Initiated

He savored the sight of me, cum all over my face, then had me take a shower. When I had dried off, he installed a butt plug inside me- he didn't ask my permission, he simply did it, and I loved it. Then he put a jock strap on me and had me get dressed again in the tiny swim trunks. He also put aviator sunglasses on himself and me- we looked cooool. My cigar had gone out, but there was still about 5 inches of it.

He said, "you're gonna finish this, buddy. You're not going to let it go to waste. Think of it like finishing your vegetables, heh." He tapped all the ash off it and shoved it back in my mouth. He put the lighter to it and obediently I puffed, puffed, puffed till it was burning good again. He told me we were going to the pool.

I said, awkwardly around the cigar, "shir, I'm sho turned on by you and shmoking shigars wif you, everyone will see my huge boner in these tiny swim trunks, my dick may even pop right out". Puff.

"That's what the jock strap's for, to hold that in. Believe me buddy, no one at that pool will know how damn horny you are except me. How'd you like being marked by my cum?" Puts cigar in his grinning mouth.

"I fucking loved it, shir. It was an honor and I'd do it again in a heartbeat." Cigar puff.

"Don't worry, you'll get the chance to do it again, I'll make sure of that, heh. In fact, you will do it again whether you like it or not." Cigar puff. "Turned on again so soon?"

"Yesh shir, I feel like I could explode. I'm sho horny I'm shwooning, I could go off any minute".

"Well reign it in boy. You'll get your chance to cum and I'm looking forward to it, but not right now. And I'm looking forward to taking that butt plug back out...." He grinned, and his cigar angled up in his mouth. I did the same. He puffed smoke into my face. When did I start letting this man order me around and degrade me like this? But I loved it, and I felt I could trust him, and he wasn't doing this to me because he was really a controlling jerk, but because he knew in some way deep inside that I wanted it.

I had had the cigar in my mouth since he put it back in and relit it; he said, arm around my shoulders, "take a good puff and take it out of your mouth, then we're going to keep them in our mouths all the way to the pool, like when we first came in. How bout it, buddy?"

"Sounds good, sir!" With that, we chomped our stogies once again and headed to the pool. We puffed down the hallway leaving a trail of smoke as people gave us looks. Once again, badasses. Outside we found a secluded area by the pool, in the shade of palm trees, and laid on some lounge chairs. We applied suntan lotion and Joe went to get us some drinks. I sat there, beer in one hand, stogie in the other, hot older guy by my side (I laughed when he said the other people at the pool probably think I'm his nephew) and I thought, it doesn't get any better than this. As the alcohol of a third and fourth beer took effect, I reflected on the day: finally met the man of my dreams, smoked my first cigar and it's so big I'm still smoking it, got to blow him and really really loved it, and now here we are relaxing by the pool and he's got more in store for me...

Finally, about an hour later, the sun had gone down, my cigar and his were down to the nub. At his direction, I put it out in the ashtray, finished my most recent beer, and we began the walk back to the room. Did I mention I had had just about a constant erection the entire time? And, maddeningly, I couldn't do anything about it because I was out in public among a lot of people at the pool, but fortunately it was hidden by my jock strap. Also, I was really getting used to the idea of having something penetrate my asshole thanks to that butt plug Joe had put in. While my dick begged to be stroked and to cum, my butthole seemed to squirm around the plug, as if yearning to be filled by something bigger, and alive... like a man.

We got back into the room, and I stood there awkwardly as if needing further direction from Joe. He reached into a cigar box and pulled out another stogie. This one wasn't as big as the last, but it was still about 7 inches- a Cohiba, I believe.

"Got this from a buddy of mine when he went to Cuba" he said, as he cut it, then he lit it up. Chomping the stogie and grinning, he looked at me with a hunger in his eyes. He grabbed my shoulders and turned me around, sort of pushing me toward the bathroom, puffing along the way. He pushed me till we got to the counter and I was sort of bent over it, palms on the counter holding myself up, looking at myself in the mirror. Quickly, desperately, he pulled my trunks down, then his own, I saw in the reflection his dick standing straight out, he grabbed a condom from the box next to him and put one on, applied lube, pulled the butt plug out and tossed it aside, put his cigar down, kissed the side of my neck, and shoved the head of his penis inside me. I gasped with joy mixed with a little pain. At a quick but restrained pace he buried all 8 inches inside me.

"Ohhh FUCK!"

"Like that, buddy?" He grinned from ear to ear as he held one meaty arm across my chest, the other hand caressing my face.

"HELL yes, SIR! I fucking LOVE IT sir!!!!!" I was having the hottest time of my life. He grabbed my hair and pulled my face up to look at myself in the mirror getting fucked.

"Look at yourself. LOOK what I'm doing to you. LOOK AT YOURSELF getting FUCKED. Do you like that???? Is that how you like seeing yourself?"

"Oh, YES sir!!!! I fucking LOVE it!"

"You like being fucked by me? You like feeling my big cock inside you"

"Yes yes YES!!!!! I love your cock inside me, so much, thank you for fucking me SIR!"

"My pleasure. I'm enjoying your ass. I think I'm going to make a habit of fucking it."

"Nothing would make me happier, it would be an honor, SIR!"

with that, I felt him shoot his load inside the condom inside my ass, and I let loose all over the mirror. I panted like a dog and he put his cigar back up to his mouth, and puffed a cloud of smoke toward my face. He didn't pull out though. He actually picked me up by the underside of my thighs, and carried me over to the bed, his cock remaining inside of me the entire time, although it was quickly softening and fell out as he set me down on the edge of the bed. He got a pack of cigarettes out of nowhere and stuck one in my mouth, then lit it. As i puffed obediently like usual, the cigarette sort of dangling and jiggling in my mouth, I couldn't help but be a little surprised. A cigarette was nothing like the large manly stogie he had previously had me puff on.

He said, "that first cigar was a treat, and you took to it well, but you're not a true cigar smoker yet. But don't worry, man, you will be. The training begins tomorrow." I nodded, only half understanding, and smoked my cigarette. He ordered room service and we watched tv and ate it and drank beer. I smoked more cigarettes out of the pack he'd provided. I laid back, and dozed off during the news. A few minutes later I woke to something in my mouth- a hot dog? No it was Joe's dick, thrusting in and out, in and out. Waking up to it, I felt a sort of urgency, and jumped up, got down on the floor, and started eagerly sucking his dick ( he was sitting on the edge of the bed). I sucked it and wacked it off at the same time, he had his hand on the back of my head and was quietly encouraging me,

"yeah, that's right, just like that, buddy, good job." after a few minutes he shot his load, but this time it mostly got in my mouth and I immediately swallowed that, and there were a few drops on my cheeks and one big drop dripping out of my mouth. On my knees, I looked up at him, eyes imploring, yearning for his validation, his approval, while his seed dripped off my chin.

He said, "Good job buddy, good fuckin' job again. You're amazing, you know that?"

"I think I might be falling in love with you, sir."

*

NEXT TIME: The next day, to train me to become a "real cigar smoker" like him, Joe makes me smoke cigars all day, one after the other! Woke up at 10 am, went to bed at 2 am, that's 16 hours awake and each cigar takes about an hour, =16 fucking cigars! Plus more cocksucking, ass fucking, and other things in store!