The Young Salesman (M/M) NEW!

♥ Site recommended story ♥

New to The Canery is this fine old story by much-missed friend Skinpang, R.I.P. All the characters are 18 or older. WARNING: ADULTS ONLY!

The Young Salesman by Skinpang

Mr Derek Stone was a retired headmaster in his mid-sixties. He was a widower, financially comfortable thanks to a legacy from his late uncle, and lived in an idyllic detached cottage in a quiet village. He had long toyed with the idea of having a conservatory built onto the rear of his home so that he could enjoy sunny days under glass and admire his lawn and garden.

One day the doorbell rang and when he opened the front door he saw a young man who looked as if he was aged about sixteen or seventeen standing on the doorstep with a folder full of leaflets in his hand. The caller certainly looked impressive in an immaculate navy-blue suit with razor sharp creases in his trousers, his well-fitting jacket buttoned up with one button as it should be, a white collar and green tie. His well tailored appearance was enhanced by his handsome smiling face, blue eyes and a delightful fringe of red wavy hair jutting out over his forehead. Derek first thought was that such smart teenagers were very rare creatures indeed these days! He would normally send doorstep salesman packing straight away but before he could speak his young visitor pulled a leaflet from his folder.

“Good morning sir! I represent Grandeur Constructions. Conservatories, Gazebos and greenhouses are our speciality. Could I interest you in any of our products?”

Derek knew of Grandeur Constructions. It was a firm in the nearby town and had a good reputation.

“You might young man, you might! Come along inside and let’s see what you have to offer.”

“Thank you sir. My name’s Gordon Grey.”

“I’m Derek Stone. Come along to the kitchen table. I’m a bit surprised that that a firm like Grandeur Constructions should have a boy to represent them – no offence intended!”

“And none taken sir!” the young man assured him, “But you are mistaken! I am not a boy! I’m eighteen! I’m an adult!”

“Oh! My apologies Mr Grey!”

“Lots of people make that mistake. I’m told that I look younger than my age! And by the way, please call me Gordon! Anyway enough about me!” said Gordon as they reached the kitchen.

“Right. let us stick to first names shall we? Call me Derek! Sit down and let’s see what you’ve got there!”

Gordon sat down and sorted out several leaflets. There were some very attractive designs and the prices seemed competitive. Derek was getting interested.

“May I see the layout outside?” asked Gordon.

“Certainly! Come along.”

Derek led his visitor through the kitchen back door into the garden.

“Oh yes!” said Gordon, surveying the back of the cottage, “Our Octagon model would be ideal here, don’t you think?”

“Yes indeed, but that one is a bit pricey!”

“I could perhaps shave a little off. Say ten per cent?”

“You give me the impression that you are very anxious to do a deal!” said Derek.

“Well to tell you the truth, I’m sort of on probation you might say! You see, Grandeur Constructions is owned by my father! I’ve just finished in the sixth form at school. He says before I can become a partner in the firm and join him in the office I have to know all aspects of the business. I’ll be honest with you, I’m desperate to get a good order!”

Derek had taken a liking to the fresh-faced boy – for ’boy’ he still was to Derek – and was inclined to try and help him by doing business with him. They returned to the kitchen table.

“I might be interested Gordon! But let’s get down to the nitty-gritty and find out what’s in the small print.”

Gordon went through the details one by one. Derek was satisfied with what he had heard.He had even agreed to the price.

“I wouldn’t want a couple of men to come and dig a big hole in my garden and then disappear for a month before I see them again! There’s all too many firms about who carry on like that!” said Derek.

“Our firm is not like that! I’ll tell you what I’ll do. I’ll include a penalty clause in the agreement.” replied Gordon, anxious to complete the deal, “The work completed by the last day of next month or we will repay you twenty pounds for every day that we are late with the completion. How does that strike you?”

Derek put on a grin.

“I’m a retired headmaster! In my teaching days the penalty for being late was six of the best!” he quipped.

“That was before my time!” laughed Gordon, “there was none of that sort of thing at my schools!”

“Anyway, back to the conservatory! I’ll accept your offer!” said Derek.

“I’m so pleased! I am sure you are going to like it. I’ll get the office to put it in black and white then I’ll bring it back and sign it in front of you!”

Gordon was so keen to get the deal signed and sealed that he was back within two hours. They both signed the documents which they needed to, shook hands and parted. Derek was to see quite a lot of the young salesman over the next few weeks. Concerned that the work should be perfect Gordon would frequently visit the site to keep an eye on progress. However progress was not always as swift as he would have liked. Some snags would arise necessitating that some tasks had to be done again. Several outbreaks of heavy rain also slowed down the outside work. At the end of the month there was still a fair amount of work to be done. When the project was at last completed it had overrun by six days!

