Lisa and Ms Maguire had a conversation about an upcoming tennis tournament as if it was perfectly normal to have a virtually naked Jimmy standing in the room with them. After the 10mins or so they called him back to the desk. The heat from his bottom was immense and he could already feel the bruising as he walked back but he had managed to regain some composure.
“Right”, said Lisa, “Jimmy go fetch the cane”
Jimmy made his way back to box, there were actually a number of canes he realised and although he had never been on the receiving end he had heard about differences between light nursery canes versus the much heavier and severe senior cane. He spotted the smallest one in the bunch and picked it out hoping that Lisa would not notice anything different.
Taking a deep breath, Jimmy turned and made the walk back.
“I’m sorry for spying on you and playing with myself. Please use this cane on my bare bum to help me improve”
Lisa took the cane and started to swish it through the air.
She then swung it back and hit the back of the closest chair which was covered in a soft fabric. Jimmy stared in horror at the definite indentation and line that was left on the chair and imagined what it was going to feel like against his bare cheeks.
Lisa looked at the chair and grinned, “I think this should definitely help improve his behaviour Miss” She was really growing into her role as the disciplinarian and was enjoying it far too much for Jimmys liking.
“Bend over young man, you are about to get six of the best!” Lisa said in as deep as voice as she could manage trying to impersonate a Headmaster. She then laughed at her own joke.
Jimmy assumed his position again and Lisa took up a position next to his left hip.
“Tap, Tap, Tap, Tap”
Lisa tapped the cane off Jimmys bum cheeks trying to line up whereabouts she wanted to stike.
“You want to try get some strokes down low on his cheeks here now Lisa” said Ms Maguire “Try aim for the spot just where his bum cheeks meet the top of his thighs, that way he will definitely feel it when it sits down for the next few days!”
Lisa stood back with a look of concentration on her face. “I think his bum is down too low Miss, I don’t think I can get low enough to hit that spot”.
“Have a go and see”
“SWISH”….”Crack!”
The cane crashed into Jimmy’s bum but missed Lisa’s intended spot completely and impacted practically at the top of Jimmys cheeks.
“Oh dear, that is too high” said Ms Maguire “we do need to be careful with the cane, don’t want to injure Jimmy now do we. Let me give him one stroke and I will demonstrate”
“SWISH”…”Crack!”….”OWWW”
“OK that was better I think but not perfect” said Ms Maguire but I think you are right, his bum is too low and makes it hard to get the right spot.
Meanwhile Jimmy was thinking these last 2 strokes were doing more than enough damage as the pain burned through his bum and seemed to keep going. Then his heart skipped a beat as he heard Ms Maguire ask..
“Lisa, was this the only cane in the box ? It seems a little light for a senor cane”
“There are a few canes Miss, not sure what the difference is.”
“SWISH”…..”CRACK”
The cane struck Jimmy right across the center of his bum. “I think Jimmy has tried to pull a fast one here and get off lightly!!”
“SWISH”….”CRACK!”
Another searing line of pain swept over his bum. “Well luckily we have detected it and so these strokes we can treat as just practice until we get the proper cane”
She handed the cane back to Lisa saying “I think I have an idea which might help. Stand up young man and put yourself back in the corner right now!”
Jimmy made his way to the corner and waited nervously as he heard some of the furniture being moved – he wondered what plan was being hatched back at the desk. After a few mins he was called from the corner.
“Get back over here, young man!”
Jimmy turned and walked back towards the desk. There were now 2 small stools placed in front of the desk about 2-3ft apart. Jimmy was confused.
“OK” said Ms Maguire with a very pleased look on her face. “I think we have sorted the problem! You will stand with one foot on each of these stools so your legs are spread wide apart. Then I want you to bend right over, legs straight and get your elbows down on the desk. Come along, get on with it.”
Jimmy cautiously stood up on the stools which were about 8in high and saw that the desk top was now just above his knees. He began to bend over to get his elbows down onto the desk he realised with terror the effect this change in position was going to have. His head and shoulders were now lower than his hips which meant his bum was right up in the air and with his legs spread wide he knew everything was on show.
“Ohh, much better” Lisa almost squealed with excitement as she inspected her new target. “I can even see his balls and cock through his legs and I can use his bum-hole as my target she exclaimed”
“Have a go now Lisa and see if this new position helps your aim, remember these are still just practice strokes until we get the proper cane!”
SWISH!…..CRACK!
The cane landed just above the crease at the lower part of his cheeks causing an immediate straight red mark to appear – the appearance of the mark on his bum was accompanied by a yelp from Jimmy as the cane cut into him. Lisa looked on in delight at the sight of his cock jiggling around as he tried to flex his bum to ease the pain. She liked this new view!
