The Head Girl

PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

Coldly I simply reply, "you don't have to do anything you don't want to, the choice is yours."

Miss Kitten

Once again having been caught misbehaving in our dorm late at night I find myself sat on a chair in the Head Teacher's study, shaking a little in worry and anticipation. Mr. Jones is stood here in front of me, his belt and crotch at the height of my head. There is such a large bulge in his trousers and it's only centimeters from my face. I am caught in a dilemma. Tonight he caught me showing Sophia and the other girls a demonstation on how to give a perfect blow job using as a prop the nice pink vibrator I was bought as a birthday present.

He had ordered me straight to his office. I had no time to put on a dressing gown or cover up my nightie. It was more of a negligee, a matching sexy night wear set with very transparent material. Last tima we we had resolved the issue with Mr. Jones giving me a spank for each rule that was broken. I felt so exposed once again in his office. I expected he had called me in to give me the same punishment again. Especially as he had clearly taken a very close look at what I was wearing when he walked into the dorm. Although I knew I was in serious trouble once again I was trembling in sexual anticipation. I had seen the look of lust along with shock and anger cross Mr. Jones' face as he told us off. I felt my pussy quiver when he walked in to shout at us at the thought of what punishment may be to come. Yet, I had not expected to end u in this situation.

As I had been advising the other girls on how to give oral sex, Mr. Jones had challenged me to prove that I knew enough to be qualified to speak and advise on the subject. Lucikily I did have some level of expertise on the subject. Last summer on our visit to our summer house in Spain, one of our neighbours and a good friend of Daddy's had taught me. One day by chance I was left alone in the pool of the villa with him, the rest of the group all had headed into town to purchase food for the evening meal. He was laid on a sun lounger reading a novel. I was diving in the pool, and on one of the dives I rose out from the water and realised the cups on my bakini top had slid down exposing my tits to him. I looked up in shock and horror and we had direct eye contact. He immediately slid his swimming trunks down and showed me the thick erection I had caused him. He then proceeded to show me just perfectly how to satisfy the erection I had given him. At no point that holiday did I have sex with him. I suspected he didn't want the guilt of cheating on his wife completely, or perhaps the blow jobs were just so satisfying he never needed to fuck me.

My mind came back to the situation in front of me. My Head Teachers erection. My desire and need to comply to his demand for a demonstration of a blow job. I looked up straight into his eyes, as I slid a hand up each thigh stopping just before the tent in his pants. I then ran my hands down his stomach towards his belt, undoing it swiftly and unzipping his flies. He had closed his eyes and was looking towards the ceiling when I lightly ran my finger tips up from his balls along the shaft of his cock through his boxers.

As I released his cock from the restraint of his underwear it sprang out forwards so that it was almost touching my face, I thought to myself,"I need to prove myself here, I'm going to really tease, really build him up so he explodes with an A* grade orgasm.

I wet my lips and slid my warm tounge around the head of his cock, which was so hard andswollen the foreskin had slid back already exposing its smooth surface. I ran a figure of eight with my tongue over his head, and then circled around a few times, flicking the end of my tongue on the tender underneath part. I think by this point Mr. Jones was already finding it hard to stand, his legs were shaking slightly and I had hardly started.

I then cupped his balls in my hands and lowered my mouth to lick between the balls up the entire length of his shaft, back to the head.

Oh how I was holding myself back from rubbing my own wet pussy when I finally wrapped my warm wet lips around his stiffness and slowly sucked him deep into my mouth. I was still wriggling my tongue gently against him as I moved my mouth up and down pumping his cock in and out my mouth at an increasing pace.

I could sense his balls tense and realised it was not going to take long to make my Head Teacher cum, so teasingly I slowed right down. Taking special effort to look up and slurp on his cock. This was turning me on so much, just letting him see me kiss his cock and rub the tip around my wet lips. By this point clearly Mr. Jones had come to the point where my teasing became all too much.

