Headmaster
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Headmaster free porn video
The PE teacher had buzzed ahead telling me to expect you. She had not however, prepared me for exactly what I was to be punishing you.
I could easily have lost my job for the punishment I chose for you. Christ, I really should lose my job for the punishment I chose for you.
There was a knock at the door…
“Come!” I shouted.
You stepped inside. You were still wearing your gym clothes…a tight, powder blue top, showing-off those incredible, juicy tits to perfection. Below…you were wearing a tiny gym slip, displaying far too much of your smooth, naked thighs and on your feet, a simple pair of white training shoes.
God you looked good! You looked simply too good.
It could be incredibly difficult being the head of the school at times, particularly when I had to punish naughty sixth form girls. Particularly when I had to punish naughty sixth form girls…like you. Yes you were 18. Yes you were a woman now, but I was your headmaster and, from the moment the thought entered my mind, I truly knew I was in the wrong.
I could feel my cock twitching hard as I looked up at you standing still before me.
I always had a philosophy of punishing my students in a way somehow related to the crime that they had committed, but perhaps in this case I should have forgotten about that, but, as you well know, for right or wrong, I did not.
“So young lady! What have you been up to this time?” I asked.
You stared down at your feet, your cheeks flushing scarlet.
“Well come on girl, I don’t have all day!”
You looked up at me briefly, mumbling something quite inaudible.
“For goodness’ sake girl, speak up! I doubt anything you have done now can be any more shocking than the things you have got up to in the past now can it?”
How wrong could I be?
Finally, you looked up, your eyes piercing my own and said in a full, clear voice…
“I was caught touching myself in the changing room Sir.”
It was my turn to blush now. I stared down at my desk, pointlessly shuffling papers from one place to another and swallowing hard, but there was another more powerful emotion than embarrassment making itself known. My cock was hard and pulsing. I wanted you and as I took a deep, calming breath I decided…I might just have to take you.
I looked up, a little more composed now.
“I see. Well…a young lady of your age should not know about such things, let alone be performing them during school hours. You do realize I will have to punish you don’t you?”
You nodded your head, more than a little nervously.
“As you know…I like to relate your punishment to the deed you have performed. Remember that time you were caught littering and I made you clean the entire school yard?”
Again, a wordless nod.
“Well…I am going to start by humiliating you. If you enjoy touching yourself so much you can show me…”
“But sir…” you protested and really I should have backed down.
“No buts young lady. My mind is quite made up. Now…pull over that chair, remove your underwear and sit down. I want to see what you find so stimulating about that body of yours.”
I watched you, secretly enjoying your discomfort, as you remained standing still in the center of the office, staring at the floor, your cheeks burning red.
“Good God child! Must I do everything for you?”
I stood up, my erection sore and obvious beneath my trousers and came around to the front of the desk. I dragged over a low armchair and placed it next to you.
“Lift up your skirt,” I shouted and with shaking hands you did as you were told, exposing white cotton panties, your little slit tracing a thin line across the tight cloth.
I slipped my fingers beneath the elastic waistband and drew them down quickly, exposing your beautiful smooth pussy.
“What’s this?” I questioned. “Have you been shaving your pus…your vagina?”
“Waxing sir,” you replied, your voice barely more than a whisper.
“Well…I am starting to learn what a truly naughty girl you are and that making you recreate your deviant act may not be nearly enough of a punishment.”
I could’t could I? I wanted nothing more than to take out my big, swollen cock and force you over my desk…press it inside of your tight little cunt, but surely I would lose my job?
I swallowed hard, my dick pleading to be removed and stepped back behind the desk, taking my seat once more.
“Alright young lady…go ahead. Show me exactly what you were doing.”
I watched as you slipped out of your panties entirely and sat yourself down on the edge of the chair. I reveled in your discomfort, your eyes glossy on the brink of tears, your cheeks burning, as you least backwards.
“Well come along girl open your legs!” and you did so.
Your sweet little pussy was spread wide, but not quite wide enough for my liking.
