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My first date with a "shemale"
I met a guy whom i worked with and found out he was bisexual,it didn't bother me nor did i care because i know who i was.I realized he was trying to date me without asking me if i was that way.I flat out turned him down and told him i didn't go that way! I was still young and new to this. I was coo... Read full Story
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Big On Tranny Dating
I walked into a bar where we scheduled our date earlier - I know that type - he wants to try tranny dating but when it comes to real thing, he'll probably chicken out and ditch me. I ordered a large martini and looked myself in the mirror: tall, strong legs, curly blond hair. You couldn't see my ... Read full Story
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Big Cock Heaven
This story is written from the Shemale's point of view. "Jane" is based on a real Transgender woman from California & my friend. She gave me the outline of a meeting she had with "Janardhan." ***** My name is Jane and I am a natural red head blue eyed 34 year old T... 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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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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Chasity's white pussyboy
I led Chasity into the apartment. She was looking for a one bedroom, furnished place and had called about my ad in the newspaper. I hoped to rent this place quickly, then I would be full and could devote my time to some maintenance and repairs rather than showing places. I looked at the renta... 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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White fuckslut Tgirl & 3 BIG BLACK COCKS Initiation
You lucky, slutty BBC Tgirl fuckslut, I envy you soooooo much. This is the most erotic and best BBC story on this web site. Pleeease keep writing about your BBC fantasies. What a bargain to get gangbanged by about 30 big black studs for only 15 Euros. I loved it when you begged them to fuck you.\r\n... 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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TGirl Initiation by 3 BIG BLACK 12
In my teen years I was often told that I was quite feminine.The high school punks always told me that I filled out the back of my jeans in a girly way. After taking a shower one day I did notice that they were right, I had a nice white bubble butt. Not to mention that my lips were also quite girly. ... Read full Story
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I Fooled Everyone But the Black Pimp Part 1
So I’m sitting at the pub drinking with the guys and talking sports and pussy. I’m wearing work boots, jeans and a white T shirt. I’m also wearing purple panties and a butt plug wishing I was getting spit roasted by big cocks. I'm very restless on my bar stool as I grind my hungry hole down ... 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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Teasing BIG BLACK COCKS at truck stops
I'm a white blonde bubble butt Tgirl living in Las Vegas and sometimes I go out and cruise the truck stops on I15 down south to I10. I do it at night and sometimes for a whole weekend in my mini van which has darkened windows. I love to get out of my mini van and walk around the back parking row at ... Read full Story
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My first BBC fuck
I went clubbing last week with my girlfriends that I work with and they recommended a hip hop club in a seedy part of town. I was alittle scared but we went anyway and well, and we were really having some fun there!!! I decided to dress like a real lil slut this night, a black minidress, lacey thigh... Read full Story
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My first time with a man
I have been dressing on and off for many years. But one time when I was feeling more like a woman I decided to join a site where I could meet men who liked girls like me. I met a wonderful man and we constantly kept in touch with each other since he lived in another state. Well he told me that he wa... Read full Story
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Bang in the Backseat
I am all bottom when I am with a guy and. when I get horny, I need cock and I don’t take no for an answer. I had been chatting with a guy and sent him an IM asking if he was horny and wanted to have a little fun. He replied saying that he was horny as hell and wanted a nice tight ass to fuck. We cha... 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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First Date With Daddy
My Dream Date. It hasn't happened yet, but a girl can hope, this story is very short story based on my fantasy's. It was Sunday night and I had my first date lined up with daddy. We hadn't met, but we had spoken online at depth and exchanged numbers. I had sent him a couple of pic... Read full Story
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How I Met Alyssa
I groaned as the sun was shining onto my face. I turned around so I could get some more sleep, but I saw it was 9:22 am and I decided it was time to get up. I got out of bed and went to the bathroom of my little apartment to freshen up a bit. I looked at myself in the mirror and saw a 20 year o... Read full Story
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Husband and wife used by Mr. Big Black Cock
We had decided to take a trip to Vegas and spend some alone time together.. We started off with dinner, then went to hit the tables.. My husband was on a winning streak. He was up at least $1500. I whispered into his ear have fun I'll be in that cute little shop. ok? Then his luck ran out.. and befo... Read full Story
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Ride of My Life
As a student at college I wanted a bicycle for Christmas. I hadn't past my driving test and even if I had, I couldn't afford to run one with my Saturday job wages. My parents didn't have much money so I didn't ask for an expensive model by name, anything would do. I didn't think they could go far wr... Read full Story
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My amazing date with Miranda M.
