There I was standing again in the Headmasters office. I would come here about once a month to keep myself in tune. 18 in two week's time and I will be able to graduate.
I stood quite a distant from the chair I knew so well, I'd being visiting since I left school when I was 15, the Headmaster knew exactly what I needed.
"Over to the chair, Jackson, and lean over, stretch yourself until you can put your hands through the leather loops, and grasp them tightly, we don't want too much movement do we?"
The voice of authority. Which set the scene.
The boys from the school where on holidays, so we were not going to be disturbed.
I bent across the back of the chair, stretching on to tiptoe.
I was only a little lad my appearance of a 14-year-old. It was all too easy. With a slim 18 inch (45.6cm) waist, and a height of about 5' 1" (15.5cm). My 7 stone ( 45Kg) frame made me a wanted boy for discipline. My buttocks nicely round through riding my bike. I was a prime target for the cane, and I could take a really heavy caning which was what the Masters wanted. (Sorry all you Masters of the 60s who missed out on me. I assure you I didn't miss out).
I was on balanced over the back of the chair barely reaching the strap holders on one side and the ground with my toes on the other.
"Lets see, I applied six strokes last time you were sent to me, I think we will use this as a standard from now on". He took a deep breath and continued. "Plus extras".
I had to agree with him in my best soprano voice.
He pulled my shirt out of my trousers, and smoothed the fabric, with a little squeeze to each buttock in turn.
"You will feel the benefit of the caning before I have finished, but, you will still stay in position come-what-may." He said, tapping the cane on my bottom.
With that I heard a loud swish followed by a very loud crack, then the most excruciating pain starting from my bottom and working right through my body.
I gasped, this caning will hurt, it is meant to.
After the second stroke, I felt a little bit better, as my mind was now getting used of the stinging pain I was being treated to. Still I made it known I was in agony. This was part of the scene.
The Head-Master said, "I don't think you felt those two strokes so I am going to make sure with the next two strokes you will reap the benefit, thus, ensuring we both enjoy the meeting."
With that he told me to lift my stomach off the chair. He proceeded to undo the top button of my trousers and unzip them. He then lifted the material away from my now hard cock and guided them down to my ankles. Again he smoothed the fabric of my 'Y' Fronts, playing with the waistband and massaging both buttocks.
After the usual few taps I heard the wind whistle as the cane cut the air and the loud crack as it landed across my 'Y'Fronts, I screamed out aloud to make sure he knew the pain I was suffering. He then massaged my still stinging flesh, something in the unwritten rules of the schoolboy, he would never be allowed to do himself. In the school I went to, anyhow.
The fourth stroke, again had me scream out, I was suffering alright.
He laid the cane on the desk, I thought he might have finished with me, I was just getting to enjoy it. Instead he leant down behind me and lifted my underpants over my swollen cock, and down to the ankles they went.
I could feel his hot breath between my legs. He stood up and after massaging my buttocks again, he went to the medical cabinet and got a jar of cream which he applied some on my bruised rear. Massaging it well into the flesh, it felt wonderful.
The cane was applied again with two very hard strokes, and massaging between.
This session in real time at school would probably have taken about five minutes at the very most, but, it was well over half an hour I had been bent over for.
My head was spinning from the position I was in, so, I would have been very glad to have been told to stand up. Not the case.
"As you have marks on one buttock only I am going to give you three more strokes, to the left buttock so it doesn't feel left out."
I knew he was an expert on his target, or should I say my target.
"I am going to make them quick so you won't have time to breathe in between."
I braced my mind to accept these next three strokes.
Each stroke was harder then the previous one and very well placed, and I did have enough time to enjoy each stroke before the next one was delivered. I was crying out aloud by the second and the third I had tears running down my face, they were hard.
If anyone has had the cane across one buttock only, you would know exactly how I felt. As there is no 'buffing' effect, as with across both buttocks the cane lands directly on the nearest cheek thus, digging deeply into the dividing crack which almost welts the anus itself.
As it turned out the massaging which happened directly afterwards, sent my cock into spasms, ejaculating streams of sperm down into a little stainless steel bowl on the ground.
"That made you feel better, and if you stay there for one moment I'll get a cloth and rinse you off."
I stayed in position, the warm cloth felt good although I was a little embarrassed, having someone else clean me up.
I had a month to wait for the next meeting with this Head Master.
From the bottom of my heart......To the heart of my bottom