He took me by surprise and introduced me to new pleasures.
As a masculine, girl loving young man, I had never entertained the thought of having sex with another male. During the years when I was growing up sex between two boys was taboo. Practitioners of that forbidden activity were deeply closeted. I had a close friend for several years during high school that I hung out with along with other boys our age. We often talked about our experiences with our girlfriends and even occasionally admitted that we masturbated when necessary to relief our sexual tension.
After graduation, my friend, I'll call him Billy, had to house sit his brother’s house one night so he asked if I wanted to stay over with him. I had no qualms about his invitation since I had known him several years and we went to the same church. Additionally I had done sleepovers with other friends many times and thought nothing of it.
As we went to bed that night we shared his brother's king size bed. Our conversation naturally drifted to sex, jacking off, etc. Eventually Billy said that his brother had a vibrator in the night stand, opened the drawer, removed the vibrator and showed it to me. He asked if I wanted to try it out but I felt a little awkward about it and said no. He turned it on and started massaging his cock. He said that it really felt good and I should try it because it felt so much better than stroking my own cock. Since I was starting to firm up a little myself it seemed like a good idea to just try it, after all I may never have another chance to try one. I took the vibrator from him and rubbed it on myself for several minutes and achieved a pretty good erection. I gave it back to Billy and he eagerly resumed massaging his own cock again.
Billy asked if I wanted to use the vibrator some more and I said no. He said he was going to see how close to climax he could take himself and then stop. Eventually he turned the vibrator off and said he was quite close, he again encouraged me to see how close to climax I could get before stopping. I finally reached over, took the vibrator from his hand, turned it on and started running it up and down my still erect shaft and under the head of my cock. Eventually I turned it off and told him I was on the edge of climaxing and that I had to stop. He quietly said, "What if I did this?" as he quickly reached over and took my throbbing cock in his hand.
Let me tell you, as soon as he touched my cock, it simply exploded. I felt a massive sensation far greater than any climax I had ever experienced before as I shot cum chest high. It persisted for quite some time as he continued stroking my cock up and down, he was obviously cumming at the same time. I had several conflicting emotions running through my mind. I felt totally satiated and I was exhilarated at the intensity and the duration of the climax that I had just experienced but at the same time I felt extremely guilty at having participated in a forbidden activity. I was also embarrassed for having ejaculated in front of my friend. Needless to say, I was confused and very quiet as we cleaned up the aftermath. I returned to bed but slept very little the rest of the night. After thinking about it through the night and reliving the experience over and over in my memory, I decided what I would do.
When Billy woke up the next morning, I told him that I enjoyed our experience, that it was the most powerful climax I had ever achieved and really wanted to do it again. We both got off again multiple times that morning and we established our friendship on a new and more intimate level. We continued our new activities as often as possible, virtually whenever we had an opportunity for some privacy. You would be surprised how often and how many ways an enterprising pair of horny young men can create enough privacy to have sex with each other. I often wondered why I had been so receptive to his seduction and continued to participate so willingly with Billy in our mutual sexcapades during the following year; my only conclusion was that it felt so dam good, certainly a lot better than jerking off by myself!
We were inseparable during the following year. We both had girlfriends, but good girls didn't put out at that time. Sometimes, after double dating we drove around and jacked each other off in the car. We were both attending community college at the time so we frequently studied together several times a week and that usually led to some cock play in our rooms with the door closed.
Eventually Billy took a job cleaning a building that his brother owned. It was a small office building. Each evening Billy had to go through the building, gather up the trash, dust the offices, and vacuum the floors etc. I often helped him and after we finished, we went to a women's rest room on the top floor where there was a sofa. By then it was very late and we had the building to ourselves. We would strip off our clothes and lie down together. We would rub our cocks together and jack them together and cum all over each other. We would also place our cocks between the other's ball and thigh and dry hump each other. Interestingly enough, we never progressed beyond the mutual masturbation stage. We both seemed quite satisfied at the time so it never went further. I must admit, however, that I have fantasized incessantly over the intervening years that it would have been interesting to have explored a little further, perhaps some shared oral stimulation. I regret now that we didn't.
We eventually moved and I didn't see Billy for several years, I did not pursue any other male sexual contact during that time. I was too shy and the times were too forbidding Billy and I both married eventually. We visited occasionally but we never even talked about our shared sexual activities. Billy's work eventually took him out of state and we finally lost contact.
Initially, I carried around a little guilt about my youthful indiscretions but that has lessened as I've grown older. I now look back on those experience with a degree of fondness. I did not pursue any other male relationships until a just a couple of years ago after I was divorced and had no sexual outlet other than masturbation. I am not quite as shy now and the internet made it much easier to make seek out partners.