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My first time having sex with a Tranny
I have been obsessed with Trannies for as long as I can remember. There is something about a gorgeous feminine woman with a big thick cock that drives me crazy! I turns me on so much that I kept pushing myself further with my love for Trans women. I bought sexy dresses, underwear and heels to wear s... Read full Story
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First Time I Experienced Eating a Tgirl Out
So this is likely going to seem tabboo for some and if this is not your thing, I respect that but everyone is different. Eating pussy came natural to me like it does for most guys once they start having sex with girls. Other than one time 69ing with a female and having what I would call "incidental ... 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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My First Time
I have a few stories of meeting TS girls, this is of my first experience. So this happened a few years ago and I was really interested in meeting a TS. I kept trying to meet one with no luck, then one fine day I meet this super sexy Asian goddess. This was my first time and I was nervous. We go t... 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
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 crossdressing with a man
It was Christmas night 2016 and I had gone out to the bar with a few friends. Came home a little tipsy and very horny! I rushed to my room, took off all my clothes and put on a very sexy, slutty outfit (black lace thong with matching bra, a blue sweater, black mini-skirt, and black knee high boots) ... Read full Story
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First Time: How I Love Cock
The first time I ever sucked a dick was when I was around 12 years old. I was at a sleep over with a friend. We were camped out in his backyard in a tent and he started things out tentatively by asking about my luck with the ladies, which was non-existent. Then he suggested that since neither of us ... 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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First Time I tasted Tgirl Sperm
I met a Mexican Trans girl online from Hermosillo and we hit it off and corresponded for a a few months. The vibe was good and ended up deciding that I would help her pay the $140 bucks for her 6-month tourist visa to come up and visit..the process took forever but once she got it, I booked her a pl... Read full Story
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First Time With a Shemale Part 2
"WOW" I thought to myself "I'm gonna fuck a hot Asian hooker for free!"...She took out my cock and started playing with it, "I love your cock babe,mmm I want it in my mouth" and she slowly started sucking on it. Now back in the days I wasn't much of an expert, but that ... Read full Story
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It was my first time
So I met this trans girl thru backpage & her pics were above average so I decided to go for it. I set up meeting, drove out to hotel, knocked on door, she let me in & we stood there looking at each other. She was a mixture of Asian & Hispanic. Pretty nice tits, long legs & didn't look like much fat ... Read full Story
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My First Time
When I was 18, my mom and I moved to a little town on LI. Right next to our house was a largely used road even at night. Right on the corner of my street and that large street was a gas station I always bought cigarettes from. Right next to the gas station was a bank with a parking lot that ... Read full Story
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First time crossdressing exp
well this hapened a few years back,ive always been into wearing lacy underwear etc so i put an add in for anther knicker wearer for fun in an adult contact site,and was amazed at the replys,anyway i met a guy and we got on so we arranged a meet later that week at his house,i got there had a couple o... Read full Story
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First time with ladyboy / bottom
Hi everyone! now it is my turn to share my experience in Thailand. We were on a Christmas vacation on an island, and I didn’t even know ladyboy existed then. At a Christmas beach party I chatted and danced with a woman and we ended up in my bungalow. We kissed a lot and I knew that now I was g... Read full Story
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First Times
A little background is in order. During my teen years, I became involved with a woman that helped me discover the pleasures of my female side. Sue helped me to dress and act in a very feminine manner. We were almost like sisters in the way we became so close. She would sometimes describe how good... Read full Story
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My first encounter
This story details my first encounter with a stranger I met over the internet. I was 25 and reall getting into being a girl, I dressed all the time, and dreamed of sucking a cock dressed as who I really wanted to be. So I took a plunge in meeting someone for a quick bj in the area. I sent him some p... Read full Story
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A Schoolgirl's First Time
I’d been emailing and phoning Dan for several weeks when he first suggested that we meet up. It was very exciting and I couldn’t wait. My every waking hour was spent thinking about it. The only odd thing was the request he’d made. “Can I ask you a bit of a kinky favour?&rd... Read full Story
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My first cock sucking
NOTE: I would like you to know that English is not my native language. I hope you can understand my writing, despite any misspellings or bad grammar. Thank you. Is just wonderful read all the stories here on this website, so I decided to write more and give you my little contribution. This is ... Read full Story
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"Just Treat Me Like A Lady" My First TS
I had just moved to San Antonio for a new job. I only knew a few people from work and asked them where I should go for some night life. They told me to go downtown and gave me the names of a few bars. I was 27 at the time, athletic, a little over 6'0" and about 175." I have a good body and dress cas... Read full Story
