My laptop went ‘ping’ telling me I had a new e-mail. The message was from Pippa; she was requesting a meeting for herself and her old school friend. They wanted me to play the role of their headmaster.
The e-mail was very detailed, but briefly, Pippa Banks and her friend Fiona Lord had been best friends at school and remained so even after twenty-plus years. Whilst at school they had been responsible for burning down a tool shed when they had failed to properly extinguish the cigarettes they had been smoking. To make matters worse they had allowed another girl to be punished for their crime. Even after so many years, they both still felt guilty and would like to be punished to go some way towards atoning for their crimes.
As I run a spanking service for women looking to fulfil their fantasies around spanking and corporal punishment, I was happy to help. Whether this incident ever took place or whether Pippa and Fiona attended the same school does not matter.
Pippa and I exchanged messages and had a thirty-minute phone conversation before arranging a date for this matter to be dealt with. We arranged to meet at my house and firstly get to know each other before deciding if we all wanted to take it to the next stage. However, if they did choose to enter the Headmaster’s study, they would be treated as naughty ex-pupils and they would be punished accordingly. Pippa and I agreed on what that punishment would entail.
Although I have met many women whilst running my spanking service, I have never had the pleasure of punishing two women at the same time. It has always been a fantasy of mine, one that I never really expected to realise.
The day of the visit dawned I was not expecting them to arrive before four in the afternoon, so I had a long day ahead of me anticipating the action to follow. Many thoughts flashed through my head. Would they turn up? Would they want to proceed to the punishment? Was this all some elaborate joke? Your mind can make up all sorts of things and in this case none of them helpful.
However, just before four o’clock, the doorbell rang and two attractive women in their mid-forties entered the lounge. I would be lying if I said conversation came easily for the next few minutes but gradually, we did manage to break the ice, and everyone started to relax in each other’s company. It was obvious that Pippa and Fiona knew each other very well and both were excited to try out the scenario. So, after chatting for a while, we all agreed we wanted to proceed. They wanted to get changed and I showed them into my spare room. I then pointed at the office door, which was closed at the time.
“You will knock on that door at five o’clock, once you enter the room you will be treated like the naughty girls you wish to be. It would not be in your best interests to be late.”
I could detect a mixture of emotions on both of their faces. I only had one overriding emotion: that of excitement. I entered the office, found my traditional cane and placed it on the desk in full view of anyone entering the room. I sat down to wait for five o’clock. I was dressed in a two-piece suit and looked like the strict headmaster I was soon to be enacting.
On the stroke of five o’clock, I heard a knock on the door.
“Enter,” I called.
Two perfectly dressed adult schoolgirls entered. Both were wearing straw boaters, black blazers, a white blouse, a tie, and grey skirts that ended just above the knee. I also noticed they wore black nylons and black stilettos. I am sure this has never been an approved school uniform but frankly, I did not care. Pippa was the taller of the two, around five feet five inches, with a pleasing mature figure. Fiona was slightly shorter and a little more buxom; they both looked truly magnificent.
“Stand before my desk.”
Both slowly approached and I could see they were fixated on the cane. They looked like they could see a snake. I was almost certain this was the first time either had seen one close up, and knowing for what purpose it was soon to be employed, you could understand the fearful look in their eyes.
“So, girls, justice has finally caught up with you. Twenty-plus years too late but it is finally time to atone for your sins. You are both in a great deal of trouble, damaging school property, smoking, letting someone else get punished for your crime, and not coming forward to own up. Is there anything else I need to know?”
“No, sir, we are very sorry, sir,” Pippa spoke not in her usual confident tone but like the afraid woman she was pretending to be.
“I can assure you; you will be very sorry before you leave here today and that applies to both of you.”
“Yes, sir, sorry, sir.”
“If you still attended this school, I would seriously consider expelling you. But that option is not available to me. So, I have no option but corporal punishment, severe corporal punishment. I can see you have noticed my cane. It is going to find itself remarkably busy this afternoon. Have either of you been caned before?”
“No, sir,” they both chorused.
