Gay Ladyboy Sex Experiences Stories

13,701 results
Orientation
Length
Source
Infinite Scroll

Coming Out on the Swim Team Pt. 03

by walterio on May 27, 2019
Gay Male

SUCCESSFUL SEASON The swim team was having and excellent season and that wouldn't change too soon as they had a meet with the conference last place team. It was homecoming in two weeks and among other activities there would be a swim meet against their weakest opposition. Many alumni would be in town for all the home coming festivities and athletic events....

What Would Eve Do? Ch. 02

by StiffClit on Aug 18, 2017
Gay Male

Dallas closed his cell phone and looked down at Luke who had a broad glistening grin spreading slowly across his face. Luke's lips were coated with his cream and looked delectable. Dallas squeezed the head of his cock forcing the last drops of paste to surface on its top. Luke leaned forward, his hot tongue eager to slip into the slit and lap the last drops...

Lexius Academy for Boys Ch. 02

by walterio on Sep 14, 2017
Gay Male

SHARING STORIES Brandy and Robbie were cuddled together in Brandy's bed on Saturday morning. They had had a successful start to the tennis season on Friday. The team won all five matches defeating the other school 5-0. Carl the number one singles handily won his match 6-2, 6-2. Jack the number two singles won 6-4, 6-3 and Kyle won his match 5-7, 6-4, 6-1. T...

His Best College Roommate Ever

by walterio on Aug 29, 2017
Gay Male

BEDDING CODY Cody turned out to be the best college roommate I could ever hope for. He was a handsome 20 year old who was 5'6" and weighed a trim 150 pounds. Cody was fit from all his years as a figure skater and as a result he had one of the finest asses I had ever been around. He had light brown hair that he kept neat and trim and he had light brown eyes...

First Time Bi

by ftandhubby on Sep 1, 2017
Gay Male

This is an interesting topic and I have given it a bit of thought on how to approach my experiences. I really had to think about it and actually decided that my experiences fit into two categories. First were those experiences I had as a curious youth experimenting? I'm sure many of us have had positive childhood sexual experiences with members of the same o...

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...

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...

Friend's Dad Services New Roommate

by FictionalEncounters on Jan 30, 2018
Gay Male

I just watched my friend's dad servicing my new roommate's cock... And I enjoyed every second of it. It was, without a doubt, the hottest gay experience I've had in my 7 years since opening up my sexuality to homoerotic pleasures. I have to emphasize the word "gay" in that statement because it isn't the hottest overall sexual experience I've had in my enti...

My First Time

by oralbiguy on Aug 18, 2017
Gay Male

I remember my first time quite vividly.I had never been with a guy before but had for a long time fantasized about it. Allow me to give you a little bit of background about me at the time. I had been married for about 2 yrs but my sex life with my wife was sincerely lacking. I had been going to sex shops and watching video's (gay and straight) and jerking of...

Giving It All to You

by Matureexplorer62 on Apr 1, 2020
Gay Male

Up until recently, I had never really thought about myself as bisexual, but after my thirty plus year marriage ended a few years ago, perhaps it was time to explore my sexuality a bit, maybe open myself up to some new experiences. While I have had a number of interesting experiences with several women I have met over the last few years, lately, I seem to hav...