“Oh come now child, wider! Hook your legs over the arms of the chair!” I instructed and it was an amazing sight to behold as you finally obeyed, slowly opening your legs as wide as possible over the arms, slipping your bottom to the very edge of the chair, your pink, swollen pussy lips parting at the last moment and displaying a thin, silvery line of moisture.
It was no good, I could not watch your show without giving myself a little pleasure too, but this would really be all I would do, I lied to myself. I unzipped my fly and pulled out my raging hard-on, hiding it from you behind the desk and slowly, I began to pump.
“KO that’s better, now touch yourself exactly as you were caught doing.”
Tentatively, you reached your right hand between your legs and, taking two fingers, you began to slowly and awkwardly play with yourself. Your eyes were tight shut, through embarrassment or pleasure I could not tell, but I really dido’t care. The sight of you playing with your perfect little pussy was something special and I began to slide my fist up and down my cock harder still.
“Come now, do it properly for goodness sake! I know exactly how naughty little girls touch themselves you know. You will thank me for this punishment one day.”
My last instruction seemed to have switched something in your mind and I watched as you relaxed a little further back into the chair and, biting against your lower lip, you began to caress yourself so beautifully.
Your fingers slid up and down your shiny, wet slit, lubricating them with creamy juice before they slipped under the tiny fold of skin and sought out your swollen clot. You circled round and around, up and down and side to side, sometimes fast sometimes slow. I could see your body jerk as spasms fired through you.
As I fucked my fist hard behind the desk, I realized that you might actually cum for me. I could have cum too, but I knew I should’t let that happen…should I?
You were moaning now, your hips oscillating and giving themselves to the tease of your fingers. Without any prompting from me your other hand slipped between your legs too and I felt a monumental shudder fire from the base of my spine to the tip of my cock as I watched you slip two fingers inside of your cunt, fucking yourself slowly, but deeply as you played with your clot.
This had gone too far already. I knew that with one word from you, I would be in trouble beyond my wildest dreams so, I decided there and then that if my career was over because of one dirty, little schoolgirl, I would make sure it was all worthwhile, make sure she got exactly what she deserved.
“Stop!” I called through parched throat and your eyes sprang open, your fingertips still inside of your pussy. You looked up at me with a nervous expression, worried that you had done something wrong. How could you have? You masturbating for me was just about the prettiest thing I have ever witnessed, but I could not possibly tell you so.
“Stop it girl! You seem to be enjoying yourself far too much. I think you are a bit of a slut aren’t you? I think you give yourself to all the boys don’t you?”
You shook your head quickly, removing your hands and closing your legs.
“I don’t believe you. Do you know what fellatio is? Have you ever put a penis inside of your mouth? Have you ever sucked on a nice, hard cock?”
Again you looked to the floor, but this time rather than shaking your head you nodded…gently and shyly.
“Speak up child, for goodness sake!”
“Yes sir” you muttered.
“I thought as much. Well…as part of your punishment, I think you should suck my cock. Is that understood?”
“Yes bu…”
“Yes what young lady?”
“Yes Sir bu…”
“No buts girl, now sit up straight.” I instructed.
I slipped my dick back into my trousers, even pulling the zip up again before standing and stepping round in front of you. I looked down and saw that your pretty little face was at exactly the right height for my cock.
“Alright then! If you enjoy sex so much you are going to show me exactly what that cute little mouth of yours can do. It may feel a little strange, sucking your headmaster’s dick, but it will be a useful lesson for you to learn. Trust me, it will be strange for me too, but I am willing to make the sacrifice for the good of one of my pupils.”
What a lying bastard I was. This had gone far beyond anything I could have dreary of, but here you were, a beautiful young woman, completely at my mercy. I was abusing my position, I was abusing you and it felt so fucking good.
I unfastened the buckle of my belt, released two trouser buttons, drew down the zipper and dropped them to the floor. I quickly slipped my hands inside the waistband of my shorts and pulled the elastic wide over my erection and dropped them too.
I had to stifle a grin as I watched you staring at my cock, wide-eyed and nervous.
“Suck it,” I ordered and you looked up at me…your eyes dark and moist.
“Don’t worry I will help you,” I said, a little softer now and I ran my fingers into your hair, pulling your head down towards my stiff prick.
