Taking A Leap (M/M) NEW!

♥ Site recommended story ♥

New to The Canery is this exciting caning story by very special guest author JOELSTRAP.   All the characters are 18 or older. WARNING: ADULTS ONLY!

Taking A Leap by Joelstrap

Puddles! There were puddles everywhere; large puddles and small puddles, deep puddles and shallow puddles. The incessant rain had stopped, but the skies were still overcast, as Struan and I walked hand-in-hand along the road just beyond the edge of town. Behind us North Berwick lay quiet under the gloom of a February afternoon, and beyond it the Firth of Forth was a sullen slate-grey. Ahead was the path which climbed North Berwick Law, a solid volcanic-plug with the Whalebone Arch crowning its summit. We reached the car-park at the start of the ascent. A couple of cars sat there and a number of people were making their way up the hill in front of us.

“Lot of oldies,” observed Struan as we began to climb, catching up an elderly couple with a dog and overtaking them.

“Wonder what it feels like to be old,” I mused.

“Who’s caring?” replied Struan. “We’re young and we can get to the top while this lot are still getting their breath back from the effort of putting on their boots.”

I laughed and squeezed his hand, snatching a quick kiss as I did so.

“Bet that makes the old fogeys behind us furious,” said Struan.

“Because they wouldn’t approve of two boys kissing?”

“Naw!” retorted Struan. “Because they’d be jealous that neither of them was getting kissed by a spunky boy like you.”

I stumbled as my penis leapt swiftly upward, and Struan steadied me.

“Horny bugger, aren’t you?” he said.

“You should know!”

We grinned at each other and continued the ascent.

As we walked, I recalled our session of lovemaking in Struan’s bedroom earlier that morning; and also the conversation which had followed as we lay entwined naked in each other’s arms in post-orgasmic content.

“Oh, boy! That was brilliant,” I breathed as I caressed Struan’s bottom with one hand and stroked his cheek with the other.

“Yeh! So, what we gonna do with the rest of the day, Greg? It’s 29th February after all, so we should do something special.”

“We just did.”

“I mean something we don’t normally do, something new, different; because today’s kind of like an extra. It’s Leap Year’s Day so we need to take a leap and push the boat out.”

“I think we’d just get hell of a wet if we did that,” I said tartly.

Struan’s hand slapped my behind sharply.

I squirmed happily against him and asked what he thought we should do. He considered for a minute or two.

“You ever walked up North Berwick Law?” he asked.

I shook my head.

“I’ve lived here for four years and you’ve been here almost as long, and we’ve never done it. Why not?”

I shrugged. “I guess because it’s just there and we could do it any day.”

“But we haven’t. What about you? Anything you really want to do that we should do because it’s a bonus day?”

I thought for a few minutes while I ran my hand through Struan’s thick hair.

“Remember the film of Oliver Twist that were watching last night? And young Oliver kept getting caned?”

“Yeh; so?”

“You ever wondered what it feels like to be caned?”

“Mmm. I did think last night, when I saw the way Oliver squirmed, that a cane must hurt a bit; and I was kinda glad they don’t use it in school any more.”

“He was acting as a kid though, so I guess it would hurt a boy his age more than a teenager.”

“Probably. So, are you suggesting you want to be caned, Greg, just to find out how it feels?”

“It’d definitely be something different, something special to do on our extra day,” I said.

“Agreed; but it’s not gonna happen, is it? I haven’t got a cane, or I’d do it for you,” Struan offered.

“Gee, thanks!”

“And we don’t know anybody with a cane who could do it. Let’s go and climb The Law and you can think about something a bit more practical that we could do as your Leap Year thing.”

I agreed and we fell to kissing softly and intimately.


There were some boggy bits and the path got steeper as it curved round the hillside and then made for the top. We had overtaken several walkers, and on the last stretch strode past a couple of guys with walking sticks, one who looked about eighty and the other about a hundred.

“Hope there’s a cemetery on the summit,” Struan remarked, “’cos that old buffer looks as if his legs will never make it back down.”

“But there’s nothing wrong with my hearing,” said a voice behind us, making us jump.

“Shit!” muttered Struan. “The bugger must’ve heard me.”