“Well, you are in for an enlightening afternoon. I think twelve strokes each. Six strokes over your knickers for the damage to property and the smoking and six strokes on your bare bottoms for letting someone else take the blame.”
Although we had agreed on the punishment in advance, they both looked suitably nervous at this point. I was thoroughly enjoying my role as headmaster.
“You need to get ready. If you could remove your hats, blazers, and skirts then leave them on the sofa, we can begin.”
Pippa and Fiona shuffled over to the sofa and both removed their straw boaters and placed them on the arm of the sofa, their blazers quickly followed, and they slowly unzipped their skirts and stepped out of them. Both wore black stockings attached to black suspender belts with very plain white cotton panties.
“Back in front of the desk, both of you.”
The two of them stood nervously before me. “I shall deliver the first six strokes across your knickers; you will then swap places and I will repeat the process. Then you will remove your underwear and we will complete your punishment with six of the very best across each of your bare bottoms. You have only brought this punishment upon yourselves. Who is going to go first?”
The two nervously looked at each other and Pippa quietly said that she would be first.
“Right, Pippa, bend over the desk. Reach out and grasp the far side, keep your legs together and push your bottom out. I do not expect you to speak during your punishment; try to keep still and let’s get this over with without too much fuss. As for you, Fiona, stand over by the door and you can watch. I would like you to keep a count of each stroke. After each stroke, I would like to hear, ‘one, sir’ and so on.”
Both girls moved to do as I had asked.
Pippa placed herself across my desk and pushed her bottom right up. She looked over her shoulder and asked. “Like this, sir?”
“Yes, exactly like that and keep it in that position throughout.”
I have to say that her mature bottom presented this way looked very inviting. There is no better sight than a female posterior willingly submitting to punishment. I was very ready to deliver the promised caning. We had agreed in advance that the strokes were to sting but I was not to be too severe as they wanted to see what it was like.
I picked up the cane and swished it through the air a couple of times. It does make such a beautiful noise. A very scary noise if you are in Pippa’s position. Fiona looked incredibly nervous even though her bottom was safe for the moment. Pippa tensed her buttocks at the sound. “Relax yourself. I want a relaxed bottom throughout this punishment.” I knew I was asking for the impossible, but it was worth a try.
“Right, the first stroke coming right up.”
I placed the cane in the middle of her bottom. At this point, you could cut the atmosphere with a knife. I lifted the cane and delivered a firm stroke right in the centre of Pippa’s bottom. Her head jerked up and she stamped her foot.
“One, sir,” I heard Fiona announce.
“Now you know what to expect. You have five more to come in this session. Prepare yourself and push your bottom up again.”
“Yes, sir, thank you, sir.”
I chose to ignore that I had asked her not to speak.
Strokes two to five proceeded, Fiona kept count and Pippa managed to take her punishment well. Each stroke produced foot stamping and wriggling with various “oohs” and “arrrs” but she did remain in position and kept her bottom pushed out.
For the final stroke, I decided to deliver this at the sensitive point where thighs meet the bottom.
“After this stroke, remain in position until I ask you to stand.”
I tapped the cane at the top of her thighs; Pippa flinched. The stroke was delivered. There was a loud vocal reaction and she stamped both feet in turn but remained in position.
“You have taken your punishment well; you may stand and rub your bottom if you wish.”
Pippa was straight on her feet and she did indeed rub both buttocks to ease the sting. She looked lovely. She looked at me and with a slight smile said, “Thank you for taking the trouble to punish me.”
“My pleasure. Can you please swap places with Fiona.”
I sensed that Fiona, although interested in the idea of being punished, was more fearful than Pippa. I decided that I would introduce her to the wonderful world of consensual corporal punishment as gently as possible.
“Fiona, you have seen what happened to Pippa; the same is going to happen to you. I wish you to present your bottom for the cane and try to keep it still throughout. The punishment will soon be over. Like Pippa, you only have yourself to blame.”
Fiona approached the desk and bent over as Pippa had done.
“Please push your bottom out.”
Somewhat reluctantly Fiona complied. She had a more generous bottom than Pippa but nonetheless it looked like a picture; pushed out with her white panties covering her buttocks, it was truly a sight to behold.
