A MOST WICKED HEADMASTER
- 4 years ago
- 28
- 0
Jennifer And The Headmaster free porn video
Sitting in my car daydreaming, listening to the music and waiting for my Daughter to come out of school, there is a tap at the window. It startles me and I jump, looking out I see the Headmaster, Mike Johnson so I put down the window and he apologizes for surprising me. He informs me that Sarah will be a little late because she has some project she wants to finish up and then asks if I would like to join him in his office for tea while we wait. I accept his invitation and he opens the door to let me out, as he stands and holds the door he gets a good look at my bare legs, compliments of my short skirt. I swing my legs out to face him as he offers his hand to assist me to stand up and in doing so I part them slightly so he can see right up to my skimpy damp see through panties. I pretend like I have no idea that I did that and he pretends not to notice. I have suspected for some time that Mike is infatuated with me because he is always finding ways to come out and chat with me while I wait for Sarah. He tries so hard to get me to stay for a bit and talk and I figure he delays Sarah on purpose. We make small talk on the way to his office, covering things like the weather and local news. As we ascend the steps up to the administration building he lags behind and lets me go ahead, I know this is so he can get a good look at my full bottom swaying back and forth under my short skirt.
Once inside his office we sit on a small couch up against the big windows that look out onto a large courtyard and he brings me some tea. I thank him and as I take a sip I casually point out that it has been a long time since I was in the Headmasters office. Oh, he replies and what was the reason that you would be called to the Headmasters office. Well I say, it is too embarrassing to tell you that, no please tell me he says I will not make fun of you. Little does he know that I am making it all up because I went to a public school and corporal punishment had long been abolished. I pretend to be shy and with a little more prodding from Mike I finally start to tell him my made up story. Basically I repeat a nice favourite erotic tale that I have read and masturbated to many times and secretly want to come true. The story involves a young rebellious teenager who more than once gets sent to the office for six strokes of the cane to try to modify her behaviour. I describe in great detail how awkward it is for me to have to keep bending over and removing my panties so that mean Headmaster could beat my bare bottom. I keep glancing at Mike and I can see that he is eating up this concocted story and listening to every word I say, I also notice that he is getting a little uncomfortable sitting. Mike commends me on sharing my experiences with him and points out that I am such a lovely young woman, he never would have imagined that I would need to be spanked. There is that word “SPANKED” it almost screams in my head, the one word that will make my pussy cream, I did not use the word in my story but he chose to use it. Of all the words to describe punishment “SPANKED” only describes erotic sexual bliss to me. I looked at him and taking my time so he could drink in his reflection in my eyes, I responded using an innocent little girl voice saying, yes Sir sometimes I need to be SPANKED, I emphasized. I could see his lip quivering trying to digest what I just said but then the buzzer sounded in the school and shocked both of us back to reality. I make a quick excuse that I need to get Sarah home and then get to work. He questions why I work in the evening and tell him as I am heading out the door that I am a cocktail waitress at an exclusive private club. I meet Sarah at the car and while I am driving her home I plot my next step with Mike Johnson, the die has been cast and I just need to play this out right, he could be the one that is for sure.
The next day I arrive at the school a little earlier to give Mike and I some time to talk before the end of the school day. I no sooner pull up in front and he is out like a shot to greet me and help me out of the car again. I am the first to speak and I tell him that I want him to know more about Sarahs and my history. This time I am wearing an even more provocative dress, it is short but also very snug fitting and with my tiny waist shows my full bottom in perfect symmetry. Again we walk up to his office and I can almost feel his eyes burning into my bottom as I slowly climb the stairs to make sure he gets a good long look. We sit on the couch and while crossing my legs the dress pulls up to reveal my thighs right up to the side of my bare hip. I pretend to try and pull my dress down as though I am concerned with my modesty but I am actually adjusting it to give him the best view possible. The first thing he asks is why I am a cocktail waitress and also wonders how close Sarah and I are in age, pointing out that the other mothers are a lot older than me. Well I begin by telling him about my job and how I flirt with the wealthy men to get bigger tips, it is the best job I can get and actually pays pretty good so that I can keep Sarah in a private school. The next part I have genuine difficulty telling him and he quickly picks up on my nervousness. He tells me that I don't have to explain but I reply that no I want to tell you because no one else knows the real story. As I begin I notice that he is no longer looking at my legs but into my eyes that have begun to moisten with deep rooted emotion.
