tagGay MaleMy First Penis

My First Penis


The title of course is misleading; my first penis continues to be my own. This tale barely mentions my second, which belonged to my teenaged wank-off buddy Lenny, as both of us messed around with each other as horny, small-town adolescents.

But somehow "My Third Penis" just doesn't make for a captivating title, however accurate it might be. The adjective "first" does cover just about every other aspect of this event, which happened some forty years ago in a vastly different sexual climate.

I had had a rough first semester at university and had saddled myself with not one but two incomplete papers to finish or else I wouldn't get credit for those Fall term classes. Both professors were profoundly unhappy with my written efforts, their comments on my papers scathing. A lot of reworking was required.

I had gotten accepted into an elite university and was in over my head. My mental skills were plenty good, but the wealthy, private-school educated students were so much better prepared for academic work than I. My confidence was shaken. The papers loomed. Failure was not an option.

It was January and I knew if I stayed at home that all manner of distractions would intrude, and I would have a hard time getting things finished. I needed quiet and solitude to focus, apply myself, and lick my wounds. I had a month before Spring term began.

So I found a room to rent on Martha's Vineyard, the nearby island off Cape Cod near Boston, with cheap off-season rates and island isolation to complete my academic tasks, restore my head. My plan was to study and write all morning, then take rambling ruminative walks in the afternoon, then back to work at night.

I allowed extra time to hitchhike to the Cape, and got lucky with a first long ride that took me all the way to Sandwich. The wait for the next ride took awhile, but finally a sleek Audi, then a rather rare sight on the roads in the USA, picked me up, and the driver said he could take me right by the ferry terminal at Woods Hole. Perfect.

Older guy, maybe retired, he wanted to talk. This was part of the bargain. You got a ride, you followed the driver's lead. If the driver was a young buck with a Dodge hemi, you made sure to compliment his car, and he would go on for hours telling you about the cam he installed, how many horses it had, top speed, ad nauseam. Whoever was charitable enough to give you a ride, you talked about whatever they wanted.

Well dressed, car clean and elegant, he asked about me, my university studies, dreams and ambitions, and so on.

As the trees along the side of the road sped by, I found myself answering more and more questions about my girlfriend. Initially innocent, the questions gradually got more specific. Was she pretty? I thought so. How long had we been together? Six months. Have you two make love yet?

I held my breath and looked over at him. Middle-sized, no taller than me, fairly trim, close-cropped gray hair, clean-shaven, sharp blue eyes. He looked back. Well?

Not exactly, I answered. He laughed. Anyone, ever? No, I stammered, completely embarrassed by my virgin status. Well, how far have you two gotten then? Her hands felt your penis yet? Yes, I said softly. To climax? I squirmed a bit but couldn't find a way out of answering the direct question. Only a couple times. Did it feel good? Damn yes.

Just his asking made me think about Marla's fingers running along my erection one night a week before Christmas, the smile of enjoyment on her face while she pleasured me, then the sight of the gooey mess left all over her hands.

I was growing uneasy but my answers to all these queries had animated him, and I was relieved when he decided to carry the conversation from there. He described sex with his first girlfriend. Lot harder for us than you guys these days, he confided. Girls felt like they had a reputation to preserve. It was murder to try to get into their shorts. I told him that some of that hadn't changed.

Never forget the first time she licked my penis though, he said, eyebrows arching. Your girl do that yet? Almost, I lied. He laughed.

He kept talking. About his conquests, best orgasms, about how his girlfriends progressively grew more inventive and talented over time, usually at his prodding, how he learned to make his erections last longer, the sex intense. How pleased he was when he finally talked one girl into letting him spurt in her mouth and how great that felt, her soft wet mouth and tongue so satisfying that he often then preferred oral attention to fucking.

Sex is the best thing in life, he said, and I nodded, a bit uncomfortable. I had been telling this guy all sorts of private things about myself that almost no one else knew. But it was arousing too, to talk sex so freely, hear about his own exploits.

Then I heard a story about the first guy who had blown him. A long detailed description embroidered with the voluptuous feelings generated in his cock by the guy's mouth, his expert tongue-work, the explosive climax.