“Well you’re six days late, Gordon. That’s a hundred and twenty pounds off according to my reckoning!” said Derek.

“That’s what I wanted to see you about, Derek!” replied Gordon, “Are you really going to hold me to that?”

Gordon was sounding almost as if he was pleading. Derek could not understand why he was trying to wriggle out of the penalty clause. After all, business is business.

“You see it’s like this. I was so pleased when I got this order. I thought I had done something that would impress my father, but what with the ten per cent discount I gave you and now the penalty money all the profit has been swallowed up! My old man’s not going to be very pleased with me I’m afraid!”

“It just shows that you’ve got a lot to learn my lad.” said Derek.

“I suppose so.  I should never have asked you to give up the penalty money. I apologise!”

Derek was thinking, so for a moment there was silence in the room. Gordon was such a nice young lad and Derek was feeling rather sorry for him. He was just about to say that he would waive his right to demand the penalty money when Gordon spoke up with a sign of desperation in his voice.

“You remember what you said to me on the first day I was here? The penalty for being late was six of the best?”

“Yes! So what?”

“Will you give me six of the best like you used to in school instead of taking the money?”

Gordon was banking on the theory that Derek perhaps used to enjoy caning boys’ bottoms and would be tempted to accept his offer. He was not far wrong! Derek’s first reaction was one of disbelief! Then suddenly he felt twenty years younger. Suddenly here was a boy standing before him just as many had stood before him before. In those days the boy would have apprehension written all over his face in fearing he was going to be awarded the cane! Gordon too had apprehension written all over his face but in his case it was lest he was not going to get the cane! The money was more important to him!

Derek was almost in a daze as he stared at the boy’s small but perfectly proportioned figure. He could just imagine him bending taut over a chair, that ginger fringe flopping into his eyes and his bottom protruding skyward! Derek found all the exciting feelings he used to get as he ordered a boy to bend over were coming back to him, and all of his body parts seemed to be in good working order! Gordon took the silence to mean that Derek was going to refuse.

“I shouldn’t have mentioned it!” said Gordon, “I’m sorry. Ha! – I don’t suppose you’ve got a cane anyway!”

“Not at all, Gordon! I am still considering it. And I have got a cane!” – Derek had kept his cane for sentimental reasons! – “I haven’t used it for about thirty years! Are you really serious about this?”

“Yes! In any case I’d like to know what it’s like! I’ve seen it on the television and read about it in books and I’ve often wondered it felt like to get it!”

In Derek’s teaching days boys were not anxious to find out what it felt like! He wondered if Gordon realised what he was letting himself in for!

“Okay! If you’re sure you know what you’re doing, you’re on! Six of the cane and I’ll waive the penalty money! I’ll fetch the cane! Oh yes, just while we’re doing this I would like to make it seem authentic, so I will address you by your surname and you will call me sir! Right?”

“Right!”

Derek left the room and returned with the cane. Gordon was feeling a prickling sensation in his bottom as if it was anticipating what was coming to it! Suddenly an innocent piece of wood was looking frightening and menacing!

“All right Grey! Bend over the arm of that chair!”

“Yes sir!”

It was just like the old days! To all intents and purposes Derek was back in the headmaster’s study! Gordon looked exactly as Derek had imagined he would. The hair flopping forward and his bottom, with the trousers stretched to bursting point, facing heaven. Derek flexed the cane, then he swished it through the air and then he gently tapped it on Gordon’s bottom! Every movement he made he was telling himself that it was the first time he had done this for thirty years! He was wondering whether a modern youth could take a beating as the boys of yesteryear used to! They had been brought up with spanking at home from an early age and progressed to school slippering and caning gradually. Feeling a little nervous about striking a boy’s bottom after all those years he raised the cane and brought it down hard!

Derek need not have worried! Gordon reacted just as most senior boys used to in those far off days. He went stiff and taut all over and his fist folded tightly but he made no noise. The second stroke landed and Gordon’s bottom was squirming in the most delightful fashion! Derek knew from years of caning experience exactly how the boy would be feeling. He would be in intense agony and would love to scream out but his ego would not permit him to do so! No boy, however, could avoid the telltale squirming and Gordon was no exception. There came a third swish and a crack and a forth and a fifth. The writhing had developed into a full scale bottom waggle from side to side! Derek raised the cane for the last time and as it fell he said:

“You may get up now!”

