An Afternoon with Charlie

The following story is a little more autobiographical than I thought it would be - most of it is true. If you have any suggestions or comments, I'd love to hear them. I am always looking to improve my writing.

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After my first encounter with Charlie, I was hooked. Whenever I had enough time to make the drive over to see him, I would, and Charlie would suck me off. As the idea of being with another man (and an older one at that) became less alien to me, I began to wonder about the other things we could do. I wanted to know how it felt to kiss another man, to feel his bare torso with my hands, to give him pleasure. After yet another mind-blowing liftoff courtesy of Charlie, I expressed my desires to him while he handed me the customary washcloth to clean up.

"Charlie, you know how much I like all this-"

"But you want to try something else." He grinned at me. "I had a feeling that was going to happen. I've always enjoyed playing ambassador to visiting dignitaries," he laughed. "And there's lots of places to explore in this land. What do you want to do?"

I suddenly felt flushed, my face betraying my discomfort at the frankness of his question. "Well, I, uh-- I want to know about fucking," I blurted out.

"Fucking? Who's doing the fucking, me or you?"

"Well I am curious how it feels to be fucked. I've seen some videos..."

He chuckled. "And you want to know why anyone would want a dick in there?"

I laughed. "Yep."

Charlie replied in an almost paternal tone, "I appreciate your enthusiasm, but I think you're jumping the gun a little bit. You've never kissed a man before, is that right?"

"No."

"And it probably follows that you've never sucked anyone off either, right?" The line of questioning was beginning to sound condescending. Charlie was adept at reading me and quickly reassured me. "Hey, I'm not making fun of you, I'm just thinking out a good road map for you. If you don't have anywhere to be, we could maybe try a few more things..." He grabbed my arm and slowly rubbed it.

I felt the sudden sinking feeling in my chest as my anxiety returned. I took a deep breath, looked up from the floor, and met his gaze. "OK, Charlie, I think that's a good idea."

"Alright, well this time you are the one in control. I want you to go as slowly as you want, enjoy yourself, do what you feel! And remember, we can stop whenever you want to." He stood up and motioned me to get up. When I did he slipped off his shoes and hopped right in the middle of the bed with a meaty 'whump' sound. He looked over at me expectantly with his arms outstretched. "What do you say we start with a hug?"

He spread his legs and I climbed up to him on my knees and let my hands go to his waist, sliding up to his armpits. He smiled and folded his big arms around me. It was such a warm feeling; he rubbed his hands on my back and whispered in my ear, "You're a beautiful young man, do you know that?" I looked into his sapphire blue eyes and touched his lips to mine. In the back of my mind I had thought that kissing a man must be the opposite of kissing women, but I was surprised at how similar it really was. He had warm soft lips that moved in response to mine. I opened my mouth, Charlie took a deep breath and moved his tongue in. I felt the hairs on the back of my neck stand up and a tingly vibration travel up and down my spine. He must have sensed that I had gone limp because he rubbed his hands up and down my back, finally giving my butt a squeeze.

I pulled back finally and looked at him. "Wow" was all I could muster.

He grinned, "I figured you were a good kisser. Your girlfriends ever tell you that?"

"Never" I replied.

The look on his face was a mixture of surprise and pity. "Well that's a real shame. They must not have known how lucky they were." His voice brightened a bit. "Alright, where are we going now?" He asked expectantly.

I smiled briefly, sidled back a little bit and felt that familiar anxiety again; I was at a loss as to what to do next. The fantasies I had had about Charlie all seemed to flow so organically from one activity to another. It almost felt like saying anything out loud would make it contrived and inauthentic. However, even something as simple as hugging and kissing was almost complete sensory overload. Step by step, for me, at least, was the best way. Charlie pulled another pillow under his head and watched me placidly.

"I just want to touch you right now." I said. Charlie relaxed into the bed and said nothing. I ran my hands from his knees and up to his torso, trying to feel every bit of him. I gently untucked his shirt from his pants and loosened a couple of the bottom buttons. I said softly, "Would you please take it off for me?"

Charlie said, "You don't have to ask, but it's nice that you do."