He speeded up and perforce I did too, so that we arrived panting a little on the hill-top. Below us East Lothian lay like a patchwork-quilt of fertile fields. To the west, Edinburgh spread from the Forth to the Pentlands, while southward the ground rose slowly to the distant Lammermuirs. Below us North Berwick sat comfortably by the firth while a mile or so offshore, the huge bulk of the Bass Rock squatted solidly in the grey waters, surrounded by swooping gannets.

“Volcano,” said Struan.

“What?” I asked, glancing down to look between his legs.

“No, you idiot! This! It’s a volcanic-plug; like the Bass Rock out there.”

“Oh yeh. I thought you meant…”

“You’ve got a one-track mind,” he said severely, “and it’s a dirt-track,” he added.

I rolled my eyes at him and towed him over to the whalebone arch. The original had been put here in 1707 and had been replaced several times until a fibreglass one was erected in 2005. We walked hand-in-hand under it. The uniform grey of the skies began to break and a few patches of blue appeared, allowing blinks of sunshine to bring some colour to the monochrome landscape. The waters of the Forth began to sparkle and some of the fields of East Lothian shone green with the prospect of spring. For several minutes we stood and drank in the view and then Struan hissed in my ear, “Hey! Here’s the old codger with the sharp hearing, and his pal, coming up. Let’s go down the far side a bit. I don’t really want to meet him. I don’t think he’s gonna like me.”

“Can you blame him?” I asked fairly.

Struan snorted and we made our way across the rough summit and down the far side for some way. We wandered happily, engaged in desultory conversation, for some time, before making our way round the hilltop and back to the path which would take us down to the car-park and the route into town.

“That’s okay,” said Struan, pointing to the path far below us. “That pair of geriatric mountaineers is well ahead.”

“Looks like they might not need an undertaker on the top after all,” I remarked. “That’s you – wrong again.”

“Any more comments like that,” said Struan fiercely, “and you’ll be the one needing an undertaker!”

Bickering amiably, we plunged downward and were soon approaching the car-park. We were dodging small puddles, and then we came across a very large one near where the path ended. It was the puddles, you see, that were the cause of it all.

“Come on,” I said, “it’s Leap Year’s Day! Let’s leap it.”

It was probably because we were still holding hands that we failed to jump as far as we should have done; and ended up landing with a tremendous splash about two thirds of the way across the puddle. It was deeper than I’d expected and a veritable deluge of muddy brown water flew in wide arcs in all directions. There was an almighty bellow of rage and we turned and saw, to our horror, that the two old guys about whom Struan had been so rude, were standing, dripping with dirty water.

“Oh, fuck!” gasped Struan in my ear as we waded out of the puddle and approached the pair.

They didn’t look pleased and I could hardly blame them.

“I’m really sorry,” I began. “We didn’t do it on purpose, honest. We couldn’t jump as far as we thought we could.”

“Maybe we could help dry you off a bit,” offered Struan, pulling a grubby-looking hanky from his pocket.

“No thank you,” said the older of the two, glancing disapprovingly at the hanky as if he feared it might be infected with Bubonic Plague. “If I’d behaved like that when I was your age, I’d have had the skin taken off my behind with my dad’s cane. I’ve still got it, and it’s exactly what young hooligans like you need. Do you good.”

“Er, yes,” said Struan. “Anyway, we’re really sorry.”

As this brought forth nothing but angry glares from both men, we turned and squelched our way towards the road back to town. A thought struck me and I grabbed Struan’s arm tightly.

“Struan! Do you think this could be it? The chance for me to do the unusual thing I want, to mark Leap Year Day?”

“What? Go and ask that old dinosaur to cane us you mean?”

“Why not? He just might. He obviously wants to; and he’s hardly gonna be able to hit that hard at his age, is he?”

“Suppose not. Okay, let’s give it a go; but he’ll probably just tell us to go to hell.”

“So what? At least we’ll have tried.”

