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All Right I'll Do It
"Alright I'll do it but you promise you will never tell or bring this up again?" It was spring of 1970 and I had just turned eighteen a week earlier. My last year at Reidel High, located in a small northwestern town Nowhere USA with a Population of 2,700 and far away from the anywhere e... Read full Story
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Anastasia's Life So Far
Chapter 1: Humbling Beginnings My story starts where most every crossdresser's story starts. It starts somewhere around the time I was an infant. I can remember not to mention being told several thousand times that my choice of toys as a child was dolls, strollers, dress up and tea parties, Barbi... Read full Story
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My first time as a Femboy CD
My name is Nick aka. Nicole. I am a 20 year old gay femboy crossdresser and this is a little story of how I started dressing to become Nicole and my first sexual experience besides masturbation. I grew up living in an apartment complex with my mother and sister, who was 2 years older than me. M... Read full Story
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How I became a cute femboy CD
Chapter 1 Hello, my name is Natalie…well that’s what I named myself when I dress. Before I get started with my story about myself and when and why I started dressing and my first sexual encounters, I would like to give what I hope will be a brief rundown of myself. As I mentioned my name is Na... Read full Story
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I got anal creampied at the beach!
As soon as we got onto shore, I knew it was the perfect place. The hot sun was beating down on us and my body was tense with anticipation. Finally, we were going to be alone out in the wilderness with nobody around and could enjoy each other thoroughly. My hunky date and his monster cock were going ... Read full Story
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DATES NUITS
My wife, Denise, and I have been happily married for over 10 years. Over the years, we have enjoyed a vibrant and adventurous sex life. As we've grown in our marriage, we have become very open and honest about our sexual fantasies and desires. Through the years, we have come to realize that my w... Read full Story
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I Fooled Everyone But the Black Pimp Part 4
Fuck. I said I wasn’t going to do any drugs and I’m drinking this Gatorade that I know has something in it. Trish said it would help my nerves, and it has, I feel loose…and very horny. When I’m usually horny my cock is hard but right now, I’m putting lotion on my body and I’m going really slow over ... Read full Story
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Aunt Susie's Training Part 5
Aunt Susie and I woke up around 1030AM and Aunt Susie said we need to get ready for a surprise appointment in the city. We put on our make up, I pulled a ponytail again and we got dressed in jeans and heels and matching white button down shirts which we left untucked. We drove first to Aunt Susi... Read full Story
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My Noisy Upstairs Neighbors Part 2
In my previous post, "My Noisy Upstairs Neighbors," I shared the story of how I finally confronted my upstairs neighbors about the constant noise they were making. However, this encounter took a devastating turn, leading to a traumatic and deeply violating experience, when they raped me and filmed i... Read full Story
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Growing up CD
Peter, Max and I played together like that for the rest of the weekend. We must have sucked each other's cocks at least 10 times over the three days. Peter and I were both physically drained. Max just seemed to be insatiable for our bodies. He didn't want us to go. He kept on saying how much he ... Read full Story
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Debbie Part 1
He had gotten a job with a large company doing odd jobs, mostly filing papers and bringing out mail. It wasn't much, but it was enough to pay for a small one-room apartment on the seedier side of town. Since he was still very shy from his experiences in high school he hadn't made any friends yet, bu... Read full Story
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Debbie Part 2
There were no clocks and no windows in the dungeon, so Debbie (as she thought of herself after a long night of pain, lust and confused thoughts) couldn't really tell that it was morning. But she assumed it was morning when Mistress came back. Debbie's walk was still perfect even after walking around... Read full Story
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Turning my neighbour on in pantyhose Part 2
So.....there I was. Lucy...dressed up to the nines, crossed legged on the window sill. The guy next door, rock hard, almost licking his lips! I was sooooo turned on. I knew I looked fab today! Big headed? Sometimes you just know dont you? You are about to get to know me better.... Was it wrong to... Read full Story
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The Trip
I’d been seeing Joe for most of the summer and in that time I had starred in maybe a dozen or so of his private home movies. My hair had grown maybe another inch, I’d had my ears pierced and my eyebrows shaped, as far as my parents were aware it was because of a drama club I’d join... Read full Story
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Click, click, click....
