As a masculine, girl loving young man, I had never entertained the thought of having sex with another male. 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, pretty much a daily function.
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 own cock. He suggested I should try it because it felt so good, 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 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 continued for quite some time as he stroked 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 wanted to do it again. We both got off again that morning, this time I participated by stroking his cock while he stroke me off. We had 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 participated so willingly with Billy in our mutual sexcapades during the following year; my only conclusion was that it felt so damn 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. Billy's dad was a painting contractor and had a storage shed in back of their house. We spent a lot of time in there playing with each others cock and cumming on the drop cloths. We were both attending community college at the time so we had to study 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. We would hold our cocks together, jack them and cum all over each other. Billy was able to get me off quite easily but I was never able to make him climax. He always had to finish himself off. I think he needed the extra stimulation that I provided in order to reach orgasm. 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 fantasized about experimenting with oral sex but I was too shy to pursue it. Perhaps I could have brought him to climax that way. I regret now that we didn't go further.
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 getting adequate satisfaction from the fairer sex. Billy and I both married when we returned from the service. We eventually got together and our spouses became good friends over the next few years as we visited and dined together. We never tried to get together for sex because our marital sex was taking care of our needs. In fact, 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 significant guilt about my youthful indiscretions but that has lessened as I've grown older. I now look back on those experiences with a degree of fondness and even fantasize about what could have been of we had been a little bolder.
Years later, starting in my 50's and after my divorce, I chased women for several years but eventually reached a point where attractive women were less available. My last female sex was at about age 60. During that time I incessantly thought of my previous experiences with Billy and eventually I decided to seek a male companionship again.
At age 70, after retirement, I lived in rural east Texas with a very conservative population. I was at a loss as to where and how to find a new male friend, then I discovered that Craigslist had a section for personal ads. I finally made contact with a potential partner in a nearby city that guided me through my initial encounter. He was a nice looking maried business man who was very clean cut, pleasant and well endowed. This was my first adult male sexual activity in 50 years. We first explored each other's bodies, rubbed C2C and stroked each other, then he started sucking my cock. I had received blow jobs from women before and they were excellent but he make it feel special.
I then took his member into my mouth and was thrilled at the experience. The head seemed tailor made for my mouth. It was velvety smooth, warm and throbing. I explored the head of his cock with my tongue and also massaged the frenulum. I took in as much as I could, until I gagged but I could not make myself take his cum orally although I wanted it. I finishd him by hand. We continued to meet numerous times over the next few months but I was never able to accept his cum orally, a big disappointment to me. This was the begining of a revised sex life that I have now enjoyed for the last eight years.