My First Gay Encounter

Most of my life, I have been interested in hooking up with a guy. Ever since my college years I wondered what it would be like to suck on a cock or even have one in my ass. I used to have to walk a lot back then to get anywhere and always fantasized about an older guy picking me up to give me a ride and then take me back to his place to experience my first time.

Fast forward to when I am 34 years old and married. It is 1997 and I still have never had any type of gay experience. I had talked on phone lines before with guys, but that never came close to working out. The internet had just started getting popular and I finally bought my first computer. I signed up for AOL, as most people did then, and was learning how to use it. I soon discovered that AOL had chat rooms for just about every interest, including gay and bisexual men. I got on and mostly observed at first and then started talking to a few guys. Nothing was really happening because most of them were pretty far away from my somewhat isolated area.

Eventually I started talking to a guy (Greg) about 20 years older than me that lived in Phoenix. He was a nurse who had come out to his wife and was still living with her. They were working on a separation and eventually a divorce, but were still getting along. As luck, or serendipity, would have it, my wife and I were planning a trip to Phoenix to visit her grandmother. At this point, the wheels were turning in my head. Would it be possible to pull this off and would I actually be able to go through with it?

I decided that I needed to make this happen, one way or another. I needed to experience what I had been missing. I worked for a large car rental company and my boss gave me a car to use for the week we would be in Phoenix. This provided an opening for the opportunity and I told my wife that my boss would like me to meet with our local sales guy in Phoenix for a couple of hours to discuss business. Kind of a condition of the free car rental. She was absolutely ok with it as she was there to visit family anyway. I gave Greg my local phone number and told him to make sure he followed my back story. He was absolutely fine with it.

He eventually called while I was in Phoenix and we made plans to meet at a local motel 6. Inexpensive and will do the job. I checked into the motel, called him with the room number, and showered again to get ready for our encounter. Needless to say, my heart was racing from nervousness and excitement. Eventually I heard a knock at the door and jumped up to answer. Here was a very nice looking guy with a trim beard and in nice shape. He walked in, shut the door, and gave me a deep kiss on the lips, which was a completely new experience for me. At the point I started unbuttoning his shirt and found a chest nicely covered in fur. I was extremely overwhelmed and just started kissing him on his chest as I continued to undress him. I needed to see his cock and touch it. When I lowered his underwear and saw his mostly erect cock, I knew I was doing the right thing. I immediately got down on my knees and started licking the shaft. He was moaning a little bit, so I knew I was doing ok. I had to put it in my mouth and start sucking it. He told me that he could not believe it was my first time trying this. I loved the taste of it and the way it filled my mouth. It was average size, so I was dealing with it well.

After about 10 minutes of this, he said he didn't want to cum yet but wanted to return the favor. He pulled my pants down and started stroking my cock, the first time another man had ever touched it. He had me lay on my back on the bed and put his lips around my cock. I had received blowjobs from women before, but this was different. After a very short time I told him I was going to cum soon and he stopped sucking me. He had other plans. He had me roll over to my stomach and started fingering my ass. At this point, I told him he could do whatever he wanted to do to me because I was losing it. I had never felt so much pleasure in my life. I felt something warm and wet in my ass and I realized he was using lube. It felt even more incredible, but I knew I wanted more than just a finger in my ass. I was doing a lot of moaning and he knew I was enjoying it. At this point he asked me if I wanted to get fucked and I quickly agreed. I knew I was ready for it.

He slid his cock in slowly, but I don't remember there being much pain. I was enjoying it so much I started pushing against his cock wanting more. He took my signal and was suddenly in me balls deep. He started fucking me harder and harder and I told him to not stop. I was loving it too much. Probably after about another 10 minutes of this, he told me he was going to cum. I told him to not take his cock out of my ass because I wanted to feel his cum in me. I wanted to feel a hot load in my ass. He started grunting louder and said he was cumming. I could start to feel his warm seed in my ass and I knew I had finally been bred like I wanted. After he was done, he asked me how my first time was and I told him it was even better than I expected.

He asked me if I would like to return the favor and I was more than happy to do that. My cock was rock hard and felt like it was ready to explode. He laid flat on the bed and I put some lube on my cock and his ass. I raised his legs up and slid my cock in him. It felt like nothing I have ever felt before, as I had never fucked a man or woman in the ass. It was incredibly tight and warm. I would like to say I fucked his ass for hours, but there was no way I was going to last that long. I soon felt the pressure in my balls and told him I was going to cum. He told me to shoot inside him, he wanted to feel my first time in him. It seemed like I came for about a minute leaving about a gallon of cum in him.

Obviously not that much, but it felt like the biggest orgasm I ever had. My cock finally softened and I slid it out, followed by quite a bit of my white cream. We had both been thoroughly fucked, and it felt wonderful. I knew that the experience was everything I was looking for and would be doing it again. Greg went into the bathroom to clean up and I laid on the bed enjoying the wet feeling of cum in my ass. He came out and was ready to leave and we had another quick makeout session before he left. I wanted him to know how much I appreciated the fucking he gave me. I told him I would talk to him on AOL again, but knew there was no chance of ever getting together again. We kept in touch for a few months but we lost contact before too long. Even if I wasn't talking to him anymore, I would never forget my first gay experience.

I hope you like my story, it was 100% true and I have definitely had a few more experiences since and hope for some more. Maybe I can share some more soon.