Free Stories

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My amazing Filipina girl
Today's post is not a usual ladyboy sex story that we all got used to, but something more romantic, down-to-earth and non-porn. Thanks British Buy for sharing this story and being so brave in making your fantasies real and finding your true love. I wasn't looking when I found her. I wasn't reall... Read full Story
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Thai Ladyboy Interview
An Afternoon With Some Thai Ladyboys I spent this afternoon with 6 Thai ladyboys. No, don't go thinking that I tried them out. I didn't. I spent a few hours chatting with them, finding about them, trying to understand what makes them tick and learning about their experiences and the guys who util... Read full Story
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Soo, my ladyboy friend in Bangkok
This shemale story is not your usual one as it's written by a lesbian girl Jamie and it involves a very sensual description of sex with an Asian ladyboy. Enjoy reading! Well as an openly gay Lesbian woman (submissive as I say) a long way indeed. My friend in Bangkok, Soo is a beautiful, articula... Read full Story
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Philippines vacation with a Dominant Big Cock Ladyboy (Part II)
Please read the initial story to get proper context. I spent a 9-day vacation in the Philippines with a sexy and super sweet 34-year old Filipina Ladyboy I met online and developed a relationship with before traveling to meet her. It was the first and only time to visit the Philippines. Less t... Read full Story
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A LadyBoy For My Wife
I have been happily married to my sexy Thai wife Lisa for three years now. My wife is Thai is petite (5'1") with a stunning figure, a tight ass and long waist length black hair. We had met in a bar in Thailand and subsequently we were married back here in the UK. She was very loving with m... 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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Philippines Vacation with a Dominant Big Cock Ladyboy
I am still in a state of unbelievable joy that I was lucky enough to experience this but I 100% did and I can’t stop thinking about it as I thought things like this only happen in porn or fantasies. Buckle up because this is a wild one and happened in Manila May 2024. I had the opportunity to vi... Read full Story
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Ladyboy orgy in Thailand
During one of my many nights in the sleaze capital of the world Pattaya, Thailand I was at a certain ladyboy bar all dressed up in my sexiest outfit that the "girls" had ask me to wear in as I had shown them some pics of me dressed. Not that I could ever hope to compete with any of them! ... Read full Story
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My second time with ladyboy Nan
If you like the idea of a girl going at it with a ladyboy and follow the ladyboy stories section of our blog for some time, you should remember the story about Thai ladyboy Nan that our reader Julia wrote. Well, this is her second report and I hope you enjoy it as much as the first one. This time... Read full Story
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My first time with ladyboy
My first time with ladyboy happens in Thailand when i was 19years old. I was in beach party drinking with my brother, we drink some amount and get drunk and good mood, my brother goes toilet and i met couple girls there washing hands and start chatting with them, i didnt know there is so beutiful la... Read full Story
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Bangkok Night with Thai Ladyboy Dancer
I was visiting Thailand back in the 90s and was blown away by the “Potpourri” of sites, sounds, and smells (not all of them good) of this city. Beautiful women were at every corner and very friendly to foreigners. I went out with a group of guys on the town after dark to check out the go-go bar scen... Read full Story
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Ladyboy surprise in Bankgkok
A few years ago I went to Thailand for the first time, my first stop was the bustling city of Bangkok. I had heard stories about the nightlife, the girls and the tourists. The country had never appealed to me that much but through a twist of fate I ended up visiting the city of sin for a couple of d... Read full Story
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Trans Daughter F*cks Daddy
This is true story. I am 50 age n avid shemale , Transgender, ladyboy lover. Two years back i was member of LGBTQIA community in Pune where i met this ladyboy trans girl . We spoke, chat sone time and immediately clicked. She said she lost her father and wanna me to be her daddy. I agreed and i ac... Read full Story
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My First Ladyboy Adventure
I had been watching ts porn and thinking about visiting an escort for a while, when I found myself working in London and actually got the oportunity. I had been checking out the London Eros guide on the internet and had called several tgirls when I came across Seri Atika's profile. I called he... Read full Story
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CD/TS Shemale Chrissy Fucked On the Ranch
I met John on the swinger site AdultFriendFinder. He was everything I was looking for: old, in his late 60s, and not rich, but financially stable and independent, owning a ranch that has been in his family for generations. Maybe he could become the Sugar Daddy I am looking for? I am a shaved-smooth ... Read full Story
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Free Shemale Dating Site The Place Where I Want To Spend My Life
