Checkmate

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timmywells
timmywells
1,748 Followers

"I wish you told me," I said. "I would have bought you something. Taken you to dinner."

"That's okay," Ryan said. "I like this better."

"Wait!" I said, jumping up and heading back to the kitchen, and after a brief search, found what I was hoping would be in the handy junk drawer.

"Now this makes it a proper cake," I said, putting the little green candle on top of the cake and lighting it up. "Don't have 19 of them, so this will have to do."

The lights were dimmed, making Ryan's eyes sparkle as he leaned close to the cake. He looked over the table at me before looking back down at the cake for a long minute and then blowing it out with a quick puff.

"Delicious!" I declared after letting Ryan cut the cake in half and splitting the one side in two, the rich chocolate melting in my mouth. "Even though I can feel myself getting fatter with each bite."

"You're not fat," Ryan said.

"Hope you remembered to make a wish before you blew out the candle," I said to Ryan as I savored the last bite of the cake while deciding whether or not to cut into the other half.

"I did," Ryan assured me. "I wished..."

"Wait," I said. "I don't think the wish will come true if you tell."

"If I don't say what it was, then I know it won't come true," Ryan said. "I wished that after we finished the cake, you would tell me that you didn't want to play chess tonight, and instead you wanted me to stay here with you overnight."

I took a deep exhale as Ryan spoke, and he quickly added, "You don't have to do anything to me. I just don't want to be alone."

"Sounds like a one-night stand," I said. "I'm too old for that sort of thing."

Ryan's face fell as I spoke, watching me while I folded the box up around the rest of the cake.

"I would like you to spend the night though," I said with a nervous smile. "Very much so."

...

Chapter Six: Reflections

I looked at my reflection in the mirror as I brushed my teeth, wondering if I was doing the right thing. In a minute I would be going into the bedroom where Ryan would be waiting. I would undress this man-child and we would explore each other's bodies.

What would I find under those clothes? I steeled myself to try and expect just about anything, but when I looked in the mirror I was reminded that I wasn't all that great myself any more.

The dark pelt of hair on my chest was now sprinkled with grey and the waist was a bit thick, and while I always kidded myself that I might not look 57 dressed, I looked at least that naked. I pulled my satin robe off of the hook on the door and wrapped it around myself before taking a deep breath and walking out into the bedroom.

Earlier in the week Ryan had arrived at my place without his pocket protector, proclaiming that while he had given it up because of my constant kidding, he felt naked without it.

Now, standing next to my bed, Ryan was truly naked. His clothes neatly stacked on the chair by the wall, Ryan had first had his hands cupped over his privates, but now took the hands away and stood there trembling as he exposed himself to me completely.

It was not only the most courageous thing I could remember seeing in quite some time, it was also the most erotic sight I could recall, once I got over the initial shock.

Ryan was visibly trembling as I approached him, his bony shoulders quivering as he looked down at the carpet. His 5'6" frame, that couldn't weigh more than 125 soaking wet, was pale and virtually hairless, with only a modest tuft of pubic hair braking the smoothness.

Whatever misgivings I may have had about Ryan disappeared when my eyes saw what he had been hiding; a penis that, while it may have been rather slender, was surprisingly long and made it quite clear that Ryan was indeed a man in every sense of the word.

I was now standing right in front of Ryan, way too far in to back out now, but I didn't really want to back away. Instead I said the words that seemed to fit.

"You're beautiful, Ryan," I said softly, lifting his chin with my hand and raising it up to kiss him.

His eyes were watering as he closed them when my lips made contact with his, and I nippled my way around to his neck and his shoulders after the initial kiss broke off. Ryan's hands were tugging at my robe, trying to pull it off of my shoulders, and when he managed to get it off he buried his face in my chest while his hands went lower.

"Easy," I said after Ryan's hand grabbed my cock. "We do have all night."

"Sorry," Ryan said softly. "I'm excited."

"I know," I told him. "So am I."

***

Chapter Seven: Relaxing Ryan

I eased Ryan down onto the bed, savoring the sweet smoothness of his skin and for some reason finding myself excited by Ryan's nervousness. My hands strayed over his flat stomach, going beneath his belly button and grazing the timberline of his pubic hair before sliding back up his body.

I resisted touching Ryan's beautiful manhood, but as I kept rubbing and stroking his body his cock began to get hard, and finally I took the slender shaft in my hand as it began to point upright. His entire body was quivering as I gently stroked his beautiful organ a couple of times before putting him in my mouth.

Ryan was so hard - one of the virtues of youth that I had forgotten - and as my lips slid down his throbbing manhood I knew Ryan wasn't going to last long. He was grabbing at my shoulders and his legs were churning when I felt the surge race through his dick an instant before he came.

And how he came! His cock kept jerking in my mouth as wave after wave of his seed spurted into my mouth and down my throat, and I had to struggle to keep from being overwhelmed by the force and volume of his orgasm.

Ryan was so emotional afterward that it became contagious, as as we hugged I had to fight back a tear of my own. I had never witnessed anyone who had enjoyed an orgasm as much as Ryan, and he was intent on making me as happy as he was.

He rolled me onto my back and straddled me, with his crotch on top of mine, and as he ran his hands through my chest hair I could feel his balls rolled over my cock, which was pinned to my belly.

