First Time Gay Runs Wild

As a middle-aged man with a divorce behind me and a newly found openness I had begun to explore my fascinations with gay sex.

Throughout my marriage my ex and I had explored lots of things together but never got beyond the talk when it came to me and a guy. Our sex fantasy conversations had developed many scenarios and, at the time, I had felt that it might happen, that a casual meeting in a bar or an old ‘friend’ of hers, or some other circumstance would lead to another man in the bedroom for us to share. But it never did, and my slowly growing urges had to be satisfied by her teaching me how to blow her dildo, her filling my mouth with my cum that had just filled hers and her slowly teaching me how to take her pegging.

I loved it all. To this day, were we to ever hook-up again, I know it would come up and she’d be fascinated to know, “have you?’ she’d say, “have you sucked a real cock?”

But that won’t happen, and she’ll never know what has.

What did happen was both scary and so exciting. It happened in stages over the course of a couple of weeks and started with a normal hook-up with another man. We’d met on-line and while the undercurrent was definitely sexual, I’d been open with him before we met about my inexperience.

We met at a nice, dark restaurant and sat chatting at the bar. Sharing our stories, opinions, and beliefs, talking politics one minute, football the next. The three or four drinks we had certainly loosened me up so when he invited me to his place for the next drink I said “sure, I’d love to.”

I followed him for no more than a mile into a lovely neighborhood on the intercoastal. The house was what you’d expect in an expensive subdivision; a beautiful Florida ranch with cool tile floors, lots of windows and a pool that was lit in that dark, sexy, party way with the sensual glow of the pool lights.

We sat in the patio chairs, and he told me the story of the house. Until his divorce he lived there with his wife but when they split, he was able to keep it.

Julian got up and said, “sit tight, I’ll fix us a drink?”

A minute or two later I heard him come back and he placed two drinks on the table next to me, leaning over from behind me. He stayed there for a second and then touched me, in what I could tell was an “invitational” way his hand rested on my shoulder and, sensing no objection, he slowly massaged my collarbone and moved his hand gently down my chest. I just sat there, did nothing, gathered my thoughts and enjoyed it. I knew that this would be the night, the night that I’d hold and touch and suck a cock, after all those years of fantasy and talk, I would soon know what it felt like to take a cock in my mouth.

And it was sooner than I thought. He walked around in front of me picked up our drinks and toasted “to new friends”. I took a sip of my drink and leaned forward, his crotch not even an arm’s length from me. I moved to edge of my seat and ran my hand over his cock, and slowly unzipped him. I wanted his cock in my view, I wanted to take it out and touch it, so I undid his belt, his buttons and gently, with a little help his cock and balls were free. He wasn’t hard yet, but I sensed there was some excitement there and, for a moment I just looked, I stared at the head of his cock with its lovely soft, shiny skin, at his balls that looked so plump and cleanly shaved and leaned in. I wanted to do nothing but open my mouth and feel that cock so I didn’t touch it, I just moved forward onto my knees, I placed my hands on his hips and opened my mouth to take all of it in.

For what seemed like, at the same time, both an eternity, and a fleeting few seconds, I learned how to give a blow job. I don’t know if it was a good one or not and frankly, I was less concerned about his pleasure than mine. How can sucking someone’s cock be so enjoyable? Why did I not learn this sooner? How can I do this again. I want to do this every day!

It wasn’t long before we were completely naked, outside in the humid Florida night. Kissing and sucking and stroking. “Let’s go to my room” he said. And we did, the chilled air feeling great on my naked body, as we climbed on his bed, he laid down and I laid on top of him. It struck me as odd for a moment that this was just the same as laying on a woman as we kissed so passionately and ran our hands over each other, feeling our cocks hard against each other’s. We romped around for a while with so much oral sex and ’69’s but never once did I feel as though that was enough cock in my mouth. I wanted more.

I rolled on my back, at his request, and tipped my head over the edge of the bed. “I know what this means.” I thought. I’d done it with my wife so many times and I opened wide so that he could fuck my mouth, at his pace, and be as hard or gentle as he wanted. I loved it, that feeling of submissiveness, of ‘use me’, that opened throat for him to force his cock down. He took it gently to start, slowly fucking my mouth, easing his cock in and out very slowly and deliberately, my tongue wrapping his shaft and feeling each gradual move. The pace went up and down, he got faster and faster and then stopped, only to start slowly again but go further and test me. “How much cock can I swallow” I thought as he pushed himself in all the way, and he stopped, with his balls on my nose and pulsated, throbbed gently in my throat. “Was he cumming” I wondered?

