Strange Way to Arrange a Spanking Ch. 03

I answered the phone. "Headmaster, it is the housemistress here. Sophie Finn has simply gone too far this time. You need to punish her and punish her severely; I suggest a bare bottom caning at the very least."

It was Sophie on the phone, up to her old tricks again. I had heard her come into the house ten minutes earlier but had not had the chance to pop down and say hello.

"What has she done that is so bad?"

"I think it would be better if she told you herself, can I send her up to see you?"

"Yes, send her straight up. Let us sort this out."

It looked like my quiet morning catching up on paperwork was out of the window. But paperwork will always lose when there are bottoms to punish.

There was a timid knock on the door.

"Enter."

Sophie came into the room, dressed as a classic adult schoolgirl. She was wearing a very short skirt that stopped above her stocking tops, on her feet were high heel shoes and she had on a blouse that revealed far more than it should. Needless to say, she looked stunning.

"Headmaster, the housemistress sent me."

"For what reason are you here, what have you done?"

"It is embarrassing sir; I would rather not say."

"I do not think you have a choice, what have you been doing, come on out with it girl." I used my best strict headmaster voice.

"I have been letting boys look up my skirt."

"Anything else?"

"I have been charging them money if they wanted to touch me."

"I see, anything else."

"The Housemistress said to show you this." With this, she took her hand from behind her back and placed a buttplug with a pink jewel on its base on my desk. From her other hand, she revealed a tube of lube.

I decided to play dumb at this point. "What is that?"

"It is a plug, sir."

"What sort of plug?"

"A buttplug."

"Please explain the use of such a thing."

"If the boys pay me enough money, I put the plug up my bottom, sir"

"The boys paid you to do this?"

"It is the most expensive thing on the menu, sir." Sophie gave a cheeky smile at the comment.

I stood and walked around my desk. "You could be expelled from the school for this, you know that Sophie, don't you?"

"Yes sir, sorry sir."

"What am I to do with you? It will have to be a very severe punishment."

"Detentions, sir. I hate those."

"Sophie this thing is far beyond detentions. I think I will have to whip your bottom and then cane you. I never want you to ever think of doing anything like this again."

"But lots of girls do it to earn extra money."

"I doubt that Sophie, perhaps you could show them your bottom when we are finished so they know what to expect if they get caught."

"I will want you bent over the desk for your whipping. I want you to stay still and not move around during your punishment."

"Sir, will it hurt?"

"Yes, Sophie I am afraid so, this has to be a punishment spanking,"

"I really will not be able to stay still, what can we do sir, can you secure me in some way?"

"Sophie, are you asking me to tie you up?"

"If you think it will help with my punishment sir," the small smile was back on Sophie's face, she knew exactly what she was asking for.

"Right Sophie, bend over."

She lowered herself beautifully over the desk, and once in position flipped her skirt up to reveal her knickered bottom. Her knickers were crotchless, and she was displaying herself in a most provocative way.

"What are those knickers you are wearing Sophie?"

"All the boys like them, sir. Do you like what you see?"

"You are very attractive Sophie, but that is not the point here. You are here to be punished and those are not regulation knickers. You seem intent on increasing your punishment at every turn. Let's have those knickers off and then get back into position."

Sophie stood slowly and then turned very provocatively and removed her panties, bending right over she looked at me and said, "enjoying the view, sir?" Then she dropped the knickers on my desk. I picked them up and put them in my top drawer.

"I will confiscate these until the end of term. They have no place in this school."

"But Sir, they are my boyfriend's favourites."

"He will have to await the end of term. Now Sophie in position."

Once she was settled again, I said, "I need to find something to secure you with, stay there and keep still."

I went to the 'toy box' and found some red leather cuffs and some short lengths of rope. I knelt behind Sophie and looked up to see her beautiful bottom and charms perfectly presented for her upcoming punishment. I noticed that she was in a state of sexual excitement. I put the ankle cuffs in place and secured them to the desk legs. "That should ensure that you stay in position during your punishment, do you wish me to secure your hands?"

"No sir that should be okay. Are you going to be very strict?"

"Yes, Sophie I have to make an example of you and encourage you never to do this again."

