...and here's the whole story.
We met in an online chat room for gay nudists. After chatting a bit and exchanging pics, we decided we should get together and “hang naked.” He said to come to his place, on the UWS, just off of Central Park West. We were going to meet around 2:00, after he got home from his job, so at the appointed time I got ready and headed out.
Now, up to this point, there had been no sexual connotation to our interaction. We were just going to hang naked, maybe drink a beer, and shoot the shit. But on a whim, before I headed out I did my hole-cleaning ritual. Just in case one thing led to another. I cleaned up, put on a pair of shorts, a tank top and flip flops, and headed out. I free-balled it, figuring the underwear would be coming off soon enough anyway, and I like the feel of my cock and balls hanging free.
He was a little late getting home, so i was stuck waiting on his stoop for a while. It was a pleasant summer day, not one of the brutally hot NYC summer days, but in the low 80s, bright and cloudless. I sat and waited, noticing that because of my lack of underwear, my cock was visible up the leg of my shorts, if anyone had cared to look. No one did, but it made me feel rebellious and sexy sitting there waiting.
In a few minutes, he rounded the corner. I recognized him from his pictures immediately. He was a few years older than me, with dark hair peppered with grey, and he wore his suit well. He had a nice body—or at least it looked that way under his business attire. He looked at me, and immediately noticed my cock peeping out of the leg of my shorts, and smiled. We introduced ourselves, and he led the way up to his second floor apartment.
We wasted no time in stripping down naked. He offered me a beer, and I accepted. What I observed through his suit turned out to be true. He had a nice body under that suit, not a gym god, by any means, but a nicely shaped, natural build, and a beautiful cock. It appeared about 5 inches soft, with a nice fat head. We sat there in his living room, naked, taking each other in and sipping our beers.
Our conversation had not been going on very long when he said, out of the blue, “Can I suck your cock?” No workup to it. He went instantly from “and where did you grow up” to “Can I suck your cock.” I was a little taken aback at the abruptness of his question, and at the swiftness with which it arrived. We’d only been talking for about 10 minutes. But as I had no issues with him sucking my dick, I smiled and said, “Sure. 69?”
He pushed me back onto the day bed I was sitting on, and swung his cock over my mouth as he went all the way down on me in one graceful move. His hard cock was around 7.5 inches, and I was soon deep-throating his beautiful dick as he sucked down on my 6-incher with relish.
As we continued, however, it became apparent that he was more interested in my hole than my cock. After only a few minutes of sucking on my cock, he began lifting my legs up so he could get access to my fuckhole. He began rimming me with gusto as his hands slowly worked my penis. It felt fantastic.
We continued on like this for about 10 minutes, with me sucking feverishly on his dick while his tongue explored my hole and his hands worked my cock. Then he broke and said, “I really want to fuck you. Are you cool with that?” Without a second thought, I said, “yeah, I’m cool with that.” “Do you need a condom?” I had just started on PrEP, but most of the time still used condoms. However, this situation was really turning me on, so I said, “Usually, but I’m on PrEP so if you’d rather go without, I’m cool with it.” He smiled. “I’m on it too, and just got my test results back yesterday. I’m good without a condom.”
The window was open, and a nice gentle breeze wafted in as he lay on his back on the day bed, lubed up his cock, and handed me the bottle to slick up my hole. His fantastic rim job was all the preparation I needed, and I climbed on board and eased myself down onto his throbbing fuck stick. It was a perfect fit.
We were in no hurry, so I set a slow, steady pace, riding up and down on his cock, enjoying the sensation of his cock working my hole. I’d pull up until I felt his fat head just inside my sphincter, then lower myself back down on his rod until I was impaled all the way.
We continued on like this, a nice easy ride, both of us enjoying our connection. “This is nice,” he said. “Yeah, you feel great in my fuckhole.” We fucked as the light summer breeze wafted into the window and caressed our bodies. The feeling was pure bliss.
“You know, it’s such a nice day. Do you want to go up to the roof?” I was game for anything. “Sure!”
