When I was sixteen, I was sent to a private boarding school to study for my A-levels.
The school was run by two sisters, both in their late thirties. Miss Isobel was the headmistress, and Miss Arabella, the deputy headmistress. There weren’t many boys, perhaps about twelve, so all the lessons were conducted by the two sisters.
Being aged sixteen to eighteen, and with a restricted syllabus, it was easy for just two teachers to run the school. Discipline was very strict and every boy would find themselves on punishment parade several times a term. Every misdemeanour earned a black mark against your name. And once you had six marks, they were deemed to have to be turned into ‘red marks on the bottom’.
The punishment was always the cane, six of the best! And the venue was the special room next to the headmistress’s office. Miss Arabella would haul you over the large desk and hold onto your wrists whilst Miss Isobel laid on six strokes of the cane across your trousered bottom. To be honest, it wasn’t too bad, as six of the cane across the seat of your trousers was a bit painful but not intolerable. It was probably the humiliation you felt and the obvious delight of the sisters in the act of punishment that made it a punishment more so than the actual pain.
Of course in your mid-teens, the hormones are starting to kick in, so I often had a bit of a wank after a caning. Not sure why, but an hour after the cane, I just felt very excited. Then, of course, the mind starts to fantasise about what might happen, or maybe happen! After all, the sisters were very attractive to an adolescent boy!
These fantasies were fuelled by the rumours of certain boys before us who had been given extreme punishments; on the bare bum, twenty-four strokes, the headmistress in stockings and suspenders. It was fun thinking about it at the time, but nothing ever happened like that to me (sigh!).
So, twenty years on and I found myself on a trip to that part of the country for a job interview. With the memories of those strange days in my head, I thought it might be interesting to go and visit the school once more. The old fantasies came flooding back but with an extra injection of eroticism. But alas, the school was no more. It had closed down ten years ago according to the internet. But the two sisters were still there, having turned the school into a small hotel.
I rang the number and was pleased to find they had a vacancy for the night in question. So, with a racing heart, I found myself ringing the bell at the hotel entrance. The lady who came to the door was Miss Arabella, still attractive as ever in her fifties, possibly even more so. I always think a mature lady takes on an air of grace and beauty and is much more appealing than some young bimbo.
"Hello Rob, so nice to see you again," she said. She had recognized the name when I had booked and now my face. How wonderful!
"I see the school has closed down, Miss Arabella, what happened?" I asked. It seemed right to still call her Miss Arabella and I could see she was pleased that I did.
"Come on inside, and let’s get you booked in and then I’ll tell you all about it over a drink. I hope you haven’t been a naughty boy like you were in school," and she gave a little laugh.
So an hour later, I found myself in the small lounge, a glass of wine each and she began to tell me what had happened.
"Well Rob, as you know we ran the school, and yes, Miss Isobel is here as well. Just gone shopping but will be back later, and I think she will be very pleased and excited to see you again. We knew we had to deal with you naughty boys and the cane seemed a very effective method. I think when you left we were giving six of the best, but unfortunately, Miss Isobel and I found that we were enjoying punishing you older boys more and more. We made the boys wear just their gym strip, vest, and shorts, and no underpants and the old six of the best became twelve. But then the boys became too difficult to hold in place for so many painful strokes. We then had a spanking bench made to order. A fine sturdy piece of work festooned with leather straps."
This was incredible, my mind was conjuring up all kinds of images.
"Of course, now the victim was strapped down, we could do whatever we liked. Some boys were getting eighteen and even twenty-four strokes. How they howled and screamed, and I am afraid we loved it, so exciting! Then on one occasion, Miss Isobel had finished giving twelve strokes, and this boy shouted at the end that we were a couple of fucking bitches and we should be locked up. Miss Isobel was livid! She pulled down the boy’s shorts and started flaying him with the cane. One stroke after another! He screamed out, Harder! HARDER! Imagine our surprise when we saw his cock spurt. After this, we had that boy on our bench many times. Miss Isobel even experienced orgasms from the infliction of pain, and we all really enjoyed ourselves."