He quickly undid the buttons and deftly folded the shirt, placing it on the nightstand. He must have anticipated my next move because he took off his white undershirt without a cue. Finally I got to see him bare chested and it was almost exactly as I had imagined. He had not a lot of dark hair, but he was covered with wispy, short hair that added a soft glow to his skin. He had a barrel chest with prominent pectorals and massive, wide shoulders. As I crawled onto the bed to straddle him, Charlie closed his eyes and I ran my hands up and down his chest, feeling his silky, soft warmth. I paused briefly and unbuttoned my own shirt. I tossed it to one side of the bed. Without opening an eye, he said, "You'll get wrinkles that way." and chuckled.

I leaned down and slowly put his chest to mine. Charlie reached around and rubbed my back, his hands pushing lower and lower, reaching underneath my pants to grab my bare ass. "Ah, they're like two pillows, what a great ass you have."

I reached around and fitted my hands under his waist, pulling my chest to his while he continued to knead my butt. The feeling of his skin on mine was like soft velvet. Charlie lifted his head up for another kiss and I obliged. Time seemed to stop briefly as he put his tongue in my mouth again. Another powerful chill went up and down my spine. I whispered, "I'm glad you don't have an agenda, Charlie, because at this point I'd probably agree with anything you'd say." I pulled back and laughed a little.

"Who's to say I don't have one!" Charlie laughed. He looked up and his eyes widened. "Gosh you're practically hairless, do you even shave yet?"

I nodded. "Every few days. But if my dad was any indication, I'll probably be pretty hairless my whole life."

Charlie said, "Well there are worse things in this world, and it's easy to see that fine body of yours."

"I think you're buttering me up for something." I laughed. I sat up and gave a gentle tug on his belt.

Charlie smiled. "You sure you're ready for this?"

"I think so."

He deftly unfastened his belt and with a little hop, they were off in five seconds. He again folded them and put them on top of his shirt on the nightstand. All that remained were his boxers, but I could see a bulge and a slit in the shorts that showed white skin. I suddenly felt an odd twinge in the back of my mind. What am I doing here? How did I get in this situation? Charlie saw the change in my face, reached up and patted my arm

"Hey, you don't have to do anything you don't want to. If you want to stop here, that's OK." He studied my face. I looked away and weighed the options, deciding that if I didn't go through with this, I'd probably regret it. I looked back at Charlie and looked into his eyes, moving my hand to the slit on his boxers.

Charlie gave a small grin and slowly pulled them down. I saw the line of his boxers descend and revealing his dark pubic hair. I saw his thick, white, half-erect penis slowly emerging and when the boxers finally got to the head, his cock jerked up reflexively. I looked in admiration as I finally saw his big, uncut dick.

"My goodness, Charlie, you praised my dick, but look at you!"

He smiled and whispered, "Shh, He knows we're talking about it!" I looked down and it had begun to rise, each tiny throb sending it just a little higher. He slipped the boxers off, folded them, and put them on top of his pants.

I looked at him in all his naked glory and he smiled again. "Are we going too fast? You still ready for this?"

I nodded, knowing that I was about to cross a line of some kind, perhaps just a line that I had built up in my mind. I reached out for his dick and felt it; it had a strange, rubbery feeling that seemed familiar but it was odd that I didn't feel any sensation. Charlie flexed it and it pulsed. We locked eyes as I was kneeling over his dick. I pulled his foreskin back. He said, "I want you to look at me when you put it in your mouth for the first time. I want to see the first dick your virgin mouth will take."

I looked at Charlie as I lowered my head closer. His eyes were wide with excitement. He had told me that breaking in virgins was what he liked best and he was on edge with anticipation. I broke my gaze with him and looked away.

"This is only ever going to happen once, Charlie. Are you going to want to meet with me after this, or are you going to want to find someone else that's never done this before?"

He frowned and said, "You are right, there is only one first time, but there are many other aspects of sex that excite me. I can't promise forever, but I can promise that you will be no less attractive to me after all this. If anything, you'll be even more so."

His change of focus had softened his dick and it had become loose and pliable in my hand. I looked at him thoughtfully and replied, "Alright, Charlie, I trust you. If I can say anything for certain about you, it's that you've always told me the truth."

