Megan and Mallory s Birthday Spankings
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My first summer job before I enter my senior year in High School is working as a courier for Allister Atwater of Atwater and Sons Barristers and Solicitors. I deliver legal documents to customers either on foot or by taxi depending on how far away they are. Regular Clients seem pleased when they see me arrive at their offices with documents, mainly because I dress in cute little summer dresses and flirt with the older executives. The older gentlemen are always teasing me saying that maybe what I need is a good spanking, I giggle and wink at them as I walk away swinging my hips back and forth.
Mr. Atwater called me into his office after a couple of weeks went by to have a talk with me. He started off by saying how pleased he was with my performance and that he got many complimentary calls from our high profile clients. I was in the middle of thanking him when he cut me off saying that he also was concerned with how I was flirting with the clients. I began to blush as he read off some of the emails he had received from others who had seen my actions and thought it might not be professional. He also pointed out that the content of my flirting always involved teasing them about spanking. His next question was very blunt as he asked me if I wanted the older male clients to spank me as part of our delivery service. He then just sat there waiting for my response, which made me very uncomfortable. I replied to his last question by asking first if I was going to be fired, he replied no. I then went on to tell him how I do have this fascination for spanking and want desperately to get a good hard spanking but probably from only one man who I like and trust. Mr. Atwater thanked me for my honesty but added that I would have to stop flirting with the clients.
A few days went by and I received an assignment to deliver sensitive legal documents Friday afternoon to Headmaster Harold Windsor at London’s Finishing School for Girls. Harold Windsor was getting divorced and had been very frustrated for some time over it, something that the bare bottoms of the young Ladies at the school were well aware of as he dealt out more and more punishments. Mr. Atwater had planned this assignment very carefully hoping that this encounter between me and Harold would turn into something much more enjoyable and without either one of us aware of the scheme. He knew Harold Windsor personally and also how much he enjoyed whipping young ladies so he figured Harold would not be able to resist my charms. I had very specific instructions for time of day that I was to be there and the attire that I was supposed to wear. I was to arrive precisely at the end of the last class and I was sent to the uniform shop to be outfitted like a girl from the school, this included shoes, knee socks, mid-thigh tartan skirt, white blouse, blue tie and blue blazer. Looking in the mirror made me think what a naughty school girl I looked like and as usual my thoughts drifted to images of me getting spanked as I let a hand stray under the skirt to tease my clit. I was to dress like this so I would fit in and not attract any unwanted attention as I entered the campus.
I arrive on time and wait outside the Headmasters office where I can hear the unmistakable sound of a girl getting a good thrashing. The sound of a cane slicing the air and the girl’s muffled cries makes my pussy tingle with excitement as I long to slip a hand under my skirt. When the young girl with tears flowing and rubbing her bottom scurries out, I enter the office. Introducing myself as Jennifer, I tell him that I have some papers for him as I place a large envelope on his desk but before I can say anything else the Headmaster tells me to raise my skirt and bend over the heavy chair that the previous girl was just over. I immediately figure that he thinks I am a student sent for punishment and try to explain but Harold Windsor just gets more angry and tells me that I will get double if I do not do as I am told. Again I interject but Harold just says, right then that will be an even dozen instead of six. Realizing that arguing with him is ineffective; I take up position behind the back of the chair, besides how bad could it be.
As I bend over my school skirt rises up over my full bottom and gives Mr. Harold Windsor a view he was not expecting. He thinks to himself, this young pretty girl has a lovely flawless, full, well-developed bottom, not the usual ones he sees and wonders how such a young girl could have such an inviting voluptuous bottom as he feels his cock start to rise in his trousers. I feel him take hold of my panties and slide them down my thighs to my ankles. He pauses for a moment absorbing the view of a nice plump, moist, hairless pussy peeking out from the gap at the top of my thighs. Tempting thoughts race through his mind as the head of his cock starts to do the thinking for him but he manages to push them out of his mind and takes up position to my left side, tapping the cane on my bare bottom. Harold Windsor makes a mental note that the girl is not wearing regulation panties but figures that an additional six strokes would be cruel. He quickly slides a hand down the front of his trousers to adjust his rapidly hardening and swelling cock because it was getting painful. Then without wasting anymore time he raises the cane up and whips the gorgeous bare bottom presented before him.