He grabbed my hair lightly and started to thrust his cock deep into my mouth at the pace the he wanted to go at. His cock was sliding deep into my throat as I breathed through my nose, so I could continue sucking and taking him at the depth and pace he clearly desired. Suddenly I felt Mr. Jones shudder throughout his body, and the first shot or warm cum filled my mouth. My pussy ached, He pulled his cock out, and while I was swollowing his cum and licking my lips he shot further spurts of cum all over my chest. My tits were covered in his spunk.

Mr, Jones took a moment to regain composure, and within moments his cock was away and he was leaning on his desk as if nothing had happened. "You better clean yourself up May," He said looking me up and down, taking in my tits covered in spunk. Handing me his box of tissues, he gently patted me on the ass which a month ago would have felt inappropriate but now just felt so erotic. "Now go back to your dorm and ensure the girls all behave, yours and their reputations depend on your behaviour these last few terms. When I write your letters of recommendations to the Universities you apply to I'm sure all of you want to be highly commanded, with no misdemeanours at all. Do you understand?"

"Yes Sir," I replied, as I wiped the last drop of cum off my breast with his tissue and put it in his waste basket.

"No go Immediately," Mr Jones commanded. I left hastily. I had enjoyed the whole experience far too much. My own body ached for an orgasm after giving him one.

I almost hold my breath as you sat there trying to decide what you are going to do. Finally you reach out and run your hands up my legs towards my aching cock. Within seconds you have my trousers undone and my cock free from my boxers.

You run your fingers from the base of my balls right up to the tip of my hard cock. I close my eyes and savour the feeling of your hands on my body. You lick the head of my cock, running your tongue around and over the head. The sensation if so intense that my legs almost give way under me. I have to grip the table tightly just to stay standing

The feeling of your tongue circling the head of my cock is incredible. I immediately realise that you know very well how to give a blow job. As I am perched on the edge of my desk with you sucking my dick, I can't help but wonder what it would be like to fuck such a lovely young lady. You start to slowly slide my cock in and out of your hot wet mouth, gradually increasing the pace. With the job that you are doing, I know I am not going to last long, but I want to enjoy the feeling as much as possible for as long as I can last.

You suddenly slow and pull back off my cock, looking into my eyes as you do, your eye full of pure lust. You lick and kiss the head of my cock, but as nice as that is, I want you to take me deeper and faster, I have an urgency to have my cock deep in your mouth. I place my hand gently on the back of your head and push you a little faster and a little deeper, and you comply without a struggle. My cock is now rapidly sliding deep into your mouth, I can feel it banging against the back of your throat with every stroke. I am amazed that you are not gagging as it enters you. I notice that you are quite relaxed and breathing through your nose. I wonder if I should warn you about my impending orgasm.

I can feel the cum bubbling up in my calls and with you doing such an amazing job, I know I am going to cum soon. After several more deep strokes I start to cum, pumping the first few spurts of my cum into your mouth. I let my cock slip from your mouth as I see you swallow the mouthful of cum, whilst I continue to spurt cum all over those lovely boobs. The sight before me is so hot, I don't want to stop. All I want to do is to stand you up and push you over the desk and fuck your tight wet pussy from behind. I know that would be wrong, but the urge to do so is almost over whelming. I make a conscious decision to let you leave my office before I really do something that I know I would regret after, no matter how good it would feel at the time.

I stuff my still stiff cock back into my trousers and do them up, and pass you the box of tissues off my desk. I tell you to clean yourself up, after all I can?' have you leave my office with my cum dripping off your boobs. As you are standing there, I can?t help but gently smack that great ass of yours, and I notice that you don't seem to mind at all. I am still thinking about bending you over the desk and fucking that gorgeous pussy, but I know I shouldn't. I tell you that you had better get back to the dorm, and give you a reminder that you have to control the behaviour of the girls in your charge.

As you leave my office I sit at my desk, I can get the image of you staring up at me, your eyes full of lust with my cock buried deep in your mouth. God, I so want to have you suck my cock again, you really do know what you are doing. I can imagine that there will be a whole dorm of girls that are all as expert as sucking cock as you are, wow, what a thought. No matter what I think about, I always seem to come back to thoughts of fucking you. I imagine how I would have push the items on my desk aside and made you lie across the desk, with your pretty ass pointing up at me revealing that clean shaved pussy. Standing behind you I would gently push two fingers in to your pussy to make sure you were nice and wet, before placing the head of my cock at the opening on your pussy. I place a hand on each side of your hips so I have some leverage to push my cock into your pussy. You would gasp quietly as you feel my cock in your opening and feel me gently pushing as my head stretches your hole wider to accept the head of my cock. You moan a low primal moan as the head slips in to your pussy, as I push deeper into you.

