautiful wom... Read full Story
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My second time with Jake
The week after my first experience with Jake was amazing. I had finally sucked a real cock and I wanted to again. All that week Jake kept texting me pictures of his hard cock. I couldn’t believe that he was into a gurl like me. On Thursday of the week he texted me another pic of his cock and t... Read full Story
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Party Surprise - First sex as a Crossdresser
This is a work of Fantasy. I hope you enjoy. Stephanie and I had been married a few years and enjoyed a reasonable sex life. She knew of my dressing and although she didn’t approve she indulged me now and then and we had sex when I was dressed or with me wearing lingerie. I think secretly s... Read full Story
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My first time with sheilacd
U know exactly how to please a man. u make it hard to say no...(as my cock grows again) even when u come in to kiss a straight guy he cant deny ur feminine essence that is so strong his body betrays him. he surrenders knowing he is in good hands..."soft white hands" he knows his manhood ... Read full Story
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The first tranny I looked for
So i've had some tranny experience unwittingly. I respond to this ad on craigslist from this 19 year old tranny who lives fairly far away, but her picture was so sexy I decided to take the hour drive. So I drive to her parents house, nervous the whole way, when I get there I get out of the car. Ston... Read full Story
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One experience with two black men
Hello again this is EvA…I am a 40 year old tranny. I do not consider myself a cross dresser anymore, because I am doing that for so long that I have been transformed to a very sexy and feminine lady boy. I have been taking also hormones for 4 years, on and off and I already saw many changes&h... Read full Story
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My first big cock
So I'm deciding to post a story about an experience I had about a year ago. Ill start with a little background about me, I'm a bi crossdresser 22 years old 5'8" 140lbs, newly exploring bottom, very passable crossdresser. And extremely selective. I tried an online dating site ... 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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New Leila
I'm an ordinary guy, nothing special about me at all. Well, maybe my choice in women could set me apart from most. It all started one rainy afternoon in Northern California as I was driving home after a party I'd attended alone the day before. I'd stayed over at friends and after a nic... Read full Story
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How I became a Transexual
I was driving a different way home after work and noticed a kind of sleazy looking sex shop. Not really wanting to go home yet, I decided to stop, it had been awhile since I'd had sex and was horny. I went in and was browsing around the movies section when I noticed there were doors in the back. I w... Read full Story
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My first shemale sex
I had developed a strong desire to be with a hot looking shemale for a long time. I really did not know how to make contact with anyone in the small city I lived in, and figured it would likely never happen to me. One day at work at my computer support job, I was informed that another branch of our ... Read full Story
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Got fucked by a tgirl yesterday while standing up
I got fucked by a tgirl yesterday while standing up... a first for me and pretty good experience... here's the story I visited a new t-girl, for the first time, and decided to try something new, well, to be honest, she encouraged me to try something new :) I had seen a pic, with my new tgir... Read full Story
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I fucked my personal trainers ass for the first time
I greeted him on my bed in my sheer black lingerie. I knew he’d be nervous, and truly I was as well. We’d spend so much time in the gym together and I knew he wanted me, but taking that next step was sometimes difficult, especially when our relationship was always professional. Posing for him, I r... 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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My First Ladyboy
I was working in Bangkok a couple of years ago. As was the normal practice all the guys would finish work on a Friday afternoon and head to the local bar for a couple of beers.. This particular Friday we were in the usual place chatting and having a nice relaxing time......when she walked in....t... Read full Story
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My Descent
This is the first time I've told my story publicly. I wrote this maybe 3 years ago, and have shared it with one person. I used to cross dress in my hotel room while away on business trips. I'm a fat bald 46 year-old who looks ridiculous dressed up in ladies underwear. When you're obsessed, tho... Read full Story
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First Public Experience
From my previous stories you’ll know I love to dress up in lingerie. After a small number of sexual encounters with men I decided it was time to take things to the next level. I told a lesbian friend of my cross-dressing and asked her to take me to a gay nightclub dressed as lady. I didn&rsquo... Read full Story
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How I began my crossdresser transformation
Here are the usual disclaimers this story is for adults only if you are viewing this and are not 18 years of age or older please close this page immediately. There is no crossdressing in the story but this is how I began my transformation from regular boy into cock sucking teenage crossdresser.... Read full Story
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Yes, I used to be Straight....Pt. 1.
