Most of this story revolves around a submissive voyeur imagining himself at a mixed finishing school, where all the students are over 18. No one under age, real or imagined, plays any part in this tale of role play whatsoever. If a man being willingly dominated by a woman is not your thing you might be better to finish here.
Now, you may remember from the last episode of my story that I have only ever named one client. Why should George from Bolton be accorded this singular accolade?
Well, most men simply want a rub and tug. Some men like it slow while gently fondling my breasts, some fast and furious as they clasp my buttocks firmly. Some like to talk dirty, some like to remain silent with their eyes closed. Some cum very quickly, and some take a lot more effort, but the objective is always the same, a nice big satisfying ejaculation, the more cum and the further it squirts, the better I feel I've pleased my client.
But George, dear George from Bolton, wanted me to keep stimulating him long after he'd cum. In fact he didn't want me to stop rubbing his highly sensitised cock, no matter how obvious his discomfort, until he'd said his safe word. He had withstood it for ages, and was obviously in considerable pain before he did. He was finding the pain erotic!
The more I thought about it afterwards, the more I realised how much I had enjoyed inflicting the discomfort on him. The way his face contorted, the little yelps for mercy, the thrashing about on the table, all added to my enjoyment and, much as I didn't want to admit it to myself, the dampness between my legs betrayed me.
Even though I'd tried to forget, my pleasure centres reminded me that he'd given me his card, with the parting words that there were men willing to pay handsomely for my services.
Would I dare ring him? What would he ask me to do? Obviously, I had progressed this far, so why not capitalise on the situation and take it to the next level?
The phone was answered on the third ring.
"George here."
"Hi George." I said. "You gave me your card last week after your 'therapy' session."
"Ah yes, I remember it well. Very well. Glad you called. Maybe we could arrange to meet and discuss future possibilities?"
Eventually we decided on a mutually convenient wine bar, with individual alcoves and plush seating. George was already seated when I walked in. He stood up, ushered me in to the alcove and offered me a drink.
As I sipped my gin and tonic, George opened up the conversation.
"You are very good at your job, and you gave me exactly what I wanted. I think I could tell from your facial expression that you quite enjoy your work, and you enjoyed giving me my 'therapy' as you so cleverly put it.
"I mentioned some friends who would be interested in your skills. How do you feel about spanking?"
"Giving or receiving?" I asked, wanting to know exactly what he had in mind.
"Ha! Good question! No, I mean giving. I have a very dear friend who likes to be spanked and, let's say, likes your sort of therapy afterwards. He is a wealthy man and willing to pay handsomely for a therapist with your sort of skills. Interested?"
Of course I was interested, but didn't like to ask what 'pay handsomely' actually meant. George, sensing my hesitation, mentioned a figure. I tried to keep my cool but it was a figure of many times what I normally made in a whole evening of rubbing and tugging. I nodded my agreement.
George passed me a small book in a paper bag and gave me a card bearing the name Stephen and his contact details.
"You will learn a lot from this little book, much of it very important if you are going to administer a good spanking, particularly with a cane," he said with a glint in his eye.
"Just call Stephen and say it's Cori. I have told him about you and he will know why you are calling." We chatted a while longer before he told me he had other contacts with 'individual tastes' and he could put me in touch, if I was interested, after meeting Stephen.
I read the book. I had no idea that there was so much to spanking, or that there were so many different implements, some purpose made, others just pressed into service. One suggestion was, when in a hotel room, a coat hanger will often suffice.
I had learned that spanking with paddles was reasonably straight forward, but wielding a cane was an art. I was not sure what I was going to be asked to use, but I took George's hint, so practice was called for.
I sent away for some canes! A thick one, I had learned was for a thuddy experience, and a thin one for a much more stingy sensation. Not being sure what Stephen was after, I bought both and because the thin one was more difficult to manage properly, that's what I decided to practice with.
They arrived and I unwrapped them in anticipation. The thin one was really quite awe inspiring, rattan with a curved handle and slight upward bend along its length. I paraded around my room swishing it menacingly, very satisfying. I was eager to practice and even more eager, though I didn't want to admit it to myself, to try it out on a nice yielding male bottom. The thought alone was quite exciting.
I propped up a cushion at the appropriate height, dusted it with talc, and set about practicing. It wasn't easy to avoid wrapping. Wrapping, I learned, is where the cane comes round the side and can be extremely painful or even dangerous, certainly not erotic.
It took a while until I was hitting the target with parallel strokes every time, the practice certainly helped and the talc left satisfying evidence of my progress.