He wasn’t. At least not then. I enjoyed the intimacy, I enjoyed kissing and touching and so enjoyed sucking but what I learned that I enjoyed most was being used. Becoming what would turn out to be a ‘cum slut’.

I slid off the bed and assumed a position that in the coming weeks I would learn to love. I knelt in front of him and sucked him more, but this time I was taking the lead and doing what the girls always do in the porn movies, sucking and jerking, caressing his balls and his ass, looking at his face and saying, “I want you to cum in my mouth”. And he did.

I can’t say that I wasn’t a little scared at the thought of cum being pumped into my mouth. I shouldn’t be, I’ve tasted my own cum many times, mouth-fulls from my wife dripping it in, spitting it in, kissing it in. I shouldn’t be because I’ve cum in many mouths before and never had a girl who didn’t like it. But when the moment came it was great, and it was a lot. I felt the pressure building up, literally and figuratively with the groans and the pace, and when it came, that first fast spurt, I was holding his cock tight with my lips, I felt the pressure release on the roof of my mouth and then I pulled back and held his cock tightly just away from my face, with my mouth wide open so I’d see the second pulse shoot from his cock. It flew across my face and into my mouth, into my eye and hair and then, for the third and final stream I took him back in and let the cum, more slowly this time, fall on my tongue.

My wife was especially good a blow jobs and one of the things she often did was just hold my cock after I’d cum. Not with her hands, but gently in her mouth, she’d let the hardness relax for several minutes in the warmth and softness and move her tongue slowly as the orgasm waned. I did that. I loved it, and after a few minutes I was sucking gently on a soft, worn out, satisfied cock.

The next time we hooked up, a week or so later the fun expanded to real penetration. I’d never been sure about who’s a top and who’s a bottom, or whether you can be both but my sexy ex’s escapades with her dildos had led me down that path. I’d always loved the feeling of her dildo anal play; she’d start off easy with a small one and work up through her collection to larger and larger ones.

After we divorced, I’d bought myself a few to do the same thing. Occasionally I’d have an anal masturbation frenzy; I’d prepare properly and then, over an hour or two fuck myself silly with all sorts of toys. I love the realistic ones and the way they slip in and slowly expand my ass and the completely different way that I get excited. I can do this for hours without my cock reacting ; it’s a totally different pleasure.

So, when we got together the next time, I wanted that, I wanted my ass pounded and wanted to feel his cum squirting in my ass and the pulsing of his cock inside me. Which is what happened, after an evening fueled by a few drinks, hanging around naked for hours and a lot of cock sucking. But it was what we talked about for our next meeting that got me going.

We, Julian and I, met for a drink as we had planned with a few of his friends. I knew the plan, and I knew these ‘friends’ were also fuck buddies, and I knew that we’d end up back at his house. What I didn’t know was the fun and craziness that would ensue.

There was no holding back when, after a few drinks we went back to the house. Two of the guys, stripped down and got in the pool right away and I was fascinated, seeing their cocks swinging around, their openness and casualness. While Julian started fixing drinks I was talking with the others and one of them suggested we all get in and swim. “Oh yes!” I thought, all these cocks, nakedness, casualness, “let’s go!”

The rest of us stripped down dropping our clothes just where they fell, there was this openness about checking each other out, as each piece of clothing was removed, it was almost in unison as we all stood there naked, what seemed like sighs of anticipation, as we checked out each other’s cocks. Or perhaps that was just me; I’d just seen two “new” cocks get in the pool and now, here I was standing in front of two more, the excitement just ran through my body.

We were all in the pool, talking and, I think, playing with our cocks when Julian walked out with a tray of drinks. He’d dressed up! And oh-my it was sexy, kinky and, just wow! He strutted out from the sliding doors wearing heels, fishnets and one of those little very, very short stripper schoolgirl skirts that’s more like a frilly belt than a skirt and so short that his cock was completely visible swinging away as he walked. But that wasn’t everything, the ‘piece de la resistance’ was the tits. He was wearing a set of those silicone boobs, the life like ones, and they looked almost real as they bounced around with his steps, then, as he served us all drinks they swung and drooped almost naturally as be leant forward to hand each of us our cocktail.