The first stroke that strikes my bottom makes me think this is OK but then a moment later the pain sinks in and spreads as I gasp. Quickly he applies the second and third and so on until all dozen strokes have turned my bottom into a flaming painful welted mess. Harold noticed that this young girl did not cry out like all the other girls but whimpered and moaned when the cane struck her fleshy bottom. I am quietly crying and whimpering as the pain continues to radiate and sink into my flesh and am relieved when he tells me to stand up. He asks me to stand in front of his desk while he takes the large envelope I had placed on his desk earlier. It is a minute or two before he looks at it and it gives me the opportunity to really look at Mr. Windsor. He was easily three times my age but very handsome, probably over six feet tall and obviously quite fit. It also gave me time to appreciate the wonderful warm feeling that was flooding my body from my still burning bottom plus the sting in my backside was causing the juices in my aroused pussy to flow with new found sensations. I watched as Mr. Windsor looked in horror at the letterhead of the paper work and realizing that at that moment he remembered that the Law firm would be sending me over. I have never seen a man tremble like this as he started to apologize over and over pleading for me not to sue or report him and how he would do anything to make it up to me for this misunderstanding. Well as the pleasing warmth from my bottom continued to spread I could see no harm in what just took place but took the opportunity to get to know Mr. Windsor a little better. I wiped the tears from my eyes and replied that if he took me out to dinner then all would be forgiven. He looked stunned and relieved at the same time,” really” he responded, “I would be happy to take you to the finest restaurant”. I want to find out more about this handsome man and hopefully taste more of his cane so we make plans for Saturday evening. He says he will pick me up, he also states that we will drop by an exclusive Dress shop so I can pick out a suitable dress for our date.
I am nervous as a cat all day Saturday wondering what is in store for me and the reminder of the still sensitive welts on my bottom make me masturbate constantly. I dress sensibly in a cute summer dress that I know Mr. Windsor will like. I see him pull up in his Jaguar so I hurry out to meet him and give him a big hug, he tells me how lovely I look as he helps me into the car. Stepping into the low riding sports car causes my legs to part and my dress to ride up giving him a good look between my legs. This makes his cock stiffen again as he drinks in the vision of the insides of my smooth silky thighs and sheer skimpy panties. I am oblivious to the mental torture that my actions and looks are imposing on this man. As we drive to the Dress shop that he mentioned we partake in small nervous conversation about nothing at all, mostly just to break the tension plus he asks me to just call him Harold and Not Mr. Windsor.
The Dress shop is a cute upscale store and as soon as we enter two lovely older ladies take me away as Harold makes arrangements for payment and states that price is not an issue. The older ladies are so nice to me asking what I need and for what kind of event. I tell them about our evening and the restaurant plus I confide in them that I am planning to spend the night with him so I need something very classy and a little sexy. They pick out this beautiful long gown that is a little see through and will give him a hint as to my figure underneath and coupled with some lovely high heels I look much older than I am. When I exit the dressing room so Harold can see me his jaw drops in amazement and thanks the Ladies for the transformation. I am stunned when I accidentally see the bill which is three thousand pounds. I do not let on that I saw the bill but I give him another big hug and a kiss on the cheek saying thank you.
Entering the Restaurant, all eyes are on me and Harold is very aware of it. The observant waiter sits us out on the patio where we can have some privacy and avoid the stares of the other patrons. The evening slips by quickly as we chat about my and his work plus world events and the usual small talk. That changes when he asks again if everything is Ok between us considering the severe spanking he gave me. I reply that I am glad it happened because it has given me a chance to get to know him. Besides I add, I really didn’t mind getting the cane from you. Harold smiles and tells me that he had considered adding another six strokes because I was not wearing regulation panties. I sit there contemplating my next move then I say, so that means that I am still due six strokes, will I be getting them latter this evening? Harold has to take a minute for what I said to sink in and replies; yes I think latter this evening would be perfect to give you the remainder. I ask him if there are any other indiscretions on my behalf that he could deal with at the same time, like tardiness and bad language maybe some homework not done on time. Harold sees where this little game of mine is going and simply says that he will deal with me when he gets me home but rest assured it will be substantially more than six. He adds that I should think about my naughty behaviour and confess to him when we get home so the proper punishment can be dealt out. He smiles when he sees me blushing as we both know full well where this evening is headed. Walking out of the restaurant, Harold offers me his arm. I cuddle up close to him as we wait for the valet to deliver his Jag. I shiver a little and Harold asks if I am cold, I smile sweetly up at him and reply no just nervous. Hmmmm he says, yes that is understandable but just remember you are safe with me and I will not do anything to you that you are uncomfortable with. That made me feel very warm inside and I pulled myself in close to him.
