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My first Tranny
After a recent breakup and a few years of fascination I finally got the urge to post a M4T wanted add on craigslist. After several unwanted offers from old men I was finally send pictures and the number of a sexy Latin shemale named Ana. After exchanging text messages for about 15 minutes I was fres... Read full Story
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My Start
In the beginning, when I was younger and trying out my sexuality and starting to understand what I wanted and liked and craved and needed, I played with boys and girls. But in short order, I decided I wanted something in between. Which is how I would find myself sneaking into clubs in Manhattan in t... Read full Story
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My first blowjob from a hot transexual next door
In my neighborhood there's a transexual friend of my mom, she owns a salon, and it was frequent for me to wait for my mom to get her hair done, while i just looked at her discretly, she was around mid thirties, with a very hot body and beautiful blonde hair, it was a common sight to watch her walk o... 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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Tranny Night Out
Tranny Night Out and One Kinky Session Guess I should start by explaining myself, as a young guy I always knew I was not the same as a lot of my friends and enemies for that matter, girls had no interest in me at all apart from ones who were long term friends. I knew something was wrong but neve... Read full Story
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The Magic of my first Blac Coc
Wow! This was my first real experience with Black Cock. it was right after my divorce. I was in my late twenties. I ran my ads as a crossdresser on a few dating sites and on Craigslist. I received a message on my AFF site from a member whose profile name was BBCRicky. My interest was immediately... Read full Story
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Manusha sleeping with a bank manager for loan approval
The incident of this story is almost 5 years old and this happened between me and a bank manager in a leading nationalized bank and you know for what he was demanding a favor from me? Hehehe.. That’s in the story..! This was in 2015 when I applied for a personal loan from one of the leading nati... 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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Kelly's first cock
I've been dressing on an off for as far as i can remember, starting when i was at school, coming home early and putting on my mum's lingerie and heels and wanking myself off looking at my reflection in the mirror. However, it wasn't until i went to uni that i started to get into tranny porn, where i... Read full Story
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Shemale Public Bondage Fantasy
It was a chilly evening, I had arranged to meet him in the city centre. I was wearing a rather skimpy black dress, black lingerie and red high heels. It was my first time dressed in public like this. He was an average looking man, he shook my hand and kissed my cheek, and asked if I was ready. I aff... Read full Story
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Making of a Sissy pt2
After Tom had dressed me & now had the photo evidence I knew I was at his mercy. I also knew that the blowjob I had given him wouldn't be all he was looking to get from me to keep my secret. He was soon messaging me, telling me when to be at his, along with a picture of me dressed, with ... Read full Story
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Shopping plus extras!!!
Hi, so as you can probably imagine I buy a lot of underwear and have a few favourite places to shop. My favourite by far is Ann Summers. The range is great and the staff are so helpful . Anyway back to the story. So I decided to go get some new underwear to see in the new year, I got myself up and d... Read full Story
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My Date with a Crossdresser
A couple of months ago, I was contacted by a crossdresser here at Xhamster. She has asked me not to reveal her identity. We arranged to meet one night at a motel near the Pittsburgh International Airport. I arrived at the agreed time, but when I knocked on her door she told me she wasn't ready ye... Read full Story
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Jordan's First
My name is Jason, I am a 33 year old road worker. The pay is okay but I never had much more than what I needed to live comfortably. I was hoping to save up for a nice vacation and decided the best way to do that was to take on a roommate. I live in a decent sized two bedroom apartment and the seco... Read full Story
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My First Gangbang
For as long as I can remember, I have always enjoyed wearing women's clothing. When I was in fifth grade, I started wearing pantyhose under my pants during the winter. By the time I was going into the seventh grade, I had learned that, not only did I enjoy wearing pantyhose, I also liked playing wit... Read full Story
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Proud To Be A Sissy Chapter 5
I awoke in almost total darkness, only a soft glow came into the hall from the kitchen. At first wondering where I was, my bed at home wasn't as soft as where someone, probably my new daddy had carried me after falling asleep on the floor. I shivered in delight remembering how my daddy had shared me... Read full Story
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Caught Crossdressing by a Real Man
This story is a continuation of night club cum slut. Ever since I first wore panties for a boyfriend, I had built up a collection of lingerie. I gradually worked up from panties to the most erotic lingerie I could find. My fascination with cross dressing went a little further with a new fetish f... Read full Story
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CD Jinn and Football Jerry
Last weekend my college football team was throwing a party during their off season as a way to relax and take their minds off school and football. I am Jinn a very limited experienced Cross Dresser. I have only ever experienced one man and one strap-on girl. The man was Jerry he was a college foot... Read full Story
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Bikini contest
I was at this beach bar in Mt Pleasant SC. There was a bikini contest that day. As I attended, the contest started. I was 23yrs old and the thought never crossed my mind about a tranny. However this was supposed to be all girls. Nobody, including me suspected this girl that won the contest was a tr... Read full Story
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Vanessa and the workmen gangbang
The three workmen were slaving away in the back garden, in the hot sun. Vanessa watched them from the upstairs bedroom window, getting more excited by the second. Under her robe she was wearing a beautiful red basque with a red g-string, black stockings and five inch heels. This was topped off with ... Read full Story
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Regina’s Double threat.
