Free Stories

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ACROSS THE STREET AND TWO DOORS DOWN by Spanky de Bautumn
Jamie knew he was different. He didn’t fit in with the other boys, but he didn’t feel like he fit in with the girls either, he just knew he was different. He wasn’t into dolls or balls. He was the smallest boy in his class and more than half the girls outweighed him. But the one thing he had going f... Read full Story
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Panty Town
Chapter One -- Jamie Jamie Sanders did not think he was a sissy. Growing up, he played with trucks and showed his innate male aggression though soldiers games with the other boys. He climbed trees and watched baseball with his Dad and brother. Unfortunately, by the time he was in eighth grad... Read full Story
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Aunt Cindy's Bizarre World
My name was Jim Rogers Jr. at one time. I was born and raised in a small town in a rural county in Oklahoma. My father James had been the pastor of the local Pentecostal Assembly of Jesus. Dad was what was known an ultra conservative hell fire and brimstone preacher. My mother's name was Allison. Sh... Read full Story
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Emily and Steve Part 8
I didn't even see it coming. I should have. I should have known that life just can't work out exactly like you would expect. Instead it has to throw you curve balls, put you back on your heels, and then put the next one on your chin. The first few months after Emily moved in, things were going gr... Read full Story
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MILF Alessia Travestita finds a bottom boy
I was several days into a cruise to New Zealand and Australia with my wife. This morning my wife went on an excursion that I had no interest in, so I had the cabin to myself. I hadn't had any sex with my wife in the last 3 days due to the activities such as the various jaunts to Auckland and the sur... Read full Story
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Marcia Goes Back to School
Marcia was painfully nervous. She hadn't been able to eat very much in days. The upside was she was even skinnier which would make Mistress and her husband very happy. She'd always been thin and on the diet Mistress Carol had her on she was already thinner than she dreamed possible. Her anxious stom... Read full Story
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Rebecca's Secret Part 2
-5- Rebecca lay in my arms, trembling after the most incredibly orgasm she’d ever experienced. Hell, it was the most incredible orgasm I’d ever experienced and I wasn’t even the one who’d had it! We held one another in the darkness, myself stripped of every article of clot... 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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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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Groped on the Bus!
In real life I do not crossdress in public, I am not yet comfortable being my true transgirl self, I wear normal men's clothes and I look like a guy. So I look very different from my persona here. So...there I was standing among dozens of strangers at a bus stop. I kept looking up from my phone ... Read full Story
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Masturbation fantasies: Amanda, queen of the peep show
A guy visits a peep show with unexpected results. As he gets to watch a girl with something special, he discovers his hidden desires. This story contains: peep show – voyeur – gloryhole - fake tits – group masturbation – male masturbation – shemale – frottage - titfucking When William finall... Read full Story
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Exposure, Disclosure
The Greatest Liar, Exposure, Disclosure © Alexandra Rios 2019 Author’s Note: This is a continuation of the narrative which commenced with “My Awkward Phase”, which I posted here previously. Readers may wish to read that before continuing, although I have written them to stand alone. Natives s... Read full Story
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A Shell of A Man
Six years ago, I was doing well enough to finally afford my dream apartment. It was a studio apartment on the upper side of town. So, I had the job, the apartment, the money... but I was lonely. Very lonely and very horny. Not only would I get all hot and bothered from looking at all of the pretty w... 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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Big Dick Alessia Visits Dallas
Alessia Hung Mature MILF travels to visit a Big Dicked Man and his Sexy Household If you like Transexuals, big cocks, bondage, BBWs, big clits, deep throat, fisting, 69, ass fucking, sounding, piercing, cum swallowing and big loads this story is for you. If not don't bother reading. If you fav... Read full Story
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Daddies New Girlfriend
Doug suspected his 19 year-old son Jerry was stealing money. Doug worked far too much trying to provide for his son to supervise him properly but drew the line at theft. So he decided to set up a web-cam behind the mirror in his bedroom, he'd used the very same 2 way mirror to film his dead wife Cyn... Read full Story
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Hard Decisions by Elaine © 2020
Hard Decisions by Elaine © 2020 No one in this story is based on anyone alive or dead. It is a work of fiction and should not be read by minors. I appreciate the kind efforts of many of my friends who cast a welcoming glance over the initial writings. I owe you all a big debt of thanks. Prolog... 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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Elaine & Me
- Chapter One – Our First Meeting - I had two weeks to go before the final degree exams and I was working hard. Perhaps too hard, because I desperately needed a break from the hours and hours of revision. It felt like I just couldn't take in any more detail about Quantum Mechanics or Solid ... Read full Story
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Young Sissy Chapter 1
I don't know how long I was under...days, weeks...who knows, maybe even months. Reality blurred with nightmares as I felt my flesh being cut into by cold scalpels and stuck with needles, filling me with horribly persuasive dreams of a beautiful new body. I tried to imagine myself as a man, just to s... 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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ROBERTO’S SECRET by Spanky De Bautumn
Cody Daniels was only trying to help her country; she never dreamed things would come to this. She was patriotic and felt compelled to do whatever asked of her to aid in the capture of the terrorist known only as "Roberto". But lying in his bed, bound and gagged, Cody wondered why she let herself go... Read full Story
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A Certain Perception
Kyra was not the girl of my dreams. I never DARED dream a woman that good would just walk into my life. She was smart, sassy, vivacious, intuitive, resourceful, and a real 'people person'. We met in an Internet chat room called "Working Girls". We're not talking about the kind you find in ... Read full Story
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Nylon teasers
They came into the video store where I worked as a clerk. Almost every day. Teasers. Both of them. What made it both great and terrible for me was that it fed my deepest fetish -- stockings -- as it denied me any fulfillment other than frequent and frantic "self-gratification."... Read full Story
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Sabbatical or Continuous Gang Bang?
