Teenage First Time

To some of you, this may seem like Greek. For those of us that remember the early days of the internet, this story will make a lot more sense. This is the story of my first time with another man, an older man that certainly knew what he was doing.

I had just turned 18, was finishing up my last couple months of High School, and would leave for the Army at the end of the summer. I was raised in a very fundamental, catholic household, but had been curious about being with another man for as long as I could remember. I signed into AOL and entered a local chat room. As was tradition, the first question was "ASL?". I responded 18/M/Colorado Springs, and things progressed as usual. Most people in the chat room were just talking nonsense and trying to impress women that were enjoying all of the options. After a few instant messages and a couple uninteresting conversations, I received a message from someone that I hadn't seen in chat. They asked the same "ASL" question that was standard for the time, and I responded the same as I had before. I asked the same, and he responded with 45/M/Colorado Springs. Now, to this day, I still don't understand why I didn't just close the chat, but I decided that I would talk a little bit. I told him that I was straight, and he responded by saying that he was just looking for people to talk to. After an hour or so of chatting and discussing the frustrations of life as a teenage guy, he hit me with "If you just want a blowjob, I'd be happy to help. We are close to each other and I live alone." Now this wasn't the first time I had been propositioned online, and I usually just enjoyed the chat and logged off before committing to anything. For some reason, this time I was talking about how long it would take me to get there.

Fast forward an hour, and I was pulling up to a normal looking ranch-style house, just a couple miles away from where I lived. We had discussed a quick blow job and I was horny enough to give this a chance. He had told me his name was Lewis, and that he was recently divorced. I figured that regular blowjobs would be awesome for the summer and that a mouth was a mouth. I was shaking like a leaf when I knocked on the door, I was thinking about running way when Lewis opened the door. His pic was accurate, he was a middle-aged white guy in good shape, about 6 feet tall, with short salt and pepper hair. He invited me in, and in just a few moments, the door was shut behind me. Like I said, I was nervous as hell, and Lewis definitely noticed. He offered me a drink, and my teenage ass was happy to accept. While I was enjoying my drink, Lewis was asking me about how school and work were going. I told him that school was stressful as hell because of all of the studying that was required for finals. It wasn't long before he said that he would help get my mind off of things. In the next minute, my pants were down, underwear around my thighs, and I could feel his breath on my cock. It was still in my mind that I could leave at any moment, but then I felt the wet warmth wrapping around my teenage cock. As soon as I felt his mouth, I knew I was going to sit back and enjoy what was happening.

So there I was, sitting on a couch, pants around my ankles, a little buzzed, and getting a blowjob. I was in heaven, at least I felt like I was. For some damn reason, I couldn't get more than half hard. I could sense the frustration and, for the first time. I felt like I was too nervous to do this. I let out a long sigh and told Lewis that I was scared of what was happening and that I wanted to stop. He stopped and sat nest to me. He told me that we could just hang out and grabbed himself a drink. After another few minutes, he asked if it was okay for him to jack off? I told him it was fine, and before long there was another man stroking himself next to me. He was hard immediately, and I couldn't stop myself from looking at what was happening. He was around 7", cut, and pretty thick. I don't know if it was 10 minutes or 10 seconds, but he asked me if I wanted to touch it? I reached my handout and he leaned back. It was strange, hard and soft at the same time. I had touched myself so many times, but never paid attention to a cock actually felt. Apparently, all I ever cared about before was how my cock felt. This time, I actually realized what a cock felt like, and I liked it.

Lewis leaned back and before I knew it, I was stroking another man's cock. I was in a trance, enjoying the feeling of a cock that wasn't my own, It didn't take long for Lewis to say things were getting dry. He was right, my hand wasn't sliding anymore, it was basically sticking to him. I stopped and looked at Lewis. He asked if I was willing to try sucking his cock, even if it was only to get it wet again. I couldn't make a sound. I knew what I wanted, but I couldn't get the idea out of my head that I was doing something wrong. Without saying a word, Lewis reached behind my head and guided it down. Honestly, I didn't resist. I just let him guide my head down, opened my mouth, and wrapped my lips around his cock. It felt strange in my mouth, but I thought I knew what I needed to do. I started trying my best to imitate the shitty porn that was available on dial-up internet. I'm not kidding when I say that I was giving it my damn all. Suddenly, my mouth was hurting, I was slowing down, and he was noticing.