Hello guys, I recently ran into a former hater who was no longer the hater I had met years earlier. In fact, he had only treated me so horribly because of his own inner dark desires. When we met a few years ago at one of the clubs, he had been very abusive to me. He went out of his way to say hurtfu... Read full Story
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TV Times
One evening I was online when someone wanted to start a chat with me. It was a bi guy who enjoyed cross dressing and having viewed his online profile I said "Hi" and we got to talking. He was married guy named Mike and he had a very understanding wife who allowed him to meet men and a... 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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Caught by my wife
I was stuck, I couldn't move, literally in headlights... I dress up okay? you caught me, I guess your the master now... I used to control my wives life and for good reason I pleased her, and she pleased me the best she could... well now that's changed.. she came home from work early last Tuesday and... Read full Story
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First Time Drag Chapter 2
We'd been together for almost one full year, maybe the happiest year of my life. Michael had expanded his feminine side, dressing up and wearing makeup more often than not. His hair had grown too, now almost at shoulder-length. Though twenty-one, he was still really just a boy, or maybe just a girl.... 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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First time being dressed as a woman
I'm a 42 year old married bisexual guy, slim built, average height and shaved below. Ive had a few encounters with other men but none dressed as a Woman. Ive had fantasies for years about wearing women's clothes and make up. Unfortunately I haven't had much opportunity for either, that was until a... Read full Story
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Chicago TG Romance (part 3)
It is Sunday morning, just barely dawn and I have just spent the weekend with the most amazing girl. You know when everything clicks and it seems that at first you have met the person you want to spend time with and share with. Beth was standing at the glass windows full length and the sun was just ... Read full Story
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TO BE OR NOT TO BE – FINAL ACT
TO BE OR NOT TO BE – FINAL ACT by Spanky de Bautumn Part 7. Sunny spent the night with Antonio and the next day they went to Mel and Shari’s for some fun. Antonio had school, so he was up and out early on Tuesday. Mel was in the shower and I was laying in bed, my mind wandering and not real... 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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Alessia Mixes Politics and Pleasure
Victoria University is a prestigious institute of higher learning in Manchester, England. On this unusually warm day in May, a buzz circulated throughout the campus. Alesia Travestita was going to deliver a course in Political Theory. Alessia had given a popular course the previous year, but she sto... Read full Story
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Candy's Treats
"Hi, I'm Candy," the pretty blonde Latina said to me as I sat alone in the casino bar. She had a nice pretty face and a great body with a store bought pair of dd's. I knew the moment she sat down that she was a pro. Five straight years in Vegas at the show had taught me how to spot them in... Read full Story
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Bi Pantyhose Passion
I've had a Pantyhose Fetish for over 30 years now, and love wearing them on a daily basis. But back in the summer of 1995, I suffered a heat stroke, and almost died, when I recovered, I vowed I would stop fantasizing, and live out these dreams and fantasies. I had been masturbating while dress... Read full Story
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Fantastic Weekend - First Touch
It finally worked! After a year of posting ads on Craigslist, and what I'd decided was my last attempt, I got results. It was short and to the point, "Panty Sub Seeks Oral Top." As is normally the case, I got a lot of one-line responses and picture requests, but buried in there were two gu... Read full Story
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Adam Picks Up a Transgender
Sitting along the short L stretch of the bar, Adam admired the pretty girl sitting most the way down the longer length of the bar. Her blonde hair was long and curly. Her tight dress had a swoop front that showed plenty of cleavage. He knew the rumors. She wasn't completely a "she." She wa... Read full Story
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Find That Guy: Porn TV's TG Gameshow Round 02
"Welcome back, ladies and gentlemen, for round 2 of FIND THAT GUY" said the host, giving the camera his cheesiest smile. "We left off with our couple Sue and Winnifred holding only 7 points, and one of their opponents, Vince, having been disqualified. Their remaining opponents are Ric... Read full Story
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Sissy schoolgirl and her black daddy
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 m... Read full Story
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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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Business trip
Craig and I were salesmen for the same company and on a trip together to woo new clients. The last thing I expected was that we would woo each other. It had been a long day and we went to our rooms to relax and unwind. After I had my room service and wanted to go over the proposals I realized Crai... Read full Story
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Emily's First Daddy
This is a story how a curious male can become a sissy slut seemingly overnight. So I was in an online adult chat just talking with random people and happened to mentioned where I live. Then all of sudden, I got a message from a man calling himself bear daddy. He introduced himself and said he was ... Read full Story
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TO BE OR NOT TO BE – PART 6
