James, 33, and I had been friends for about four years when this first of many true events occurred. Sure we had (and still have)the same interests in spamking and S/M and had done some things together, I always being the Master over him. However, we knew each other very well. He is still my best friend and we at least talk two or three times a week and get together at times.
One particular day, James called me with a problem. It seems he had bet his cousin, Peter, on a football bowl and had lost the bet.
"So what", I said. "Pay up and count your losses".
"It's not that simple", he countered.
It seems that Peter lives up north and we are in Florida. The bet was for James to get paddled and since they lived so far apart, I was to do the paddling and video tape it to be sent to Peter.
"That's easy enough", I said.
"That's not the only thing", he paused then continued. "I have to have my pubes shaved completely on camera too."
"Right up my alley," I said.
"How many and with what," I asked, referring to thge paddling.
The bet had been to draw cards and multiply the number on the card by ten with Jack's being eleven, Queen's twelve and King's thirteen. As a bonus, extras would be added in accordance with the score spread at the end of the game. That part would be up to me.
Then he added, "The number is to be applied by each of a ruler, a paddle, your hand, a leather razor strop and a riding crop". All of which I had handy.
"Do you realize how many that can add up to," I asked.
"Yes, sir", James replied.
"If you draw a King, that could be one hundred-thirty times four. Hmmm, five hundred-twenty total," I whistled.
"Yes, sir. Plus the bonus", he replied.
"That many would have to be done in a couple sessions", I said.
"When are you free", I asked.
"Saturday", he answered.
"Be here at noon. No socks, no underwear and wearing your cutoffs," I ordered.
"When you get to the door, strip naked before you ring the bell", I told him.
I lived in a quiet neighborhood and the door was concealed, just barely, from the street but not entirely from my neighbors if they were on their front porch or happened to pull up into their driveway.
"Yes, sir," he said.
"For every minute you are early OR late I will add twenty-five strokes with MY choice of tools", I said.
I had him set his watch to the same time as mine and hung up.
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Saturday arrived and I had my toys laid out for use.
The doorbell rang and when I opened the door, he was standing there with his hands behind his back. His erection clearly showed his excitement and anticipation. His head bowed.
"Enter and show proper respect," I ordered.
James handed me the bag which held his clothes and entered, kneeling when he reached the center of the room. As I approached, he unzipped my fly and took out my hard organ. He glanced up at me waiting for my ok then swalled it all the way to it's base. I let him continue for a few minutes then led him into my dungeon where the cards were already on the table.
I reshuffled the cards, then turned to him and told him to cut the them.
"It's a Jack", I said. "Four hundred-forty".
"Before we do that, we have other business we need to take care of", I said as I rearranged the camcorder and picked up a moustach and beard trimmer.
I clipped off most of his pubic hair then finished with a safety razor. He stayed erect the whole time. (I hate shaving balls and ever since then he has to shave those himself before he gets to my house. I usually have all the guys shave either before they get there or I do it right after they arrive.)
I placed him over my knees with his head to my left and started with my hand.
"Forty-four with each to start with", I said as I delivered the first smack.
I continued the punishment with him standing up, bent over, grabbing his ankles, not letting him rub his rear until I was finished.
"Finish showing your respect", I ordered.
James knelt and swallowed my hard organ, licked my balls and generally serviced me until I was satisfied.
"We will finish next Saturday and your pubic area had better be as smooth as a baby's rear or your will get many extra", I said at last.
"Yes, sir", was the reply.
I let James get dressed and leave. His rear was glowing a bright red and a few lines had raisen on the surface.
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The next Saturday I finished with the hand, ruler, razor strop and crop. He had trouble standing still for the final swats with each of those.
"Now for the bonus", I said.
"There was a seventeen point spread so I am only going to multiply that by four. That males a total of fifty-one", I said as I picked up the ruler.
"Sir, I don't think I can take much more until another time", he said.
"I'm going to work on new territory", I said. "Stand up and turn around".
"Now hold your worm up, out of the way so I can work on your balls," I ordered. Actually James is well hung but a bit of humiliation never hurts.
James knew better than to even hesitate and did as told.
"If you even let go for a second, I will start all over", I cautioned.
I started hitting his balls with a steady rhythm, just hard enough to hurt. The longer I hit, using the same strength, the more painful it got for him. After completing twenty-five of the fifty-one, I ordered him to get his organ hard again which was almost immediately.
"Hands behind your back and don't move", I told him.
I stood to his left and struck his organ using the flat side of the ruler with a loud smack. He barely flenched but a hiss did escape his lips.
I continued until he was, once again, soft and I had reached fifty.
"Spread your legs wide apart and close your eyes for the last one. "Don't move until I say you can," I said.
James spread and then braced for what he knew was coming.
I swapped the ruler for a light, leather strap. I swung the strap from the side with a good bit of force hitting both his organ and balls causing a lot of pain. He jerked his hips back then immediately straightened up again. He started shifting from foot to foot.
"Be still or I'll start again," I said as I let him open his eyes. The eyes were watery.
I made him stand there for about ten minutes before letting him touch himself or his rear.
There have been many other such incidents over the years and he has more coming from a recent bet.
I am anticipating that!
If you want more like this, including spanking as well as organ punishment, let me know.
Master O Mastero@bellsouth. net Orlando FL