A 101 on Masculine Pleasure

But the salt of cockshaft was a precious part of the process. And I needed someone else to bring me that.

So lesson learned. Whatever it categorised me as, I was someone who really, really enjoyed the taste of cock and cum, and the act of earning it.

I was right. The address was literally across the street from the mall I spent my childhood in. That made things feel pretty real. But the door wasn't quite right: the lobby's street-facing wall was thick glass, with peel-off cellophane on either side of it and some stick-on posters about how I wasn't supposed to go in. Inside a doorframe of what I'm guessing was going to be replaced by giant automatic doors was some raw wood framing and a piece of drywall inside that. Cut out of the drywall was a smaller doorframe, with an ordinary bathroom-style door. It wasn't locked.

And now, a year later, as nervous as it made me (I was grown up, but he was, on a whole different level, a Grown Man), I couldn't wait to learn what it was like when an experienced lover had sex with you. This intriguing older man with the fun attitude and gorgeous middle-aged cock would get the most grateful, eager blowjob of his life.

Next morning came. I was glad not to have been asked where I was going. It felt way too real and way too close, taking a single brief bus to the very nearby block where I was asked to come for this strange arousing man. Stepping from one world into a very different one, the boundaries too close.

I very casually defied the stick-on posters and walked as casually as I possibly could inside. It didn't at all look like the kind of place a person in his second decade in street clothes was supposed to go, but I had a theory, a risky theory, that most people wouldn't bother someone that walked like they were both supposed to be there and bored to be there and in just enough of a hurry.

I was a strange mixture of bold and nervous that whole day and especially as I crossed through the door and tried to appear (to no one, maybe, maybe to people on the sidewalk, who may or may not even care) that I already knew where to go after that and how to.

I did as I was asked, I found/took the nice elevator up one floor, and stepped out onto a sunny area. I could hardly even tell what it was supposed to be, the drywall was barely painted, there was still raw wood and green tape. There was little furniture yet, just one not-impressive desk, and the whole place still smelled like lumber.

I saw him. In a button-up shirt with hastily rolled sleeves and a tie. He stood up from his desk, and I saw happiness and anticipation. He saw me. Pre-20 youth, who, right in front of him, was realising in realtime it was okay to ignore the instinct to cover up tenting pants. My jogging pants made me obvious, and it was strange not doing anything to hide, but I think my body realised what was happening when I just looked ahead at him, and let my visible arousal be a fact between us. An erection in a strange building was different than erection at a computer chair.

"Hi. Thanks for coming? You still feel good about this?"

"Yep! Well....... I guess that's already obvious?" (I seem to have almost exclusively pants that make erections more instead of less visible.)

He smiled. "Are you ready to make it more obvious? You don't have to hurry, but you don't have to wait if you don't want to wait..."

I can't overstate the nervous, rickety excitement for me. Yes, I had repeated oral sex with a peer once, a kind of self-discovery, and I had now shown my naked body masturbating to men who masturbated back to my screen, but this was somehow qualitatively very different from either of those experiences.

I remembered the instinct to just take the plunge. First it was to lick a friend's penis. Now it was to become naked for a middle-aged man in a tie. I assumed being naked was the next step. It was clear he probably wouldn't mind. It seemed like the thing to do. A thing that would make him happy, a thing that would make lots of more things possible.

And this was not the dark of night, like my experiments with a friend. I was bathing in sunlight from a glass wall overlooking storefronts and sidewalks. I was golden-yellow with it.

As a grown-ass man stood in the room with me, I let him watch me take off my backpack, my jacket, my shirt, my shoes, my pants, my socks... and more tentatively, with shorter breaths, my underwear.

I let a grown man look at my penis while it was hard. I watched a man in the room with me stare at my nakedness. He smiled, and herded me gently by the shoulder closer to where his desk is. I was naked and being brought somewhere by a suited man. That in and of itself felt kinky, breaking so many rules of what's within the bounds.

And then I watched this man with me take off his clothes. I saw his mildly fuzzy torso, his pleasant bits of tummy fat, the occasional grey hair among it all, and an erect penis suddenly bobbing about in melee range of me.