I got up off of his cock, he got up off the daybed, and grabbed his keys and the lube bottle. He walked to the door and slipped on his flip flops. “You probably want something on your feet up there.” And he opened the door, still naked and hard, the only article of clothing being the footwear he had slipped on. He stood there, his hard dick leaking a good amount of precum, waiting for me. I slowly got up, and looked quizzically at him. “No one is around this time of day in this building,” he said, reading my hesitancy, “we’re safe.” That was all the encouragement I needed. My hole still dripping with lube and his precum, I headed over, and headed out in front of him into the hallway. “Shoes!” he said, as I walked past him. “I’m kind of an avid bare-footer. I’ve been barefoot on rooftops before.” He shrugged, pulled the door closed behind him, and stepped in front of me.
We quietly headed up the stairs toward the roof. I felt terribly exposed, but also intensely aroused. I was totally naked with a dripping hole in a public stairwell. It was scary but also unbelievably erotic. My naked host with his dripping cock led the way. The door to the roof was locked. He inserted the key, turned the lock, and stepped through the threshold. I followed him out into the bright sunshine.
It was a typical older NYC building rooftop, covered in black paint and with a few square structures built into the top, one being the casing fo the door itself, the other two presumably for electrical and maybe a toolshed. But the most remarkable thing that struck my mind as soon as I stepped out into the open was, it was NOT the tallest building on the block. I was standing with my new bud totally naked and erect, and within clear view of several other taller buildings.
I cautiously walked around, checking out the view. The structures on the roof provided some cover from some buildings, but there was nowhere on the roof where we would be totally hidden from all of them. I started to feel a little anxious. But although I was nervous, I also found it an immense turn-on.
“What do you think?” he said. I looked at him and smiled, and said nothing, but my hard dick took that moment to release a long heavy string of precum that touched the surface of the roof before detaching from my cockhead. We looked at each other for a moment, then he led me around one of the structures where we were still visible to one of the buildings, but at least it was further away than the ones on the other side. “Now, where were we?” he said coyly, while drizzling more lube onto his hardon. I looked him in the eye, smiled, and turned around. I bent over and put my hands on my knees. He stepped up behind me and sank his cock back into my hole.
He continued the languid pace we had been going at back in his apartment. I was facing out toward the building across the way, and I wondered if anyone was looking out their window. Here I was, buck naked on a rooftop in the middle of Manhattan, just a stone’s throw away from Central Park, with my ass full of cock. The fear of getting caught was sky high, but the eroticism of the situation was even higher.
He started to pick up the pace. He was going at a good moderate clip now, fucking me deep and hard. I was rock hard and my precum was forming a small puddle underneath me. His cock inside me felt fantastic, and my worries about the risk of the situation fell back into my subconscious and I started to meet his thrusts, driving his cock deeper into me.
We were going at it like this for about 15 minutes, then I felt him really pick up his pace and drive into me harder. He stiffened, and then I felt him start to unload. He came hard, filling me up with his semen. I wasn’t really close yet, but I consoled myself with the thought that the experience was hot enough, I didn’t need to cum. As if reading my mind, he pulled me into his chest, his cock still firmly up inside me, and whispered, “Don’t worry. I’m good for another one. But we’d better head down and get back inside. I’ve never been up here this long before. We don’t want anyone to call the cops.” I missed his cock as it slid out of me.
He picked up the keys and the bottle of lube. He headed toward the door, and I padded along on my bare feet behind him, his cum beginning to leak from my still-horny hole. Still rock hard and incredibly aroused, I walked past him back into the stairwell as he held the door for me.
As I crept down the stairs in front of him, I became slightly self-conscious as I felt his seed begin to trickle from my open hole down my leg. I stopped in front of his apartment door and waited for him to catch up. I felt his hand on my inner thigh, and I turned around. He had gathered up some of his semen, and proceeded to lick it off his fingers. With a devilish grin he pulled me into him and kissed me, pushing his tongue into my mouth. I could taste his sperm on his tongue, and my cock jumped in response. We stood there kissing, naked in the hallway, for a few minutes.
Suddenly we heard a door open a floor above us, and the sound of someone coming out into the hall, and then the sound of a key being inserted into a deadbolt to lock it. With an impish grin he turned, unlocked the door, and we scuttled inside just as the person above started down the stairs. What a rush!