TO BE OR NOT TO BE – PART 6 by Spanky de Bautumn Part 5. Sunny and Antonio got frisky at the bar, Sunny moved in with Mel and Shari, and opening night was a success The only other dress that I brought was one that I hoped I would get a chance to wear but didn't think I would. It was a black ... Read full Story
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TO BE OR NOT TO BE – PART 6
TO BE OR NOT TO BE – PART 6 by Spanky de Bautumn Part 5. Sunny and Antonio got frisky at the bar, Sunny moved in with Mel and Shari, and opening night was a success The only other dress that I brought was one that I hoped I would get a chance to wear but didn't think I would. It was a black ... Read full Story
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Beryl's birthday suit
I tried on my sister's panties when I was 12. They looked so cute, so sexy.. I couldn't help myself. I tucked my dick between my legs and pulled them over my hips, delicately positioning them just like a girl. They felt yummy! When I saw the shiny, lacy pink briefs in the mirror - snug, flat pu... Read full Story
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Don/Dawn of the Dead
I did all of the 'normal' things first. Checked all the doors, checked all the stores, closets, back hallways, stockrooms and bathrooms for zombies. Made sure everything was sealed off. Established a base inside the mall to operate from. Made an escape plan. Hid some of my guns and ammo in a cache w... Read full Story
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Proud To Be A Sissy Chapter 8
I woke up to hear daddy lightly snoring and in my sleep I had draped a leg over him so that my body was almost covering him. I giggled to myself realizing that even in my sleep the sissy slut in me reached to grasp his flaccid penis. Then I curled closer up against daddy and contemplated about how m... Read full Story
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TO BE OR NOT TO BE – PART 2
TO BE OR NOT TO BE – PART 2 by Spanky de Bautumn Part 1. Sunny, Mel, and Shari learn they are going to New York to perform a play off Broadway and are really excited about it. Being a small troupe, we unseen members had to wear many hats. Unfortunately, there was just the two of us, Joe Donn... Read full Story
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TO BE OR NOT TO BE – PART 3
TO BE OR NOT TO BE – PART 3 by Spanky de Bautumn Part 2. At the hotel in New York City, Sunny meets the bellhop, Antonio, and they go out for a drink when he gets off of work. The call came at exactly seven. I had woke up about five minutes before and was watching Antonio sleep. All of the oth... Read full Story
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Camming Down the Rabbit Hole Ch. 08
A familiar sensation greeted me as my eyes opened and a yawn escaped my mouth, that oh so delicious feeling of my morning wood straining against my silk night ware. It was becoming an ever occurring pattern that no matter how large the orgasm the night before I would wake with the hardest of cocks, ... Read full Story
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Aunt Susie's Training Part 4
My Aunt Susie grabbed my hand as I stood in my towel and made me sit down at her 💄 makeup table. I basically had no facial hair so the foundation was applied all over very easily. Next she started doing my eyes with a purple mauve shade of eyeshadow. She put on eyeliner and then mascara, then blus... Read full Story
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Unforgettable First Time
I am in my late thirties and have known for a while that I have a sexy body. I'm 5'11", slim and athletic with little cherry butt and shapely legs. A lot of women have told me my body is sexy. A few men have mentioned it too. Sometimes I get photo-snapped at the pool or the beach. I've been luc... Read full Story
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Elizabeth: Beginnings of a Sissy
I had a pretty good system going. My 18 year old sister would stay up to watch Sex And The City reruns with me (well she watched, and I smoked weed), and during the first ad breaks, would run downstairs and get changed for bed. During the next ads, I would go to the bathroom, and on my way, raid her... Read full Story
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Love to Fantasize
I love to fantasize; it is one of the greatest things on the face of the earth. I have many fantasies, tho I have given up on a couple since I married my wife. I am a white male of 27 years, and since I was sixteen, I have had many erotic fantasies stemming from reading my parents adult story magazi... Read full Story
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A Night of Lust
I was out at a night club with a few friends, and we were there for for a while before I noticed this sexy, rather short girl across from me at the bar looking over. I could tell, even from this distance that there was something special about her, I wasn’t sure what that was quite yet though. The mo... Read full Story
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Becoming Zoe
My soon to be wife Annie had taken a job out of town and I only saw her every two weeks or so. I was so missing her. She and I had become long distance lovers. She was scheduled for a flight home on Friday night. I was going to pick up her son Zakk from his dorm and the two of us were going to p... Read full Story
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TO BE OR NOT TO BE – PART 1
TO BE OR NOT TO BE – PART 1 by Spanky de Bautumn This is a story about how taking a play to New York City changed people's lives. A transgender coming of age story. I was born Harold Stanley Dayes, not a great name for a kid growing up. I know my parents loved me, but Harold was my mom's dad a... Read full Story
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intimate Cousins
My favorite cousin and first lover, Billy, was just released from prison and I was anxious to see him. I am ecstatic that he is out, and I am thinking about all the past fun we had as I prepare to revisit those good times. Tommy knows all about my relationship with Billy and he understands my need t... Read full Story
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