“Everyone OK?” he said, standing in a somewhat commanding position at the end of the pool.

We all sipped on our drinks, leaning on the sides of the pool and I, for one, couldn’t keep my eyes off him.

“You bet.” I said, “That is some look, you’re turning me on down here.”

“Well, it worked then.” Replied Julian. “Why don’t you come and feel them.”

I got out of the pool walking up the steps toward him. I could feel my cock bouncing in that half hard way and could see all the guys watching me. I walked up to Julian and cupped one of his fake tits in my hand. It felt good, not real, not warm but the silicone had that nice squishy feel of soft large breasts, I kissed him sexily while my hand slid to his cock and then, in fulfillment of one of my growing series of gay fantasies, I dropped to my knees and took his cock in my mouth with an audience.

There I was, just weeks into my gay sex period feeling a cock grow hard with my improving blow-job skills, naked, with a group of guys watching. It was an exciting blend of exhibitionism, slutty-ness and submissiveness that appealed to me, and each piece was an element of my ongoing fantasies.

I’ve always harbored an exhibitionist side, and my ex used to contribute to that.

There were two things she’d do with some frequency that fueled that fantasy, one was to call me on my drive home and “make” me get my cock out and masturbate while driving. I actually loved doing this and would do it without her encouragement, but when she demanded it, she had expectations. She wanted me to talk to her while I was driving and tell her what I was doing, she’d get excited when I told her that I stopped in some secluded place and walked around naked, or if someone has caught me, another driver or passenger in a taller vehicle perhaps, or someone waiting at bus stop. But the one thing she always insisted upon was seeing what I was doing when I pulled into the garage. Sometimes she’d come out and look through the window or open the door and make me jerk for her. Every now and then I’d be completely naked when I pulled up either because I’d driven that way or, more often, I’d stripped down closer to home. If I’d been especially good, she’d be naked in the garage, perhaps sitting on the workbench playing with herself.

So, being on my knees with this cock in my mouth and an audience was right up my alley and I think Julian knew that.

David, one of the two guys that got in the pool first said “Julian, how come you’re getting all the attention?” as he pulled himself up to sit on the edge of the pool deck. I looked over at him, he was leaning back with his feet in the water and his legs spread apart, his cock right there at the edge of the deck. I looked up at Julian, his cock still in my mouth, and he smiled a knowing smile. So, I did it. I slipped back in the pool and over to David and, without a word I picked up his cock and slowly started sucking him. He was big, as he got harder and harder in my mouth, I realized that giving good head to a bigger cock is going to take some practice. I took it slowly, keeping the head of his cock in my mouth and running my tongue all around it, gently squeezing the shaft and jerking him slowly, cupping his balls in my other hand and boy, did it turn me on.

Then, I felt one of the guys come up behind me. The first touch I felt was his hand on my shoulder, the second was his hard cock between my legs, he started to move his hips pushing his cock back and forth between my legs, up against my balls, and, on each forward thrust I would feel his body up tight against my butt. He paused, stroked his hand down my back, across my hips and grabbed my cock, first with his right hand and then his left, one on my cock and jerking, and one gripping the base of my shaft, and, at the same time, he moved his cock into my ass crack and slid up and down, up and down.

I couldn’t process all these sensations, what he was doing to me and what I was doing to that magnificent cock.

“You know,” Julian said, “I think he should suck all your cocks guys, let’s get lined up for him.”

And they did. To start, they all sat along the edge of the pool, except for Julian who pranced up and down behind them squeezing his fake tits and swinging his cock. There they were, one cock after another, and I worked my way through them all. To start, I focused on each individually, giving just a little head and feeling the different shapes of each hard cock, as I sucked each of their glans and stroked the shafts of each of these four cocks. I loved the differences, their different thicknesses and shapes, the tastes and the looks on their faces as I sucked them. Some guys seemed quite intense when we made eye contact, others more dismissive, but I loved it all. I took to using my mouth on a cock and my hands on two others, oh my, the feeling of three cocks in my grip!

