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Naughty Boys Caned

by Sandy

Copyright on this story text belongs at all times to the original author only, whether stated explicitly in the text or not. The original date of posting to the MMSA was: 10 Dec 2007


I saw Rupert almost daily, both in and out school, until he moved to another part of the country with his parents at the age of eleven. We maintained our friendship by writing regularly and spending a fortnight together each year at the end of the summer holidays. One year he would he would stay with me and the following year I would visit him. In both houses we had to share a bedroom but in Rupert's house we had to share a bed too. Sharing a bed with Rupert was not a problem: it was great fun. We had a pillow fight almost every day. An imaginary line was drawn down the middle of the bed and, being territorial, we fiercely defended our halves of the bed. Since we never wore pyjamas during the long hot summers we both slept on the very edge of the bed to avoid any form of bodily contact and by and large it worked. I always enjoyed my stays with Rupert; they were very relaxed affairs which helped me to forget that the start of the new school year wasn't far away. Then one summer the nature of our friendship changed for ever. We were both fourteen and it was a visit that I would never forget. Unlike previous vacations, it turned out to be one of extremes: tremendous highs followed closely by painful lows.

As we stripped off to go to bed on the first night of my summer visit, I was surprised to see how much Rupert's body had changed since we last met a year ago. His shoulders had broadened above a now finely toned chest that was fast changing from that of a boy to that of a man. Gently swelling biceps were now clearly visible indicative of his new found strength. But it was below the waist that fascinated me the most. A luxuriant growth of pubic hair now topped an appetisingly long penis thrust forwards by two deliciously spherical testicles resting between strong thighs. I was mesmerised by the sight of his penis: I had an overpowering urge to hold it in my hand but was too shy to ask. Some deep instinctive craving made me want to take his penis into my mouth. I didn't know why? Back then I'd not heard of fellatio. I was taken aback by how much his body aroused me. Why should I feel this way? I searched for reasons but found none. I used to enjoy the feel of his body next to mine when we wrestled together as young children, particularly when he sat astride me and held me down until I surrendered. It was fun but did not explain why I now found his body to be so attractive.

We got into bed and lay on our backs staring at the ceiling while we talked for hours: we had a lot of catching up to do. Gradually sleep began to take over: we turned on to our sides and drifted into a deep sleep. I woke in the night to feel Rupert's bottom pressed against mine. I suppressed a natural urge to back away. It felt so nice and my penis stiffened in agreement. But surely it wasn't right for me to aroused by the feel of another boy's bottom touching mine. After a while, I plucked up enough guilt to retreat. Lustful thoughts tumbled around in my head as sleep gradually took over again. At six o'clock in the morning I awoke again to a bigger problem. Rupert was cuddled into my back with one arm resting on my shoulder and his penis nestled comfortably between my buttocks. He had an early morning erection, or so I thought: it was huge and felt deliciously hard as I naughtily wriggled my bottom against it. He was breathing slowly and deeply, clearly fast asleep. Fully aroused now, I wriggled to position the entrance to my bottom over the head of his engorged phallus. It was absolutely divine but only minutes later the alarm clock in his parent's room burst into life. It didn't wake Rupert but he did, much to my disappointment, roll over on to his other side.

I awoke again about nine, got out of bed and went to the bathroom. When I returned Rupert stirred and greeted me with a cheery "Good morning". While I was putting on my underpants, Rupert leapt out of bed and disappeared to the bathroom. As I picked up my trousers some loose change fell on to the floor. I got down on to my hands and knees to collect the scattered coins. There I noticed that a penny had rolled under the bed. So with my shoulders under the bed and my bottom sticking up in the air I reached forwards to get it. The door opened, signalling Rupert's return. A hand playfully slapped my upturned bottom which must have been such an inviting target stuck up in the air like that. Then a thumb pressed against my bottom as if it were about to rodger me. I squirmed with pleasure but wasn't yet ready to admit that I liked it.

"Get off," I protested loudly but half heartedly.

"You liked it earlier this morning."

"You weren't asleep?"

"Of course not."

I moved out from under the bed and knelt upright to see Mark dressed only in his underpants. He was standing very close. I could clearly see the outline of his testicles and erect penis pushing up to one side. My penis stiffened in anticipation.

"You like?" he asked thrusting his genitals against my lips parted in admiration.

"Mmmm..." was all I could say.