Once I am all the way in, I hold myself there just for a second to let you get used to having a cock buried deep in your pussy, before I slowly pull out until just the head is still in you. This time I push a little harder and a little faster, until again I am deep in you, where I stop for a second. On each stroke I push a little harder and a little faster, and stop for a little less time. After several strokes, I am pushing deep into you in a slow rhythm. You moan loudly as I fully fill you each time I push my cock deep into you. I can feel your pussy muscles tensing around my cock, trying to hold on to it. I slowly start to increase the pace, and before long I am slamming my cock in and out of your pussy that is dripping wet, coating my cock with your pussy juices as I fuck you as hard as I can.

Your moaning is getting louder and higher, and your pussy muscles are gripping tighter, I can feel the orgasm starting to build. I keep pushing in and out, pushing against those tightening muscles, deep in your pussy. I feel you start to tremble and know tou are starting to orgasm, you muscles clamp down tight on my cock, but I continue to push in and out of your hot wet pussy. You tremble uncontrollably and your screams turn in to a deep primal moan as the orgasm washes over you. The muscles in your pussy are now tensing and releasing sending pulses of pleasure down my cock which is too much for me to stand and I can hold on any more. As I cum, I bury my cock deep into your pussy, your pussy muscles milking me of my cum which I am pumping deep in to your pussy. After a moment, I come back to reality, and realise that I have my cock in my hand, and my hand and trousers are covered with my cum once again. I take some tissues and clean myself up and stuff my cock, which is rapidly softening, back in to my boxers and do my flies up.

I sit in my office for a while, wondering how I got myself to this point, and what am I going to do. The thought of fucking Miss Kitten fills my mind, and I can almost feel my unconscious self, plotting a way to make it happen.

May

I found it so hard not to think back to my meetings with my Head Teacher, how erotic my 'tellings off' were. They just excited me too much I found it hard to concentrate. I spent many boring lectures fIantasising back to sucking on his cock in his office, while he looked down on me. I felt such lust. I don't think I had ever felt so aroused. Although I do love the sensation of other girls fingers, tongues and bodies on mine, I had realised that there was an extremely exciting kick to misbehavie so much with a man, and not just any man but Mr. Jones my Head Teacher. As I heaaded back to my dorm that night I was so turned on imagining if we had gone further, how would it have felt if Mr Jones would have dared to have fucked my willing pussy?

My dorm consisted of six girls including me. Angela with her fetish for wearing no underwear, and who I kissed that fatal night Jane bought me the pink vibrator for my birthday. Jane has the most amazing pair of DD breasts and slim waist, and oh I've not yet tasted a girl whose pussy tastes so sweet as hers when I licked it. Sophia, the more timid Brazlian girl who prefers to watch than join in. Then there is Katie, a petite blonde girl who has almost no breasts at all. Under her bra her boobs mainly consist mainly of pale pink nipples on the small mounds. Lastly we have Becky who is a tall beauty, she loves to pleasure others and plays a submissive role when we get into a group session.

This evening we had finished lessons with physical education. It was a trampolining lesson with Mr. Davies. Although we were all decked out in our regulation school sports bras, it was hard not to watch each others breasts rise and fall as we bounced through our practice routines. It was a common joke that Mr. Jones loved teaching us trampolining more than any other sport as he got to enjoy the view of us bouncing, twisting and moving upon his instruction.

The girls changing room consisted of a large communal shower area, rows of lockers and benches to rest our bags on and get changed. Some of the girls headed straight back to the dorms preferring to shower and wash in the dorm bathrooms where the majority of their beauty and wash products were kept. Becky, Jane and I however had opted to shower straight after the lesson. The other two girls having appointments to keep with various tutors shortly after, while I was tasked with hosting the weekly meeting the Head Prefects from the years below mine.

