Headmaster

You were bent forwards now, legs splayed, your ass and pussy only just covered by your tiny gymslip, but not for long. I reached forwards and drew the skirt up - a finger gently tracing along the line between your cheeks - and left it gathered around your waist. I heard you cry out as you felt yourself exposed to me. By now you will have realised what a tough headmaster I could be and you must have been more than a little scared as to what was to come next.

I stared at you, stroking my cock through my trousers. It was a wonderful sight. Your tight little pussy, firm and juicy in between your smooth, round ass cheeks. It was at that moment that I finally admitted to myself that I was going to fuck you, but not quite yet. You really did need punishing and I was willing to wait for my pleasure in order to teach you the lesson that you deserved.

“This may sting just a little, but it will perhaps stop you from playing with that sticky little cunt of yours,” and with that I brought my palm swishing down hard against your right cheek, hearing you cry out with the shock of my strike and watching your flesh, flush purple. Again I brought my hand slapping down against you, the opposite cheek this time, and again you yelped in pain. I alternated my strikes from one cheek to the next, your flesh a deep pink and itchy sore with the blood that rushed to the tortured skin.

It was such a pretty site to see you flinch, your ass cheeks tensing and releasing every time I struck you. I began to gently stroke at one cheek as I slapped hard at the other, my hand almost involuntarily slipping downwards and inwards. I’m really not sure that I was aware of what I was doing, but before long I found myself rubbing my hand against your pussy as I continued to spank you, telling you just what a naughty little girl you were. My left hand was sticky with your pussy juice and I realised you were actually enjoying yourself. This only made me slap you harder and quicker as I now slid two fingers inside your tight little slit and fingered you back and forth. You continued to cry out with every stinging strike of my hand, but now there was something a little desperate, a little animalistic about your moans.

Finally I stepped back from you, breathing hard and looking at the mess I had made of your poor behind. My fingers were glossy with your cum. I was about to slip them between my lips when I had a better idea.

“You really are too much girl!” I chastised. “I am trying to teach you a lesson…to show you the error of your ways and I find you are still preoccupied with your own selfish, sexual desires. You are actually enjoying your punishment. Look…” With that I brought my sticky fingers around to your mouth and smeared your juices against your lips. You moaned and opened your mouth, sucking my fingers in and licking them clean. You were amazing…a filthy young woman who was obviously incapable of knowing the difference between right and wrong. I could see there would only be one way to teach you the consequences of your actions.

“I am afraid I am going to have to fuck you now,” I said and my stomach lurched as I heard the little cry you released at my words. “If you are going to be a dirty little slut and play with your cunt in school, men are going to want you, they are going to need to stick their hard dicks inside of you and it is my duty as headmaster to show you exactly what that would be like.”

I once again, stepped behind you and stared at the beauty of your semi-naked form bent over my desk. I unfastened my trousers and dropped them and my shorts to the floor and positioned myself behind you, taking an ass cheek in each hand and parting you wide.

“Now, this may hurt a little. Your pussy is so young and tight and my cock is so big and hard right now, but you must learn your lesson and if you relax you may even begin to enjoy it a little.”

I pushed my dick towards you. It was just about as hard and erect as it ever had been. Consequently, I had to release a hand from your behind in order to grab at it and direct it towards your entrance. I slid it up and down your sticky-wet slit a few times, coating the head in your creamy juices and lubricating it nicely before pressing forwards. You were so wet, your lips so engorged with blood, that it slipped into you quite nicely at first, but soon, the tautness of your young flesh resisted and I felt your cunt tight around my cock. I was going to have to stretch you wide, but you really did need to feel the kind of thing you were letting yourself in for.

I released my dick and once again spread your hot, scarlet cheeks, staring at myself on the brink of entering you. One final time I wondered if it was not too late to stop, to let you go and pretend this never happened, but how could I? I would be neglecting my duties as the head of the school and missing the opportunity to fuck your beautiful, tight pussy.

I looked down and swallowed as I rammed my hips forwards, stretching your pussy wide and slamming my hard cock deep inside of you in one powerful movement. I cried out as I felt your, hot, wet cunt sucking me so tightly, but it must have been quite inaudible beneath the squeal that you released as I forced my way inside of you. I held myself still, desperately trying to relax, to catch my breath, but you felt just too damned good.

I began to withdraw, but not completely. As my head pressed against your opening I slid my cock back inside of you, tracing the line of your pussy wall, my cock rubbing hard behind your clit as I began to increase my rhythm. I pumped in and out of you, slowly and steadily at first, but increasing my pace as time moved on. You felt so fucking good and as I looked down at my hard shaft, glistening with your cream as it slipped in and out of your cunt, I had to use all of my reserves not to spurt deep inside of you there and then.