We turned and re-entered the car-park where the elderly pair were trying to dry themselves off with hankies which were decidedly cleaner-looking than Struan’s was. The younger of the two was leaning on a fence-post a few metres away as he squeezed water from his trouser-bottoms. The one who looked about a hundred was patting his hair with the hanky and scowled unpleasantly at us as we approached. This was the thing I wanted to do on the extra day, so I felt it was up to me to ask the question.

“Look, we both feel really bad about what we did, and although it wasn’t intentional, we realise it was thoughtless and stupid. You said that you thought we needed a good thrashing and so…well, if that’s what you think we deserve, we’re ready to take it.”

The old boy stared at me for several seconds.

“Are you trying to make fun of me, boy?” he roared suddenly, making us flinch.

“No, sir. Honestly, I’m not,” I pleaded. “I know this is going to sound a bit weird, but I’ll tell you exactly why I’m asking.”

I explained about the Leap Year’s Day idea of doing something unusual, something each of us wanted to do, but never had. I explained about Oliver Twist too, and how the idea had come to me.

“So in a way,” I ended, “it’s not just that we know we probably should be punished for our behaviour, but also that you’d be helping us do the second of our Leap Year Day special things.”

He stood in silence, contemplating us both for some time. I resisted the temptation to say any more. I’d made my case and the verdict was up to him.

“I said you deserved it and I stand by that,” he said at length. “I’m not sure that I could use my cane effectively on tough youngsters like you pair though. Still, maybe Andy could make more impression on your behinds. All right; six of the best for each of you in the traditional way with my senior cane. It will hurt. Go and have quick think about it and tell me if that’s really what you want.”

We walked across to the edge of the car-park.

“You up for it, Struan?”

“Yeh. You’ve done my special thing, coming up here, so I’ll go along with yours. I never thought it’d happen though. A caning! Who’d have believed it?”

“His mate; Andy I think he called him; he doesn’t look too much of a threat either. A bit younger but I should think we can take anything he dishes out.”

We both looked across at the younger of the two old chaps, who was now polishing his mud-bespattered glasses.

“Yup. Right, let’s do it.”

As we walked back across to the old guys, a small car slid into the car-park and came to a halt nearby.

“We’ve agreed that we’ll take the cane,” I said.

“Good. Here’s Andy now,” the ancient man added as the car-door opened and a guy in perhaps his early twenties jumped out.

He was about six feet tall with a lean figure and an open face crowned with a mass of dark curly hair. Leather boots, close-fitting jeans, a plain denim shirt, open at the neck, all helped to reveal rather than conceal his dominant physical presence.

“Hi, granddad,” he said cheerfully. “Hi, Rob,” he added to the other elderly man. “Hope I’m not late to pick you up?”

“Perfect timing,” the old guy assured him.

“Did you fall in a bog?” Andy enquired, taking in the muddy appearance of his granddad and his friend.

“No, we didn’t. This young pair of scallywags will explain.”

Andy turned a questioning face towards us and I glanced uneasily at Struan. He took a deep breath and made a full confession, though saying nothing about the punishment. The old guy, however, insisted that Struan spell it all out himself. I watched as my gorgeous boy flushed with embarrassment as he explained about the caning and why we were up for it.

“Wow!” observed Andy, a broad grin splitting his sexy features. “You two have got guts. That cane’s ferocious. I asked granddad to give me a couple of strokes when I was sixteen, just to feel what it was like. I guess it’s one of these things that guys like to know about,” he said, “so you’re probably not so unusual. But it hurt, I’m telling you. I mean really hurt!”

“I guess it’s meant to,” I said, trying to sound nonchalant while my stomach churned.

“You’ve probably made the old boy’s day,” he said. “He was a teacher, you know, and I think he enjoyed using the cane.”

“I did not,” retorted his granddad. “I used it when necessary to impose firm discipline and it worked. My classes were well-behaved and worked hard.”

“I bet they did,” Struan muttered in my ear.

“Anyway,” the old chap continued, “at eighty-six I doubt if I could get through to young lads like these, so I suggested you might like to do it and they agreed.”

There was a very definite twinkle in his eye as he added, “I’m afraid that I may have given them the impression that my eighty-year old companion here was Andy.”

Andy threw back his head and roared with laughter.

