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Sidewalk Talk: Tale of a Different Kind of Miami Turn-Around

In the midst of winter I like to think back to days when I was not fighting slushy, icy streets or mountains of snow. Today, I remember fondly an encounter on a sidewalk in South Beach in 2004.

I was staying at a rather crappy hotel on Collins Avenue, a block from the beach. I’d just checked in – into my hotel room and with my friend who lived nearby. I told my friend that I wanted to rest a bit. I lied. Stealing out the back way of the hotel, I escaped down an alley which led to a sidewalk that would take me to the beach. I was so excited. My plan was to revisit a restroom on the beach that has always been quite cruisy and one in which I have gotten my rocks off a number of times during my then frequent visits to Miami.

As I made my way to the beach, I passed by a cute, younger man – in his late twenties. He was just under six foot tall, with light brown executive-cut hair and hazel eyes. He was wearing a pair of washed out khakis, sandals and an unbuttoned, tropically-themed, short-sleeve shirt exposing just a hint of his mostly hairless chest. His hands were in his pockets. Quite good looking, with a classic, strong chin, and great cheek bones, I don’t know what it was about him that made me risk turning around and checking him out again, but I did. Feeling full of adventure and lust, I spun around thinking that this man was so out of my league, a chance glance was the closest I would ever come to having sexual contact with him.

As it happened… there was something in the air in that brief moment when we passed each other on the sidewalk, for as I turned around to check him out again, he turned around to check me out. From the initial look in our eyes, it was obvious that neither was really expecting to meet the gaze of the other. In fact, we were both still in mid-step. I continued on, he halted. Realizing that he was now standing still, staring at my back, I spun around one more time and also came to a stop. He just stood there, staring, smiling. I smiled, too broadly, no doubt and had no idea what to do next. My blood was pumping, my heart racing. My head told me to go, continue on my way, and I was just about to, when one of his hands came out of his pants pocket and gently squeezed the crotch of his khakis.

Again, heart skipping a beat, I struggled to take a breath. What now?

Locking eyes, we began to walk towards one another. There were people walking all around us – on the other side of the street, next to us, behind us, but neither of us seemed to care. Small, wicked smiles played across our lips. With a yank of my head, indicating that he should follow, I retraced my steps back to my hotel. It felt covert and exotic. Hours before I’d been escaping from the drudgery of a Minnesota winter and here I was about to do something sordid and flagrant with a total stranger in a sun-kissed city where I’d only just arrived.

Silently, he followed about ten paces behind me through the alley and the open courtyard of my hotel. Once secure behind the door of my hotel room, we lost no time getting busy. Moving in for a kiss, my lips were re-directed to the fly of his khakis. On my knees, I could see that this man must be one hell of a camper, because he sure could pitch a tent. Unzipping his fly, I immediately came face to face with the head of his dick as it poked out through the opening of his boxers. I took that bad boy in my mouth to about midpoint. It was a very average cock… but then is any cock really average? Especially one that follows your ass back to your hotel room for a hot encounter?

He was halfway to hard when he first fell out of the fly of his boxers, so with only a bit of coaxing on my part he was soon at full mast. We were positioned right in front of the closed front door to my room. If someone had been standing on the other side peering through the peephole they would have gotten quite a show – a fish eye-view to be sure, but a nice show none the less.

Not one to trifle with clothing and without removing my mouth from his dick, I reached up and undid his belt and the button on his khakis. It simply makes it easier to work when everything is out in the open where you can see it. His thighs were covered with light brown hair and his bush was trimmed, but natural. Grabbing him by the balls, I brought his dick to my lips and swallowed deep. As the head touched the back I constricted my throat in order to add a bit of tension. He seemed pleased. His hands grabbed the sides of my head and he began to gently run his cock in and out of my mouth. Looking up, into his eyes, I could see a determined smile spread across his face.

There is always something extremely urgent about meetings like this. Everything becomes about fitting in as much activity as possible in the shortest amount of time, although both parties always seem focused on the same thing… shooting a load. This encounter would not prove to be an exception to that rule. I quickly ran through my gamut of cocksucking techniques. Once satisfied that I’d fulfilled that requirement (like a Boy Scout working towards a merit badge), I stood. I still wanted a kiss, but this guy had something else in mind – my ass. He put his chin down and began to fumble with button of my jeans. Thinking he just wanted to see my dick, I took over and quickly dropped them to the floor. Since I was headed to the beach intent on getting off, I had chosen to go commando that morning. I began to play with my dick, when suddenly I found myself spinning in place. The guy turns me around, bends me over and dives face first into my ass. Pretty sure of what was coming next and still bent over, I began searching the pockets of my jeans for my poppers and other supplies. They had barely spilled onto the floor before my sidewalk trick, reaching around me, grabbed the condom.

As he ripped the foil pack and rolled the condom on, I took a hit of poppers and waited to pass him the tiny, packet of travel-sized lube. Those little packets can be a bitch to open, but, using his teeth, this guy had no problem. I spread the cheeks of my ass waiting for him to lube me up. There was definite lack of verbal communication going on, so I guess I deserved what I got, which was an entrance into my hole that was about as graceful and pleasurable as a steel-toed boot being rammed up one’s hole at warp speed. Fuck, that hurt. I was seeing stars. I cried out, but my sidewalk trick would not be deterred from his mission: to dump that load. He grabbed my hips and rocketed in and out of my ass with a flurry that had me scrambling to uncork my bottle of poppers for another hit. Once their warmth spread through me, I relaxed and tried to get on-board with the program. Not that there was much of one.

He was relentless and seemed to be a one-trick-pony, that trick being a jackhammer-style approach to fucking. There wasn’t much I could do creatively to change things up, given our physical limitations (not near any item of furniture, pants around our ankles) and his urgency, so struggling to maintain my balance I began concentrating on my own dick, while adding the occasional moan or ‘fuck, yes’ to the soundtrack of whacka-whacka wafting through my hotel room. As he ramped towards his own orgasm, his hands moved from my hips to my shoulders, giving him even more leverage. It would be one of the few times I would hear his voice, a nice baritone, as he uh-uh-uh-uh-uhhhhh-oooohhhhhed his jizz into the reservoir tip of that condom buried deep in my ass. He shot about eight times and then grew still. For about one second.

I was still working towards my own orgasm, when he unceremoniously plopped his spent dick out of my ass, removed the condom and laid it on my backside. Swiftly pulling up his khakis and boxers, he peered around just in time to catch my first shot of cum hitting the hardwood floor. I was just finishing up my money shot as he was reaching for the door handle. Looking over his shoulder he said, ‘thanks’ and vanished.

I felt like I had just survived a hurricane. It all happened so fast. There was barely time to be disappointed. Not that I was. I know that’s just the nature of the beast. Peeling the used rubber from the top of my ass, I took note of the decent load he’d shot before walking it over with my jeans still around my ankles to deposit it in the john. Grabbing a towel, I returned to the scene of the crime to wipe up the lube, spit and cum that decorated the floor. What a mess. I thought about taking a shower, but decided that a dip in the ocean would probably feel much better. I pulled up my jeans, zipped, buttoned and grabbed my swimsuit from my open duffle bag. Figuring I’d get a cheap thrill changing on the beach, in front of total strangers, I grabbed a clean towel, a couple of condoms and mini-lubes, and headed out.

Walking down that same sidewalk, my recent trick moved into memory, as my thoughts centered on the reaction my freshly fucked ass would get as I stripped and changed into my swimsuit in the mens room on the beach. Who knows… maybe lightening would strike twice.

Or three or four times!

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