Harold’s house is a nice country cottage just outside London, lovely gardens and a nice quiet secluded setting. We enter this cozy house and he directs me into a spare room where he has some suitable school girl uniforms that he says will no doubt enhance the evening. The uniforms are similar to the ones at the Girls School but the Tartan skirts are so short they don’t quite cover my bottom. After I am suitably attired I meet him out in the living room where he has set up a tall whipping bench with straps to secure a young lady so she can’t move. He looks me over then smiles at my appearance asking why I have been sent to see him. This is my clue that the adventure had begun so I put on a little attitude saying that my Math teacher didn’t like the length of my skirt so I told him off. Harold reminds me to address him as Sir and then says that he has had many complaints about my behaviour and work ethics. He goes on to say that most girls under his domain get six strokes of the cane with their panties on but since there are so many reports on me it is only just that he should give me twenty four strokes of the cane on my bare bottom. I pretend to be infuriated and complain that his ruling is unfair and the other teachers just have it in for me. Mr. Windsor notices that in the punishment book I actually already have six strokes due to me so informs me that the count will now be thirty strokes on the bare and while restrained. I take a deep breath and change my attitude rather quickly, sorry Sir I apologize Sir please not any more than thirty Sir.
Harold realizes that the limit had been reached and agrees that thirty strokes of the cane on the bare bottom while restrained will be sufficient. Placing a hand in the small of my back, He directs me over to the front of the whipping apparatus and gently bends me forward until my feet are off the floor and my full weight is supported by it. My short skirt easily rides up over my bottom exposing me completely to his gaze and also the fact that my thin panties are completely soaked with my juices. Before he ties me down he removes my soaked panties and without me seeing him he brings them up to his nose to get a good whiff of my fragrant young pussy. The scent triggers his prehistoric urges and makes his already rigid cock stiffen even more. Harold sets about the task of restraining me by fastening my wrists to the far side, placing a large belt tightly over my back but when he fastens my ankles he spreads my legs far apart. It takes all Harold’s will power to not defile me on the spot, he thinks to himself that there will be plenty of time latter to satisfy his urges.
Harold stands beside me gently running his hand over my bare bottom and up and down the backs of my thighs. He runs his hand up the inside of my thigh and as he draws a finger over my clit and dripping pussy I let out a long low moan. Harold whispers into my ear that it is time for me to learn what real punishment is like. With my bottom still tender from yesterday’s caning I yelp on the very first stroke, the second one makes me squeal out in pain and the third has me bursting into tears. Well Harold says that did not take long for you to cry but you are going to cry a lot more as he whips me harder. After about a dozen strokes I am panting and sweating but the fire in my bottom and thighs is working its way to my pussy. Harold can see the juices dripping from my swollen aroused pussy so he pauses for a minute to stroke my clit and finger me. I try to hump his finger and cum but he stops just short of me having an orgasm. He goes back to whipping my bottom and thighs until I am crying out in pain and lust and before he reaches thirty strokes I cum and squirt onto the floor. I lay passively over the whipping bench as he applies the last six strokes not really knowing how much longer he will whip me. When he is finished I assumed he would untie me but instead he stepped up behind with his large stiff cock nudging between my pussy lips, then with one long thrust he buries his cock deep inside my dripping slippery pussy. He takes long methodical strokes as his massive cock fills and stretches my insides, with each thrust making me grunt. Harold’s orgasm comes quickly as he has been putting off ejaculating for a few days, his balls are full and his built up cum shoots deep into my pussy. I am in desperate need to orgasm as Harold pulls his still pulsating and dripping cock out of my ravished young virgin pussy. What I don’t yet know is this is just one step on how he plans on building my arousal to such a fevered state that I will do anything and everything for him.
He unties me from the whipping apparatus and my legs are so weak that he carries me into the bathroom where he starts a nice warm shower so we can clean up. He holds me close while we shower and gently massages my body under the running water. Again I feel his cock stiffen as it lies up against my sore swollen bottom and with one hand he teases my breasts and with the other he teases my clit. I just start to feel a massive orgasm come over me and he stops fingering me, I swear I was going to lose my mind. He turns off the shower and we dry ourselves off then he takes me into the bedroom where he gives me a cute little nightie to wear. He then leads me into the living room where he lights a fire in the fireplace and we settle down in a big comfortable chair to watch and warm ourselves in front of it. As we sit down and I cuddled up under his strong arm I move up to give him a big kiss. I kiss him like I am going to devour him, sucking the breath out of him and running my tongue all over the inside of his mouth. He pulls me away after a few minutes of necking and tells me that he has a lot more in store for me. I am nodding and saying yes please, not really knowing what but just wanting him so bad.