Where to begin I say to him, Yes There is only f******n years between me and Sarah, I got pregnant from the boy next door at a very young age obviously. We would play together a lot and he used to spank me every time we played, I enjoyed the play spankings and that was all we did but then just before he moved away he wanted to do “it” just once. Well that was all it took and now I have my most precious thing on earth named Sarah. I went on to explain that my mother basically raised both of us and I have her to thank for Sarahs wonderful sparkling personality and intelligence. Mike could see that what I was telling him was dredging up a great deal of buried thoughts and feelings and as I finished I actually began to cry. This part was not planned as I really did start to cry and I buried my face into his broad shoulders while letting loose years of pent up emotion and secrecy. Mike did not know what to do so he put his arms around me to comfort me and I snuggled in close so he could hold me tight. Through my tears and sniffles I explained that he was the first person I ever told this to and he thanked me for trusting him so much with this obviously very personal information. Mike said that I should dry my eyes and get cleaned up because the school bell would be ringing shortly and we don't want people to see you leaving the Headmasters office crying. Oh my yes I exclaimed that would get them talking wouldn't it and I grinned at him. Mike stopped me as I was leaving his office, he said tomorrow the whole school is going on an all day field trip and we need to talk more. He continued saying, you need firm discipline in your life and I don't think your occupation is setting a good example for Sarah and the home life she needs and deserves. He also said that he wanted me to come back to his office exactly at noon and for me to think about my behaviour this evening so that tomorrow we can decide what should be done to set my life back on track. He was glaring at me as I thought to myself, I was suppose to be directing where this was going and now he is, I actually felt a little nervous wondering what he meant by firm discipline but the tingling in my pussy told a different story. I nodded my head and said, yes Sir I will be here and will think very hard about what you asked. I headed out of his office and he watched me walking down the hall way, I realized I presented a very sultry image with my heels clicking on the polished marble floor and him staring at my bottom flexing up and down under the tight short skirt.
I did think very hard about what I wanted and needed, I spent most of the night with my fingers working in an out of my pussy dreaming about it. In the morning I took great care in selecting the perfect outfit for what I was expecting and hoping would happen in his office. I dressed in a nice conservative tartan skirt that came down to just above the knees and put on a long sleeved white blouse then just ankle socks and flats. Reflecting back from the mirror was a proper school girl but I needed to be a little daring so reaching under my skirt I removed my panties so if and hopefully when he gets to that stage he will get a little surprise. I take a moment to stroke a finger in between my labia and the slick fluid that coats my finger tells me that I am ready.
Mike also could not sleep last night wondering if this sexy young tease would actually be interested in a man twice her age. The vision of the sweetest bottom and legs he had ever set eyes on kept playing over and over in his mind. All night the erections would not subside as he kept stroking his cock and ejaculating thinking of this woman that had captivated his mind and heart. He had waited years for such a hypnotic amazing creature to enter his life and he needed to seize the day.
I nervously drive into the parking lot and hurry into the school looking back to make sure no one noticed. The halls and classrooms were empty like he said as everyone was away on a field trip. I enter the secretary’s office and knocked on his door, I hear a commanding voice say enter and as I did I suddenly felt like a genuine naughty school girl being sent for punishment. Mike is sitting behind his desk doing some paper work and he motions for me to sit in the chair in front of his desk. I sit anxiously waiting for him to address me when I notice three school canes and a leather paddle resting on the side of his desk. My heart starts to race knowing these are intended for me, as I sit staring at them I fail to notice Mike looking at me. He clears his throat and makes me jump, He asks me if I thought about my life style and behaviour and how it could be corrected. Yes I reply but before I can say anything else, Mike begins to inform me how we would proceed this morning. Mike says, the way I see it you need a good old fashioned caning on your bare bottom, normally a young girl would get six but since you are a mature woman I am inclined to give you twenty four strokes with the senior cane. I sit quietly hanging on his every word as he continues I expect you to take your punishment like a big girl and I hope I do not have to restrain you. My mind is flooded with images of him tying me down to whip me and my pussy is responding by getting wetter with every word. Mike looks and me and asks if I understand and agree with him, I just nod yes.
