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Strange Way to Arrange a Spanking

"A maid earns a spanking and then turns the tables."

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5.5k words 5.5k words

Author's Notes

"This is my first story. Pure fantasy. <p> [ADVERT] </p>Constructive feedback is welcomed."

I own a successful training company specializing in courses for large Blue-Chip enterprises. The job excites me, always has, and I get to spend the majority of my time traveling. I also get the benefit of being able to work from home. The workweek is typical, Monday through Friday, nothing out of the ordinary, so I look for ways to spice it up, so to speak. That is where my passion for corporal punishment comes in. I have collected CP magazines and DVDs for years, and more recently downloaded much material from the internet. I have a nice collection of punishment instruments and other items collected over time. The toy collection as I like to refer to it.

I like to keep myself fit, spend a lot of time outdoors in the countryside around my Dorset home. I am single by choice and although now in my fifties I look good for my age (even if I say so myself).

I am a neat and tidy person, but like most people, I do not enjoy housework. As the business is doing well, I decided to hire someone to clean and tidy the house and really to do the jobs that I can never seem to find either the time or the energy for. This is quite a step for me as I am by nature quite a private person, but it is amazing what you will do to get out of housework.

So, having decided to get someone to help around the house I advertised on the notice board in the local shop to see if anyone was interested. I got several e-mail responses but only one interested me. She explained that her kids went to the local middle school so she was looking for work that would allow her to drop off the kids and have some flexibility around hours. She could then balance work, life, and the school activities her kids got involved in. The whole tone of the e-mail was light and friendly, and I felt it would be worth at least having a chat. She had given me a mobile number to call her on and after a few minutes of reflection, I made the call.

Sophie Finn answered her phone and we immediately struck up a friendly conversation. In my experience, you know early on if you are going to be able to get on with someone, and in this case, that person would be working in my house sometimes alone. Trust and confidence are therefore essential. At the end of the call, we agreed she would drop round for a coffee after the school run the next day and we could take it from there.

The doorbell rang promptly at nine-thirty the next morning. I opened the door to see a woman in her early to mid-forties. She looked a nice and shapely woman, even though she did look a bit nervous again the first impression was this was someone I would like and would be happy to employ. We had coffee and biscuits and after the usual small talk, we agreed that we would give each other a trial of a month to see how it goes. The plan was that she would work three mornings a week on Monday, Wednesday, and Friday although I was flexible with the days in case anything cropped up on the family front. We agreed she would start the following Monday and I felt good about the situation.

Monday rolled around as usual and Sophie arrived on time, eager to start. I gave her a quick tour of the house; it is a three-bedroom detached house so this did not take long. I showed her where everything was kept and explained all that I thought was required. I keep all my CP magazines etc in a chest in the cupboard in my office so I did tell Sophie that as far as the office was concerned just vacuum the floor and keep the surfaces dust-free, everything else related to my work and she should leave well alone. I hoped this would avoid her seeing anything she should not.

For the next couple of weeks, I was working full-time from home. We chatted each day and conversation was easy and we started to relax in each other’s company. We shared a mid-morning coffee which gave us a chance to get to know each other better. I found that she had separated from her husband just over a year ago, he had left her for a younger model as she put it. Although he paid his way with the kids, she needed to work to pay for the little extras that we all need.

In the third week, I was going to be away on Wednesday and so I gave Sophie a key and was quite relaxed about leaving her alone in the house. When I got home late on Thursday all seemed well. Work was picking up and I was regularly away, so I did see less of Sophie, but we did leave each other sticky notes of updates and news. These notes did start to have a lot of banter and humour. As I say we did seem to get on.

This was the situation for a couple of months, Sophie and I agreed the trial period worked for us both, and then I did start to notice that in my toy chest (as I like to call it), things were not as I had left them. I started to take pictures on my phone before closing the box and then checking again when I got back from a trip. Someone had been looking in the chest. This presented me with a problem. What should I do? Have it out with Sophie? Or simply ignore the situation?