Browsing through all payed porn services left my wallet thin, so I went for free shemale dating site option. When my boss noticed that I was paying less attention to work and more attention to Shemales, he fired me without any notice. I was hit hard with the economic crisis - the bank sell my hou... Read full Story
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Ladyboy Surprise - Part 2
My jaw hit the floor. Between the legs of these to beautiful girls were 6 inch cocks! I was stunned. Here I am standing naked in a shower with a raging hard on with what I thought were two gorgeous women, and they turn out to have dicks! I didn't know whether to shit or go blind! One of the ladyboys... Read full Story
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Ladyboy Switch Story
I am messed up with how I feel about this. I still love looking at women. I love tits and arse. I like the soft feel of women – kissing them and feeling their bodies. I don’t look at men in public and get turned on – men with clothes on do nothing for me. Put me somewhere that I can see those same m... Read full Story
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Why you should never cam
* Sorry for the poor writing but since it is the summer and I am taking sometime off to reflect before starting school next year I thought I would write up about what had happened to me the summer before. It is currently a work in progress and if spot any spelling mistakes or errors feel free to cor... Read full Story
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Pune crossdresser Night Girl
Hi friends, I hope you liked my earlier stories. This is my new story about a lady boy / crossdresser / sissy boy. Around 2 years back I came across a profile on Planet Romeo with name Nightgirl. I sent her message that i found her sexy and attracted to her and wanna meet her. I am alway... Read full Story
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Ladyboy Surprise - Part 1
It has been many years now, but I can't seem to forget what happened to me. I was as a young seaman in the Navy. I still wake up at night rock hard thinking about it! I am happily married now to a good woman and have a few kids, but I can't get this image out of my mind. We had been out to sea fo... Read full Story
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Wife Left Me so I Could be a Girl
I Am The Girl My Wife Did Not Want As the only child of a single mother I grew up around all things feminine. Having lingerie and stockings drying in the bathroom was normal for me and I always loved how pretty the full cut nylon panties and slips with tons of lace looked. I lived at home with... Read full Story
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Casino Girl
I had been working as a casino dealer for several years and would occasionally meet some very attractive women and chat. Asian women have always been attractive to me, whether the exotic appearance or maybe because my Mom was Pacific Islander, and a lot of people thought I was Asian. Mia was a bit... Read full Story
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Jo, Shemale Goddess! Part 1
Jo plumped the cushion and carefully positioned it until it was precisely at the right angle. Nothing less than perfection would do. Ricki, her friend of twelve years was coming to stay overnight and she would notice if the tiniest thing was out of place. An impatient knock on the door signalled ... Read full Story
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The Girl Next Door Ch. 01 by derezzed ©
Michael was your average 21-year-old college student. He was on his way home from college for summer break after finishing his finals and looking forward to a few months of relaxation. Driving home Michael reflected on his past three years of college. It had been a great junior year. He met a lot of... Read full Story
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Gay friend of my brothers
As I mentioned in previous stories, my brothers met Adrian at university, he was studying nursing, he was in the same year as my brother and they were studying one or another subject together, Adrian has brown skin, green eyes, his short Chinese hair He has a slim body, he was 1.69 tall, his nose is... Read full Story
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The Girl Next Door Ch. 01
derezzed Michael was your average 21-year-old college student. He was on his way home from college for summer break after finishing his finals and looking forward to a few months of relaxation. Driving home Michael reflected on his past three years of college. It had been a great junior year. H... Read full Story
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Fucked by a Shemale
My names - and I would like to tell you about a very sexual experience I had recently. First I would like to tell you I’m 30 years old and never had a gay experience, until now. It was a Saturday night, me and my brother were round the local town, after a few too many beers my brother met a bi... Read full Story
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Buffy the Shemale Vampire Slayer Part 1
Waking to sunlight streaming through her bedroom window, between the parted curtains, Buffy Summers frowned, blinking. She'd had some strange dreams, including a few that had been prophetic, but nothing like the bizarre nightmare she'd awakened from just now. Last night, she'd fought a Feral Demon a... Read full Story
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Shemale Adventure
You: early 20's, tall boyish good looks with a lean and muscular body. Dressed in tight leather pants, from behind your tight buns are revealed by the shiny black leather, as are your cock and balls from the front. You are wearing black leather boots and a denim shirt that refuses to hide your stron... Read full Story
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Making Shemale Vanity Tube Your Homepage Is A Great Idea!