Besides the novelty of all of that, let me punctuate this point again: the penis in front of me was gorgeous, in a way that was even more obvious in person. Tight skin wrapped around a large and curvy head, curving slightly to his left, into a perfect tuft of foreskin. It wasn't a mushroom of largeness, it was just that the sheer width of the shaft gradually expanded higher up. A lovely curving expansion of meat. The elasticity of the cock's skin held up a very full ballsack. I could see pumping blood in fuchsia lightning-bolt shapes along the shaft. The hair mane looked positively downy.

There was a dawning sensation already that if I was about to actually worship that penis with my mouth, it would not just be an act of service, I would completely and faithfully mean every act of that worship. My enjoyment of this act would be as obvious as my swaying and flexing erection.

I could feel my nervousness being replaced with something. Something that filled my mouth with drool, that made my penis pulse and flex. My weakening legs were asking me to stop standing, to maybe kneel, now.

And yet, I felt new, and green, and scriptless.

I could tell Dave didn't though. He smiled at me, apparently delighted.

And when I saw his calm smile at my naked self, I found the courage to seek out his penis blindly, watching his face while my hands found him. My hands beheld him, my right hand on his large and lovely shaft, my left hand on his silky tightened ballsack.

I was young and overwhelmed with novelty, and so I stayed in that first moment for a while, holding an entire man's penis. It had its own pulse. It pulsed heartbeat at me, and it pulsed a slow natural hump into my hand.

I watched him enjoy my first explorations and I adored the feel of him. I watched him see my enjoyment, and he could have no doubt that he was truly with someone thankful for access to his penis and everything it offered.

And he touched me back. Using each other for balance, he held my shaft and massaged it. He wasn't so much exploring it as new ground like I was, he was calmly taking the helm of my pleasure. I was already ready to give him that control. My nervousness wasn't reluctance, it was anticipation, it was giddy bashfulness that this man had brought me here to do things with me.

He backed away and I saw him again. His aroused penis was somehow even a little bigger. I knew I soon needed to taste him, to learn how to draw pleasure from him with my mouth. It's what I'd wanted for all this time, more than another orgasm in someone else's control, I needed to make someone else's orgasm happen, and then to capture it and cherish it in my mouth.

He saw and clearly relished my flushed desire and I waited for his preference.

And then...

He grabbed his own penis. With his large powerful hands he wrapped his palm and fingers in shaft.

And started beating his shaft.

Granted, his testicles looked beautiful when they shook. I was just confused. He had an eager blowjob-giver. He had invited a nice mouth to love his cock. Why was he masturbating? He was wasting seconds of crescendo on himself!

After a few beats, he looked back up at my face. "Something wrong? Second thoughts? It's okay if you're having second thoughts."

"Um, no! No I'm not. I'm just excited to do actually get to do this!"

He grinned widely and then rapidly beat himself off in my direction.

The best thing about having sex instead of masturbating is that you get to play with another penis. I wanted this even more than I wanted new heights of pleasure for my own.

So the man in the tie smiled, excited grateful and hopeful, when I politely knelt and politely waited.

Once he found visual confirmation that he was still with an eager play-mate, he approached me. I fawned at the erection, looked gratefully up at his face, and then just returned to the beautiful foreskin and the floppy ballsack.

I felt palms on my ears and I opened my mouth.

I tasted salt and smokiness as I filled up. My mouth flooded with drool and I heard a groan.

The fucking lovely sensation of the man's filling shaft in my mouth.

Once he had found the curve of my mouth, with as gentle a hump as he could bear he cascaded in and out of me. I felt soft skin striking under my chin.

The sheer kinky truths of my situation were sending me through my arousal, the novelty of kneeling in this office and welcoming this penis into me, were the loveliest possible thoughts I could fixate on in this moment.

How was I lucky enough for this penis to want me. How was I lucky enough for this secret chance to touch it.

So I gulped and I sighed and I enjoyed long minutes of this shaft entering and exiting my face.

And then Dave took his cock out and again masturbated in front of my face. He didn't look near cumming, he was just pounding away at himself. I watched him get more and more excited, his shaft tightly held by his hand, and, as he groaned, he let go of himself and hurried his penis deep into my mouth again. I did everything I could to take it as deeply as he clearly wanted.