“That was perfect Lisa – I think we are ready to start the real caning. Stand up boy, you know the drill, go fetch the cane and this time you better ensure it is the heaviest one available in that box!”
Jimmy made the walk back to the box once more. Looking at the canes it was pretty obvious which one was the “senior” cane as it was significantly thicker than the others. He reluctantly pulled it from the box and as before walked back to Lisa presenting as if it was a most precious gift.
“I apologise for trying to spy on you earlier and also for playing with myself. I’m also sorry for trying to trick you with the other cane. Please now accept this senior cane and use it on my bare bottom to help me behave better”
It was the first time Jimmy had actually looked Lisa in the eye during his apologies. It was also the first time he realised he meant what he said, he was sorry! He got a strange contented feeling as he stepped back up on the 2 small stools with his legs spread wide apart, bending over in full knowledge that his most private parts were on full display and the most tender spot on his already well bruised and striped bare bum were presented as a perfect target. In a strange way he wanted Lisa to use that cane to the best of her ability and he willingly bent over as far as he could manage and stuck his bum out. He felt the familiar twitch in his cock as the first of the six strokes landed right on his sit spot! He savoured the sensation as the pain spread through this bum and down his legs causing him to quiver all over.
SWISH … CRACK!
The final stroke landed perfectly across his lower bum cheeks and Jimmys body jerked one last time as he started taking deep breaths.
“Well done indeed Lisa” said Ms Maguire as they both stood back to assess their work. Jimmy’s cheeks were various shades from red to deep purple along with some white lines where the welts had started to appear. “I think that is a well spanked bottom, he will remember and feel this for the next week or more and maybe will be better behaved in future ”
Lisa felt for sure she would be remembering this also for a long time to come, she had not failed to notice the twitching of Jimmy’s cock and she could feel her own panties getting slightly damp.
“I will tidy these things away, I think we are done here and we can consider the matter closed” said Ms Maguire as she headed for the back of the room.
Lisa looked at Jimmy who was still in position and recovering his composure. She reached out and touched his bum with her bare hand. As she ran her hand over both cheeks she was surprised at the heat coming off, Jimmy squirmed a little as she touched the most tender welts but her cool hand was welcome and causing him to be excited. Lisa slowly traced her fingertips down his crack continuing through his legs gently cupping his balls while reaching around with the other hand and giving his erect cock a few teasing strokes.
“I hope you’ve learned your lesson today!” she said with a giggle as she withdrew her hands and gave him one more spank on each cheek. “Get your pants and underpants back on and go get cleaned up!”
Jimmy slowly eased on his underpants which felt much tighter on his swollen bum and pulled on his pants. He made his way to the nearest bathroom to wash his face and also get his first view of his well punished rear in the mirror.
A few mins later he came out and headed for the exit door, thankful to finally be going home and looking forward to getting some soothing cream on his bum but also relieving the pressure that had been building in his cock!
“Hey Jimmy!”
Jimmy looked up to see Lisa standing facing him ahead in the corridor.
“No hard feelings right? You got what you deserved.”
“Yeah – I guess so” said Jimmy smiling slightly
“Look I feel kinda bad so wanted to give you one thing before you go, thought you might like to keep these as a souvenir!” and she tossed him her white tennis panties she had been wearing earlier.
Jimmy picked them up and once again felt his cock start to rise to attention.
“You know you probably wouldn’t have seen much through that dirty window anyway, it was too far away and in the end I was the one who got the best view of a cute bum today! But all is not lost for you…”
With that she turned her back to him, then leaned forward slightly, stuck her bum out and flipped up the back of her tennis skirt. Jimmy couldn’t believe it her panties which she had been wearing were now in his hand and he had a full view of her perfect bare bum. Then still giggling she spread her legs and showing her flexibility bent right over to grab her ankles while looking back at him grinning through her legs. Her immaculately groomed pussy and bum now on full display pretty much mimicking the position Jimmy had been in earlier himself.
“Thought it was only fair to give you a sneak peek given all the trouble you’ve been through” she laughed. “hope you enjoy the view as much as I did of you”. “But don’t go telling anyone about how naughty I’ve been or it could be my bum on the receiving end of the cane next time!” with that she jumped up and skipped off “see you around!” she called.
Jimmy could not contain it any longer as he felt his cock pump uncontrollably into his underpants!
Source: reddit.com/r/eroticliterature/comments/oeiocl/peeping_tom_gets_his_due_reward_ffm_spanking_pt_4