My First Time with a Man

This is my first try at writing a story, so I will start at the real beginning of my journey...

All my life I have been attracted to men. I love women and have only been interested in dating them, but something about a man's body has always appealed to me as well. In particular I have always loved cock. The look, the feel, the taste of it has always turned me on. I also think it is the raw sexuality of being with a man. I have always preferred when sex with a woman had an emotional investment. I've never really pursued a one night stand. But on the other hand, I have also been turned on by the idea of meeting up with someone just for the purpose of sex. I know this is a paradox, but I have always been of a split mind, part very romantic, and part unabashedly dirty. Something about 2 men being together with no purpose of romance, but just to get each other off is one of the hottest things I can imagine.

I had played around with one of my best friends growing up, but when I went off to college I had no real sexual experience except for the typical 2-3 times a day I had very intimate experiences with myself (I was definitely what you would call a chronic masturbator). But once I moved away to college, I looked to expand my horizons. I am in my 40's now, so this would have been right around when the internet was really getting going. When I got my first internet connection not long before I graduated high school, I quickly discovered the copious amounts of porn available (even back then). Not long after I was away from home I also discovered sites that helped men meet one another. As a shy guy who had neither the nerve, or the know-how, to meet men in person, this was perfect for me. Also, I was not as interested in a guy my age. I had always fantasized about older men, and this was what I was looking for. The thought of a grown man helping me to learn was something that had always made my dick rock hard.

At first, I was really only interested in finding a jack-off buddy. I badly wanted to be sucked, and wanted to suck, but was not really ready for that yet. I found a gay chat room that allowed me to talk to many men, but I never quite found a situation I was comfortable with. I was in dorm room, so I could not host. For some reason I talked to a lot of guys that wanted to meet in a park, abandoned building, parking lot, etc. Even though the thought of meeting to play in public got me really hot (still does), the idea of getting caught and arrested and having to tell my parents killed that fantasy. I finally ran across a bulletin board (remember those, lol) on a site dedicated to masturbation.

I placed an add, and got a couple of replies quickly, but none that really caught my attention. But the next morning I got one that did immediately. It was from a man named Freddy. He told me a little about himself and attached a couple of pics, and he was perfect. He was 36, which with me being 19 at the time was a great start, seeing as how much I fantasized about older men. He was Latino, another attraction, and he was slightly chubby and hairy. I was also a little chubby and kind of hairy, so this made me more comfortable. I particularly loved the hair (for what it is worth, I have always been obsessed with women that have a nice, full bush, so maybe that is just a fetish). He lived alone and said we could play at his place. We exchanged a couple of emails, and he left his number. A couple of days later I got up the nerve to call him. He said that he was doing something for work, but he would be free if I came by in about an hour. He only lived about 10 minutes from campus, so I would have to wait. This was one of the longest hours of my life. I was rock hard the entire time, wanting to touch myself so badly, but knowing that I should wait. My fear was I would cum so hard it would drain me and I would lose the nerve to go through with it.

Finally it was time to leave. It was raining and I was in such a hurry that I nearly spun out at the last light before I got to his place. I got out of my truck shaking, and the nerves and my concentration on his directions (remember, no navigation back then) had taken away my hardon, at least for the moment. Finally I found his door, knocked, and he let me in.

He looked exactly as I expected. I had not seen his face, and he had a sexy mustache as well, which I liked. His apartment was old, but well kept. He had asked before I came over what kind of porn I would like. I told him I did not care, but since he knew this was my first time, he had some straight porn on since I imagine he thought it would make me more comfortable. We made a little small talk. He asked me about school, told me a little about his work, and told me about some of the other guys from school that he had been seeing. He then said if I liked we could sit on the couch.

I nervously asked if I should take off my clothes. He said I could just pull down my pants, which both relieved and disappointed me. We sat down and both pulled our pants down. I was not hard, but that took about 2 seconds to fix. We started to stroke ourselves and I looked over at him touching a beautiful cock. Perfect size, bigger than mine but not too big, with a nice head and a sexy tuft of hair around it. He made a few comments about the movie, then reached over and began to play with my balls a little. I had never had my balls touched like that before, and instantly a bit of precum appeared at the head of my cock. He took a finger to rub it off and taste it. I took my hand off to stroke him a bit, and he quickly took the opening to do the same to me. I wanted to lean over and taste him, but was too nervous to do so. Then I leaned back and watched as he gently ran his hand up and down my shaft. My heart was racing, shocked that I had finally gone through with this, and excited at the feeling. He saw that I was enjoying this and probably guessed that it would not take too much to make me explode. I had expected us to spend some time stroking each other, but Freddy had other ideas.

He told me to stand up, which I did, then pulled my pants all the way down. The next thing I knew, he gently started playing with my balls, then took my throbbing cock into his mouth. This was the first time I had experienced this, and it gave me a rush I don't think I could put into words. I did not have a way to time how long this lasted, but my guess is about 30 or 45 seconds before I exploded into his mouth. I am usually a big cummer, and had held back before i headed over, so it must have been a gusher. I went weak at the knees and barely kept from falling down. Freddy swallowed every last drop and looked up at me and smiled.

I collapsed back onto my spot on the couch, trying to catch my breath. I didn't know the decorum for this situation, so I pulled my pants back up. He joked about how I must have needed that. We talked for a few minutes, and he was stroking himself a bit, which I hardly hid noticing. Soon I was rock hard again, which he could see. I flexed my dick a bit, and he joked that it was calling him. Then he knelt down in front me, reached into my pants, and took it out. This time I took my pants completely off, and Freddy began blowjob number 2. This time I managed to last a few minutes, but his mouth, wet mouth going up and down my shaft, and his hand gently fondling my balls still led me to explode into his mouth. He seemed pleased that he could make me cum so easily and quickly twice. I was so sensitive that I had to pull back as he continued to suck after I came because it actually hurt a little.

After I composed myself, I realized I needed to piss. I asked if I could use his bathroom, and was surprised that I did not bother to put on my pants or even shut the door. When I walked back to the couch, he joked about how I must be more comfortable. I replied that I figured there was no reason to be shy around a guy that just had your dick in his mouth, which got a good laugh. We sat and talked for a few minutes, and he noticed that even now I was still somewhat hard. He began to play with me a little, and once I was fully erect, he leaned down across the couch, said I could probably tell how much like to suck dick, and took my hard cock into his mouth again. I lasted a little longer this time, but only a few minutes before I came in mouth once more. After I was done, I sat there exposed for a little while longer, before I told him I needed to go. I did have a window before I needed to leave, but could have stayed a bit longer. But I was not really sure where to go from here. At this point I was no longer hard, and did not know how long before I could get it up again. I still wanted to feel his cock in my mouth, but was too nervous to make that move. I left and told him I would love to come back sometime. He said he would like that too, rubbing on my dick, which turned me on. All in all, Freddy had made me cum hard 3 times in about 40 minutes.

I played with him a few other times, but it was never as hot as the first time. Even driving around and going by his apartment I would get a little hard. This was one of the hottest times I have ever had, and it started me on a journey of sexual experiences that I shared with other men.