Gordon needed no such invitation. He sprang up, grabbed hold of his buttocks, arced his back and flung his head back with his face a picture of agony! That too was the normal post-caning reaction which Derek expected.

“You took that well, Gordon!” said Derek, returning to the use of the first name, “You can be proud of yourself!”

Gordon was in no condition to answer! His face was twisted and his mouth tightly shut while he held his breath until another peak of the ebbing and flowing pain was reached, then he breathed out with a sigh of relief and just had time to gasp out “Thanks!” before repeating the whole process.

“Well you’ve kept your side of the bargain, Gordon!” said Derek, “Now I’ll keep mine! While you’re getting over it I’ll be writing your cheque out!”

Perhaps Derek too needed time to get over it! He found his hands shaking as he opened his cheque book. He stretched out his arm and open and closed his fists a time or two, it helped to steady his hand. He wrote out the cheque and then looked up at Gordon. The boy was still convulsed in the throes of pain!

“I’m afraid there’s going to be a far amount of stinging for maybe an hour or two, Gordon!”

Gordon managed to let go of his backside and go over to Derek.

“I’ll be all right soon!” Gordon replied, “My word, that was quite an experience!”

“One that most boys were familiar with once! But you took it as well as any of them did! Here’s your cheque by the way!”

Gordon glanced at the document and a look of surprise came over him.

“What’s this….?”

“I’ve put the ten per cent discount back on as well!” explained Derek, “You deserve it Gordon, and I can see how much it means to you to show your father that you’ve done a good deal!”

“Well err gosh! I don’t know what to say! That’s very nice of you Derek!”

“I wish you the best of luck in your career!”

“Thanks! I shall see you again though! After a while I’ll come back to see that all is well with the conservatory. Probably in about a week’s time!”

They shook hands and Gordon left the cottage happy but dreadfully sore! He planned to potter about in the garden that evening doing something which did not involve sitting down! Gordon was as good as his word. He came back a week later. He was, in truth, keen to talk to Derek again. He had become fascinated by all aspects of school corporal punishment! He would not want to go through another hard caning again. That had hurt and was sore for days, but he would love to know what a slippering and a spanking felt like. He wondered whether he would pluck up the courage to broach the subject or whether he would be too bashful.

“I’ve just come along to see how you are getting along with the conservatory Derek.” said Gordon, “Any problems?”

“None whatsoever!” exclaimed Derek, “Even during that storm the other night not a drop of water came in!”

“Oh good! I pleased to hear it!”

“Have you got over the caning yet?” asked Derek with a twinkle in his eye.

Gordon was pleased that Derek had brought the subject up so soon.

“Ha! Sure! I have now. God, didn’t that hurt that night though!”

“I expect that just like a schoolboy the first thing you did when you got home was to go straight to a mirror!”

“Err, yes I did!” admitted Gordon as he coloured up slightly, “But I’m glad you’ve brought the subject up. There’s something I want to ask you!”

“Fire away! I’m all ears!”

“I’ve become interested in these old school punishments. Did you use any other corporal punishment other than the cane!”

“Oh yes! It depended on the severity of the offence. I used a slipper sometimes and occasionally spanked with my hand!”

“The slipper didn’t hurt anything like the cane I suppose?” asked Gordon hopefully.

“Not quite, but it did nonetheless carry a good sting. The main difference is that while the effects of the cane lasts for days the worst of the effects of the slipper can wear off after several minutes. I’m talking about a normal four to six strokes. If a slipper is applied relentlessly it can cause bruising just as the cane does!”

“I wouldn’t want to try your cane again but I’d love to find out what the slipper was like! Would you give me the slipper?”

Now Derek really was surprised. The boy had suggested and endured the caning for a good reason but now he was asking for another stinging bottom presumably for the fun of it!

“Are you serious?” asked Derek in amazement.

“Yes I am! I have got an urge to know just what boys had to put up with in those days!”

“My word! You weren’t put off by that caning then?”

“Not now that I’ve got over it!” said Gordon, “It was hell at the time but for the next two or three days when it was just sore and there was no stinging it was rather a nice feeling. I sort of felt proud to have gone through with it!”

Derek had long thought that the many boys he had caned might have left his study in agony but had come to regard their stripes as badges of honour! He would be only too pleased to oblige if Gordon was keen for more. he would love to see that youthful bottom bent across the seat of a chair once more!

“I haven’t got a real gym-shoe here,” said Derek, “but I’ve got a pair of those blue canvas ones with rubber soles. They are much the same thing! I’ll fetch one!”