When we met, we still got on well and nothing seemed to have changed. This helped me to decide what the best course of action was to be. I remembered reading a spanking story of a maid who had gone against her master’s instructions and had been punished as a result. I printed this story out and laid it on the top of the things in the toy chest with a sticky note saying I thought you may like this story. What do you think? I left this on the Tuesday before being away on Wednesday and then returning home late on Thursday.

Whilst I was away my emotions swung all over. Was I crazy leaving the story, would Sophie leave and tell everyone about my obsession, would she be offended? It did seem like an exceptionally long two days. When I did finally get home, I rushed into the office and nervously opened the chest wondering what if anything I would find.

I lifted the lid and found a sticky note saying. Great Story. The Maid did deserve her punishment. Her boss had made the rules clear and she had broken them. Then she had drawn a smiley face.

The next day Sophie and I stopped for coffee in the morning and carefully avoided any mention of the story, the box, or sticky notes.

On my next trip away, I printed another similar story and again left a sticky note this time saying. I agree the maid should be punished for breaking the rules, what punishment does a naughty maid deserve in your opinion?

For the days away I was still nervous but this time probably more excited by what reply I would find when I returned home. Again, as soon as I got home, I rushed into the office opened the chest, and read Sophie's reply. It seems the maids in your stories always get the cane. Is that the punishment that would fit the crime?

I should probably say here about my views on spanking and women, I have read hundreds of stories and watched many, many videos. I think spanking should always take place between consenting adults and should be for the enjoyment of both parties. The anticipation, the build-up, and role-play all play a big part in the enjoyment of the situation. Although punishment should hurt, in no way should anyone be left with stripes that last for days or be unable to sit comfortably. In other words, spanking should be fun for all parties. If you look at any pornography you would believe that almost every woman in the world is slim and in possession of a perfect figure. Do not get me wrong these women are beautiful, but so-called ordinary mature women are very beautiful too. There is nothing in this world better than the sight of a mature woman in possession of a shapely bottom.

The next day was Friday and I was working at home. That night I was again undecided of what to do. Sophie was not averse to the idea of spanking, but was this just a game, or could we go to the next level? These thoughts churned around in my head all night, I was not sure I was any nearer an answer when I woke up the following morning.

We had coffee as usual and we had the usual easy conversation about the weekend etc. After coffee, Sophie went out the back to do some work in the garden and I left a sticky note on the kitchen table.

The cane would seem to fit the crime, how many strokes do you think the maid would deserve?

I popped back downstairs twenty mins later to see the message.

Six strokes seems to be the tariff for most offensives. Again, a smiley face.

I then wrote, Would this be over clothing or on the bare bottom?

Over the next couple of hours, we exchanged the following sticky notes. I know it sounds silly, but it was very exciting to me and I am sure Sophie was enjoying it too.

Bare bottom would certainly make the message clear.

Should the maid be made to count the strokes?

Definitely and say Thank You for each one.

At the end of the punishment, she must stay in position bent over, otherwise, the whole thing would have to be repeated.

If the Master of the House says so, I hope she remembers.

Just before Sophie was due to leave, I wrote my final message of the day. Do you think you should be punished in this way, for breaking my rules? Think about it over the weekend and let me know on Monday. If you decide to go ahead the punishment will take place next Friday.

I heard the front door close behind Sophie and went downstairs to see that she had taken the final sticky note with her. So began another weekend of waiting. When Sophie started to work for me I removed a picture from my office wall. It was an image of a classic French maid holding out a cane for someone to punish her with. It is one of my favourite pictures and I like looking at it during boring conference calls. It seemed a bit daft to hide it in the cupboard now so I replaced it on the wall.

Monday rolled around as usual and when Sophie arrived, I was on a call. Over coffee, we managed not to mention the elephant in the room but talked about the mundane even talking about the rain due that afternoon. I heard the front door close behind Sophie later and decided that she must have chosen not to go ahead. I could only say I was extremely disappointed. The disappointment did not last long, I went downstairs to find a note saying. Your maid will report for punishment in your office at ten on Friday. She will knock on the door and wait to be asked to enter.

