Free Stories

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Group Sex
Jan and I have been together now about 4 years but known each other since High School. We are both in our early fifties. We had met a transgendered girl (Gabby) about a year ago and we get together about once a month and enjoy each other’s company, going out playing and having intimacy together. Gab... 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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Wie sich schlagartig mein Sex Leben änderte... Teil 1
ich war nun schon einige Zeit heimlicher Crossdresser. Nie wurde ich von meiner Freundin erwischt, auch wenn es manchmal wirklich knapp war! Ich hatte ein sicheres Versteck für meine schönen Sachen und meine Sextoys und konnte hin und wieder meine geheime Neigung ausleben wenn sie nicht da war.Trotz... Read full Story
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Surprise Ending (Part Three)
I rolled my dick around her hole to spread the precum off it and lubricate it. The feeling was sensational and I couldn't spend much time easing my way in --I shoved right in the the hilt in one steady push. Karla practically jumped off the couch and screamed. I thought maybe I had hurt her (I am... 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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The sissy dreams
Everyday I wake up in a state , halfway between a happy sissy and a closeted white boy. My mind is constantly trapped in that state. Suffering in silence, the people in my life seem to be oblivious to it, I have it well hid. 48 years of fist fights and weed, long hair and leather coats, Oilfield job... Read full Story
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Steve
So on AFF, I used to be gold but guys will just hit you up, sooo I got hit up by an 8in boy. Wasn't sure I'd want to prep up an 8 so I didn't get all ripped up, but nice profile and a fucks a fuck sometimes. What to wear to get cum in tonight? Still pretty warm, I'll go mini with tighter leotard (mo... Read full Story
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A Series of Perverse Dreams, Part 1
My relationship with Hannah had always been mutual in the idea that neither one of us was ever truly the dominant one. It was an equal, balanced relationship of mutual fucking and sucking. However, I had REALLY enjoyed being made into a submissive sissy slut by Nikki. Something changed in me after o... Read full Story
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Working for a Living Chapter 6
I slid out of the old Ford truck driver's side door. Surprisingly, my legs felt a bit shaky as my feet hit the concrete driveway of the Malibu mansion. I nervously straightened my cut-off shorts as I walked around the truck. She was waiting by the tailgate with a big smile on her face. "Wow Jai... Read full Story
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The journey down the Rabbit Hole...
Nearly 30 years, living a double life. Sneaking around on two Xwives, several girlfriends, all to play with men.Play,and play and play. Responding to personal adds in the paper at first, then I found the Bath House. Wow, to a closeted homophobic acting oilfield lifestyle kind of guy, who could hide ... Read full Story
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Dirty Business Trip
Chapter 1: The Transsexual Hotel Encounter "Yes, I am checking in," I said, putting my credit card on the desk. The woman behind the desk took the card and looked at the name. She was about 5 feet 10 inches tall with dark black hair and brown eyes. Her skin was beautifully tanned and he... 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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My First Experience
Preface: A few years ago I was surfing craigslist (back when that WAS a thing) and found a couple looking for a man. I responded to that post and went back and forth until we set up a time to play. I arrived on the night and had a few drinks, We chatted and I noticed that the husband kept touchi... Read full Story
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From a 50's virgin to a Mature good for all
***Prologue - Confessions: Every day since I offered my virginity, I put myself in the shoes of a woman. The little town where I live forbids me to show myself socially. However I made myself an accomplice, my epilator who receives me after closing. Since my new beginning, male masturbations are not... Read full Story
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Sissy Training
This is a true story, looking back it is hard to believe it actually happened, but it did. I was working for the government in DC and living in Maryland and my fiancé was up near Cape Cod. Just about every weekend she’d fly down or I’d fly up to spend the weekend together. We&r... Read full Story
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A Schoolgirl Story Chapter 2
I must apologise for the amount of time that it has taken for the second chapter of this story to come out. I have to admit that I had kind of abandoned it, but all your lovely feedback comments made me decide that I couldn't leave this one hanging. So thank you to everyone who wanted more of Wendy,... Read full Story
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Samantha sissy TGTF
Theme and genre of the story: The genre is about gender bender, futanari, gay, physical transformations of the body, magic and biology, the kink in particular that must excite in the story is the perversion of the transformation of the body and mind through a magical element that manipulates biol... Read full Story
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A Picture Perfect Sissy
"Holly, hold your breasts up. That's it honey. Squeeze the nipples between your fingers. Make them hard for me, sweetie." Jason lifted and pushed his soft breasts together, squeezed the small dark nipples, and hurriedly looked up to see if what he was doing was okay. He really wanted wh... Read full Story
