Ladyboy Fuck Guy Stories

265,399 results
Orientation
Length
Source
Infinite Scroll

Briefly Encountered

by wylite on Sep 16, 2017
Transsexuals & Crossdressers

I had business in the Middle East and this required frequent trips between the UK and various middle Eastern capitals. The routing of my flights was my choice and I often used to transit via Amsterdam; I would ensure that there was a good long transit time between my flights and this allowed me to make leisurely visits to Amsterdam's city centre. It's a shor...

Shemale in Porn Theatre

by Subman666 on Apr 14, 2020
Transgender & Crossdressers

This action begins with my weekly trip to the local porn shop, made up of the typical video booths as well as four open rooms with big TVs showing various movies. It's afternoon when I enter, and I immediately walk into the video viewing area, a dark open room with straight porn continuously running. The place is set up like a big square track, so as I walk...

A Perfect Life

by FarangPrince on Sep 13, 2017
Transsexuals & Crossdressers

As I write this, I am sitting at my laptop computer on the balcony of my apartment in Bangkok, Thailand. Behind me my ladyboy lover is puttering around in the kitchen, washing the dishes from our breakfast. My lover is a beautiful Thai ladyboy. She has gorgeous features – lovely almond-shaped dark eyes, upturned sexy lips, dark smooth skin, thick black hair...

Sex therapist

by qaz on Sep 1, 2016
Miscellaneous

Who do we follow?What's next? A boy A girl What's next? A boy A girl...

Open in Reader

Seduced and Hoodwinked Ch. 02

by walterio on Dec 31, 2017
Transsexuals & Crossdressers

ACCEPTING JASMINE Thursdays were working out wonderfully for Darin as a masseur at the Spa. He would massage the voluptuous Rita first and as always, she would leave him with a boner and ready for sex. Jasmine was his second and only client and they would spend hours together. He massaged her lovely petite body and he loved her tits and ass. She loved the w...

The Lab Rat Pt. 04

by TheMarlboroMan on May 13, 2020
Transgender & Crossdressers

The Lab Rat Part 4 Karla Wasley, Leah Guzman, Robin Venters, and Anna Edwards were standing there in an observation room watching me in my total nakedness via the eight-foot wall screen thanks to hidden cameras in the examination room as I came all over the ladyboy's face after he could no longer swallow what I was spurting fast enough. What struck them as...

My Thai Ladyboy

by TheSevenSeas on Apr 27, 2020
Transgender & Crossdressers

There is a saying that 'when one door closes, another opens.' That was certainly true for me. My relationship with Jen (see my previous story: My First Ladyboy) continued for some time, but we rarely managed to see each other. I was mostly working in Africa and just couldn't get over to the Philippines very often. Eventually we drifted apart. Yet I was truly...

Another Day, Different Office

by chelseabi on Sep 16, 2017
Transsexuals & Crossdressers

It's been a couple of months since my first all guy encounter and my life has changed somewhat. There have been numerous liaisons, with couples and single guys and I know that I'm now treading a fine line between my marriage, work and the sex I now crave. As for my marriage things are normal, we have been together for years and as so often happens we have...

My Cleaner Ch. 02

by gendidi on Sep 15, 2017
Transsexuals & Crossdressers

I only went back to my home country once a year. This year, I went back alone because my wife wasn't physically fit to travel. I had to leave her back in UK because my parents were in their late 70s. I needed to spend as much time with them as possible. When I arrived in Kuala Lumpur, it was late afternoon. I didn't sleep well at all on the flight and I wa...

Transsexual Journey 02

by walterio on Sep 19, 2017
Transsexuals & Crossdressers

DAY TWO OF THE CRUISE TO BARCELONA Jay woke up leisurely on Sunday morning and lay in bed for a while thinking about his encounter with Caridad the night before. He was still somewhat shaken by his willingness to have sex with a transsexual but more so, that he had enjoyed it so much. She was so damn pretty and shapely that it had been way too easy. Her bod...