The Head Girl

Prologue - Miss Kitten

The one thing that most makes my 18 year old body happy is to orgasm. I love to shave my little pussy smooth with foam and a sharp razor and then moisturise my inner pink cunt lips all over my mound so that it's so soft to touch. When you run your fingers down my stomach towards and over my vagina it feels like silk. I take such pleasure in my own pussy because, when you've been in education at an all girls boarding school since the age of 11, you have to learn how to have some fun. One has to find how to pleasure yourself just to survive the sexual frustration throughout school as us girls rarely had access to boys.

As our hormones raged throughout our teens the male teachers often became objects of lust. My dorm and I would often discuss these teachers at great length. While we're lying in bed in our shared dorm most nights just before we fell asleep, we'd debate which teacher had the biggest cock. Whether Mr Davies our Physical Education teacher had as fat and as long a cock as it looked underneath his sports kit. Did the tall skinny art teacher have a long thin pencil penis as his trouser bulge would suggest? What did Mr Jones our headteacher look like under his suit? Often I would also imagine the female teachers undressed too, consider whether they hard large or small nipples under their bras, whether they shaved their pussies just like me or whether they had a nice bush of curly hair hiding their slit.

When we lay there speaking so filthily it was obvious to me that all of us in the dorm would start becoming aroused, turning each other on as we discussed such sexual things with each other. In the night time shadows I would sometimes notice one or two of the girls duvet covers moving as they played with their own pussies. As head girl, I was in charge of the behaviour of my fellow girls but this situation always put me in a quandary. I considered whether I should mention it to them. They should be sleeping and instead their muffled, panting breathing could be heard by the other girls, keeping us awake. Keeping me awake. I would have been such a hypocrite if I had told the girls off for it, seeing as I would always lie listening to their movements while frantically rubbing my own swollen clitoris. I would find myself even closer to orgasm with each noise I heard from the other girls. I wonder if they ever heard my low moans into my pillow as I came thinking of them masturbating in the same room as me, at the same time as me.

Throughout school since age eleven till now at age eighteen, we stayed with the same dorm mates . As we grew older and developed we really got to know one another more and more intimately. We spent many late nights discussing our developing boobs, bra sizes, our crushes on boys and our sexual desires. I knew for instance, that Angela often liked to wear no underwear to feel the breeze on her pussy. They knew I shaved my own pussy and once or twice I'd been asked for advice by the other girls on how to perfectly shave their pussy lips smooth without missing a patch.

Lately things had really heated up in my dorm. My closest friend Jane had bought me a vibrator for my 18th birthday. When I opened it Jane made out that it was a joke gift and the whole dorm giggled. Lots of chests heaving with laughter and I couldn't help but glance at all my school mates breasts jiggle and shake. There was many mischievous looks passed between us.

We stayed up late on my birthday and luckily neither head teacher nor matron noticed the sounds. He could be a very strict head master and I would hate to get into trouble and endanger my Head Girl status. My parents were so proud of me. Our posh boarding school had such strict rules and regulations on how we should act and what we should wear. I have always been very good at playing to the rules, on the outside. I put on a good act, good enough to have been made head girl. But, Oh how I misbehave underneath the good girl act.

Later on my birthday, after the giggling from the vibrator gift had settled down we all sat in a circle passing liquor around. We were playing a game where each time you were passed the bottle to take a sip you had to admit to a sexual action you'd done. Jane admitted she'd fucked her 29year old boyfriend in the back of his car. Amanda told us she had already bought and used a vibrator. I'm sure the thought ran through all our heads about whether she's used it with us all in the same room. The eyes turned to me at that point and they asked me to get the vibrator present out, everyone wanted another look.

It was a huge 10inch bright pink cock. We passed the toy around. When Sarah took her sip of the drink instead of telling us about a sexual action she'd done, she preformed one for us and dared to suck on the big pink vibrator like it was a cock. By this point my pussy was so wet in my little lacy panties under my nightie. I do love wearing sexy underwear sets, if nothing but to please myself and to give the other girls something nice to look at when we get dressed together in the morning.