I arrived a few minutes early. I'll admit it, I was extremely nervous. I gathered my confidence and knocked on the door. In a minute or so, The door opened and she was standing there, My Goddess! "You look amazing Miranda" I said. She smiled and thanked me as she invited me in ... 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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Fuck Talk with Melanie Jackson (A talk show transcripy)
THIS IS AN ORIGINAL TRANSCRIPT OF THE PROGRAM “FUCK TALK W/ MELANIE JACKSON” DATED MARCH 10TH 20__ MUSIC CUES ANNOUNCER: Hey everybody! Welcome to “Fuck Talk” with Melanie Jackson”! The show that talks about, you guessed it! FUCKING! Any kind of fucking! Straight fucking! Gay fucking! Any kin... Read full Story
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Valentine's Day Hot Encounter
On a beautiful, cold Saturday morning in Connecticut, I woke up tired and in a bad mood. I cleaned my room, fed the dog, and decided to take him for a walk to go to the store to get some smokes. As I walked, I was thinking to myself "Fuck. No Valentine's Date for me this year." I could ... Read full Story
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Salacious Sarah
Joe Dodge walked down bustling Market Street in Philadelphia in awe. Joe and his wife Tammy moved here 4 months ago from a small town in Alabama. The 24 year old man missed his hometown but at the same time he marveled at the sights in the big city. It was Friday evening, he always went straight hom... Read full Story
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Salacious Sarah
Joe Dodge walked down bustling Market Street in Philadelphia in awe. Joe and his wife Tammy moved here 4 months ago from a small town in Alabama. The 24 year old man missed his hometown but at the same time he marveled at the sights in the big city. It was Friday evening, he always went straight hom... Read full Story
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My First Sissy Meet Up
I had posted an add on craigslist asking people to let me suck them off at my place. After sorting out all the answers that I got I found a guy, John, that was incredibly eager, we agreed a time and date. The day came and I woke up so nervously. But I was determined to not let it show so I got... Read full Story
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Regina's scary, and sexy Blind Date
I had just finished doing my makeup, finally deciding which blush to use, and I thought I had some time for my meditation. However, Mr. Cobb was early. The gold minidress I wore showed enough legs, ass and tits to make any man horny, and the strappy tanned five-inch sandals, made me feel majestic ... Read full Story
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T-Girl Rodeo
Howdy folks, we would like to welcome y'all to the finals for the 10th Annual T-girl Rodeo! Now this here being the tenth anniversary and all we're gonna put on one hellva show for ya! Commentating up here in the announcers box with me is the first ever T-girl Grand Champion, Lorna "Tail Buster... Read full Story
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Becoming Her Bitch Chapter 2
I can feel the toe of her high heels sliding under my balls. I'm on all fours positioned right over it. The big black cock is lubed up and pressing against my back door. I try to relax. I try to let it in without clenching up. It'll hurt if I clench before he's in all the way. "Don't worry a... 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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Birthday Surprise
My girlfriend and I have the same fetishes and interests for the most part. We both find latex irresistible. We love the site of a tranny with a big cock. Robbie knew everything about me. For my birthday she went well out of her way to make me happy. The date rolled around. I figured it was jus... Read full Story
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Taken Chapter 1
Georgia pulled her Mercedes out of the gas station in Albuquerque back onto interstate 40 heading east. It was a long drive ahead to Chicago. She hated traveling alone, that was for sure, but the move to the office back east made it necessary. It was either drive there or sell her Mercedes and buy a... Read full Story
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Riverbank Tranny Fucktoy
Hello to all of you that read my first true story about outdoor sex. This is another account of a meeting I had in the middle of a city near a river. It was late one summers evening when I met up with this sexy young Portugese stud I had been messaging on a gay dogging site. I had been chattin... Read full Story
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Francine Hung Shemale
This is the story of "Francine" a Transgender woman from California. She and Jonathan meet in a Tucson resort two weeks after their first weekend together. Note from Francine-Thank you Mrstanley for writing and submitting my story. In real life I live and work in California and Mexico as ... Read full Story
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My First Sex with Tgirl
This is story about me......Hope you all enjoy it I was 19 years old and itching to have sex like every normal teenager. Years of jerking off to porn had only expanded my imagination and made me want to fuck a girl even more. I was turned on by just about anything and everything except gay porn. Ev... Read full Story
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Francine Hung Red Head Part 2
This is the second part of the story of "Francine" a Transgender woman from California. She and Jonathan meet in a Tucson resort two weeks after their first weekend together. Note from Francine-Thank you Mrstanley for writing and submitting my story. In real life I live and work in Cali... 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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Shemale Ride Along Part 1