The rest of the week passed in a bit of a blur, again I was away on Wednesday so did not see Sophie. Time did seem to drag but finally, Friday came round. I decided to dress quite formally and waited in my office for the knock on the door. I heard Sophie come into the house a few minutes before ten o’clock and heard her moving about downstairs before she climbed the stairs to the office. At exactly ten o’clock there was a timid knock on the door.

“Enter,” I called. It does take a lot to surprise me, but what a saw next totally shocked me (in a particularly good way). Sophie came into the room dressed to resemble the French maid in my picture. She was wearing a short frilly dress, black stockings, and suspenders together with high heels. She looked stunning. She also looked extremely nervous.

“I have come for my punishment,” she whispered.

“Remind me why are you to be punished today?”

“I disobeyed your very clear instructions, Sir.”

The Sir was whispered very quietly.

“Right let us get started then. Six strokes of the cane across your bare bottom.” I looked up at Sophie who just gave a slight nod of her head.

“The cane is on the hook behind the door if you would be so kind as to pass it to me.”

Sophie looked behind her and saw the cane, she had to turn round to take a couple of steps to reach the door. I got my first glimpse of her bottom. It was peeking out under her frilly skirt and looked like the perfect bottom to receive the cane. She did look stunning.

Sophie held out the cane to me, again like the maid in the picture. When passing it over she said in a quiet voice, “The cane for you to use on my bottom, Sir.”

“Thank you, Sophie, now if you will approach the desk, bend over and push your bottom out for me. Remember at the end of your punishment remain in position until you are told to rise. If you fail to do this the punishment will be repeated. Do you understand?”

“Yes sir, thank you, Sir.”

I was not sure what she was thanking me for me but was not going to ask.

She stepped forward and very gracefully bent over my desk, she reached out and gripped the far side of the desk and pushed her bottom up, it was perfectly presented for the caning to follow.

“Do you want to remove your knickers, or should I do it for you?”

“Please Sir could you do it, it is so shameful.”

I lifted the skirt up, although it was so short anyway, and then hooking my thumbs into the side of her panties slid them down to the tops of her stockings. I took a step backward to admire the view. There is honestly no better sight than a beautiful mature lady in stockings bent over presenting her bottom for the cane. I could have stood there for an hour just taking in the view. However, the bottom was not going to cane itself. As I retrieved the cane from the desk, I could distinctly smell the aroma of sexual excitement in the room. I know for myself it was very exciting.

“Right, we are ready, remember to try to keep your bottom still, thank me for each stroke and stay down when the punishment is over.” I also added, “if you want this to stop at any time just say primrose,” where primrose came from I have no idea.

“Yes Sir,” Sophie said with a little more confidence in her voice.

This is it I thought, I tapped the cane lightly on her bottom and she flinched ever so slightly.

I brought my arm back and delivered the first stroke, certainly not full power but enough to give her a red line across her bottom. Sophie blew out all her breath shook her bottom most beautifully and lifted her head all at the same time. I was just going to remind her to count when I heard.

“One Sir. Thank you, Sir.”

She pushed her bottom up to receive the second stroke. I did not want to rush the punishment so placed the cane against her bottom again, paused, drew breath, and then. I delivered the second stroke and got a very similar reaction to the first, maybe just a small ouch from Sophie, again after a few seconds the count followed.

After the third stroke, I said to Sophie I would pause for a few seconds. I heard, “Thank you, Sir,” in reply.

After thirty seconds or so. “Right let’s complete the rest of your punishment, push your bottom out for me.”

Sophie did indeed push her bottom out in the most delightful way. It looked absolutely beautiful adorned with its three stripes.

I delivered the fourth stroke to the middle of Sophie's beautiful bottom. With each stroke, I was getting a gradually more verbal reaction. I decided the fifth stroke should be on the sit spot just above where the bottom meets thigh, I tapped the cane where I wished it to land and thankfully delivered the stroke just as intended. Sophie did let out more of a cry and waved her bottom from side to side.

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I did say, probably unnecessarily, “Sophie, will you please keep your bottom still, by your actions you deserve this caning. Now dip your back and push your bottom out properly. Keep still and remember to stay in position after this final stroke. Are you ready?”

