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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...

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...

Pushing Boundaries

by Lost_Yonder on Sep 17, 2017
Mature

This story is dedicated to a special young lady who one day did walk into my life. With much regret, she didn't stay long. The following is based on "what if" -- what if she stayed longer than a night. Despite her transience, her spirit continues to inspire me, to push me to transcend my own borders...Maybe someday she will find this and recognize herself in...

The unexpected housekeeper

by manhasso on Mar 30, 2020
Transgender & Crossdressers

After experiencing difficulties in his personal life, a lawyer discovers the benefits of having a live-in housemaid. 1.Prelude After almost 20 years of legal profession, I was now an accomplished lawyer: I had my own firm, several younger lawyers working for me, big and important clients, a sports car, and a house on the hills overlooking the city. But...

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...

Banker's First Encounter

by gendidi on Sep 13, 2017
Transsexuals & Crossdressers

The story below was based on my personal experience... During the economy downturn in the 90's. I was in my later 20s. My job then was a banker. Banks stopped lending money and all those bankers who managed to keep their jobs were told to sell fixed deposits instead to keep the bank healthy. Being a sales guy. I went out all day trying to meet customers to...

The Club

by SweeetLee on Sep 13, 2017
Transsexuals & Crossdressers

They entered the club and were greeted warmly by a long-time acquaintance. She was a dark haired beauty, and the one who had first told them about this place and used her membership to get them in. It wasn't that it was exclusive. It was off-limits to outsiders. You had to know someone just to learn the address. She ushered them through the very legitimate...

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....

One Night in Bangkok

by trouser on Oct 25, 2015
Transsexual

You were extremely nervous. Not only was it your first time to Bangkok, or Asia in general, but you had also arranged to turn one of your most secret fantasies into reality: One night with a thai ladyboy. And since your company had sent you for an important meeting to Bangkok the chance was finally there. You had already hooked up with some potential ladyboy...

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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...