“Shit!” he gasped. “I bet you two got a shock when I appeared and you realised that I was Andy. Granddad’s as sharp as a tack. Nobody gets the better of him.”

“So I see,” I acknowledged ruefully. “Being caned by you is gonna be a hell of a lot tougher than getting it from your granddad or his pal.”

“Thinking of backing out, are you, boys?” enquired the old man.

It had crossed my mind, but I knew it would make us look like abject cowards.

“No,” we both said together; and I was pleased that we had agreed independently.

“Shall we say eight o’clock this evening? I’m assuming that you both live in North Berwick?”

We nodded our assent and he gave us a small neat card with his address printed upon it.

“Don’t be late,” he instructed.

“Will we get extra if we’re late?” asked Struan in an attempt at levity.

“Yes,” said the old man.

Neither of us smiled as we headed for the road.

We trotted towards the town in silence for a time, each holding hard to the other’s hand.

“That sexy young bugger is really gonna beat the shit out of us,” I said eventually.

“Do you think it maybe hurts less when the guy caning you is as hot as hell?” asked Struan.

I was doubtful. “I think when he’s making our arses as hot as hell, we won’t be thinking about how sexy he is. Are you angry with me for getting you into this, Struan?”

“No way! We’re in it together and we’re not cowards. For shit’s sake, we’re eighteen! We’re not snotty kids like Oliver Twist. We can take it; and then you’ll have got your special thing and I’ve had mine.”

A thought struck me.

“We went under the arch of the whalebone on the hilltop; and tonight we’re going under the arch of the cane,” I said.

“Hmm,” replied Struan, “but the whalebone didn’t come crashing down on our backsides. I bet that brute Andy arches the cane to let us see it before he beats us; but then that arch is gonna play merry hell with our bums!”

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On Struan’s advice, we wore loose-fitting jeans rather than the tight ones we normally favoured, as he thought the cane would hurt less that way. Just on eight o’clock we rang the bell at a neat bungalow and the old guy admitted us and took us into a small study where Andy was already sitting.

“Congratulations,” he said to Andy, and he handed over a ten-pound note. “I foolishly bet young Andy here ten pounds that you wouldn’t turn up,” said the old guy, “but he was confident that you would; and it seems that he was right.”

“But you might wish you hadn’t turned up,” said Andy, “by the time I’ve done with you.”

We flashed each other a strained smile.

“Over to you, Andy,” said the old guy as he took a seat by the wall and Andy stood up.

Tonight he wore black jeans which fitted closely enough to reveal a stunning pair of fully-rounded buns and a massive bulge between his legs. A studded black leather belt girt his waist and over his torso he wore only a tight blue T-shirt which showed off his impressive pectorals and biceps. I felt my penis harden as I looked at him. He opened a cupboard and took out a lithe cane. I’d never seen one before except in films, and it didn’t look too bad. It was quite slender and by holding it in both hands, he was able to bend it easily into a smooth arch. He suddenly released one end and slashed it swiftly through the air with a vicious whine which made us both wince instinctively.

“Think you’ll feel it, boys?” he enquired.

“Yes, sir,” we replied in unison.

We hadn’t decided in advance to address him as sir, but it clearly came naturally to us both in the circumstances.

“Right,” he announced, pointing to me with the tip of the cane. “Name?”

“Greg,” I replied.

“Jeans and pants off, Greg!”

“What? But you can’t give it to me bare!”

“I won’t be bare.”

“I meant that I’d be bare,” I stammered.

“Yes, you will be,” said Andy. “Hurry up!”

“But I…”

“No you don’t. You get your jeans and pants off NOW!”

I threw a hopeless glance at Struan and then obeyed. In spite of my nervousness, my penis bounced free from my pants at almost full erection. I put my clothing on a chair and waited, deliberately keeping my hands at my sides. After all, I was a young guy; I had nothing to be ashamed of; and in a curious kind of way it pleased me that Andy should see that I was a big boy.

“Yes, very impressive,” remarked Andy with a grin, “but I’ll soon get rid of it for you.”

This remark had the perverse effect of making my cock strain for another few millimetres of length.

“Bend over the desk, grasp the far side with your hands and put your feet wide apart.”