He flashed a grin. "Don't let my dirty talk put you off. Just because I want to watch you suck a dick for the first time doesn't mean that I don't respect you, but it does turn me on. If we're going to enjoy this whole thing, we're going to have to trust each other."

I nodded. "That makes sense. Pretty much all of my experiences with women were basically fumbling in the dark and zero communication. That first time you sucked me off was literally the first time I had had sex in the daytime with my eyes open. This whole thing is new to me."

"Some people live their whole lives having sex like that, and then they wonder why their relationships falter. It's no fun living like that." His eyes unfocused and he looked off in the distance.

When I gave his penis a light squeeze, he broke his reverie and smiled again. I knelt down, peeled his foreskin back again, and put his limp dick in my mouth. I was struck by how warm and soft it was, and it had the same rubbery quality as pussy. Charlie gasped a little as I ran my tongue over the head of his dick, getting my first taste of his precum - salty and sweet at the same time. He was soon just as hard as he was before and I could only fit about half of his dick in my mouth.

He lay back on the bed and sighed a big sigh. "Wow, You're sure this is your first time sucking dick? You're a natural!"

I came up and jacked his dick slowly. "Well I kinda thought the Golden Rule would be useful here, except with dicks." We both laughed.

I ran my hands down both of his thighs and took as much of his dick as I could. Suppressing my gag reflex was very difficult at first, but Charlie kept encouraging me to try. "That's it, boy, take it all in, get it down your throat," he groaned.

After I had gotten most of the gag reflex under control, he sat up and asked, "Is it alright if I hold your head?"

I looked up and nodded my head "yes" with his dick still in my mouth. He put his hands on the sides of my head and began thrusting his dick slowly, trying to get it further in each time, growling, "That's right, take it all." I took my hand from his thigh and put in between his legs and fondled his pillowy balls. He groaned louder and moaned, "Oh, my sweet young man, you make me so hard. You're going to make me cum."

I was holding up alright but my jaw started hurting and I pulled away. I wiped my mouth and looked at the pool of saliva around his balls. "You alright?" He asked.

"Yeah, I'll be fine."

He looked at me furtively and whispered, "I want to cum in your mouth, is that OK?"

I said, "Sure, but I don't think I can handle any more face fucking."

"You ever heard of tromboning?"

"No."

"Put my dick in your mouth and jack off the rest of it with your hand."

"OK."

I put his dick in about halfway and slid my hand up and down the shaft. The saliva made it really slick. Charlie took a deep breath in and said, "There you go, that's gettin' it. I want to shoot my load in that virgin mouth of yours!"

I sped up a little and felt his dick begin flexing. I slowed down a little to see if I could make him last a little longer. When his hands clutched at the bedspread and his thighs flexed I could tell he was close. Every time I felt his cock swell and I heard him groan I would back off. After about five minutes, he muttered, "C'mon, boy, c'mon and finish me off!"

I sped up and put just the cock head on my tongue. His dick was rock hard and he began whimpering. "Oh, ah, oh, ok it's happening, I'm cumming!"

I saw his balls suddenly suck into his scrotum and felt the first watery squirt on my tongue. He groaned even louder and the second spurt came out with such volume and force that it hit the back of my throat. The third squirt was the biggest and the cum began to run down the sides of my mouth. Charlie's moaning subsided and his dick ejaculated the last of his load. I held his cock there in my mouth for a moment, savoring the salty load oozing down the sides of my mouth. He pushed my hand away and milked out the last drops onto my tongue and sighed.

I held his dick in my mouth just a little longer, savoring another important milestone in my sexual life. I had given another man pleasure and while I had a few other milestones ahead of me, I was happy that I had had the courage to go through with it.

Charlie slipped off the bed quickly and tossed me a towel from the master bathroom. In a couple of swipes my mouth and face were clean again.

He beamed at me as I handed him the towel. "You were great! You've gone a little further, haven't you? Now give me a kiss while we're both standing."

I held Charlie's naked body to my half naked one and he folded his arms around me. "You're a special young man." He said, as he pressed his lips to mine. The same electric chill traveled up and down my spine once again.