Sophie looked around and with a slight smile on her face replied, “Yes sir.”

As usual with all canings I wanted the final stroke to be the hardest but had no intention of making it too hard. Again, I picked a spot in the lower half of Sophie's bottom drew the cane back, and delivered the stroke.

It was a perfect stroke but even as I was mentally congratulating myself Sophie jumped up, clutched her bottom, and was hopping from foot to foot.

“What are you doing Miss Finn, I specifically asked you to stay down after the final stroke.”

“Sorry Sir, I forgot.” Her face and manner did however not match the words she was speaking.

“What did I say would happen if you stood up?”

“The punishment would start all over again, Sir. Oh, please, sir.” Again, just the small hint of a smile.

“Right let us have you in the corner for five minutes and then we will have to start over. This could take all morning.”

Sophie moved to stand in the corner, by now her knickers were laying on the floor in a little pool of satin. I sat down behind my desk and took in the view, and what a view. Sophie was stood in the corner with her uniform barely covering her punished bottom.

“Sophie, I think you should put your hands on your head.”

“But Sir, you will be able to see my bottom.”

“You should have thought of that earlier, now hands-on head.”

Sophie did as she was told and indeed did reveal more of her bottom to my view. Six clear red stripes became visible and I sat back to admire my handiwork.

After the five minutes had passed, I stood up picked up the cane, walked over to Sophie, and spoke.

“Right back into position, and this time remember this is all your fault.”

“Yes, Sir, sorry sir.”

Sophie stepped back over to the desk, bent over, flipped her skirt up, and pushed her bottom out. I was in heaven.

“Right, you know the procedure now, we start back at one again.”

With that, I delivered the next stroke, which was greeted with a small cry and a frantic wave of her bottom.

“One Sir, thank you.”

The remainder of the caning was delivered with more gasping and wriggling but I did finally hear.

“Six Sir, thank you.”

This time Sophie did stay in position, and I was able to step back and admire my handiwork for a final time. Twelve lines across a perfect bottom was a beautiful sight to behold.

“Right Sophie, I will leave you to compose yourself, if you need the bathroom you know where everything is, I will see you downstairs when you are ready.”

I retreated to the kitchen; it was not yet eleven o’clock but what a day. After ten minutes or so Sophie came down back wearing her coat. She asked, “Is it OK if I leave early, I have some personal stuff I have to attend to.”

I could only reply, “Of course, I will see you on Monday.”

As Sophie closed the front door, I went upstairs to attend to some personal stuff of my own.

***

Sophie arrived as usual on Monday and we did not get a chance to speak until later in the morning. We sat down with coffee and biscuits and I casually asked.

“How are you?”

Sophie looked me in the eye and asked. “Are you asking me how my weekend was or are you asking how I am after been beaten by my merciless employer?”

“The second.”

“Well, after been forced to bare my bottom and receive twelve hard strokes of the cane, which was six more than agreed I was very conscious of my bottom for most of Friday. I had to inspect myself a few times. I did wonder what the other Mums at school would say if they knew. It was however incredibly exciting, and I enjoyed it immensely.”

She broke into a grin, and I smiled back.

“Where did the uniform come from?”

“My ex-husband liked that sort of thing. It was hiding at the back of the wardrobe at home. I never thought it would see the light of day again. Did you like it?”

“You looked stunning.”

“Well thank you, kind sir.”

“Shall we do it again sometime?”

“Yes, I think so, yes.”

For the rest of the morning and most of the afternoon, I was tied up with calls. So, it was not until Sophie had gone home that I came back downstairs. On the dining room table, there was an envelope with my name on it. With great curiosity, I opened it to find a piece of typed paper with the headline saying.

Punishment Slip.

Offense. Surfing Pornography.

Sentence. Six strokes of the senior cane, bare-bottomed

Date. Friday @ ten am in your office.

Signed. Sophie Finn

It is hard to describe the emotions that raced around over the next couple of minutes. Partly I was extremely excited but very scared, would I go through with this? My mind was in complete turmoil, suddenly the stuff of dreams was made real, but do you want your dreams to come true?