He has me stand up in front of the fireplace and he goes over to a cupboard to retrieve a thick leather strap. Right away I plead that I would not be able to take anymore punishment on my bottom. Harold smiles and says it is not for my bottom then tells me to get on my knees and hold out my hands, palms up. I do as he says without even thinking about and as he takes off his robe I see this fit naked man with a renewed massive erection. Harold asks me if I have ever taken a man’s cock into my mouth. No of course not I reply and before tonight I have never actually had a man touch me in any way. Harold looked surprised and questioned my virginity which I confirmed that tonight was my first time. Harold apologized for taking me the way he did not realizing that I was still a virgin, I was quick to reassure him that no apology was necessary. He hummed to himself and then said Ok we will continue as planned. He told me told me that he was going to give me the strap on my hands; six hard strokes on each hand until I am crying again and then he would have me suck his cock while I was still crying. I was so aroused and wanted him so bad that I would agree to anything he said, so I just nodded yes. I knelt and held out my hands, he was quick to smack one and I pulled it away, he barked at me not to pull away or move them in anyway or I would get double. I knew he meant business when he says double so I replied, yes Sir sorry Sir and presented my hands again. This is a pain I was not prepared for, the sting and pain of the strap striking my palms had me crying and howling loudly. I resolved that I would hold my position and I did, but after six strokes on each hand I was a quivering tearful mess. Just like he said he held my head asking me to open my mouth so he could slide his cock in. He pushed it right to the back of my throat which made me immediately gag; sorry he whispered that is something that you will need to learn, but not tonight. He pulled it back until just the head was in my mouth but even that was all I could take. He stroked his cock and told me to run my tongue around the head and said that when he orgasms he wants me to swallow all his cum. I find the texture of his cock head to be so pleasing and the little bit of cum that is leaking out is actually quite pleasant. Harold tells me that he is about to cum so I prepare to take it all. The gush of cum almost overwhelms me but I make every effort to swallow it all, it happens so fast that I don’t really get a chance to savour it. Harold slumps back into the chair and while I watch him recover from the strain he instructs me to lay on my back with my legs spread and masturbate for him. Now this is something I know how to do, so laying back I begin to tease and finger my clit. It is so erotic to have a man watch me masturbate that my first orgasm comes quickly and thankfully too. I am approaching my second orgasm which is building to a much more powerful one when Harold slips down between my thighs and starts to lick my pussy. The sensation of his tongue on my clit and lips is so powerful that I blurt out, “oh my gawd”. This actually brings a little chuckle from Harold as he sets to extract as many orgasms from me as possible. I lost count of how many times I came but when I was exhausted and spent and Harold’s face was soaked in my juices he moved up to kiss me and let me taste my cum on his face. At this point in the evening we retired to bed and both doze off in each other’s arms.
Sunday morning I awake to the feeling of a big erect cock pushing against my still sore and swollen bottom. I roll over to face him and kiss him deeply; He has a strap lying on the bed so smiling at him I roll onto my tummy. No Harold says, this is not for your bottom as he turns me over onto my back and spreads my legs wide apart. He takes the strap and begins whipping the insides of my thighs. This is another kind of intense pain but this time it only serves to inflame and arouse my passion. I look into Harold’s eyes as he whips me, he is smiling at me as my eyes water with lust and my breathing quickens. He paints the insides of my thighs a deep crimson before centering the strap right onto my pussy. Each smack makes me jerk and moan, smack after smack makes my juices flow and brings me close to orgasm. Harold times it so that just as I am about to cum he kneels between my thighs and plunges his engorged cock deep into me. I wrap my legs around him and hold on tight as I cum from his writhing monster serpent that is pumping and squirming deep in my belly. For the rest of the day I have Harold’s cock either in my mouth or in my pussy, he tried to put it up my bum but his big cock just didn’t fit. All day I practiced trying to take his cock down my throat and with a little help from a numbing throat spray we succeeded. As night began to fall Harold told me that he would take me to work in the morning and if I wanted he would pick me up at the end of the workday to bring me back here again. I was ecstatic and gave him a big hug and kiss saying absolutely, nothing would give me more pleasure, so we went to bed with his cock buried in me for the rest of the night.
In the morning I dressed in the summer dress that I was wearing when he first picked me up and we headed off to work. Mr. Atwater just happened to be looking out into the parking lot when we pulled up and we got out. He was pleased when he saw me give Harold a big long kiss before he got back in his car and headed out. Mr. Atwater called me into his office when he saw me at my desk and noticed I was walking a little stiffly. He had a big smile on his face as I sat down in front of his desk and asked me how my weekend went, he then added that he knew Harold Windsor very well and also had a pretty good idea what happened to me. I Smiled at him and asked if he had set it up, he replied that he only created the opportunity and the rest was all us. Well I confessed to Mr. Atwater that things could not have turned out better and my need and fascination for spanking was being well taken care of. Good girl Jennifer he said, and sent me back to my desk.