I rang Stephen the following week and we arranged to meet at the same wine bar to discuss 'possibilities'. He wanted to play the part of a schoolboy, over 18 of course, who had been caught doing something pretty naughty and was about to be caned. One strange thing was that he was very old school, smartly dressed, very well spoken and about my father's age! The other thing was that he told me to play along with whatever occurred.
"You can ham it up as much as you like, but be prepared for a few surprises. I don't want to spoil the fun so that's all I'll say for now. I can just promise you that, apart from the caning, you won't be asked to do anything out of your comfort zone."
There was no exact script, it was to be all ad lib, but I was to be the headmistress of a mixed crammer. For those unaware, a crammer was a boarding school, whose sole purpose was to get students, who had failed their university entrance exams at the age of 18, a pass at the second attempt. So the students were by definition all 19.
He was most insistent on this point because even though the whole scenario was to be imaginary, he didn't want to compromise me with anything that could even be considered illegal. Kinky yes, perverted no!
How was I going to dominate such a man? But that's what he wanted and that's what he was paying for. I was trying hard to imagine his bum as a target rather than just a velour cushion.
He told me that he had to be punished, with a cane, and was to count the strokes. If he failed to count one it was to be repeated, if he counted two that meant the last one was too hard. He had obviously thought this through in great detail.
The finale (assisted with a bottle of lotion, ostensibly to reduce the flesh injury) was to be with us both naked, and him to be be 'satisfied' while standing: how we got there was up to me, but the talk had to be dirty: the filthier the better.
The fee offered was sufficient to make sure he got what he wanted. Oh and a safe word? Yes! Banana! What is this with bananas? Some sort of kink club?
He described the room that was to be 'My study,' in detail, and passed me an envelope containing pictures of it, so that I would be able to locate everything easily and told me I'd be shown round anyway.
A few days later, I called at his house, dressed in my best headmistress outfit. White blouse, no bra (they so get in the way in my line of work) and black pencil skirt. The door was answered by a short, middle aged woman with close cropped grey hair, wearing a loose summer dress. She looked rather severe, probably more like a headmistress than I did. This, I was not expecting! Was she his wife? Was this one of the surprises? Now this was getting kinky!
"Headmistress, I am the new deputy head," she said, "my name is Miss Taylor."
Headmistress? So she was definitely in on the whole thing! Why? What's going on? Does she not like giving a spanking? Does being spanked by his wife not get him off? Oh my god! Does she want to watch? Does she want to take part even? This was getting weird: really weird.
I am quite used to giving a man an oily wank, or an oily wank while naked. I even quite enjoy giving them an oily wank while naked, as they fondle my boobs, if that's what gets them off, but I've never had an audience before: hmm, not so sure.
She showed me to the room and gave me the tour, emphasising the desk, a twelve inch wooden ruler, a bottle of lotion and a large ominous looking, black leather paddle. Oh I was going to enjoy this.
She paid particular attention to the cane cupboard and is contents. Four labeled canes hung from a rack, all of different thicknesses. On the left hung the thickest bearing the legend Swearing, the next, Smoking, the last two, really thin ones, ominously, Most Serious Offences.
Everything was exactly as in the photographs, so I felt reasonably comfortable. As 'Miss Taylor' closed the door behind her she parted with.
"Headmistress, I shall send the miscreant along shortly."
A few moments later there was a knock at the door.
"Come!"
I commanded in my best headmistress' voice. Stephen entered looking suitably contrite.
"Well, come on boy. Get in here. Stand on the mat by the window....."
He stood on the mat, by the window, with his hands clasped behind his back and head slightly bowed.
"So why do you think you are here, boy?" I demanded.
"I was caught 'out of bounds' Miss."
"I see, so exactly whereabouts, 'out of bounds' were you caught?"
"In the Pink Corridor Miss."
"Aha. You know very well that the whole of the Pink corridor is totally out of bounds to boys, just as the Blue corridor is out of bounds to girls. So whereabouts in the Pink Corridor were you?"
"Near the senior girls changing rooms Miss."
"Near the senior girls' changing rooms! You certainly must know that being there is breaking the strictest of school rules. Don't you?" And I picked up a twelve inch wooden ruler from the desk and started to slap it in the palm of my hand. I was really getting into this.
"Yes Miss."
"So why were you there, if you know it's out of bounds."
"Don't know Miss."
"Don't know! Don't know?" I said in a rising crescendo. "I think you do, and the sooner you tell me the truth the easier it will be for you. So what were you doing there?"
"Peeking Miss."