I shuddered as I felt my dick press tight against your hot, soft cheek, but I really wanted to see what your delicious, young mouth could do.
I gripped your hair more tightly now, pulling my hips back and directing myself towards your lips. You parted them anxiously as I slowly thrust forwards. Your mouth wans’t wide enough to avoid my cock as I entered you and I exhaled a deep, shuddering breath through my nostrils as I felt your lips brush against me. When I was as deep as I dared to go - I did not’t want you to gag, not yet anyway - I relaxed a little.
“ok child, you have been a very naughty girl indeed. We know that and this is the logical next stage of your punishment. Suck my cock just like you would one of those awful boyfriends of yours and we will forget this matter ever occurred. Alright?”
Again, I had to hold back a moan as I felt you nod against my erection, causing your hot, wet tongue to press against it.
“Good girl. Now…fuck me with your mouth.”
It was pure bliss to feel your lips close against me so tightly, to feel you sucking hard against my cock, drawing saliva into your mouth so that you could give me the slippery, wet blow job you had no doubt given to so many boys before. Slowly you began to draw your head back and forth, my hands still woven into your hair, sucking me so sweetly. Once or twice you pulled a little too far out and the seal was broken, creating an impossibly delicious slurp that caused my muscles to tense and my prick to twitch against the roof of your mouth. It was hell trying to stifle my pleasure. I would be unable to soon enough, but I still had to maintain the pretence that I was forcing you to do this as part of an important lesson you needed to learn. Of course, I was doing it because the sensation of a beautiful young woman sucking my cock was just about as good as it got.
As time went on and you began bobbing your head against me faster and faster, you appeared to relax a little, you seemed to be sucking me with the intention of pleasuring me and not just because I was forcing you. I felt your tongue press against the back of my cock, applying wonderful pressure with every withdrawal. You felt too fucking good and I began to release groans of pleasure with every ass-clenching thrill that shot through my dick. I started to fuck your mouth as you sucked me, thrusting my hips into you, pulling your head onto me, all gently at first, but then harder and faster with greater abandon. A few times I heard you gag as my cock inadvertently pressed against the back of your throat, but you were a good girl, you regained your composure immediately and continued to let me use your mouth for my own selfish gratification.
My prick was so unbelievably tense now, bolts like lightning shot through me with every thrust of my hips, every deep pulsing suck from your lips. You really did know what you were doing. You would occasionally force your head back, letting my cock slip from your mouth and licking at it ravenously as though it were an ice-lolly, but always, you would return it to your hot, wet mouth and always to my thrusts.
I could feel myself drawing nearer and nearer to that inevitable moment. Pulse after shuddering pulse fired through my shaft, causing me to cry out far too loudly. I thought about cumming in your mouth, about withdrawing and shooting across your pretty little face and the image alone caused another massive shudder to erupt through me, but no…it would have been wrong of me. A headmaster should not cum down the throat of one of his pupils and besides…I wanted to fuck that tight little cunt of yours.
I grabbed your head tight, holding you in place and stopping you from sliding your lips any further. I threw my head back and drew quick relaxing breaths before looking down at you. Again, your eyes stared up at me, questioning me, wondering if your punishment could possibly be over, but as I watched you, my cock still held within your mouth, I smiled…
“Well now young lady! I can see you know exactly what you are doing which is a great disappointment to me. It just goes to show what a bad little thing you really are and I am afraid your punishment cannot end quite yet.”
I felt a little moan of yours pulse through my cock. Was it fear or pleasure? I wans’t sure, but it dido’t matter to me either way.
I drew my cock from your mouth, one of the saddest things I have ever had to do, but quite necessary in order to move on to the next stage of your punishment.
I pulled my shorts and trousers up, fastening them loosely around my swollen cock - I hand’t quite finished using it on you just yet - and held out my hands.
You reached up and I guided you to a standing position. You looked up at me through large, glassy eyes and I, in turn, smiled gently down at you.
“Alright now, you are receiving your punishment very well so far, but it is not over just yet. You still need to know what a naughty little slut you are. I know that disciplining you in this manner is perhaps a little childish for someone of your age, but I have a feeling it might prove effective. Now place your hands on the desk like this
I could easily have lost my job for the punishment I chose for you. Christ, I really should lose my job for the punishment I chose for you.