Mike rises from behind his desk and walks around to the front, he takes my hand and directs me to the front of his desk. He puts his hand into the small of my back and lowers me face down onto the desk. I feel him start to gather the hem of my skirt and raise it up my thighs to rest on my back. Jennifer! He exclaims, you are not wearing any panties, you naughty, naughty girl, just for that I am going to add another dozen to the count and you will now get thirty six strokes with the senior cane. I was beginning to regret this decision but it was too late now. I see Mike reach for the cane and after a few practice swings in the air he places it against my trembling flawless white globes. He takes a few seconds to admire the creamy flesh of the most perfect spank-able bottom he had ever seen but he had a mission to accomplish and must stay the course. The only thing I hear is my heavy aroused breathing then swoosh, WHACK, oh shit I say out loud, then another WHACK, damn I grit my teeth. Two more hard fast ones that cause me to bolt upright, Mike pushes me back down saying he will restrain me if he has to. He keeps his left had on my lower back holding me down and applies a half dozen fast strokes extracting a high pitched squeal from me. Mike steps back to view his handy work and asks me if I need to be tied, no Sir I reply I will be good and accept the punishment freely. Good girl he replies that is what I wanted to hear and the next few minutes are the longest of my life. The moan of the cane slicing the air and the sickening thud it makes as it sinks into me swollen welted flesh reverberates around the room, Oh gawd I wail it hurts so bad and I burst into tears, crying opening and bawling loudly but I stay in position as he beats my bare bottom.
I am slumped across his desk at the conclusion of my punishment, Mike stands me up and holds me tight, stroking my hair and telling me what a good girl I am. Now he says this is what you need, a good caning every week and I intend to be the one giving it to you plus you also need to quit your job and give Sarah the proper home life she needs. I look imploring through blurry tear filled eyes and say but how will I support her without an income, that is easy said Mike, if you were the wife of a school Headmaster, money would not be an issue. If you accept my proposal there is more that I will demand from you, I will expect to fill your mouth and pussy with my cock every day and you will learn to worship my cock. I will spank you whenever I want and whenever I feel you need it. He continued with the conditions saying, I have set up an account for you on a website called Xhamster, your log-in is spankingjenny and you will go on that site every day to watch, read and learn how to worship a mans cock and see how other people get whipped. Men will want to chat with you and that is fine, their erotic words will make you wet and horny and ready for me when I come home. You and Sarah will want for nothing and she will have access to the best schools in the country to accomplish whatever she wants.
So Jennifer I await your answer, you do not have to tell me right away, you can think about it if you need to but you know exactly what is in store for you. If I just yelled “YES” that just wouldn't be enough I needed to show him how much I needed and wanted him, so sinking down to my knees I unbuckled his trousers and started my new life.
Once inside his office we sit on a small couch up against the big windows that look out onto a large courtyard and he brings me some tea. I thank him and as I take a sip I casually point out that it has been a long time since I was in the Headmasters office. Oh, he replies and what was the reason that you would be called to the Headmasters office. Well I say, it is too embarrassing to tell you that, no please tell me he says I will not make fun of you. Little does he know that I am making it all up because I went to a public school and corporal punishment had long been abolished. I pretend to be shy and with a little more prodding from Mike I finally start to tell him my made up story. Basically I repeat a nice favourite erotic tale that I have read and masturbated to many times and secretly want to come true. The story involves a young rebellious teenager who more than once gets sent to the office for six strokes of the cane to try to modify her behaviour. I describe in great detail how awkward it is for me to have to keep bending over and removing my panties so that mean Headmaster could beat my bare bottom. I keep glancing at Mike and I can see that he is eating up this concocted story and listening to every word I say, I also notice that he is getting a little uncomfortable sitting. Mike commends me on sharing my experiences with him and points out that I am such a lovely young woman, he never would have imagined that I would need to be spanked. There is that word “SPANKED” it almost screams in my head, the one word that will make my pussy cream, I did not use the word in my story but he chose to use it. Of all the words to describe punishment “SPANKED” only describes erotic sexual bliss to me. I looked at him and taking my time so he could drink in his reflection in my eyes, I responded using an innocent little girl voice saying, yes Sir sometimes I need to be SPANKED, I emphasized. I could see his lip quivering trying to digest what I just said but then the buzzer sounded in the school and shocked both of us back to reality. I make a quick excuse that I need to get Sarah home and then get to work. He questions why I work in the evening and tell him as I am heading out the door that I am a cocktail waitress at an exclusive private club. I meet Sarah at the car and while I am driving her home I plot my next step with Mike Johnson, the die has been cast and I just need to play this out right, he could be the one that is for sure.
