1. I took some convincing…


    Date: 8/21/2015, Categories: First Time, Gay Male, Author: chris_108, Rating: 96, Source: xHamster

    I had been thinking about having sex with a man for many years. I came close multiple times. I had always come to a point where I had to choose whether or not I was going to go through with it. I had always chickened out. This time was different. I was traveling for work. Being alone in a hotel room gives a married guy too much temptation. I jumped on Squirt and surfed around looking for some attention. That's when Jonathan instant messaged me. Jonathan was older than I was. He was in his mid 50s while I was 46. We chatted for nearly an hour. I was getting really horny as I asked him what his first experience with another guy was like. Finally, he told me that he would give me as much detail as I wanted in person if I only gave him my room number. This was a huge step for me. I wasn't sure I could actually go through with it. But I convinced myself that if he came over to my hotel room, we would only talk about his experiences. I knew it would likely lead to something more but I thought 'more' meant that we would simply jerk off in front of one another. I had jerked off in front of other guys a few times before and it never graduated to touching or anything else. So I thought I would be safe. I gave in and told him that I was staying at the Marriott in room 332. Jonathan didn't live very far away from the hotel. He showed up in 20 minutes. I was actually kind of shocked. I didn't think he would actually show up. After the knock at the door, my heart sank. I debated with ...
    myself on whether or not I should pretend I wasn't even in the room. I also didn't want to be rude. I did in fact invite him over after all. I finally said to myself &#034fuck it&#034 and I opened the door. Jonathan was very much as he described himself to be. Little bit taller than I was at 6'2&#034, about 210 pounds. Little streaks of gray in his goatee and in his hair. We shook hands and he entered my room. After some small talk, we started to watch some porn together. It was lesbian porn… My favorite. We started talking about sex, about what his first time was like. The emotions he felt, the sensations he encountered. Jonathan described everything about what it felt like to have someone's dick in his mouth. He even described what it tasted like. By this time I was pretty revved up. He took things so slow with me. He asked me if I was ever going to surrender to my desires and finally go through with it. I was still unsure. What would that make me if I did that? Would I be gay? It sounds like a very silly question but at the time it was central to how I self identified. I didn't want how I identified myself to change and yet it felt like it was about to. He kept saying &#034at some point you're simply going to have to just try it.&#034 He was right, but I still needed more convincing. He asked me if it was okay if he touched himself. I was a little caught off guard. Considering the situation I placed myself in, I don't know why I was surprised. But I was. Was this really ...
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