I complied with this order and he checked that I was positioned as he wanted me. I waited, feeling my heart pounding against the solid wooden desk, staring straight ahead at a row of books on a shelf. With a start, I realised that one of them was Oliver Twist! My pondering on the likelihood of this happening was interrupted by the tapping of the cane on my rump. It felt light and teasing, as if he was exploring and trying to decide exactly where to hit me. When the stroke came, it took me completely by surprise, lashing powerfully across the centre of my bare bottom and delivering a searing blast of pain which made me gasp aloud and clench my buttocks desperately.

I swiftly adjusted my brain to the new situation. This was no game and it certainly wasn’t easy. The pain-level was far beyond what I’d expected and the writhing of young Oliver in the film the previous evening suddenly appeared to have been under-acting rather than over-acting. I realised that I was holding my breath and, even as I released it, Andy plied the cane a second time, lacerating my flesh with another streak of fiery torment. I tightened my grip on the edge of the desk, rode out the burn, and tried to ready myself for more. I failed miserably. The next stroke whipped viciously into my lower bottom and forced a yelp of agony from me as I felt my body twist in a spasm of savage pain. Furious with myself for losing control and letting him know that he was getting through to me, I gritted my teeth and settled my feet firmly in position. There came the whistle of the punitive rod, the snap as cane and flesh were brought into violent contact, the slash of blazing fire across my behind, and then the half-stifled squeal as the pain-level soared.

I breathed hard, fighting to keep my body in check. I was aware that Andy had managed to get rid of my erection, as he’d promised; but he wasn’t going to break my spirit. I dug deep into reserves of strength and steadied my quivering buttocks. Andy hit them brutally hard. I writhed and I was aware of scalding tears on my face, but there was only one to go and I was going to take it. As the tsunami of pain subsided a little, I gathered my battered resources and prepared for number six, forcing myself to breathe deeply, consciously stilling the quiver in my buttocks. The cane bit deep into the sensitive flesh where bottom merges into upper legs and I felt my body buck violently as a white-hot blade of fiery heat seemed to scythe its way to the very heart of my being. My head came up and I yelled my pain to the unresponsive wall.

When he told me to stand up, I did so with a sense of weariness, as if I’d run a marathon. There was a sense of achievement too that I’d got through it. I felt behind me and explored carefully the raised welts on my bottom, so sensitive that even the light touch of my finger-pads made me wince.

“Over there,” ordered Andy coldly and I took up my place by the wall as he summoned Struan to bare his behind and bend over the desk.

I knew Struan’s bottom intimately and the sight of it bared and vulnerable to that brutal cane gave my penis an unexpected boost. Now I could see and admire Andy’s prowess with the cane. He made full use of his muscle-power and also twisted his lithe body round so as to get maximum force behind each stroke. He looked superb as he wielded the cane and I found myself watching him more than I was watching Struan; until the rod hit home and I saw the line of white across my boy’s buttocks, which quickly became a raised welt and turned an angry red. Struan was silent but I could see the high tension in his body as he waited.

The cane lashed him again and although he bucked, he remained silent. Andy flexed the cane a few times and then took aim and delivered a stroke which broke Struan’s silence, forcing a strangled squeak from him. My penis was rock-hard, reaching for the ceiling as Andy lined up the fourth stroke. Whether by accident or design, it landed almost exactly on top of the previous one and extracted a yelp of outraged agony from Struan as he writhed on the desk-top. Andy waited until he had stilled himself and then gave him the penultimate cut. Struan bucked and his gluteal-muscles clenched and unclenched as he fought the burn, but no sound escaped him. I held my breath as Andy prepared to mete out the last stroke. I knew where it was going and Struan, having seen what I’d been given, must have known too. His whole body was rigid with tension, but his bottom had been pushed firmly up. Andy drove his cane ferociously hard into Struan’s crease and a roar like that of an angry lion came from his throat as his body squirmed. Pre-cum was oozing from my straining penis as I watched Struan calm himself and regain control of his body. He stood upright slowly on Andy’s command and moved his splayed hands carefully over his beaten rump.

“That,” he said to Andy, “was hell-of-a sore!”

Andy smiled at him.