There was a knock at the door…
“Come!” I shouted.
You stepped inside. You were still wearing your gym clothes…a tight, powder blue top, showing-off those incredible, juicy tits to perfection. Below…you were wearing a tiny gym slip, displaying far too much of your smooth, naked thighs and on your feet, a simple pair of white training shoes.
God you looked good! You looked simply too good.
It could be incredibly difficult being the head of the school at times, particularly when I had to punish naughty sixth form girls. Particularly when I had to punish naughty sixth form girls…like you. Yes you were 18. Yes you were a woman now, but I was your headmaster and, from the moment the thought entered my mind, I truly knew I was in the wrong.
I could feel my cock twitching hard as I looked up at you standing still before me.
I always had a philosophy of punishing my students in a way somehow related to the crime that they had committed, but perhaps in this case I should have forgotten about that, but, as you well know, for right or wrong, I did not.
“So young lady! What have you been up to this time?” I asked.
You stared down at your feet, your cheeks flushing scarlet.
“Well come on girl, I don’t have all day!”
You looked up at me briefly, mumbling something quite inaudible.
“For goodness’ sake girl, speak up! I doubt anything you have done now can be any more shocking than the things you have got up to in the past now can it?”
How wrong could I be?
Finally, you looked up, your eyes piercing my own and said in a full, clear voice…
“I was caught touching myself in the changing room Sir.”
It was my turn to blush now. I stared down at my desk, pointlessly shuffling papers from one place to another and swallowing hard, but there was another more powerful emotion than embarrassment making itself known. My cock was hard and pulsing. I wanted you and as I took a deep, calming breath I decided…I might just have to take you.
I looked up, a little more composed now.
“I see. Well…a young lady of your age should not know about such things, let alone be performing them during school hours. You do realize I will have to punish you don’t you?”
You nodded your head, more than a little nervously.
“As you know…I like to relate your punishment to the deed you have performed. Remember that time you were caught littering and I made you clean the entire school yard?”
Again, a wordless nod.
“Well…I am going to start by humiliating you. If you enjoy touching yourself so much you can show me…”
“But sir…” you protested and really I should have backed down.
“No buts young lady. My mind is quite made up. Now…pull over that chair, remove your underwear and sit down. I want to see what you find so stimulating about that body of yours.”
I watched you, secretly enjoying your discomfort, as you remained standing still in the center of the office, staring at the floor, your cheeks burning red.
“Good God child! Must I do everything for you?”
I stood up, my erection sore and obvious beneath my trousers and came around to the front of the desk. I dragged over a low armchair and placed it next to you.
“Lift up your skirt,” I shouted and with shaking hands you did as you were told, exposing white cotton panties, your little slit tracing a thin line across the tight cloth.
I slipped my fingers beneath the elastic waistband and drew them down quickly, exposing your beautiful smooth pussy.
“What’s this?” I questioned. “Have you been shaving your pus…your vagina?”
“Waxing sir,” you replied, your voice barely more than a whisper.
“Well…I am starting to learn what a truly naughty girl you are and that making you recreate your deviant act may not be nearly enough of a punishment.”
I could’t could I? I wanted nothing more than to take out my big, swollen cock and force you over my desk…press it inside of your tight little cunt, but surely I would lose my job?
I swallowed hard, my dick pleading to be removed and stepped back behind the desk, taking my seat once more.
“Alright young lady…go ahead. Show me exactly what you were doing.”
I watched as you slipped out of your panties entirely and sat yourself down on the edge of the chair. I reveled in your discomfort, your eyes glossy on the brink of tears, your cheeks burning, as you least backwards.
“Well come along girl open your legs!” and you did so.
Your sweet little pussy was spread wide, but not quite wide enough for my liking.
“Oh come now child, wider! Hook your legs over the arms of the chair!” I instructed and it was an amazing sight to behold as you finally obeyed, slowly opening your legs as wide as possible over the arms, slipping your bottom to the very edge of the chair, your pink, swollen pussy lips parting at the last moment and displaying a thin, silvery line of moisture.
