Will 18 Year Old Bully Get Punished?

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.

"Am I being gentle enough with you Alice?"

"Oh yes Miss Dent, thank you Miss Dent that is very, it is very gentle."

I turned my hand round so that the pad of my thumb was resting on and over the relaxed opening. My fingers were so close to her pussy I was sure I could feel heat radiating from it. I gently applied pressure with my lubricated thumb. It seemed to be welcomed into the warm orifice and I was certain that the bottom was being pushed back to ensure deeper entry. Now the sighing was louder and there was no mistaking the sexual nature of it.

Not for the first time in the evening my thoughts were not of punishment but of pure sexuality. I wanted to bury my face where my hand was currently busy. This was not helped as the most beautiful aroma ever assaulted my nostrils. I had not touched her pussy but now it was more than moist. I swear if I was not already been bi then this would have turned me for ever.

I justified the act of fucking her bottom with my thumb, as lubricating it but we both knew better even when I added more lubrication. I also managed to brush her pussy three or four times with my fingers as if accidentally. Even these light brushes were enough to reveal that her pussy was now swollen and very wet. Her clit had also put in an appearance but was not fully exposed.

Her frustrated groan was music to my ears as I removed my hand and left her slumped as I retrieved the enema bag. I hung it from the hook attached to the tall lamp next to the desk. This not only offered the height required but also lit the area brightly. The nozzle was not as thick as the ones I would use later and slid in with no resistance. I started the flow of soapy water into her rectum and used the nozzle to gently fuck her willing anus. On a number of times her breathing became very labored and although I was sure she was not about to orgasm I stopped long enough to let her settle down. It was exciting to see and hear her arousal grow again. Much to my surprise I only had to stop twice to let her recover from cramps caused by the soapy water.

Eventually it was with reluctance that I let her up and pointed to the bathroom. I took the bag off the lamp and followed her into the bathroom. She had obviously not considered this as she was sitting on the toilet with her fingers buried between her legs. Much to my surprise she had not started to evacuate.

"Don't move or muscle or you are in deep trouble young lady."

When I stood over her, her fingers were still resting on her aroused clit. Her eyes had a look of desperation in them.

"I am so sorry Miss Dent I was just so, I was just so .... I couldn't stop myself."

"You mean you could not stop yourself from masturbating during your punishment. What do you think that will earn you?"

"Oh please don't spank me. I am sorry Miss Dent let me change my answer. I deserve further punishment, whatever you see fit."

"Had you not changed your answer I would have caned you but due to your clear apology I will reduce it to a spanking. Now you have five minutes to evacuate and clean up before you receive the second enema. Please leave your pussy and clit alone while you do so."

The second enema was administered with her on her back on the desk. I had her hold her legs wide apart so as to embarrass her as much as possible. I commented a number of times about how aroused she appeared to be, this further distressed her. This was a quicker enema and she did not seem to get as excited as she did during the first one. I ensured she behaved while she evacuated and I prepared her last enema. This was large but at a temperature to be as comfortable as possible.

I laid her on a thick rug on her back. I knelt between her legs as I lubricated her ready to receive the nozzle. This one had two inflatable balloons and a long tube to ensure the water was delivered deep into her bowels. When the tube was buried deep I inflated the first balloon inside her rectum. Her eyes opened wide as it stretched her like never before. The second balloon was inflated outside her bottom and I knew she was water tight. Now I told her how this was the punishment enema and it was going to be much bigger and she would hold it for a long time.

She was lying on her back and I put a big cushion under her bottom to tilt her hips back. Her legs were apart and she was looking helpless but incredibly sexy. I started the flow and sat back to enjoy tormenting the beautiful girl in as many ways as I could. As she started to fill her hands slowly found her boobs and then her nipples. I pretended not to notice that she was now playing with her now huge dark nips. When it became blatant I lent towards her ear and said.

"Do you want the spanking upgrading to a caning?"

"Oh I am so sorry I am just so fucking aroused I could not help it. I have never needed a cock like I do right now."