Click, click, click…the sound of high heels contacting a hard surface has always attracted and aroused me. Whether it’s on tile floors in a hallway, the concrete of a parking ramp or the asphalt of a mall lot, I turn in anticipation to drink in some pleasing eye candy. How short will th... Read full Story
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Body Image
"Sit down Mona. We have to talk." He had heard those two tiny sentences more than a few times in the last several weeks. Every time he did he felt a strange queasiness in the pit of his stomach. Yet no matter how hard he tried, he could not refuse. He walked over to the couch across fro... Read full Story
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Fifties Housewife After the Party
I had not fallen asleep after Darren had, exhausted, after the party and the incredible lovemaking we had shared. I just couldn't come down from the high and emotions of the whole direction we had taken. I was lying spooned against him, his warm cock nestled warmly against my ass. My nightgown seeme... Read full Story
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Becoming Alanna Part 3
We went up stairs to the kitchen and she had me start to help her ice down beer and get bottles of booze out and open. There was a large bar but I noticed not much in the way of food. I helped tidy and set up cups and get ice and then with a sudden shock to my heart the doorbell rang. As it did I ca... Read full Story
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Your Waitresses
You begin your evening by taking a long luxurious bubble bath followed by taking the time to apply your makeup at a beautiful white makeup table and mirror from the 1920's. You then slide a sheer pair of black stockings up each leg and attach them to your black and red lace garter belt. You then run... Read full Story
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The war in my mind
"I found that I wake up at night to watch sissy hypnosis. I think I'm addicted and more than I look, the more I become a real cumslut. Everywhere I look, I see guys and I secretly beg to get ass pounded". Started to deal with my sissy around 16-17. At this time I didn't know a... Read full Story
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How I Became the Sissy Slut
It all started when I was about 11. I was a very petite and short and had long straight brown hair with whispy bangs as a child. I was often mistaken for a girl. I have a sister who was 6 years older than me about my size she used to dress pretty sexy with the tight jeans and the skin tight sailor b... Read full Story
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The Coma Girl Brain Transplant
[This frivolous story is something I put together as an entry for a comedy competition earlier this year, not to be taken at all seriously, a bit more sci-fi than erotica, more of a mind-fuck than anything else so it’s not jerk-off material but hopefully some of you might still enjoy it] Thankful... Read full Story
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Sissify Your Boyfriend Manual - transation
original= manual-sissificar-a-tu-novio-4979 Used google translate, found some pronoun/object/context issues, and I believe ladybug = ladyboy Sissify Your Boyfriend Manual MANUAL FOR WIFE/GIRLFRIEND TO SISSIFY YOUR MAN, DISCOVER HIS SUBMISSIVE SIDE AND TURN HIM INTO ?HORNAND? AN... 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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Headmistress' Favorite Sport Part 11
Denise lay in the trunk of the car, her legs tied together with rubber straps waiting patiently to see what would become of her. She had long since relinquished all control over her own life and knowing that she was just useless sissy-slut made it easy to accept that whatever was done to her was pro... Read full Story
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Debbie Part 9
It soon turned out that Debbie wasn't destined to spend the rest of her life as a whore. As she returned to the apartment one night one of Mistress' men was waiting for her. She had only just opened the door, when without a word he cuffed her hands behind her back, gagged her and put a collar and le... Read full Story
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Debbie Part 10
Debbie might have lived out the rest of her life if it hadn't been for some events, which started back at Mistress' mansion. Several years after selling Debbie, Mistress Helen Chamberlain still ran her ruthless slaving operation. Giselle was still her favorite slave, constantly restrained and regula... Read full Story
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Transvestite in trouble Part 5
After feeding me Mary, untied me from the chair, other than keeping my hands tied behind my back, and a short chain between my ankles. She attached a studded collar around my neck attached to a dogs lead, and led me from the room. I teetered on the heels behind her, taking little fairy steps due to ... Read full Story
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Taken and in Public Part 3
