Before I gave my first blowjob, I'd had a few experiences with guys, where I played with one guy's cock for a while before he stroked me off and another instance where I sucked a guy for a little while before he got me off. In both cases the guys seemed more satisfied than I was. But I never got the chance to pursue taking another guy's load. However, one ni...
My first experience with a glory hole occurred in Kansas City when I was 23. My wife was pregnant and just about due with our first child. Needless to say I wasn't getting any at home but was not comfortable finding a playmate for a few weeks. I didn't feel right about asking her to jack me off or give me head. I think she probably hated the idea of sex at t...
The news was unexpected. I can't say it was devastating. In fact, it elicited no truly emotional response from me whatsoever. But just a few months ago I was scrolling through my Twitter feed and a headline jumped out: "Yahoo Chat to shut down permanently." I paused for a moment when I read that headline. Yahoo Chat. It had been probably ten years since I,...
This is my fourth letter describing my expanding awareness from a naive man with a desire to suck a cock to a man willing to explore his seedier side. In my first letter "Costume in a Costume" I describe how I dressed as a girl in a Halloween costume to trick unsuspecting men into letting me give them my first blow job. In my second letter "Gloryhole Illust...
I can say this true story started harmlessly enough. I was a young up and coming 18-year-old swimmer and between training and school, didn't have much time for anything else. I enjoyed girls, and they enjoyed me but the training and school took its toll on my social life. At the time, one of my coaches, Mike, lived in this great condo complex near the pool....
I tried to shift up to my knees, but my hands were cuffed tight behind my back and my feet were bound. I looked up at the master and he repeated his command, "get up on your knees whore" I tried again and this time rolled up onto my shoulders than my knees. I struggled but managed to pull myself up. I stared at him with naive optimism that he would be pl...
Prequel I arrived at college a naive and sheltered kid. Eight years of Catholic grammar school in the 'burbs of the Connecticut shore followed by a Catholic all boys' high school never prepared me for being on my own. A Catholic college seemed like a logical place. Close to home but far enough away that I lived on campus. It was 1979 when I moved in the New...
My first experience with another guy was many years ago, when I was eighteen. I had left my parents home and had rented a small flat from an older guy while I looked around for a job. Bert was in his early forties, quite good-looking and fairly muscular for his age. I, on the other hand, was tall and quite thin, as I hadn’t started to fill out yet and I gues...
My name is Robert and I am now married to Ania, who I have written true stories about, but this story is about my first gay experience. While I was living in the West Country I learnt massage as a second income to my small business that I was running. It only took few lessons to learn massage and as I am sure you realise it good fun. Touching ladies and havi...
Briefly this is me, I'm 24, 5'5" and 126lbs. My hair is long dark brown and my complexion is natural tan from my native heritage. I've been a crossdresser ever since I was born. Period. Now that I live on my own I have all sorts of outfits, makeups, shoes, breast forms and toys. I just have one thing I have never done. I've never been with a man. I've fa...