I tried to give a final push, but I just couldn't keep going. I went to sit up and felt a hand on my head and heard "just a bit more," "I was so close," There it was, I sat up and saw that look again. He didn't finish, and I realized that I wanted to make him cum. I sat there and Lewis went right back to stroking himself. Just like before, my eyes were fixed on what was happening, and realizing that didn't think I could get him off. That's when he asked me, "have you ever thought about anal?" Of course I had! What curious teenage guy hasn't thought about anal? I was buzzed, I was horny, and I was disappointed that I couldn't make him cum. I responded "yeah, I've thought about i." That's when I heard the phrase that I now know was bullshit "Did you want to try it? I can't really cum from oral."

There I was, face down on his bed, pillow under my hips, feeling a lubed finger pressing against my hole. He didn't take long. One finger turned into two, more lube was getting worked into me. That's when I was suddenly empty and then felt him get up on the bed behind me. I asked if he had a condom and he moaned, he just heard me accept what was about to happen. He put on a condom, put a little more lube on me, and touched his cock to my virgin hole. He told me to push out and I could feel pressure. He kept pushing, and after a minute or two, I felt myself open up and knew that he was inside me. I give him credit, he took his time, just the tip. It hurt, it hurt a lot, it was wrong, and I said "fuck me."

I don't know why I said it, but Lewis wasn't going to pass on the opportunity. He started pushing into me, stretching me out until he was all the way inside. I was doing it, I was getting fucked. At least that is what I thought, then Lewis started to pull out and push back in, Now I was getting fucked! I figured out Lewis' dom side pretty quick because he started to go hard. Before long he was slamming into me and scraping across the inside of my ass. He was loving it and so was I, and then I had to pee. In the middle of getting fucked, I said I had to go to the bathroom, and Lewis just pulled out, chuckled, and showed me where it was. A lot of guys realize already that I didn't have to pee, Lewis was hitting my prostate and I couldn't understand the feeling.

I came out of the bathroom determined, went straight to the bed and put my ass up. Lewis got behind me and told me to roll over. I did as I was told and he immediately shoved all the way into me. He no longer cared how I felt, he was tired of waiting. All the way out, slamming in, grabbing my throat, pounding my hole. I was in pain and ecstasy. Then he said he was going to cum, I simply replied "please." A few pumps later he slammed inside, tensed up, held his breath, and I could feel his cock start to twitch. To my surprise, I was so damn happy that I made him cum.

When I came down from cloud nine, something felt wrong. He was still inside me. I was panting, I was sore, I was wet? That's when he pulled out of me, and if I hadn't seen his cock, I would have known from the feeling. "I told you to wear a condom!" He said that he did, but that he took it off so he could stay hard while I went to the bathroom. I asked him if he came inside me and he just chuckled. I started to panic, how could I have let this happen? That's when he laid down next to me. "Don't worry babe, I'm clean, you felt amazing." He started to calm be down and then started playing with my cock. Suddenly I realized how close I already was to cumming, I was right on the edge. But for some reason, Lewis slowed down, squeezed the base, kept me close but not there. "Let me fuck you again."

What? Again? "Please."

With me on my back and him on his side next to me. He moved closer, lined up, and pushed into my sore ass. This time was slow, deep, and rather than thinking I needed to pee, the pressure on my prostate made me leak non-stop. It felt better than I ever thought sex could feel. That's when Lewis asked if I wanted him to pull out? I He started to cum in me just as I said the words "don't pull out."

That night I laid in bed, my ass was sore and still full of cum. How could I have done that? I'm not gay...

Lewis fucked me raw almost every day until I left for the Army. His cum was in me when I got on the plane for basic training.