In late October while my parents were in Las Verges. I was very horny and talking on casual encounters, once again. While I was looking for a dominate lady to talk to, However by fluke I found a man. He told me that he like to dominate young boys. Allan told me that he liked to role play and punish his young boys. He told me that there would be no _s_e_x_ involved, just the pleasure of punishment. I agreed to call him that night. late that night I called Allan. We talked about ourselves. He asked me to tell him about a experience that I had with being spanked. I read him my spanking chart and told him all he wanted to know about all my spanking and _s_e_x_ual fantasies. We talked about role play. Many suggestions were talked about including coach hockey player, scout scout leader, and teacher student. We finally went with teacher student. He told me that he was a retired teacher and principal from a all boys boarding school north of Toronto. He told be a list of names of students he paddled and strapped in his office at school. He didn't like that school board got rid of punishing students. One of his students named Randall now about forty still visited him once a month for old fashion school discipline.

When the day came I packed up my bag of tricks, consisting of my spanking paddle, a small ping pong paddle and different pairs of pyjamas. Allan had asked me to cum over to his home about eight o'clock dressed in black pants, a white shirt and a black tie. I must have smoked a pack of smokes on the way there I was so nervous, but excited. When I pulled into his driveway he was waiting for me at the door. I slowly walked up to his door. He took my coat and bag and put them down on the floor. I bent down to untie my shoes and he made a comment about how nice it was going to be spank my young boy bottom. We went into his living room and sat down to talk and get to know each other better. He did most of the talking. He told me I could have a smoke if I wanted to, so I had five. Finally I got relaxed and started to answer his question with more then one word. We talked about the spanking chart that I had read him. I opened my bag and gave him a copy. He read it and asked me about ten questions about all of them. I was feeling rock hard remembering the experiences I had years ago. One thing turned to another and he moved and sat be side me. He asked to see my paddle. I showed it to him and he liked it a lot.

We talked about the role play. He wanted me to pretend that I was one of his students in class. I was to write an essay about being spanked and how I felt as every smack hit my backside. He was going to mark it and if I passed with correct spelling and grammar I could go to a dance that night. But if I failed I was to be sent to the headmasters office to be paddled. After I was punish I was to go back to my room and change for bed; put on my pyjamas, and rewrite my easy. So I agreed and we went down into his basement. He had set up a classroom setting with a black board and desks. The black board read "The _s_e_x_ual Feelings of Being Spanked Eassy". I sat down at my desk and started to write. I wrote for about twenty minutes. My eassy was making me feel very excited in my crouch. I made the mistake of losing my tie and undoing the top button of my shirt. Allan walked over to me grabbed me by the arm. "you know your not to remove your tie in class" "I didn't know" I said. "It's you fault for not knowing the rules, Now off to the Headmaster office for proper guidance" I smiled and looked at Allan who also smiled. We walked to the back part of his basement past his workshop to a room marked Headmasters office. We walked through the door and he told me to sit down on a hard wooden bench just inside the door. Allan walked through another door and was gone for about five minutes. I assumed that I was going to be punished for losing my tie. I wanted it bad and hard so I took off my tie and put it in my pocket. Allan walked out just as I was standing up and looking the other way. "You will be punished for standing up as well. When I turned around, wishing that I had left my tie on now. He was not impressed. I walked through the door and saw the office, it was like something out of Dead Poets. I was feeling scarred I was brought in and told to sit down on a chair in front of his desk. Allan went behind the desk and started talking about the rules of the school, and that I was never going to forget them after this, I smiled. This is not a laughing matter Shawn you need to be punished. "So tonight you will not be going to the dance and you will stay in your room and write out all fifty school rules fifty time each.". However you must be punished for standing up and taking off your tie. "Assume the position." I guessed that I was going to be spanked so I stood up and walked over beside him. I bent over his knee. He opened his drawer and took out a big wooden paddle with holes in it. I was so excited, yet I was not ready when the first smack hit my backside. Then I settled in and enjoyed my self. I was paddled fifty time One of all the rules the school. I stood up and Allan grabbed my belt and undid it and pulled down my fly, then my pants and underwear. Then he stood up and I was told to Bend over and grab my ankles. I did and, then was spanked with my paddle. Another fifty whacks a little softer and after every one Allan rubbed the paddle on my bottom.

When he Finnished the Role play ended for a few minutes. He asked if I was Okay. I was and then I pulled up my pants and asked were my room was to complete my punishment. Allan handed me my bag and walked me to my room. It was right beside the classroom. Inside were two small desks, two wooden beds and a bathroom with a dresser. Allan handed me a pad of paper with the rules on it and blank paper and a pen to write out my rules. I was told that my room mate was at the dance tonight, and reminded to change for bed. When the door closed I ripped off my clothing and put on my pyjamas. I sat at the desk and read the rules. They were not rules but was the next part of the role play it said that I was going to be punished by the Headmaster again. I sat waiting for Allan to come back. I sat at the desk and starting to jerk off. Just then the door opened. Allan asked what I was doing I didn't answer. He looked down at the blank paper and then back to me pulling on myself. I was told to stand up I was forced to bend over the bed. Allan spanked my bottom another fifty time with his hand. I know it was fifty again because I must count out when I am spanked. When fifty was down I quickly grabbed my self again. Allan sat in the middle of the bed. I was told to lye across his lap. I did and he pulled my pyjamas off. I was spanked another fifty times with my paddle and his hand. When we reached two hundred I was done.

We went up stairs for a talk. I had a smoker or three. and we talked about the game we had just played. I was feeling sore but great. We talked for a while it was late and I should have left. But we went back down stairs to the bedroom so I could get dressed. Allan told me I could jerk off if I wanted to, I wanted too! I pumped myself so hard a sot a big hot creamy load all over my chest and arm. Allan passed me his paddle he told me to wipe my cream on it, I did he then passed me a towel I cleaned up and he told me about Randall. Who was married and had two boys. His oldest boy was thirteen and was always calling Allan to see if he could get spanked. Randall's son John has noticed the Headmasters office and spanking paddles in the top drawer on a family vist to Uncle Allan's House. Allan told him he would love to spank him for being a naughty boy, but he had to wait until he was eighteen to be spanked. His father Randall can't spank the boys Allan told me, because he gets a hard on. I was sitting there in my underwear, just about to put on my pyjamas (I was going to wear them home), Allan yelled stop! " I would like to spank you again on your underwear.! I stood up and stood against the wall I was spanked another fifty times and it felt good. I was hard again. When I left I told Allan I would be back. And I was and not alone, but that's another story.