A 101 on Masculine Pleasure

I don't know what it is about letting someone watch me cum. It's vulnerable, it's horny, it's kinky, it's forbidden, and it's friendly.

I don't know whether the tiny pieces of experience I had had earlier in my teenagehood (though not during highschool, that would be insane to me) had left me needy or whether this was my baseline at the very end of my teenagehood, but my needs were making me more adventurous lately. At least they were virtual. Strange faceless cocks, typed compliments, encouragements, orgasms dedicated to me.

Recently I had started using a group space. Occasionally, I took the risky move of accepting an impressed and impressive user's offer into a breakout room, and type and masturbate alone. This was new for me, and I wasn't sure how healthy, but I enjoyed being enjoyed by people I enjoyed just as much.

I like bodies to be a bit older. I need them not to be muscular, just soft bodies.

And I've gained a soft spot for a great penis.

So when I logged on, someone had sent me pictures. The message he sent with them was, "I read your profile, and oh god that sounds amazing, you have such a hot mind. That video made me cum, so here's one for tomorrow." Even without seeing a live image I was flabbergasted.

I won't mince words. The pictures he sent stunned me. That penis had all the things that loved to be touched: large, soft, slightly floppy balls, a long shaft pumping with external veins, and lots of unstretched excess foreskin, gathered around the whole head and some extra gently bunched up overtop. This thing wasn't just gorgeous, but a gift to himself as well: it had all its erogenous zones in excess, and his orgasms must just stun him.

I looked at his profile and his age and his body and his oral fixation and his interest in helping the inexperienced and his horny eagerness all checked my marks.

Why keep that to myself? So I typed:

"Oh my god it's perfect. No. That's actually, literally, the best penis I've ever seen. I love it. And I like your profile too.

A reply very soon came, "Holy shit let's cam."

Before I could even finish typing a reply he request came in, and I glanced around to confirm no one was around. I Accepted.

Both of us, maybe in our excitement, forgot to hide our faces in that first instant, but as he moved himself and his camera, soon I saw a half-buttoned shirt and then I saw the nakedness below it.

I smiled at the cock he showed me, even lovelier live, full and pretty, and so I stood and backed up and presented myself openly to him, letting him see the entire part of my body I was about to relish with pleasure.

He grabbed himself and I watched his ballsack dance. I grabbed myself and I wasted a lot of seconds with my eyes closed, knowing I was being watched and just reveling in that fact.

So I returned to reality and watched him. His masturbations made his ballsack dance, chaotically. I never knew which way those beautiful balls would flick next. His shaft reached so high. And there was something about a perfect button-up shirt and an erection emerging from under it, and there was something about how high it towered up that shirt.

I heard him groan even in those seconds he wasn't pumping. I think he just enjoyed my existence. As I hiked one foot up for some reason, putting myself both at a high and low angle and opening wide for him, I could tell he could see both my eyes and my balls and I was for the moment too feverish to mind.

I'm embarrassed to say, but the excitement of the owner of that cock enjoying me, and the search for an hour for the perfect reason to cum, got me to orgasm in very, very few minutes.

He saw me quickening my movements, and he moaned and quickened his movements, and our arousal escalated each other into happier moans. For once I decided not to resist how much I needed to cum and just let it happen. I knew this man wanted to see it. I wasn't in the mood to disappoint a half-naked admirer.

I had cum, quite a lot, and it had fallen down my hand and off to the floor, and he enjoyed watching that.

Something about the excitement made me adventurous for just one more instant. He clearly needed one more moment of inspiration. And it hit me.

I let him see my face again. And while he pumped his long shaft and swiveled his ass in something brewing, I let him watch me lap my tongue along my knuckles, gathering any cum I could reach into me. He stumbled back again and I saw his whole self too. With a surprised and dumbfounded guffaw he entered a cum face and I watched cum leap up and around. We watched each other finish ourselves off. And, as usual, we made little gestures and hotkeyed the window closed.

Next day.

So this isn't completely impossible and unbelievable, because it's not a huge city that I live in. But holy crap, world. Really?

