Meeting Greg Pt. 02

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Continuation of my afternoon with older man Greg.
2.7k words
4.72
4.8k
10

Part 2 of the 2 part series

Updated 12/30/2023
Created 08/02/2023
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It was warmer outside than it was previously. Greg walked over to the bar area to fix himself a drink, asking me if I wanted anything. "Sure" I replied, still a little dry mouthed and in need of something to clear it up. I was still buzzing from the orgasm downstairs, and still half-hard and horny for the entire afternoon. Greg looked amazing at the bar, carefully studying his bottles while he mixed himself a drink. He returned again with two glasses and offered me the same chair I'd been in before; I felt a little awkward sitting on his cushion with my bare ass, but he assured me that's what he preferred and directed me to sit down. He let out a deep long breath and raised his arms in the area like a conquering hero.

"Whaaaaaat a beautiful afternoon, huh, Michael?" he declared, leaning back in his chair. I took a sip from my drink and was sad to learn, again, it was just a plain club soda with a lime. It was refreshing though, and before i realized it, I finished the glass completely. Returning from his praise of the afternoon's weather, Greg realized I'd downed my glass and mentioned there was still half a can open on the bar if I wanted to refill the glass myself. "Besides," he added, "this way I can look at your cute butt as you walk by."

So I made a leisurely show of walking past him. For his part, he leaned forward and playfully smacked my ass before watching me walk away towards the bar. "Yep, that's a nice ass, Michael" I heard him say as I rounded the bar and looked for the can of club soda. "I have some beer in the fridge if you want something a little stronger, I guess you can pour yourself a drink, but be careful. I don't want to get a charge for contributing to the delinquency of a minor" he laughed to himself.

"Oh no?" I replied playfully. "What would you call all this, then?" I asked, kind of turning my hips back and forth behind the bar.

"Well you're 18, right." He paused. "RIGHT?"

"Yeah"

"Ok. So what we did downstairs was perfectly legal in the eyes of the court. But technically you have to be 21 to drink unless offered to you by your parents in your own domicile blah blah blah, none of these things would apply to us"

"Well if I get too drunk," I said, returning to the patio chair with a Corona in one hand and a refilled club soda in the hand, "I'll just have to stay here the night." But before I could turn into my seat, Greg reached for and grabbed my half-hard cock and gave it a tight squeeze.

"Who said you could spend the night?" he asked, then let go, allowing me to continue my pathway into the chair.

"Awww" I pouted a little bit, and brought my knees up into my chest. I saw his eyes drift down to my exposed butthole so I wiggled back and forth in my seat a little bit just to tease him. "I don't know," I continued, bringing my feet back down to the ground, "I'm sure I can tempt you with something" and opened my legs for him, stroking my erect cock a couple times with my hands.

"Ohhh, you're going to get yourself in trouble, young man" he said, before taking another sip from his drink. "But I like that about you, lots of fun we can get into." And I smiled, and he looked off into the distance and we settled into a little comfortable silence as he finished his drink and took alternative drinks from mine. As he rose to fix himself another drink, I noticed the large protrusion from his shorts and realized that, not only didn't he come earlier unlike me, but he was rock hard under his pants. He asked me if I wanted anything, I declined, then started walking back over. As he got close, I reached out and grabbed his erection through his pants and gave it a little up and down stroke.

"Are you thinking about all the trouble we can get into?" I asked, continuing my somewhat awkward hand motion.

"Indeed I am, Michael. You're a very beautiful boy, and I've very much enjoyed getting to know you. And I'm excited to see how much more I can learn about you, too." And he sat back into his seat, setting his drink down on the table. "We'll just take things as they come, I'm not sure you're ready for that just yet."

"What does that mean?" I asked, a little hurt by his comment. It felt almost like a rejection, or at least a bit of him thinking I was a kid when I no longer felt that way, not after what happened downstairs.

"Earlier today you were unsure if you had the courage to even meet me for coffee, and now you're talking about...I don't know what you're thinking in that head of yours. I'm having a lot of fun with you today, I enjoyed going down on you downstairs. I love this, getting to stare at your cute naked body while we sit out here. Let's not bite off more than we can chew"

"What does that mean?" I was starting to feel a little self-conscious and confused about where this was going.

