Surprise Night with a Guy named Joe

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Looking fun, goes has his first experience...
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It was an average Friday night for me. A little bored and rather horny. Not just any horny, more of a ravenous, down for anything kind of horny. Not having anyone in my life at the time and not really wanting to masturbate, I decided to turn to good old Craigslist (back when that was a thing). I honestly didn't think much would come of it when I posted a rather bland and in retrospect, rather cheesy and generic ad.

"BM, 5'6" fairly well endowed, looking for someone, HWP or BBW, on the northside looking for some weekend NSA fun."

Like I say, I don't even think I was half serious when I posted that and went on to something else. But about 30 minutes later, I had an unexpected response in my inbox.

"Not BBW, WM, northside, looking to have some fun...if you're into something a little different."

Now, of course I knew what WM stood for. Perhaps some days, I would have been like, "Well not really into guys, but thanks." But tonight was different. I was honestly bi-horny. I had never given the thought of being with a guy much of a serious thought before. I had played with my own ass a few times while masturbating, and it felt interesting and sometimes good, but I wasn't sure if it was something I wanted to do more.

But a horny mind is a singular focused mind. When I thought about my fantasies, and sensations that I wanted to experience, they didn't necessarily involve just being with a woman. And I was indeed curious. I had heard and read all the cringe-worthy things before, like, "A man knows what a man wants", and "I have my secret cumdump that does things with his mouth that have me seeing stars." What if that's what it's really like? I honestly didn't have anything to lose as long as I was safe about it. And I am not the type of person to want to die one day kicking myself with regret, especially when it comes to sex.

So I replied, exchanged some details, and it turns out that he literally lived by himself about 5 minutes away from my house. He basically said, "I have a few beers and can't (shouldn't) drink them all by myself. Why don't you come over and have some and what happens, happens. No pressure."

I found myself getting quite aroused. There was a stirring in my pants as I touched myself. I was indeed aching for release, and this was seeming too good to be true. I didn't know what Joe (yes that's his real name) wanted to do, but I was going to find out. Before I changed my mind or chickened out, I replied and told him I would stop by around 10pm.

While in the shower, I did take a minute to explore my body. I had freshly shaven everywhere, because I don't really like body hair and thought about what it would be like to feel another hand on my cock.

Was it different to have a guy's mouth on me?

Would the excitement and newness make me explode?

Would he want me to suck him, and would I be good at it?

I had so many questions, but one thing was definite. My biggest fetish and turn is the orgasm itself. I loved getting someone else off, whether it be with my dick or my mouth. Watching their body convulse uncontrollably, the moans, the curses, the grunting...that was the greatest thrill. The more they came, the greedier that I got in my attempts to bring pleasure. To me, that was just as good or better than my own orgasms. I snapped from my reverie when I realized that I had stroked myself almost fully hard. I sure didn't want this show to be over before it even started.

I will admit I was a little nervous when I walked into Joe's place. A small quaint bachelor's pad, everything was immaculate and there was a scent of some sort of incense. It was obvious to me that he was the type that entertained "guests" but lived alone. Even though I wasn't attracted to men in a "Wow he turns me on" type of way and never had been, Joe was an attractive guy. Fit and tan, he stood a couple of inches taller than me. He had cropped blonde hair and a chiseled jaw. Wearing just a white wife-beater, a pair of boxers and socks, he clearly made it apparent what he was looking to do, without having to say anything. I would find that out about him in much more detail later on.

We made some small talk as he showed me his place and his art collection. He was true to what he said as in no pressure. When I look back on it, he knew that I was "inexperienced," and I think he loved that. After a couple of beers he said, "Why don't you get comfortable."

It was a really cold day that day, but all I had on was a heavy fleece pullover, a pair of sweatpants and underwear.

"Well," I said, "I'm most comfortable naked." I quickly and not very seductively took off all my clothes, and this was really a moment of awakening for me. Here I stood, stark naked in front of this strange man, and my mind and body was on fire in a good way. Perhaps it was the way that he looked at me. His face was an expression of hungry greed and smug satisfaction. Here I was before him, naked and completely vulnerable and he hadn't lifted a finger or said a word to convince me. I knew then and there who was going to be calling the shots, and I honestly never felt better about it in my life. I knew he was going to do things to me, and I was going to let him.