I admit it was risky enough to become naked for a man on a site that filters by city. But I liked to believe that one day I'd be brave enough to do something about it, more than what was essentially interactive porn and unconsummated possibility.

So, as weird as it was, we noticed each other at exactly the same time. It had to be the same time or the other would have looked away by instinct. But there, on a bus, really near to each other, the back-and-forth seats in groups of four meant that a quarter of the way up this bus, I saw him.

We had seen each other's faces yesterday. We had seen each other's cumming faces. And now, the surprise at the unlikelihood stopped us from looking away long enough to get us past the initial fear response.

We were now in the second, far more cerebral fear response. The possibilities of ruined secrets, the hazards, the social situation. In real life, the age gap was a more real fact between us: not just an exciting arouser, but a social norm.

He was trying to look away a bit. I was trying to look away a bit too. We kept returning glances. Eventually, it was just silly. We were just not strangers anymore.

The bus had crossed a boundary and entered a less populated city. So the bus was less populated anyways.

I would never tell him this, but I was just barely aware of the fact that my stop was back there, and just consciously enough aware that I wasn't on a schedule that I would be missed about.

The man casually stood up for a minute.

A block later the man casually sat down.

In my four-section of seats.

"I can't tell whether this sucks or whether this doesn't suck," I eventually said, a little smarmily, a little shyly.

The man gave a single breath of chuckle.

"Know what you mean."

"It is you, right?"

I had déjà vu. Not only did the question bring up the memory of yesterday, but then of something else.

That was it. The moment of deciding not to hide. grin

I asked that question, and then we both looked downward.

And there was clarity.

I excite this older man.

He still excites me.

Without standing this time, he switched seats beside me. We looked around conspiratorially. There was one passenger on the train, and the make-up of the seating arrangements had some very interesting line-of-sight flaws.

The older man said something to me, not very loudly. "Okay............... I have a crazy idea."

Those words alone made me dizzy. This was very, very, very, very real. Unless I was very much mistaken, a man twice my age was about to negotiate sex with me. The feeling in my stomach was almost definitely desire, it just felt very queasy to be this close to crossing the line.

After a moment he continued, and I'm sure he saw how blushed my cheeks were.

"I work at this place that's still under construction. And the construction is delayed. I'm literally the only person in my part of the building."

"Oh! And you want to.... cam there? ......Wait."

"Heh." We interchanged between looks at faces and at crotches.

"You're really serious?"

"What do you think."

I looked around again. The bus was going up a hill and some sort of turbo engine was making it conveniently loud around here.

"I think it's really unfair that you saw me finish so quickly. I usually last."

He smiled at that answer.

"Do you want to come over?"

I didn't answer at first, but I'm sure my rosy cheeks, dilated pupils, and dry-lipped heavy-breathing mouth were unambiguous with interest.

"We don't have to."

"Oh god, I actually think I might want to. I think I might actually be doing this? Am I doing this?"

"You're in control of your choices. If you come by, we're all alone with no one telling us not to. No one but ourselves."

"Why an office?"

"I'm separated, still living together. No problems with going afield, dating or sex. What's your situation?"

"Um, about to move into a shared apartment? No privacy now, no privacy then. Yesterday was a lucky chance."

"Mhm. It's hard, stealing moments to be by yourself. I know it. Doesn't have to be this way."

"So an office?"

"Heh. Seriously. I'm only there to hold down the fort while we wait for construction to resume. Fucker in charge doesn't even want to hire a watchman."

"Wow."

We went up another slight incline, and the impatient driver again made the engine loud.

The man said, "Let me ask you something................ did you lick your hand for my sake?"

I blushed a lot more, then smiled a little.

"No. I like it."

Then he heaved a breath out, he looked a little dizzy in his reaction. "Jesus Christ," he said, and, with him in a surge of horny appreciation and me having a crazed post-pubescent moment again, at the same time we both let our hands fondle all over each other's shafts, probably a little less subtly than we should have on the bus. I felt the unlikely length and fierce solidity and warmth of a penis through tailored pants. For the first time I noticed he was wearing a tie. His hand was large, and had a gently commanding presence on my shaft as he slowly rubbed up and down.

