Experiences of a Late Starter Ch. 01

In the following chapters, I describe my first adventures with men. Maybe some of you will recognize the experiences and feelings. It is an account of what happened during the last half year, including a few disappointments.

I am 60 years old, married and grandfather. My wife and I had a good sex life till about 5 years ago. Since then she is hardly interested in sex. Even when we still had sex, I used to masturbate from time to time. In the last few years this has become an almost daily habit again, just like it was when I was a young guy.

During many years when I watched porn I always liked to watch women getting butt fucked doggy style. My wife never let me fuck her ass. A few years ago I realized that I actually wanted to be the one being penetrated. This feeling became stronger every day.

I had been using anal toys when I was about twenty-five years old but stopped with that as I married. But a few years ago, I again began using butt plugs and a dildo, usually when my wife was out. The first time I was very embarrassed to enter the sex shop but the seller did not seem to be surprised to see me, despite my gray hair. I started with a modest size butt plug but soon returned to the sex shop and got the bigger stuff.

I liked to fuck myself with the dildo, but usually I did not reach an orgasm by doing so. It is just the feeling of penetration that I liked so much. The largest butt plug I used only got inside after I sat on it for half an hour, relaxing my ass and gently pushing on it. When it was finally inside me, it was an incredible feeling. I liked to walk up and down the stairs with the plug massaging my ass as I walked. The problem is that playing with the toys only made me hornier and longing for a real cock.

Last year, I decided that I had to have the real thing. I was now 60 years old, and waiting any longer would mean that I would never have it. When I go to the gym and shower, I like to be naked among other men, but it is not easy to find a partner there.

I checked for a gay dating website and placed a short text that I was looking for a man to fuck me. Soon I got a response from a guy who was interested to do it. We made an appointment.

He arrived in his car after I had been waiting for half an hour. He was much younger, about thirty years old. I had expected to have this meeting in his apartment or someplace like that, totally nude. But he was married and had no place available. He said he knew lots of places in the area where we could do it in the open air. As we drove around to look for a quiet place, it was clear that he had not expected to meet such an old man like me anxious to get his first fuck. He told me that he would be gentle with me.

He stopped the car at the end of a road not far from a farm. He asked if I wanted to suck his cock. I would like to suck and swallow but some other time but not today. So we had no oral sex. There was no foreplay at all; I was not really interested in it anyway. I was so horny and nervous at the same time that I just wanted him to fuck me.

It was summer and nice weather. We found some bushes to stand behind and he opened his pants. I felt his cock. It was not very big to my regret but stood very hard. It was the first time I felt another man's cock. He said, "Let me see this ass of yours." I have rather a big butt. Without hesitation, I dropped my pants. I had told him that I wanted to be fucked doggy style so he had me bend over. I gave him the condom and put lube on my ass.

He held my ass cheeks with both hands and stuck his cock in me. His promise to be gentile with me was forgotten. He fucked me fast and pushed me forward deeply. I almost fell so I had to hold the ground while he was pounding me. I wanted it harder and was bucking my ass, milking him. I felt like a whore. Here I was standing, a married man, bent over in the open air, offering my ass to a guy whose real name I did not even know!

You may understand how strange this was, how nervous I was but also how horny I must have been to do this. He finished very fast and shot his load in my ass. A few seconds later we heard voices. A woman and child came along on their bicycles. I don't believe they saw us behind the bushes. Anyhow, I pulled my pants up very fast, it was a bit of an anti-climax. I believe I saw him throw away the condom. He asked for a tissue, he did not bring anything at all. Later, I thought it strange that I had to bring the condom, lube and cleaning tissue.

He asked if I did not want to cum, but this time, I really only wanted to be a bottom, just fucked hard and deep. I did not have an erection; I was too nervous. Being naked for a strange guy, offering my ass was enough. As we returned to his car he began asking where I worked and all kinds of questions like that. When I posed him similar questions, he evaded straight answers and clearly was lying.

He took me back to the crossroad where we had met and we went our separate ways. Traveling home, I was in some kind of shock. Did I really do this? Drop my pants and bend over for a man to fuck me? But I was also very excited. I finally did it! I could feel the lube still seeping from my ass and that gave me such a feeling of being fucked. However, I did not like the way we had done it. It had been such a short meeting. For several weeks I was happy that I fulfilled my desire to get fucked because I no longer felt this frustration that I had had for a long time. Even my wife felt that I was more relaxed and happier. Of course I could never tell her how that had happened.

Later I started worrying. Did he really put on the condom? I did not check him. I made an appointment for an HIV test and had to wait two weeks. I did the test at a private clinic and got the answer after fifteen minutes. Everything was OK. The doctor was very friendly. I assume he is gay because he gave me all kinds of advice on meeting gay men. When I told him that I was so afraid of STDs that I considered giving up sex with men, he smiled and said: "Why give up sex?"

But these two weeks I had been very worried and I decided not to do it again. I realized that the risk of being exposed and my family might find out was too high.

Encounter two...

Although I had decided not to do it again, after a few months the longing for cock returned.

I found another dating website. On these websites people hide their identity; they give a false name, age, profession everything. Several times I almost had a date but very often the men were imposters, just interested to have a horny chat and then suddenly disappeared. Especially many young men are totally unreliable at these sites. They want sex now and expect you to jump in your car right away.

None of them is interested in a date tomorrow or next week. Older men are better partners in this aspect.

A man aged sixty-seven sent me a message. He wrote that he did not do anal sex but promised "lots of other things". His favorite book was Fifty Shades of Gray and this made me curious to meet him. I met him late in the afternoon outside his office. The man was a much respected and married lawyer. I was surprised to see him. I had visited him a few years ago for a legal matter, but obviously he did not remember me. We chatted for ten minutes in his car. I told him that I had little experience and was willing to learn new things.