My twin sister Laura had already left to go back to college this fall season, but I had decided to take off a semester as I was totally burnt out on school and needed a break. We were twins but not identical though we did look a lot alike and roughly the same size me being a few inches taller. My... Read full Story
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Headmistress' Favorite Sport Part 10
When Denise came to she was lying in bed. She had been washed and she could no longer feel the annoying diaper rash. In fact she felt fine, clean and well rested. On her feet were what turned out to be black Oxfords with seven-inch heels. Her ankles were in steel cuffs and connected by a eight-inch ... Read full Story
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Cab Driver
I already have a raging hard on, and it is only 9pm. I have my clothes for the evening laid out on the bed before me, and my cock, balls and ass are newly shaved. I have decided to wear all black tonight: black lacy panties, bra and suspender belt, sheer black stockings, and a tight black dress that... Read full Story
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MILF Alessia Travestita finds a bottom boy pt 2
Several days ago, Alessia a beautiful Transsexual with a huge cock seduced Stan on their cruise ship. He willingly and enthusiastically sucked her cock and gave her his ass. She brutally throat fucked his mouth before pounding his ass. They spent over two hours together until they were interrupted b... Read full Story
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Ambers torment
It seem to be the typical day for Amber as she entered the home of Master. The usual early wake up and long drive down to his house seemed nearly routine though, the last visit was a few months past and the girl was anxious for what was to come. Although, her expectations were not different from any... Read full Story
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Birthday Present
Chapter 1 "What would you like for your birthday?" my wife asked. "An unforgettable sex session" I answered, jesting. "Is that right? Well, we'll see" came the reply. I forgot all about the exchange and nothing else was said about my birthday. The day arrive... Read full Story
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Filthy Little Beast
I had very few memories of my early childhood. The ones I did have were anything but pleasant. I did remember my mother and her blind hatred of my father and myself. She was very tall blonde woman with cold blue eyes named Monica. My mother always dressed in the most expensive leathers and satins in... Read full Story
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Feminized By My Mother
Hello. My name is Dan. I'm doing okay, you? I see. Well if you are going to be listening to my thoughts please keep the volume down, I am trying to think. Some things are going on that have got me very mixed up and I have to concentrate. Like most overly complicated things in life, a woman is inv... Read full Story
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Dressed for Disaster
After a last look at himself in the full-length mirror on the closet door, Pat put his magnetic key in his purse and left his hotel room. He had done this enough times to be almost calm as he waited for the elevator. When the door opened, he was relieved to be greeted by an empty lift. It always ... Read full Story
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Chinese Extremes Part 3
It was time to leave Mistress Ming's house and Lien was dressed, or rather tied up, by the two little sissies. First a brutal corset was fitted around Lien's waist, followed by a broad, black leather collar. Lien's hands were then tied in an armbinder, a black leather sack that held Lien's arms behi... Read full Story
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Teacher Student Confidentiality
It was raining cats and dogs outside as Ms. Catherine Walker (Cat by her friends) graded her Accelerated Integrated Geometry test scores. Her was long and flowing and her sweater was purposely pulled low to embarrass the male teachers with her cleavage. Her cock twitched as she shifted her leg to a ... 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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Bimbo Bombshell - Chapters 1-2-3
Bimbo Bombshell - Chapter One: Singled Out! Even though it was Friday, the bar wasn't particularly crowded that night. I never knew what hit me. This Gorgeous Blonde bombshell, starts flirting with me right a my table. I found myself wondering why this glamorous beauty, had chosen me. I was... Read full Story
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Kayla and Tracy: The Layover
Kayla and Tracy strode across the marble-floored lobby, their heels clicking across, and suitcase wheels rolling across, in rhythm as they walked up to the desk. They seemed incredibly out of place in the relatively quiet hotel room. Kayla, of course, always stood out, especially when platform heels... Read full Story
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Candy Pink Part 2
Chapter 4 My parents had a letter shortly after from the headmaster Mr. James Allen. I was to head out to CA before the start of winter term to get settled into the dorms and go through orientation. The letter said I should be there no later than December 1st and that they would arrange for me to... Read full Story
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Daniel, Dani, Dana
After an hour of some hot steamy role playing online I got up from my computer. This newest and best chat friend ever was helping me enjoy this private time more than ever. My feminine alter ego seemed to flourish and delight when I spent time with him in chat. Wearing a little more risque under thi... Read full Story
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Female For A Day?
