Ladyboy Stories

221 results
Orientation
Length
Source
Infinite Scroll

Addicted to Pream's Cream

by Vodka_Jim on Sep 26, 2017
Transsexuals & Crossdressers

It didn't take long after my divorce to settle into a routine. I had my kids the first, third, and fifth weekend of every month. That left me with a lot of free time on the second and fourth weekend. I wasn't inclined to date much at that point and had no real interest in hooking up through Tinder or other dating apps. So my routine on those Fridays was to g...

Jamie's Descent Pt. 01

by nikkiesilk on Sep 18, 2017
Transsexuals & Crossdressers

Chapter 1 What did we do before social media? How did we manage to get through the day without that endless stream of dirty jokes, funny photographs, gossip and links to dodgy websites that now fill our lives? Yeah, yeah, I can hear you grumble. Get on with it, I can hear you say. Well, dear reader, it was one of those links that started me down the road to...

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...

Transsexual Journey 03

by walterio on Sep 19, 2017
Transsexuals & Crossdressers

ONLY TWO DAYS LEFT BEFORE ARRIVING IN BARCELONA Jay had never in his life that he would have hooked up with a ladyboy. He also never expected that he would enjoy the brief affair as much as he did. He had to admit that Caridad was as beautiful and shapely as any woman he had dated. The fact that only he knew that she was a ladyboy was also a turn-on for him...

More Than a Lady

by danielblue on Sep 14, 2017
Transsexuals & Crossdressers

Doctor Carter surveyed the gathering of ladies before him. Something wasn't quite right, but he just couldn't put his finger on what it was. He had been invited to speak on Female Reproductive Health but the women before him were neither the charity-driven older matrons nor eager young housewives that he expected. They were gathered in the private function r...

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...

Thai Travels Ch. 06

by S_Queen on Jan 4, 2018
Transsexuals & Crossdressers

Welcome back, readers, for the final chapter of my story. If you've been with me since the beginning, you will have accompanied me on a taboo shattering journey, both geographical and sexual. I discovered a flair for public sex, I engaged in group sex and threesomes with lesbians, I fucked gays up the arse and received expert blowjobs from them, I played wit...

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...

Cockatoo Pt. 16

by nikkiesilk on Sep 14, 2017
Transsexuals & Crossdressers

I live for feedback. ***** We decided to have a celebration dinner tonight downstairs and Alex disappeared to the restaurant to organise the dinner. Areeya had to go down to Cockatoo to sort out some issues they were having and so I was left to my own devices for a while. We agreed we would all get together at Cockatoo for a drink before dinner. The firs...

An Obsession

by Marcus_Cicero on Jul 30, 2019
Transgender & Crossdressers

It would have been after that documentary. The one with a feature on online dominance-submission relationships on Fetlife. Because before that moment in time life had been so vanilla. Marcus had been queer and had had a boyfriend or two... or three since turning 18. Well, hell, he'd been to the bathhouses since turning 20. He'd even gone as far as to create...