He asked me if I had ever sucked cock. When I told him that I would like to do that, he put his hand on my knee and invited me to his office. The office building was empty and very quiet. The air conditioning was switched off and it was very warm inside. His office had a large room with a huge desk, expensive furniture and lots of impressive law books everywhere. We undressed and he brought me to the office kitchen to clean myself. Then he embraced me, and started kissing me with a lot of force. I was not really expecting this but he pushed his tongue into my mouth. I tried to enjoy it but it was not easy.

His mustache was hard on my lips. Then he began pulling my nipples and twisting them till it hurt me. I placed my hand on his cock and felt how hard he was. I knelt down on my knees and put his cock into my mouth. It was a very strange feeling. His cock head was big and as I started sucking I had a few times a gag reflex. But the idea that I finally sucked cock turned me on! He did not cum. He spread paper on his desk and had me sit on it. Then he sucked me, it felt good but I did not particularly care about it.

While he was playing with my ass he slapped his hand on my buttocks. As he noticed that I liked that he asked if I would like him to spank me. That was part of fifty shades of gray, I suppose. He said that he sometimes uses whips on partners who go home with red backs. I was not interested in that level of spanking but I bent over for him and he slapped my ass. It felt so good. Then he had me lie on his lap while my hands were touching the floor. He spread my buttocks and checked my asshole. He began slapping my shaking buttocks harder and harder. It did not really hurt. After an hour or so, we stopped and I went home. Traveling home, I still had the strong taste of soap and aftershave in my mouth. I showered for a long time to get rid of the smell.

Encounter three...

One morning while I was working, a man sent me a message and asked me to call him. He invited me to his home. His wife was gone for the day. I told him in advance that I would not suck him without a condom and that I was only looking for anal penetration. He agreed. I left my work and took a cab to his house. After a few minutes of small talk, he said: "Let's go to the bedroom." We undressed and as soon as I was on the bed he embraced me very tight, kissed me, and pulled my nipples very hard. He wanted me to suck him but I did not agree. He sucked me a bit, I hold his cock in my hand for a few minutes. Then he began masturbating, playing with my ass, pushing three fingers inside.

He reached an orgasm and immediately left for the bathroom to clean himself. As he returned after a minute it was clear that he expected me to leave. I found a cab and as we drove back to my work, I realized how short these sex meetings were. I also understood that "anal penetration" could also mean pushing three fingers inside. If I wanted to get fucked, I should make that very clear. I was back at work within an hour. I have no problem leaving my work for a few hours; I just have to stay later afterward.

Encounter four...

I had several canceled dates. Many of the visitors of these dating sites are men having fantasies and are probably jacking off while chatting. I guess that as soon as they shoot their load, they leave the website. Others are too afraid to meet you because they are married. The most serious men are men who are definitely gay. They know what they want and there is less chance that they cancel at the last minute as many bi-curious guys do. The next man had a nice picture on his profile; he was a middle-aged, openly gay top. As I reached his apartment building he opened the door, dressed only in his briefs. He was a fat guy, not as handsome as his picture. His apartment was in the basement of the building, almost without windows. There was hardly any furniture. Next to his unmade bed was a washing machine. A small ventilator stood on a chair.

Obviously, he was also disappointed with me for he at once said, "You are not my type, I am sorry." But since I was already there, he said, "We can start with sucking cock and will see how we continue."

That was probably the first time that I met an honest guy. We undressed within minutes and I sucked him with a condom. He had a very small cock, I could easily have him.

While I was giving him a blow job, he played with my ass and said, "My cock is huge, isn't it?" I moaned affirmatively, of course, I did not want to disappoint him. He reached his orgasm quite fast. That was my first successful blowjob. I had no erection at all. As I left his apartment I checked my cell phone, I had been there less than twenty minutes.

Encounter five...

The next meeting was with a younger man, called Roy, about thirty years old. He invited me to meet me first over a cup of coffee. We met in a mall and had a long talk. He was a software engineer, and only his family knew that he was gay. Roy was a very gentle young man. He explained that he had been for a few years in a monogamous relationship with a steady partner, as he called it. But then his partner wanted sex with other men and they stopped having sex together. They still have dates but without sex. Now Roy also was looking for a man. He described himself as a top. This first meeting of almost two hours was a good start.

After a week we met again, in his apartment this time, at ten o'clock in the morning. He was sharing the apartment with a girl, a music student who knew that he was gay. She was not there. After half an hour of talking, we went to his bedroom and undressed. He was built smaller than me, with a very hairy but small chest. Again the first stage was kissing, French kissing and then nipple sucking. My insistence on using condoms also during oral sex probably deterred him.

We were kissing. I did not like the hard stubs of his mustache. Why do men keep this facial hair? When I finally reached the stage of fucking, he put on a condom and we started missionary style. I felt him enter me half an inch, it was a good start but then his cock lost power. He kept trying but it was a failure. I turned over and offered him my ass but he could not or would not enter me.

The apartment was without air conditioning, there was a July heat wave and Roy was dripping sweat like a horse. When I left his apartment he apologized. We did not see each other again.

After that meeting, I came to the conclusion that sex with men is not for me. I don't like the kissing, especially the facial hair, I don't see the fun of sucking the nipple of a guy. I don't mind sucking cock and it is a horny experience but I will do it only with a rubber. All of the men say they are clean, that they don't "fool around without everybody", but in all cases we were having sex within minutes without even knowing each other's names. If that is not fooling around with anybody, what is it? Only Roy knew about the risk of oral sex and STDs. None of them ever use condoms while sucking cock.

That night I deleted my profiles from several gay dating sites and decided to be straight from now on. But that idea lasted only for two weeks. Soon I got what I wanted. Next time I will tell how that happened.