Editor's note: this fictional work contains scenes of fictional rough, reluctant, dubiously consensual, consensually non-consensual (CNC), or non-consensual sex or scenarios.
I did not find out until after the events I describe below why I was nominated by the headmistress to carry out all physical punishment to the girls at the school. In the 60s things were very different to now. Girls were not only very often punished physically but the punishments were never questioned. I did not chose the punishment to be given I was just there to complete the punishment determined by the headmistress. The girls would bring me a note that detailed their offenses and the punishment to be given. The basic choice was caning, spanking or enemas. The events below were the third time I punished a girl and unusually the headmistress had said the punishment should be severe but she was leaving it to my choice.
When the 18-year-old Alice handed me her note I could not have been happier. She was over confident even cocky with stunning looks that meant that she was able to carry it off. I decided the punishment was to be a series of enemas as the comments on the note were for me to take the girl down a peg or two.
Alice had seemed unconcerned until she heard that she was to receive enemas until I was happy she was truly cleaned out. She pleaded to be spanked instead or even given the cane. I asked her why but she was reluctant to answer. I told her I would ask her again later and if she didn't answer she would receive more punishment.
"From now on you will do everything I tell you immediately and without question. Firstly you will strip and put all your clothes on the chair over there."
"Why do I need to be naked to take an enema?"
"That is last time you question me without having your punishment increased. Now out of your clothes so that I can see what I have to work with. I understand that you told the girls who you were bullying that they had to worship your body as it was as close to perfection as they would ever see. Let me see if I agree with your opinion."
As more and more of her body was uncovered I was finding it harder and harder to disagree with her. She was stunning attractive rather than pretty with a eighteen-year-old body that I would have died for. There was just a slight hint of puppy fat and her boobs were beautifully proportioned. I sensed that she thought they were too small as she hid them more than her hairless pussy that she seemed to want to display. In different circumstances I would have happily knelt between her legs and worshipped her with a willing mouth. I had to gather myself to ensure that I kept control of things.
"Would you call those perfection? They seem rather on the small side to me. Your nipples look huge and very excitable in comparison. Are they always as erect as they are right now?"
"No Miss Dent I am not sure why they are so arous.... so erect. I am not used to being naked in front of adults who are telling me what to do."
I wondered briefly if her bullying was actually hiding a submissive streak. I would certainly be able to test this theory as the evening progressed. The thought of dominating this gorgeous girl excited me greatly. I ordered her to stretch herself across the desk and hold the far side with both hands. I kicked her ankles gently to get her to open her legs until they were wider than her shoulders.
As she did so her very neat pussy lips opened very slightly. This revealed that there was more than a hint of moisture along the whole length. I wanted to open her further and particularly find her clit but knew there would be time later. I had prepared the first enema and left it in the bathroom. I was not able to pull myself away to fetch it so decided to prepare her for the enema nozzle first. I lubricated my fingers ignoring the gloves that I should have put on. I walked round the table so that I could talk quietly into her ear.
"I am now going to prepare your bottom for your enema. If the nozzle was going in your pussy I would not need to use lubricant but your bottom looks a little tighter. As you receive the nozzle and then the water I want you to imagine that it is the girls you bullied who are filling that sexy bottom of yours. By the time I finish with you you will feel like you have been fucked stupid by each and every one of them. Do you understand Alice?"
"Yes I think I understand Miss Dent. I am sorry for what I have done and will try and take my punishment."
"You will take your punishment and you will thank me for it. If you don't I will add a spanking or even a caning at the end. You will submit fully and then you may just get away with the three enemas."
"Three why three?"
"Firstly, because I say so and secondly so that the first clears you out with soap, the second removes the soap and the third is the large punishment enema that you hold for as long as I dictate. Is that that all right with you Alice?"
"Yes Miss Dent I understand. Thank you Miss Dent."
"There I do think you are beginning to understand how things are going to be this evening. Now let's start with me loosening up you bottom. If you relax down there I will try and make it painless and it might even be pleasurable."
"Thank you Miss Dent."
As I approached from behind her bottom did appear relaxed. The target was very clear, as there was a large area of black crinkled skin with the small opening set in the middle. I spread the generous amount of lubrication all over the black area working gently and slowly towards the center. When I felt the hole open slightly I started again from the outside. I was delighted to hear a deep sigh from the other side of the desk.