Jane had walked into the shower first, and she was completely naked under the jets of water. I watched as she rubbed soapy body wash across her generous chest, then I stepped under a seperate jet of water myself. Jane came over towards me with the body wash. She chose to squeezy the liquid all over my own chest and then to thrill me further, she raised her hands up and cupped my breasts then started rubbing all over my body. Jane missed no spots, she slid her hand down my back and between my ass cheeks. She soaped up my ass hole and my shaved pussy really well. I couldn't help but let out a low groan as she did this to me. It was at this point Becky walked into the shower room.

As a naturally generous lady with very little inhibitions, Becky headed straight over towards us. She ran a hand down Jane and my bodies. She swirled her fingers around our stomachs towards our pussies, and then at the same time she slid three fingers down each of our wet pussy slits. Now Becky has amazing technique with her fingers. With three fingers she takes the inner labia between her outside two fingers and uses her thrid middle finger to slide right along from your clit to the enterence to your vagina.

It impresses me Becky can manage to do this to Jane and I at the same time, and as my body shudders in response to the intensity of her touch I hear Jane moan out in a low voice "Ooohh, yes, Becky more... Please."

I immediately feel a bit envious of Jane and Becky. I was originally here with Jane, and now she was enjoying Becky more than me. I gently guided Becky's hand from my own pussy and placed it on Jane's chest. I wanted to be more involved, so I knelt down behind Becky. She was too focussed on pleasing Jane when I took control of the situation by running my tongue down from her ass hole, around her cunt opening and then sucked on her swollen bud of a clit. Oh, Becky's pussy was dripping wet. She was clearly extremely turned on, so I pushed two fingers deep into her cunt as far as they would go and then I swirled and moved my fingers around inside her, before starting to push them in and out at an increasing pace.

Becky was moaning in pleasure along with Jane now. Becky whispered out to me huskily, "May, you're going to make me cum soon if you carry on like that... you're distracting me from Jane's pussy."

"Oh Becky" Jane said in a breathless voice, "I'm so close myself, cum for me Becky and take me over the edge."

I carried on plunging two fingers into Becky's cunt as she cried out as she rubbed Jane's clit. She was increasing in the speed that she rubbed Jane as I was increasing the speed that I was licking firmly from Becky's clean ass hole and down to her cunt. I could feel Becky shudder under my touch as I pushed my tongue a few centemeters inside her pussy. Jane was moaning out loud swearing by this point, clearly about to cum herself. I focussed on Becky's clitoris, gently pulling on it with my lips and flicking my tongue and then when I slid fingers in and out her pussy, it took only a few moments for me to feel her warm pussy tense with it's wettness pulsing around my fingers. I moved my head away from her quivering pussy and looked at Jane, who must have cum hard as she was writing around on the floor pulling at her nipples under the jets of water from the showers. She was still clearly in the last waves of her orgasm. I personally, still hadn't cum myself.

Once my two beautiful naked housemates regained some of their composure, they both set upon me. Jane spread my legs and held them apart, as Becky crouched infront of my shaved pussy which was wet with my own juices more than the water from the shower. Becky ran her tongue up the inside of each of my thighs, followed by her finger tips. She chose to focus her finger completely on my clit, twisting and pulling at it as she lent over me now sucking on my erect nipples. Taking each nipple into her mouth and expertly rolling it around with her lis and tongue. Becky sure knew how to give, and my body was giving in. Jane was holding my feet, clearly enjoying the view. I imagine her pussy was too tender from what was clearly an instense orgasm that she had moments ago.

Then suddenly I felt both Jane and Becky's tongues on me. They were licking down from a nipple each side, down my ribs and stomach towards each thigh. Their tongues came at my pussy from each direction and I was over whelmed with the feeling of both their warm tongues flicking at my cunt lips and pulling on them with their teeth so gently. As Jane tugged at my nipple with her fingers it was the final sensation to send me over the edge myself. My hips bucked up, pushing my vagina completely into Becky's face as my body shook with the waves of orgasm. Oh my GOD that was good.