This conflict of emotions continued throughout the rest of the day and most of the night. I was travelling the next day and not due back again until Thursday. I screwed up all my courage and simply left a message for Sophie saying, See you Friday.

The next few days passed in a bit of a whirl; the course I was running went well. I was certainly fired up on adrenaline. I still had all sorts of emotions but there was a great feeling of anticipation mixed with a good deal of fear. I arrived home Thursday evening to find a note for me saying. I do not wish to see you until ten am tomorrow, please knock when you are ready, I would advise you not to be late. It was signed, Mistress Sophie.

I did smile at the cheek of the note, but I was looking forward to this in a strange way.

Friday morning found me waiting in my bedroom for Sophie to arrive. Just before ten o’clock, I heard her key in the door and I heard her making her way up the stairs and into my office.

I was dressed in suit trousers and shirt, what should you wear to an occasion like this I wondered? At ten o’clock precisely I knocked on my office door.

“Come in.”

I opened the door to find Sophie sitting in my chair looking very stern. She motioned for me to approach the desk and then asked.

“Do you accept you should be punished for your behaviour?”

I swallowed an exceptionally large lump in my throat and quietly replied, “Yes, Miss.”

“You will address me as Mistress whilst in this office,” said a very cross-looking, Sophie.

“Yes, Mistress.”

Sophie stood up; she was dressed as a very classy-looking secretary. Grey jacket, white blouse, and grey fitted skirt. She was wearing black boots that disappeared under her skirt. Even with everything going on in my head, I did think wow she looks lovely.

Sophie made her way around to stand next to me. The next sentence set my heart racing.

“OK, let’s get you undressed, I would like you naked. Place your clothes neatly on the sofa and come back and stand here.”

I was of course expecting to bare my bottom but having to strip naked somehow felt far more humiliating. I slowly, and somewhat reluctantly, undressed and stood back in front of the desk. Being stood naked in my own office was a very strange feeling.

“Right over you go, bend over the desk and grip the far side. Feet apart and bottom right up. Remember to stay down at the end. As I am sure you know what happens if you do not. I will get the senior cane for your bottom to enjoy.”

Although I was sure my bottom was not going to enjoy this too much, I knew that Sophie was enjoying her powerful new role. Another part of my anatomy was having the time of its life and standing at full attention. My mind was a whirlwind of emotions with excitement and fear competing for first place. Fear was currently winning.

Sophie stepped over to the cupboard and was back in no time. She placed the cane on the desk in front of me and casually said.

“This will be visiting your bottom this morning and you only have yourself to blame. How many strokes was the punishment?”

“Six Mistress.”

“Ah yes, six of the best, the traditional punishment for naughty boys. Could you please count them for me, and woe betide you if you forget? Ready?”

“Yes, Mistress.”

The cane left my sight and I soon felt it pressed against my bottom it tapped me a couple of times and then I heard it woosh. It struck the centre of both of my buttocks. It was not hard, but I certainly felt the stroke.

“One, Thank You, Mistress,” I remembered to say.

More tapping and the second stroke landed. I was not sure if Sophie had done this before, but this second stroke was stronger and certainly had a sting. I remembered to count again.

The next three strokes landed, and each seemed slightly stronger than the last. I was starting to struggle not to cry out. It was also an effort to keep still.

“The last one coming up and remember to stay in position.”

More tapping and the sixth stroke landed. It took my breath away. My bottom was feeling on fire. I remembered to count and stayed in position.

Sophie put the cane down in front of me again and walking around the desk sat in my chair.

She did look incredibly beautiful, beautiful, and excited.

“You took your punishment very well.”

“Thank you, Mistress.”

Then with a twinkle in her eye, she stood up and bent over giving me a beautiful view down her blouse, I could see red lingerie trimmed with black lace.

“Would you like me to remove my blouse?”

“Yes, please Mistress.”

“It will cost you three strokes of the cane; would you still like to see?”

“Yes, please Mistress.” I had no hesitation she looked so sexy and the atmosphere was electric in the room.

Sophie sat back done and slowly undid the buttons and very slowly removed her blouse. Underneath she was wearing a red corset with lovely black lace trimmings. She again bent over giving me a grandstand view of her cleavage.