I tried to go to sleep but was just so horny; I wanted to dress up again; I wanted to go out; I wanted to be fucked! All these emotions were running thru my head and I just lay there. My mom told me she would be starting the 7pm to 7am shift at the hospital for some time and thought I should get... Read full Story
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My Mistress, My Slave
I first met Robert as I was moving into my new apartment building. He was just one of the several men who appeared out of the thin air and offered to carry my furniture and boxes up to my new second story apartment. Most of these manly he-men only appeared because they wanted to get to "know&qu... Read full Story
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Special Shemale Fun
Everyone in the hallway jumped slightly, turned and quickly looked at the tall girl near the sound of the slamming locker. Satisfied that there was no crisis at hand, the kids at the school mostly went about their business. Of course, there were the few admirers that glanced at the girl at the locke... Read full Story
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My step mom turned me into a sissy slut for dad
When I was in High school I would spend the summers with my dad and step mom. She was so hot and always dressed sexy, They were always very playful about sex, not like my mom and step dad. I loved the atmosphere. During the week they would work all day and I would have the place to myself. I would ... Read full Story
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The Dinner Guest
After meeting John, and immediately becoming his lover on my first-ever dressed meeting with another person, our relationship became a deeply satisfying, regular thing. I guess I became his “girlfriend” although some might see it more as his “wife”. We met at least twice a we... Read full Story
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PantyBoy Gets A Reaming
I love to get really in touch with my feminine side. I get so turned on when I watch a man look my body up and down while I'm wearing some really sexy lingerie. I feel so naughty and slutty, knowing that I am going to let him do anything and everything he wants to me!! I was chatting in a room on on... Read full Story
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Danielle's First Meeting
Daniel stood on the front porch and waited for his date to arrive. Well, Daniel at this particular time was actually Danielle. You see, Daniel was a crossdresser. Danielle was his female alter ego. He was 37 years old, medium build, average you might say and stood 5-feet-10-inches tall, weighing in ... Read full Story
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Darling Nikki
Chapter 1 - The Setup "I'm going to catch him!" Samantha thought to herself as she looked at her disheveled panty drawer. She now had proof that her roommate, Nick, had been wearing her clothes, but had to catch him in the act. She did a search online for ideas on how to catch him. She ... Read full Story
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Young Crossdress, Meets His Daddy
Well I am 28 year old male, not in best of shape. I can still run a mile in under 15 minutes, and I work 3 to 4 times a week. I try to stay in shape a little bit. Well that is enough about my physical appearance. I am also married to very beautiful wife, who I love more then the world. We have very ... Read full Story
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Uncles Lessons
In '91' during my senior year of high school my folks split up. The whole thing was a mess, with me being sent off to relatives while my mom took my younger siblings to the gulf coast to stay with her parents. They sold the house and Dad moved to be with his new future 'ex-wife' outside of Dallas. ... 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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Anastasia's Life
Chapter 1: Humbling Beginnings My story starts where most every crossdresser's story starts. It starts somewhere around the time I was an infant. I can remember, not to mention being told several thousand times that my choice of toys as a child was dolls, strollers, dress up and tea parties, Barb... Read full Story
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Angel Chapter 6
This is an entry in the Literotica Winter Holiday Contest, and is part of an ongoing series on the life of Angel Jones, a beautiful young T-girl in London. For more detailed information on her and on the other characters who appear in this story, please see previous episodes. Angel Jones was uns... Read full Story
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My BBC Friend
I was back in Indianapolis this past week. I had not had a good fucking for some time and was hoping to hook up with my friend Terry.I had hooked up with Terry several times when I was in town. He has an amazing cock. he can fuck for hours and loves to make love to his sissy slut. I got to the hote... Read full Story
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Lady In The House Ch. 02