Derek went out of the room and returned with a size eleven canvas top shoe.

“Are you sure you want to go through with this?”

“Absolutely!”

“Very well! Bend over the arm of that chair Grey!”

“Yes sir!” responded Gordon as he got across the arm.

The mere sight of that anatomically perfect rear end thrusting upwards and just crying out for attention was enough to arouse Derek’s physical as well as emotional feelings! How he would have loved to see that bottom bare, but perhaps that would be expecting too much! Trembling with excitement he raised the shoe and slammed it down upon the waiting buttocks.

Gordon was surprised as how mild the blow felt! What he did not know was that unlike the cane which produced an almost unbearable sting with the very first swipe, the pain from the slipper was to become more intense with each new wallop! The second whack produced a very noticeable sting! The third was beginning to convince him that the slipper was no toy! The sting was quite uncomfortable by this time. He wanted to shift the position of his bottom but managed to refrain from doing so in order not to reveal to Derek that it was hurting after only three! On the fourth stroke however he could not prevent himself giving a little waggle!

Derek smiled to himself, it was following a familiar pattern. Most boys would take the six and get up apparently unaffected, while in reality they were hoping to be released from the room immediately so that they could rub the affected area in private outside! Derek would deliberately keep talking to them until, in the case of nine out of ten of them, they could wait no longer to put a hand behind them! Gordon seemed to be behaving in the customary fashion!

Derek delivered the fifth stroke and the movement of the bottom became more pronounced! Then the final one crashed down.

“That’s it! That wasn’t too bad was it?” said Derek as his visitor rose rapidly to his feet.

“No, not really!” lied Gordon, trying to pretend that it did not hurt!

His right hand kept straying halfway round to his bottom before he realised what he was doing and he would withdrew it. Derek knew that it was now only a matter of thirty seconds or so before Gordon would be unable to resist giving a rub. He was right! With a sigh of relief his hand began to buff his stinging buttocks as if he was trying to polish them!

“That hurt more than you care to admit! didn’t it?” grinned Derek.

Gordon put on an expression which was half a smile and half a look of pain!

“Well yes! I didn’t think a slipper would sting that much!”

“At least you won’t have hours of pain and days of soreness!” Derek assured him, “It’ll probably sting like blazes for five minutes or so, but then, so some of my ex-pupils have told me, it developes into a nice warm glow like standing with your back to a roaring fire!”

“It’s beginning to feel like that already!” said Gordon with a note of enthusiasm in his voice, “It’s a great feeling!”

“It’s supposed to be a punishment!” laughed Derek, “You’re making it sound like a pleasure!”

“It is now!” replied Gordon, “It wasn’t while I was actually getting it though!”

Derek refrained from telling him that it had been a great pleasure giving it to him!

“May I come and see you again, Derek? I would love to complete the trio and sample a spanking some time!”

Derek’s heart was racing. He would certainly love to spank this boy and he was wondering if he dare mention giving it to him on his bare bottom! The truth was that at his school he never spanked boys over twelve. Once they had reached their teens it was always either the cane or the slipper! Up to age twelve he would put boys across his knee and spank them but he had never made a boy remove his trousers for punishment! But fortunately for him Gordon did not know that!

“Yes of course you may if you really want to try it. I must say you’re a glutton for punishment my boy! Actually when I spanked boys I used to make them remove their trousers and pants and then put them across my knee, but you would not want to do that of course!” said Derek hoping that in fact Gordon would want to do just that!

Gordon seemed somewhat astounded at first. He hesitated while he let the pronouncement sink in.

“I want to find out what it was like for real! If that’s the way you did it then that’s the way I want to try it!” said Gordon while wondering if he would regret committing himself to such undignified treatment!

Derek felt like rubbing his hands with glee, but did not do so of course! He feared that he might wake up in a minute or two to find that it was all a dream.

“If you’re sure then I shall be happy to accommodate you!” said Derek – in fact he would be over the moon! – “When are you thinking of coming again?”

“Hopefully early next week, but it’ll have to be in the evening, not during the working day. I can’t keep coming round to see how you are getting on with the conservatory!”

“No, I suppose not. How about Monday?”

“Suits me fine! About seven?”

“That’s fine with me!”

Gordon said his goodbyes and left. Derek wondered whether he could bear to wait for four days! He was actually going to put that handsome boy across his knee and smack his bare bottom! The mere thought would keep him supplied with erections until Monday he thought, as he headed for the bathroom to deal with one there and then!