“You like?”

“Very much Mistress, you look beautiful.”

“You do say the nicest things, however now you need to pay the price.”

She collected the cane and disappeared from my view. The now-familiar tapping re-commenced.

“Three strokes, please remember the count.”

The first stroke was very firm, and I made my first involuntary sound. I did remember to count.

“Are we getting through to you?”

“Yes Mistress, it does hurt.”

“You wanted to look, was it worth it?”

“Oh yes indeed.”

The cane returned to tapping and the second stroke and the third was delivered. By now I had tears in my eyes.

Sophie sat back in my chair.

“Hurts does it?”

“Oh yes.”

She stood again turned and bent over slightly pushing her bottom towards me. I was transfixed.

“Would you like me to remove my skirt?”

Although I knew what was coming, my immediate answer was, “Yes, yes please.”

“Three strokes?”

“Yes, Mistress.”

She smiled very sweetly, and with her back to me undid the button on the skirt and gently pulled down the zip.

I watched in awe as Sophie stepped out of her skirt. The corset had suspenders holding up black stockings and she was wearing a thong to match her corset. The boots I saw earlier finished above her knee. She looked stunning. Sophie sat back down, pushed the chair away from the desk so I could see, and slowly sat back and opened her legs.

“Is the view worth the pain?”

“Yes, definitely,” I said, and I meant it. I am not sure my bottom agreed with that statement.

“Time to pay up.”

Again, she disappeared from view, and the following three strokes were applied to my very sore bottom. I did manage to stay in control, just. But there was a couple of noises that escaped me. She was giving me a proper caning.

She whispered in my ear, “Would you like me to remove my panties for you?”

I could only say yes.

Again, the slow striptease. She turned bent over and pulled her bottom cheeks apart just enough to show her hidden charms. She then returned to my seat. I could see her beautiful, shaved pussy. I was in heaven and as she spread her legs. I could not help but notice how excited she was. This in turn started my excitement again.

The three strokes that followed took all my willpower to stay anywhere near still.

Sophie pushed her breasts against my back and whispered in my ear, “Would you like to kiss my pussy and to make me come?”

“It would be an honour, Mistress.”

“Are you willing to pay the price?”

“Yes, Mistress for you.”

“You do say the nicest things. I will punish you first then take my pleasure. It does seem almost a shame to have to cane you, but it must be done. Final three coming up.”

They hurt. I had taken eighteen strokes and my bottom felt on fire.

“You may stand and step back from the desk.”

I did as I was asked. Sophie pulled my chair around the desk and sat down. “If you would kneel you may pleasure me.”

I could think of nothing I would rather do. I knelt and carefully approached Sophies perfect pussy. She smelt heavenly and was indeed very aroused. I kissed the tops of her thighs, up one stockinged leg and down the other. I then just lightly kissed her pussy. Sophie just groaned her pleasure, which encouraged me to start to kiss with more confidence and then start to lick.

She was extremely sensitive and seemed to be enjoying the attention very much. I have to say I do enjoy oral sex and hope that I have some skills certainly Sophie seemed to be enjoying herself. After several minutes of pleasure, I sensed Sophie approaching her climax. I continued to flick my tongue over her clitoris, and she did indeed reach her orgasm. At the point of her coming, she grabbed my head and pushed my face into her wet vagina. I was in heaven.

Sophie gradually came back to earth and smiled. She said, “Enjoy?”

“Yes very, very much.”

“Good, Thank you. Your punishment is now over. Do not bother getting dressed, if you could leave now. I will see you Monday.”

This did come as a bit of a surprise and if I am honest, I bit of a disappointment. I slowly left the room and returned to my bedroom. I heard Sophie moving about and after a few minutes, she walked down the stairs and closed the front door behind her.

Like anyone who has been caned, I bent myself over in front of the mirror to examine the damage. She had left a vivid collection of stripes across my bottom, they were painful, but I was starting to feel that lovely warm post punishment buzz.

I wondered what Monday would bring.

Published 
Written by DorsetP
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