How It All Started for Me

This is a short story of my first experience with another man. This is not a fantasy like most of my other stories. This one is true. At least in how I remember it. If my former lover ever reads this, I would happily update with how he remembers the events.

Many years ago, when I was still in the military, I had my first experience with another man. I have always been attracted to women and prefer female companionship. I'm not attracted to men in general, though a fit, muscular bald man does makes me take another look. I don't know why.

Before my first experience, I had spent time thinking about the wonders of the male member. The different sizes, shapes, etc. I was fascinated with dick. I had also started to experiment with some ass play while pleasuring myself. I discovered I had some pleasurable sensations back there. To say I was curious would be an understatement.

This happened years ago, so I don't remember all the details. Hell, I only remember parts of those first encounters. I just feel that it's important to share what I remember.

I had started going to sci-fi conventions on the east coast with some friends and chatting with people on online bulletin boards. I made some new friends on the boards that wanted to meet up at an upcoming convention. My usual crowd from the base were not going to be able to make it, so I was on my own.

While I could buy the convention tickets and bum a ride up to the event, I couldn't afford a room. A couple of my new friends were sharing a room and said I could crash with them. One of them, we'll call him S, was openly gay. We enjoyed many conversations over time, but nothing too flirty or sexual. We just really enjoyed the same authors and enjoyed chatting with each other.

We started talking about the trip and the idea of crashing with him was offered. After the offer, he did begin to flirt a bit with me, and I happily accepted it and soaked in the attention. Besides, I was curious what it was like to be with another man. I was hoping that I could find out during this trip. I never told S that I wanted him to seduce me and take me to his bed. I was too nervous and felt some guilt about the taboo of it all. So, I secretly hoped and cautiously welcomed his advances. Realistically, it wasn't going to take much to seduce me.

When we first met in person, with others around, S did seem interested and seemed to give me some extra attention. We got along great, just like we did online. And it was welcome attention. Who doesn't appreciate being wanted? I was starting to feel like it was expected that we would be hooking up. I won't say that I was necessarily attracted to him, but more specifically what I was hoping would happen. Though he did shave his head many years later, and was always fit and muscular...

I don't remember the events of the day, and honestly most of the conventions I went to back then are blurring together. This was over 30 years ago... I just remember us getting naked and getting on the bed together.

This first night we were together was a nervous time. My first time with another man and I didn't know what to expect. We didn't have the room to ourselves, but the lady that was with us seemed to want us to hook up anyway. So she seemed to facility the new union. S made me comfortable as we just laid in bed, touched each other. At some point he blew me. That didn't take long as the excitement of it all was a lot to handle. I always remember that it was different than when women do it, but I can't really explain what is different about it.

After that, I laid on my stomach processing what had just happened. S snuggled on top of me, his cock pressed in between my butt cheeks. As we laid there, I decided I liked that feeling. I felt safe. I felt comfortable. I felt that I wanted him to take my anal virginity.

The next night we would take it further. We stripped naked and got into bed. Again, I don't remember how we got there, I just remember we were there. This time, it was just the two of us. I was laying on my back, my legs spread and my knees up. S was kneeling between my legs. I was nervous, but he assured me that all I needed to do was relax, and he would take care of the rest.

He grabbed the lube, put some on his finger, and carefully slid his finger into my virgin ass. He worked his finger around, spreading the lube. It felt good, it felt different then when I used my own fingers. He then lubed up his cock. His hard cock that was pointing at me. S leaned over me as he lined up to enter. Carefully placing the head of his dick at my backdoor, he reminded me to relax and breath.

Slowly he pushed the head in. I forced myself not to tense up as my ass received him. It didn't hurt but felt really full. After his cock head was fully inside me, he stopped and asked if I was doing OK. I nodded in acceptance, and he continued sliding his cock into me. He started slowly pumping in and out at first, still hovering over me.

After several strokes, he leaned closer to me. His rhythm was smooth and steady. He was making love to me. I just laid there and let him fuck me at his pace. The fullness of his cock in my ass turned into pleasure. It felt good. I liked it, I really liked it. Hell, I LOVED it! I was being fucked for the first time and I loved it! It just felt so good!

After a few minutes, in what felt like not enough time, his pace quickened. His thrusts were deeper. My pleasure was increasing. S made a final few hard pumps and then pushed into my ass hard and held it here as he came. And that was all it took for me. As he was unloading his cum into my ass, I was unloading mine onto my belly. We both had climaxed at the same time, something that hadn't happened to me before.

I felt incredible. I had never had a sexual experience like that, and it was wonderful. I was no longer curious, I knew that I liked it. From then on, I was hooked. Every chance we got together we fucked. I couldn't get enough of our naked bodies together and his cock in my ass. I was his to use as he pleased.

After exiting active duty, I moved down to Miami. S ended up moving down as well. We shared a room and a bed. The sex was amazing, but I was ready for a relationship. Just not with him. I still preferred the companionship of women. I loved dick, but also loved tits and pussy. But more importantly, I longed for the companionship of a woman.

Over the years after, I had many opportunities to repeat our sexual escapades, but I failed to take advantage of them. Those lost opportunities are on me. He always made himself available to me. I had no real reason not to let him fuck me many more times. I try to live my life without regret, so I won't say I regret missing those opportunities.

Over the years have lost touch with S. Again, that is on me. If I could go back, I would probably do some things differently. Spend more time with him. Maybe even officially date him for a bit. But I can't do that now. So now, I just look back at those times and those experiences with fond memories. And be happy that I had those with S.