"Wanted to do this from the first minute I saw you," Ryan explained as his fingers raked the salt and pepper fur that covered my chest.

"Feels nice," Ryan sighed, his hands finding my nipples and tweaking them gently.

"Amen," I agreed, his touch making me shiver.

"You're like a bear," Ryan smiled. "So big and warm and furry. Wish I was hairy like you."

"I think you're perfect just the way you are," I assured him.

I let him take my wrists and pull them up over my bed, and when he buried his face under my arm and started to lick and nibble my armpit hair I felt my cock stiffen. This was something that Arthur used to love to do, and Ryan was inadvertently bringing back old memories as his teeth lightly teased me.

"Sorry," Ryan said when he looked at the expression on my face. "Did I hurt you?"

"No," I said, smiling when I realized there was a tear trickling from the corner of my eye. "Just the opposite. I'm just enjoying you."

"I can feel you getting hard," Ryan said as he ground himself into me. "Do you like this?"

"Very much," I sighed as Ryan lifted himself off me a little and reached down, wrapping his hands around my member and giving my stiffening cock a pull.

"Wow, you're even bigger than I thought," Ryan said, and I shook my head, telling him that we were pretty much the same in that department.

"Yours is way thicker," Ryan explained as he climbed off of me and knelt at my hip, sliding my foreskin down before licking the crown.

I groaned as Ryan's mouth took in the head of my cock. It had been nearly two years since I had experienced this, long and lonely months spent thinking of the past, and as I watched Ryan's mouth slid down and down I realized how lucky I was.

This sweet young man seemed to think that I was doing him a favor by befriending him, when in fact it was just the opposite. I had forgot what being happy felt like, and watching Ryan's lips sliding up and down while his eyes twinkled with joy warmed my heart.

I was going to cum, and Ryan was doing everything he could to make it happen. His hand was kneading my balls while his mouth dove nearly all the way down my shaft, his face grazing my pubic hair each time.

"Oh," I whimpered, clutching the bedding as I came, and Ryan kept going up and down as some of my semen trickled out of the corner of his mouth.

Ryan looked up at me as I went limp in his mouth, and after he let go of me I pulled him up and hugged him.

"So good," I sighed as our bodies embraced, and I didn't let him go for the longest time.

***

Chapter Eight: Taking me.

"I want you to," I said to the lad who had coaxed two more orgasms out of my old bones by then.

It was 3 in the morning, and Ryan was showing no signs of slowing down or wearing out. He had asked me to do something to him, something that he had never experienced before, but even if I could have managed to get hard again, I really didn't want to, at least not then.

"I don't know how," he said as I handed him the lube.

"You'll do fine," I assured him.

For whatever reason, I needed Ryan inside of me. In my life I wasn't usually the bottom, but I felt like I should be with Ryan. His finger was tentative at first, probing me with his oiled finger, but when he saw me reacting by moving my hips along with his motion, he started probing deeper.

I got onto my hands and knees as Ryan greased his long prong, and as he climbed behind me he fumbled around a little at first.

"That's it," I sighed when I felt the tip of his dick at the entrance. "Give it to me."

"Ooohh!" Ryan gasped as his dick slid in the tightness, and as he sank all of it into my rectum I could feel his hands shaking as he held my hips before pulling back out.

"Oh, that's good babe," I said as he slowly moved in and out of me, his slender cock feeling good as he impaled me so deep.

"Gonna cum," Ryan grunted, way too soon for me, but he was too excited at this new sensation.

I felt his dick jerked inside of me as the warmth filled my cavity, and I shivered when he deflated member slithered out soon after he finished cumming.

"Sorry I came so fast. It was so tight and it felt too good," Ryan said as he hugged me from behind while I sank to the bedding. "Did I hurt you?"

"No babe," I assured him. "It was so good. You'll last longer next time."

"I like that."

"Like what?"

"When you said next time," Ryan said, kissing the back of my neck.

"Well, I told you I'm not one for one-night stands," I reminded him.

"I love you Steve," Ryan said softly, and while I didn't answer, if I had to I could have said the same thing to him.

I know that Ryan will find somebody his own age someday, but until he gets bored with this old man, I'll love him too.

***

thanks for reading

timmywells
timmywells
1,748 Followers
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6 Comments
ASmokingGunASmokingGunabout 9 years ago
Almost perfect

tw this one has all of your strengths; the themes you write best, characters that are familiar enough to be comforting but not enough to be repetitive, and a gentle tone that is not exploitative. Well done sir, I salute you upstairs and down :)

AnonymousAnonymousover 9 years ago
Very romantic

Great story, very romantic and... sensual, if I can put it this way. I enjoyed it very much

EroticLitKittyEroticLitKittyabout 12 years ago
Incredibly sweet

A very good read

Darby4186Darby4186almost 13 years ago
Thank you

A tender story for us older men who wonder what's out there after 50 and alone. Your talents of story telling are good - you create a beautiful mental picture and describe feelings and emotions in a realistic way. I wish you would do as thorough of a job during the scenes of passion. You seem to rush through them sometimes. Enjoy the moment. I really enjoy reading your stories

AnonymousAnonymousalmost 13 years ago
loved it

A beautiful coming of age Story.

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