"You have a nice body," he said. Leaving his shirt on, he dropped his boxers to the floor and stepped out of them. "Do you like what you see?"

"Yes, yes, I do." I didn't know what the hell to say. "You have a nice dick", would sound so childish I wouldn't dare. But he did though, as far as the dicks I had seen in porn or in the locker room go. I estimated about 6 inches and pretty girthy. He was shaven like myself, but he had much larger balls than mine. All of my thoughts were completely dirty now.

What if he wanted me to suck him?

Would it gag me if he shot his load in my mouth?

What if he wanted other things?

All of these thoughts were rhetorical, of course. I was going to do whatever I needed to get him off.

"Why don't you have a seat," he said. I did as ordered and he took my now semi hard dick and started to stroke me. My rational mind of course knew that it was just a hand, but the thought of it being this strange man manipulating me made it feel much more intense. In a move that made me audibly gasp, he took half of me into his mouth without warning.

"Oh fuck," I said as my back arched uncontrollably. My toes curled as he moved his mouth up and down my shaft, never letting his lips lose their grip. I wasn't sure how long it was, as my eyes were clenched tightly and my breathing was ragged as I felt myself start to swell in his mouth. I was snapped to my senses when he released his mouth from me with a pop.

"Don't come yet..." he said through wet lips.

"But, how did you know?" I said, almost pleading.

"I've sucked a lot of cocks in my day. I know exactly when to stop. I kinda like to control the action."

"I can tell. I guess I have to do what you want?" I wasn't really asking, but it sounded better than saying what I was really thinking out loud. I know now, I was entering what in the BDSM world is called subspace. I wasn't interested in being in charge at that moment. I wanted to be objectified and ordered. I wanted at that moment to be used as a pleasure object, nothing more and nothing less. I didn't have to say it because he knew it. Joe would tell me later that my almost non-existent resistance was something I shouldn't be ashamed of, but he was just that good. Joe was a nice guy, but he sure was arrogant.

Joe nodded and stood up, his semi-hard dick near face level. I had never been that close to another man's penis before. It stood there, brownish pink, with thick veins and a perfectly shaped head, just inches from me. It wasn't nervousness that made me hesitate: It was excitement and I had to take a moment to look at it. I mean, we had the same parts of course. But everyone is unique. Would his member react the same way mine did? Would he cum quickly in my mouth?

I didn't want to keep him waiting though, and I sensed that he wasn't going to order me to service him. He was going to make me want to do it. I took his balls in one hand and gently moved him a step closer. I could feel the heat as I pressed my lips on his glans and kissed it, then opening my mouth took his head inside. It was indeed hot, and both firm and soft at the same time. It was electric to me, doing this for the first time. My anus quivered and my own cock flinched as I slowly went deeper down his shaft.

There was no stopping now, I was mesmerized by having this little semblance of control, although I wanted none. I could tell that Joe liked it as his hips gyrated very slowly pushing deeper inside my hungry mouth. When I came up for air his now rock hard cock had a line of my spit mixed with his salty precum on my lips.

"Do you like that," I asked, almost meekly.

"You're doing great," he said. Something in me was seeking his approval, and I smiled. "Let me sit down."

We traded places and he sat down with legs spread out, his dick standing at full attention. I knew my place, so I got down on my knees. I was surprised that it came so natural when I ran my tongue up and down the thick cumpipe, going ever lower and licking his heavy sack. I knew enough from my own anatomy when I ran a finger along the hard engorged ridge of the perineum that I was doing well.

All inhibitions were lost as I took him back into my mouth, sucking and spitting. I wanted to take as much as I could in my mouth. Forming a ring around the shaft, I gauged how deep in I was inhaling him. 2 inches, then 3, then 4. When my fingers were resting nearly on his pubic bone, I knew I was almost there.

And then it happened. I took my hand away, and pushed hard, but the tip of his dick touched my throat and I gagged. It was a dry heave, but I lurched back coughing.

