“Ok, then let us get this over with” said Ms Maguire as she picked up the ruler from the desk.
“Bend over the desk”
“Smack!, Smack!, Smack!”
Jimmy felt the 3 strokes with the ruler but in all honesty his trousers provided a good padding and so he wasn’t overly worried…
“Excuse me miss” interrupted Lisa, “I think it is not fair that Jimmy got to see me in my underwear but he now gets to keep his trousers on for his punishment. Maybe he should be punished in his underwear so I get to see him, you know like, same as he did me!”
Jimmy’s heart quickened…this was not sounding like a good idea to him.
“That is a fair point Lisa, I agree and in any case I think this ruler is very light I’m not sure it is having much effect. Stand up young man and pull your trousers down…all the way now, I want to see them at your ankles.”
Reluctantly Jimmy undid his belt and lowered his trousers, he was ordered back over the desk and this time his bottom was presented to the ruler covered by just his white cotton underpants.
“Smack!, Smack!, Smack!”
3 more strikes, starting to sting a bit now thought Jimmy but he was thinking it must be nearly done and he could go home.
There was a pause in the strikes, “I don’t think this is working Lisa. This ruler is not having any effect I fear, it is much too light I believe”
“Maybe we need to check his bum colour miss” said Lisa in a mischievous tone…”that way we can see for sure if the ruler is having an effect!”
“That is an excellent idea Lisa. I think a bare bum will help us know if we are getting the message across or if we are missing some parts! Stand up and drop your underpants right now.”
“You cant make me do that!” said Jimmy in a panic
“Don’t argue with me, you agreed to this punishment. Remember you were attempting to spy on Lisa – you would have been more than happy to see her bare bum and private parts if I hadn’t found you! You either do what you are told or we call the Police”
Knowing he didn’t have much choice at this point Jimmy lowered his underpants, he tried to stay as close to the desk as possible to try hide his cock but he still felt his face flush deep red with embarrassment knowing his bare bottom was now on show and there was nothing he could do about it.
“Seems like the cheeks of his face have turned a brighter shade of red than his bum cheeks!” laughed Lisa noting his embarrassment.
“I agree” said Ms Maguire as she pulled Jimmys t-shirt right up his back to ensure it wasn’t covering any part of his bottom, then smacked the ruler 3 more times across the bare cheeks. “This ruler is just not doing the job – I’m sure the old headmaster must have had something more significant in this office for dealing with unruly offenders. Lisa, can you check some of the cupboards and see if there is anything there which has been stored away”
Jimmy felt his heart sink a bit, while he never experienced it himself he had heard old stories of people leaving the headmasters office with very sore bottoms indeed when corporal punishment had been a standard part of the school rules. He hoped any implements had been long discarded.
Jimmy remained over the desk as he heard Lisa opening different doors and cupboards, after a few mins she called out from the back of the room.
“I think there is a box of stuff here, Miss!” “It’s a little bit dusty but I think it is what we are looking for”
“Tell me, what have you found ?”
“Well this looks sort of like a large wooden hairbrush but it doesnt have any bristles on it”
“Oh good, that sounds like a spanking paddle – excellent” said Ms Maguire “That will come in useful – much better than this ruler”
“There is also an old leather belt it seems, doesn’t have any buckle and seems to be split in 2 at one end”
“A lochgelly strap! It’s supposed to be look like that Lisa, the split is called the tails which definitely get a message across. That is not a belt for holding up trousers but it is very effective doing other things around the bottom area if you get my meaning” said Ms Maguire with a chuckle. Jimmy listened on in dread the more he heard the more worried he became.
“And finally” said Lisa “I’ve heard about these – there are a few canes!”. “Can we use them on him … please ?”
“I think we have finally got what we need” said Ms Maguire. “These definitely would have been used by the headmaster long ago to discipline boys who misbehaved and I think we have such a boy here now so this is perfect”
“Now I wonder given your dreadful behaviour which one is the best option. What do you think Jimmy ? Would you have got the paddle ? Or maybe the headmaster might have considered the cane or the strap more appropriate…”
Jimmy was now genuinely afraid of what was coming and all he could manage was “I don’t know Miss”
“I know Miss! We should try all of them!” piped up Lisa, “that way we can be sure he has been punished with the correct one” she added with a little more enthusiasm than Jimmy would have liked to hear.
“Well that is an excellent idea, don’t you agree Jimmy”
Jimmy wasn’t sure if he was supposed to answer but he couldn’t muster one, he just felt things were now getting out of his control completely and he was at their mercy.
“Ok, I have the perfect plan” said Ms Maguire “Lisa, please leave all of those in the box at the end of the room for the moment and come back here”
“Ok” said Lisa sounding disappointed.
Source: reddit.com/r/eroticliterature/comments/oeiezr/peeping_tom_gets_his_due_reward_ffm_spanking_pt_2