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Pa-mie sex-agénaire
Luxure frénétique d’une pa-mie sex-agénaire; entre rêve et réalité Je n’avais jamais fantasmé de mec viril, même après avoir offert ma virginité; mais à une fabuleuse sissy. Avant mon Ѐre, mes préférences de fantasmes étaient toujours avec des lui-femme glabres, idem concernant mes relations d’aprè... Read full Story
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HELPLESS TO MY CRAVING FOR BLACK COCK
This is a totally true account of my addiction to meth and its hand in turning me into the he[pless sissy I've become to my weakness for BBC. My name as a regular male is Richie Budd. But by reading this you'll soon realize that nothing is normal. Not only was I Richard Budd. I spent an equal, if ... Read full Story
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Tight Spot
XtinaSmith2017 Cody bit his lip as he looked over towards the shop, a little anxious about their planned endeavor but not wanting to come off as uncool to his friends, "Are you sure this is a good idea?" he asked. His friends grinned and laughed, playfully nudging him as they made their way ... Read full Story
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Fun time with russian shemales in Moscow
The first day, I was with my Russian friend, who introduced to me the Russian shemale escort. Since I know he is a big fan of shemales, so I wasn't shy of asking him about shemale escorts in Russia. He called in a shemale escort for me rightaway. I was staying in a hotel in downtown Moscow. Since my... Read full Story
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Big Surpise In Small Package
It was a Friday night and I was extremely horny and just my luck my girlfriend was out of town, but I wasn't horny for her I was craving cock. I knew I was bi for a long time and loved to have a nice hard cock to play with every once in awhile. So I decide to call my girlfriend to tell her I was goi... Read full Story
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lust of a sex-agenarian nana-pops
Frenzied lust of a sex-agenarian nana-pops; between dream and reality I had never fantasized of a manly man, even after offering my virginity; to a fabulous sissy. Before my new Era, my fantasy preferences were always with glabrous he-she’s, same about my relationships after… BUT BUT BUT… My last t... Read full Story
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Caught by the Lodger Chapter 2
Over the next few months Rachel continued my training. She was determined to transform me, in her own words, into 'the perfect sissy slut girlfriend', and I was only too happy to go along with it. There are a strict set of rules that I have to follow. I am allowed to wear my male clothes when I'm... Read full Story
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Fem Firm 2 -The Weathergirl
PART 1: A COURTESY CLIENT BLOWJOB Three weeks into my gig at Coxon & Dicster had been a blast. At first, a few of the girls had some reservations about me working there because I wasn't transgendered myself but I guess I won them over with my naturally cheerful personality. At least,... Read full Story
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Becoming Sissy
I remember my first true and sober gay sexual encounter. The guy from the party that was my first BJ and first penetration was one of the closest friends of the group. He bought a house up north and 3 of the girls and me went to his house to help paint and work on some things. This was about a mo... Read full Story
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Club sex the 25yo
There’s a very special private club around, it’d meetings take place in a very secret place. It takes a lot to gain membership. You have to either have a lot of money AND a friend in the club OR you have to take part in the ceremonies for at least a year. Also you have to be willing to b... Read full Story
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Freak House Superstar Come Fest
Kiki and Ty Blaze were doing their thing. They were living on their love and passion, literally. The couple had taken their love, passion and desire to please one another and turned it into their livelihood. They had become stars in the world of underground porn. Their production studio, Nasty Nigga... Read full Story
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A Night of Makeup, Cock and Cum
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,... Read full Story
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The Gang
I had always thought of myself as female in spite of the fact that I was born with male genitlia. Even in my earliest memories where I had witness sex, I identified with the female in the relationship. As a small young child, I had always longed for womanhood each time I heard a woman sing or especi... Read full Story
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A Slut is Born Chapter 2
The week went by slowly as I digested what Jim had done to me last Saturday. As I walked around school, I found myself looking at people differently, wondering if any of them had ever been treated the way I had. This would always bring the details of what Jim had done to my mind and my cock would im... Read full Story
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Fender Bender Chapter 9
My name is Robert, I have been cross dressing since I was 14. I turned 18 last summer and this story takes place during my senior year in High School. I am 5'9" 160 pounds, blonde hair and blue eyes. When I am dressed I call myself Vicki. __________ I had met Julie at a recent party. Well... 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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Becoming a Drag Queen