I thought my girlfriend was good but this guy was phenomenal, he said. Kept me hard for half an hour and then I blew enough semen to sink the Queen Mary. Guys, they have a dick themselves, they know much better than a girl how to handle a penis. He paused. You ever had a guy do you?

He looked over at me. I am not that big, but I was well built, with strong shoulders and thick legs. Unless he had a weapon of some sort I figured I could take him in a scrap if it came to that. I hadn't put in too many miles as a hitchhiker but knew enough to calculate situations and safety.

My hair was shaggy, my facial hair sparse. It wasn't hard for him to know my penis was erect from all the sex talk. I shook my head.

He reached over and I held my breath while he gave my crotch a grope through my jeans, gauging size, firmness, willingness. His fingers prodded my erection.

How big are you? My face reddened. I didn't know. There's a tape measure in the glove-box, he pointed.

That was the first time that it all hit me. He had a tape measure in his glove-box.

I froze. How many times had he given this spiel? How many other hitchhikers had he gotten to measure their cocks right in front of him? And then...?

Go on, he urged. No one will see us along this stretch of road. Indeed traffic was nonexistent.

Unable to refuse, I pulled open the glove box and retrieved the tape measure, a tailor's cloth one.

I fumbled with my fly and my penis sprang out. Hold the tape at the root of your cock and go all the way to the tip, he said. If you've got a curve you'll need to hold it so it's against your shaft all the way.

Five and three-quarter inches, I reported.

He laughed. You got me beat, I'm five and a half, we're both strictly average.

I looked over. His erection was sticking straight up out of the fly of his pants, directly behind the steering wheel.

He was uncircumcised, a condition exceedingly unfamiliar to me in my small town. The only guy I knew who was uncut was a French Canadian fellow, Jean Paul, who had moved south with his family to our town in sixth grade.

On a camping trip once we had all pulled our cocks out for comparison, and before he did he said, "Want to see a sick-looking dick?" and we all laughed when he flopped it out, his prick looked so saggy and loose compared to the bare, exposed cock-heads on the rest of us.

But my driver's cock was erect, the head just poking free from his foreskin. It may have been shorter than mine but it sure looked thicker. Almost menacing. But alluring in a way I could not have anticipated. I eyed it intently.

He took his eyes off the road and looked at me. Always seems a shame to waste an erection, he said, a phrase Lenny and I had employed more than once ourselves.

I swallowed. I knew where this was going.

Before I could begin to weigh my options, he spoke. I would like to invite you to my boat, I have it in a slip five minutes from the ferry. He paused. I can get you to your ferry by twelve, but there are several more this afternoon and the last one runs quite late. Your call.

He paused again. You can opt out of anything, anytime, I will honor your wishes, take you straight to the ferry if you like, but if you come with me I can promise you a highly enjoyable visit.

We looked at each other. I didn't know what to think. Part of me was screaming, "No way, get me out of here." Another part, which was attached to my erection, said something different.

You're young, he said. The door of pleasure is wide open. Keep an open mind. All kinds of good things are in store down the road for you. Experimenting is good, healthy.

While uneasy, I was intrigued and trusted him, although the position I was putting myself in was hardly risk-free. His boat, his local knowledge, his control over the situation. I had to believe him for this to continue.

Okay, I said, willing my voice to a tonal register far calmer than I felt.

He gave a thin smile and tucked his penis smoothly back into his pants. Putting mine away was a bit more difficult.

His boat wasn't huge but was comfortably furnished. Coffee? he asked when we were inside. No, don't do coffee. A beer then? He knew I was underage, twenty-one years was the drinking threshold then in Massachusetts. I had turned eighteen the summer before, wasn't eligible for legal drinking yet, not that that had stopped me.

He padded into the kitchen area, came back with a Heineken, said coffee for himself would take a few minutes, that I should make myself at home. Here, he said, opening a drawer next to where I was sitting.

A pile of porn was there, he put a Penthouse in front of me and went back to the kitchen. Playboys had been the staple for Lenny and I, all that was available in our town drugstore, but this was better, the girls had hair on their crotches and more lurid smiles on their faces, altogether more raunchy. I thumbed through the pages.

He returned in a few minutes, having discarded his clothes for slippers and a smooth fabric bathrobe. I could glimpse a hard penis through a gap in the front of his robe.

