An act of chivalry appears to land a boy in trouble while his girlfriend gets away with it.

By Joanna Jones

I staggered slowly out of the headmaster’s office, unable to stop myself clutching the back of my trousers, and barely able to hold in the tears that, despite my eighteen years, still threatened to escape my eyes.

Five minutes previously, I had been reluctantly unbuckling my belt and fly to reveal my plain white Y-fronts, then, trousers around ankles, that same white fabric had been stretched tight across my backside as I reluctantly bent over for six of Mr Gillespie’s very best. Senior cane for a senior boy, or so he said.

Six strokes of the cane, caused by my girlfriend leaving her dropped coat on that bench in the park at lunchtime and insisting I go and get it for her afterward, claiming it was my fault she’d forgotten it. Despite running I still had been far too late back, and had had the misfortune to be caught.

As I staggered into A-level Geography, at least she had the grace to look embarrassed.

After school she caught up with me, full of apologies. I was not really in the mood as the results of my trip to the Head were still an aching throb in my backside. In fact, I was cursing myself for falling for such a ‘high maintenance’ girlfriend.

Eventually she said: “Look, okay, I know it was my fault. I am sorry you know.”

I just shook my head and replied: “I don’t know, I am just a bit annoyed that’s all. Being sorry doesn’t really help my bottom feel any better at this precise moment in time.”

She persisted. “I suppose not, I suppose I need to do something to make it right.”

“Unless you have a magic anaesthetic wand to wave around over my nether regions, I don’t see there’s much you can do, to be honest.” I responded grumpily.

As she trailed along beside me there was a pregnant pause, as if she was thinking, or building herself up to say something. Then she said: “No, there is nothing I can really do to deal with that, but on the other hand, would it make it better if I let you cane me to make up for it? At least then we would be equal.”

I stopped in shock, guiltily realising her offer had caused one part of my body to immediately betray its enthusiasm at such a prospect. Suddenly I felt a bit guilty that my ire had led her to make such a sacrificial offer.

“No, don’t worry,” I replied reluctantly. “It was just bad luck I was caught.”

However, instead of accepting my suggestion to forget it, my girlfriend seemed to start warming to her own idea. “But it should have been me. I should have not made you go. Let me make it up to you.” She wheedled rather seductively, causing my initial resistance to fade further.

“But we don’t have either anywhere to do it, nor an implement.” I continued rather weakly.

“You know my dad still canes me sometimes, if I especially anger him. I know where he keeps it, and mum and him are meeting in London to go to a show tonight.”

The rest of my excuses were even more half-hearted and soon I found myself taking the turning to walk to her house, then phoning my mum from their line to confirm with her it was okay taking Angela on a date. It was a Friday after all.

Putting the phone down, I found her nervously standing in front of me, a two and a half foot cane being rather reverentially offered to me from her hands. For some reason she had changed from her sixth form tights to the junior school white school socks, making her look that bit younger and more vulnerable than her eighteen years of age.

In a bit of a daze I took the stick from her. “Are you sure about this?” I asked.

She nodded. “I was a brat to you, I deserve it.” Then she continued. “I know what I am asking for, don’t go easy on me. You’re in charge now.”

Fingering the cane I looked at her rather pensive face for a long moment and made my decision.

“Very well, I had a very uncomfortable fifteen minutes outside the headmaster’s office, waiting, so I think you can go and stand in that corner with your hands on your head.”

Clearly she expected me to get right to it, so to speak, and began to object: “But…”

“Who did you say was in charge?” I demanded with a raised eyebrow.

“You are, sir.” She replied with rather a sarcastic emphasis on the final word.

“Don’t be sassy, young lady, unless you think a couple of extra strokes are needed?” If I was going to do it then I might as well play the part, I thought.

That seemed to take a bit of the wind from her sails.

“No, sir,” she replied, much more demurely, before she turned and slowly walked to the corner and reluctantly put her hands to her head. Her grey A-line school skirt rose slightly higher above her knee, revealing the smooth flesh of the lowest part of her thighs. The pose caused me to stiffen once more as I gazed at her back.

After ten minutes I decided to up the ante a little. “Take your skirt off then put your hands back on your head.” I ordered quietly.

Her fingers seemed to tremble as she fumbled under the base of her maroon sweater to undo the skirt button behind her back. Finally it gave, and seconds later the fabric slipped down her legs to pool round her ankles.

This time, as her hands rose back up to her head, it was her blouse that rode up, giving me a perfect view of her legs tapering outwards to her rather well shaped bottom, encased in her regulation maroon knickers that even sixth form girls were obliged to wear.

I let the tension rise as I drank in the sight of her legs, legs that I had caressed often enough in the back of a cinema or more rarely on a sofa when her parents were out. (With two brothers and a sister, my house was sadly never vacant.)

Finally I took the cane back off the coffee table and stood up. “Stay still, girl!” I ordered as she began to turn.

Looking around the room I realised I needed to decide where to put her. Short of moving the furniture the obvious location was the coffee table. I gave the cane a couple of swishes to test the space out, causing her to flinch slightly as I did so.