The next day I arrive at the school a little earlier to give Mike and I some time to talk before the end of the school day. I no sooner pull up in front and he is out like a shot to greet me and help me out of the car again. I am the first to speak and I tell him that I want him to know more about Sarahs and my history. This time I am wearing an even more provocative dress, it is short but also very snug fitting and with my tiny waist shows my full bottom in perfect symmetry. Again we walk up to his office and I can almost feel his eyes burning into my bottom as I slowly climb the stairs to make sure he gets a good long look. We sit on the couch and while crossing my legs the dress pulls up to reveal my thighs right up to the side of my bare hip. I pretend to try and pull my dress down as though I am concerned with my modesty but I am actually adjusting it to give him the best view possible. The first thing he asks is why I am a cocktail waitress and also wonders how close Sarah and I are in age, pointing out that the other mothers are a lot older than me. Well I begin by telling him about my job and how I flirt with the wealthy men to get bigger tips, it is the best job I can get and actually pays pretty good so that I can keep Sarah in a private school. The next part I have genuine difficulty telling him and he quickly picks up on my nervousness. He tells me that I don't have to explain but I reply that no I want to tell you because no one else knows the real story. As I begin I notice that he is no longer looking at my legs but into my eyes that have begun to moisten with deep rooted emotion.
Where to begin I say to him, Yes There is only f******n years between me and Sarah, I got pregnant from the boy next door at a very young age obviously. We would play together a lot and he used to spank me every time we played, I enjoyed the play spankings and that was all we did but then just before he moved away he wanted to do “it” just once. Well that was all it took and now I have my most precious thing on earth named Sarah. I went on to explain that my mother basically raised both of us and I have her to thank for Sarahs wonderful sparkling personality and intelligence. Mike could see that what I was telling him was dredging up a great deal of buried thoughts and feelings and as I finished I actually began to cry. This part was not planned as I really did start to cry and I buried my face into his broad shoulders while letting loose years of pent up emotion and secrecy. Mike did not know what to do so he put his arms around me to comfort me and I snuggled in close so he could hold me tight. Through my tears and sniffles I explained that he was the first person I ever told this to and he thanked me for trusting him so much with this obviously very personal information. Mike said that I should dry my eyes and get cleaned up because the school bell would be ringing shortly and we don't want people to see you leaving the Headmasters office crying. Oh my yes I exclaimed that would get them talking wouldn't it and I grinned at him. Mike stopped me as I was leaving his office, he said tomorrow the whole school is going on an all day field trip and we need to talk more. He continued saying, you need firm discipline in your life and I don't think your occupation is setting a good example for Sarah and the home life she needs and deserves. He also said that he wanted me to come back to his office exactly at noon and for me to think about my behaviour this evening so that tomorrow we can decide what should be done to set my life back on track. He was glaring at me as I thought to myself, I was suppose to be directing where this was going and now he is, I actually felt a little nervous wondering what he meant by firm discipline but the tingling in my pussy told a different story. I nodded my head and said, yes Sir I will be here and will think very hard about what you asked. I headed out of his office and he watched me walking down the hall way, I realized I presented a very sultry image with my heels clicking on the polished marble floor and him staring at my bottom flexing up and down under the tight short skirt.
I did think very hard about what I wanted and needed, I spent most of the night with my fingers working in an out of my pussy dreaming about it. In the morning I took great care in selecting the perfect outfit for what I was expecting and hoping would happen in his office. I dressed in a nice conservative tartan skirt that came down to just above the knees and put on a long sleeved white blouse then just ankle socks and flats. Reflecting back from the mirror was a proper school girl but I needed to be a little daring so reaching under my skirt I removed my panties so if and hopefully when he gets to that stage he will get a little surprise. I take a moment to stroke a finger in between my labia and the slick fluid that coats my finger tells me that I am ready.