The title came as an answer to an inbox question from a trans-sis... We were chatting about how some of us stay off the radar when it comes to sex (sexual acts as your feminine self); and some of us fall off the deep end. I gave my personal experience and thought I'd share the story with you (f... Read full Story
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Once wasn't enough!- my 2nd shemale exp
So after my first experience I got really into the porn I bought movies magezines got on websites just couldn't get enough. But watching it wasn't enough I had the real thing once and wanted it again. It had been almost a year now and only one person knew about what I had done that one fat... Read full Story
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Experience The Best From Thailand On Thai Shemale Tube
The chances are that you have probably seen "The Hangover 2", but thought that the shemale scene can happen only in twisted imaginations of Hollywood screenwriters. I am here to prove you wrong. If you don't believe me, go to Thai Shemale Tube and see it for yourselves. My best friend J... Read full Story
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A Night Downtown
It was a brutally cold winter night, even by Minnesota standards. It didn’t matter. I was just beginning my journey towards womanhood and needed to get out on the town for some much needed male attention. Technically, still in the closet, care was needed to make sure it went undiscovered anytime I s... Read full Story
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My Virgin Tale
It was a brutally cold winter night, even by Minnesota standards. It didn’t matter. I was just beginning my journey towards womanhood and needed to get out on the town for some much needed male attention. Technically, still in the closet, care was needed to make sure it went undiscovered anytime I s... Read full Story
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My First Sex Session
I am an Asian crossdresser living part-time. The reason I decided to dress is ever since I was little, I had been getting signals. First at my boarding school when I was fourteen, which is where that experience happened. Every Wednesday night was devoted to activities run by your adviser. I had an a... Read full Story
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First Cross-dressings Loosing Anal Virginity
It happened after a month of me blowing that guy twice...I mean I was so damn excited and was craving for his cock....I was blowing him every weekend in his car after the school...his cock was almost 7 inches and was so thick and that I like so so much the gagging he was giving everytime, that chock... Read full Story
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First Time Shemale Encounter
Lets start off by saying this a very true story, one that i love to re-live over and over. lets begin I was in el paso, texas..my girlfriend at the hotel. Something in me decided to go to the strip club. So i did. After a few dances, i decided to leave. I had always heard in mexico it was very ea... Read full Story
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Jack & Jill - his first time with a transexual
Jack and Jill meet It was when I went to the patio to enjoy a cigar after dinner that we met. On the road for business, I found a decent bar and grill near my hotel where I was welcome to enjoy a fine smoke. I had dinner and then moved outside for a relaxing smoke in the cool weather. I lighte... Read full Story
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Eric...a
There was no doubt that this was going to be my last baseball game in organized ball. I knew that after high school I would not get a chance to play anywhere else, save for the drunken beer league down the line. I was an average player who played for a small school. I played second base. We were los... Read full Story
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First time meeting with another CD
I was online and a message popped up from another Cd who lived local. He was married just like me and loved dressing up. We chatted for a few days and then he asked me over to his place as his wife was working. I had a few hours spare so i packed a few things and went over to see him. when i turn... Read full Story
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Fixing her computer
I repair computers, often "on site"--in people's homes. I got a call from a woman asking me to come to her house to fix her PC. She told me her name was Shandra. We made arrangements for me to show up there Saturday afternoon. I showed up at the appointed time and was surprised when I s... Read full Story
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First time with CD when I wanted tranny
(True story)I got in touch with an asian tranny online (as most people do lol). I've always had an attraction towards trannys, especially really sexy black ones which appear in porn but i've never fulfilled my fascination. I'm straight and have slept with the sexiest women going but have a curious s... Read full Story
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