I grabbed the waist band of his briefs and pulled them down. His penis leapt out now free from all constraints. My covetous eyes followed the thick blue veins as they wended their lazy way up to the head of his penis. I wrapped my fingers around the shaft to feel its warmth and masculine hardness, and revel in the tactile pleasure of its silky smooth skin. I breathed deeply to sample, what I now know to be, the fragrant musky aroma of an aroused male as I passed the head of his cock back and forth across my parted lips. I pulled back his foreskin and licked the silky smooth head. My tongue danced greedily up and over and around the head before taking his cock deep into my mouth. His hand grasped my head as it bobbed up and down like a nodding donkey while my right hand slid up and down the rock hard shaft. As the first drop of pre-cum leaked from his penis, I pushed the index finger of my left hand between his thighs to finger his bottom. His penis twitched with pleasure and then erupted with orgasmic delight as I pushed my finger up his bottom as far as it would go. Semen hit the roof of my mouth. I held his twitching penis steady as it erupted again and again. I swallowed but some semen escaped and ran down the shaft and on to my hand. It was time for breakfast.

On the Wednesday evening we went to the local cinema. Rupert led me to a seat in the middle of the back row. I was surprised by his choice of seats but a little excited by what this might signify. It was a weekday so the cinema was almost empty. No one else was sitting in the back row; we had it to ourselves. Half way through the film he grabbed my hand, and there it remained until the film ended. On our way home he led me down an unlit lane between two rows of terraced houses. He claimed it was a short cut but I thought he had other ideas: he did but it wasn't the one I was thinking about. There in one of the gardens backing on to the lane, we saw some delicious apples hanging temptingly from a tree. He thought that it would be good sport – we called it scrumping – to pinch some apples. It wasn't that he was particularly fond of apples: what he enjoyed most was the excitement of taking the apples without getting caught and, of course, there was always the potential thrill of being chased by an irate owner. Looking back it all seems very juvenile but at the time it was great fun. The garden gate was not locked so we walked in and down a short narrow path between a boundary fence and a large wooden shed. In the reassuring distance a light dimly illuminated the garden from behind drawn curtains but there in front us in all its splendour was a tree fully laden with delicious apples; surely they wouldn't miss a few. My heart pounded with excitement and fear as Rupert swiftly climbed the tree, picked some apples and dropped them for me to catch. A minute later my arms were cradling about half a dozen apples.

Rupert climbed down the tree and as he touched the ground we became blinded by the light of a torch. Someone had been watching us from inside the shed. It was the house owner; he was furious. He grabbed us both by our ears and dragged us kicking and screaming into the shed. We tried to break free but he was too strong for us. Once inside, he said that he would cane us for stealing unless we would rather he called the police. Naturally, we readily agreed to a caning. Who wouldn't in such circumstances? Without further ado, he angrily ordered Rupert to drop his trousers and bend over a strategically placed sawing horse. There he roughly pulled his underpants down before attacking his bottom with a garden cane. Six strokes whipped across his pale buttocks that evening leaving purpley red weals to remind him not to steal apples. Rupert withstood the onslaught bravely but even he was sobbing by the sixth. Then it was my turn; I was not as brave as Rupert. I was yelling by the fourth and thrashing my legs uncontrollably by the sixth. He sent us on our way with a clip across the ear. We hobbled home in silence, massaging our shredded buttocks with heads bowed low in disgrace as we fought back tears. As I grimaced with pain, I tried to balance the thrill of the sport with the fire in my bum but the scales weighed heavily against our foolishness.

We arrived home and went straight to bed, desperate to avoid a long chat with Rupert's parents who would surely have detected some sign of distress even if it was only an eye red from crying. It was quite late so no excuse was required. Stripped naked we inspected the damage to our bottoms. Six evenly and closely spaced stripes adorned our pale bottoms; this guy had obviously wielded a cane before. Looking at Rupert's bottom made my penis harden. I quickly climbed into bed to hide my embarrassment. Rupert followed and we comforted ourselves with a cuddle. I closed my eyes and as I did so I felt Rupert's lips brush against my eyelids before descending to my expectant lips parted by desire. It was a long gentle unhurried sort of a kiss but, together with the closeness of our naked bodies, it was enough to get our penises good and hard. A hand stroked my bottom as his index finger explored the cleft separating my buttocks. Tantalisingly, his teasing finger hovered over the opening to my bottom before plunging deep inside. As I wriggled and squirmed with delight, and with my thoughts accelerated by lust, I wondered what it would be like if my bottom were to be similarly impaled on the end of his penis. I wrapped my fingers around his warm hard cock as he grasped mine.

