Where it happened: In my apartment
Langauge: english
Sex: Male
Rating: 5
Category: Straight
For most of my twenties and early thirties I thought I was completely straight.I had fooled around with a good friend in high school but a few quick mutual blow jobs were as far as it went. I convinced myself I was attracted to women and that my “fling” with him was just a little experimentation that I needed to get out of my system. After that I exclusively dated women until my early thirties. For some reason I could never fully commit to them. At thirty-two I broke up with a girl I had been dating for six years. It was during the aftermath of that breakup that I started to wonder about my sexuality. I found myself starting to fantasize about being with men. I also regretted not exploring more with my high school buddy. He had wanted to try anal sex but I had shied away from the idea. I now found myself getting extremely turned on by the thought of him fucking me in the ass with his large, beautiful penis. It was then that I started to think about finding someone who would fuck me. I am a very muscular, masculine looking man and at the time I didnt think another man would want someone as “manly” as myself. Little did I know how wrong I was. I didn’t actively seek anyone, mainly because I didn’t know how. Luckily I stumbled upon an opportunity. I was riding the subway ( I live in NYC) home from work and Found myself sitting next to a balding, not particularly attractive man in his early 50s. When the train arrived at my stop I got up to exit the train and I heard the guy whisper “see ya around cutie”. At first I wasnt sure I was heard him correctly, but I hoped that I had. Even though not attractive, his aggressiveness turned me on. For the next two weeks I rode the train home at the same time hoping to spot him. I had just given up hope when one day I saw him at the end of my car. He had already seen me and gave me a wink when our eyes met. My penis immediately became harder than it had been in years. I was so horny that I decided to stay on the train until he exited. I still wasn’t sure what I’d do.
He noticed that I didnt get off at my stop and used that excuse to come over and talk to me. I was so nervous I could barely speak. He finally asked me if Id be interested in spending some time with him and all I could reply was “sure. He then said “how about now, do you have a place to yourself?”. I told him that I did and at the next stop we exited the train and caught the next train headed back to where I live. I could not believe I was doing this. I had no idea what would happen. After we got off at my stop we started walking to my apartment. He started asking me about my sexual preferences and fantasies. I ended up telling him that I wanted to be fucked by a guy. He said “Great, cause I’m a top”. At the time I didn’t know what this meant. But I quickly learned. When we reached my place I didnt know what to do. I suggested we watch tv. Well, this didnt last long. Very soon he started touching me and next thing I know we are kissing. I was so turned on I could hardly stand it. Apparantly he felt the same way. The next thing I knew we were naked in my bedroom, his cock was in my nouth and he was reaching around to my ass lubing it up. It all happaned so fast I just let things progress naturally. He then told me he needed to be inside me. He knew it was my first time so he was very gentle. He moved us into thespoon position and soon pushing his rigid cock against my ass. I was nervous and when he pushed it in it hurt at first. But I quickly knew this was a wonderful feeling and had to have more. That first time he fucked me slowly and eventually came in my ass. He is the only person I’ve allowed to do this without a condom. We fucked about once a week for a year, until I found a steady boyfriend more my own age. But I shall never forget the man I met on the train who taught me the joy of anal sex.
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