“Pippa, you will keep count for Fiona.”
“Yes, sir.” I looked around and Pippa was staring at Fiona’s bottom; you could tell she was very excited at what was happening.
“Right, let us get this task over with.”
I tapped Fiona’s bottom and delivered the first stroke. Fiona gasped and stamped one foot and then the other, and to give her full credit, she pushed her bottom out for the second stroke.
“One, sir,” said a rather breathless sounding Pippa; she had come closer to get a better look.
I delivered the second stroke with a similar reaction from both Fiona and Pippa; after the third, I told Fiona she was doing well and that she was halfway there.
I continued the punishment and delivered the final stroke at the junction of thigh and bottom. This got a far more vocal reaction and Fiona thrust her bottom around in a very provocative manner.
“You may rub your bottom.”
Fiona did not need a second invitation. She quickly stood up and vigorously rubbed herself. I have heard this called a spanking dance and watching Fiona it was easy to see why.
Pippa’s eyes were glued to the scene before her. She stared at Fiona’s bottom, whilst one of her hands still clutched her punished backside.
“Right, girls, that is the first part over. Let’s have you stood in the corner for five minutes. I want you to think of the reasons you are here and the rest of the punishment you have coming. Pippa, you stand over there and Fiona in the opposite corner.”
The two complied with my request and I was faced with two knickered bottoms, each with a red stripe at the top of her thighs. I was in heaven and still with the main course to come.
After a short time, I announced, “Right, let us get this over with. Could you please both remove your panties and stand before my desk.”
Both girls moved to the sofa. Pippa turned away from me and made a big show of undressing; she bent right over when removing her knickers and blatantly displayed her punished bottom. Fiona was more demure but both semi-naked came and stood before my desk. Pippa had a shaved vagina and Fiona had a very neat and tidy bush. I would find it hard to say which I preferred; both were equally beautiful. This was a dream come true.
“You know what is about to happen. Six strokes to be delivered to your bare bottoms for letting someone else take the blame for your crimes. Justice at last. Pippa, again you will be punished first. Fiona, can you please come round to this side of the desk and hold her shoulders in position. Fiona, you will also count the strokes.”
Pippa bent over as before and pushed her bottom right out, displaying herself quite lewdly for my attention. She was obviously in a state of high arousal. I was feeling the same. Fiona stood and placed her hands on Pippa’s shoulders as requested.
“Right, six of the very best coming up.”
I lined up the cane on the lower half of her bottom and delivered the first stroke.
This got a vocal reaction from Pippa and she waved her bottom around. “One, sir,” Fiona intoned.
“Can you please try to keep your bottom still.”
“Yes, sir, it is just so hard when you are punishing me like this.”
“Number two coming up.”
The rest of the caning proceeded in a similar fashion. Her final stoke I decided to make harder than the rest and Pippa let out a loud “ouch” in response.
“You may rub,” I advised.
Pippa stayed in position and reached behind herself. Taking a buttock in each hand she proceeded to rub her bottom. She pulled her buttocks apart in this process and showed all her charms. She knew exactly the effect she was having and she was enjoying the performance she was giving. I was equally enthralled by the vision before me. When she finally stood, I asked the girls to swap places.
Fiona bent over and Pippa held her shoulders. I delivered the first stroke crisply. Fiona stamped her foot, which seemed to be her way of coping. Pippa counted the stroke and leaned over to get a close look at Fiona’s suffering bottom. Throughout the next five strokes, Pippa looked closely and when we made eye contact, I could see the excitement in her expression. She found the whole scenario very stimulating.
After the punishment, I said I would see the girls downstairs when they were ready.
I made coffee and waited for fifteen minutes or so before the two women made their way downstairs. We had a coffee, me sitting, and they both chose to stand, which was understandable.
As they made to leave they both thanked me for the experience. As Pippa was leaving, she passed me a note. When I closed the door on them, I looked at the note: Could I come and see you on my own sometime.
I sent her a text saying, anytime when are you thinking?
A little while later, I entered my office. On my desk were two pairs of white panties with a note saying: Souvenir. Thank You.
The End