Mr. Atwater called me into his office after a couple of weeks went by to have a talk with me. He started off by saying how pleased he was with my performance and that he got many complimentary calls from our high profile clients. I was in the middle of thanking him when he cut me off saying that he also was concerned with how I was flirting with the clients. I began to blush as he read off some of the emails he had received from others who had seen my actions and thought it might not be professional. He also pointed out that the content of my flirting always involved teasing them about spanking. His next question was very blunt as he asked me if I wanted the older male clients to spank me as part of our delivery service. He then just sat there waiting for my response, which made me very uncomfortable. I replied to his last question by asking first if I was going to be fired, he replied no. I then went on to tell him how I do have this fascination for spanking and want desperately to get a good hard spanking but probably from only one man who I like and trust. Mr. Atwater thanked me for my honesty but added that I would have to stop flirting with the clients.
A few days went by and I received an assignment to deliver sensitive legal documents Friday afternoon to Headmaster Harold Windsor at London’s Finishing School for Girls. Harold Windsor was getting divorced and had been very frustrated for some time over it, something that the bare bottoms of the young Ladies at the school were well aware of as he dealt out more and more punishments. Mr. Atwater had planned this assignment very carefully hoping that this encounter between me and Harold would turn into something much more enjoyable and without either one of us aware of the scheme. He knew Harold Windsor personally and also how much he enjoyed whipping young ladies so he figured Harold would not be able to resist my charms. I had very specific instructions for time of day that I was to be there and the attire that I was supposed to wear. I was to arrive precisely at the end of the last class and I was sent to the uniform shop to be outfitted like a girl from the school, this included shoes, knee socks, mid-thigh tartan skirt, white blouse, blue tie and blue blazer. Looking in the mirror made me think what a naughty school girl I looked like and as usual my thoughts drifted to images of me getting spanked as I let a hand stray under the skirt to tease my clit. I was to dress like this so I would fit in and not attract any unwanted attention as I entered the campus.
I arrive on time and wait outside the Headmasters office where I can hear the unmistakable sound of a girl getting a good thrashing. The sound of a cane slicing the air and the girl’s muffled cries makes my pussy tingle with excitement as I long to slip a hand under my skirt. When the young girl with tears flowing and rubbing her bottom scurries out, I enter the office. Introducing myself as Jennifer, I tell him that I have some papers for him as I place a large envelope on his desk but before I can say anything else the Headmaster tells me to raise my skirt and bend over the heavy chair that the previous girl was just over. I immediately figure that he thinks I am a student sent for punishment and try to explain but Harold Windsor just gets more angry and tells me that I will get double if I do not do as I am told. Again I interject but Harold just says, right then that will be an even dozen instead of six. Realizing that arguing with him is ineffective; I take up position behind the back of the chair, besides how bad could it be.
As I bend over my school skirt rises up over my full bottom and gives Mr. Harold Windsor a view he was not expecting. He thinks to himself, this young pretty girl has a lovely flawless, full, well-developed bottom, not the usual ones he sees and wonders how such a young girl could have such an inviting voluptuous bottom as he feels his cock start to rise in his trousers. I feel him take hold of my panties and slide them down my thighs to my ankles. He pauses for a moment absorbing the view of a nice plump, moist, hairless pussy peeking out from the gap at the top of my thighs. Tempting thoughts race through his mind as the head of his cock starts to do the thinking for him but he manages to push them out of his mind and takes up position to my left side, tapping the cane on my bare bottom. Harold Windsor makes a mental note that the girl is not wearing regulation panties but figures that an additional six strokes would be cruel. He quickly slides a hand down the front of his trousers to adjust his rapidly hardening and swelling cock because it was getting painful. Then without wasting anymore time he raises the cane up and whips the gorgeous bare bottom presented before him.
