Free Stories

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The Making of A Sissy Part 12
Bella tried not to look too downhearted as Sandy dropped the pretty sissy back at her Aunt Jane’s. She told her to keep her chin up, keep the phone well hidden and use it to call her whenever she liked, regardless of what time it was. Her aunt smiled wickedly at the now primly dressed sissy as... Read full Story
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The Making of A Sissy Part 8
The girls sat cross legged sipping orange juice as the day warmed up around them. Roberts’ house had extensive lush lawns beyond the pool which shimmered in the hot sun; the pool looked very inviting to Bella and Roberts looked at the pretty sissy, his mouth watering as his cock pulsed. &ld... Read full Story
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HOW MY AUNT AND SISSY NEPHEW CHANGED MY LIFE FOREVER! (fictional
It was the very first night of my month long North Carolina July summer vacation stay when my Aunt Meg suddenly entered the bedroom that I was temporarily sharing with my younger cousin Rudy. Being so openly effeminine in his body language,voice and looks, I had already planted such dirty thoughts ... Read full Story
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A Night of Makeup, Cock and Cum - froam Annamalice
It was all I could do not to accept. After all, it's been a fantasy of mine for years. When given the opportunity, I had to go for it. I had been surfing the internet for crossdressers, shemales, transvestites and transsexuals. The idea of a hot woman with a cock had always turned me on. Further, I... Read full Story
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The Making of A Sissy Part 9
As they sat sipping drinks and discussing what shots would be done indoors or out; Bella’s little cock bulged in her sari as the mature redhead licked her lips as she discussed the ways in which Bella should be trussed, collared and leashed, amongst other things. Sandy stood up suddenly and ra... Read full Story
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I and the old man's story 后面中文
I am from Chongqing, a boy who loves his father. When I was young, my neighbor aunt always said I looked like my sister, like a beautiful girl. At that time, my family was relatively poor. My Sister, my parents, and my family of four lived in public rental housing of less than 30 square meters. Star... Read full Story
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The Making of A Sissy Part 11
Whilst Bella showered, Ellen and Sandy went down to the poolside to ready some ice and bottles for drinks later; there was Bella’s phone, Ellen tapped in the number to her own phone, and also took down someone else’s number. Ellen smiled wickedly. “I have a very sweet idea, but ... Read full Story
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The Society
I met her during the summer. I was only nineteen and working to save some money for college. I had been raised by my grandparents who had both passed away over the past year. After the burial costs I was far from wealthy. My parents weren't around so I was on my own at a young age. I had moved a cou... Read full Story
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HOW ONE PEEPING TOM MORNING TURNED ME INTO A SHEMALE SISSY BITCH
It was while cutting across his back trailer park lawn around 7pm on misty July Saturday evening, when I first discovered that Mr. Parker was really a fag. How else could you describe a man wearing a long blonde wig on his head while below he wore only a large somehow stuffed pink lacey woman's bra ... Read full Story
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Sissy Femboy Chrissy in Drag at the Club
"Can you wear a dress tonight?" "I can't crossdress in public, I'm not 'out' and don't want to be seen that way." "That's okay. We're going to a gay-only club that has a drag queen show tonight, so you'd fit right in." "Cool, but I'll have to change when we get there." "Awesome! See you tonight!... Read full Story
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How I Became Chrissy the Caged Sissy
I am a sissy, or femboy, or tgurl, or shemale? Well either way I like wearing female clothes and being treated like a girl, especially in the bedroom, and now I also like being locked up in a chastity cage that I wear 24/7 now. This is the story of how I became a caged sissy: "Put it on and ... Read full Story
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Fender Bender Chapter 8
My name is Robert, but when I am dressed I call myself Vicki. I am 5'9" 160 pounds, blonde hair and blue eyes. I turned 18 a few months ago. The last two weeks of summer vacation was a wild time for me, I knew that things would settle down once school started. Gary, my best friend for years,... Read full Story
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Interracial Sissy Story
