His Pain, My Pleasure - Summer of '88 - Part I

by Matt B.

Once in your life you meet that one boy who from first glance takes your breath away. It was that way for me when I first saw Brian. Each summer I take two weeks vacation and go to a little cabin which is right on Lake Michigan. It was pretty quiet the summer of '88. There was only one other family around and they were two cabins up from mine.

The second day I was there I was sitting out back in a lawn chair, looking our over the lake. It was at this time when I saw Brian for the first time. He had on a tee-shirt and a pair of tight fitting shorts that caused me to gasp when I first saw him. His little butt was well-formed and looked as though it wouldn't be able to fit in those shorts much longer. I only saw his parents for a short while before they left that morning, leaving him to hang around by himself.

I was really enjoying the view from my chair. Looking at him was definately better than looking at the surrounding scenery around us. He looked over my way a few times, and I did my best not to let him know that I was looking at him. After about an hour the boy went back inside his cabin and I decided it was time for me to go back in and get something to eat.

While I was doing the dishes after eating I heard a loud crash. I immediately went outside to see what had happened. There stood the cute boy next to the broken window of my sunroom. He looked pretty nervous, and I soon saw why. On the floor of my sunroom was a baseball - in the boy's hand was a bat. Anyone could have put two and two together.

"I'm real, real sorry mister," the boy said. Under normal circumstances I may have confronted the culprit, but how could I get upset with such an adorable kid?

"What's your name?" I asked him.

"Brian," he replied.

"How old are you Brian?" I asked him.

"Ten," he answered.

There he was standing right in front of me, and I couldn't help staring at those tight shorts he was wearing. "Where are your parents?" I asked.

"They work at the aquarium," he told me.

"So you stay here by yourself all day?"

He nodded.

"You're gonna tell my parents I broke your window, aren't you?" he asked.

"Well Brian, I'm sure you didn't break the window on purpose, but you do need to be taught a lesson so that you'll be more careful," I told him.

"What do you mean?" he asked.

"Well, I suppose I would be willing to forget about this if you allow me to give you a good spanking," I told him.

His look became even more nervous. "You mean you won't tell my parents?" he asked.

"That's right," I told him. "But the spanking would hurt, and I don't think you would be doing much sitting down for the rest of the day."

He still seemed more worried about how his parents would react. "Okay, you can spank me," he said.

"You sure that's what you want?" I asked. He nodded. "Okay, I suppose I can give you your spanking right out here since there is no one else around."

I walked with him over to the picnic table and sat down on the bench. I looked at his cute little face and could tell he was a little scared. "Just relax Brian," I told him. "The spanking is going to hurt, but you'll be okay."

I took his arm and pulled him across my knees. His butt looked as though it were about to rip through those tight, little shorts. I placed my hand on his bottom and began to gently rub it. It felt really good having this cute boy over my lap with my hand rubbing his butt. I knew I could have had my way with him. Still, giving him a disciplinary spanking was enough to satisfy me at the time.

I raised my hand and brought it down hard upon the seat of his tight shorts. He jerked a little. He gave a quick, "Ow." I swat him over and over, and a few times he tried to reach back and protect his bottom with his hand. I held his hands behind his back to keep him from doing this anymore. I gave him twenty-five swats, which he took pretty well. His eyes were a little watery when I lifted him off my lap, and he began to rub the seat of his shorts.

"Is that it?" he asked.

"Not quite, that was only half of it" I replied. "I'm going to give you the second half of your spanking, but first I'm going to pull your shorts down."

Now he looked really scared. "Do you have to?" he asked me.

"I want this spanking to teach you a lesson, so it will do you more good with your shorts down," I told him.

"But I don't have any undies on," he told me with embarrassment.

"That's okay. I'm going to give you the rest of your spanking bare-bottom," I answered. "Besides, it's just you and me out here."

I unbuttoned Brian's shorts and lowered the zipper. I then slowly slid them down his knees. His little, 2" penis pointed straight out at me, hard as could be. He didn't seem too concerned about that. I took his arm once again and gently assisted him back over my knees. I now had those plump, little buns sticking straight up at me. They were a little pink from the spanking I had just given him.

to be continued...

More stories byMatt B.