This story is a work of fiction based on true events.
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I don't know how it started. I was just chatting for a while, then we were fucking. I mean, how did it get to this? It was all a blur, yet it was good, but how did it happen? All I wanted to do was chat, not get my ass fucked. But...
Maybe I should start at the beginning.
I was bored that night and decided to chat online for a while. I had just joined this gay chat site without really thinking much of it. I was still exploring my sexuality, and I thought chatting with other gays would help. The chatroom was quiet, as usual, so I checked out the profiles of the people in the room.
Then a private chat window opened. Curious, I said "hi." The person said "hi" back. We chatted for a while, then he asked me point-blank: "Wanna hook up?" And something in me said: "Yes!" We exchanged stats: I'm 6-feet tall, slim and hadn't had sex in a few years. He was about 6-and-a-half-feet tall, athletic build and knew how to have a good time. In a while, I told him how to get to my place and he said he'd be there in half an hour.
Those were the most nervous 30 minutes of my life. I still wasn't sure why I had agreed to hook up. I was feeling a bit horny, but I didn't think I wanted sex. Anyway, the date had been set and all I had to do was make up my room.
He arrived promptly and I ushered him in. He was pretty much how he had described himself, except that he was a bit on the pudgy side. That was fine with me. We made small talk about the weather, then he asked me, "So what do you want to do?"
"I don't really know," I said. "It's been a while since I've done this."
With that, he hugged me and started kissing me on the lips. I went along with it and opened my mouth to let his hungry tongue in. Our hands roamed all over each other's bodies, from our backs to our butts. Pretty soon, we had undressed each other. He pulled me closer, grinding our bodies together. I felt his erect dick press against me, as did mine against him. We kissed and necked for a while, then broke off and admired each other.
We sat down on the bed in such a position that his dick was right in my face. Without a word, I bent down and sucked the head. He moaned and I acknowledged by taking his whole dick into my mouth. It filled me completely, making me suck on it more. But my dick needed some action too, so I moved my bum closer to him. He knew what to do too. 10 minutes after he had arrived, we were sucking on each other.
Then he pulled me up onto his face. I wasn't sure what to expect next. Suddenly, I felt his whole face against my butt, then something wet attacking my ass. He was rimming me! And it was the greatest feeling! He licked and sucked me so tightly, I thought there was a vacuum pump down there. I moaned loudly and he just licked me further.
Then he stopped as suddenly as he had started. "I wanna fuck you," he said simply.
"How do you want it?" I asked.
"Stand against the bed and bend over."
That was a position I'd never done before but I was game for it. I got into position while he lubed himself up and slipped a condom on. (We had both insisted over chat about safe sex.) I felt a cold glop on my ass, which was the lube, then something pressing against me. I didn't need to be a psychic to know that it was his dick.
But it hurt. Like I said, it'd been a few years since I last had sex, so I wasn't really ready. I groaned in pain as sharp pangs swept from my ass to the bottom of my spine. "Wait, wait," I moaned. He got the idea and just rested there. After a while, he pushed in again, spreading my ass wider. The pain was still there, but I wanted his dick more. I gritted my teeth and felt him slowly enter me.
Soon he was in me, but the pain was still there and my legs were almost buckling. "This isn't good for me," I said. "I think you're too tall for me."
"That's fine," he said in an understanding manner. "Why don't you lie down?"