(Some prior notes about me, this story and my writings: If MALE bisexuality, crossdressing or interracial sex bother you, don't even bother reading this further, much less commenting. Many have had secret fantasies about what it would be like to be the opposite sex, during sex. Some of my influences... Read full Story
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The Making of A Sissy Part 3
Before the audience at Aunt Jane’s house, Bella cowered before the man, who gently put his hand behind her head and pressed against her soft hair as he coaxed the sweet pale complexion of her pretty face and pink lips toward his stiff and excited member. The man so wanted to slap Bella’s... 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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Karen, My School Teacher Part 4
Meeting my other teacher By FoxyHosed Next morning as I woke up, I jumped in my clothes and got myself a coffee, and went to school. I got in 15 minutes early because I didn't want to run into Karen. As I entered the door to the school, I saw some of my classmates. I thought the coast was clea... Read full Story
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A Fetish Doll For Mommy
There is a very old saying," Be careful what you wish for because you might just get it." My fathers name had been James Bradley. He had been a CEO of a top Wall Street investment firm. My father didn't climb to the top by being a good guy. He was a total prick who would stab anyone he had... 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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The Double Sex For Sissy
Jeff Malville awoke slowly, moaning softly. He almost forgot where he was in that moment where sleep and being awake clashed. However, after that split second, it all came rushing back and he moaned in delight. He was a captive on the Double D Ranch, and even though he was considered an employee... Read full Story
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Kylie and Chrissy
The following story is the first part of ‘Kylie and Chrissy’, a story documenting the blossoming sissy-hood of two teenage boys. It is partially autobiographical and partially fiction. PART 1 - THE INCIDENT ‘Stop… we really shouldn’t be doing this’ ‘It’s just a bit of fun. Now just hold sti... Read full Story
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Fender Bender Chapter 6
My name is Robert, but when I am dressed I call myself Vicki. I am 5'9" 160 pounds, blonde hair and blue eyes. I had just turned 18. Mom and Curt had been home form their vacation for almost a week and I hated it. Sure I was glad to see my Mom but with them around I had to revert back to bei... Read full Story
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Purple Kiss, part 1
It happened during a week long trip for work. By the third night in a strange city I had grown tired of the hotel bar and broke away from my work colleagues for change of scenery. I told my coworkers that I was going to bed then quickly made my escape. The night was warm so I decided to take my o... Read full Story
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Sissy Slut and Stepdads part 2
My mother kicked Frankie out and swore that he was the last loser she would ever date. She believed that we were still having sex, and she was right. Pure raw animal lust drove us, and It was even better when we sneaked and got. That nervous adrenaline mixed with my passion and made me super horny a... Read full Story
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Satan Shemale Bimbo Sissy Doll Chapter 1
At just 22 years of age Johnny was bored and disgusted with his life. He would spend his nights in satin and leather with his face made up in a long blonde wig. He would become Sindra, a creature of the night. Sindra would pull on her long black kid gloves and masturbate to photos and fetish cart... 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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Sissy Experience - Episode 1: The Beginning
Hello All, Hope you’re all doing well!! This story narrates the beginning of my crossdressing and sissy adventures. Before I begin I’ll tell you somethings about my family. We are a family of four consisting of me, mom, dad and an elder sister. I am currently 20 years old and in college. My da... Read full Story
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MY Party Favor Fantasy
My Party Favor Fantasy A fictional story built around an old fantasy of mine I ran a notice on one of those sex sites that said” Help me fulfill my fantasy and I bet we take care of some of yours also. Hi there, I am Penny and I am a total bottom trans w... 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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Sissy Slut Reunion
Rob had moved back to town and called me. He had just moved into his new place and he wanted me to come by and talk. I knew what he really wanted from the tone of his voice, because I wanted it too. He said he had been thinking and dreamed about me the whole time he was away. My spirits lifted and ... Read full Story
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SISSY RULES!!!
