When I was 14 years old I had a next door neighbor who was 19 years old. He was a good looking boy, 6'3" tall, about 193 pounds and a very athletic body.
He had just gotten a new car. He was so proud of his new truck. It was cherry red and spotless. He washed and waxed it every other day.
I was outside one day playing with my baseball when I made a terrible error. As I swung the bat, a bee started for my face and I totally lost control. Guess where the ball went. That's right, directly into his driver's side window.
I was stunned. I went over and rang his doorbell. He answered and I said, "I'm so sorry Chad, I accidentally broke you car window, please don't be too mad, I'm really sorry."
He just looked at me. He knew that my family was not the richest family in the world and asked me how much I could him to repair it.
"I don't know." I said. "I don't think we have any extra cash right now. I could work it off."
"No." He said. "We will take of this now."
I was puzzled. I had no idea what this guy wanted to do right now. No money, no work?
"Umm... how?" I asked.
"Are your parents home?" He asked.
"No."
"Come inside."
He brought me inside and we walked back into his bedroom. His room was clean and a great big American flag hung on the wall. He went over to his chest of drawers and opened the top drawer. He reached in and pulled out a long black paddle. It was about one and a half feet long and about five inches wide. It was only about half an inch thick.
"We will work this out on your bottom." He said.
I was shocked. I did not know what to say.
"If you agree to this, I will not tell your parents and you will not have to pay any money. I will warn you though, this is going to hurt pretty bad. The whole thing will take about an hour and a half to finish. You won't be happy when I am finished."
I agreed and asked him what I needed to do. I had been spanked before. How much worse could it be than one of dad's?
"Ok." he said, "I need you to take your pants and underwear off and pull your shirt up under your armpits. Bend over and put your hands in the seat of this chair."
"Pants off? Why do I need to have to do that?"
"I need to be able spank you the most painful way I can. That window is going to cost a lot of money. JUST DO IT!"
I slowly removed my pants and underwear and got in position. I was so vulnerable. My bare butt was sticking out and my penis and testicles were hanging down so he could see them. I was so embarrassed.
He started to punish me. At first he only used his hand. He smacked my butt firmly, but it only stung a little. He started to get faster and faster though and before I knew it, my butt was stinging pretty good. I counted 100 smacks with his hand.
"That was just to warm you up." He said. Now the real punishment starts.
He took the large paddle and touched my left butt cheek with it. He explained that he would be starting with 20 licks.
The first five licks were very hard and about five seconds apart. They all hit me in the same spot.
The second five were the same way only on my right cheek.
The next five right in the center.
The last five were even harder and he spread them out all over.
Rest now. He said.
After about one minute he explained the part of the punishment would be even more painful. He started working me over really hard. Five licks at a time he hit my left, then right, and alternated for a long time. I lost count after 55.
I was hurting so bad. He said I had not felt anything yet.
He finished the pounding with the paddle and then went and got a large thick leather strap.
He said 40 with this and then only one more phase for today.
He beat my butt relentlessly. Ten went fast, ten very slow, fast and slow until he was done. I had never felt pain like this before. I was beyond crying, all I could do was moan.
Ok. Now for the final phase of the day. He took a thin and flexible cane and swished it through the air. Now I had never been punished with a cane, but a British I knew had and he said there was no punishment like it.
He said we will conclude todays punishment with 12 strokes of the cane.
He took his shirt off and was standing there swishing that cane through the air. My member perked up when I saw his sculpted chest and abs.
SWISH.... CRACK!!!!! The first stroke took me totally off guard. I screamed as the searing pain penetrated every inch of my body.
Each stroke was spaced out one to two minutes. It hurt so bad. Even with all this pain, my penis was still fully erect. I couldnt figure out why.
When he finally finished beating me, he said, Ok, this was the first of three days. No punishment tomorrow, but the day after you will be here. Then a day off and then the day after that. I expect a little more respect from you. If you are going to get a hard on in my room, you should have the courtesy to let me watch you take care of it.
I was confused. This guy had a girlfriend. I have heard them going at it more than a few times as I sat outside his bedroom window and rub one off.
He told me to do it or he would punish even more. So I took my penis in hand and started stroking it. He got a hard on as well. It was huge. He didnt take it out though.
It only took me a about 30 seconds to shoot my load and it landed on his chest. He gave a quick three smacks with his hand and said to be more careful next time. How I wanted to see his tool. It looked huge through the soccer shorts he was wearing.
Do not let your parents see your butt tonight. He commanded.
No problem. I responded.
The next session was not as painful, but was a lot more intense. There was not a lot of spanking involved, but my butt was used in the punishment.
I will let you use your imagination on that one. You can always e-mail me for more details if you want. Perhaps in the future I will post the rest of the story. Depends on the response I get from this one.
This all happened when I was 14. That was only 4 years ago.