We sipped our drinks and talked. The more we talked of sex, the more aroused I became. He had a way with words, he made this complicated topic seem easy, natural.

At a lull he looked at me. Why don't you sit back a little? I'll take your beer. His blue eyes were riveted on me. I did as I was told, mute, obeying. He knelt in front of me, spreading my legs. Close your eyes, he said, and I put my head back. I felt his fingers running up and down my jeans, the barest caress to my crotch.

I was hard instantly.

After a few minutes he turned me sideways, so I could lay down on the cushions on the bench along that side of the boat. He eased my shirt off, put a pillow under my head, then removed my shoes, pulled my jeans off, then undershorts. I was almost shaking. Easy, he said. Easy. I closed my eyes.

What followed was the most complete devoted attention to my body I had ever experienced. Slow, patient, teasing.

His hands and fingers traced my body, every contour, curve and crevice. He stayed away from my crotch, which only seemed to provoke more craving for me there. These were soft hands, I might have called them loving.

Fingers stroked my shoulders, my arms, my chest, my thighs. It felt good. He was exploring.

When he did get to my crotch, it was not my penis. I felt fingertips under my balls, nudging them, barely grazing my scrotum. I felt my legs tense. I kept my eyes shut, trying to anticipate what was next and not succeeding. Slow, languorous, teasing fingertips.

My balls had pulled up in a bunch, anxious for more vigorous attention that did not come. Then a finger traced the length of my penis, balls to tip, along the central sperm-channel. I held my breath.

Fingertips briefly, too briefly, along my cock-head, then scarcely along my shaft. I pushed my hips into his hands but they retreated. It was all too slow, too light. An agony to endure.

More touches, fingers of two hands now, circling my cock-head, brushing along my shaft, tickling my scrotum, never in one place too long, never long enough. A couple times I got close, and he sensed it, backing off. I knew without looking that my prick-head was seeping fluid.

His hands would detour. To my surprise he tweaked my nipples and I almost exploded. No one, Marla or anyone, had done this to me before. Nipple play was for a girl's chest. But his touch seemed to send high-voltage signals all the way to the root of my penis. My body rolled from side to side, wanting more, wherever his hands were.

Back to my penis, my hips wanting more than anything else to push my cock into his hands, which were causing such pleasure. A lull, then a soft wet sensation at the base of my balls. He had spread my legs and was licking me.

I opened my eyes, his head buried down beneath my crotch. He was kneeling next to me, his bathrobe was open. I saw his dick bobbing with desire.

I did not find him attractive, his balding, gray, close cropped head busy down there in its work, although his tongue was doing marvelous things to my testicles. But his cock looked alluring, and it was hard. And it was hard on my account.

I closed my eyes again, wishing it was Marla down there. But the tongue was doing things that Marla had never done, going places she had never visited, producing far more pleasure than Marla had ever offered.

I surrendered at that point.

My balls were licked. Suckled. Caressed wetly, nudged about in their sack. A damp tongue went up and down my shaft, lips nibbled my cock-head, tongue-tip poked into the slit at the end of my cock. The fluid oozing out of me got spread around my penis. Everything was wet, slippery, all my nerves on edge.

And then lips over my penis. Light up-and-down suction, lingering at the ridgeline around my cock-head. Slow, deliberate, tantalizing.

My hips frantically pushed into him, the wet noose of his lips went tight around my penis, the tongue prodded me incessantly.

My sperm erupted from deep within, there was a hand around my balls, squeezing. My hips thrust forward. Six times I clenched my ass and ejected my sperm. The pressure relief was violent, exquisite. Easily the most intense climax I had ever experienced.

After things quieted I opened my eyes again. He continued to nurse at my penis, only the most gentle sucklings, and I saw him, his own eyes closed, keep his lips around my penis until I could take no more.

His glance met mine, and then he looked at the rest of me, ribs still expanding and contracting, my breath just beginning to subside. My penis lying on my belly, softening, wet, deflating.

He gave me a moment to rest, eyes still taking me in from top to bottom, then stood up next to my head. He took my hand and brought it to his penis, bobbing hard, and ran it up and down.