Through watered eyes I said, "Oh god, I'm sorry..."

Joe shushed me quickly. "Don't be sorry. That was so hot. You are a good cock-sucker. Do you like sucking cock?"

I nodded, wiping my lips. "I like sucking you. Do you want me to finish you? I think I can..."

Joe thought for a moment. "Well, that's an option. But a better option would be to leave that up to you. What do you want?"

I knelt with my butt on my knees and looked down. My semi-hard dick had a long line of clear juice dripping down onto my thigh.

My words came almost robotically and without thinking. "I don't think I can finish you with my mouth, but I can give you something else."

Joe looked at me. He knew what I was saying, but he just wanted to hear me say it. It was all part of his mind-game, and I without any hesitation or shame went right along with it.

"I want to get fucked. I want you to fuck my ass."

Joe smiled. "Ok. Wait right here."

He went into his bedroom and returned with a condom and a small bottom of lube.I wasn't sure what he wanted, though. Did he want me to bend over, or lie on my back? It was an admittedly tense moment. Not for some real fear of what was to happen, as I had played with my own ass a few times before. The sensation wouldn't be a foreign concept, but it was totally different when it was another person.

Joe answered my question by laying down on the carpeted floor. "I want you to ride it," he said, handing me the bottle of lube after smearing a generous portion on his condomed dick. He truly was masterful in making someone feel safely dirty. He even had me lubing my own slutty asshole without question.

He watched me intently as I straddled him, ass in the air and applied the cool lotion to my rim. I know he heard my audible gasp as I slipped a finger inside myself to make sure that I was fully prepared. Once done, I took one hand and guided his tip towards my entrance.

"That's it..that's it," he growled, "Take it in there."

With a deep breath, I pushed down, feeling his hardness push against me. Although well lubricated, there was resistance, of course. As I eased down, it was a sense of tension and release at the same time. Vulnerability was building in my mind, washing away many, if not all rational thoughts. Joe took one hand and started playing with my now wet and almost painfully sensitive glans. He knew what he was doing. This wasn't his first time taking a newcomer's ass. He knew that the stimulation would make me yearn for more, my senses laser focused on the itch that needed to be scratched.

"Oh fuck....." I said as his head finally pierced the inner ring of muscle and the fullness of my hole being stretched set every nerve fiber in my body on fire. There was no rational thought to be had. What I had read about the first time you did this was true: When there's a dick in your ass, you're both absent and present at the same time. It's just your ass and whatever that cock wants to do with it.

The copious lubrication made it rather easy for me to slowly ride myself all of the way down until I was almost sitting on his thighs. There was a hint of pain but it was worth it, as every upstroke sent a powerful jolt through me as his thick cockhead pressed against my prostate.

"That's it," he said, "Massage yourself." And I did, my hips bucking as my moans grew coarse and ragged. I could feel every inch of him as I ground back and forth in uncontrolled twitches while alternating with up and won strokes to massage him.

Joe was loving every minute of it as my body writhed. He had such a smug grin on his face knowing that my body had turned into a sweating sleeve for his cock that I would have been angry if I had not succumbed to this new and previously forbidden avenue to satiate my lust.

"Don't cum yet.." he kept saying over and over as he throttled my orgasm by stroking my now complete mess of a penis to increase my pace to where I was right on the edge and then stopping. My assertive moans and devolved to pleading. This seemed like it went on for hours, even though I knew it was not nearly that long. My legs were getting tired though, and I was sweating profusely, when I said to him, "I don't think I can stay up here much longer. Can I get on my knees?"

"Yes," he said, "I'm getting close too.."

I still remember what I said as if it was yesterday. "Please Joe, promise you won't stop fucking me till you cum?" Part of me wished he would take the condom off and just fill me with his load, but I knew better than that.

I eased myself off of him, my sphincter slowly closing shut, a moment of pause before it would be happily invaded again.

Joe went to the bathroom and retrieved a towel which he placed on the floor. It was quite understandable, as my cock was now leaking fluids like a slightly opened faucet. He didn't want a messy floor.