There are a few things a sissy must understand in order to attract, and then keep, her man. Let’s look at them, these Sissy Rules. (✿◠‿◠) 1. Men are superior to you. This is rule number one for good reason: it is a simple statement of fact. It is so important that many questions that a potent... Read full Story
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Fender Bender Chapter 3
Susan called me early Monday Morning and asked if I wanted to come over and lay out by the pool with her, she told me that Mark had a business meeting and would be gone most of the day so it would be just us girls. I remembered what happened on Saturday when we were laying by the pool and of course ... Read full Story
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bi to sissy caught and turned
It was during a Wednesday nite supper this past April when Penny my wife of seven years, suddenly looked me straight in the eyes while calling me a GAY COCKSUCKER ! Instantly while I swallowed hard and quickly looked away from her, my worse dreaded fears in life had somehow just become reality! So ... Read full Story
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Becoming a Cock Worshipper
I first realized I was bi the summer after high school. Up until then I had only been really interested in girls. Like any high school guy I watched a lot of porn and soon realized that I really liked really nasty deep throat blow job scenes. I especially enjoyed watching a girl choke and gag and... Read full Story
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A Natural Sissy Part 4
The Next Day I was up early, and called to set up a surgery for Stacy’s breast enhancement. The hormones were working but his tits seemed to have stopped growing at a B cup. I wanted him really top heavy. At least a D cup, maybe a DD. I let the exhausted sissy sleep. As I was finishing u... Read full Story
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Fantasy to Reality
I faded in and out of consciousness. My body was numb and I waded through a sea of words and images that filled my mind, struggling to focus on anything specific. Slowly I began to wake but my eyes did not open and my body remained numb. I searched for my memory, I knew it was there but I couldn'... Read full Story
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Down the Path Part 5
I force myself to walk down the corridor and to the elevators. When the door opens there is an older couple in the elevator and I get on and move to the other back corner. The man's wife is standing a little in front of him and I see him look over at me briefly. Then he looks again, giving me the on... 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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Blame it on the Wedding Dress Chapter 2
Chapter 2: Saturday After a night without much sleeping I woke up at nine in the morning. My dreams had tortured me and presented a number of scenarios of how Katie would punish me. Some of them appeared nice to me, but others gave me a lot of pain. Would she really present my mental attitude to ... Read full Story
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Sissy Slut and Stepdads
Frank was pumping me hard and his huge cock seemed to have grown and become extra hard. I am so thrilled that way he enjoys fucking my ass with such passion. I would almost think he was in love with me if this relationship wasn't so bizarrey. It’s ironic that as a male I always get total humiliation... Read full Story
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A Fairy Tale Part 1
=-=-Chapter One-=-= "Heather?" My boyfriend was knocking on the bathroom door. "What's wrong, are you okay? Heather?" "Yeah..." I swallowed thickly and that was a mistake. I threw up some more, kneeling on the floor, feeling like I was dying. "Heather?&q... 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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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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I kneel in front of Dominatrix Persephone
Fan Mail. I kneel in front of Persephone.. She looks amazing in Her latex catsuit, but there is something else eye catching. Chance, Persephone huge hó rse c... It looks intimidating in picture, but just think how it must look when it is right in front of your face!! Holding it in my sissy hands, i... 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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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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Jamie is taken Part 3
When this process was completed the Chinese gentleman s turned to his new acquisition in the floor. He lifted him up from the floor and deposited him on a high-backed chair; his legs still folded up, and tied him to it. Then he removed the strap from around his throat and instead shoved ... Read full Story
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Chinese Extremes Part 1
Phil had been looking forward to the competition for weeks and now that it was over, he felt slightly disappointed. Not that he really had anything to be disappointed about. He had advanced to the third round in the Karate tournament where he had met an admittedly better opponent. So it wasn't that ... 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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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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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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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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A Fairy Tale Part 2
=-=-Chapter Six-=-= I woke up sometime later and I was feeling better, even a little hungry actually, and I wanted a shower and I needed to pee and...I cocked my head as I heard the unmistakable sounds of Mistress Stacy's bed moving. She had a large one, king sized, with old springs or somethi... Read full Story
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She also conquered my soul...
Initiation in a new era... Almost three months since I offered my virginity to a wonderfull he-woman, Selmi... unfortunately I had to cancel the second day we planned to spend together with my LORDESS because I quitted the town where we met the day before. Since, only few summer fling messages...... 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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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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Fem Firm 3: The Return Of Frankie
PART 1 THE VISITOR Over the next couple of months, it was pretty much business as usual at the Firm. You know, depositions, court filings, motions, hot sloppy blow jobs and ass destroying anal sex (Thanks Angela!).Not to mention Friday Fuckfests. But since I started working here everyone se... Read full Story