Gay Ladyboy Stories

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The Training of a Ladyboy

by dreamweaver5539 on Sep 14, 2017
Gay Male

I met a wonderful couple at a resort recently, Chantal and Dave. We hit it off splendidly and were soon spending our evenings together at the poolside bar. By disclosing the nature of my own infidelities (which was fairly obvious through my hitting on their hunkish friends!) I earned Chantal's trust and she disclosed to me the nature of their own very intere...

The Real Thing This Time

by hornyrider on Aug 18, 2017
Gay Male

Readers of my story 'My First Ladyboy' will know that I was spending a lot of time in the Far East monitoring the activities of my company's agents from our London base. The initiative proved highly successful and it came as no surprise when it was decided to establish a small office within the region and I was asked to set it up. I was instructed to make...

A Teen Seduced and Hooked on Anal Ch. 10

by walterio on Aug 12, 2019
Gay Male

SATURDAY MORNING FILMING Bruce the director met with the three actors. Eric, a beautiful blonde Carrie and the pretty ladyboy Carla. He explained that neither Eric or Carrie were to know that Carla had a dick so they were to act surprised when they saw it. They had met at a club and Eric had invited them back to his place. Bruce asked Eric a special favor....

They Become More Than Cousins Ch. 04

by walterio on Aug 31, 2017
Gay Male

AUTHOR'S NOTE: I had not intended to write a series or a sequel to this story at the time that I submitted it. However based on the comments that I received encouraging me to continue this story, I have decided to write another chapter. If that is well received then I will continue with these characters. Thank you for the positive feedback. ***** SCOTT MEE...

Hangout with Harry Pt. 02

by periergos on Aug 18, 2017
Gay Male

** Hi - Many thanks for clicking - I hope you enjoy my humble efforts. I'm really interested in any comments or feedback - please let me know your thoughts! I'm also looking for someone who could assist with editing and other bits prior to publishing - feel free to get in touch. Do let me know if there's interest in this story continuing. There are a coupl...

Romeo, Where Art Thou Going in Life? Ch. 03

by walterio on Sep 14, 2017
Gay Male

ROMEO ACCEPTS MARCEL'S OFFER Romeo slept at the salon the night that he had been evicted form his home. He knew that he had no chance to go back home as his father would never let him return. The next morning Romeo freshened up at the salon and then headed to the barber school. He would return later that day to work at the salon and by then he hoped that he...

The Bottom Tier: Ari and Cato

by Cruel2BKind on Sep 1, 2017
Gay Male

*Oh my god! This is the last chapter of the Bottom Tier, and Jesus it's really taken it out of me. I stayed up till four in the morning to finish this one. -_-' The Bottom Tier has always been one of my favorite worlds to play with, my darkest invention. I think I should stop playing with fire, and I will be truly amazed if this chapter makes it past the ed...

The Bottom Tier

by Cruel2BKind on Sep 1, 2017
Gay Male

*Hi readers! All characters are 18+ the part in the beginning is only a flashback. This story is slightly confused, but I think it belongs in Gay Male because though my main Character, Kip, has some elements of the feminine persuasion, he still identifies as Male, and all of the sexual encounters in this story are basically gay encounters with some unusual...

The Booth Ch. 1

by C_Duke on Sep 2, 2017
Gay Male

I don't see any shame in admitting bisexuality. The truth of the matter is, I find women attractive, and sex with them highly pleasurable. In fact I'm thinking about them and it most of the time, like most guys. But recently, and essentially through my exposure to more, harder and more varied porn I started to wonder. And then I started to really think ... a...

The Long Trip

by TheBlackStallion on Mar 6, 2018
Gay Male

Editor's note: this story contains scenes of non-consentual or reluctant sex. This is my first story, please give me some feedback. Parts of this story of true, some of it isn't. I'll leave you to decide * I've been a young sailor for almost two years now. We've been at sea for almost 75 days. Tomorrow we will be pulling into Thailand. It's been a long ri...