The twenty-year-old junior salesman slowly unclasped his belt and unbuttoned his trousers. He pushed them over his hips and let go. From there they slithered slowly down his legs.
A breeze from the nearby open window brushed against his naked legs as he awaited the next command.
Tyler looked over at his boss; in his hands was a wicked-looking school cane, around three feet in length and with a curved handle. Mr Davenport’s huge grin exposed his decaying teeth as he tapped a point on the floor in front of him with the cane, “Please bend over and touch your toes.”
Submissively, Tyler did as he was told. He rubbed his hands together, flexed the muscles in his arms, arched his back and stooped forward to present his buttocks for a thrashing. With his feet planted a yard apart and his legs straight, he was in the perfect position. His bottom was thrust up with only the thin material of his underpants between him and the cane. He felt like his arse was on offer, raised provocatively to his master.
Mr Davenport waited. There was no need to hurry. The longer this took the more he would enjoy it.
“You’ve been late for work too many times, lad. You take long lunches and, my God! your sales results this month are appalling,” Mr Davenport swished the cane through the air as he catalogued Tyler’s faults.
Bent double, with his fingertips touching his toes, Tyler was in no position to argue. It didn’t matter what he had to say in mitigation (in truth he had nothing, he was guilty as charged on all counts), his boss had already decided on his course of action. The young salesman had no real choice but to obey: for him it was the swish of cane or the unemployment line.
His bottom was thrust out backwards invitingly as he touched his toes, stretching the cotton underpants tight. Tyler’s hair fell forward untidily and his buttocks trembled nervously, making ripples in the fabric that betrayed his growing apprehension as he waited for the thrashing to begin.
Mr Davenport believed there was no point caning a boy unless it hurt, so he always caned on the bare buttocks. He set the cane down on his desk and approached Tyler from behind. In one swift movement he grasped the young man’s underpants at each hip and gently lowered them down his thighs until they rested precariously at his knees. One sharp move from Tyler would see them tumble down his shins to a final resting place at his feet.
The boss admired Tyler’s creamy white hairless buttocks. It was obvious he had recently shaved: back and front. The young salesman felt incredibly foolish, his bottom bared, offered for chastisement. He twitched in anticipation as his boss moved behind him. Surely, he was ready now? Why did he always play these games; making him wait, and wait, before cracking the first agonising stoke across his bum?
His boss’s cold hands rested on his tender mounds as he slowly pushed the tail of his jacket well clear of his target. He was a big man, physically fit. Tyler had been beaten by him before so knew how much it was going to hurt.
Nearly ready, the tip of Mr Davenport’s tongue licked his lips, as he flexed the cane and began tapping it gently on Tyler’s naked arse. Slowly he removed the cane and then lashed it down viciously into his naked haunches. Tyler gasped as the pain kicked in. That first searing stroke reminded him just why the cane was to be feared.
After a long pause, stroke two slashed down, slicing into his sore cheeks with real force. His arse throbbed and ached.
Swish-Crack! Mr Davenport whipped a third stroke down on the bare buttocks. The cheeks gave way as the cane sliced like a hot knife through butter.
Another stroke followed and landed just below the first. This time the young man gasped and felt tears coming into his eyes as the intense sting burned deep into his buttocks, The following strokes landed lower down before he could catch his breath another lashed right into his sit-spot where the cheeks met the thighs.
As he struggled for breath, Tyler felt the gentle (reassuring almost) touch of his boss’s hand on his back, just between his shoulder blades, this was before a further three strokes lashed across his bottom leaving him yelling and crying bitterly as Mr Davenport raised weal after weal across his sorry burning backside.
Mr Davenport was enjoying this. He adjusted his own trousers and raised the cane once more before whipping it down viciously. The noise of this stroke was incredible and resounded all around the small office.
Then there was an eerie silence, broken only by Tyler’s gulps and gasps for breath and his sobbing. Mr Davenport stepped back and looked at the boy still bent over, his buttocks quivering. “It’s over,” he said. “You can get up now.”