I watched the man in the tie feel pleasure high above me, and his humps were now slight, not willing to exit me anymore and clearly so, so close to something. He tried to watch my young face open for his penis, clearly enjoying the details of the scenario as much as I did.

Eventually I had to slip off of him and seek new gulps of air. He seemed to like watching me heave on my knees.

A moment later I asked,

"I'm just curious. Why touch yourself? That's why I'm here, so we don't have to jack off!"

"Just getting myself ready... Ya can't cum with just a blowjob, only a fierce hand works. You don't learn that in porn."

"But the first touches are my favourite part."

"Really? I thought everyone's favourite part was cumming, how can it even be anything else?"

"Well the first touch makes the last touch feel better."

"I don't understand?"

"Oh. Well, if you race to the hard beat-off, then the whole thing doesn't feel as good."

"It's the only thing that works."

"Um, I wonder if that's because you've made yourself insensitive?"

"Well, do you want a blow? I still have time."

"Um, I'm not sure. I'm just trying to figure something out."

I saw his face and realised I was sounding like I was complaining, I was at risk of losing this chance. Maybe I should have just gone for it. Maybe I was stupid. But I needed to repair something anyways.

I came closer to him. I think we both were very aware that I was still naked. Which was still very new to me.

"Do you still like the idea of doing this?"

"Fuck yeah. Absolutely. I want this, a lot. Do you still want this?"

I nodded and smiled.

He just stood, trying to look as casual as possible, not anxious about me, not anxious about what he wanted, and not anxious about whether he was coming off manly. I knew the type well. I wouldn't go near him if I thought he was fundamentally gross in burly machismo, but I knew what he was told to be. What a wasted life and what a wasted penis.

I saw him, for a moment, as suffering from arrested development: like there's a period of growth that he and almost every other man for at least two generations has been commanded to skip.

Masculinity is hot. But has being macho changed definition until it was unmanly for sex to feel great?

What the fuck had we all done.

And what now. With this poor, wasted perfect penis and this horny delight of a middle-aged man. He still watched me, fixated strongly on my young nude self, still pulsing my pelvis in desire and still nice and stiff for him.

And then I had a moment inside myself that harkened back to the beginnings of The Grinch's scheming. I had just had a diabolical, cunning, completely consensual and yet scheming idea. And I had about one more second to say the next thing or it would never have a chance of happening.

I tried being a bit sexy. I sat on his desk (again, very naked), and he watched the boldness of it. I put one knee up, like I had on cam, and he was able to see multiple angles of my body, and my erection centred around the whole pose as I talked to him. My shaft arched with excitement.

"I remember you sending me that first message. And I remember you on the bus. The way you excited me about coming here. Do you like the idea of a younger guy learning about sex from you?"

He shrugged and nodded. He looked a little more interested than his shrug implied.

"That works out. I like the idea of an older man teaching me about sex, and having sex with me. You're an older man with what I think is the perfect body, and I want us to have sex. We want the same thing, and I think we both want it really badly. Look at me, I'm squirming right now. A young naked man is squirming because he wants to have sex with you, Dave."

I smiled and he just stared.

"So I want to make sure you know all about the position you're in. You've met a young, cute, eager, deeply horny penis-worshipping cum-eater. You've already met in person and it's not awkward anymore. He thinks you have the best cock he's ever seen and he's very interested in regularly trading blowjobs with you, for as long as you want. His cock is also great. This is better than a Craigslist encounter, this is a dedicated fuck buddy who wants to become an expert in your cock in particular, all under the table in an arrangement of secret and frequent sex."

I have no idea how I got all that out of me so eloquently. I certainly shuddered my voice through a bit of it, I hope the right amount that I sounded excited rather than nervous. But I could tell he was excited too. His face was serious, flustered, and his penis danced a little for me, flexing in request. Something on his foreskin shone.

"I'm not saying this to take advantage or tease you. We both have a lot to lose from this secret. We're just two men that get to have sex whenever we both want. So, if you're interested in having sex with this young naked guy in front of you, great, we'll meet in two days in the morning. I'm not being a tease here, I just know what will work and what won't. You just wrestled your penis into insensitivity. I think it can feel way, way better than you realise, but I want the best conditions, so what if we waited until then."

