I was a boarder at prep school in England (boys aged 8-13) in the 1960s. This is a somewhat compressed version of the spanking relationship I had with a boy two years younger than me. To protect the innocent (and not so innocent) some details have been changed.
At the age of 12, I was made a sub-prefect at my Prep School, Warwick House. This position granted me great power over the other boys at the school. It was the 1960s and corporal punishment still existed at the school.
With my new powers as a sub-prefect, I had the perfect opportunity to get closer to the boy who most attracted me, Simon Mills, a tow headed athletic third year who seemed very conscious of his good looks with a reputation as the naughtiest boy in the school. The sub-prefect role meant that I was entrusted to look after a class room of boys at the end of morning and afternoon break.
I asked Raneleigh, the Head Prefect, how classes were allocated to prefects. It seemed there seemed to be no system of allocation other than to ask. I immediately opted for class 3b, Simon Millss class. Simon was actually a likeable boy but very capable of disruptive behaviour, shouting, teasing other boys, throwing things. Simons reputation as the naughtiest boy in the school was soon proved to me.
Simons other crime was to under perform in the classroom. Because of his disruptive behaviour, he was often sent out of class and that made his marks poor. Because of this, Simon was frequently put on weekly reports, which meant having each lesson signed off by the teacher in charge.
Being on report was something only a handful of boys would be on at any time. Every boy started with a clean sheet at the beginning of term but very soon Simon, Karl and maybe one or two other boys would find themselves on report. At the end of the week, on Friday morning break, the boys on report had to show their reports to the headmaster. If the Headmaster wasnt satisfied, the boy remained on report and sometimes found himself ordered to report to the study later on, which meant he was going to get the slipper or cane.
The key to avoiding weekly reports and the almost inevitable chastisements that followed was not to get on report in the first place. Simon Mills tried hard to be good at the beginning of each term but in the end his natural talent for disruption and mischief soon got the better of him.
I came into 3bs classroom after games one afternoon early in the term. Even as I approached, I could hear a commotion and there, at the centre of it was Simon Mills, flicking ink pellets at the rather dim Baines, who was in the process of making his ink pellets to flick back. Ink pellet flicking was a big crime at Carn House because of the mess it made of the classroom and the boys. I stopped Baines in time so there was no more punishment for him but Simon was caught red handed. Later on in the term, that offence alone would have earned him an instant caning had I reported it but because the term was still less than a week old, he might just end up on report. Having silenced the class, I took Simon outside the class door and shut it.
"You know I should report you to Mr Crook dont you?"
"Yes Gould, sorry, I wont do it again."
"That still wont stop me reporting you, I cant let you flick pellets without doing something. I am going to write your name on the board."
"Please Gould, its the beginning of term, I dont want to go onto report."
I was sure that Simon realised that I liked him and might be lenient if he pleaded with me. I decided to let him go. Just this once.
"Well, okay, just this one time, but dont think you can get away with this sort of behaviour again."
"Yes, Gould, I promise."
We went back into the classroom and I told Simon to sit down which he did with a very cheeky grin on his face, he had pulled one over on the new sub prefect and I had let the class clown make a fool of me.
One of the privileges of being a sub-prefect was the opportunity to watch the boys change for PE. When I had changed for PE in the gym, the prefects normally made themselves scarce, within ear shot but not watching the boys change. With 3b, I stayed in the changing room and set out to watch the nine and 10 year old boys as Simon Mills changed. The PE lesson I supervised them changing for was on Friday after break. Simon took the peg conveniently beside the door to the gym itself. Trying to remain inconspicuous I bounced a baseball on the floor as the boys changed. Simon stripped down to his very brief light blue underpants and then put on his shirt and socks before removing his pants. He hesitated a bit as to whether to face me or to face the rest of his class choosing the latter, as he removed his pants giving me a good view of his bottom which bore the unmistakeable imprint of the headmasters slipper. Both cheeks were pink with darker cherry red to blue blotches at the apex. On the right cheek there were two distinct red crescent moon shaped marks outlining the spot where two hard swats from the slipper had landed.
The other boys were making a lot of noise chatting away so I approached Simon as he pulled his PE shorts on.
"I see you got the slipper this morning."
Simons eyes were a little red on closer inspection. He was a bit embarrassed by my remark.
"You wont tell anyone will you?"
I was surprised by his bashfulness about being slippered. He had been called out of assembly that morning for losing his games kit again and had presumably been slippered straight away before the first lesson. I was, I realised very aroused by the sight of the 10 year olds slippered bottom and wanted to know more about it. But this would have to wait and besides, I wanted Simon to owe me favours to be called in later.
"No of course I wont."
"I am going on report again as well, I am always on report."
"Oh sorry about that, well we will try to see that nothing happens when I am in charge wont we?"
I had sown the seed of a plan that was beginning to formulate in my mind.