"I like this dynamic: you here, naked and vulnerable while I can casually enjoy your nakedness. I like your role playing like this."

"What do you mean about 'not biting off more than I can chew?"

He became very firm and direct. "It means, Michael, that I have a very large cock. And while I would love nothing more than for you to fish it out and get me off, I don't think you're ready for it quite yet."

Silence. That was a fair response, and I didn't really know how to respond to it. He was right: I didn't have any experience with another man, let alone someone as experienced and confident as Greg is. I looked at him relaxed in his patio chair, drink in hand, and I thought he was so sexy. I stood up and quickly closed the space between us, leaned in and brought my lips to his, kissing him for the first time. He returned it passionately, and brought his hand up to my face to hold me in tight as he intensified his kiss. I was completely sucked in by his passion and lust. He moved his hand down and tweaked my nipple hard before moving down and jacking my erect cock a few times. I pulled out of the kiss and stood up, then leaned in and whispered,

"I want to see you how you see me. I want you to show me your big cock" and I reached my right hand inside his shirt and worked my way until I found his nipple which I squeezed as hard as I thought he squeezed mine. He didn't even flinch or adjust his eye contact. He smiled and said, "ok" and as I leaned back and retreated back to my chair, it was my turn to look on lustily as Greg stood up from his chair, undid the final few buttons and tossed his shirt onto another chair next to me.

He had a very hairy chest, and I was right when I thought it would be as dark black as the hair on his head. And despite being hairy, it was clear he groomed himself well; there was a clear line between his chest hair and neck, he didn't have weird shoulder hairs or anything like that. He had a hard, flat stomach and I could see his biceps flex as he started undoing his belt, then the button on his pants. He drew out the suspense longer than I did, and slid just his khakis off, leaving him standing before me in just a pair of navy blue boxer briefs. I'd never seen boxer briefs before, and they barely contained his cock. He wasn't lying when he said it was big, it looked like a giant sausage crammed into his pants. How could it be comfortable dealing with that in your pants?

He started to pull his briefs down, but I reached out and grabbed his hand, stopping him. Then I shifted forward and reached into his waistband myself, I wanted to do this. I slowly, teasingly started pulling them down, off his hips until they got stuck on his massive cock. He reached down and adjusted while I continued to pull the garment down his legs. I wanted the suspense to last, so I focused on his muscular thighs as I helped him out of his briefs, and slowly made my gaze upwards again until the only thing I could see was his massive cock. It took up my entire field of vision, it was directly in front of my eyes. From the periphery, I saw him reach his hand and squeeze the base, emitting a droplet of precome from his cock head. I sat back further to take in this incredible specimen of a man.

He was tall, and he was muscular. And between his legs hung an amazing log that perfectly fit the proportions of his body. It was longer than mine, it was thicker than mine. And it hung off his torso majestically, with a pair or plump balls that were also larger than mine. He wasn't shaved clean, but was very neatly trimmed around his pubic area which made his cock seem even bigger.

"Just about 9 inches long, about that thick, too. Look," he said, gripping the base with his large fingers, "I can't even close my hand around its girth. Here, you try" he said, grabbing my hand and placing it around the hot, steel iron of his cock. It felt like a lead pipe in my hand, a little squishy but hard and firm; it radiated heat. I attempted to close my fingers around it and didn't come close, not even my entire hand to close around it. I cupped both of my hands around his cock and stroked him up and down a few times to prove that, yes, I could get my HANDS around his thick cock.

"Woah, this is amazing" I said in amazement as I stroked his cock between my two hands. Sometimes I would close my hands and tighten the grip, or loosen it and really feel his cock sliding across my hands. After a few moments he pulled away and sat back down in his chair across from me.

"So that's what I meant earlier."

"Your cock is amazing, Greg. Like...how is that even possible?"

"Always been that way; I'd look silly if I was this big and had a tiny little penis on me, wouldn't I?" he laughed. "You have nothing to be ashamed of, yourself, Michael. You have a very large cock by most guy's standards, I've been with a lot of men who are smaller than you are."

"Really?" I said, blushing.

"Hell yeah. Guys are going to drool when they see you. You have this cute face, and this great body. Keep working out, you look great. And that magnificent cock," he said, leaning forward to take hold of it once again. "It's longer than most, and thick. Mmmm, yours is like mine: about as thick as it is long." He gave me a couple more squeezes and leaned back in his chair, shifting his legs slightly so I could get a good look at his cock.