The first stroke that strikes my bottom makes me think this is OK but then a moment later the pain sinks in and spreads as I gasp. Quickly he applies the second and third and so on until all dozen strokes have turned my bottom into a flaming painful welted mess. Harold noticed that this young girl did not cry out like all the other girls but whimpered and moaned when the cane struck her fleshy bottom. I am quietly crying and whimpering as the pain continues to radiate and sink into my flesh and am relieved when he tells me to stand up. He asks me to stand in front of his desk while he takes the large envelope I had placed on his desk earlier. It is a minute or two before he looks at it and it gives me the opportunity to really look at Mr. Windsor. He was easily three times my age but very handsome, probably over six feet tall and obviously quite fit. It also gave me time to appreciate the wonderful warm feeling that was flooding my body from my still burning bottom plus the sting in my backside was causing the juices in my aroused pussy to flow with new found sensations. I watched as Mr. Windsor looked in horror at the letterhead of the paper work and realizing that at that moment he remembered that the Law firm would be sending me over. I have never seen a man tremble like this as he started to apologize over and over pleading for me not to sue or report him and how he would do anything to make it up to me for this misunderstanding. Well as the pleasing warmth from my bottom continued to spread I could see no harm in what just took place but took the opportunity to get to know Mr. Windsor a little better. I wiped the tears from my eyes and replied that if he took me out to dinner then all would be forgiven. He looked stunned and relieved at the same time,” really” he responded, “I would be happy to take you to the finest restaurant”. I want to find out more about this handsome man and hopefully taste more of his cane so we make plans for Saturday evening. He says he will pick me up, he also states that we will drop by an exclusive Dress shop so I can pick out a suitable dress for our date.
I am nervous as a cat all day Saturday wondering what is in store for me and the reminder of the still sensitive welts on my bottom make me masturbate constantly. I dress sensibly in a cute summer dress that I know Mr. Windsor will like. I see him pull up in his Jaguar so I hurry out to meet him and give him a big hug, he tells me how lovely I look as he helps me into the car. Stepping into the low riding sports car causes my legs to part and my dress to ride up giving him a good look between my legs. This makes his cock stiffen again as he drinks in the vision of the insides of my smooth silky thighs and sheer skimpy panties. I am oblivious to the mental torture that my actions and looks are imposing on this man. As we drive to the Dress shop that he mentioned we partake in small nervous conversation about nothing at all, mostly just to break the tension plus he asks me to just call him Harold and Not Mr. Windsor.
The Dress shop is a cute upscale store and as soon as we enter two lovely older ladies take me away as Harold makes arrangements for payment and states that price is not an issue. The older ladies are so nice to me asking what I need and for what kind of event. I tell them about our evening and the restaurant plus I confide in them that I am planning to spend the night with him so I need something very classy and a little sexy. They pick out this beautiful long gown that is a little see through and will give him a hint as to my figure underneath and coupled with some lovely high heels I look much older than I am. When I exit the dressing room so Harold can see me his jaw drops in amazement and thanks the Ladies for the transformation. I am stunned when I accidentally see the bill which is three thousand pounds. I do not let on that I saw the bill but I give him another big hug and a kiss on the cheek saying thank you.
Entering the Restaurant, all eyes are on me and Harold is very aware of it. The observant waiter sits us out on the patio where we can have some privacy and avoid the stares of the other patrons. The evening slips by quickly as we chat about my and his work plus world events and the usual small talk. That changes when he asks again if everything is Ok between us considering the severe spanking he gave me. I reply that I am glad it happened because it has given me a chance to get to know him. Besides I add, I really didn’t mind getting the cane from you. Harold smiles and tells me that he had considered adding another six strokes because I was not wearing regulation panties. I sit there contemplating my next move then I say, so that means that I am still due six strokes, will I be getting them latter this evening? Harold has to take a minute for what I said to sink in and replies; yes I think latter this evening would be perfect to give you the remainder. I ask him if there are any other indiscretions on my behalf that he could deal with at the same time, like tardiness and bad language maybe some homework not done on time. Harold sees where this little game of mine is going and simply says that he will deal with me when he gets me home but rest assured it will be substantially more than six. He adds that I should think about my naughty behaviour and confess to him when we get home so the proper punishment can be dealt out. He smiles when he sees me blushing as we both know full well where this evening is headed. Walking out of the restaurant, Harold offers me his arm. I cuddle up close to him as we wait for the valet to deliver his Jag. I shiver a little and Harold asks if I am cold, I smile sweetly up at him and reply no just nervous. Hmmmm he says, yes that is understandable but just remember you are safe with me and I will not do anything to you that you are uncomfortable with. That made me feel very warm inside and I pulled myself in close to him.
