Disclaimer: Two young men in this story are 18year old. And are to receive the cane.
Two Boys with their Pants Down
I had put myself forward to a 'practical Punishment Session'. These were words spoken from my school form Master. He wanted two year twelve boys because we were both eighteen or approaching that age.
Built like a willow tree, I didn't think I would pass the first test stage, although I harboured a good looking well proportioned backside in my tight school grey trousers I always wear. It was part of the uniform, with black polished shoes, grey or white shirt, blue and gold striped tie, of course grey cap and black blazer with the school badge embroidered on it.
The day came when I was given the address to attend 'class'. I thought I would be the only boy but another boy was waiting at the door when I arrived. The Master let us in and showed us straight to the room which was decorated just like a real class.
"I will be back in 5 minutes, and hope for your sakes you are ready for me."
We both were bewildered. What did he want us to do?
We found out soon enough, because when he returned he was furious.
"Why are you two not ready for me?" He roared.
Of course we didn't know what was wanted of us.
"You will both be getting six strokes of the cane for disobedience."
I went to say something, but was stopped.
"Mr Jackson, if you say anything else I will increase your punishment by two strokes. You will both go over to the armchair in the corner and strip right off, bare, naked, birthday suit. Call it what you will, but, I want you without a stitch of clothing, jewellery, false teeth, arms or legs. I love to use the cane and I will find any conceivable excuse to practice my art."
The lecture was over, we were naked, both of us sporting semi-erections, which was a normal practice in the showers etc, or nakedness.
"Turn around I want to see your bottoms so I can decide which cane to use and how hard to give it to you."
He came up behind us and we were told to bend down and touch our toes, he then gave my cheeks a squeeze, quite hard, then the other boy.
"Mr Worthington, you skin is not up to getting very hard strokes, although I will attempt to give you as hard as I dare, I shall watch very carefully, I don't want to break the skin, but I do think a very hard caning would do you good."
"You first Mr Jackson, bent over the chair in the centre of the room, you will NOT move until I tell you and then you will stand up with your hands interlocked behind your head, and at no time will you touch your buttocks. Have I made myself clear? Ask any questions now."
Without speaking I walked over to the chair, it was a wooden upright chair from some medieval classroom, probably King Arthur or Henry the eighth. The back was shiny and polished. In the bending position I could easily reach the bottom bar or rung which holds the legs apart. Not good enough. Hold tight he warned and he wound a handle at the side which moved the back of the chair upwards. I was stretching to a very uncomfortable tip-toe position. My legs now stretched as I felt for the ground with my toes. Mr Trusscott stood back as an artist does, then another squeeze to the buttocks he was very happy with his positioning.
"Nice, I am going to enjoy beating your buttocks, and I think by the looks of you, your buttocks are going to enjoy being beaten." "Mr Worthington, I would remove the smile from your face and interlock your hands as suggested by me."
He chose a cane from the rack on the wall in-front of me. Giving each one a swish until he chose the right one. It looked to me like a medium size comparing it with the other canes hung up. Standing just to the right of me he touched my buttocks with the cane and took up his stance. With a quick swish and a crack the cane cut its first welt across my buttocks. I yelped more in surprise, it obviously was a good choice of cane and a good cut, because the sound of it cracking against my skin increased my excitement and I'm sure his excitement too. It seemed like about five minutes before the next stroke, but it wasn't, the sting was wearing off and giving me a nice after stroke glow. The next stroke was the same followed by a third, all increased in volley, all felt like they were on the same spot. My increase of voice increasing to a very loud gasp. I want him to know how much it was hurting me.
"Stand up and over to where Mr Worthington is and you Mr Worthington will adopt the position over the chair." "Luckily for you, sonny, I don't need to jack up the chair back."
Mr Trusscott made his move first testing the canes again, and squeezing the boys buttocks. My own cock was leaking embarrassingly, but I could do nothing about it. He had made his choice, it was a slimmer cane then the cane, he used on me, 'my cane' was put on a side cupboard, so I could see it, I suppose 'ready for next time'.
The start of Worthington's session was a very hard stroke, almost sending him lurching forward.
"Compose yourself, Mr Worthington, I warn you will get another stroke if you continue getting out of position, your last 'free' warning."
Two strokes later, and eyes full of tears, he was told to rise and stand next to me.
I walked forward and took my stance, bending over the chair. Again the cane kissed my buttocks three times, each increasing in heaviness, my bottom was begging to be released from the pain, but at the same time wishing it to be harder.
Worthington received the same treatment, he buttocks looked like Clapham Junction, but with purple train-lines. He couldn't help holding back the tears. I was brave and determine not to show my emotions, perhaps that was a bad thing. After, we were stood there waiting while Mr Trusscott, left the room, probably for a 'fag' we had a quick inspection of each others buttocks, in which we run our fingers over, just to see it the marks were real. "Mr Jackson, I want you over the chair, but this time with a difference, stand back with your feet flat on the floor. Your arms over the back on to the seat."
My manhood was solid and pointing straight towards the chair.
"Now, young Mr Worthington, you will sit on the ground between the chair and Mr Jackson, facing him."
I know what was to happen now.
"Take Mr Jackson's penis into your mouth, and enjoy. Mr Jackson give me an indication when you are about to orgasm. It will be worth it. The other rule is to orgasm before the sixth stroke is awarded. Do you think you can manage it?"
"Yes, Sir." I happily Said.
As Worthington gently sucked and fondled I felt the full stroke of the cane, it was about the fourth stroke I thrusted forward at the same time, telling Mr Trusscott I was cuming. He gave me two extra heavy strokes, not that they registered in my brain as I was busy having other things happening. Soon my cock and ball-bag was completely empty. Exhausted I rose from the chair in an up-right position, Worthington still latched on to me and gently sucking what remained in the canal, the scrapings from the lining of my ball-bag. I felt wonderful, relieved, it was one of the best orgasms I had ever had. I swapped places with Worthington. And sitting in this position I could only have the head of his cock in my mouth, but it was great, I tongued it round and round tasting the pre-cum which was coming more and more as I sucked. I fondled his balls just like you would if you were stroking the head of a kitten. I felt him thrusting gently against my chin, I could feel the tube between his anal and balls was expending, I knew it wouldn't be too long before I had a mouth full of little Worthington's swimming down my throat. At last, I think he only had two strokes before he panted out that he was cuming. I lapped every last drop, holding on like he did with me. He got the full six and was quick to rise after and let me have the full length down my throat. I squeezed his cock like a tube of toothpaste to get every skerrick out.
"Go a get a shower boys." Mr Trusscott said. "There's room for both of you at once."
"Are you going to join us, Sir?"
"If you are cheeky again I'll give you another dose of my highly effective medicine."
I knew I couldn't have gone for any-more today. We had a wonderful hot shower, playing with each other while we were washing. Mr Trusscott walked in on us and told us. "You will report to my office in two weeks time for lesson in safety in the shower. This time you will know the procedure. I have something else in mind to enhance your pleasure."
We got dressed and left, going to Worthington's house as his parents were out and no-body to disturb us, we knew we would be right for a couple of hours, to get to know each other better. And to apply soothing cream to each others bottoms.
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