In 1941, I was in a day school for boys in Oxford. I had no siblings, and my father had been killed in the war in late 1939. Lots of others who lived nearby had also lost their fathers, and many more men were away fighting. Everything in Oxford, though, was much more peaceful than elsewhere in England, owing to Hitler’s vow not to include the ‘dreaming spires’ in the Blitz.
My school had broken up for Christmas the day before this happened, although many remained open for a day or two longer, including a girls’ school nearby. I came back from school about four o’clock in the afternoon, overjoyed that the term was over for the year. But immediately I saw another lady in the house.
It was a young, single woman called Willow – one of my Mother’s friends I’d met before. Willow lived in London – or rather had. My Mother took me into another room and told me that Willow’s flat had been bombed in the Blitz. She ended up staying with us until the war’s end, which should have been nice but ultimately wasn’t.
Since my Mother was an ambulance driver, she had access to petrol and could drive when most lacked the fuel to get anywhere. That morning, she had gone to London to bring Willow back after being notified of the disaster.
They would have to return to London the next day to see about the few possessions that had been salvaged; looters had taken most of Willow’s possessions, of course, but the police had been able to gather up what they could. However, the police station was overflowing with things belonging to people who had been killed by the bombing and whose relatives hadn’t yet arrived to claim the deceased’s possessions, so the police wouldn’t guarantee that the things wouldn’t be ‘lost’ if not collected by 10am the next day.
Willow was unharmed but in naturally in something of a state, and nothing comforted her, although Mother and I tried everything. In the end, Mother gave her a bottle of sleeping pills, told her to take two, and put her to bed.
I hoped I was going to London with them, but that evening Mother informed me that she had made arrangements with a Miss Matthews down the road to look after me at her home for the day.
I had always found Miss Matthews very attractive. She had four daughters, three of them older than I was, who were day pupils at the local girls’ school. Miss Matthews and her husband had acrimoniously divorced the year before and she’d taken up her maiden name again.
She and I would be alone, at least until her daughters came back from their school for lunch – of which I was envious since the meals my school served weren’t fit for pigs. But the thought of spending so long in the sole company of Miss Matthews was marvellous – it was nearly as good as going to London.
In the morning, Mother was rushing about getting ready. Willow hadn’t yet put in an appearance, and Mother sent me upstairs to tell her to hurry. The door to our spare room was open just a hair, so I knocked but got no answer. That was odd. I knew Mother had put Willow in the spare room the night before. Had she sleep-walked somewhere else?
I pushed the door open a little bit more and saw that Willow was still asleep, lying on her side facing away from me. I went round the other side of the bed to gently wake her up, which is when I noticed that the bottle of sleeping pills was now half-empty. Our guest must have taken at least four or five of them during the night.
I looked at Willow, sleeping peacefully, and realised that she was nearly as attractive as Miss Matthews. I had yet to kiss a girl or lady other than my mother, and desperately wanted to do so. My Mother always woke me up by kissing me, so I had an excuse for doing so.
I knelt down by the bed and – very gently – kissed Willow’s cheek not very far from her mouth. She still didn’t wake up, so I kissed her, again very gently, on her lips. Still, she didn’t stir. The opportunity was too good not to jump at – I proceeded to kiss Willow passionately on her lips. It was lovely. This act made her move her head and torso, slowly and just a bit, but she still didn’t wake up.
Then I noticed that her movement had shifted the bedclothes slightly and that Willow’s shoulder and upper chest showed no sign of a nightie or pyjamas under the bedclothes.
The possibilities this brought to mind were breathtaking. I still had no interest in bosoms, but was certainly beginning to notice ladies’ bottoms. Did I dare look further? The chance to kiss Willow passionately had been too good not to be snapped up, but as happens to all whose sexual feelings are just coming to the fore, the new opportunity was overpowering. So I stole round the side of the bed closest to the door and, again very gently, lifted up the bedclothes.
And there it was. I’ll never forget the beautiful sight of Willow’s bottom. The concept of time no longer had any meaning. I must have gazed at it for a full minute, taking in its smoothness, its curves and wondering if I might very gently move one side of it to see the luscious flesh I knew was in between.