It all started as a joke. My roommates at the time pulled a prank on me and made Shemale Vanity Tube my homepage. You see, I was about to hook up with this chick one night so they sneaked inside my room before we got there and made that change. Once I turned on my screen in search for some sexy musi... Read full Story
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Shemale Sex Pics Are My Life's Poetry
My younger days are very hard to explain. All I ever wanted to do is to dress in girl's clothes, imagine playing with Barbies and their houses and watching my mom put on her makeup every day before she took me to school. I knew I wanted to become more girl and less boy, but knew nothing about it. ... Read full Story
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From Gloryhole Peegasm to Shemale
I was in a porn video booth. I young guy stepped into the next one. I was already jerking my small dick, but he didn't even pull his pants down. He asked me if I wanted my dick sucked. Actually I think he said something like, "hey, let me suck your dick." Recently I had let some weird, ... Read full Story
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Father-In-Law Shemale Adventure
My wife's parents were visiting LA from back east. We live in a small one-bedroom apartment in the valley. She wanted them to stay with us but we didn't have room. They got a room in West Hollywood. My wife and her mom had gone shopping for the day. I was supposed to be at work but at the last momen... Read full Story
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My way to shemale sex
It all started with porn. 10 years ago, i was watching porn on my bed, jerking off watching a girl sucking a big cock. I looked at my cock and started wondering what that beautiful peace of meat tasted like. After a few moments of hesitation, my curiosity took over and i put my back against the wall... Read full Story
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Real Story with a Shemale Escort
One day I dreamt about a big black cock fucking me on doggy style. The dream felt so real that it made me to ejaculated in my sleep without even touching my cock. It was the first time this happened to me and I was surprised because I’d never felt gay. My underwear became a mess filling the whole su... Read full Story
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Buffy the Shemale Vampire Slayer Part 2
Buffy waited until twilight, hiding out in her bedroom, as she tried to come to terms with the bizarre fate that had befallen her, thanks to the Feral demon's bite. It wasn't easy, psychologically, physically, or otherwise, to have gone to sleep a girl and to have awakened a hermaphrodite. She wasn'... Read full Story
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Buffy the Shemale Vampire Slayer Part 13
Buffy's cock slipped out of Baubo's mouth, and she licked the smooth skin of the stiff, elongated shaft with her tongue. Baubo had no hands, but, even so, she was a superb cock sucker. More than once, she brought the Slayer to the brink of orgasm, then backed off, letting Buffy's sexual passion abat... Read full Story
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My first shemale
This is the story of my first she male. I had always been curious about dicks. I had always been attracted to women and I loved to watch a woman get pounded by a big cock. But after awhile I realized that when I tried to imagine the porno, I always imagined myself in place of the girl. One day, when... Read full Story
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The Girl Next Door Ch. 03 by derezzed ©
Chapter 3 – The Night Out Michael woke up on Monday morning feeling quite relaxed. The sun filtered in through the blinds towards him. He felt warm from the gentle rays. As Michael became more alert, he examined his surroundings. The feeling of silk sheets wrapped around him and Alexis's arm casu... Read full Story
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The Big Mature Shemale Next Door
The Big Mature Shemale Next Door SugarandSalt "Please can I just wear my old swimming trunks?" Warren begged. "No!" his mom yelled back from the other room. "Barbara purchased that for you. It was expensive so you better remember to thank her." Warren looked at himself in the full length mir... Read full Story
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Buffy the Shemale Vampire Slayer Part 3
Buffy couldn't stop smiling. It felt great to have left Spike on his knees, clutching his balls in pain after she'd sucked his cock and swallowed his load of icy vampire's semen. Sex was about power, not love, and nothing made a girl feel more powerful than reducing a man-or, in Spike's case, a u... Read full Story
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Tgirl Shemale porn cinema slut
As you know I'm very much a normal living sort of TGirl, cooking, shopping, cleaning, just day to day stuff like everyone else...I haven't started baking cakes for the local Women's Institute or joined a knitting circle yet, but I'm sure you get the general idea!! Sometimes, however, I get the ur... Read full Story
