He was a college guy who wanted to experience man-to-man sex and thought an older guy would be a better first time experience. He was twenty and I was 50. It was different for me and he loved it.
One of my favorite activities is mutual masturbation. I used Craigslist as the preferred connection, and when I saw a college guy who wanted to have his first one-to-one play with an older guy. I replied and told him I was fifty and would be happy to go slowly. I enjoyed the idea of being with a younger guy. He was twenty, and I was fifty. I did not look my age and when he undressed, he was smooth. He explained that he was a swimmer and shaved the little hair he had. It was hard to miss his substantial pink balls and cock which was at least more than six inches. It was perfectly formed and pointed to the sky. He smiled, and I told him, “Mine pointed up years ago, but I am happy it gets hard and do not worry about the direction anymore. You have an impressive tool. Let’s take it easy and you let me know if you are uneasy about anything.”
We started by taking hold and slowly jerking our dicks for a while. I took out the baby oil and proceeded to oil up both of our dicks. I had him lie down, and I got on top. I aligned our dicks by holding them together, jerking the two of them together. I then let go so we were just grinding my cock against his. He said he loved the feeling; it reminded him of when he used to hump his pillow. I told him to take hold of my butt and pull me so the pressure on our dicks was even more. When it was time, I said I was close and he said he was too. I sped up, and then he let go, and we now had cum covered dicks. Then I rolled off to his smile and said it was terrific.
We cleaned up, and he was hard again. I smiled, and I told him I got soft after an orgasm, and it was clear that he stayed as large as before, just not as hard. If he takes my dick in his mouth, it will grow, and we can slowly have another orgasm, but mine might take a little bit longer. He said whatever was going to happen was fine with him since it was all new. He said going from watching things on the internet to experiencing them is so much better. I know I made the right decision to be with someone older because you took your time and did not push me to do anything in which I was not interested. I told him I am not into kissing and I do not do anything anal. There were too many potential problems with anal sex, and I was not going to fool with my health. I told them I had no desire to kiss another man, and he agreed. I told him I had no problem hugging when we were doing frottage as we just finished, but that was different. I was strictly focused on a penis and nothing more.
We stopped talking, and I started to lick the tip of his dick and then the entire shaft. He was longer and harder than any other dick that I had played with, and this was a new experience for me. Without a word, he followed everything that I did to him. He had no hesitancy to lick my balls or swirl his tongue around the tip of my dick; everything was soft and gentle with him. I was not surprised that he said he was close so quickly. I told him that I was close and that he should suck faster and not stop until I tap to shoulder. It was perfect, and holding and sucking him gave me a taste, and it was perfect for me. I waited for a reaction from him and he said this was better than he had imagined.
He said I was not sure what to expect when I met you, and from your pictures, it seemed as if we were the same size. The fact that you were smaller than me does not matter to me, and I hope it did not matter to you. You are the perfect teacher, and I enjoyed the pace with which you introduced this to me. Lying here on my back, if you look, you can see I am hard again and would love to do something to get rid of my hard-on. I took some baby oil and put it on his dick and gave him some to put on me. I told him to get on top but slide his dick under my balls. He could hump that way before we do it again dick to dick. Because he was bigger, putting his dick under my balls and humping me was a much different feeling than if I did it to him.
Of course, I did not say that to him but that was just the fact. I enjoyed the warmth of his body on mine and had no reservations about holding him. I told him to reposition his dick, so we were together and held them to adjust the position. I knew it was going to take me longer to come, but I also knew that the excitement of feeling his hard dick next to mine and his warm body on mine as I held his behind was the perfect stimulus that I needed. I was not surprised when it took me only 2 minutes more to have my third orgasm within the hour, and that was a record for me at 50 years old.
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