Harold’s house is a nice country cottage just outside London, lovely gardens and a nice quiet secluded setting. We enter this cozy house and he directs me into a spare room where he has some suitable school girl uniforms that he says will no doubt enhance the evening. The uniforms are similar to the ones at the Girls School but the Tartan skirts are so short they don’t quite cover my bottom. After I am suitably attired I meet him out in the living room where he has set up a tall whipping bench with straps to secure a young lady so she can’t move. He looks me over then smiles at my appearance asking why I have been sent to see him. This is my clue that the adventure had begun so I put on a little attitude saying that my Math teacher didn’t like the length of my skirt so I told him off. Harold reminds me to address him as Sir and then says that he has had many complaints about my behaviour and work ethics. He goes on to say that most girls under his domain get six strokes of the cane with their panties on but since there are so many reports on me it is only just that he should give me twenty four strokes of the cane on my bare bottom. I pretend to be infuriated and complain that his ruling is unfair and the other teachers just have it in for me. Mr. Windsor notices that in the punishment book I actually already have six strokes due to me so informs me that the count will now be thirty strokes on the bare and while restrained. I take a deep breath and change my attitude rather quickly, sorry Sir I apologize Sir please not any more than thirty Sir.
Harold realizes that the limit had been reached and agrees that thirty strokes of the cane on the bare bottom while restrained will be sufficient. Placing a hand in the small of my back, He directs me over to the front of the whipping apparatus and gently bends me forward until my feet are off the floor and my full weight is supported by it. My short skirt easily rides up over my bottom exposing me completely to his gaze and also the fact that my thin panties are completely soaked with my juices. Before he ties me down he removes my soaked panties and without me seeing him he brings them up to his nose to get a good whiff of my fragrant young pussy. The scent triggers his prehistoric urges and makes his already rigid cock stiffen even more. Harold sets about the task of restraining me by fastening my wrists to the far side, placing a large belt tightly over my back but when he fastens my ankles he spreads my legs far apart. It takes all Harold’s will power to not defile me on the spot, he thinks to himself that there will be plenty of time latter to satisfy his urges.
Harold stands beside me gently running his hand over my bare bottom and up and down the backs of my thighs. He runs his hand up the inside of my thigh and as he draws a finger over my clit and dripping pussy I let out a long low moan. Harold whispers into my ear that it is time for me to learn what real punishment is like. With my bottom still tender from yesterday’s caning I yelp on the very first stroke, the second one makes me squeal out in pain and the third has me bursting into tears. Well Harold says that did not take long for you to cry but you are going to cry a lot more as he whips me harder. After about a dozen strokes I am panting and sweating but the fire in my bottom and thighs is working its way to my pussy. Harold can see the juices dripping from my swollen aroused pussy so he pauses for a minute to stroke my clit and finger me. I try to hump his finger and cum but he stops just short of me having an orgasm. He goes back to whipping my bottom and thighs until I am crying out in pain and lust and before he reaches thirty strokes I cum and squirt onto the floor. I lay passively over the whipping bench as he applies the last six strokes not really knowing how much longer he will whip me. When he is finished I assumed he would untie me but instead he stepped up behind with his large stiff cock nudging between my pussy lips, then with one long thrust he buries his cock deep inside my dripping slippery pussy. He takes long methodical strokes as his massive cock fills and stretches my insides, with each thrust making me grunt. Harold’s orgasm comes quickly as he has been putting off ejaculating for a few days, his balls are full and his built up cum shoots deep into my pussy. I am in desperate need to orgasm as Harold pulls his still pulsating and dripping cock out of my ravished young virgin pussy. What I don’t yet know is this is just one step on how he plans on building my arousal to such a fevered state that I will do anything and everything for him.
He unties me from the whipping apparatus and my legs are so weak that he carries me into the bathroom where he starts a nice warm shower so we can clean up. He holds me close while we shower and gently massages my body under the running water. Again I feel his cock stiffen as it lies up against my sore swollen bottom and with one hand he teases my breasts and with the other he teases my clit. I just start to feel a massive orgasm come over me and he stops fingering me, I swear I was going to lose my mind. He turns off the shower and we dry ourselves off then he takes me into the bedroom where he gives me a cute little nightie to wear. He then leads me into the living room where he lights a fire in the fireplace and we settle down in a big comfortable chair to watch and warm ourselves in front of it. As we sit down and I cuddled up under his strong arm I move up to give him a big kiss. I kiss him like I am going to devour him, sucking the breath out of him and running my tongue all over the inside of his mouth. He pulls me away after a few minutes of necking and tells me that he has a lot more in store for me. I am nodding and saying yes please, not really knowing what but just wanting him so bad.