I wasn’t getting tired, perhaps my mouth was a little, but I could have gone on like this for a while, but Julian had another idea.

“Don’t you think I deserve more.” he said. “Get that cock-sucker up here for me.”

So, out of the pool I got and walked over to him. I knelt down again and took him in my mouth again, reaching up and caressing those magnificent plastic titties. The guys crowded around, hands all over the place, jerking each other, reaching under my ass and playing with my balls, slapping my face with their cocks.

“I’m surrounded.” I thought, with cocks everywhere as I moved my attention from Julian to the next cock, and then the next, and immediately I found myself bobbing from one to another to another, a few seconds on this one, a few more on that, all the time, grabbing for cocks with my hands and seeing the others being jerked by whatever free hand was close. The energy was rising, and not slowly, we seemed to go from casual to frenetic in seconds and then it started.

“I’m going to cum.” said David, “open your mouth.” As he jerked his cock in front of me. And he did, pulsing a long string of cum with his first pump that shot right into my mouth, then a second, a third, a fourth, each one with what seemed like equal force, in my open mouth, across my face, and dripping down my cheeks. Then it started, the next one was forced into my mouth, I engulfed that throbbing cock completely and felt those semen explosions in my mouth pulsing cum to the point when I couldn’t take any more. Then another and another until my face was covered and I’d swallowed what seemed like 3 mouthfuls. I sat back on my knees and just breathed, licking my lips and tasting them.

“I am a cumslut” I thought to myself. “And I love it.”

With that normal “post-cum” calming we all sat down and relaxed, Julian teeter-tottered off in his heels and bouncy tits to get more drinks. They proposed a toast to the new “cum dumpster” and we drank to my new-found cock-sucking, facial taking and cum drinking appetite. If felt good to be the center of attention and to be complemented. I began to think I was pretty good at giving satisfaction. We all relaxed and talked and chilled, but I was sitting there with a rock-hard cock and they weren’t.

“Look at him” David said, “Our little slut is feeling horny.”

And I was. All that activity had left me throbbing and I’d not received any attention. David got up from his chair and came to me, he leaned over and touched me, pulling my cock slightly and then got to his knees and started sucking. He bobbed up and down slowly and then paused to say, “don’t cum until we’ve all tasted you.” He licked his way up and down my shaft, slowly and rather expertly sucked all my cock into his throat. He was good, “Perhaps he could be my coach?” I thought.

Then he backed off and returned to his seat. “Guys,” he said, “I think he needs to do a tour of all of us, let us all have a go.” They all agreed and moved forward to the edge of their seats and beckoned me to give them my cock. I went around to each, and they opened their mouths to receive me, for a few short seconds, for a gentle suck, for a hard pumping “I want to make you cum” suck, and then it was Julian’s turn. He took me in his mouth and slowly sucked on me while lifting those wonderful silicone tits. Even though they we plastic they turned me on. He played with the nipples, and gently slobbered up and down my cock, then his hands went to my thighs and my butt. He spread my cheeks and gently stroked my asshole, oh my, what a sensation.

“You’re going to make me cum” I said and as soon as the words came out I did. I pumped what felt like a whole week’s load into his mouth, the first powerful pump resonating through my whole body, and then a second and third and all consumed in his mouth, not a drop spilled.

And not a drop swallowed it turned out. After releasing me he walked me to the back of the outdoor sofa and bent me over it so that my ass was up in the air, he spread my legs and proceeded to let all my cum drip out down my crack to my asshole. I could feel the warm cum dribbling down as he spread my ass cheeks apart. His hand stroked up and down my ass rubbing the cum everywhere his finger gently painting a line down my crack, across my ass to my balls, and with each pass he pushed the tip of his finger, just ever so slightly, into my asshole. The sensation heightened and the little pushes pushed further, I knew what he was doing, he was adding just a little lube each time, I could feel it’s effect and how different it was to my stick cum. The penetration gradually became the focus, and his fingers stretched my ass just enough to lube the inside, and then the fingers changed. No longer the boney feel of one, then two fingers in me, instead, the smooth, hot hard feeling of the tip of his cock. He pushed gently allowing me to stretch comfortably, as he slid the head of his cock in me. It felt wonderful, I gripped it a little and readied myself for his slow deep sinking of that cock.