“Got through to you, did I? That’s what I was aiming for.”

“You got a bullseye,” said Struan ruefully.

“Me too,” I concurred. “I never expected it to hurt as much as that.”

“But you seemed to enjoy watching your mate get it,” remarked Andy, nodding at my rampant organ.

“Sorry, Struan,” I said. “It just happened.”

“You don’t need to apologise to him,” interrupted Andy. “You should have seen his boner while I was caning you!”

“Er, yeh, I’m afraid so,” Struan admitted shamefacedly. “I couldn’t help it.”

“More importantly,” said the old guy, rising from his seat and coming forward, “what have you learned from being caned?”

“Not to behave thoughtlessly and inconsiderately,” I replied at once.

“And to be respectful of older guys, sir,” added Struan very politely.

“Job done, I’d say,” observed the old guy. “But you also wanted to find out what a caning felt like as your Leap Year Day new experience; so what did you think?”

“Like I said, it hurt a lot more than I expected,” I replied, “but the challenge was kind of exciting too in a way. I almost felt as if I was fighting you,” I said to Andy, “determined not to let you break me; and that you were fighting back, trying as hard as you could to force as much reaction as possible out of me; and you succeeded with that last stroke. It was a screamer!”

“It was tough taking it after I’d watched what the cane did to Greg,” admitted Struan, “but I was determined not to make any sound if I could help it. I know I wasn’t very successful because I only managed the first two in silence before you broke me. I kept the sound in for the fifth one, but it definitely all came out at the sixth.”

“Are you glad that the cane wasn’t in use when you were at school?” the old guy asked. “I should say that it wasn’t normally used on a boy’s bare bottom and not usually as hard as Andy used it; but he was caning young men of eighteen, not schoolkids.”

“I think,” I said slowly, “that I’d rather have had the cane than detentions or lines; and I think it would have had a stronger effect in keeping me working hard and behaving myself,” I admitted.

“Same here,” added Struan. “I’d have been making serious efforts to avoid it, so I guess I’d have been better behaved.”

“Okay, lads, get your clothes back on and then you’re free to go. It’s been a pleasure to see my old cane back in action and to see a couple of well-chastised boys who have learnt their lesson.”

Andy saw us to the door and asked a bit more about our Leap Year doings. I explained about climbing North Berwick Law and going under the whalebone arch.

“I never thought I’d get my special thing and go under the cane’s arch though,” I said. “But then it happened out of the blue with that bloody puddle! It’s Leap Year, so we decided to leap it; and failed. Then when your granddad talked about caning us, it seemed like it was meant to be. We decided to leap at the chance, you might say. Your granddad’s a cunning old devil though. We thought that Andy was his old pal and we looked at him and decided that he wouldn’t be able to hit us that hard. We did remember to look before you leap; but the clever old bugger misdirected our looking; and by the time we looked the right way and saw you, we’d already jumped!”

“Will you be going back up The Law?” asked Andy.

“Yeh,” replied Struan. “Definitely. It’s a great little climb and brilliant views. I’d like to go up on a summer day and watch the sunrise from the top.”

“If,” said Andy, “you ever feel that you’d like another session under the cane too, here’s my mobile-number. Just give me a buzz. I’d be delighted to oblige.”

He shook hands with us both and we made off out on to the street.

“How’s your arse?” asked Struan.

“Hurts like the devil. It’s fantastic.”

“Me too. I’m horny as hell and I can’t wait to get into your pants.”

“So why are we walking? Let’s run!”

We ran, and arrived panting at Struan’s home, where we lost no time in indulging in a long session of uninhibited and gloriously thrilling sex.

“Wow!” I gasped. “Just wowsity, wow, wow, wow, wow, wow!”

“You still got Andy’s mobile-number?”

I nodded.

“That’s good. I think we’re gonna need it!”

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Story ©MMXX by Joelstrap, and used here by very kind permission of the author.

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D I S C L A I M E R

All characters and businesses appearing in this story are fictitious. Any resemblance to real persons, living or dead, is purely coincidental.

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Joelstrap’s excellent earlier stories for The Canery are available here.  Further great stories by Joelstrap may be found at this external link