Ladyboy Stories

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Ladyboy Maid

by HarlanPilate on Sep 25, 2017
Transsexuals & Crossdressers

'Hi,' she said, her voice sultry. 'I'm the new maid. Lisa.' The new maid had turned up at the house of Mark and Susan Reynolds. Mark had answered the door, and he was impressed. Lisa was around thirty, with large brown eyes and wide red ruby lips. Her exotic features made Mark think that she was from somewhere near Persia. She was about 5'6" in black high-...

Ladyboy DP for Thai Wife

by StarfireMayo on Sep 19, 2017
Transsexuals & Crossdressers

Part five of the erotic photo journals of an English Teacher in Thailand. * Dear Reader: Some people are not comfortable with their own sexuality and they object to cuckold and bi-sexual stories. That is okay - To those people I would suggest not to read this story or to leave your negative comments. * I opened my eyes and lay still in bed, awake unusu...

Ladyboy for my Thai Wife

by StarfireMayo on Sep 19, 2017
Transsexuals & Crossdressers

Dear Reader: Some people are not comfortable with their own sexuality and they object to cuckold stories and wife sharing. That is okay - To those people I would suggest not to read this story or to leave negative comments. To all the many others, and especially my thousands of readers and fans please read on- and enjoy. If you like this story, do not forget...

Ladyboy Loves Up The Midwest

by danielblue on Sep 16, 2017
Transsexuals & Crossdressers

When Jasmine, a Thai ladyboy, moved into a small town in Iowa the locals didn't know what had hit them. She was instantly the talk of the town; initially for being so different and exotic but once she opened her club her reputation spread right across the county and state line. It was only a really small place with just room enough for eight tables. But you...

A Ladyboy for Master Hans

by justincbenedict on Sep 16, 2017
Fetish

After Chip had cooked dinner and waited on Hans, and had his own meal in the kitchen, cleaning up quickly, he got busy polishing Hans's shoes and boots. But in the middle of polishing Master Hans's last set of boots, Hans interrupted Chip. "Chip. How many times I must tell you? You have not written down your Stuhlgang, your poo-poo!." Hans, who was a st...

A Ladyboy

by Owmyballs on Apr 29, 2025

Hello. My name is Chantara Noi. I am a twenty- two year old ladyboy from Bangkok Thailand who recently emigrated to the United States. Today I live in Columbus Ohio. I have shoulder length black hair and gorgeous brown eyes. I'm five foot two and petite with average sized breasts. Please don't ask if my tits are real. I'm a ladyboy...of course they're fake d...

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The Neighborhood Ladyboy Ch. 02

by Rstyusameg on Sep 16, 2017
Transsexuals & Crossdressers

All characters are fictional, except me, everyone in the story is over 21. My stories will involve, male/male sex, cross-dressing, and bad language, so if this offends you please don't bother reading. * It's been a week since that nameless Mexican fucker used and abused my asshole. What? He's not going to hit me up? Am I not good enough for him?! These th...

The Neighborhood Ladyboy Ch. 01

by Rstyusameg on Sep 16, 2017
Transsexuals & Crossdressers

All characters are fictional, except me, everyone in the story is over 21. My stories will involve, male/male sex, crossdressing, racism, bad language, and drug use. So if this offends you please don't bother reading. * Wearing my favorite low cut denim jeans, showing off the "tail" of the whale from my stringy pink thong, I walked into Albertsons. A loca...

Catia Becomes a Ladyboy Escort

by TimT1972 on Sep 14, 2017
Transsexuals & Crossdressers

The days when poverty stricken parents sold their children into slavery are a distant memory. They are stories from the nineteenth century not the twenty-first. This said, parents are quite entitled to earn a 'finder's fee' if they introduce prospective staff to an employer. Times were hard in Rio de Janeiro and Mateus' father wanted the best for his son....

My First Ladyboy

by 69plus1 on Sep 19, 2017
Transsexuals & Crossdressers

I was in my forties and was bored with life. My job sucked, my night life was the same over and over. Bar hopping hoping to get lucky and pick up some woman who would fuck me and not be crazy in the morning. Or maybe a hot guy just for the change of pace. Guys were just about the sex and usually didn't bring any baggage. So I was surfing the internet and ge...