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Retired Headmistress and Headmaster


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Making contact with a retired Headmistress leads to pain and humiliation.

The advert was simple.

Retired Deputy Headmistress seeks naughty 'boys' for punishment. The Headmaster may be called upon for those in need of severe treatment.

A brief exchange of emails and a date was arranged. It was a good hour’s drive, and on arrival, I was bemused to find that it was indeed the old school house where the headmaster would have lived when the school had been open.

An attractive lady in her late sixties, I guess, answered the door. This turned out to be Miss Dean, the headmistress in the advert. And yes, she was definitely retirement age!

“Hello, you must be Rob? Please come in and go through to the lounge.”

I entered and walked into a comfortable lounge with an open fire. Very cosy, I thought.

“So from your emails I see you have been a bit of a naughty boy lately, and you need to be disciplined. Is that correct?”

“Yes, I think so, Headmistress. I mean, yes, I do, but I am bit nervous, Headmistress.”

She smiled.

“There’s nothing to worry about, yet! But please tell me the kind of things you like and why you answered my advert, and you can address me as ‘Miss’”.

“Well, Miss, I have never been properly punished, properly thrashed, and I guess you, being a headmistress, I thought this might be the place to come. I’m not sure about the headmaster, although I like the idea of the humiliation of being punished by a couple.”

“So you want a good thrashing - excellent! And humiliation. Oh! We can do humiliation, Rob,” she laughed. “ You say a real thrashing, Rob? What do you consider to be a thrashing?  Six of the best perhaps? Or what?”

My thoughts raced through my head. Was I going to be honest or was fantasy going to take over?

“Well, Miss, I know that six of the best was considered to be a punishment, but over the years I have read many accounts of canings and punishments. I have to admit at being intrigued by an account of a caning of a sixteen-year-old girl at a reformatory.”

I wondered if I should say more. This was going into a dark place.

“Go on Rob, tell me more. I can see this is going to be exciting for all of us if I think you are going down that road.”

I stuttered a little, and my head was going a little dizzy. I knew the words I wanted to say, but fear and excitement were mingling fast.

“Well Miss, she was naked, and strapped down on a caning bench…..”

“We have an excellent caning bench, Rob. I can assure you that you will not escape your deserved thrashing!”

I continued, blushing a little as I prepared my words.

“She was caned with a heavy dragon cane, in sets of six strokes. She was made to scream and beg for mercy. I believe she was sentenced to twenty-four strokes, four sets of six.”

I paused. Did I really know what I was saying? Is this really what I wanted?

“Oh Rob, that sounds quite exciting. Is this what you want? Do you want to scream and beg for mercy? Get my heavy dragon cane scorching across your big bare bottom?” She laughed again.

 “Yes Miss, I think so. I have wanked off so many times thinking about what it must have been like. And that’s why I am here and hope you can help me.”

She paused and took a deep breath as she was obviously thinking about my desires.

“Well, Rob, what you ask for is certainly possible. What we agree in here will be carried out, and there will be no escape until we are finished with you. You also asked for humiliation and we will certainly humiliate you. You desire punishment but we also want to get something out of our time with you, a sort of mutual fun agreement. If you agree to that then there will be no fee.”

A mutual fun agreement? What could that mean, but no fee was the deal clincher.

“Yes. OK! What do we do now?”

“Ok Rob, you need to sign a piece of paper agreeing to your punishment and subsequent activities. Your punishment today will be a minimum of twenty-four strokes of the cane. These will be laid on with full force from the very beginning.  Twenty-four is the minimum number, as you may earn more strokes if we deem necessary. They will be delivered in sets of six. As you agree to no fees, then you will be required to perform oral duties. Do you agree to all of this?”

Oral duties! So that’s their fun. My cock stiffened quickly. Perform oral duties on this lady? Why not? I thought. Why not just jump in at the deep end!

“Yes, Miss Dean I accept your punishment and will sign the paper”.

Miss Dean went to the desk and brought out a piece of A4 paper. Obviously prepared in advance. She wrote ‘24’ in the number of strokes box and handed it to me to sign.

I read it quickly and my cock hardened even more. It was absolving them of any comeback or blame for what was about to happen. The words ‘severe’ and ‘no mercy’ caught my eye.  Heart racing, I signed on the dotted line!