I went back to the 'toy box' and found my short leather whip, it has a leather handle and perhaps fifteen or twenty leather cords attached. It does sting and the leather cords can find their way into some very intimate places. I also found the cane I was intending to use. I placed both of the items on the desk in front of Sophie.

"I will start with the leather whip; it will prepare your bottom nicely for the cane. I think we need a severe caning. How many strokes do you feel would suffice?"

"Maybe six sir, I am very sorry."

"Six will not even begin to suffice this time. Think again."

"Nine should be more than enough."

"I think you misunderstand how serious this is, let's say fifteen strokes on your bare bottom. That should encourage you to change your behaviour."

"Sir, that is so many, you are such a meanie." That statement came with a Sophie grin that said to me she was enjoying this whole roleplay immensely.

"Right let us start, I find the whip with its many tails does warm a girl up nicely and it should certainly give you much to think about. Three from each side I think."

I stood to her left side and trail the tails of the whip over her bottom this drew a soft moan from Sophie, and she lifted herself higher.

I drew back the whip and brought it down at the junction of thigh and bottom. The tails of the whip could find interesting places to do their work. The stroke was not hard but did make Sophie shake very nicely. "Oh, sir that hurts."

"I think you will find that is the general idea here. Now prepare for the second

stroke."

The second stroke got a similar reaction. The third stroke I placed at the top of her thigh, this allowed the whiptails to wrap into her inner thighs. Again, a noisy reaction from Sophie and she tried to close her legs and was prevented from doing so as she was secured.

"Let's do that again from the other side."

"Sir do you have to. It is very painful."

"You should have thought of that when you were letting the boys have their wicked way with you."

"It was only fun."

"Well, it is not so funny now. Next three coming up."

I repeated the strokes from the other side. With much bottom wriggling, moaning, and drawing of breath from Sophie. Afterwards, the tops of her thighs had faint red lines where the whip had left its calling card. Her bottom looked like a picture.

I stood back to admire the view. Sophie was pushing her bottom out, legs widely spread with her stockings and black stilettos in place. To me, she looked so sexy and so inviting. I picked up the cane.

"Fifteen strokes Sophie, I will start with the first six then give you a break. I want you to be brave and think about the reasons you find yourself in this position."

I tapped the cane on her lower bottom. I delivered the first stroke on the overhang of her bottom where the whip had previously worked its magic. Again, it was not a hard stroke, enough to get Sophie on her toes and she shook her bottom before settling back awaiting stroke number two.

I proceeded to deliver all the initial six strokes and Sophie's bottom was decorated with six stripes to show where the cane had been. I put the cane back on the desk and knelt behind Sophie. She looked around and asked. "Sir, what are you doing?"

"I am inspecting the damage."

I gently traced the lines with my finger and then gently stroked her pussy, this got a reaction as she pushed back on my fingers. I gently teased her secret button and asked. "Is this what the boys did to you?"

"They wanted to but I would not let them."

"Do you want me to?"

"Yes, please sir, very much."

"Would you like me to use my tongue down there?"

"Oh sir, yes please, it will take the sting away."

I knelt behind her and ran my finger along her slit and Sophie pushed back and moaned with pleasure. I then started to lick and kiss her, and Sophie was soon really pushing herself onto me. She was very wet and was in a state of high arousal. I teased her with my tongue trying to keep her excited but not so excited that she reached her orgasm. After ten minutes of this, Sophie said. "Please sir, will you allow me to come? I am so ready."

"Of course, Sophie if that is what you want." I focussed on Sophie's clitoris and gently ran a finger around her rear passage. She soon found her peak and cried out and collapsed onto the desk. I slowly parted her buttocks and kissed and licked her anus. After a few minutes, I said. "We need to get back to your punishment, you need something to bring your mind back. I think we should insert that plug of which you are so fond."

"But sir it is very big for my small opening. It hurts, sir." Her smile as she said this certainly did not match the words.

"Sophie you need something to make you focus. Let's put plenty of lube on this plug and make sure it fits properly."

I coated the plug and gently pushed at her rear opening, there was a slight resistance and then the plug was fully inserted. "Oh sir, that is so big. My poor bottom."