The drink went round a few of us and once it reached Angela, she requested to perform rather than tell us a story, she wanted give me a birthday kiss. The girls all giggled in nervous anticipation, I leaned over towards Angela and as our soft lips met our tongues entwined I felt my nipples stiffen and a shiver run to my pussy, this was turning me on far too much. I sneakily ran one finger up her thigh as she pulled away from kissing me.

When I sat back down Jane pointed out that I had stiff nipples pointing through my fairly sheer nightly. Jane was almost mocking me, but there was an undertone of lust in her tone of voice. As it was her sip of the alcohol next she requested tipsily that she would chew on my nipples if the other girls were comfortable with watching her, and from there things turned into ecstasy. The flick of her tongue on my hard nipple, then the nip of her teeth and suddenly her hands were running down towards my pussy, pushing aside my wet panties and roughly her fingers went inside my aching hole in front of everyone.

The other girls in the room watched as she slid her fingers expertly in and out of my wet pussy, then up circling my clit and back inside me. I imagine she was playing with my pussy in the exact same way she plays with her own.

From then on all the girls in our dorm have really opened up to each other, literally and metaphorically. Many legs have been opened wide and often bedtime has turned into very sexual lesbian experiences. We like watching each other play with ourselves and each other. Occasionally everyone joins in, all openly masturbating in front of each other at night in our dorm. My vibrator has been used over and over again in my tight pussy, pushed in and out by my dorm mates as they lick my clit and pull at my nipples. It's our little secret.

Mr Jones

"That will do!!", I bellow loudly and I fling the door to the girls dorm open, "this level of noise is intolerable!". As the male head master of an all-girls school, I have to excerpt my authority loudly to keep control occasionally.

"Miss Kitten, this is the 3rd time I have had to warn you about the noise from this dorm, and as head girl, it's your responsibility to keep control of the girls in your charge." I shout.

Miss Kitten, May, you are a slim, pretty girl of 18 years, one of our senior girls with straight 'A' grades, but an altogether outrageous naughty side. The noise stops instantly as the girls cover themselves and stop what they are doing. You are looking worried, you know that I don't take any prisoners when it comes to discipline.

I wait a few more seconds to let the gravity of the situation sink in, and before I have a chance to continue, you pipe up with, "very sorry sir, we were only having a bit of fun and..."

Before you can continue I shout, "FUN! You were only having FUN! You are not here to have FUN!" You stop talking and stand in silence. It's only now that I notice that you are stood there in only your underwear, a black lace bra that clearly shows the outline of your large nipples perched on top of your very perky ample boobs. The knickers are again black lace, which is very lacey and hardly covers your pussy, which is visible showing that your are shaved. I feel a twitch in my cock, and suddenly snap back to the situation, it would not do to have a hard on in front of the girls so I return my mind to the situation.

I look around the dorm and then return to you. In a much more calm voice I say, "I don't want to have to come back up here tonight and you, Miss Kitten, I expect to see you outside my office immediately after breakfast, is that clear?"

The whole room reply with, "Yes Mr. Jones."

This is followed by a quivering voice from you saying, "Yes Mr. Jones, it won't happen again Sir." You look down at the floor shuffling your feet.

Before I step back out of the room, I take one more lingering look around the room, this time noticing several other girls, Jane Goode, she is stood there with no top on and has a very nice pair of boobs, "how did I miss them?" I thought. There was also Angela Smith, half turned away with no pants on at all, exposing her bare ass cheeks. I step back and close the door, and as I walk back to my office my cock twitches again as I am thinking of the view I have just left. Thinking about you mainly though, my Head Girl little Miss May Kitten.

On the way back to the office, I realise once I sit, I have a hard on. The view of you with your shaved pussy is still clear in my mind, and I find my hand rubbing my cock through my trousers. Before long, I have my flies open and my cock in my hand. I am running my hand up and down my cock, whilst I picture you in your lacy underwear. As I slide my had down my cock, pulling the foreskin back exposing the head, I run my finger around the rim, imagining that you are sucking my cock and licking the head. Having been at the school since the start of the spring term, some 5 weeks without any sex, it does not take long before I can?t hold on any more and with a grunt my cock starts to spurt come. Spurt after spurt spills from my cock all over my hand and trousers.