Back inside, we took a little breather. He pulled out two fresh beers from the fridge, our first ones sitting unfinished and warm where we left them as the action started. He offered me a hand towel, and I mopped up his sperm from my leg and my ass as best I could, and sat down on another towel he’d placed on the day bed. We made small talk and sipped our beers for a few minutes. After about 10 minutes, he got up, walked to the kitchen, and took a washrag, ran it under some hot water, and began cleaning up his cock. “Ready for round two?” he asked. It was an unnecessary question, as my cock hadn’t softened since we came back downstairs. “Sure!” I answered back.
We got back into our 69 on the day bed. I appreciated his thoughtfulness in wiping down his cock before I put it back in my mouth. (Of all my kinks, ATM is not one of them). As I sucked on him, I became fascinated by how large the head of his cock was compared to the rest of his penis. I began to concentrate on just that fat head, licking it, kissing it, sucking it, trying to work the tip of my tongue into his piss hole. Every so often I’d take him all the way down, plunging his cock down my throat, and eliciting a deep moan from him as he deep-throated my cock at the same time. Then I would go back to concentrating on that bulbous cock head.
This went on for a while. After about 15 minutes or so, his mouth found my fuckhole again, and he began to rim me out. I took this as a signal that he was ready for more fucking, and I eagerly gave his cock some last minute deep throat action, tasting his precum on the back of my tongue.
He got up and pulled his cock out of my mouth, then picked up the bottle of lube and began oiling up his cock. “Want this cock in your hole again?”
“Yeah,” I answered.
“Yeah, what?” he asked.
I caught on. “Yeah, I want your fat cock up in my tight, hungry hole again. I want you to fuck me.”
“Aw, what’s the magic word?”
I stifled a giggle, but I went with it. “Please, please shove that beautiful cock deep in my fuck hole.”
He smiled. “Come take a look at the view,” and he gestured toward the open window.
This seemed a bit of a non sequitur to me, but I walked over and looked out the window.
“No, really look. Look OUT the window.” He gently pushed on my shoulders so that I bent over and put my head actually out the window. We were on the second floor, and as I looked out, I realized that second floor isn’t actually that high. There were a lot of people milling about on the street not that far below, and if they were to look up, they’d see me at the very least shirtless hanging out the window, and if I leaned a little further out, they’d know that I was naked. If anyone happened to look out their window from the building across the way, they would be able to see it all.
“Yeah, just like that.” And I got it. His thing was public sex, and he wanted to fuck me in a way that would expose me to anyone who might be astute enough to take a look. My initial shock at this thought gave way almost instantly to a feeling of erotic excitement and expectancy. I was ready for this. And though I hoped no one would see me, the thought that someone might made my cock jump. I found the risk factor a major turnon.
“Just keep looking out the window,” he said as he stepped up behind me and began rubbing more lube into my hole. It was hardly necessary as my hole was still slick with the lube and his semen from our earlier session, but I enjoyed his fingers lubing me up nevertheless.
After a moment or two of this, I felt his big cock head pushing into my welcoming fuck hole once again. I involuntarily moaned in pleasure as he slid into me. “Shhh,” he said, “or someone will hear you and look up.” Then without warning he pulled back and shoved into me hard, driving my entire naked torso out the window and eliciting another deep guttural moan from me. He stood still, his cock impaled deep in my ass, and laughed quietly. I laughed along with him. I found that the risk was something I enjoyed as well. The chance of being caught added greatly to my sexual excitement.
My cock was rock hard and leaking profusely as he started fucking me in earnest. I did my best to stifle my moans and grunts, and watched the unsuspecting people walk by below, oblivious to the sex that was going on just above their heads. I occasionally glanced across the way to see if I could see anyone watching from out their window, but I saw no one.
He continued to plow into me, and I found it more and more difficult to put a damper on my vocalizations. He was really hitting all the right spots inside me. My raging hardon was profusely drooling its precum like it was a leaky faucet. He was going to push me over the edge without touching my cock. I felt my orgasm building, getting closer and closer as he drove his cock into me again and again. I couldn’t help it and let out a loud “Aaaarrrrrrrrggggghhhhh!” Suddenly a little fearful, I looked down, but no one had seemed to notice.