It was no good, I could not watch your show without giving myself a little pleasure too, but this would really be all I would do, I lied to myself. I unzipped my fly and pulled out my raging hard-on, hiding it from you behind the desk and slowly, I began to pump.
“KO that’s better, now touch yourself exactly as you were caught doing.”
Tentatively, you reached your right hand between your legs and, taking two fingers, you began to slowly and awkwardly play with yourself. Your eyes were tight shut, through embarrassment or pleasure I could not tell, but I really dido’t care. The sight of you playing with your perfect little pussy was something special and I began to slide my fist up and down my cock harder still.
“Come now, do it properly for goodness sake! I know exactly how naughty little girls touch themselves you know. You will thank me for this punishment one day.”
My last instruction seemed to have switched something in your mind and I watched as you relaxed a little further back into the chair and, biting against your lower lip, you began to caress yourself so beautifully.
Your fingers slid up and down your shiny, wet slit, lubricating them with creamy juice before they slipped under the tiny fold of skin and sought out your swollen clot. You circled round and around, up and down and side to side, sometimes fast sometimes slow. I could see your body jerk as spasms fired through you.
As I fucked my fist hard behind the desk, I realized that you might actually cum for me. I could have cum too, but I knew I should’t let that happen…should I?
You were moaning now, your hips oscillating and giving themselves to the tease of your fingers. Without any prompting from me your other hand slipped between your legs too and I felt a monumental shudder fire from the base of my spine to the tip of my cock as I watched you slip two fingers inside of your cunt, fucking yourself slowly, but deeply as you played with your clot.
This had gone too far already. I knew that with one word from you, I would be in trouble beyond my wildest dreams so, I decided there and then that if my career was over because of one dirty, little schoolgirl, I would make sure it was all worthwhile, make sure she got exactly what she deserved.
“Stop!” I called through parched throat and your eyes sprang open, your fingertips still inside of your pussy. You looked up at me with a nervous expression, worried that you had done something wrong. How could you have? You masturbating for me was just about the prettiest thing I have ever witnessed, but I could not possibly tell you so.
“Stop it girl! You seem to be enjoying yourself far too much. I think you are a bit of a slut aren’t you? I think you give yourself to all the boys don’t you?”
You shook your head quickly, removing your hands and closing your legs.
“I don’t believe you. Do you know what fellatio is? Have you ever put a penis inside of your mouth? Have you ever sucked on a nice, hard cock?”
Again you looked to the floor, but this time rather than shaking your head you nodded…gently and shyly.
“Speak up child, for goodness sake!”
“Yes sir” you muttered.
“I thought as much. Well…as part of your punishment, I think you should suck my cock. Is that understood?”
“Yes bu…”
“Yes what young lady?”
“Yes Sir bu…”
“No buts girl, now sit up straight.” I instructed.
I slipped my dick back into my trousers, even pulling the zip up again before standing and stepping round in front of you. I looked down and saw that your pretty little face was at exactly the right height for my cock.
“Alright then! If you enjoy sex so much you are going to show me exactly what that cute little mouth of yours can do. It may feel a little strange, sucking your headmaster’s dick, but it will be a useful lesson for you to learn. Trust me, it will be strange for me too, but I am willing to make the sacrifice for the good of one of my pupils.”
What a lying bastard I was. This had gone far beyond anything I could have dreary of, but here you were, a beautiful young woman, completely at my mercy. I was abusing my position, I was abusing you and it felt so fucking good.
I unfastened the buckle of my belt, released two trouser buttons, drew down the zipper and dropped them to the floor. I quickly slipped my hands inside the waistband of my shorts and pulled the elastic wide over my erection and dropped them too.
I had to stifle a grin as I watched you staring at my cock, wide-eyed and nervous.
“Suck it,” I ordered and you looked up at me…your eyes dark and moist.
“Don’t worry I will help you,” I said, a little softer now and I ran my fingers into your hair, pulling your head down towards my stiff prick.
I shuddered as I felt my dick press tight against your hot, soft cheek, but I really wanted to see what your delicious, young mouth could do.
