Gay Ladyboy Sex Experiences Stories

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A Memorable First

by pdxjo on Sep 14, 2017
Gay Male

Looking back on it now, it's hard to believe that age 27 I had never been fucked by another man. As a kid I'd had the usual sexual experiences with neighborhood boys but it never progressed any further than jacking each other off, or maybe licking another boy's maturing prick. In high school sex with girls was the goal of all the guys. Even so, the sex play...

New Neighbors Move In

by literalvirgin on Aug 30, 2017
Gay Male

First, let me start by laying down a little bit of my background. My name is Joe. I am 6’3”, 220 lbs, brown hair and blue eyes. I am married and consider myself straight. I have had a few homosexual experiences in the past, but they were with my best friend who is a long distance truck driver. My previous gay experiences were monogamous with my friend and ar...

Then Ch. 02

by ssvt1138 on Sep 14, 2017
Gay Male

Since I have already began to tell about my past, I guess I should continue to tell the story. Especially since I have now set out to relieve some of these experiences. Thinking back, I now realize that the early eighties were a bit like the old wild west: No rules. I did these things just before anyone had heard of AIDS, so today I would never dream of unpr...

Can't Call Me Straight Anymore

by straighttobottom on Aug 24, 2020
Gay Male

This is a true account of my first gay experience last year. I was 34 years old at the time, I am happily married with a great sex life. Have always been a masculine guy 6' tall, 180 lbs with a shaved head, blue eyes, blonde beard, and in good shape that can honestly say had never once been interested or even curious about being with guys. As a consultant,...

Early Slut Training

by August74 on Jul 15, 2020
Gay Male

As I get older and wiser, I realize that I lead a very stable and normal life. Married with two sons and five grandchildren, life is fine but somehow I feel bored. The bottom line is that when I was young and single, I experimented with gay sex. I told myself that it was a passing fad and for the most part it was. And yet after all these years I still think...

My First Experience with a Man

by JayDeviant on May 23, 2018
Gay Male

So, this is a true story. Honestly, I'm not just saying that. I was in my early 20's when this happened, and whereas I share many of the same character traits now as I did then, it cannot be emphasized enough just how trusting and innocent I was back then, much more so than today. In fact, it has only been in recent years that I've been able to revisit this...

Bathhouse Heaven Ch. 08

by glory_first on Sep 14, 2017
Gay Male

Some things provide such a reliable sensation that in essence, I have been addicted since experiencing them the first time. Particularly in the cases of poppers with my first girlfriend decades ago, or discovering the pleasures of the baths in one glorious evening. Visitors to a male only sauna often enter a type of paradise undreamed of before experiencing...

First Time Fling

by CrimsonClown on Sep 14, 2017
Gay Male

For a fifty year old he aged well and soon enough after months of flirting over social media, and skyping, he'd invited me on a date to meet up with each other. I was only twenty one but at his age, Hank had managed to talk his way in to many meets ups with me online that transformed in to meets ups face to face. He was a sly and very charming man who made m...

Married Guy New Experience Ch. 01

by Marriedandneedingmore on Sep 19, 2017
Gay Male

This is first story to be submitted, I welcome any suggestions, comments, feedback, etc on either story, format, or anything else. If anyone would like me to go on please say so. ***** I'm a normal married guy, in my 50's, married 25 years where the sex becomes mundane and predictable, eventually less and less and finally to none at all. That's the way our...

The Ceilidh

by hamishmcl on Aug 18, 2017
Gay Male

I was driving round Scotland together with my friend Ken who was visiting from NZ. We were staying in a B&B in a village near Perth. Down the road the 'Big Hotel' was advertising a ceilidh, open to non residents. The cover charge seemed reasonable and Ken was fanatical about country dancing so we just had to go. The billing suggested that it would be smart...