Simon was soon in hot water with me again. I had worked out that I could catch him if I delayed my arrival; he had little ability to sit still with getting up to some mischief. Sure enough, a few days later, I hovered quietly outside the class and heard the noise go up sharply. I opened the door swiftly to see Simon throw a paper plane. It crashed against the black board as I shut the door. I had caught Simon red handed in a reportable offence. Simon looked glum, he knew his fate. Instead I called him over to the door, told the others to keep quiet and took him outside.
"You are on report arent you?"
"Yes Gould, oh please dont report me. Ive had the slipper twice this term already."
If I reported him, he was certain to get punished on Friday.
"What will happen this time do you think if you are reported?"
"Ill have the cane, thats what the head said. The next time I did anything wrong he would give me the cane."
"If I dont put your name up, the other boys will think I am being soft on you."
"Oh please Gould. You dont want me to be caned do you?"
Truthfully, the idea of Simon being caned was quite an attractive one, I realised. The idea that had been forming in my mind over the last week or so began to crystallise.
"I will put you name up on the board, but will rub it out just before Mr Crook enters, on one condition."
"What do I have to do?"
"You are to come with me to your dormitory after lunch today, I will let you know more at lunchtime."
We went back into the classroom and I put Simons name up on the board and rubbed it out just as Mr Crook entered.
In the end, I opted for a simple plan. I would use my freedom as a sub-prefect to call Simon out of his after lunch reading period to see the Headmaster. The prefect in charge, was unlikely to question this.
At lunch, I told Mills my plan. About two minutes after the reading period began. I excused myself from the sixth form.
"I have to help Mr Roach with the cricket kit." I announced to the other boys.
No one was interested, so I walked out, unchallenged and went directly to class 3b where Simon was waiting expectantly, sat on a locker, a Tintin book in hand.
"Mills has to report to the Headmaster."
All the other boys looked at Mills sympathetically, a summons to the Head normally meant just one thing, a beating.
Mills hopped off the lockers and then obediently followed me out of his classroom and up the stairs to the dormitories at the top, out of bound to boys at this hour of the day. Nevertheless, I checked on each landing as we passed that no one else was about. We went upstairs to his dormitory on the top floor. Simon did not seem unduly surprised but he was nervous.
"You understand that I have let you off having the cane, in return, I am going to punish you instead, we will use your slipper, agreed?"
Simon looked at me. He knew he was trapped. He hesitated for a second or two and weighed up the options. He could go along with me, or he could choose to be caned by the Headmaster. There really wasnt any choice. He opted for my punishment.
"Okay, wheres your slipper."
Simons voice was husky with trepidation. He reached under a bed at the end and handed me a slipper with a very light foam base. I had no way of knowing whether it was really his or not but it would have to do even though I doubted it would be effective on a boy used to being punished with a size 12 leather soled slipper. There was one way I could make it more effective. I sat on what I assumed was his bed.
"Alright then, take your shorts and pants down and put yourself across my lap. I am going to use my hand, like Matron does."
Matron occasionally spanked boys in the junior dormitories, Simon would know all about it I am sure. On the grounds that he wanted to get this over with, Simon hesitated no longer and after a short pause, undid the snake belt on his shorts, undid the shorts and let the drop to his knees and then pulled his pants right down as well before putting himself across my knee even hitching his shirt up at the last minute so that his bottom was fully bared.
His head rested in his arms on the bedspread, as did his feet. His weight still pressed down on me. For dramatic effect, I pulled his shirt right up to his shoulders and then pushed his shorts and pants down to his ankles.
"Ready?"
"Ready." Came the muffled reply.
"I am going to give you 20 smacks, understood?"
Simon nodded his reply and tensed his bottom, the middle part of his body white from having worn swimming trunks on holiday. I smacked his bottom lightly, my hand bounced off, his cheeks quivered, Simon made no response. I smacked him several times more, still no response. I regretted saying how many smacks I was going to give him. I decided that I would have to spank him much harder.
"Those were just warm up smacks. This is the proper punishment."
"Oh Gould you promised."
"I can report you instead if you like."
"No get on and get it over with."
I smacked him much harder, the smacks echoed around the dormitory. Simon lay passively, letting me spank him with all my force, his bottom quivering each time I spanked it and now definitely beginning to pinken. Simon was beginning to get restless, he gathered the bedspread around his face to muffle his gasps of pain, his right hand came up to protect his bottom and he twisted on to his side to try and avoid the blows, kicking his shorts and pants off.
"Get back down and stay down. Theres four more smacks to go."
I administered the four smacks, with extra firmness. He grunted with each swat.
"I am going to give you another 10 for moving. Stay down."
