Ladyboy Fuck Guy Stories

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Anal Anywhere, Anytime Ch. 02

by walterio on Jan 22, 2020
Anal

BEFORE CHARLOTTE As long as Walt could remember he had been drawn to a shapely female bottom. I didn't have sex until I was 18 but I had hundreds of boners from just looking at the outline of curvy buttocks contained in skirts and slacks. I found myself watching TV hoping to get a look at an actress's derriere. Even during commercials, I checked out a curvy...

Transsexual Journey 01

by walterio on Sep 19, 2017
Transsexuals & Crossdressers

PRELUDE Jay woke up to the gentle movement of the cruise ship through the Atlantic. His bladder needed relief so he eased out of bed and quietly used the bathroom in the stateroom. Once he had taken his morning piss, he washed his hands and cock before crawling back in bed. As he approached the bed he admired the Spanish beauty lying there with her back to...

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...

NOT Waiting For Godot XXX

by eneo on Sep 1, 2017
Humor & Satire

Characters: Noi Toi Moi, the ladyboy actress who plays Noi Me, the writer, director and DP (director of photography you dirty-minded people!) Yes, I appear in all of my movies, usually as the lead actor, a balding Jewish nebbish who gets the best and prettiest asian ladyboys. and featuring Ron Jeremy, as Marlan Bondo Opening Scene: [Dialogue between T...

Craigslist Bottom Bitch

by xploring96 on Mar 21, 2018
Transsexuals & Crossdressers

The following story includes transgender characters, Domination/submission, and denigrating terms used to humiliate. If this offends you please do not read any further. This is the second chapter in this series and picks up immediately after the first chapter. I recommend that you read Craigslist Cumslut first. In case you decide not to here is a summary....

Seduced and Hoodwinked

by walterio on Dec 27, 2017
Transsexuals & Crossdressers

INTRODUCTION Darin Thomas loved his job as a masseuse working at an upscale spa in California. He loved massaging the bodies of wealthy and horny women. There were some who just had a massage and others who wanted sex following the massage. Each massage room was private and the door could be locked to insure privacy and no interruptions. He was still stud...

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...

Busted and Hoodwinked

by walterio on Sep 16, 2017
Transsexuals & Crossdressers

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 actually liked fucking Barry and having Barry suck his cock. Ma...

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...