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This is a story of fiction. Author does not recommend unprotected anal sex.
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 Amsterdam Shemale 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.
“Let me get some lube,” I said, giving him a kiss and getting out of bed. I found the tube in the pocket of my sweats, and smeared a good amount on the out ring, and also pushed Rotterdam Shemale some inside. I turned around and caught me breath at the sight of him, laying stretched out on the bed in the faint light through the window, lazily stroking his cock. I got in bed on my knees next to him, and bent over, taking the fat head into my mouth. I’ve never been able to deep throat, and it wasn’t going to happen today either, not with this monster. But I sucked my lips down under the head, and started working the sensitive skin with my tongue, bobbing my head up and down at the same time.
“Oh yeah,” he groaned, “I love getting sucked.” His hand cupped my ass again, finding my hole with a finger. This time, it slipped right in, making my ass tingle with delicious sensations. I kept sucking and licking his cock head, swallowing the salty precum oozing out, and gently stroking the shaft with my hand. I glanced up at him, and saw his eyes were shut tight, his mouth open, making little noises as his hips jerked and twitched. My own cock was leaking precum like crazy too, dribbling down and wetting the sheet. I was incredibly turned on, forgetting my earlier unease at taking Billy’s thick cock, caught up in the excitement of the moment.
“Mmm, you do that good,” he murmured. “You gonna swallow my cum?” I pulled my mouth off his cock and looked at him, while still slowly jacking him.
“I can, but I’d rather have it in my ass. You want to fuck me?”
“Yeah, that would be awesome,” he said, raising up on his elbows. “You have any condoms?”
Shit! I assumed he had some, and didn’t bring any. And I damn sure wasn’t going to home to get some. In my heated state, I threw caution out the window.
“Nope, sorry. But we can do it without, if you’re okay with it?” He didn’t say anything right away, and I had a moment of panic, thinking I’d messed up.
“Yeah, I guess,” he said with a shrug. “Never went bare before.”
“I have, a long time ago, I think you’ll like it. I’m clean, you’re clean, it’ll be okay.” As I said that, I took the lube, and squirted some on his cock, and started spreading it up and down its length. He watched me do it, his eyes gleaming and his breathing coming fast. After putting a nice coat of lube on his cock, I reached back and gave myself some more, then lay the tube down.
“How do you want me?” I asked.
“Let’s start out standing up,” he said, “then we can try something else.
I got out of bed, and spied a chair by the wall. Turning it around, I grabbed the top, then stretched out my body and spread my legs, my heart pounding with excitement and anticipation. I felt Billy’s hands on my hips, then the shaft of his cock in the cleft between my ass cheeks. He rubbed it up and down a couple of times, then pulled back. Moving a hand to his cock, he put the head against my hole, and gently pushed in. I let out a deep breath, and pushed my ass ring out, trying to open it up. Billy pushed harder, and I felt the ring start to stretch. This was always the painful part, especially if it had been a while. The familiar burn started, grew, then suddenly became intense as the head stretched my hole open and pushed through the ring.
“Ah…Fuck!” I gasped out. Billy stopped, and pulled out. Whew, that hurt, but I knew the worst was past. I clenched my asshole a couple of times, Netherlands Shemale then told him to try again. This time, he went right in, and started to slowly borer his way deeper.
Each time, he’d pull out until only the head was in, then push in a bit deeper than before. My cock had gone soft when the pain hit, but was hard again, and I watched drips of clear precum dribble out, then drop on the floor under me. When he pushed back in each time, the head would bump against my prostate, sending jolts of sensation through my insides.
“God, you’re tight, but it feels so fucking good,” he groaned. “You okay?”
“Yeah, it’s fucking awesome. Never had one this big before.”
“Fuckin A, man, going bare feels waaaay better. I’m gonna cum pretty quick though.”
“Told ya. You want to finish like this?” I asked. At this point, I was going to do what ever he wanted, I just wanted him to keep fucking me.
“Uh, let’s change positions.” He stopped, and slowly withdrew. When he pulled out, my asshole gaped open, and I shivered as the cool air went up inside.
“Get on the bed, on your back, I’ll lay on top of you.”
I did as he wanted, and got in position, pulling my legs back out of the way. Billy got on his knees up next to me, and putting his cock in place, sunk it in me. At the same time, he lowered his body down onto mine, and wrapped his arms around my neck. This is one of my favorite positions, especially if my partner is hung. I wrapped my arms around his back, and crossed my ankles behind his lower back. Tied together and entwined, we kissed each other, and Billy started to fuck me again. In this position, the pressure on my prostate was continuous, giving me pleasure like never before. All pain and discomfort was gone. I was totally focused on the young stud holding me tight as he plunged his big cock into me. Billy was going faster now, breathing hard and grunting on every stroke. I could feel my orgasm starting to grow, the stimulation inside me pushing me along. I didn’t want it to stop, but the friction on his cock was working it’s magic.
“Mmm, gonna cum soon,” Billy whispered.
“Okay man, do it, cum inside me,” I breathed into his ear. He held me tighter, and picked up his pace, giving me several fast shallow strokes.
“Ah fuck…uungh,” he groaned and drove his cock into me, all the way to the hilt, cum spewing out of the tip. he pulled out, and shoved back in, three more times, then he was done. We stayed in that position for several minutes, letting ourselves settle down, then Billy pulled out and rolled off me. I let me feet back down on the bed, and felt his cum oozing out. He looked over at me, and seeing my cock was still hard and straining, moved around until his head was at my waist, then sucked my cock in, and gave me a short intense blowjob. I arched my back and blew my load into his mouth. Then he moved up and kissed me, letting me taste my cum too.
I spent the night, and got fucked again before dawn, waking up to feel him spooned up against my back, and rubbing lube into my ass. Then he gave me a very slow and pleasant fucking on my side, cumming in me, then stroking my cock until I blew all over his sheets. We got together several more times, going bare every time. I knew it was too goo to last, and sure enough, he told me one day he had met a guy that was a bit younger than him, and was going to go out on a date. I thanked him for being honest, and we parted. A few months later, I met a couple that closer to my age, and they introduced me to group sex, but that’s a story in itself.
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