Just like yesterday, my desire for him had skipped entire steps in my pleasure, and our needy grasping at each other made us squirm for each other. We exchanged needy glances.

I glanced nervously back and forth throughout the bus. No one had noticed. I wanted more. I wanted more so desperately much. He obviously did too.

"I'm Dave," he said quietly, becoming subtle again but giving my shaft one last loving little caress.

"I'll come. I'll come to this place. Are you sure it's safe?"

"Oh yeah. I'm bored out of my mind there, every day. Fuck, how's tomorrow?"

I stared at the cylinder in his pants.

"Early tomorrow?" I said, more boldly than I had ever said anything.

So how did I as a young man know so much about pleasure?

Flashback time. I had had one girlfriend, and we had kissed A LOT, but we were too shy to do anything more than that. Which was probably for the best.

I also said I had had one sexual experience with a guy. I guess, although there was no emotional attachment, it was technically an affair.

For someone with little experience I have a very specific idea of how to treat a penis.

I learned a lot about how to feel nice at camp. The kind of camp where you're not your family's problem for a week. Grade 12 immersion into wilderness learning. Everyone was 18 years old, technically grown-up but still a bit dumb about life. Surrounded by others whose bodies were being transformed into different shapes by the same chemical that told you to respond with aggression, and also the same chemical that punctuated arousal into moments of delirious frenzy.

Two thirds of the boys around us would be straight and told that manliness was impressive feats of douchiness. A third were interested in their fellow boy, half without realizing it, and were currently secretly crawling out of their skin with desire, their heteronormative chaperones none the wiser that splitting teenagers by sex was overlooking two important facts: one, that some teens are gay or bi, and two, that some teens are so overwhelmingly interested in trying sex that camaraderie is an idea some of us will inevitably conceive of.

Some of us use our in-group instincts to include or exclude. Some of us use our instincts to feel who's safest to stay away from and who to stick with.

I had good instincts about exactly one friend. He just had nothing to prove, and didn't mind telling me about the things he was a geek about. So I let myself get a bit geeky, and otherwise we were just boys together, but without proving machismo all the damn time.

I could go on and on about a relatively good short-term friendship. But I'm sure that what you want to hear is that, one afternoon while the camp was taking a break and we had no interest in the stupid jokes the other guys were saying, we just wandered for a bit, talking about TV shows. What you want to hear is that when he sneezed and caught it in his elbow, his jogging pants bobbed about and flopped back and forth a serious erection, in the kind of jogging pants that are just terrible for hiding them.

There was no time to be cool about it, he noticed me noticing at the same time I noticed. He even sneezed a second time, robbing him of a crucial second to somehow hide it before it was really obvious. There was nothing to say, and while I was having this "It happens to others too" guy moment, he was apparently having a "My life is over" moment. I had to do something, I could tell I was about to lose the only person to talk to without going insane.

"I'm sorry, okay? I know it's weird to have a hard-on out here, it's not what we were talking about, it's just getting like that all the time, okay? That's probably weird, I'm weird."

I suddenly thought of all the recent hardons I had had and now I wondered if anyone noticed them and was nice about them. I realised this was another moment where I had one second to respond before most avenues through the talk would disappear.

What answer what answer what answer

"Me too!"

The way I rushed it out of me must have sounded like enthusiasm. I tried to calm down and repeat.

"Man, me too, all the time. I don't know whether it's just how men are when they're finished growing up, whether it's just like this forever, but maybe it is, and maybe it's normal?"

He tried to chuckle as though he didn't still perceive the moment as a catastrophe. But I was obviously rescuing him from the awkward moment, and I think he was grateful. Which meant we had to talk about it together, to make it feel normal before we could move on.

"There is no way people fuck this much," he said conspiratorially. "But why does this happen this often then? I must just be weird."

"We must be weird", I corrected and that let him smile. "Or maybe it doesn't come back for longer when you do more than.... Y'know..."

We were both dashing our faces back and forth, scanning the landscape. This was a weird thing for people to know you were talking about.

"I don't know how much longer we're meant to wait, man," he said.

We sat on a big rock where a sliver of space between tree branches showed miles of mountain and sea.