I released your ass-cheeks and pressed my hands to your slim waist and began to fuck you harder and harder, your bottom pounding into my abdomen with every thrust, my balls slapping against your clit. Harder still I thrust. I became aware of your own little cries and saw you biting against one of your fingers as I slammed my stiff cock in and out of you, time and time again.

I could hear your breaths increasing in speed, your cries increasing in pitch and realised you were close to cumming. I could feel my own orgasm near. My body was sending huge tremors through my shaft to the very tip of my cock. I knew that I was so close to shooting deep inside of you, but I couldn’t could I? You were one of my pupils!

I thrust harder and harder, faster and faster, hearing you sob with pleasure, feeling my cock ready to explode. In the last instant I realised I could not possibly explode inside of you…that would just be wrong, so what if you didn’t orgasm? this was a punishment not lovemaking. So, despairingly I drew my cock entirely out of you, grabbing you by the hips and spinning you around. I pressed your ass hard against the edge of the table, opening your thighs wide, just in time, as I grabbed my cock and aimed it towards you.

With an earth shuddering cry I began to shoot jet after jet of hot, sticky cum all across your lower abdomen and your wonderful little pussy. I cried out as time and time again my dick pumped, coating your cunt in my semen.

Finally, I slowed and relaxed. I collapsed back into the armchair, my eyes closed as the gravity of what I had just done presented itself. I wondered exactly how much trouble I had let myself in for. Could I deny it? Say it was just the fantasy of a lonely young woman? That was the moment that I heard you. Tiny gasps moving into full-grown moans, you cursing vulgarly with frustrated pleasure. I opened my eyes and there you were, still leaning against the desk, your eyes tight shut and your head thrown back, your teeth playing aggressively with your lips. My eyes moved downwards and I was taken aback to see what you were doing. You were teasing your cunt right in front of me, rubbing your cum spattered clit for all it was worth. I had unfairly left you without your orgasm and so…you were just going to take it for yourself.

It was an amazing sight, your fingers coated in our combined juices, so slippery as you teased your pussy hard in front of me. I could see by your expression, hear by your moans that you were so close and it was a delight to watch you bring your sopping wet cunt off before me.

Your little hand was rubbing so very quickly, your brow furrowed as your climax began to take hold. You gasped harder with every breath, but your slippery fingers would not give up until…finally you released a huge, desperate cry and held your fingers still against yourself as your orgasm racked your body. You had made yourself cum in front of your headmaster without caring. Yes it was mostly my fault that you were in this state, but you had finished yourself off with absolutely no regard for what I might think.

I thought you were wonderful.

As your body slowed and relaxed I quickly stood, pulling up my trousers and tucking myself away before sitting back down behind my desk and returning to my role as head of the school.
“You really are too much girl!” I chastised. “I am trying to teach you a lesson…to show you the error of your ways and I find you are still preoccupied with your own selfish, sexual desires. You are actually enjoying your punishment. Look…” With that I brought my sticky fingers around to your mouth and smeared your juices against your lips. You moaned and opened your mouth, sucking my fingers in and licking them clean. You were amazing…a filthy young woman who was obviously incapable of knowing the difference between right and wrong. I could see there would only be one way to teach you the consequences of your actions.

“I am afraid I am going to have to fuck you now,” I said and my stomach lurched as I heard the little cry you released at my words. “If you are going to be a dirty little slut and play with your cunt in school, men are going to want you, they are going to need to stick their hard dicks inside of you and it is my duty as headmaster to show you exactly what that would be like.”

I once again, stepped behind you and stared at the beauty of your semi-naked form bent over my desk. I unfastened my trousers and dropped them and my shorts to the floor and positioned myself behind you, taking an ass cheek in each hand and parting you wide.

“Now, this may hurt a little. Your pussy is so young and tight and my cock is so big and hard right now, but you must learn your lesson and if you relax you may even begin to enjoy it a little.”

I pushed my dick towards you. It was just about as hard and erect as it ever had been. Consequently, I had to release a hand from your behind in order to grab at it and direct it towards your entrance. I slid it up and down your sticky-wet slit a few times, coating the head in your creamy juices and lubricating it nicely before pressing forwards. You were so wet, your lips so engorged with blood, that it slipped into you quite nicely at first, but soon, the tautness of your young flesh resisted and I felt your cunt tight around my cock. I was going to have to stretch you wide, but you really did need to feel the kind of thing you were letting yourself in for.

I released my dick and once again spread your hot, scarlet cheeks, staring at myself on the brink of entering you. One final time I wondered if it was not too late to stop, to let you go and pretend this never happened, but how could I? I would be neglecting my duties as the head of the school and missing the opportunity to fuck your beautiful, tight pussy.