“Turn round, Angela!” I ordered. She did so, the tails of her blouse not quite long enough with her hands on her head to cover the front of her dark red pants, of a colour to more-or-less match the school’s blazer.

After pausing to admire the sight, with a very nervous face I asked more quietly: “Last chance to change your mind, Ange.”

She shook her head and said: “I know what I deserve, Brian.”

“Very well, bend over and grab the edges of the coffee table, and keep your legs straight!”

Slowly she stepped out of the skirt pooled on the floor and took the few steps to the table. After a deep breath she was in position.

Her blouse just covered the top of her knickers and I wondered whether to push the garment right up out the way. I decided against it; a reminder to concentrate my fire on the lower part of her bottom, though never having done this before I had seen enough examples in the changing rooms, and high blows were regarded with contempt by most boys from any teacher who made such a mistake, usually the assistant head, Mr Taylor, on the rare occasions the head and deputy were both out. Fortunately he was very clearly an unenthusiastic disciplinarian, and his careless strokes lacked the vigour of his colleagues.

I was already quite excited seeing my attractive girlfriend in such a pose. As a result I am sure I quite audibly gasped as I approached her left side to hear her whisper: “You can take them down if you want to.”

There could be no doubt as to what ‘them’ referred to and I felt myself go a little weak at the knees, though another part of me was having no such problem.

“W-what did you s-say?” I croaked.

That hoarse whisper repeated itself, uttering the same electric words: “Take them down if you want.”

For a moment I stood utterly non-plussed. While our adventures into petting had included some fairly tentative fumbling inside each other’s respective underwear, this was new territory. Then, suddenly it seemed my body made the decision for me, as my fingers nervously slipped under the base of the blouse to find the elastic of those pants.

A few seconds later they had been gently tugged to her knees, from where they fell to lie uselessly around her feet.

The sight was quite breathtaking, with her two pale bottom checks now prominently displayed and waiting.

It took a brief few seconds for me to get some composure back and finally gently tap the cane right across the middle of those smooth globes.

Angela’s bottom flinched slightly and her hands whitened as she gripped harder in anticipation.

I wondered how hard to hit as I drew the cane slowly back, and it seemed Angela must have read my mind.

“Do it properly, don’t hold back.” She uttered in that nervous hoarse whisper that somehow electrified me still further.


I had done as requested and was rewarded with a small grunt of acknowledgement as a first red line blemished those otherwise perfect cheeks.

Seeing the mark led to a twinge from my own rear, reminding me of my own experience only a few hours previous.


After a pause I had lashed the cane down slightly above the first, a blow taken this time in silence. I knew her father caned her, and indeed she had managed a couple of visits to Mrs Downs to have her bottom attended to at school, nevertheless I was impressed with her stoicism.


I put a bit more effort into the third one but she kept gamely quiet as a further red tramline discoloured her bottom.

A faint “ahh!” escaped her lips on the fourth which was, I thought, pretty hard.

The fifth was fairly low and a bottled up exclamation escaped her.

“One to go,” I said encouragingly as I watched her hips move faintly from side to side to deal with the agony I knew her bottom must be in.

“Hard and low,” she whispered, as much to herself as to me. Our Head always informed a boy of the “one to go.” The rest was something he never uttered or perhaps knew about, the school-yard rhyme, given he invariably placed the last one right at the base of the bottom and it was, equally invariably, the hardest stroke. That experience was of course one that was still fresh in my memory as I lined the cane up one final time.

I decided not to disappoint her, and after that final “thwack” she indeed screamed as she stood and faced me, eyes glittering as she stood clutching her bottom, careless of the view of hair between her legs.

Then, having taken that entire caning without a tear, suddenly she was sobbing in my arms, asking if she was forgiven, a forgiveness that in my view she did not need to ask for. The anger in my heart over what had happened to me earlier had now completely melted.

I cannot really say how it happened, but that comforting turned over the next half an hour into something more than just cuddling.

Eventually she whispered in my ear on the sofa that she had something for me, and broke away. I was more shocked than I perhaps should have been that the ‘something’ was a packet of condoms which she nervously thrust into my hand. For the first time I was invited up to her room where we first found that gently massaging cream into a punished bottom can be much more that just soothing. As for the other firsts that subsequently occurred, that is now a blur of pleasant memories that I will not recount here.

It was as I walked home around half past ten (comfortably before her parents were due home) that I actually wondered about all that happened. Her suggestion to take the trip to the park, the ‘forgotten’ coat that she had demanded I collect, being caught by a prefect in the cloakrooms having come back late, a prefect that was one of her best friends and who did not give the usual flexibility afforded to fellow sixth formers. Then there was the convenient fact that her parents were out for the evening till late, and of course finally the mysteriously appearing condoms from her bag.

Suddenly the oddly desperate need for forgiveness after her caning fitted far better into place.

A Puzzle. Was it all some coincidence, or was it indeed a well formed plan. A plan I had no objection to having been the victim of, I decided, though I should certainly need to ask Angela. After all, maybe a second such evening should be arranged to “deal” with things if indeed the pieces of the puzzle fitted as I now suspected.

The End

© Joanna Jones 2014