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New Girl in Town
Margo sat next to me in the coffee shop late that Saturday afternoon. His real name was Mark, but he was one of the loveliest Drag Queens in New York City. I had been dressing secretly at home in my mother’s and sister’s clothes for just over three years, but at 18 years old, I had never... Read full Story
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SheMale Pussy and Cock
I once had a friend who always said "never fuck anything you can't bench-press". He was right, the biggest benefit of having sex with someone smaller and lighter than you is you can lift them easily ! On a recent trip to Thailand I couldn't take my eye's off a stunning, short, tiny but ... Read full Story
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A Girl's Best Friend
The party was in full swing when Ryanna and her friends arrived. Of course, they were an hour late, since Glenys had gotten lost on the way. The house was out in the back woods; the owners didn't exactly go out of their way to make it easy to find. Their fellow townspeople probably would have frowne... Read full Story
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I was Teen Shemale for the US Army
Chapter 1 Reform School Romance! I couldn't believe that all I got from my uncle Bill when he died after all he said to me about my being his favorite grand nephew was an old diary from World War II. I mean I thought we got along pretty darn good, and its not like he had any money or anyth... Read full Story
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The Girl Next Door Ch. 02 by derezzed ©
Chapter 2 – Taking the Next Step Into Depravity Michael hardly got any sleep that night. When he did his dreams were filled with images of Jenny and her large penis. He tossed and turned in frustration. As he rolled over for what felt like the thousandth time he was blinded by the sunlight that h... Read full Story
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My Romantic One Night Stand with a Beautiful T-girl.
My Romantic One Night Stand with a Beautiful T-girl. A friend of mine landed a gig DJing at the well known dance club in West Village of New York City. She invited me to check it out. Why not, I had no plans that weekend and she can put me on the VIP guest list. Which means I don’t have to wai... Read full Story
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The Girl Next Door Ch. 02
derezzed Chapter 2 – Taking the Next Step Into Depravity Michael hardly got any sleep that night. When he did his dreams were filled with images of Jenny and her large penis. He tossed and turned in frustration. As he rolled over for what felt like the thousandth time he was blinded by the s... Read full Story
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The Girl Next Door Ch. 03
derezzed Chapter 3 – The Night Out Michael woke up on Monday morning feeling quite relaxed. The sun filtered in through the blinds towards him. He felt warm from the gentle rays. As Michael became more alert, he examined his surroundings. The feeling of silk sheets wrapped around him and Ale... Read full Story
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I will go back there!
Gotta thank our reader Amanda for this lovely ladyboy sex story. As an openly gay women I had heard so much about Katoeys in Thailand and that they were affectionate and prepared to do most things. I have to go to Bangkok on a marketing junket so decide to test the waters. The first bar I walked ... Read full Story
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Ladyboy Fuck Show
Thai Kathoey Ladyboy Fuck Show in Patpong So last night my TG girlfriend and I went to Bangkok's Patpong prostitutions zone to see a fuck show. Instead of the "normal" sex show with old women shooting darts out of their twats, we asked the touts to take us to a ladyboy fucking show. ... Read full Story
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Busted and Hoodwinked
INTRODUCTION Mack and Barry were cell mates in prison which is where they first met. They had both been convicted of burglary and breaking and entering. The befriended each other while in prison and became lovers. Barry was gay and Mack became a bisexual during their time in the same cell. Mack a... Read full Story
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Fucked by indonesian ladyboys
this is a true story of what actually happened to me in bali When i was 17 i was on holiday in bali, indonesia. i'd only had sex once prior, with a genetic girl, and i barely managed to get hard and wasn't able to cum so i knew pussy wasn't for me. i had been clubbing several tim... Read full Story
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I prefer ladyboys
I prefer Ladyboys than girls and if that makes me a gay guy then so be it. I live on my own in New Zealand and have a Ladyboy Friend in Thailand, whom I am very much in love with. We are planning to live together in Thailand within the next months. My Ladyboy Friend is very Beautiful and SHE takes... Read full Story