I gripped your hair more tightly now, pulling my hips back and directing myself towards your lips. You parted them anxiously as I slowly thrust forwards. Your mouth wans’t wide enough to avoid my cock as I entered you and I exhaled a deep, shuddering breath through my nostrils as I felt your lips brush against me. When I was as deep as I dared to go - I did not’t want you to gag, not yet anyway - I relaxed a little.
“ok child, you have been a very naughty girl indeed. We know that and this is the logical next stage of your punishment. Suck my cock just like you would one of those awful boyfriends of yours and we will forget this matter ever occurred. Alright?”
Again, I had to hold back a moan as I felt you nod against my erection, causing your hot, wet tongue to press against it.
“Good girl. Now…fuck me with your mouth.”
It was pure bliss to feel your lips close against me so tightly, to feel you sucking hard against my cock, drawing saliva into your mouth so that you could give me the slippery, wet blow job you had no doubt given to so many boys before. Slowly you began to draw your head back and forth, my hands still woven into your hair, sucking me so sweetly. Once or twice you pulled a little too far out and the seal was broken, creating an impossibly delicious slurp that caused my muscles to tense and my prick to twitch against the roof of your mouth. It was hell trying to stifle my pleasure. I would be unable to soon enough, but I still had to maintain the pretence that I was forcing you to do this as part of an important lesson you needed to learn. Of course, I was doing it because the sensation of a beautiful young woman sucking my cock was just about as good as it got.
As time went on and you began bobbing your head against me faster and faster, you appeared to relax a little, you seemed to be sucking me with the intention of pleasuring me and not just because I was forcing you. I felt your tongue press against the back of my cock, applying wonderful pressure with every withdrawal. You felt too fucking good and I began to release groans of pleasure with every ass-clenching thrill that shot through my dick. I started to fuck your mouth as you sucked me, thrusting my hips into you, pulling your head onto me, all gently at first, but then harder and faster with greater abandon. A few times I heard you gag as my cock inadvertently pressed against the back of your throat, but you were a good girl, you regained your composure immediately and continued to let me use your mouth for my own selfish gratification.
My prick was so unbelievably tense now, bolts like lightning shot through me with every thrust of my hips, every deep pulsing suck from your lips. You really did know what you were doing. You would occasionally force your head back, letting my cock slip from your mouth and licking at it ravenously as though it were an ice-lolly, but always, you would return it to your hot, wet mouth and always to my thrusts.
I could feel myself drawing nearer and nearer to that inevitable moment. Pulse after shuddering pulse fired through my shaft, causing me to cry out far too loudly. I thought about cumming in your mouth, about withdrawing and shooting across your pretty little face and the image alone caused another massive shudder to erupt through me, but no…it would have been wrong of me. A headmaster should not cum down the throat of one of his pupils and besides…I wanted to fuck that tight little cunt of yours.
I grabbed your head tight, holding you in place and stopping you from sliding your lips any further. I threw my head back and drew quick relaxing breaths before looking down at you. Again, your eyes stared up at me, questioning me, wondering if your punishment could possibly be over, but as I watched you, my cock still held within your mouth, I smiled…
“Well now young lady! I can see you know exactly what you are doing which is a great disappointment to me. It just goes to show what a bad little thing you really are and I am afraid your punishment cannot end quite yet.”
I felt a little moan of yours pulse through my cock. Was it fear or pleasure? I wans’t sure, but it dido’t matter to me either way.
I drew my cock from your mouth, one of the saddest things I have ever had to do, but quite necessary in order to move on to the next stage of your punishment.
I pulled my shorts and trousers up, fastening them loosely around my swollen cock - I hand’t quite finished using it on you just yet - and held out my hands.
You reached up and I guided you to a standing position. You looked up at me through large, glassy eyes and I, in turn, smiled gently down at you.
“Alright now, you are receiving your punishment very well so far, but it is not over just yet. You still need to know what a naughty little slut you are. I know that disciplining you in this manner is perhaps a little childish for someone of your age, but I have a feeling it might prove effective. Now place your hands on the desk like this
Latisha
- 29.05.2021
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- Category:
- Straight Sex
