My First Encounter With Gayness

I’m a 33 year old, single, Bi-sexual male. But I’ve only had sex with one man in my life and that was when I was 18. The relationship only lasted for a couple of months before he decided to end it. He was a 49 year old, married man with balding hair and a full beard. He had 2 grown children ages 21 and 25 who were living in Boston. He owned an antique store on LI, and his wife worked in the city.

I used to go bike riding a lot during the summer months. I often rode my bike the 10 miles down to the harbor to watch the boats. Lots of people liked to take lunch by the water as well.

One day I passed by a man sitting in a red convertible. I didn’t say anything to him as I passed by his parked car and stopped at a bench about 40 ft behind him. As I watched the boats, I noticed him looking at me through his rear view mirror. I stayed for about 10 min, resting up for the return trip.

As I walked the bike past his car, he said, “Hello.” Then added, “Kind of hot to be bike riding isn’t it?”

I returned his greeting and told him that I actually enjoyed it more when it was hot out.

During this exchange, I didn’t break stride while walking the bike past him, and I planned to continue on my way. However he continued the conversation by asking me how often I rode my bike this way.

Not wanting to be impolite, I stopped and approached his car. We then talked for a few minutes about biking. He told me he and his wife used to ride, but hadn’t for a few years.

When I finally told him that I had better get going, he asked again how often I rode my bike down to the water. I told him that I usually rode down about 2 times a week. He then said his goodbyes and said that it had been nice talking to me and I said the same to him had spun off on my way home.

About 5 or 6 days later, I again rode my bike down to the water. I hadn’t given any thought to my initial encounter with this man in the red convertible, and had entirely forgotten about him. It wasn’t until I saw his red convertible in the same location that I remembered our earlier conversation.

This time I didn’t walk the bike up next to his car, and instead stopped about 200 ft in front of his car. After a few minutes, I heard his car engine start up, and he drove up and parked right next to me. After greeting me, he asked me if I remembered that we had talked earlier.

Then he continued asking me a few more questions about bike riding. It was at this point, that he made the first of what I felt were obvious sexual advances towards me. He said bike riding was doing me good, and that he really liked my long muscular legs.

When he told me this, I immediately became very uncomfortable. Surprised and slightly confused by his comments about me, I just said thanks and started to move slightly away from him.

He then told me that he lived near by and that he had a nice built-in pool. When he asked me if I wanted to come over for a swim, I definitely knew that he was up to something, and I politely refused his offer.

As I started riding back home, he followed behind me for a short while, still trying to make conversation. After a few minutes of this, we finally parted company.

I knew that this guy was after something, and I didn’t plan on going back to the water for quite a while, or perhaps ever again. However something happened to change that. After a day or so, I found myself thinking about him. When I was 18 I was masturbating quite a lot.

Now suddenly after our second meeting, bearded men started appearing in my masturbation fantasies. I started fantasizing about what he wanted to do to me, about what would actually have happened if I had gone swimming in his pool.

The more thought about it, the more aroused I became. I tried hard to resist these thoughts but I just couldn’t. At 18 guys are very receptive to anything sexual, and this man seemed to send out sexual vibes. It was forbidden territory, something that I’d never thought about before.

It only took about 2 weeks before I found myself back on the road to the harbor again. As I approached the water, I felt my cock getting hard. Part of me was hoping that I wouldn’t see his red car there.

However, it was parked in its usual place. This time I rode right up to him. After a few minutes of casual conversation, I asked him about his swimming pool. I was very nervous, but also very excited.

He smiled at me and suggested that I come home with him and try it out. I secured my bike at the bike stand along side the harbor road and got into his car.

He only lived about 5 minutes away, so we quickly arrived at his house. As we went through the garage, he showed me his bike and suggested that we go biking together some time. Once inside we went into the living room and he offered me a soft drink.

We sat at opposite ends of his couch and again started talking. For the first time he asked me how old I was. I told him that I was 18 and was about to start my first year of college that fall.

As we talked, I was constantly thinking about how to initiate something sexual with him. It wasn’t really a conscious thing; it just seemed to be a need I had. I started worrying that perhaps he was just being nice and didn’t really want anything sexual from me.

I was also worried about my hard on, surely he would notice it if we went swimming. My cock was fully erect in my shorts as we talked. I figured that since I was much younger than him, he was probably reluctant to make the first move.

Finally I asked, “So you said you liked my legs, huh?”

He smiled and said, “Yes, long and muscular.”

I told him that I really liked his beard, and that I’d prefer to have thicker legs like his. Then a little nervously I got up and sat right down next to him. Being so close, he now clearly saw my bulge. He looked at it for a few seconds, then put his hand on it. Then without another word, he started gently rubbing and patting my bulge through my bike shorts.

I just sat there and let him do this to me for a while. When it became obvious that I was getting pretty hot, he stopped and asked me if I wanted to go upstairs. My legs were literally shaking as we climbed the stairs and walked towards his bedroom. I literally felt an electric charge run thru me when he closed the bedroom door behind us, fully realizing that I was about to have some kind of sex with him.

We stopped at the foot of the bed and we hugged for a while. Then he gently removed my shirt and shorts. He asked me if I wanted to explore his body. When I said yes, he pulled of his T-shirt and unzipped his pants.

I could clearly saw the huge bulge fully outlined in his jockey shorts. I reached down and cupped his balls thru his shorts and was amazed at how heavy they felt. I watched as he removed his shorts and his cock fell out fully erect.