Lost in our intimate embrace we didn't hear a sound until the bedroom door opened. We froze, too afraid to move. A few seconds elapsed, but consumed by fear it seemed like hours, before we heard the door close again, followed by the distinctive clip clop of high heeled shoes on the landing. It must have been Rupert's mum checking that we were alright. As soon as she opened her bedroom door we separated afraid that Rupert's dad might check on us later. Rupert soon fell asleep but I lay awake worrying that she might have seen us kissing each other. My mind wandered around in circles trying to ease my fears. It was dark; she couldn't have seen us. If she had, she would have shouted at us there and then. She might tell Rupert's dad, of course, who may then decide to deal with us in the morning. But why would he do that? Surely he would want to stop us now in case we became sexually more adventurous. My mental meanderings stopped abruptly when the silence was broken by heavy footsteps on the stairs. A bedroom door slammed shut. I waited for an eruption of anger. There was none. I fell asleep, confident that we would not be punished for our playful behaviour.

Next morning I awoke yet again to feel Rupert cuddled into my back. This time his delicate fingers teased my nipples to stand erect, making me more excited than ever. I loved to feel his thumb moving up and down over my aroused nipples. I wanted to tell him to stop – it all seemed too girly – but I didn't. I just relaxed and surrendered myself to his caresses. Wave after wave of excitement washed over me as his rock hard penis prodded my bottom.

"Rupert! Sandy! It's time to get up," shouted sweet Emily, Rupert's five year old sister.

"Just a minute," shouted Rupert afraid that she would rush in the unlocked door and see us so intimately coupled.

After our earlier whipping we thought our troubles were over but sadly that was not be the case. A few days later Rupert's dad summoned us in to his study after we had finished dinner. He didn't look at all happy.

"Amy has just told me that she saw you two playing mummies and daddies."

"What?" exclaimed Rupert sounding totally bemused.

"She saw you two kissing each other in the lounge."

"That's not true," Rupert replied hoping that his dad would believe him rather than his five year old sister.

"Don't make matters worse by lying. Sarah saw you too," he replied calmly but clearly very irritated.

"Oh," Rupert muttered realising that the argument was lost: his dad would believe his elder sister, Sarah.

"How long has this sordid behaviour been going on?"

"Oh that was the first time. We won't do it again dad," he replied confidently.

"Why should I believe you?"

"Well, we were only practising," he lied.

"Practicing? Practicing for what?"

"We are meeting some girls tomorrow night," he lied again.

"That's no excuse. Your behaviour has been abhorrent. Boys don't kiss other boys under any circumstances. It's not normal. As a punishment, I shall cane you both but if you misbehave again in this way I shall send Sandy home with a note for his parents and these summer holiday exchanges will cease for ever. Do you understand boys?"

"Yes, we won't do it again," we replied hanging our heads in shame.

"You had better not. I shall punish you both in the lounge at eight o'clock. Now get out."

We rushed out of his study and straight out of the house. Rupert was not his usual confident self. The fear so evident in his face was beginning to get to me. He told me that we would be caned in front of the entire family: it would be so humiliating. We didn't blame Amy: she would have told her dad that we were playing mummies and daddies in complete innocence. She wouldn't have realised that it would get us into so much trouble. It was fortunate that she only told him that we were kissing. If she had explained that Rupert was lying on top of me at the time, Rupert's excuse of practicing would have been quickly dismissed. We wandered around aimlessly in fear and trepidation as we contemplated our fate in silence. With the appointed hour getting ever nearer our wishes swung wildly from one extreme to another. One moment we wanted to delay our caning for as long as possible and in the next moment we wanted to bring our whipping forwards so that our ordeal would be over sooner. At the time, our fear appeared to be worse than a caning but subsequent events proved that premise to be false.

We arrived back at the house to hear the hall clock striking eight. We hurried along to the lounge not wishing to be late and incur further wrath. We entered on the eighth stroke; Rupert's family were already assembled. No one was seated which somehow added to the formality of the occasion. Amy and Sarah stood next to their mother at one end of the room while his dad stood holding a crook handled cane at the other end. A music stool was positioned in the centre of the room. It stood in splendid isolation with ample room to swing a cane. We stood nervously next to Amy and Sarah as we waited to be disciplined.

"We all know why we are here so I don't intend to go over this sordid episode again. I want to take this opportunity to show Amy how I punish naughty boys and to reassure her that I don't cane naughty girls. Instead, I take them over my lap and spank their bare bottoms. Isn't that right Sarah?

"Yes daddy," she replied blushing deeply as any sixteen year old girl would on hearing her intimate secrets revealed to mere boys.

"So Amy, you know what to expect if you're naughty."

"Yes daddy, you will spank my bottom," replied a nervous looking Amy gripping her mother's hand tightly.

"That's right Amy. Now Rupert! I shall cane you first. Drop your trousers! Yes, and your underpants. Now bend over the piano stool. Pull that shirt up!"