For a moment, I thought he was going to refuse, his body twisting to get up, the sting beginning to peak. I didnt start straight away but waited until Simon had completely settled again. This time his hands were outspread holding onto the bedspread. Each smack rang around the dormitory, Simon tried hard to keep quiet but he was making a lot of noise by the end of the extra 10 smacks.
Spanking over, Simon remained over my lap recovering for a few moments. I inspected my handiwork, an unmistakeably well spanked bottom, well reddened with my finger prints visible on his right flank and thigh. My hand was pretty sore so I am sure Simons bottom hurt.
Simon recovered his composure. Stiffly he rose and knelt on the rumpled bed besides me rubbing his bottom and was surprisingly complementary about my spanking style.
"That is what the head would call a good one, you should ask for a job as spanker in chief."
Simon grimaced as he rubbed his bottom. His _c_o_c_k_ was sticking out and jerking upwards, the tip sticky with a clear fluid. I had never seen another boys erection before and was very impressed with it.
"How does it feel, being spanked?"
It was a naïve question, I could not recall being smacked as a young boy. Simon on the other hand was obviously well experienced in being chastised.
"It sort of builds up, it stings at first and then the sting and the heat gets deeper into my bum, it really hurts a lot after about 12 or so. Now it is like hot pins and needles. The head takes me into the bathroom after he has slippered me and applies a wet flannel, that takes some of the pain away."
Simon got up off the bed. I quickly tidied the bed whilst Simon went into the bathroom, I went in afterwards, his bottom was wet from being flannelled. Simon was inspecting it in the mirror.
"I dont do this when the head is there watching, look how red it is."
As I inspected his red raw backside, Simon was holding up his shirt with his left hand. With his right, Simon masturbated furiously.
"This takes the sting away, I bet you didnt know that did you?"
Simon came, several thin streams of semen shot out of his tip as I watched. Quickly he wiped himself on the flannel before hanging it up.
"Have you ever, you know, practiced doing it with another boy before Gould?"
I didnt have a clue what he meant.
"You know, like you do with girls and stuff. You know, you can practice with me if you want, just dont tell anyone."
My face must have been a picture of puzzlement, I was very aroused but I didnt know what he meant. Simon guessed as much.
"Oh sorry, maybe you dont want to?"
"Come on Mills, we had better get going, it is nearly the end of reading time."
Simon put on his pants and shorts, his pants not covering the marks on his bottom, which were clearly visible on his right rump.
As we walked dowstairs Simon walked quite stiffly as it hurt to walk I guessed.
"Wow, that was a good one!"
"Do you think I will have to punish you again someday?"
"Only if it means I dont get the cane."
That seemed to be an acceptable deal to both sides.
Two days later I was looking after 3b as they changed in the gym. Simon took his position besides the door into the gym. I watched as he changed. He let me have a look at his bottom, it was still slightly pink.
"It was sore all day, but it didnt do any good. I got a bad report from Crook so I am going to have the cane after lunch in any case. You can watch if you like, you can look into the study from the upper toilets far cubicle. It takes place about five minutes after everyone has gone into reading."
Punishments were carried out when the rest of the school was engaged elsewhere, just before assembly in the morning, immediately after lunch and just before tea. The boy to be punished was summoned without a great deal of ceremony and told to stand in the ground floor hallway for the Headmaster to arrive, he then took the boy to what was known as the upper study on the first floor at the back of the new extension, overlooked by our dormitory toilets on the second and third floors.
As a sub prefect, I hurried into the dormitory at the end of lunch and waited upstairs, I was fetching a book was my excuse but no-one asked if you walked like you were not doing anything wrong, just some errand they would assume. Simon arrived shortly after me and stood by the door. About five minutes later, I heard the gravel scrunch as the head arrived and led Simon upstairs.
"Well you know why you are here, lets get it over and done with."
"Yes sir."
"I very much hope I dont have to cane you more than this once this term, is that clear?"
"Yes sir."
A door was unlocked, opened and shut. Then I heard the door locked from the inside. I crept up onto my viewing spot, a window open high above the toilet in the last cubicle. The room was small with cupboards all around it. Simon moved a piano stool into the middle of the room, conveniently in front of the window. As the head reached up for a cane on top of one of the cupboards, Simon undid his shorts and took them down along with his underpants and then stepped out of them and folded them before putting them on the windowsill. He went to bend over, but the head stopped him, presumably to give him a final lecture and then Simon finally bent over, resting his upper body on the passed seat and held onto the rear legs at floor level, his legs stretched out behind him. Just before the caning started, Simon put his legs together and put his head down.
The caning was given methodically, I could hear the "thwick, thwick" of the cane as it struck Simons bottom. Each time he jerked forward. Simon kept quiet to start with but after the fourth stroke, he started to let out yelps of pain. In all he got eight strokes, before the head returned the cane to its hiding place and unlocked the door. Simon stood up stiffly, wiping tears from his eyes, before pulling his shirt down and following the head with his clothes, presumably to the bathroom directly below me.