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2nd date with Latina Sissy Destiny
So this was my second time with Destiny, a really cool Latina CD/Sissy who had just turned 22. You might want to read my first goaround with her title, “Deflowering Latina Sissy Destiny” as it will give background and context here. After our first encounter, she signaled that she was definitely... 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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Roberta, Molly and Ed
Friday "Commander Cromartie?" Lt. Commander Edward Cromartie, USN, turned toward the voice that had spoken his name. He saw two female naval officers, a tall willowy light-skin Black woman, and a short Asian one. The Black one was wearing the uniform of a full commander, the Asian of... 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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My Asian Boy dresses for me
I asked my 18 year old Asian Boy James if he would consider dressing up for me? He seemed reluctant at first but the next day he told me he would only wear a little makeup and panties , that was good enough for me cause within 20 minutes I had him bent over and I was licking his tight hole getting i... Read full Story
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Chicago TG Romance
Most transgendered girls I have met want to be treated and romanced just as a normal girl would. Only in the height of passion should your animal instincts take over. I was in a Las Vegas club earlier this year and had great conversation with some tranny women. I was instructed if I wanted to meet s... 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. Taller t... Read full Story
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First time in Key West
I've always been fascinated by shemales.  Aside from having an overall appreciation for how the male member in general functions and, when properly stimulated, pulses and pumps...cum spewing from the tip.  I've watched any number of webcam shows where guys jerk off.  And yeah, I've wa... Read full Story
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First time with a cute ladyboy
It had been a long week at work. So I decided to go to the Sound Factory for a drink and maybe get lucky with the ladies. As soon as I got to the bar, I spotted a beautiful asian lady wearing leggings with pantyhose and a sexy little top. She offered to buy me a drink, who am I to refuse. So we had... Read full Story
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How I became a ladyboy convert
Our friend Brian went to Thailand 3 years ago and had his first experience with a ladyboy details of which he would like to bring to Your attention now. He proudly tells he became a ladyboy convert after his first time and we have no doubt he did! On a trip to Thailand about 3 years ago I had my ... Read full Story
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First Fuck For Straight Guy
This past February 2nd was my first time of being fucked in my asshole. The only word I can use to describe the experience I had is unbelievable. Mixed emotions and sensations came over me that I was so horny I wanted the guy to fuck me rough. I was literally backing up when we're in doggy position.... Read full Story
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Becoming addicted to her she-cock
"I'm going to make you a very happy woman tonight when I slowly but firmly slide my long, thick, hard she-cock all the way up your tight virgin ass tonight baby" Alma whispered in my ear as we left the bar I had ?mistakenly? stumbled into. I shuddered with both fear & a bit excitement. I don't why ... Read full Story
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How could I forget my first time .......
"Ok, ok, ok stop. No more. It hurts a bit" I said. "Just relax your ass baby. Push out like you have to go poo", my date said. How did I end up like this? A straight A college student, a devout Christian with a nice gf like me ends up in bed with this sexy woman ...... Ok wait, I thought she wa... Read full Story
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My first blowjob
I met a shemale online called melisa and we had been talking over msn for afew days, mainly having saucy chats about sex and getting off. She asked me to meet her on the coming weekend which excited me as i was a virgin to cock. We arranged to meet in a bar that was a stone's throw away from my f... Read full Story
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My First Blowjob
Fuck! I'm so jealous! Back in my teens I could self suck! I'd lock myself in the bathroom, lay on my back and bring my legs over top. I was able to not only get the head of my.cock in my mouth, but half of my length as well. The first time I nutted in my own mouth, I wasn't prepared for the big lo... Read full Story
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First Tranny Experience_Part 2
I had said good bye to her at her door and drove home. I got home at a decent hour and went to bed. The following day at soccer practice, I could only think about how wild a time we had together and began fantasizing about the whole affair when my cell phone went off. To my surprise, it was Kim s... Read full Story
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First time with a trans escort
I've thought about seeing a t-girl escort many times and a few weeks ago I finally made a date with a local girl named Carol. She´s a lovely Colombian girl with long dark hair and a slim, sexy body. She welcomed me into her home wearing a sexy black dress and high heels and after pouring a d... Read full Story
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My first time getting a big cock in my ass
I got talking with a relatively local guy, much older than us, but had a thick 8.5" uncut cock, which was perfect for what I wanted to watch enter my Mrs. Our messages went something like this... Me "Did you want to meet up first?" Him "If you want" Me "We'll chat about a plan, then I'll... Read full Story
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I met a guy in the nightclub and I didn't tell him I was Trans
I’d worn an absolutely killer dress just to make sure I got what I was looking for that night. Dancing under the lights I could feel eyes all over me, and as the evening progressed men became bolder and bolder about approaching. This one was athletic, sexy and had all the right dance moves, at least... Read full Story