"If this falls out during the rest of your punishment, we will start all over. Is that clear?"

"Yes sir, you are so very masterful today."

"Right let's proceed. Six strokes have been delivered. Nine to go."

I tapped her bottom just below the plug and delivered the next stroke. Sophie's breath whooshed out of her, and she waved her bottom from side to side before settling back down. The rest of the caning proceeded in a similar vein. After the last stroke, her bottom was decorated with fifteen red lines, a couple of the strokes had overlapped but overall, I was pleased with the result. "That is a very well punished bottom, Sophie, I hope we will not have to do this again."

"I am sure sir will find some excuse. It does feel like a very punished bottom."

Sophie looked around, she looked at the bulge in the front of my trousers, "someone enjoyed that immensely I see."

"They did yes, would you like me to take your mind off your punished bottom?"

"Yes please, sir."

I removed the plug from her bottom, and undressing I presented myself at the entrance to Sophies pussy, she was very wet and pushed herself back on me. We were both in a state of high excitement and both thoroughly enjoyed the next few minutes before both climaxing at the same time.

"Now let that be a lesson to you."

"Yes, sir," she said with her smile in place.

I knelt and released her ankles. She stood and we had a hug and a kiss for a few minutes before, Sophie said she would clean herself up and see me downstairs.

I made coffee and waited for her to come down. We chatted about what we had just been doing and both agreed we had a lovely time.

Sophie asked if I was around on Saturday afternoon, as she was free herself. I confirmed that I was, and we made a date for four o'clock.

As Sophie was leaving, she said. "Headmaster, the school inspector is coming tomorrow, and she has heard some very disturbing reports about your behaviour. The inspector wishes to see you on a Saturday to see if something other than your dismissal can be arranged. You are in big trouble and you have a very tough interview coming up."

Sophie kissed me on the cheek and left closing the door behind her.

***

Sophie arrived just before four o'clock on Saturday, after a quick peck on the cheek she said she would see me in the office in ten minutes, she disappeared upstairs carrying an overnight bag. I was as usual in two minds very excited and very nervous; I had a feeling that Sophie really meant business this time.

After exactly fifteen minutes I knocked on the office door. "Enter," came a very strict-sounding Sophie. She was sitting at my desk, in her headmistress gown looking very elegant.

"Headmaster I am glad you are here. Thank you for letting me use your office today, we have some very serious matters to discuss. Come stand in front of the desk."

"The school you run is performing badly, failing in the league tables and failing to maintain student discipline. This situation is being blamed on you. You have a choice, resign or be punished."

"How should I be punished?"

"I believe in traditional methods; in fact, I believe strongly in corporal punishment. It really does achieve excellent results."

"You want to spank me?"

"No, not spank you, I want to cane you and give you something rather special to help you remember."

"You want to cane me? Or I resign."

"That is the choice yes. Twelve of the very best on your bare bottom plus four specials or you leave. Your choice. What will it be?"

"I have to keep my job. I will be punished."

"Good before we start can you help me, what are these?" Using a pen, she lifted the crotchless knickers she had worn yesterday out of my top drawer. "They smell like they have recently been worn by a very aroused woman, what are they doing in your office?"

"I confiscated them from a pupil."

"You keep confiscated items in your drawer, I do not think so. This is a souvenir and shows the type of establishment you run here. We will increase the punishment to fifteen strokes and five specials. Now naked if you please and bend over the desk. I will get the punishment instruments."

Sophie stood and her gown parted to reveal her corset below, she as usual looked gorgeous, very strict but gorgeous. I slowly undressed and folded my clothes neatly and turned to position myself across the desk. Sophie had placed the senior cane and the riding crop we had recently purchased on the left-hand side ready for use.

"Come on headmaster I have not got all day. Get yourself bent over."

I positioned myself as instructed.

"Legs open please and keep your bottom nice and high please keep your bottom still. I need a steady target. Failure to comply with these instructions will increase the punishment. Ready?"

"Yes."

"You will call me Mistress."

"Yes, Mistress."

"That is better. Let's get this unpleasant task over with."

She did not sound like this was an unpleasant task at all. Although I was pretty certain I had an unpleasant few minutes ahead of me.

