I had a male jack-off friend as an upper teen but eventually married and had a family. Somewhere down the line the home sex began to play out and I reverted to frequent masturbation to satisfy my sexual needs. Eventually I was divorced and my fantasies started returning to my boyhood experiences. The more I thought of it, the more I wanted to try an adult male sexual experience to see if that would fulfill my sexual desires.
Here I was, a 68 year old male with absolutely no idea as to how to find a male companion or how to initiate a sexual relationship with a man. I decided to begin a little research on the internet to see if personal ads were available in my area. Incidentally, I live in a rural area that is socially conservative so I felt that I needed to be rather cautious in my search.
Initially I was impressed with the number of ads posted for my area but there was a shortage of men in my age group. I read numerous articles regarding placing ads, responding to ads and making discreet initial contacts. I placed several ads over several months looking for a "Jack Off Buddy" for a senior beginner. I received quite a few responses but they were disappointing, primarily because of age and they were wanting significantly more intense activity than I was looking for.
During this time I was also combing through the daily ads looking for someone that might be a good prospect with whom I could begin at a comfortable level. I responded to several ads but had little luck. Again, most wanted a lot more that I was wanting to give. I even had several "no shows" which were rather disappointing. Numerous respondents were married and could not host nor get away long enough to play.
Eventually I saw an ad from a man of similar age that seemed to be a reasonable possibility. He was a semi-retired man of similar educational background whose wife was no longer interested in sex. He too had some prior youthful indiscretions and was looking for discreet, safe sexual gratification with no strings attached. He was located in a larger town about 40 miles away. Since he was semi-retired, he maintained a small private office where we could meet.
After a number of emails we decided to meet just to get acquainted. As I was preparing to drive over to meet for the first time I was extremely nervous. Unfortunately, I had plenty of time to get more nervous as I drove to town. I was, in fact, a nervous wreck by the time I drove up to his office. I was pleased to see that he was very clean cut, similar in size to me and very easy going and friendly.
After talking in depth for a while we decided to go ahead right then and there and have a go with each other since he had no other appointments coming to his office. He locked his door and we began undressing. He had a sofa in his office where we sat and began to caress each others nakedness. He was well hung, an inch or so longer than my 6 inches, We were both uncut and similar in thickness. I reached for his cock, the first one I had felt in almost 50 years and it was good, so smooth, firm, warm and throbbing. He grasped my cock as we reclined beside each other. His touch was like magic and I knew that this was what I had been looking for.
We placed our cocks together and slowly rubbed them together, the feeling was sensational but the best was yet to come. He turned to the 69 position. I had only wanted to masturbate with him but when faced with his cock I felt compelled to take him orally as he sucked my cock into his mouth. I had never had a cock into my mouth and was surprised at how natural his head felt in the roof of my mouth, it fitted perfectly. The taste and feel were so smooth against my moist lips.
Meanwhile the sensations I was feeling in my cock were fantastic. Although it had only been a few minutes, I was quickly losing control. I told him that I was about to cum if he did not stop. He did not stop. I erupted with a massive climax ejaculating into his mouth as he skillfully applied suction and up and down motion on my shaft with his lips and tongue. It was better than any pussy I had previously experienced.
I continued sucking him but could not bring myself to take his cum orally. I told him I would have to get him close and finish him by hand. I finally got him off with his cum shooting over his stomach and chest. I explained that, due to my lack of experience, I felt reluctant to take his cum orally but wanted to learn to eventually learn to take it and swallow it. He agreed that we could start working on that at our next meeting. My only regret was that I had waited so long before seeking male sex.