I was thrilled when my boss told me he was sending me to San Francisco for a conference. It was a location on my "Top 10 places I wanted to go". I went online and Googled the major attractions and tourist "must sees in San Francisco. The conference was Wednesday to Friday and I figure... 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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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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Latex succubus
The lights of the city obscured the supposedly brilliant starlight in the night sky, leaving only dim and scattered scattered stars adorning the gloomy night sky half-covered by dark clouds, and the crescent-like crescent moon guarding it in the distance makes the night seem less empty Lonely. Mayb... Read full Story
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When Fantasy Comes True 2
After my first threesome encounter with Jenni and her friend, getting a golden shower from three trans women was a bonus. Being drunk and now four of us snuggled in bed, i thought the night had ended but i did hope for more. I was not disappointed as Jenni's friend (Sasha) who had been sleeping d... Read full Story
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The Game 2
That next morning again Ada and I went down for breakfast and the table was smaller, It wasn't as grand as it had once been and to every guy at the table was now at least two girls. We had our normal breakfast and for once there seemed to be a little more chat between everyone, I think after bei... Read full Story
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Dominated sissy goodgurl34
Mmmm ty Sir Deitrich --I'm standing in your open doorway wearing black latex stockings and garter and some hott red lace panties over top -I have a black corset on and a very sheer dress on ,wig and gurl mask ---my wrists are cuffed to a circle hook one on each side of the doorway door jam about 6... Read full Story
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More from my closet....
......being single is so better to play my games, no wives to take up my day, no one to lie to anymore about where I went... I had a layover for 3days in Vancouver last fall, three days all to myself, with the aid of google maps I found the local steambath for men. Steamworks it was called, set... Read full Story
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Gangbanged at the beach
My BBC friend took me to the beach, where people make sex. We arrived in his van. I was in the back of the van, chained blind folded, with my mouth wide open and a huge horse dildo in my sissy pussy. Suddenly I hear the van door opening. I hear many voices of other men. My BBC friend was telling oth... 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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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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T-Girl University
Jason was apprehensive about starting college, as any freshman would be. His high school girlfriend, Becky, whom he loved dearly, was going to a different college on the opposite side of the country. They had to promised to stay together but Jason was worried; there would be a lot of temptation for ... Read full Story
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Discovering Mistress Sarah's World Part 5
Chapter 13 Sinking Deeper Into The Feminine World *** Prologue - Joe has made a trip down south to visit for the first time, his online Mistress. Over the past few years she has slowly feminized him with the help of Miss May. Upon his arrival at Mistress Sarah's house, she puts his feminization i... Read full Story
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Surprise Ending (Part One)
My wife is the picture of professionalism from 8 to 5, but after hours she is a sexual dynamo who loves men and women. Throughout our relationship she has introduced several of her gal pals into our bedroom, hot tub, shower, etc...you get the idea. Anyway, two weeks ago she let me know that one o... Read full Story
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Surprise Ending (Part Two)
My curiosity, unconscious urges, and my horniness pushed me into action. I gently cradled Karla's balls in my left hand while my right hand settled on her taut ass. I caressed both and then let my left hand move on to her now blood engorged shecock. I am a pretty big dude, but I could hardly get ... Read full Story
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Threesome goes clubbing
Ft. Lauderdale is probably the most LGBT friendly city on the east coast. So many nice restaurants and clubs that welcome all and have many LGBT employees as well. Lydia and I have been married several months, we had met Joanne an absolute amazing transgender girl during a weekend trip to the Baha... Read full Story
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Being Barbi's Bitch
After ten wasted years of foolishly trusting in love to 'cure' me of my femininity, I had only just begun to re-embrace the sissy inside me when something made me reach out to an old friend. What made me do it, I really don't know. Although I was once again revelling in even the smallest aspects of ... Read full Story
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Career Shift
Receptions are not my favourite things in the world to attend. I don't mingle and 'rub elbows' like agents and sales people do. I usually end up at the bar drinking alone, looking at all the phoney people. I am a writer, a sports column writer more specifically. The magazine that I write for is one ... 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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Tommy Tries to Make It Up
Tommy Tries to Make It Up I have written about Tommy before. He was the eighteen year old neighbor that always stared at me checking me out, basically eye fucking me and that made me so hot and horny I eventually took his virginity and trained up on being a great lover. Well he had moved out... 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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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