This was a big thought. And we looked out at the seaside in our view while we seriously thought about that.

And back at each other.

We both noticed each other's erections at the same time, and then we both saw each other hiding ourselves, and we looked at each other, laughed nervously together.

And then? And then we just sort of... gave up.

We reluctantly stopped hiding the very revealing shapes we made in our pants, his jogging pants a wide tent and my track pants a form-fitting cylinder.

And then I noticed that this moment, this giving-up, sort of gave us permission to not look away. We hadn't looked away for a bit now. For the first time in my life, I let my erection be looked at.

"Me too," I simply said again. "All the time, and it's... strong, like it needs a lot of... things."

"Yeah. And this week.... Like... we have this..."

"One giant room of cots close to each other?"

"Yes! I have no time alone except in the toilet, which... isn't great."

"Not a great toilet."

We laughed.

And he paused for a moment, then noticed our erections again, and that let him keep going." But it's like, really really dark out here at night, and when it's late, it's like..."

"There's no sense of sight! Right! It's spooky, like your eyes just aren't for anything, I can't tell whether they're open. So I think about, maybe..."

"Yeah, but there's noise, and there's-"

"-Mess! And there's-"

"-Too much at stake."

We laughed and nodded.

And looked at each other's pants.

"Sorry I keep looking."

"Well so am I."

"Why do we keep doing that?"

"Dunno?"

"Do you think we're gay? Is it weird that I haven't thought about it?"

We must be pretty cool people, for that question not to be dangerous. He definitely wasn't saying that to get something out of me, he was just genuinely curious what it meant.

"Yeah, I... know what you mean. I like girls, but... when I'm like this? I'm not sure exactly what I want to happen. I think it could be a few things that are okay."

"Yeah, same. I just don't know what I'm supposed to do about this, even if I could have whatever I want. Is that weird?"

I started counting. 40 minutes until we were due. 20 minutes of walking in a completely different direction than the others were hanging out. Which would put us in trouble in about 45 minutes.

"How should we find out?"

He had gotten a bit closer to me by the time I asked. If I didn't know better I'd speculate that his body was asking for me.

It was a really open-ended question, I didn't want to scare him about what I was starting to think about, but when I said it we both looked at each other's erections. And at each other. And at each other's erections. His hopped at me a bit.

We were breathing pretty heavily.

"Oh god could we actually? Like is this crazy?" he said to me.

"It's crazy. And I think I'm going to do it."

He heaved at me.

And then he obviously performed the distance-counting and minute-counting I had just done. And looked back at me, and nodded nervously. And breathed heavily.

"What should we do?"

"I have no fucking idea."

"Okay, should we stop, or should we go, or....??"

I noticed a big boulder nearby. And when I walked to it he walked too. I walked to the far end, facing the water and away from everything else. We were now even more hidden, and seeing over a bit of a cliff.

We looked around and around, and confirmed it was impossible to see us unless you got close enough to make a lot of noise first. We didn't exactly communicate what we were preparing for, we didn't even know.

We stared at each other and grabbed our pockets and hesitated and watched each other give each other brave nods, and then we slowly and then rapidly pulled our pants and underwear down, quicker once we realised the other was really going to do it.

We each looked at naked erections in front of us for the first time. His had his pink head emerging a little from between the opening (mine hid completely behind what I now understand is foreskin), peeking out a little every few seconds, maybe as some sort of repeated flex. Both bounced with flex and we even humped a tiny bit as reflexes. And both of us were wet at the tip for some reason we didn't understand. I had never seen that, and now it was happening to us both.

We pointed ourselves at the ocean. It felt weird not to be alone, we were bashful to say the least, but there was no possible way to convince our post-pubescent bodies not to masturbate for one more minute.

Something felt better about my touch than it had before. Looking back, there are probably three different reasons it felt better.

At the start we closed our eyes, and heard each other's muffled movements.

Then we watched the ocean.

Then as we started making noises, we noticed we watched each other. We watched each other's hands give ourselves pleasure. We watched our techniques. We adapted. Pick up each other's wordless tips, maybe. (No pun intended. Pointers? No that's worse.)