Whoopee!!!! I'm 18, got my own wheels, I'm free. Dressed in my full school uniform I'm driving into the rising sun towards Brighton where I have made a date with a mature gentleman whom is rather partial to boys in uniform especially school attire.
I met this very likeable man in the pub in Brighton the previous Saturday night. He took me to an empty table and talked for an hour or more until my mates, who I was with, dragged me off to another pub. We were in the swing of a 'pub crawl' from one end of Brighton to the other. I was very interested in speaking to my new acquired friend without being interrupted. He was like a walking book of knowledge and I really respected this old man, he was easily well into his 60's. He also treated me with a lot of respect considering my obvious youthfulness.
I had a reasonably long journey ahead of me and with an almost empty petrol tank so I stopped at the next service station and filled up.
There was a young traveller going the same way as I was, so I offered him a lift. He gratefully accepted and we were soon on the road again, I gave him a bit of a 'third degree' but without giving away too much of this weekends intentions, I shifted from this subject as I could see it wasn't his scene and we chatted about other things. Pop music and girls and things like that. I dropped my young friend just before we got to Brighton, and wished him a pleasant journey.
I was soon on my way to a future, which lasted a good few years. The Headmaster, which he told me to call him, had a very close interest in naked boys, particularly their bottoms, I fell well within this category. As I said before although I was 18, I easily could get by as a 16 year old, by cutting my pubic hair as to make it look as a though they were just growing. I would put the mannerisms of a boy and also pretend I was only 14 years old.
At last the pub where we were meeting was insight, but I couldn't get a parking bay, not a space, even for my mini. I travelled around several times but nobody was moving, by now I was getting very nervous as the time of the appointment was upon me. I don't want to be late, where am I to park?. It was quite a distance from the pub to where I had seen a spot, must go back and hope it is still vacant. Lucky me, it was, but I will still be late for my meeting, I do hope my friend isn't too pedantic with keeping time,
I was just a couple of minutes late. When he saw me, he looked at his watch I know from passed experiences what meant, and at that moment I was at the mercy of my headmaster. I relish this idea, not that I like to depend solely on other people, but under these circumstances I rather like to be 'mothered' O.K. 'dominated'. On this occasion, the visit to the Headmaster was because I'd been disrespectful to the arts master. The scenario I was told to act by. We would be like actors on the stage, my words and actions fit nicely in with what the headmaster is doing or saying. I was good at that. We had a quick drink and left, I think he was eager to get my bottom under his total command. I followed his very fast car, and thought I had lost him at one stage, which would have left me embarrassed as I had no idea where to go. We got to his house, drove into a double garage he locked the door with a remote and was soon on my way to the punishment room as soon as we were inside he locked and chained the front door.
He said, "As a precaution, just incase my nosy neighbour decides they wanted a 'cup of sugar'. Which they were known to do".
We got straight into the session, "I will leave you to think over your behaviour, and return in five minutes for your reply to the reason you have treated the arts master with so much contempt".
The voice of authority had spoken, I will remain under this spell until 'dismissed' at the end of the session. On his return I was questioned again and told my punishment was to be six strokes, and then he sat back on his armchair, with the cane he played flexing and bending it to prove how flexible it was. Waving it around he told me to strip to my 'birthday suit',
I was determined to take my time, so slowly I removed my blazer followed by my tie and shirt. I bent down without bending my knees to untie my shoelaces giving my master something I knew he would like. I next removed my school greys and socks and stood clad only in my underpants, I stood and waited, he nodded with a sort of a smile, again I bent down, as I did I removed my 'Y' fronts and stood waiting for the next order.
"You ARE a very disobedient child, How old are you"? He growled.
"14 sir," I answered just glancing in his direction quickly.
"What was my order to you," he snapped.
"To strip to my birthday suit, sir," I replied having the feeling I was in the wrong, but where? I was sifting through my mind so quickly I was almost dizzy.
"You must have broken all records, if you were born with a wrist-watch on". He gave a smile again as much as to say 'I got you over a barrel'.
I removed my watch and placed it in my trouser pocket.
"For your incessant disobedience I will give you two extra hard strokes within the six, as six is the maximum I'll award per session, we don't want your bottom to be too badly swollen or it will leave too long between sessions."
"I want you completely stretched across the back of that chair, legs straight and 150mm (6") apart. Your hands gripping the seat".
I did as I was told, he moved me to several different positions before he was happy with his target. Next something I didn't expect he anointed me with a dollop of cold cream, which he worked well into my awaiting flesh, when I say 'well' he worked it between my buttocks titillating me as he fingers fondled my glory hole. Between my legs rubbing lots of cream around the back of my ball sac, I was ready. So was he. He drew back and held the cane against my flesh, he whipped it back and forward again like a violinist then without another sound flicked the cane across my cheeks.
I heard the swish and a thwack as it came into contact with my young and tender flesh. Later I felt this first cut was a 'sighter', because although it was reasonably hard at the time, after the next couple of strokes this one was the softest. I gauged each stroke in my mind, decided number four and five would have been the hardest for this session. I was right. After the six strokes had been applied I waited to be dismissed, Sir spent quite a long while inspecting his handiwork running his fingers across the welts to the amusement of my painful plight, and eventually he stopped and stood aside.
"You have taken your punishment very well, like a true scholar you may now rise". He said still flicking the cane as if IT wanted to give me more.
I stood up with my head still downcast I thanked my master for punishing me. He replied "This session will not be repeated, and my behaviour must improved especially towards the other masters".
My only answer to that was, Sorry Sir, I will control myself better in future. Thank you Sir for the punishment"
"Put this gown on", he said, handing me a white silk dressing-gown, "You will be required to show me the marks whenever I ask in the next few hours".
We had a few drinks over the next couple of hours and talked, every now and then he would put me across his knee only to check on how the marks are looking.
I asked him. "Sir, does my hard cock worried you"? I was hoping for sex.
He replied. "It doesn't worry me, but it looks as though it worries you. I am not interested in sex".
"Bend over the chair again, I will see to your hard cock, but this won't happen every time".
He put his hand around my cock and moving the for-skin forward and back again it felt good, I was breathing fast. I didn't last long only a few strokes and I was throbbing.
I cleaned the floor and myself and asked. "Can I do anything for Sir".
He answered. "No".
We did sleep together, naked, that night and I did feel him hard a couple of times in the night. I stayed for the weekend but only had the cane once more just before I left to go home. He said it was 'just a reminder' until the next session.
He asked me. "Do you mind if a couple of local School Masters come to witness the next session, I would expect you to receive the cane from at least one stroke to be given by each of them. And I know they will give you a good time".
I said. "Sir, I would love to be a school boy with several Masters". "I will be in touch".
Which was a promise I kept. I went home a very happy boy and of course straight to the mirror.
I telephoned Sir about three weeks later. But he was going to a retired teacher's convention. So I made a date for the following weekend, he told me he had two retired teachers coming to my next session, and to make sure their was no marks on my bottom as he will not cane me across other punishers handiwork.
I assured him he was my one and only master, at this moment, and I will wait for his session.
Anticipation was great, just like school days when you were to receive the cane and had to wait a few days to a week before the event.
I did see an older guy at that weekend only for sex. Although he said he was interested in seeing the cane dealt out to naughty boys.
I told him about the session while he went down on my cock. He removed his teeth, and sucked me brilliantly, I had been with this guy before and his gums enshrouded the head of my cock as if it was made for it. The warmth of his mouth and the ideas going through my head sent me in dizzy circles. It was magic, he drank every drop.
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