“Now that is out of the way we can get started! I want you naked. That’s right! Strip off! Everything!”

I stood up and slowly undressed. My undies came off and she could see my cock was semi-erect.

“What’s the meaning of that?” she said disgustedly. “I can see we are going to have to really thrash you today, young man.” And my cock hardened even more.

“Mmmm! So your cock responds to my threats? So if I tell you I am going to give you twenty-four strokes of the heavy cane? Oh yes, your cock seems to be growing, and what if I said one hundred strokes? You naughty ‘boys’ are such funny creatures!”

She bundled my clothes together and locked them in a cupboard.

“There is no escape for you now. You will only get your clothes back when I have finished with you, so time to go and see the headmaster.”

A feeling of helplessness came over me. A point of no return, committed! Down the hall we went, and into a second lounge. The headmaster was there, smartly dressed in a suit, flexing a formidable looking cane. Next to him was their spanking horse, a padded trestle with kneeling shelves either side.

“Get up on the horse, young man,” he barked.

I clambered up, my legs astride, and I realised my cock and balls were well exposed to their eyes. More humiliating was that my semi-erect cock had to be pushed into a downward position so they knew fine well that I was sexually excited. Straps were fastened around my knees, and my wrists placed in cuffs. These were then pulled forward and fastened to short chains. I had quite a degree of movement for my upper body and arms, but my bottom was definitely well presented and would not escape any punishment.

Miss Dean could see me moving around and explained.

“I like to see my naughty ‘boys’ writhe and squirm, to see them trying to protect their fat bottoms. It’s much more fun than having you tied down unable to move an inch. So, Headmaster, it’s time to start the fun. The cane, one stroke every ten seconds, I think.”

The cane landed with a familiar ‘Splattt’ and the explosion of pain went through my body. The headmistress then drew up a chair right in front of me and removed her skirt. She was wearing stockings and suspenders, and no panties. She sat on the chair, legs wide apart so I could see her pussy, and she started to play with herself.

“I like to watch your face as it tries to cope with the pain and to hear your pathetic attempts to take your punishment without being a wimp. But I know that you will soon be shouting and begging me to get the cane to stop and that just makes me even wetter.”

With that, she took a deep breath and plunged two fingers deep inside her now wet pussy.

The cane cracked across my defenceless buttocks for six agonizing times, and yes, I writhed, and I squirmed, and I shouted, and begged, much to her absolute delight. The pain was more than I could bear. What had I done?

A short delay, and then the second set of six were duly delivered, one stroke every ten seconds. The overall pain was beginning to overwhelm my senses. This wasn’t fun!  I started to beg for them to ease off, to give me a chance to recover.

The third set of six strokes were duly delivered. I was screaming, and there in front of me was Miss Dean masturbating. I could smell her juices.  Again a short break before the final set of six. At least I knew what was coming. I knew the intensity of pain I had to endure. Finally, the twenty-fourth stroke hit home, just as hard as the first stroke.  I flopped down on the bench, breathing heavily. My bottom was on fire. Thank goodness it was over.

Then, horror! Miss Dean moved the chair right up to my face, and came and positioned her pussy right on my mouth, her legs wide and draped across my back.

“Time to eat pussy, naughty boy!”

I had no choice as any reluctance was dealt with by the cane, with rapid salvos of strokes carried out at her command. She tasted as a woman does but in her sixties? Yuk! After what seemed an eternity, she eased herself away from me. Maybe I had done what she wanted. Did she really have an orgasm? Then the headmaster stopped caning, and I thought it was over, but no!

“I think it’s my turn for some fun now, Headmistress!” said the Headmaster.

And with that, he came to my face and took out his large cock. It was now her turn to cane, as I was forced to suck his cock. It was disgusting! I have never done anything like that ever, and what reluctance I showed was soon caned out of me. I realised what I had to do because he made it quite clear,

“Suck me off, boy!” he barked.

I also reasoned the sooner I did it then my ordeal would be over. So sucked and licked I did, till my jaw muscles ached. Then came my reward, a mouthful of warm salty spunk, which I was told to swallow in no uncertain terms. The deed over, I realised that I had gotten what I asked for, a thrashing and humiliation, and what humiliation it was too!

And so it was, my visit to the headmaster and headmistress. Thrashed and humiliated.

And yes, I did go back, again and again!

 

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