Oh, this was just too humiliating. I wasn't expecting to have to show my bare bottom to a pair of silly girls. It was alright for Rupert; his sisters must have seen his bottom many times before. My attention was briefly diverted by the sight of Rupert's shapely bottom bending over the piano stool to receive the cane. Alas, I was too frightened to appreciate the nicely rounded curves of his buttocks. A dark eerie silence filled the room. The girl's looked petrified. Their mum closed her eyes unable to watch her son being whipped. Three light taps of the cane broke the silence and signalled the arrival of the first blistering stroke. As the first stroke tore across his buttocks with a splat, Rupert gasped for air, the girls and I winced and so did their mum. A pale thin stripe emerged across Rupert's bottom which, by the time the next stroke screamed in, had darkened to a deep red. As the cane bounced high off his bottom, a second stripe joined the first to add to Rupert's agony. I winced as the third stroke whistled in to make its mark as did the girls; their mum covered her ears not wishing to see or hear her son's thrashing. Amy started to cry. The fourth had Rupert's bottom wriggling and writhing in pain. His mum ran out of the room too distressed to remain. A crying Amy ran out after her but was stopped by Sarah. Rupert's legs thrashed around wildly after the fifth, the cane having obliterated any semblance of self control. Sarah held Amy close. The sixth compounded the agony leaving him with no other option than to leap up and hop around on the balls of his feet as he furiously tried to erase the fire raging in his bottom. Slowly he brought himself under control, helped I'm sure by the impatient look on his father's face, and returned to stand beside me. It was my turn now. I was scared but surprisingly not as frightened as I was earlier: I should have been.

"Sandy! Step forward! It's your turn to be caned for your lewd behaviour. You know the drill."

I walked over to the piano stool and, with trembling fingers and thumbs, unbuckled my belt. The sound of my descending zip shattered the pin dropping silence. Seconds later like some automaton I watched my trousers slowly descend to form a pool around my ankles. Then I carefully rolled my pants down fearful that they would get caught around my stiffening penis. Why did I have an erection at such an inappropriate time? Deep down in the darkest recesses of mind, did I have a craving, as yet unknown to me, to have my bottom whipped or did I simply enjoy baring my bottom to men? On balance I thought that it was likely to be the latter. Returning to reality, I submissively bent over the stool hiding my erection with the front of my shirt. I didn't pull my shirt up to expose my bottom until my penis was safely sandwiched between the stool cushion and my tummy. I gripped the horizontal rung on the stool and waited for the assault on my bottom to begin. Rupert had not cried out. I hoped that I had the courage to be as brave as he was. The sound of shuffling feet warned me that his dad was aligning the cane with my bottom.

The first stroke screamed through the air to knock the wind out of my lungs and bite my bottom with all the stinging venom of a thin line of bees. I gripped the rung with all my strength as I tried to come to terms with the fire spreading through my bottom. My erection was sinking fast. The second stroke finished it off as it whipped in across both buttocks to add another fiery weal to my once smooth bottom. I wanted to yell out but I was too ashamed to cry in front of the girls. Instead, I screamed in silence. The third stroke got me bouncing around on the stool as I struggled desperately to control my tormented body. Involuntary tears poured down my cheeks as evidence, as if any were needed, of my distress. I was at the end of my tether. The fourth started me yelling, all thoughts of bravery gone. My legs were now thrashing around randomly and asynchronously with my wriggling bottom. Five and six whipped my buttocks in a stinging whirlwind of biting pain. Then no more, only silence save the sound of girly feet hurriedly leaving the room.

"Get up! Go and stand next to Rupert!" he shouted, his anger still not fully quenched.

I pulled up my pants and trousers and then hopped and skipped over to join Rupert, rubbing my shredded buttocks and trying desperately to realign my pain distorted face.

"Since you two can't be trusted to keep your hands off each other I have moved Sandy's things into Sarah's bedroom. Sarah has temporarily moved in with Amy. Now get out of my sight! I don't want to see either of you again until the morning."

We left the house and went for a walk. At first we ambled along in silence as we both tried to come to terms with the stinging fire in our bottoms. Later, when the mind numbing pain had diminished to a warm glow, we agreed that we had been well and truly whipped and as such did not wish to present our bottoms for another dose, ever again. We were just grateful that we had not been caught in a more compromising position. The rest of my stay passed without incident. Although our caning didn't prevent further sexual intimacy, it did stop us from indulging in such practices anywhere near Rupert's house. Instead we found some secluded bushes on the edge of a nearby golf course. No one ever passed by and if they did we would have adequate warning of their approach. There we continued to satisfy our dissolute urges but sadly I had to wait until the following summer before, my desire to take Rupert's penis up my bottom, was realised.



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