A story by Michele Nylons, Part II "She's all yours Eddie. She looks beautiful." I heard Carmel say as 'she' disappeared down the corridor, her high heels clicking on the tiled floor. Eddie appeared at the door to the cell, he stepped inside and closed the door behind him. "So what do yo... Read full Story
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Lady In The House Ch. 09
A story by MicheleNylons ( Continued adventures of a cross-dressed prison prostitute. ) I lay there stunned, how had I miscalculated my effect on the Warden? The one man who could guarantee a transfer from this shit-hole; fuck!!!! The cravings of male sexual hunger within the confines of the ... Read full Story
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The Day I Went SheCock Crazy
I summed up courage to meet up with my old shemale flame Fransicca (she is a Malaysian but living in indonesia) ... messaged her, she sounded excited and asked if i minded her friend joining us. 'Why not' i said. It was settled. we booked a villa for the next day. I checked in early. cleaned up ... Read full Story
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Camming Down the Rabbit Hole Ch. 07
Opening my eyes I struggled a little as the residual cum on my face from last night’s show hadn’t been fully wiped off, I felt the dry and crusty leftovers crinkle on my skin, but couldn’t help but smile to myself as I remembered how it had got there. The intensity of that orgasm had been on another... Read full Story
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Santa & Mrs. Claus
In my story called "Santa Likes Fembois" here I explained that I discovered that last Christmas when Santa Claus visited my house then made me suck on his cock before fucking my boypussy. He also gave me an actual present: a winning lottery ticket. Well, with that multi-million dollar winning ticket... Read full Story
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In Need of Some Sex
In Need of Some Sex By Sabrina G. Langton *** Author's Note: Hi... Just a teensy tiny story. I'm sure you know what I, um, well we like. Just a little sex in the night to make the heart grow fonder. Just two people meeting for the first time, definitely not the last. A nice intro to a new rel... Read full Story
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Angel & Victoria
Angel was a beautiful young girl living with two of her best friends, Monica and Amanda. All were transsexual, and the three shared everything together, from clothes, their sexy intimates, lovers, and each other's bodies. Angel was the youngest, at 23, a Japanese anime lover and the most... Read full Story
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Mistress Jasmine made me a slave forever
I should have been honest. I mean I should have known that lies have short legs and now they had caught up with me. The worst was I had not only lost my place in my bed but had also lost my place with my wife. Somebody else occupied these places now. Let me tell you how everything went. More ... Read full Story
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Jamie is taken Part 2
Jamie came to on the cold dungeon floor retching and coughing, his mind paralyzed by a mixture of pleasure and panic. He had loved the orgasm he had just experienced. His experience with breathplay was less than half a day old and already he knew that he loved it almost as much as finally ... Read full Story
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Sissy lola gets a treat
Last night was my first night as a sissy maid for my beautiful goddess maureen and i have been instructed to tell you what a dirty little cock sucking whore i have been. I have known goddess maureen for a while now, she has been giving me instructions via webcam. She would make me flog myself or ... Read full Story
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Catching Up
It was with mixed emotions that I listened to the message on my voice mail. It was the familiar sound of Mark, a long time friend whose call I had missed earlier that afternoon. Now as I heard it, for the third time, I felt my stomach slowly relax from the uneasy twist that had taken hold the minute... Read full Story
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Been Caught Cheating Chapter 3
I awoke in pain. I had slept bound all night. And it also seemed that I had been hit with something to wake me up. Angela was standing over me with one hand on her hip and the other holding my bounds that I slept in. She was already dressed and ready to go. I looked around to make sure we were alone... Read full Story
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On the Run
“Your first mistake was stealing hundreds of thousands of dollars from me. Your second mistake was thinking you could get away with it.” As I stood trembling before his desk, Mr. Atwater regarded me as if I were a bug on the windshield of his Lexus. “Do you have anything to say for... 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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