I've posted several stories and I usually begin with "things like this never happen to me" and that's because in the past I hardly ever had hot sexual encounters with guys I've met. Only recently I realized that it was mostly my own fault because for years I was very reserve or even shy to try to approach a hot guy I've met. It's only been in recent years that I realized that I have to just go for it if I want to get lucky. Having said that, here is what recently happened to me on a trip to Florida.
I rented a cottage on the water in Key Largo which had a dock that extended out into the bay. At night you could not see the end of the dock where there were two chairs so at night I'd go out there and sit and relax. One night a lady who was renting a cabin next to me came and sat and after a somewhat long conversation said something like people could play around out here and not be seen back on the beach. I assumed she was offering and although she was quite nice looking, it was not for me. But that did get me thinking!!!
Two day later she and her family left and that night a another family checked in. This family actually occupied two units, one with a single bedroom for the parents and the other unit for their children which had two bedrooms. There were a set of twin girls I'm guessing mid teens and a son who was 21. Of course it was their son I was interested in but had no idea what he was into. In conversation with the parents I found out that he had been in college but was taking a break because he was considering military service as opposed to going back to school. They told me that he played basketball all through school and still played on a recreation team in their town. That explained his incredible physique and on top of that was damn handsome. Again, I had idea of his sexuality and/or if he'd be interested in an older guy.
One night, around midnight, I was out sitting on the dock just enjoying the quiet when I heard someone walking out and when I looked it was the 21yo. All he had on was a pair of shorts and from what I could tell no underwear as I could see his cock (which was quite big) through his shorts. He sat down and we began to chat. Turns out he was a really nice young man and we carried on a really pleasant conversation.