Tyler managed to raise himself up, the change of position made his arse hurt even more; how he wanted to rub it, but he knew his master never allowed that till you left the office. In severe pain he bent and pulled first his underpants and then his trousers up over his blistered cheeks. The touch of cloth on burning flesh reignited the agony in his buttocks.
“I think you have learned your lesson, haven’t you?” his boss asked rhetorically, but Tyler tried to gulp a reply. He knew this was his cue to leave. Brushing away tears from his eyes he thanked his punisher, turned and left the office. Once outside he gave his arse a much needed rub then hobbled off to the lockers to collect his belongings and go home; safe in the knowledge that he would get a pay cheque for at least one more month.
Mr Davenport pulled open his desk drawer and withdrew a box of tissues before ripping down the front of his trousers. He was stiff and aching and he came almost immediately.
Relaxing minutes later with a mug of fresh coffee, he recalled the first time he saw Tyler, four months ago at Whacko! a club for corporal punishment enthusiasts. Tyler and another lad just turned up out of the blue. They were dressed like schoolboys, in long grey trousers; white shirt, striped tie: they were obviously on the make. If they weren’t quite rent boys, they weren’t far off. Mr Davenport enjoyed Whacko! – you could do all kinds of things in the playrooms: canings, slipperings, beltings; but nothing too heavy. The only drawback was so many of the men were middle aged; you never had the chance to take a youngster across your knee for a bare-bottomed spanking or order them to, “Bend over and touch your toes.”
That night the club members drank their fill, including Mr Davenport. Tyler was most obliging. Mr Davenport could feel his penis rising at the memory of it: Tyler bent over his knees; head down, legs straightened behind him; his muscular buttocks perfectly positioned to feel the stinging slaps from the palm of his hand.
“You have the most magnificent arse,” Mr Davenport was breathless in his admiration. Tyler smiled inwardly: he had hooked another one.
He didn’t spank him hard; the arse was so glorious, it was enough for him to pat and preen it; to rub his palm over the smooth cotton of the boy’s tight white underpants and then down his thighs. Then over his strong back to the shoulders. But, yes eventually he did spank the arse, but not in anger; he loved the feeling as his hand connected with Tyler’s firm cheeks; they were meaty, but bouncy to the touch. Tyler was a fit lad, there wasn’t enough spare fat on him to fry a sausage; he was a spanker’s delight.
Mr Davenport’s appetite could not be satisfied; he wanted more. Tyler gave him his phone number, muttering something about “a private session,”, before heading off home with a very sore bum, but pockets bulging with cash.
Mr Davenport couldn’t get Tyler out of his mind, he dreamt of having him in every spanking position imaginable. He must see him again. It was easy to arrange; and Tyler was just as obliging in Mr Davenport’s apartment as at Whacko! Mr Davenport wasn’t really an over-the-knee man; the swishy school cane was his fantasy of choice and he had a fine collection hidden behind the wardrobe in his spare bedroom. Tyler played the stroppy teenager and when Mr Davenport made him pay with his arse Tyler made Mr Davenport pay from this wallet.
Mr Davenport was hooked, he wanted more and more; but with a divorced wife and two children he couldn’t afford it; that’s when he hatched a plan. He had once read a fantasy story in a magazine; why couldn’t he do it in real life?
They say that in life timing is everything: it certainly was for Mr Davenport. He struck lucky. Tyler had been jobless for ages, and now he had no home either. Relationships are complicated and Tyler had just found himself dumped for a younger model. But, one man’s meat is another man’s poison, and Mr Davenport was ready to pick up the option.
It was a fiendishly simple plan. Tyler was to work at the sales company Mr Davenport owned. He would be a junior salesman on the staff with a proper salary and when he screwed up; it would be sore-arse time. A fantasy made reality.
In truth, Mr Davenport thought it was a ludicrous idea and was astonished that Tyler signed up. But, it worked perfectly; Tyler had no discipline, could never get to work on time, often drifted home early, stayed out on long lunches and to cap it all, he was a truly abysmal salesman.
And from that day forward Mr Davenport owned Tyler’s arse.
Picture credit: Unknown
This story was first uploaded in October 2015.
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More stories from Charles Hamilton II are on the MMSA website
Charles Hamilton the Second