I have always been obsessed with boobs. I like them all but especially big ones. I stare at them in the grocery store and of course have an extensive collection of pics from the internet. Lately, I have even been thinking about what it would be like to have a big set myself. I'm a guy don't get me w... Read full Story
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Brotherly Love, Sisterly Love Chapter 2
"RACHEL" My twin sister, and sometime brother, and I had been experimenting sexually with each other and crossdressing together for around a month, growing to love and to perfect our new feminine personas until they became the ones we thought of as our true selves. Whenever our parents ... Read full Story
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A Helping Hand
It was late on a Friday night when I heard my parents arguing. It always happened whenever they were getting ready to throw a big party. My mother played the role of party planner and handled all of the details, but between caterers, musicians, and the other help something always went haywire. My fa... Read full Story
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Cross-dresser Drinks Cum
Nikki looked up at me with her big, brown eyes as her head bobbed on my cock. Nothing was quite so sweet as one of her blow jobs. She had this way of dragging her tongue along the underside of my cock that made me want to cum in seconds. I always tried to hold it, but Nikki wouldn't let me. When she... Read full Story
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Blame Abba Chapter 2
Part 4 Out alone I wanted something which would let me wear my black 4 inch leather stilettos with ankle straps, really sexy shoes, my very first pair of TV heels. I opened the wardrobe to get them out, then started choosing; black seamed stockings; a black thong; my waist cincher bustier; my sho... Read full Story
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Blossoming Shemale
My name was James. It was, before everything that happened, anyway. I'd come from pretty good stock, as the snooty, upper class would likely say. I guess I still did, although it would take a DNA test to prove it now, and to be honest, I didn't really have the desire. That was all before. I have to ... Read full Story
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Pleasantly Surprised
It was Friday night and Robert was sitting at home alone. His roommates were both out on dates, and his girlfriend, correct that ex-girlfriend, had moved all of her things out three weeks ago. It had been one of the dullest months in his adult life; four weeks of sitting in front of the television, ... Read full Story
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Fourth Slave
I had been to this particular establishment before. I knew very well what they did and the women here were nearly all abducted. I knew that. What had brought me here today or rather on this night, was the loss of my slave. I had sold her when I got bored with her. I had a particular taste in women t... Read full Story
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The Fabulous Alessia Travestita
Alessia is a real transexual. Several of her porn videos are on this site. She collaborated with me in this story. Alessia is a natural blonde haired, brown eyed, mature fifty -five year old Transsexual woman from England. She is tall, very fit, stands 5'11," 36B-26-30 and a slender 133... Read full Story
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The Hotel Part 1
I knew when this started it would be like nothing I had ever done before. I drove up to the hotel early friday morning. I was checking in for seven days. Seven Days of non stop pounding of my asshole, Strapons, Crossdressing, fucked fem, huge dildos, and giant buttplugs are just a few of my fetishe... Read full Story
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Darla's Video Delight
The day had gone well so far with my girlfriend of the time having just left the night before, going out of state for two weeks visiting relatives. It was Saturday so I didn’t have to work, I had completed my chores... shopping, cleaning the apartment and doing laundry and had spent the aftern... Read full Story
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Kidnapped (Adult Fiction)
Kidnapped I remember being normal. I was a young man in my 20's living in my parent's house struggling to get by. I was online more than I probably should have, but it was an escape from the harsh reality of my life. I didn't feel fulfilled or like a success, I felt like a failure on many differe... Read full Story
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A Future Society
Anna was lined up with the other girls beside her, the heat from the electric torches on the wall stinging her bare backside. Her long blonde hair stretched down to the top of her ass, shielding her back from the heat, but she often wondered during line ups whether or not a bulb would burst and send... Read full Story
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A Game within a Game Part 1
Epilogue Rob came home from work. His wife Jenny was waiting for him. In her hands she held a letter. Jenny said: "We received this letter today. It is sad news from Marion S. We have met her and her husband John a few times - do you remember? John has had a car accident while driving fas... Read full Story
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Fender Bender Chapter 2
The bright sun shining through the window woke me up, for a moment I was confused and disoriented. Then it all came back to me. I had sex with Mark and Susan James last night and I was still wearing a pink baby doll nighty and matching panties she had given me to put on before we went to bed. I w... Read full Story
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My Brother's Panties
My brother and I are twins, fraternal not identical. Throughout our lives, no one ever confused us, and furthermore, no one ever thought we were siblings. Growing up I would often get the question, "Kevin, why do you hang out with Jamie so much?" People were always surprised when they lear... Read full Story