I'm going go ahead and get this out of the way. During my freshman year of college, I was confused about my sexuality. It sounds strange saying this right after calling myself confused, but I loved girls. I really did. I loved all of their shapes and curves. I loved tits, pussy and ass. Now... Read full Story
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Fooled Into Love by a Beautiful Transexual
A fictional, steamy love story about a Man’s first experience with a Shemale... a real take charge kinda girl! Maria Lopez was an absolutely stunning 23 yr old Puerto Rican Goddess. I remember the first time I laid eyes on her, bent over inside her hatchback Toyota, pulling out a hanging fern pla... Read full Story
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Melissa
I'm a Japanese in my early forties living in Japan and I met Melissa online about a year and a half ago when looking for someone to chat. She is a black, 6 feet 2 inches tall, around 160 pounds and therefore a slim and beautiful transgender girl in her mid twenties. From Brazil, she is very friendl... Read full Story
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Hung Shemale has Motorcycle Trouble near Vegas
I drive down a deserted two- lane highway outside of Las Vegas, Nevada. It is August and the temperature is well over 100 degrees. In the distance, I see a tall beautiful mature creature that walks alongside the road. As I pull over, I am stunned by her powerful physique. She sports an incredibly ti... 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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Hot for Teacher
Jack was enjoying his going away celebration, as he prepared to move from teaching high school to college. He had spoken with many of his former students, and found it endearing that so many of them cared enough to show up at the party. By the end of the evening, though, there was still one young wo... 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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DISCOVERING BLACK COCK
To the greater Boston general public it was simply a small little known quite private night club located in the back part of Roxbury called The Black Rooster Bar. While in local Gay Community circles, insiders called this private by membership only pub, THE BLACK COCK CASTLE! When first learning... Read full Story
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My first Shemale
“Curious? Bi?” Well, yes, but only with a shemale. Beyond that I’m a firmly planted heterosexual. For many years I longed to have sex with a shemale but never did anything about it. (I’m not much of an initiator). The community I live in has lots of shemale beauts; maybe that started my intere... Read full Story
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Jennifer
WhiskeyIsGood I woke with a start, startled by a loud banging sound from downstairs. The floor shook from the vibrations, causing me to sit upright in my bed and glance towards my bedroom door. What in the hell, was going on down there? My question was quickly answered, by another loud bang, foll... Read full Story
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Hung Trans Lesbians Fuck Two Ladyboys
Note 1: If you like Transsexuals, Trans Lesbians, Asian Ladyboys, Big Cocks, Extreme Cock Sucking, Anal Fucking, Anal Fisting, Semen Swallowing, Role Play, Orgies, BDSM, Cock Sounding and Foot Fetish this story is for you. Note 2: All the characters are over 21. The names are fictitious, but some... Read full Story
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The Seductive Seed of a Tranny MILF
The Seductive Seed of a Tranny MILF SugarandSalt Jackson got home and immediately curled up in bed. He didn't want to move for the rest of the weekend. He'd finally worked up the courage to ask a co-worker out at work. She politely rejected the invitation. Then later on in the day, Jackson spo... Read full Story
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Meeting Amanda
I’m a happily married man. My wife Tess and I have been together since we were teenagers. We were each other’s first real lovers and being in our mid-thirties by now, we still madly in love with each other. Tess and I always are very honest and open to each other. Both in normal life and sexual... Read full Story
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"SISSIFIED": 12 JOURS DE SISSY-MAS
JOUR 1: mardi 25 C'était le matin de Noël quand j'ai entendu frapper à ma porte, ce qui était, bien sûr, très étrange à dix heures du matin. À midi, j'allais chez ma famille pour Noël, et j'avais rarement des visiteurs inattendus. Toujours dans ma robe, je me dirigeai vers la porte et fus s... Read full Story
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RÉVEIL SEXUEL SISSY ⚧️ ⚧️
Si ses histoires étaient vraies, non seulement beaucoup d'hommes ont eu des réveils sexuels entre la fin de la trentaine et le début de la cinquantaine, mais beaucoup d'hommes de mon âge étaient curieux de se féminiser, de sucer des bites et peut-être même d'avoir des fesses. Mais je ne peux pas ... Read full Story
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Dating all whole my life
Julia and Ilya, together 10 years It was more than 10 years and 2 children ago. In December 2005, we agreed to meet at the gate of my office after a working day. I did not go out godlessly for a long time (40 minutes from the appointed time), but he still waited. I hope he does not regret it ... Read full Story
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Amber
The summer after high school I moved into this cheap hotel downtown. I'd been working in the mailroom for a large company, and really needed to get my own place, but I didn't have much money. I also wanted to have more time to play dress up. It was an old building that had seen better days. I ha... Read full Story
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