I was proud of how dirty I felt as I got down on all fours, presenting my hungry anus to him as I served no other real purpose. He had little resistance as he entered me once again. Getting down on my elbows to get the best angle, I said, "Punch me, punch me hard.." That's how it felt, him thrusting hard into me, each stroke a thud landing against my open buttcheeks as I felt his balls slapping against my taint. The experience was unexpected. I could feel the familiar sensation of all of the muscles in my midsection tense as one reaches the point of release and ejaculation is imminent, but it never came. That is what I know now is the difference when you are being sodomized, and its appeal. The person that is inside you can keep you there, on the edge, for as long as they want to.

I knew it was reaching a crescendo when he took one hand, then the other and gripped my hips tightly. I could no longer move and I felt him swelling as I felt him stiffen. I was surprised by the increase in girth as he pounded. It almost hurt because I was stretched so much. Almost.

"Fuck me Joe, get off in me," I said.

"Are you close," he replied.

"Yes! Yes! I think so, I can't tell, it's so intense."

"Ok...here...we go.." Joe took one hand and gripped me tightly, stroking my cock. He was hunched over me as he dug deep inside me. I could feel his breath on my back as his cock bulged like never before and one last thrust before he grunted and released.

"Joe, I'm cumming!!" This is a sensation I would never forget. It was a good thing that his place was secluded as it surely would have disturbed neighbors. My howls and screams were deafening my ears as cum spurted from me, more than I could ever have imagined. Only Joe's tight grip kept me from flailing violently as the uncontrolled firing of the full-body orgasm consumed me.

"Keep going," he whispered as he continued to milk away at me.

"I...can't..can't stop," I managed to say, as my anus reflexively tightened and fought for a control that it did not have with him still inside me. Each twitch of my hole, of which I could feel every millimeter made my cock try to expel more juices until I finally ran dry.

I panted and looked down at the dark towel which was now streaked with row after row of grayish white spunk, the amount of which I had never seen outside of porn. His spent cock softened and he eased out of me. My hole slowly closed, regaining its composure even though my mind had not. While he went to the bathroom to get another towel for both of us, I knelt there on all fours wondering how I should feel.

The rational mind thought that perhaps I should feel ashamed or maybe confused, but I felt neither. I felt dirty, objectified, and proud. Proud that I had fearlessly given into carnal lust and gotten this stranger off with just a couple of open holes and an open mind.

He had cleaned himself up and put back on his boxers as I cleaned up as best I could and dressed. I didn't even bother wiping my ass, such an unrepentant anal bottom I had become. I wanted to feel used on my drive home.

Joe offered me another beer, which I thirstily accepted.

"Did you like it," he asked.

"Yes, a lot more than I expected. How did I do?" Why was I asking him for approval? I didn't know why.

"Well," he said, "You surprised me. I honestly thought you might now want to go that far."

He was goading me into admitting that I hadn't planned to either, but I offered no resistance. "Honestly, I didn't think I would either," I replied, "But once I took my clothes off, I knew that there wasn't much I wouldn't do."

He laughed, "We all get that way sometimes, man. Would you do it again?"

That was actually a really good question. I didn't know the answer, not completely.

"Joe, I'm not sure. I don't know if I could, well you know..ask for it."

Joe smiled that ready grin again. "I know what you mean. Sometimes it's easier when you just don't have to ask, don't you think?" And in that moment I knew he was right. I wasn't into asking for it. I was into giving it.I liked being penetrated, not negotiated into it.

"Yea, you're right." I could see out of the window that dawn was approaching. I had been there a lot longer than I expected to be. "Well I guess I better get going."

"Cool,"Joe said, "What are the chances of me seeing you again."

I smiled at him and held out my hand. "Well, I don't make promises. But I do get horny sometimes."

He shook my hand heartily. "I like your answer to that one. I'll see you around."

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SeasonedSailorSeasonedSailor8 months ago

I relish the time I could have with this guy!

MarcLuciFerMarcLuciFer8 months ago

Great story, it captured the thoughts and feeling of first-time gay sex perfectly. Everyone should have a guy like Joe be their first.

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