Strange Way To Arrange A Spanking Part III

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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 kaçak iddaa 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 kaçak bahis 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 illegal bahis 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.”

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