After I regain my composure I take a couple of tissues from the box on my desk and clean myself up. At least that had allowed my hard on to subside, but I still need to decide what to do about you. I can just let it go, you are the Head Girl and must set an example to the other girls, but what should I do? As I climb into my bed, I am still pondering what exactly I should do, unfortunately, all I can think of is what I would like to do to you, which is a long way from what I should actually do. Whilst I am thinking about you, predictably, my cock starts to twitch and get hard. For the second time that evening, I find myself fantasising about you whilst I rub my swelling cock.

The following morning, breakfast is finished by 7:45 as usual. The girls then have 45 minutes to get themselves ready for the first lesson at 8:30. As I turn the corner of the corridor, I see you stood outside my office as instructed. I notice you look different this morning, and it takes a few seconds to realise, the uniform is as per regulation today. The skirt is well below the knee and the blouse and cardigan are both done up. I find it hard to stop myself smirking as I wonder if you have the regulation large white pants on or your sexy lacy black pair. I walk past you without even acknowledging you and in to my office closing the door behind me. I have found over the years, its best to keep the young girls waiting for a bit.

After a while, I open the door, you are still stood there staring at the floor, "well come along, in you come," I say and you quickly walk into the office and stand beside the chair on the other side of my desk.

I sit and think for a while and then looking at you I command sternly, "sit down May." As you are sitting there, the underwear you were wearing last night is still on my mind and I find myself still pondering if you are wearing regulation underwear. I stare at you and after a few seconds in my best stern voice I ask, "you know as a head girl the school, I expect more from you don't you?" and before you have a chance to answer I continue, "and I can't have a head girl that cannot set a good example to the younger members of the school community."

I see my words are starting to sink in, "I know how proud you and your parents were when we made you Head Girl and it would be such a shame to have to remove that title from you, do you understand?"

I look at you and wait for a response, and with a shaky voice you say, "I am really sorry sir, it was just a bit of fun that got out of hand sir, won't happen again, I promise." You stare at the floor, I can see tears welling up in your eyes but you fight them back determined not to cry.

I speak softly, "OK Miss Kitten, I know how easy it is to lose control of a crowd of young ladies, I do, but as I have said before, that's exactly why we have a Head Girl, to show the others what is acceptable, and I am relying on you to do that, and if you let me down I will have no choice but to strip you of the position of Head Girl."

Fighting back the tears and through misty eyes you beg me not to do that so I follow up by saying, "If you can prove to me that you are worthy of the position then we won't have a problem Miss Kitten, but any more misdemeanours and there will be trouble."

You immediately reply, "Yes sir."

I remark "I am glad you have seen fit to wear regulation uniform this morning May, and I trust the entire! Uniform is regulation? Remember what I said about being an example?" I notice you fidget and pull you school cardigan closer together at the front. "Is there something you are trying to hide May?" I ask pointing to the closed cardigan. You immediately start to blush and look at the floor so I push the point a little more, "Please remove your cardigan Miss Kitten!?" I say sternly, and a look of horror crosses your face. "Now!" I say in a slightly raised voice and you slowly start to unbutton it and remove it.

As you pull your arms out of the sleeves, I realise why you blushed, I can clearly see your large nipples through the thin white fabric of your school blouse. "Oh dear Miss Kitten, I am not sure that that is quite regulation now is it??"

You look up from the floor, blushing bright red and sheepishly reply, "no sir?" I think for a while looking you up and down and spending altogether too much time looking at those lovely boobs and stiff large nipples poking through the blouse, and once again I realise I have a hard on.

"What am I going to do with you??" I say out loud, "this is not the behaviour I expect from the head girl you know!?" I look at you and I can see that you are upset at my comments, "So tell me May, why are you not wearing a bra??"

You blush a little more and quietly say, "the ones I have are uncomfortable and don't fit very well, I think my boobs have grown a bit?"

"I see?" I say, "and why have you not been to see Matron to request an new bra then??" I ask in a soft reassuring voice. You don't seem to have an answer for that, but it's then that I remember Matron giving me a bra that had been left in the locker room when the school closed for the winter holiday. I open my bottom draw and there it is. I look up at you, "well we can't have you running around the school without a bra can we??" before you have a chance to answer, I reach into the draw and pull out the bra, it's quite a large size so I am hoping it will be large enough, but still a little small for your generous chest and having those ample boobs spilling out the top of a bra would be a very nice sight.