"Can I touch it?" I asked.

"Sure, but let's go over by those lounge chairs over there and get comfortable." And he picked up his drink and led me down onto the lower tier of the patio where there were a series of chaise lounge chairs set-up. He picked two close to the end in the sun, and laid down on his back with his head resting in his arms. He spread his legs a little bit and said confidently, "go on, play and have fun."

I was a little frozen and hesitated a bit, so he reached out and grabbed my hand and placed it around his thick cock. Oooo,I thought as I brought me other hand to meet it. I just held it for a moment, feeling its colossal weight in my hand. I turned it over and looked at the underside, the beautifully proportioned bulbous head at the top, and ran my fingers along the sensitive underside as he moaned slightly and adjusted his legs open a little more. I kept his cock in my right hand and reached down to scoop up his massive ballsack in my left hand, which again I just held to feel their shape and girth. And then to mimick his earlier action, I started squeezing and tugging on this from his body, while I rubbed my thumb along the underside of his cock where it meets the head. I was copying things I'd done to myself that I enjoyed like twisting my hands as I jack off his big cock. I was so curious, so I snaked my tongue out along his cockhead and slit, taking up some of the precome that had seeped out of him; it was the first come, other than my own, that i tasted. It was salty, but a little sweet, and I wanted more of him, so I took his cock head into my mouth briefly and quickly ran my tongue all around in circles before pulling off him. I looked up for approval, but his eyes were closed so I returned my mouth to his cock head and started my licking once again. I tried fitting more of him into my mouth, but I could barely get his head in, let alone anything else. I guess THIS is what he meant. My jaw was getting tired, and i knew my technique wasn't that great, so I started to slow down a bit. I so much wanted to get this man off, to show him how much he turned me on, but I didn't think i would be able to get him there, sadly.

I sat back on the lounger next to him while he rolled his head into my direction.

"Are you ok?" he asked me.

"Yeah, I'm just getting tired. Your cock is so amazing and I love playing with it, but I don't think you're enjoying this too much"

"What? Oh my god, yes, Michael, I am enjoying myself completely. What you need is a little time and patience, and practice. Don't beat yourself up, I am certainly not disappointed." He sat up and faced me now, our knees touching each other's. He leaned forward, touched the side of my face with his hand and initiated a slow, tender kiss. We kept our lips sealed as our kisses intensified. He lay me back on the lounge, and then immediately attacked my erect cock with his mouth, taking me almost all the way into his mouth before pulling up again, and repeating the same motion again and again. His right hand slipped between my legs and when I thought he would stop at my balls, his hand descended lower and he began to rub my perineum while continuing his oral assault on my cock. Then his thumb and middle finger were pushing my ass cheeks open, then I felt his thick middle finger rubbing up against my sensitive rosebud. And before he could proceed any further, I was crying out that I was coming, and I unleashed a second torrent of come into his hungry, waiting mouth. Once again he took a moment to clean up the remnants off my cock, then pressed his lips to mine so I could taste my saltiness on his lips.

Then he stood up, his giant dick dangling in the air, picked up his glass off the side table and walked back over to the bar to fix himself another drink. I was left spent and exhausted on the chaise lounge.

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4 Comments
kcniceguy4ukcniceguy4u4 months ago

Very nice always wanted to meet a nice guy in the CWE. Love the big homes off Lindell in the Westmoreland Place area. That would have been fun for a young guy.

AnonymousAnonymous4 months ago

So close to my first older man. I love the dynamic between these two and can’t wait to read more.

Exluke1Exluke14 months ago

Agree that Michael is really fortunate to be with Greg. I’m curious if Greg usually likes twinks and if he is just recently interested in much younger guys. Or preferably to have Michael ask him about his 3 most serious relationships. It would be interesting to know how long they have lasted and how they have maybe changed as he’s grown into his mid 40’s. He seems like too great of a guy to not have been serious with someone in the past.

MarcLuciFerMarcLuciFer4 months ago

Michael is so lucky to have someone like Greg as mentor, guiding him slowly and gently into things. Part 2 was written in such a realistic way that it felt like being there watching rather than just reading about it. Great job!

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Meeting Greg Previous Part
Meeting Greg Series Info

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