This is a story of fiction. Author does not recommend unprotected anal sex.
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The personals section of the well-known Craigslist site provided a wealth of opportunity, especially for gay or bi men, and every week seemed to bring new men to the site. There were some fakes, of course, but most were like me, ordinary guys looking for casual sex. If I was traveling, it was easy to get on the site, select the state and city, and begin browsing. I was selective, and only hooked up with a few guys, but they were memorable. So, it was with great dismay when I learned that CL pulled the personals section. Later, I discovered that people were posting in the missed connections section. With nothing to lose, I gave it a try, putting up a post for Local Tops. I checked my email the next day, and wow, lots of responses. Most I deleted, since they were too far away, they were bottoms like me (can't people read?), they were overly aggressive, or obvious fakes.
Of the few that I kept, one stood out, from billybob1989. A younger guy at age 28, his message stated that he lived nearby, was a total top, and was eager to meet. He hadn't been with a guy in a long time, it said. It sounded good, almost too good, so I sent a message back, asking a few questions, and including front and back pictures of my body from the shoulders down. I had other things to do, so shut down the computer and left. That evening, I got back on, and saw I had new mail from billybob1989, with pictures attached. I opened those first. Wow, I hoped this guy was real! The first picture looked like it had been taken in a car. I could see legs and the steering wheel. His jeans were unfastened, and a nice thick cock was curving up at the camera, the head just poking through foreskin. The next was a picture from the side, probably in his bathroom, showing a slender body a normal amount of body hair. it was cut off just below his eyes, so I could see he had a whispy dark goatee. But the main feature was his cock, fully erect, curving out and up from his crotch. It was a big one, for sure.
I managed to pull myself from the pictures, and read the text. My own cock was throbbing with excitement, and my asshole twitched as I imagined that cock of his sliding up inside me. He answered my questions, saying he was clean, and had always been safe. He'd had a boyfriend, but they had broken up several moths ago. He worked a long shift every day at a local factory, but usually free in the late evening, and was willing to host. This was all sounding better and better, but I wanted to be sure. I sent another message, telling him I was sixty years old. Did he like older men? I attached pictures with close-ups of my cock and ass as well. A few minutes passed, and he responded. No pictures, just a nice response. He said he was definitely interested in meeting, and the fact that I was older just added to the thrill. He also said that he'd go as slow and easy as I wanted to, because he wanted me to have just as much fun as he did. The words rang true to me. I thought about it for a few minutes, and decided to go for it. I wasn't going to have the chance every day to be with a guy his age. I sent the response, asking if he would like to meet, and in a very short time he answered YES.
After getting his address, I told him I was going to get nice and clean for him, and would be there in 30 minutes or so, then I went through my usual routine, first an enema to clean out my insides, followed by a hot shower and lots of body wash. I threw on a cutoff and sweat pants, and left for his place. He lived in an older apartment building on the other side of town, just a few minutes away. When I got there, I parked away from the building, found his door on the ground floor, and knocked. My heart was beating fast, as it always did meeting a guy for the first time. Then the lock clicked, and the door opened. Just like his description, he was a few inches taller than my 5'8", and slender. He was good looking in a dorky kind of way, his dark hair pulled back into a man bun. His facial features were soft, maybe even a bit feminine.
"Hey, hi, I'm Billy, come on in," he said, stepping aside and waving me in. The apartment was small, without much furniture, but fairly clean. So far, so good.
"Nice place," I said, "not the typical boar's nest most single guys have."
"Thanks. Yeah, I try to keep it clean." Unlike his face, his voice was deep and masculine. "Well, come on back to the bedroom." He shut off the light, and led the way to his bedroom. The bed wasn't made up, and a few clothes were laying around, but it wasn't bad, so when he pulled off his t-shirt, I did the same. When he pulled down his shorts and stood up, I got my first look at his cock. Most of the time, they look bigger in pictures than in real life. His, if anything, was bigger. It wasn't fully erect, sticking out from his crotch and curving down, but was still a good eight, maybe nine inches long. The head was fat with a prominent crown. I had a moment of misgiving, wondering if I could handle it. I'd taken a couple of good sized cocks in the past, 7 inches plus, and had really liked the way they filled me up. Billy's however, was not only longer but also thicker. It was going to take a lot of lube, and going slow at first. I climbed into bed next to him, and we started off by making out.
He was a good kisser, and obviously liked it, rolling his tongue over and around mine while letting his hands roam over my body. I did the same, and in no time we were both hard, oozing precum from the heads. His cock dwarfed my six incher when they rubbed together.
"Mmm, you're going to have to take it easy on me," I said when I came up for air. He gave me a soft kiss.
"Oh yeah, definitely. I'm pretty big. I'll ease it in, until you get used to it, then I'll go slow as you want." He seemed sincere, so I relaxed, and picked up where we left off, sliding my hand down his chest, following the trail of curly black hair across his belly until it came to the base of his cock. Wrapping my hand around it, it felt just as big as it looked. Gripping it lightly, I stroked up to the head, and back down to the base, feeling it twitch in my hand.
"Aaah," he breathed into my mouth. His hand moved down my back until it cupped my ass, and I felt a finger probe at the puckered ring of my ass, rubbing around the brown ring, trying to get in. I let go of his cock and sat up.