Ever felt one of these? he asked. Besides your own? I lied, shook my head. He laughed. I bet you have. No guy friends to wank off with? I'd be surprised, no matter how small your town was. He ran my fingers up and down his shaft.

I confessed about Lenny. He quizzed me. I managed to avoid describing the finer details of stroking Lenny, which had been far more enjoyable than I might have imagined. We would only do each other if the favor was returned, that was what we were after, the feeling of a good eruption of sperm, and willing to put hands to another cock only if our own found release itself.

If we had had a girl around we never would have touched each other. However, I had secretly enjoyed giving his penis pleasure, watching his semen come hurtling out of his cock-head.

He put my other hand under his balls, but I withdrew, suddenly nervous.

Can you come twice? he asked. I shook my head. For Marla and I, once we had each climaxed it was off to exhausted sleep. Not even with Lenny when he was provocateur. But Lenny could come twice, even three times in a row in a masturbatory marathon. I could only do one.

I thought he might be disappointed but he just nodded.

He must have turned up the heat on the boat, it was warmer than I might have expected inside.

I must get some more coffee, you good? I nodded and sat up, my penis a damp, bedraggled mess. He looked at his watch. We've missed the noon ferry, but I'll make sure you make a later one. It's off-season, the boat will be more than half empty. No worries.

I felt his eyes traveling up and down me again, taking in my thick legs, my nipples, no longer erect, my trim waist, my groin hairs all damp and matted down.

He disappeared and I was left with my thoughts. What had I just done? A strange, not especially attractive man, as old as my father, had just talked me into his yacht, coaxed me out of my clothes, played with my penis, making it erect and aroused, and then sucked me to completion. I shivered.

After some time in the kitchen, he came back in, his penis extended but not hard, just visible in the opening of his bathrobe, which he had not taken any pains to keep closed.

Come here a moment, he gestured me into another section of the boat.

I followed him while he went into a sleeping area with a clothes closet. He opened both closet doors and positioned them. A full length mirror was on the inside of each one. He had me stand so I could see myself, a slightly different perspective from each mirror, my body replicated twice.

Mirrors are wonderful, he said, they double everything. He stood behind me and I felt the fingers of one hand reach around and caress one of my pectorals.

You have an athlete's body, he noted, then proceeded to describe each part of me he thought worthy of attention, my hard chest, my flat stomach, my bunched legs. And these, he said, although you can't see them in the mirror.

Two hands kneaded my ass-cheeks, then a hand slipped up underneath my balls from behind. I tensed, but he replied reassuringly. No, not if you don't want. Let's just give this a minute.

I saw that his cock had gotten fairly hard again while he had been fondling me, not fully erect but stiff enough to stick straight forward out of his robe. The head was red, engorged.

He put one hand on my penis, which unaccountably had begun to stiffen again as well. Then shifting sideways a bit, he put my left hand on his penis, and guided it up and down.

I looked entranced at the mirrors, two hands on two cocks, from different viewpoints, neither hand stroking its owner's penis but another's.

As a variation at home I had enjoyed masturbating in front of a mirror when I could arrange a good setup. For some reason seeing your own body -- penis, balls, erection -- from a different angle made it more arousing, as if you were a voyeur to your own self-pleasuring.

We slowly stroked each other's cocks. I was delighted in the feel of a stiffening penis in my hand and being fondled myself by another hand.

He quietly gave me instructions, how to put pressure right underneath his cock-head as the foreskin slid over it, to tighten my finger circle to make a noose, to make sure to reach underneath to cradle his balls and caress them. I became aware of how little experience I had when attending to a penis, even my own.

His own stroking of me was divine. Soft, then firm, slow then fast, gauging my reactions and sensitivity and reacting to them. It grew. Got half-hard again. His eyes were fixed on my dick, both in direct view and via the mirrors. He tweaked a nipple and once again I felt the jolt of electricity go to my cock.

His foreskin, a foreign item, slid up and down his shaft. It suddenly struck me that masturbating an uncircumcised cock was somehow quite different, the thought had never occurred to me.

I was enchanted by how his cock-head would emerge from his foreskin, then disappear again as my hand pulled the skin back up. After maybe ten minutes of slow, careful stroking, the mirrors revealed two hard penises, capable of pointing upwards, towards the ceiling.

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