“You’re going to make me cum,” I whispered behind me.
“I’m going to cum too. Get ready.”
He picked up the pace and began fucking me like a mad man. I met his thrusts and drove my ass back into his cock as he drove forward, holding back my cries of passion and sexual ecstasy.
“I’m gonna shoot,” I said, a little louder than I meant.
“Go for it,” he answered through clenched teeth.
He started pounding into me harder yet, and then it hit. Neither of us had touched my cock since the moment I started bending out the window. He was literally fucking the cum out of me. I was unable to stifle the first nonverbal cry that tore from my throat as the first jolt of orgasm hit me. I shot hard. The first shot actually arched up and flew out the open window onto the street below. The rest covered the window sill as I struggled to keep my footing while I ejaculated with his cock still driving into me.
Before I was finished shooting I felt him start to unload inside me. He pushed all the way in, and held me in place as he pumped another huge load of semen up inside my ass. His orgasm seemed to go on forever. I could feel him pulsing in my hole as he dumped his load.
“Don’t take it out,” I whispered to him. I wasn’t ready to let him leave my hole devoid of his cock.
“Come back in side.” I stood up, and he hugged me into his chest, his cock still deep in my chute. We scuttled backwards to the daybed, his cock in my hole, and he sat down slowly on the day bed so I could follow his movements and we could keep our connection going. His cock was still mostly hard, and he took a few strokes into me as I absent-mindedly rode up and down on it.
“Damn, that was good,” I said. “Fuck good, that was spectacular. Thanks.”
“Yeah, we seem to work pretty well together,” he answered. “I wasn’t sure you were going to go for the window stuff, but I decided to try it after our session on the roof.”
“I admit it threw me for a second, but damn! I was so turned on.
We stayed there, me sitting in his lap with his cock in my hole, until his cock finally got soft enough that it plopped out of me. If anything, this load had been bigger than the first, and cum ran out my hole, coating his genitals and puddling up on the towel we sat on.
Encouraged by how well this first session had gone, we made plans to hook up again.
“Every been fucked in Central Park?”
“No, can’t say that I have.”
“Do you want to be fucked in Central Park?”
“Fuck yeah. Do you think we could get away with it?”
“Easy. I’ve done it before. I’ll show you the best places.”
“Sounds good. I’m looking forward to it.”
We had spent the entire afternoon, and I needed to get going. I made my goodbyes and started to reach for my clothes.
“Hey, before you go, I wonder if you’d indulge me in one of my little kinks.”
“Sure,” I answered, “if I can. What were you thinking?”
He walked over to a small table to the side of the window with a drawer in it, opened the drawer and took out a medium sized butt plug. “It’s a good one. Medical grade silicon. I want you to have it. Kind of a parting gift.”
I laughed, and said, “not sure we should be sharing sex toys.”
“It’s never been used. A buddy of mine gave it to me but I never used it. Will you take it?
“Okay, sure.”
“But I want you to take it home inside of you. I want you to put it in your ass right now.”
I laughed. “Seriously?”
“Yeah. It will hold my cum inside you until you get home. That would feed a big fantasy of mine if you’re willing.”
I laughed again. “Okay, but you have to put it in for me.”
I bent over the day bed and offered him my ass one last time. He put a light coating of lube on the plug, then gently eased it into my hole. “How’s that,” he said.
“Feels good. Your little swimmers will live on for a few hours more before I release them into the New York City sewer system.”
He laughed. “Thanks. That’s a big turnon for me.”
My ass was still wet so I dried off around the plug as best I could with paper towels and pulled my shorts on. I carried the shirt. I walked to the door and slipped on my flip flops. He followed me and turned me around and kissed me.
“Until next time, then.”
“Oh yeah, there will definitely be a next time, I answered.
I headed down the stairs, my ass full of sperm and a butt plug, euphoric after one of the best fucks of my life.
We had several other adventures after this initial meeting, including the fucking in Central Park, but I guess those are stories for another day.