On Monday Gordon arrived exactly on time. His visit was no longer during working hours so he had swapped his suit and shirt with tie for a pair of tight-fitting blue jeans and a T-shirt. Derek took him into he living room.

“Would you like a drink before we start?” asked Derek.

“That would be nice. It’ll steady my nerves!” replied Gordon.

“You’re nervous then?”

“A little!” grinned Gordon.

“Gin or whisky?”

“Oh! Whisky please with a little water.”

As he poured out the drink Derek looked towards Gordon who was standing sideways-on to him. What a fine figure he cut. The front of his body was dead straight from his shoulders to his feet and his back was equally straight except for that lovely curvy bulge half way down, enhanced by his tight jeans! Derek handed his guest the glass.

“Cheers!” said Derek, stopping himself just in time from saying “Bottoms up!”

The pair of them finished their drinks.

“I’m ready! I’m all yours!” said Gordon.

“Right! Get those jeans down Grey!” said Derek adopting his headmaster voice.

Gordon slowly dropped his jeans to his ankles. He was not wearing anything underneath them and his T-shirt only came down as far as the top of the crack of his bottom. It was all on display and it did not disappoint Derek. Two absolutely perfectly shaped buttocks greeted him!

“Come here, across my knee!”

Derek got hold of the boy and aided him over his lap. Did Gordon feel embarrassed and humiliated? Yes he did! Very much so! And he was enjoying it! He liked being embarrassed and humiliated! He even pushed his bottom up as high and taut as he could to make it even more attractive to Derek! Derek could hardly believe the sight before him! Never before had he had a boy across his lap with a bare bottom only inches below his eyes, and he could sense that Gordon was deliberately poking his bottom up. Derek too had something poking up but it was not his bottom! Now for the first time he was going to experience the feel of flesh slapping flesh!

SMACK-SMACK-SMACK!

Gordon’s bottom turned pink as it wobbled uneasily. Derek’s hand seemed to sting as much as the slipper did.

SMACK-SMACK-SMACK!

Derek was going to stop at six. He could see that the red squirming buttocks must be getting painful. Despite the intense sting Gordon was enjoying it! He wanted more!

“Don’t stop!” he called out, “Keep going!”

Derek was not unfamiliar with boys crying out in vain for him to stop but this was the first one had ask him to continue! It was a request he was not going to refuse! He landed another six hard spanks!

“Had enough?”

“Yes I think so!” responded Gordon.

The boy stood up and this time unashamedly rubbed his stinging cheeks!

“My goodness you can hit hard!” he said with a wry smile.

“It’s like riding a bike!” grinned Derek, “Once you can do it you never forget the technique!”

Gordon pulled up his jeans then continued the rubbing for a few moments.

“Sit down!” invited Derek, “I’m sure you could use another drink now!”

Selecting a soft comfortable armchair Gordon sat down. He was still feeling somewhat embarrassed after the undignified way he had presented his bare bottom to Derek.

“Thanks I’d love another drink.” said Gordon.

They chatted away as they sipped their drinks, talking almost exclusively about corporal punishment. Derek got the impression that Gordon was longing to either say something or ask something. After a while he came out with it.

“I want to ask you something Derek! May I keep coming to see you?”

That question was the icing on the cake for Derek! It was better than winning the lottery!

“Sure you may, Gordon! You want more?”

“More spanking like this evening! Once is enough for the cane and slipper. But I would love to come and see you regularly for a spanking over your knee with my trousers down! It hurts but it’s great fun! And afterwards,” – here Gordon glanced down at his crotch – “it err, sort of turns me on! I don’t suppose it affects you like that! It’s routine stuff for you isn’t it?”

Derek was thinking just how naive this lad must be if he thought that stinging his bottom was having no physical effect on his spanker! He smiled.

“I have noticed the bulge between your legs my boy! You obviously haven’t noticed that I am in a similar condition! You don’t think I would go to the trouble of giving you all these whackings if I wasn’t getting something out of it myself, do you?”

“Oh yes, of course!” replied Gordon turning a little red in the face.

“Now I’ll tell you something. You are a born bottom, meaning you enjoy getting it! I am a born top, I enjoy giving it! We’re like a nut and bolt! We fit each other! Let’s drink to that! Empty your glass Gordon and I’ll refill it. And let us seal our new partnership with a toast!”

Derek had by this time convinced himself that this was no dream. It was really happening! And he had also got the conservatory he had always wanted!

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Story ©MMIX by Skinpang.

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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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 Skinpang’s earlier story on The Canery can be found here. Further great stories by Skinpang may be found at this external link.