"The first one coming up, no need to count. I will remember, if I forget we can always count the stripes."

She tapped my bottom and a very hard stroke followed, I raised myself onto my toes and shook my bottom whilst letting out a small cry.

"Remember to keep still. No more of this silliness."

The second and third strokes quickly followed. Sophie then announced, "Oh I forgot." She went to her handbag and removed her latex gloves. "I do like to wear these when punishing someone. They do look purpose-made for this task."

She returned to her position and ran a finger along one of my stripes. "That does look sore, is it?"

"Yes, Mistress."

"Good, it is working then."

"Right the first of your specials coming up. Reach behind you and hold your buttocks open for me."

I did as I was told.

"No pull your cheeks wider apart, my crop needs a good target."

I pulled my bottom even further apart. I was totally exposed. Sophie picked up the riding crop and swished it through the air a couple of times. "Right one stroke with this onto your bottom hole. Keep your buttocks wide apart or it will not count."

Sophie came round the desk and standing next to my head she leaned over and delivered the stroke landing the leather tab of the riding crop directly onto my anus. It produced instant tears in my eyes.

"That will give you something to remember. On with the caning."

The next three strokes followed, and I was really struggling to cope. Sophie was certainly using more force than previously.

"Next special coming up, hold your buttocks again."

The procedure was repeated, and tears started to run down my face.

I endured three more strokes and the next special as Sophie called it.

Sophie said, "Right, I will give you a short break. Only six more strokes. Look forward do not under any circumstances look round. Understand?"

"Yes, Mistress."

I heard Sophie moving around behind me. I had no idea what she was up to, but I was very glad of the break. My bottom was on fire.

Sophie walked around the front of the desk and sat down. She had removed her gown and was dressed in her corset, stockings, and boots. The thing that took most of my attention however was that Sophie was wearing a strap-on with a black penis around six inches long attached.

"Do you know what this is?"

"Yes."

"Good, I do not intend to use this today, but if you do not keep still or we find ourselves in this position again this is what awaits."

It is hard to describe my feelings at this point. Fear, yes, excitement, yes, shame, yes, lust, yes. I had never seen a strap-on closeup, it looked very scary but there was something exciting there too. Did I want to experience this, I did not honestly know. My penis reacted positively to the situation, but it is probably not a good idea to think too much into that.

"Right, you have six more strokes and two more specials."

Sophie walked around behind me and delivered the next stroke, I looked around, and she looked wonderful. A beautiful dominant woman, wielding a cane with her strap-on ready. I managed to keep still for the next three strokes and the special. It took all of my self-control.

Sophie sat down again and took a tube of lube from her handbag. She squeezed some onto her hand and applied it to her penis. Stroking herself slowly she asked. "Are you enjoying the show?"

"Yes, Mistress it is very exciting." I was being totally honest it was.

"Final part coming up. Stay in position at the end."

Again, I just managed to keep still and then hold my buttocks open for the very painful visit of the leather tab.

Sophie walked behind me. "Hold your buttocks open again."

I looked around; she was stood directly behind me with her strap-on standing proud. She looked beautiful, scary but beautiful.

I hesitated but slowly complied with her instructions.

She took hold of her penis and ever so gently pushed at my rear passage. "Next time, headmaster you will get the full experience."

She pushed forward again, and I felt my anus start to open before Sophie stepped away.

Stroking my very sore bottom Sophie asked. "Would you like some of my cold cream to help take away the sting?"

"Oh, yes please, Mistress."

She led me into the bedroom and ever so gently applied the cream, all over the worst affected areas. It was a lovely feeling. She teased and played with me. At one point she inserted her whole finger in my bottom. "This is just a taste of what is to come."

***

Later that evening we ordered a takeaway to be delivered. I have read many times of people saying they did not want to sit down after been punished, I finally knew what they meant. It was an uncomfortable meal.

Sophie spent the night and for the rest of our time together we behaved like a normal couple. It was wonderful.

Sophie had to leave early the next morning leaving me to have a leisurely morning. Later that day in the office I found a buttplug with a blue jewel in its base placed on my desk with a sticky note saying.