"Please put this on immediately!" I say and hand over the bra. You are about to stand and I snap at you, "did I say you could leave? Sit!" You drop back into the chair and look puzzled, so I repeat slower this time, "put the bra on please!?"

You slowly start to unbutton your blouse and I get my first glimpse of your naked boobs and they are everything I thought they were, they are a nice size and have large nipples which are stiff and poking out. You reach and take the bra from me and quickly pull it over your boobs. I am right, the bra is a little too small in the cup size and your boobs are pushed up and over the top of the bra giving you a very nice cleavage.

My hard on if now straining against my trousers, I can't help but casually move my hand from the desk and to my cock to adjust it, to try and make it more comfortable. As I look up, I realize that you have followed my hand and probably know that as I shifted on my chair I was adjusting myself. You have a wry grin on your face.

You do the bra up and are just about to put your blouse on when I ask, "Is there anything else that is not regulation uniform??" This time you don't blush.

You look me straight in the eye and say, "umm, yes sir there is?"

"Oh and what is that??" I ask, wondering where this is going.

"I am not wearing regulation panties sir," you state.

I am a little shocked at your blatant response, so I decide to press you on the matter, "oh, and what are you wearing then? You better stand up and show me right this minute Miss Kitten."

To my surprise you just calmly stand and then slowly, bit by bit pull your skirt up, revealing your very shapely legs. I know I am staring at the top of your legs but I can?t tear myself away. As you pull the skirt up the last bit I gasp as your naked smooth shaved pussy comes in to view. As it does, my cock twitches, straining against my trousers again.

I look at you and ask, "why do you not have any pants on Miss Kitten?, you know I am going to have to punish your for not wearing the correct uniform don't you?"

You answer quietly, "I am sorry Sir, I forgot to put them on this morning. Please sir what are you going to do?"

I think for a while, finding it difficult to concentrate with you stood in front of me showing your naked pussy and your boobs overflowing your bra. Finally is comes to me, how I can punish you and get my hands on you at the same time. I look straight at you and say, "Miss Kitten, I am going to give you one spank for each infringement."

With that I rise from my chair and see your eyes immediately open wide at the site of my erection making a tent in my trousers. I walk slowly around the desk and push the chair behind you away slightly and sit down, saying "now, please lie across my lap whilst I give you your punishment. Slowly you lower yourself and lie across my lap, and as you do, your boobs push against my hard on and you stop for a second before you put your weight on me.

Your skirt is still covering you ass, so I reach down and holding the hem slide my hand up the back of your leg and over your ass to reveal your naked ass. You shiver as my hand slides over your ass which makes you rub you boobs against my cock, the feel of your boobs rubbing my cock immediately makes my cock twitch enough for you to notice.

"Are you ready Miss Kitten??" I ask.

You turn slightly to answer, "yes sir?" As you twist your boobs slightly rub against my cock again making it start to throb. I am sure you can feel it because you start to squirm a little and it feels to me like you are now rubbing my cock with your boobs on purpose.

For a few seconds I am lost in the feeling of your boobs rubbing my cock, but I clear my throat and say, "right then here goes." Holding your skirt up out of the way with my right hand, I raise my left hand and bring it down sharply on your bare ass, Smack! You yelp with a mixture of surprise and pain, although not a lot of pain as I deliberately did not smack you hard, but you writhe a bit which just rubs your boobs against my throbbing cock even more.

After the smack, I left my hand on your ass and as you writhe you push back against my hand a little. I am enjoying the sensation of your boobs rubbing my cock, that I am lost from a world for a moment. I realise that you have stopped moving and I clear my mind and concentrate on what I am doing. I raise my hand and again and bring it down sharply on your bare ass, only this time a little harder so you yelp again. This time it?s followed by not only you writhing on my lap but a low moan too. You are again rubbing you boobs against my cock with is now throbbing like mad and aching from straining against my trousers. The sensation is incredible, I can't help thinking that I should not have made you put the bra on, so I could have felt the soft skin of your boobs pressing against my hard cock.