There I stood, dressed in my best school uniform, peering through a very small crack in the old timber fence. I could see the old man, sitting in a dirty looking armchair the upholstery well past its used by date, his trousers around his ankles looked like they were made of sack, he had underpants on which were thread-bare I could see his dirty flesh through the holes. He was inside an shed-like building attached to his house. I realise I was invading his privacy, but what the hell.
As I stooped watching him he removed his underpants with-out standing up, like he wriggled out of them, I was surprised he didn't wreck them while he was carrying out this manoeuvre. He had a short stubby cock, but it was erect and looked quite solid, I could only go by sizing my own as this was the first time I had ever seen another mans' erection. He was hard and wet, I saw the pre-cum drip on the end and he gently wiped it around the whole head, that was something I had just learnt. I was 14 and since learning how to handle myself to my delight, I was for-ever learning new tricks. But at the moment I was involved watching him slowly drawing the fore-skin back as far as it would go then bring the whole skin over the head, I must try this myself, I thought to myself. I wasn't an expert after discovering my manly tool some three years ago, but I did enjoy my quiet moments alone.
This was a once off, I had never seen this happen before. Not even my mates. You may well ask: why, or how come I was in this position any-way? The answer is I don't know. I heard movement and thought I would investigate. Ok, I'm glad I did, I wouldn't want to miss this for the world. He was breathing hard and fast, and dribbling into his beard, I was feeling myself through the cloth of my thin school-greys, the pockets were very big and I could play with-out any-one knowing what I was doing. My thought now was, is he going the whole way. Is he going to blow just I do? I suppose looking back it was obvious what was going to happen as it did with me almost every morning and most night times as well. I waited baited breath. He leaned his head back with his mouth wide open, and with a loud grunt his cock started to pulsate, throb, then a jet of white creamy cum jetted from it the first landed in his beard, then two more jets on his dirty white shirt, which was open enough to show his hairy chest. My cock throbbed at the same time pumping my young cum into my 'Y' fronts.
Then a familiar voice I heard first in the distance then almost in my ear. "Jackson." It was loud it took my by surprise. "What are you doing boy?"
Do I really need to answer, I have been caught and I know I have no real answer to any questions that may be asked. I did feel that I have been caught, sprung, hook, line and sinker. It was my History Master, Mr Dwayne, perhaps he had been watching and...... but for now he has caught me. Uncomfortably wet around the groin, I stood up, red and flushed. I was still breathless from my orgasm, and in the land of ecstasy.
"Sir, I was...."
No I can't say any-thing, it was obvious to what I was doing. He caught me now he gets the prize. Was he going to take me back to school to the HeadMaster and get me punished?
No, we went off to his house which wasn't far from the incident.
"You know I am going to give you the cane." He said with almost a smile of delight on his face. "This is the most deplorable incident I have ever witnessed, I should take you to the Head Masters office and watch him give you a proper caning, but I will save you from the embarrassment."
I was NOT going to get a 'proper' caning I tried to assure myself. We got to his house and I was pushed inside. Into a study, with the usual furniture, desk, book-cases high to the ceiling, and a high-back chair, on the desk lay in full view of any unsuspecting teenager was the cane, it was a stock standard school model. My heart leapt out of my chest, I had been caned at school and now I am going to have a 'private lesson'. An improper caning? No less!
The order was given, "Remove your clothes, everything."
As a good obedient young lad I did as required. My underpants almost stuck to my skin as the 'good stuff had set, stuck fast, I removed them last.
"Bend over the chair, and stay there until I tell you to move, as at school you will wait until you are told. Then I want to see your hands go straight to your neck and interlock them. Is that clear, Jackson?"
"Yes, Sir." I said as I moved to the chair and bent over, my legs straight I was on tip-toe, my hands gripping tightly the bottom rung of the chair leg. This wasn't a very comfortable position. The back of the chair cut deeply into my pelvic bone. I could feel a winter draught coming from somewhere and breezing between my buttocks, which were still hot and sweaty from my orgasm. I heard the sound of a cane being chosen, the rattle of the bamboos against each other. Then the test 'swish' for the decider. My buttocks clenched with anticipation with this sound, the history master must have been watching me closely, he 'swished' a couple more canes.
"Six I think will satisfy your needs this afternoon, perhaps another dose in a week on two, it has not gone un-noticed that you are going to enjoy these next few minutes, but we will see, now, relax those buttocks. As you know I only cane relaxed buttocks, but, my waiting equals your extra pain as I will increase the strength of the stroke as to the waiting time."
I don't think I have taken all what was said in, he talk too much too quickly, but I think I might have the jest of it. If I take my caning as a school-boy would I have no worries. All I have to remember is after the stroke and the squeeze of buttocks, relax for the next onslaught of pain.
He put the cane back down and came over to me, he squeezed each of my buttocks testing the resilience, I distinctly felt his thumbs gently caress my inner sanctum. He followed through running his fingers through the pubescence to my balls. This, at my age, made me jump forward a little. It wasn't long after I felt the cane touch my cheeks. The swish finally came and set my bottom on fire.
My Best friend and I had tried spanking especially the cane while his parents were out, but this caning, which I was to suffer was nothing but agony compared to Colin's feeble strokes.
Mr Dwayne, waited for my relaxed buttocks before proceeding. I received all 6 strokes with only a couple of minor incidences, but I managed to evade any extra strokes or extra hard strokes. Luck was with me. He told me to stay in position while he got a pot of cream. I was dying to get up and flex my buttocks, Mr Dwayne came back to the room carrying a jar of cream, also he had a bottle of something I didn't know what it was, he washed both my cheeks with this solution and it stung. It must have been methylated spirit or something, then he massaged the cream in, that was very nice.
Eventually I was allowed the stand up.
"You will report to me on Friday night in a fortnights time at 4.30pm straight after school is out."
My bottom was looking forward to that.