He sat down on the edge of the bed and watched as I removed my underwear. I sat down right next to him and grasped his fully erect cock and began examining it. It was uncut, about 9 inches and very thick. I had never seen an uncut cock before and was amazed at how different it was.

I masturbated him for several minutes, before he asked me if I wanted to do “more” to him. I just nodded and he stood up, moved some pillows before lying down fully on the bed. He then told me that I could do anything I wanted to him.

Not knowing really what he meant I touched and fondled his cock some more, ran my hands all over his legs, stomach and chest. I touched and gently pulled on his beard, massaged his balls, rubbed his nipples. I still remember how he simply laid there, letting me do all this to him.

Suddenly, I got the urge to get on top of him. So I simply climbed on top and began rubbing by body against his. He put his hands on by ass as I rubbed against him. I this position we were face to face, and I began kissing him and rubbing my face against his beard. We also seemed to rub noses quite a lot.

However, rubbing against him like this was making me too aroused. I was moving against him very fast, and he told me several times to slow down. Finally he actually stopped me entirely and told me to calm down. He said to relax and to take deep breaths.

After a bit I resumed at a much slower pace. However, this didn’t last long. The simple fact that I was having sex with an older married man in his own bed, and the feel of his hands on my back and ass was just too much for me. I again began moving very fast against him.

It wasn’t long before I could feel my orgasm building. I didn’t want to stop it. I remember actually saying sorry to him when I started cumming. He told me not to worry about it and to just enjoy the feeling. I did enjoy it, it gave me such a feeling of freedom, and his skin against mine felt like it was on fire.

After my orgasm I again apologized to him, telling him that I couldn’t help myself and that I was just too excited. He assured me that he understood and that I would certainly last longer next time.

Then I moved down and began masturbating him. I don’t know why I did it but began sucking his cock just like the women in the few x-rated videos I had seen. I must have been doing a good job judging by his moans and facial expressions. I was able to get him off, and I was surprised at how much more spunk his cock produced compared to mine. I made every effort to swallow everything he had.


Afterwards we talked about what we had done, and he asked me if I wanted to do it again later. We then went swimming for a few hours before going back to bed. Again I climbed on top of him just like before. This time I lasted much longer despite still being very aroused by the whole situation. Finally he told me that his wife would be getting home soon. After he drove me back to my bike, he told me to come over again tomorrow anytime after 8:00am. He told me that his wife worked in the city and left every morning around 8:00am, arriving home around 6:00 pm.

The next morning I rode my bike straight to his house around 9:00am. We then went straight to bed. However, this time he told me that he was going to do something different to me while on top of him. He began rubbing the underside of my cock with his middle finger using a circular motion. I simply loved the sensations this maneuver produced. I found that I couldn’t really move against him while he did this. I had to simply lay still while he masturbated me in this fashion. However, I was still able to kiss and rub noses while he did this.

What was so good about this maneuver was his ability to control my arousal. He told me to take deep breaths and to just let him rub me to orgasm. Whenever I moved, he would stop. He could tell by my facial expressions and by my breathing when I was getting too close. He taught me how me to fight off ejaculation by always breathing deeply in a slow deliberate fashion. He was absolutely right. With practice, I was eventually able to experience multiple orgasms without ejaculation. He lectured me constantly about resisting the urge to ejaculate.

Sometimes I managed to hold off my ejaculation for up to 40 min, while experiencing countless orgasms. However, despite learning to last quite a while, he always seemed to get annoyed whenever I finally ejaculated. He always felt that I could have lasted longer. Of course many times he was absolutely right. I couldn’t help it, I liked ejaculating. Sometimes after 20, or so minutes, I was simply ready to experience that special feeling of ejaculation. Other times I just could stop ejaculation no matter how hard I tried. He mostly didn’t like it when I told him I was going to end it by letting myself ejaculate.

After a few days, he started asking me how I felt about anal sex. I had never done it, so I told him I didn’t really know. It took him several more days before I finally allowed him to have anal sex with me. He assured me that he would be gentle and go very slowly.

I helped him rub Vaseline all over his cock. He then positioned me over some pillows and he initiated me doggy fashion. I remember feeling his hands on my hips, but he was having trouble getting in. I was very tight, and it took him quite a while to open me up. However he going very slowly and he constantly asked if I was feeling any pain. He told me that there might be a little pain, but if it ever got too much to let him know immediately. Then suddenly after several min, his cock just slipped right into me. We both gasped at the suddenness of his cock sliding almost completely in.

He then proceeded to fuck me using a slow deliberate rhythm. There’s wasn’t any pain, and it felt very good. I could watch him thanks to a large mirrored closet opposite the bed. I saw by his facial expressions that it felt good inside me. He moaned quite a bit and it added to my arousal. He kept up his slow rhythm for several min before he finally lost control. He suddenly began humping faster and faster before he spasmed and laid completely on top of me. I could feel his hot cum squirting up inside me.

We had sex around 4 times a week during that summer. His wife’s side of the bed was often still warm when I got into it, and I could often smell her scent in the room, which added to my arousal. I always rode on top of him, and he fucked me whenever I let him. I always gave him head, yet he hardly ever sucked me.

Although he was probably being very selfish in bed, I really did enjoy riding on top of him, and I really enjoyed sucking him off. After a while he began to get concerned about being caught. Also, every fall, he always took over the Boston store, and wouldn’t be around anymore.

I started college, and we never got together again. I still relive our sexual relationship when masturbating.