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Becoming a Sissy Cocsucer
I always loved feminine things. I'd wear my s****rs panties as often as I could. I loved the way they felt, the soft fabric, the high cut legs, and especially the frilly lace edging! I graduated to bras and padding them and wondered what it'd be like to be a girl. I always loved watching porn whe... Read full Story
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First fuck in public ;)
You’re only wearing a coat, I find a place where, I can kiss you then slide my hand between the flaps of your coat. I expose your breasts and slide my hand down across your tummy down to your pussy. My fingers start to explore your soft bush, working there way to your soft pink lips surrounding your... Read full Story
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Fun With Friends
I am a 28 year old single heterosexual male who happens to enjoy cross-dressing. It started with the desire to wear high heels and after that developed into pvc, leather, latex...anything slutty to be honest. The thought of being caught while dressed as a woman gives me an equal measure of excitemen... Read full Story
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My first sex as a gurl with others
Had my first sexual experience as a gurl that wasn't by myself last night.... Left with alot of mixed feelings, had some.fun bit didn't turn out exactly like I would have hoped... Thing got a little weird at the end Well it started off great she was insanely hot, the CD husband was better t... 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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Sally's First
My heart was racing a mile a minute as my hand reached for the door knob to open a whole new world to me. Although I had been dressing for about 15 years, at 23 I still hadn't been outside or let anyone in on my secret. The last 3 years had been hell for me as I had started to play with dildo's a... Read full Story
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My first time as a Femboy CD pt 2
David ordered me to dance for him and I hurriedly got off the floor and walked over to the radio and turned it on. I changed the station from an alternative rock station to a top 40 one, which was better for dancing. After I selected the station I moved to the center of the room and started to dan... Read full Story
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Slut indiscretion
At 17, I had reputation among the people in my world. I had sucked more dicks than the average hooker. I had slept with men of every race creed and color. You can even throw in a mentally challenged lad or and autistic child as well. All because I loved getting sex. I think that a penis is the sexi... Read full Story
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Slutty Sissy's 2 Loves
Tonight was young and I was already hot and bothered, my ass-pussy was on fire, and I could hardly wait for Bob and John to come over. I had invited them over to fulfill those erotic dreams I am constantly having about the two of them using me like a tool, and I wanted that so bad. I fantasized abou... Read full Story
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TO BE OR NOT TO BE - PART 7
TO BE OR NOT TO BE - PART 7 by Spanky de Bautumn Part 6. Sunny, Mel, and Shari had a heart to heart and Mark took Sunny for a night on the town. I woke up next to Mark, he looked so peaceful sleeping. Was I dreaming? Did I fall asleep and dream that Mark said he was going to take me shopping... Read full Story
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Daddys Little Slut
I have been living with my dad for the last year after my mum who is Indian, found out that I was doing lots of drugs, and that I was bi and also a cross dresser. We never talked about it as for me, the cross dressing was on and off and usually when i was high. When i turned 25, I tried meth, and fo... Read full Story
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The colossus and me
The colossus and me... step by step towards completion (1) When my phone rang I was watching the World’s news in TV, only tragedies. It was Lina (cf. my previous story) on the phone. The colossus with an angel heart and an elephant dick. She was in my town for business. And without her saying ano... Read full Story
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Sally
The first time I met Sally I was amazed. She was a gorgeous brunette, about five feet six inches tall, shoulder length hair, nice firm, round tits, and an ass to die for. It was late in the evening when I got off work and uncharacteristically, I decided to stop in at Varsity's for a drink. Orderi... Read full Story
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Caught by Dave!
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. No one I know even suspects that I'm a slut at heart or that I am the least bit bi. But more and more I keep fantasizing about one of my male friends. He's very good looking and keeps... Read full Story
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Tea-Girl's Repeat Performance
It was the last night before my girlfriend was due back from the Hen Night she was on, and I had already washed her clothes from my previous day's fun with the electricity meter reader, during which I made a mess of her satin thongs, pantyhose and white body-tight top. I wanted to relax, with a bott... Read full Story
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Only Once
She looked as rich and a chocolate bar and I'm sure she came with nuts, by the looks of guy who seems to walk one step behind and just to side of traffic. We had exchanged pleasantries a few days ago at an art show of a friend of mine. There she was with a diamond the size of a dime and a neck lace ... Read full Story
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My Sweet Little Crossdresser
Monday morning I woke up, still somewhat tired from the night before, asking myself if it was all real or just a dream. I then remembered that I had taken that cute guy's panties and put them on my neighbor's door, so I walked out into the hall and looked down to her door and, sure enough, there the... Read full Story
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