He has me stand up in front of the fireplace and he goes over to a cupboard to retrieve a thick leather strap. Right away I plead that I would not be able to take anymore punishment on my bottom. Harold smiles and says it is not for my bottom then tells me to get on my knees and hold out my hands, palms up. I do as he says without even thinking about and as he takes off his robe I see this fit naked man with a renewed massive erection. Harold asks me if I have ever taken a man’s cock into my mouth. No of course not I reply and before tonight I have never actually had a man touch me in any way. Harold looked surprised and questioned my virginity which I confirmed that tonight was my first time. Harold apologized for taking me the way he did not realizing that I was still a virgin, I was quick to reassure him that no apology was necessary. He hummed to himself and then said Ok we will continue as planned. He told me told me that he was going to give me the strap on my hands; six hard strokes on each hand until I am crying again and then he would have me suck his cock while I was still crying. I was so aroused and wanted him so bad that I would agree to anything he said, so I just nodded yes. I knelt and held out my hands, he was quick to smack one and I pulled it away, he barked at me not to pull away or move them in anyway or I would get double. I knew he meant business when he says double so I replied, yes Sir sorry Sir and presented my hands again. This is a pain I was not prepared for, the sting and pain of the strap striking my palms had me crying and howling loudly. I resolved that I would hold my position and I did, but after six strokes on each hand I was a quivering tearful mess. Just like he said he held my head asking me to open my mouth so he could slide his cock in. He pushed it right to the back of my throat which made me immediately gag; sorry he whispered that is something that you will need to learn, but not tonight. He pulled it back until just the head was in my mouth but even that was all I could take. He stroked his cock and told me to run my tongue around the head and said that when he orgasms he wants me to swallow all his cum. I find the texture of his cock head to be so pleasing and the little bit of cum that is leaking out is actually quite pleasant. Harold tells me that he is about to cum so I prepare to take it all. The gush of cum almost overwhelms me but I make every effort to swallow it all, it happens so fast that I don’t really get a chance to savour it. Harold slumps back into the chair and while I watch him recover from the strain he instructs me to lay on my back with my legs spread and masturbate for him. Now this is something I know how to do, so laying back I begin to tease and finger my clit. It is so erotic to have a man watch me masturbate that my first orgasm comes quickly and thankfully too. I am approaching my second orgasm which is building to a much more powerful one when Harold slips down between my thighs and starts to lick my pussy. The sensation of his tongue on my clit and lips is so powerful that I blurt out, “oh my gawd”. This actually brings a little chuckle from Harold as he sets to extract as many orgasms from me as possible. I lost count of how many times I came but when I was exhausted and spent and Harold’s face was soaked in my juices he moved up to kiss me and let me taste my cum on his face. At this point in the evening we retired to bed and both doze off in each other’s arms.
Sunday morning I awake to the feeling of a big erect cock pushing against my still sore and swollen bottom. I roll over to face him and kiss him deeply; He has a strap lying on the bed so smiling at him I roll onto my tummy. No Harold says, this is not for your bottom as he turns me over onto my back and spreads my legs wide apart. He takes the strap and begins whipping the insides of my thighs. This is another kind of intense pain but this time it only serves to inflame and arouse my passion. I look into Harold’s eyes as he whips me, he is smiling at me as my eyes water with lust and my breathing quickens. He paints the insides of my thighs a deep crimson before centering the strap right onto my pussy. Each smack makes me jerk and moan, smack after smack makes my juices flow and brings me close to orgasm. Harold times it so that just as I am about to cum he kneels between my thighs and plunges his engorged cock deep into me. I wrap my legs around him and hold on tight as I cum from his writhing monster serpent that is pumping and squirming deep in my belly. For the rest of the day I have Harold’s cock either in my mouth or in my pussy, he tried to put it up my bum but his big cock just didn’t fit. All day I practiced trying to take his cock down my throat and with a little help from a numbing throat spray we succeeded. As night began to fall Harold told me that he would take me to work in the morning and if I wanted he would pick me up at the end of the workday to bring me back here again. I was ecstatic and gave him a big hug and kiss saying absolutely, nothing would give me more pleasure, so we went to bed with his cock buried in me for the rest of the night.
In the morning I dressed in the summer dress that I was wearing when he first picked me up and we headed off to work. Mr. Atwater just happened to be looking out into the parking lot when we pulled up and we got out. He was pleased when he saw me give Harold a big long kiss before he got back in his car and headed out. Mr. Atwater called me into his office when he saw me at my desk and noticed I was walking a little stiffly. He had a big smile on his face as I sat down in front of his desk and asked me how my weekend went, he then added that he knew Harold Windsor very well and also had a pretty good idea what happened to me. I Smiled at him and asked if he had set it up, he replied that he only created the opportunity and the rest was all us. Well I confessed to Mr. Atwater that things could not have turned out better and my need and fascination for spanking was being well taken care of. Good girl Jennifer he said, and sent me back to my desk.
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