But then Mother made the question moot. She arrived upstairs to see if Willow was awake, and saw Willow’s bottom with me holding the bedclothes up, looking fondly at it.
Predictably, Mother was furious. She ordered me to go downstairs and wait. Then she managed to wake Willow up and get her into her clothes, and told her they would have to drive like mad to get to London by ten. I could hear Willow, now awake and depressed (and thankfully oblivious of all I had done), saying she couldn’t eat a thing.
Then Mother came back down and very crossly asked if I’d done anything else before she came in. I was so scared that I confessed I’d kissed our guest three times, one of them passionately on her lips.
This naturally made Mother even more angry, but she couldn’t do much at the time. She went back up, got Willow downstairs and bundled us both into the car. She drove us quickly to Miss Matthews’ house, marching me in there as Willow dozed back in the car.
The first thing Mother said to Miss Matthews was to ask whether she had spanked many children before. In those days, corporal punishment was almost universally accepted, and Miss Matthews acknowledged with a knowing smile that her daughters were no strangers to sore bottoms. She explained that she never used a hairbrush or any object, believing that spanking with anything other than a firm hand was too cruel. But she had never spanked a boy before, and there was a glint of curiosity in her eyes as she considered the task ahead.
Hearing this, Mother told Miss Matthews, right in front of me, that she and Willow had to leave for London immediately, but that I needed a very sound spanking for my misdeeds. She asked Miss Matthews to give me one, and to my dismay, my host agreed with a broad, almost eager smile, promising to deliver a lesson I would not soon forget.
Mother said: “Timothy will tell you what he did before you give him his spanking. And mind you, my lad (she looked at me now), I will check with Miss Mathews that you have told her the truth. We’ll be back later.”
Suddenly I was alone with Miss Matthews. Her daughters had all gone to school, leaving us in complete privacy.
Miss Matthews was a striking woman in her late thirties, with a tall, graceful figure and an air of quiet authority. Her hair was a rich chestnut brown, always neatly styled, and her eyes were a clear, intelligent blue that seemed to notice everything. She dressed with understated elegance, favouring crisp blouses and well-tailored skirts, and carried herself with a poise that commanded respect. Despite her stern manner, there was a warmth in her smile and a gentle patience in her voice, especially when speaking to children. Her presence was both comforting and formidable, making her a figure both admired and slightly feared by those in her care.
She wasted no time, sitting down on the settee and, in a brisk but polite voice, told me to prepare myself. My heart pounded as I obeyed, feeling exposed and vulnerable . The room seemed to grow colder as I stood before her, awaiting my fate.
Miss Matthews glanced briefly at me, then looked me in the face and said: “Tell me what you did, then?” I squirmed a bit and stammered out only that I’d kissed Willow while she slept.
Miss Matthews was cross, of course. She scolded me and snarled that doing so was very naughty, that doing anything to a woman who couldn’t tell me not to was dreadful, although adding– and this made my heart sink even lower – ‘at least that wasn’t the worst thing you could have done.’
She then ordered me over her lap, instructing me to approach from her right since she was right-handed. I awkwardly positioned myself across her knees, my bottom directly over her right thigh. The anticipation was excruciating, and I could feel her steadying me, making sure I was in the perfect position for what was to come. My heart thudded in my chest as I braced myself for the first smack.
Miss Matthews then asked if I deserved what was coming, and I could only whisper a very quiet ‘yes.’ I felt a flush of shame and fear, knowing there was no escape from the punishment that awaited me.
Miss Matthews explained, in her clear and proper voice, that what I had done was very wrong and must be punished. She placed me over her lap and, after making sure I understood why, she delivered six firm smacks to my bottom, each one stinging more than the last. I counted them out loud, as she instructed, and by the sixth smack, my eyes were full of tears. Miss Matthews told me that this was to teach me a lesson, and that she hoped I would always remember to behave properly in future.
Finally, Miss Matthews delivered a very solid ‘one for luck’ smack, warning me that the harder it was, the more luck I would have. The final blow was the hardest of all, making me gasp in pain. She told me I could get up, but I could only move slowly, my bottom aching fiercely as I tried to compose myself. I instinctively reached out to her for comfort, seeking solace after the ordeal.