Mike also could not sleep last night wondering if this sexy young tease would actually be interested in a man twice her age. The vision of the sweetest bottom and legs he had ever set eyes on kept playing over and over in his mind. All night the erections would not subside as he kept stroking his cock and ejaculating thinking of this woman that had captivated his mind and heart. He had waited years for such a hypnotic amazing creature to enter his life and he needed to seize the day.
I nervously drive into the parking lot and hurry into the school looking back to make sure no one noticed. The halls and classrooms were empty like he said as everyone was away on a field trip. I enter the secretary’s office and knocked on his door, I hear a commanding voice say enter and as I did I suddenly felt like a genuine naughty school girl being sent for punishment. Mike is sitting behind his desk doing some paper work and he motions for me to sit in the chair in front of his desk. I sit anxiously waiting for him to address me when I notice three school canes and a leather paddle resting on the side of his desk. My heart starts to race knowing these are intended for me, as I sit staring at them I fail to notice Mike looking at me. He clears his throat and makes me jump, He asks me if I thought about my life style and behaviour and how it could be corrected. Yes I reply but before I can say anything else, Mike begins to inform me how we would proceed this morning. Mike says, the way I see it you need a good old fashioned caning on your bare bottom, normally a young girl would get six but since you are a mature woman I am inclined to give you twenty four strokes with the senior cane. I sit quietly hanging on his every word as he continues I expect you to take your punishment like a big girl and I hope I do not have to restrain you. My mind is flooded with images of him tying me down to whip me and my pussy is responding by getting wetter with every word. Mike looks and me and asks if I understand and agree with him, I just nod yes.
Mike rises from behind his desk and walks around to the front, he takes my hand and directs me to the front of his desk. He puts his hand into the small of my back and lowers me face down onto the desk. I feel him start to gather the hem of my skirt and raise it up my thighs to rest on my back. Jennifer! He exclaims, you are not wearing any panties, you naughty, naughty girl, just for that I am going to add another dozen to the count and you will now get thirty six strokes with the senior cane. I was beginning to regret this decision but it was too late now. I see Mike reach for the cane and after a few practice swings in the air he places it against my trembling flawless white globes. He takes a few seconds to admire the creamy flesh of the most perfect spank-able bottom he had ever seen but he had a mission to accomplish and must stay the course. The only thing I hear is my heavy aroused breathing then swoosh, WHACK, oh shit I say out loud, then another WHACK, damn I grit my teeth. Two more hard fast ones that cause me to bolt upright, Mike pushes me back down saying he will restrain me if he has to. He keeps his left had on my lower back holding me down and applies a half dozen fast strokes extracting a high pitched squeal from me. Mike steps back to view his handy work and asks me if I need to be tied, no Sir I reply I will be good and accept the punishment freely. Good girl he replies that is what I wanted to hear and the next few minutes are the longest of my life. The moan of the cane slicing the air and the sickening thud it makes as it sinks into me swollen welted flesh reverberates around the room, Oh gawd I wail it hurts so bad and I burst into tears, crying opening and bawling loudly but I stay in position as he beats my bare bottom.
I am slumped across his desk at the conclusion of my punishment, Mike stands me up and holds me tight, stroking my hair and telling me what a good girl I am. Now he says this is what you need, a good caning every week and I intend to be the one giving it to you plus you also need to quit your job and give Sarah the proper home life she needs. I look imploring through blurry tear filled eyes and say but how will I support her without an income, that is easy said Mike, if you were the wife of a school Headmaster, money would not be an issue. If you accept my proposal there is more that I will demand from you, I will expect to fill your mouth and pussy with my cock every day and you will learn to worship my cock. I will spank you whenever I want and whenever I feel you need it. He continued with the conditions saying, I have set up an account for you on a website called Xhamster, your log-in is spankingjenny and you will go on that site every day to watch, read and learn how to worship a mans cock and see how other people get whipped. Men will want to chat with you and that is fine, their erotic words will make you wet and horny and ready for me when I come home. You and Sarah will want for nothing and she will have access to the best schools in the country to accomplish whatever she wants.
So Jennifer I await your answer, you do not have to tell me right away, you can think about it if you need to but you know exactly what is in store for you. If I just yelled “YES” that just wouldn't be enough I needed to show him how much I needed and wanted him, so sinking down to my knees I unbuckled his trousers and started my new life.
Elissa
- 29.05.2021
- 27
- 0