I stayed where I was, not moving. I heard the front door open and shut before I judged it safe to move. Suddenly I was aware of footsteps coming up the stairs, I was petrified as they came closer and then the door opened to the toilets.
"Gould, its only me, the head has gone now."
It was a stage whisper from Simon. He came into the room.
"Want to see my marks? He gave me some real whoppers this time."
I came out of the cubicle, chastened by my fearful experience and watched as Simon dropped his shorts and pants and looked at the damage, eight stripes that ran more or less parallel across his bottom although two crossed at a considerable angle. His bottom was a fearsome shade of cherry red with blue bruising that was going to last a few days I judged.
As I looked at the welt marks of the cane Simon again masturbated, an exercise I did not yet have a name or purpose for.
"You can do this yourself you know, lots of boys do it at school."
I remained uncomprehending as Simon cleaned up his semen with a flannel and returned to the reading class no doubt ready to show his welts to his classmates if called upon. I stayed in hiding, deep in thought at this experience but still not making the connection between my erotic thoughts and the act of masturbation shown to me by a boy nearly two years younger than me.
Simon was soon in trouble with me again, this time for flicking a ruler at another boy in his class. I took him outside the class to remonstrate with hi.
"Simon you cant act like this and expect to get away with it, I have to send you to the Head."
"I know, but dont send me there, you do it, you know, like last time, spank me."
Not sure quite how this was going to go, I agreed. I took him up to the dormitory. We went into the linen cupboard at the end.
"We are less likely to be heard here." He explained.
Without further orders from me, Simon took off his shorts and pants as I sat on a wooden bench. Simon lay across my knee, in a new position, just over my left knee with my right knee clamping him in.
"It stings more this way."
I began to spank him, not hard, just enough to make his cheeks quiver like jelly but enough to make them begin to pinken.
"Harder, do it properly."
I upped the spanking until I was spanking quite hard, just at the paint where he was gasping with pain. I must have landed 60 or so swats before he signalled to stop. He rose from my knees stiffly, his right hand already working his erect penis. He made an offer.
"We can do it, practice, you know like a boy and girl. I can take it, thats if you want to. Ill show you how."
Simon undid his shirt and then sat on the wooden bench on which I had been sitting on whilst spanking him. He sat upright with shock.
"Ouch! I was forgetting my bum is pretty sore. Sit down, on the bench, and I will sit on you."
We removed our shirts and I took off my shorts and pants so that we were both naked apart from our socks. Simon sat astride me and then without bidding, he took my penis in his hand and spat some saliva onto his hand applying it to my penis. Slowly, he sat down on me, his hand guiding my penis until it reached his cheeks, still hot from spanking, he winced as he parted his cheeks.
"Ooh, its pretty sore."
Simon splayed his legs as much as possible as he lowered himself onto my penis to make it easier for me to enter. I could now fell his hot hole. Simon lowered himself a half inch, his hole gave but not enough. Simon winced a bit, then he relaxed.
"Push it in slowly and pull it out if I tell you and be careful, it bloody hurts if it isnt done right."
I put my _c_o_c_k_ to his anus, I could some from his expression that it was hurting him.
"No keep it there, it relaxes after a little while. Try a bit more now. Thats far enough. Okay, a bit more now."
I took three attempts before I could feel his anus relax and open. Instinctively I thrust upwards rhythmically as I felt his sphincter relax until my shaft was all the way in. Simon was relaxed enough to begin wanking in sympathy even though it was still hurting him. With practice I built up a rhythm of slow in and outs that was bearable for him. Simon shot semen over my stomach, his sphincter locking onto me as I shoved in deep and came in his bottom. I pulled out slowly, impressed at Simons stoicism.
Simon climbed off me, then searched on top of the cupboard and found a wooden ruler 18 inches long.
"This is Matrons favourite spanking implement, I have had a few sessions with this. Will you give me a go with it now?"
"Okay, how is it done?"
"Oh like this."
He lay down on his back on the bench, brought his legs up and held them in place, his _c_o_c_k_ rock hard again.
"20 hard, right across the bum."
I hit him hard four times, he was really grimacing with pain and gasping with each hit.
"Is it okay? Shall I stop?"
"No carry on like that, and make it another 20 from now."
With his encouragement I carried on and spanked him with the ruler until he had a broad band of red across his backside, his sphincter now wide open. Afterwards he rose, shivering.
"I cant lie like that any more."
He got up off the bench and stretched luxuriously, we were both hard again.
"Will you do me up the bum again? I am wide open now."
Simon lay down on the bench face down so that I could do it "doggy style" as he put it. Spit applied I entered his hot passage and sodomised him as requested this time with a lot more thrusting , Simon coming shortly after me.
As we walked back, Simon was walking very stiffly. I marvelled at his randiness.