I looked down and swallowed as I rammed my hips forwards, stretching your pussy wide and slamming my hard cock deep inside of you in one powerful movement. I cried out as I felt your, hot, wet cunt sucking me so tightly, but it must have been quite inaudible beneath the squeal that you released as I forced my way inside of you. I held myself still, desperately trying to relax, to catch my breath, but you felt just too damned good.

I began to withdraw, but not completely. As my head pressed against your opening I slid my cock back inside of you, tracing the line of your pussy wall, my cock rubbing hard behind your clit as I began to increase my rhythm. I pumped in and out of you, slowly and steadily at first, but increasing my pace as time moved on. You felt so fucking good and as I looked down at my hard shaft, glistening with your cream as it slipped in and out of your cunt, I had to use all of my reserves not to spurt deep inside of you there and then.

I released your ass-cheeks and pressed my hands to your slim waist and began to fuck you harder and harder, your bottom pounding into my abdomen with every thrust, my balls slapping against your clit. Harder still I thrust. I became aware of your own little cries and saw you biting against one of your fingers as I slammed my stiff cock in and out of you, time and time again.

I could hear your breaths increasing in speed, your cries increasing in pitch and realised you were close to cumming. I could feel my own orgasm near. My body was sending huge tremors through my shaft to the very tip of my cock. I knew that I was so close to shooting deep inside of you, but I couldn’t could I? You were one of my pupils!

I thrust harder and harder, faster and faster, hearing you sob with pleasure, feeling my cock ready to explode. In the last instant I realised I could not possibly explode inside of you…that would just be wrong, so what if you didn’t orgasm? this was a punishment not lovemaking. So, despairingly I drew my cock entirely out of you, grabbing you by the hips and spinning you around. I pressed your ass hard against the edge of the table, opening your thighs wide, just in time, as I grabbed my cock and aimed it towards you.

With an earth shuddering cry I began to shoot jet after jet of hot, sticky cum all across your lower abdomen and your wonderful little pussy. I cried out as time and time again my dick pumped, coating your cunt in my semen.

Finally, I slowed and relaxed. I collapsed back into the armchair, my eyes closed as the gravity of what I had just done presented itself. I wondered exactly how much trouble I had let myself in for. Could I deny it? Say it was just the fantasy of a lonely young woman? That was the moment that I heard you. Tiny gasps moving into full-grown moans, you cursing vulgarly with frustrated pleasure. I opened my eyes and there you were, still leaning against the desk, your eyes tight shut and your head thrown back, your teeth playing aggressively with your lips. My eyes moved downwards and I was taken aback to see what you were doing. You were teasing your cunt right in front of me, rubbing your cum spattered clit for all it was worth. I had unfairly left you without your orgasm and so…you were just going to take it for yourself.

It was an amazing sight, your fingers coated in our combined juices, so slippery as you teased your pussy hard in front of me. I could see by your expression, hear by your moans that you were so close and it was a delight to watch you bring your sopping wet cunt off before me.

Your little hand was rubbing so very quickly, your brow furrowed as your climax began to take hold. You gasped harder with every breath, but your slippery fingers would not give up until…finally you released a huge, desperate cry and held your fingers still against yourself as your orgasm racked your body. You had made yourself cum in front of your headmaster without caring. Yes it was mostly my fault that you were in this state, but you had finished yourself off with absolutely no regard for what I might think.

I thought you were wonderful.

As your body slowed and relaxed I quickly stood, pulling up my trousers and tucking myself away before sitting back down behind my desk and returning to my role as head of the school.

“Well young lady! I hope you have learnt a valuable lesson here today. Clean yourself up at the basin there and we’ll say no more about the matter okay?”

Once again you nodded shyly and set about tidying yourself. When you were done you turned to face me, eyes once more staring towards the ground.

“Alright, you are a good girl really. Now…run along back to class and I don’t expect to see you in my office for quite some time. Is that understood?”

You muttered some kind of affirmation and disappeared from my office, leaving me to contemplate the inevitable fallout from my choice of punishment.

That was five days ago and the school board still has not rung me to demand my resignation, the police have not arrived to question my abuse of power. In fact, I had heard nothing from you until five minutes ago when my secretary, Jane buzzed my intercom…

“There’s that young lady here to see you headmaster…the one you had to punish last week.” My heart skipped a beat.

“Oh? Who has sent her?”

“No one headmaster, that’s the strange thing. She says she has been a bad girl again and needs to see you about her punishment.”

“I understand. She is a very badly behaved child that one and does require a lesson or two. Give me five minutes to finish my paperwork Jane and then send her on through. Oh…and Jane, you might as well go home early. I may be quite some time with that young lady…she is a very naughty girl indeed”