I hoped I had played this right, and that I hadn't ruined things with this man. We were still very, very horny for each other. I checked again later that night, and, once he was no longer freshly spent, he was again eager.

I knew that this man, more experienced and equally horny and comfortable with mentoring, would have many lovely things to teach me about how to give and receive sex, and once this boundary and lesson was out of the way, I was very-much looking forward to giving the helm back to the man with the tie and the perfect penis.

A new day. I was somehow even more nervous coming this time.

I stepped out of the elevator, sniffed in the pleasant smell of lumber, found Dave rushing through one last thing, and decided to keep up my boldness momentum. I found a nice rectangle of warm sunshine from a high window, and in that rectangle, with as casual a smile as I could, I let him watch me pull off my jacket, shirt, watch, belt, jeans, socks, and underwear. I let him watch my erection as I sat on his shabby desk.

"Okay! Your horny teenager friend is naked again. You've needed to cum for quite a while, and it's been rough to wait. Would you like me to start doing things now?"

"Fuck yes, absolutely."

"Okay. Can you be patient with me? I'm going to be a bit new at this, and I need you not to rush me."

"Sure, yeah okay..." He sounded casual except for a little shudder in his voice.

"Holy shit. Okay, hang on, I think I have to go to the bathroom."

Something struck me. Something familiar.

"Hang on. Wait. Why do you think you have to go to the bathroom?"

"What?"

"Trust me for a sec. Let me see you."

He looked weirded out. But he shrugged his shoulders, and took off his shoes, and unbuckled his belt. His pants were complicated, there was a clip, a zipper, and another clip inside before they were open, but pretty soon he slipped everything down.

And I smiled.

He started a little "Aw shit" but then looked at himself confused. The bits of liquid on his tip didn't surprise him at first, but he looked at himself like something wasn't right. The liquid wasn't single drops, it was a teeny bit of goo, shiny and clear. It even webbed for a second on his underwear.

Please believe me when I say I was still nervous. I was still a very young man naked in an open office concept with an older dude.

I watched his body. His penis looked a tiny bit bigger today, his erection a slightly fuller shape, his pretty foreskin opening up just a little. He really had been politely neglecting his sex drive since we last met. And he watched me. His penis flexed as he watched me, and I tried to pose like I had before: arched up using the corner of the desk as an awkward seat, one knee in the air and one leg flopped down. I was full-on parading for him, as casually as I could. I watched him enjoy me for a moment, desire me for a moment, while he waited for who-knows-what.

I remembered our interplay, and I remembered what worked nicely. He was both excited and taken aback by frank boldness.

He looked down at his penis now, which was now even wetter.

"You really have no idea what that is, do you?"

"...Oh. You think I came? Like in a wet dream?"

I smiled. "Nope. I thought so too the first time I saw myself do that... but I looked it up. It's not cum, and it's not pee. It's something else."

Dave looked at me in a kind of horrified apprehension. "Uhh what?"

I slipped off his desktop, tried to smile for him, and I knelt in front of him. He seemed to like that.

"So I'm not speaking from a lot of experience, but doesn't it sound right that we produce our own lube? This is lube. It's lube that cocks produce so sex can feel better." Dave didn't look like he believed me. "It has no sperm in it. It's slippery, warm, tastes different than cum, acts different than cum, and you'll make as much as you need.

I ignored a knot in my stomach and grinned for him as I came close to his erection.

"Oh... and it's fucking delicious."

Right after I said this I let my tongue out without flexing it and I slowly cat-lapped up the liquid from Dave's foreskin, with the least pressure I could manage. I was smelling and tasting the thid penis of my life. It was different and it was lovely already.

I'm guessing Dave had never before made the gaspy sounds he had just made just then.

Smarminess be damned though, there was something I'd noticed during that last little smooch. I needed him to answer. His revelation was poorly timed to my first moment of hurry. He was calmly analysing his own heights of sensation. I breathed and waited. Finally, finally, he said, "Okay man, yes, fuck yes", and I had to slow myself down and resume more slowly.