"You can cut that language out straight away. As for your arousal you were well on the way when you walked in here. Right now you are responding to being submissive and having your ass played with. I suspect that no one has played with it before. Clearly you have had your pussy played with by a cock but trust me there is more than one way of skinning a cat or should I say a pussy.

I am now going to fill you until you are ready to explode. If you are really good I might just let you explode. Do you understand?"

"Yes I think I do I will try as hard as I can."

She took an impressive amount of water before cramping so badly I had to stop the flow. Kneeling next to her I used both hands on her stomach to ease the water higher into her bowels. The look on her face nearly melted my heart. As I worked she pushed her hips into the air as if pushing up towards an invisible lover. Her breathing and sighing reflected how excited she was again. I had not noticed that in massaging her, my one arm was close to her boobs and the sleeve of my loose top was catching on her extraordinary right nipple.

I massaged higher and higher pretending that I had not noticed the effect my sleeve was having on her nipple. She noticed it and her breathing was getting out of control. I wanted this cocky young beauty to be begging me for relief and planned to get her right to the edge and keep her there as many times as possible. Her mouth said nothing but her eyes were begging already.

I started the flow again and moved my hands much lower with one hand a couple of inches above her pussy. My massage now was aimed purely at ensuring that her clit was fully exposed and visible to me. I was loving the total control over this highly excited beauty. Her clit was now fully released from its hood. Not the biggest I had seen but probably the most erect. It was nearly purple in color and it took every bit of my willpower to not bend and suck it to an instant orgasm.

I realized that it would take much less than licking her clit to bring the lovely Alice to climax. I was sure a gentle blowing of air across her clit would have had devastating results. This thought was what confirmed that she was totally under my control. A control that had me almost as excited as the girl fast filling with water.

"Please Miss Dent I don't think I can take any more water. Please stop."

"Oh believe me you can and you will take more. There is another pint to go but you are doing well. I am going to stop the flow one last time. I will spread what is inside you to make more space. Lie back and relax as much as you can."

The massage this time was primarily aimed at stimulating the helpless girl. I was close enough to her clit to arouse it without actually touching it.

"As you have 10 minutes to retain the water from when you are full I will let you hold your boobs to comfort yourself. It might help you take your mind off your full bowels."

As the last of the water drained into her she was doing more than holding her boobs. She was pulling and pinching her nipples as if to try and milk them. Her whole being was alight again and her eyes were pleading even if they were not sure what they were pleading for.

"Listen carefully now and do exactly what I tell you. You are to put your hands behind your head until I give you permission to play with your nipples again. Do it immediately and I will reward you."

With a groan of deep frustration she did exactly as I said.

"Good girl that was very sensible. I promised you a reward. If you keep your hands where they are I think you will enjoy what I am going to do next."

With this I moved to kneel between her legs. I resisted touching her gaping pussy and purple clit. I circled her cheeks with my hands gradually moving towards the balloon and the dark skin stretched tightly around it. I teased it gently studying her face. She held my stare until I held the balloon and pushed squeezed and pulled it. Due to the pressure it was under there was little movement but what there was had a dramatic effect.

Her hips now took on a life of their own. I was sure she was now approaching the point of no return. I intensified the manipulation of the balloon matching the thrusting of her hips.

"You have been a good girl Alice. Is there anything you would like to ask me for permission for? If so be very specific because I will only grant you permission for something you ask for."

"Please Miss Dent can I play with myself and can I cum, can I have an orgasm please."

"You are due 6 with the cane. You may play with yourself and you may orgasm. Every minute you are able to delay cumming I will reduce the number with the cane."

One of her hands found her nipple while the other found her clit. I did not stop playing with the balloon as I wanted her to fail dismally. I need not have worried as her hands and hips worked in unison until she simply exploded. I have seen many women orgasm but this was the most spectacular one I have seen.

Her legs clamped her hand and arm and her hips thrust backwards and forwards time and time again. She wailed throughout a violent orgasm that seemed to last for nearly 20 seconds.

After she evacuated and cleaned up she said she had never had an orgasm that was half as good. Now she was feeling super relaxed and on cloud nine. She asked whether she was due 5 or 6 with the cane. I said I would not cane her that evening but she would report a week later and I would spank her instead.

She actually thanked me for being lenient.