Three Girls Caned by Headmistress Ch. 01

It would not now be seen as a suitable punishment for getting caught smoking. At my all girls school when I was a teenager caning was considered suitable. I had been caught with my two best friends and stood in front of the headmistress's desk. We were in our final term and were all 18. She gave us the standard lecture and invited us to bend over the desk each of us on separate sides. We were all dressed in standard school uniform.

The first thing that surprised me about that day was that when she tucked the back of my skirt into its waistband she left my dark blue knickers in place. She did the same to the other two before telling us that we would each remove one of our friends' knickers. I was told to kneel behind Anthea and pull her knickers down and off her feet. It seemed a very personal thing to do as my face was very close to her bottom. Anthea did the same for Brenda before Brenda knelt behind me and seemed to take an age to uncover my very vulnerable feeling bottom.

Miss Dent informed us that we would all receive six with the cane and she would deliver these two at a time as she went round the table. She circled the desk anti-clockwise starting with me. She stood to my left and took her time before landing the first right-handed swing low across my bottom. It was my first time being caned and couldn't believe the explosion of pain that struck me. The second landed before I had let my breath out. While she delivered the two strikes to the two girls my bottom got hotter and hotter until it felt like eggs could be cooked on it.

The next two seemed to be delivered with even greater force. The pain seemed white hot and I was not sure I would survive the final two. During the wait for the last two the heat spread throughout my nether regions. I wanted the last two delivered as soon as possible so that it would all be over. Miss Dent obliged delivering two, the hardest yet, in quick succession. The pain and the stress I was feeling caused me to at least partly lose consciousness. It could not have been completely as I was able to be aware of the final four screams of my friends as they suffered the cane for the final time.

The next thing I was fully aware of was Miss Dent picking up the phone. She asked that the head girl (Susan Foster) be put on the phone. When she was Miss Dent requested, or more accurately ordered Miss Foster to come to her office immediately. To any of the pupils in the school other than the head girl this would have been very scary. Susan Foster was almost as scary to us girls as Miss Dent herself. When she arrived we were still all three bent over the desk displaying our caned bottoms. The greeting was as if the headmistress was addressing a senior teacher not a pupil. The conversation that followed seemed to be carried out in code but I can remember every word to this day

"Susan, Miss Wentworth here seems to have reacted rather strongly to the caning. She seems to have become over excited by things and I think she is in need of some of your special TLC."

"Are you suggesting that you don't wish her to receive any further punishment?"

"That is correct Susan. I think she would benefit from some of your special balm that soothes caned bottoms so effectively."

"Sorry I am not sure are you wishing me to "reward" this girl or just apply cream to her caned bottom?"

I knew the meaning of the word reward but it seemed to indicate something that only they knew.

"No I think a deep massage of the effected area will be sufficient Susan. Miss Wentworth here appears to be very naïve in the ways of the world and I am happy that she remains that way for a little longer."

Even though I didn't have a clue what they were talking about I did see a very strong look of disappointment, or possibly something stronger, cross the head girl's face.

"So no further punishment and no reward for Wentworth today. She does look very much in need of a reward unless I am very much mistaken."

Miss Dent was curt with her next comments as she addressed the head girl more formally.

"Miss Foster if I cannot trust you to do exactly what I require of you I am forced to have Miss Wentworth's friends witness her aftercare. They will be required to report back to me later today. They will confirm your care and her response or more suitably her lack of her response. Do I make myself clear?"

Susan Foster changed from a confident colleague to just another pupil in response to this ticking off.

"You make yourself very clear headmistress."

Within a couple of minutes the three of us were in the head girl's spacious living area. She had not let us put our knickers on but had picked them up and put them in her pocket. She lined us all up behind a long sofa and told us to lean over it and put our hands on the seat. I was positioned in the middle and told to hold the hand of each of my friends. She then kicked gently on my ankles to get me to spread my legs wide apart. Anthea and Brenda hooked their ankles behind mine so that mine were trapped. My friends were told that they were not to let me move while she applied cream to my bottom.

When her single finger traced the length of one of the six stripes on my bottom her finger was thickly coated with a cream that felt like it had been in a fridge. She gently coated each of the six stripes leaving each coated with a thick layer of lotion.

"I want you to hold your breath until I have rubbed all this cream across both of your cheeks."

She used the whole of one palm to spread the cream none too gently across my whole bottom. It did not feel like a soft hand but my cheeks did cool down a little nonetheless. As soon as she removed her hand I let my breath out with relief. The head girl then deposited a large glob of the cream on the center of my right cheek.

"Now if you are sensible you will keep very quiet while I administer the deep massage the headmistress required me to complete."

Even with this the penny did not drop. As her middle finger covered with cream circled the heart of my bottom I was shocked at what I suspected the deep massage would entail. I wanted to say something but she had made it clear that I was not to make a noise let alone speak. The circling got smaller and smaller until her finger was teasing my very sensitive anus.

The next few minutes changed my life. She finger fucked my bottom and I dissolved into tears with the sheer pleasure and frustration of it. I didn't know at the time that she was repeatedly bringing me right to the brink of orgasm before leaving me hanging. She carried on the rhythmic, slow stroking of the inside of my rectum even as I started to push back to maximize the penetration.

"Headmistress certainly knew the effect the caning had on you didn't she Wentworth? Your virgin pussy is dripping like a tap and unless I am careful I will reward you without even touching it."

At this stage I thought I understood the conversations between the headmistress and the head girl. I had never experienced an orgasm but I had heard other girls and one of my friends discussing them. All the talk was of putting things in their pussies and rubbing themselves. No one had touched my pussy but now I was very aware of it being very wet.

"Headmistress would stripe my bottom just like yours if I rewarded you by playing with your pussy until you orgasm. I can however carry on playing with your bottom for as long as I wish. Would you like me to do that Wentworth or do you want me to send you packing?"

I couldn't possible ask this girl to bring me to orgasm in front of my friends however desperate I was for the relief my body was screaming for. The thought of being left hanging and sent away was just as horrifying. I could not answer so kept quiet and hoped she would not make me plead with her. She seemed to take pity on me as she started to finger my bottom with renewed vigor. This time as my body built to unbearable arousal she did not stop but added a second finger. My orgasm hit me so hard with such violence it frightened me. My hips were thrusting totally out of control and I wet myself. Compared to any orgasm I have experienced since it just went on and on and I wonder if I actually experienced more than one back to back.

It is only really looking back that I appreciate the strength and completeness of that orgasm. At the time I was frightened by the violence of it as I thought it was some sort of seizure that was overwhelming my whole body. Now I often seek to try and replicate that same frightening violence. It is my go to fantasy when I masturbate.

Over the next years I was seeking sexual experiences that could get close to the same intensity.

That seeking of sexual intensity will be detailed in future chapters.