Fortunately she cuddled back. It was a lovely moment, ameliorating my soreness on both sides. I asked her if I could kiss her – it seemed only right to get permission beforehand since she’d just spanked me for not asking Willow first. And with a nice warm smile, she gave me permission.
So I gave her left cheek a long, lingering kiss, then moved to kiss Miss Matthews’ mouth. She only put her lips on mine for a very quick peck but it was even more lovely than kissing Willow. We cuddled more, and I told her I’d always thought she was beautiful. She replied that she’d noticed me looking at her before and was flattered, but not surprised.
This should have put my mind at rest, but I knew I must confess to lifting the bedclothes to look at Willow’s bottom. I hoped desperately that the loving embrace we were in would lead her to say something like: ‘Well, I’ve just reddened your bottom and my hand is still sore, so consider yourself punished for both.’ But I feared another, even harsher punishment.
But I was disappointed. This revelation made Miss Matthews far more irate than before. She told me what I did was disgusting, horrid, and disgraceful, her voice rising with each word. She quashed my hope of no further spanking by telling me her hand was well-practised from walloping her daughters and she could still give me much more. Her stern expression left no doubt that another, even more severe spanking was imminent.
At length, she ordered me back over her lap. I moved slowly and painfully, my bottom still sore from the first spanking. I tried to position myself to the side, but Miss Matthews roughly moved me back into place, ensuring my bottom was once again perfectly presented for punishment. The ache in my front was now matched by the dread of what was to come.
After I confessed to my further mischief, Miss Matthews looked very stern indeed. She told me that another spanking was needed to help me learn right from wrong. Once again, I was placed over her lap, and this time she gave me eight sharp smacks, each one carefully counted. The pain was real, but I knew it was given with care, to help me become a better boy. When it was over, she reminded me that good children always tell the truth and respect others.
It was horrible, and it went on and on until I thought I would suffocate from all my crying and pleading with her to stop. But every time I begged her to stop spanking me, the spanks only got harder, her determination unwavering. My bottom felt as if it were aflame, and I could do nothing but sob and promise never to misbehave again.
Finally, she announced that it was time for another ‘one for luck.’ I was relieved that it was nearly over, but still couldn’t stop crying. Miss Matthews waited for a few moments, letting the anticipation build, then asked: ‘What makes a spank for luck really lucky?’ Through my tears, I gasped out the words she had uttered after the first walloping: ‘The harder it is, the luckier I’ll be.’ ‘That’s correct!’ she answered, raising her hand and delivering the hardest smack yet, making me yelp in pain.
Then she stood me back on my feet. I could do nothing but jump around the room, screaming and clutching my scorched bottom. My pants, still around my ankles, hindered my movements, but I was too sore to care. The pain was intense, and I could feel the heat radiating from my punished skin.
When I was finally sufficiently in possession of my senses, I looked into my spanker’s eyes and saw that she was not only satisfied with her performance but amused at how sore I was. With a smirk, she said: “Well, Timothy, your bottom might cool down a bit faster if you stopped rubbing it so hard!”
Then she looked me in the eye again: “Have you not had your bottom smacked before?” With a blush, I admitted that both Mother and one of my babysitters had spanked me soundly, but not so nearly as hard as she just had.
‘Well, that’s an even better lesson not to look at ladies’ bottoms!’ she declared, her tone both stern and amused. She beckoned me closer, concluding with a real laugh: ‘Yes, that will ache for days, just as your bottom will – bad luck, you naughty boy!’ The lesson was harsh, but I knew it was meant to teach me right from wrong.
I didn’t exactly answer her. I could only let out a gasp of passion and laid myself gingerly down on the settee, again on my side, cuddling her even more fiercely.
This time too she cuddled back, and I kissed her cheek again, this time more meaningfully. She didn’t mind that, but still wouldn’t let me give her more than a peck on her lips. Eventually she let go, “Now be a good boy – the girls will be home for their lunch any minute.”
On their arrival, I did think that Miss Matthews’ eldest noticed how gingerly I sat down at the table. The shocked and amused expression on her face indicated she had guessed what happened that morning – but she said nothing at the time.
Mother rang up later in the afternoon, saying that she and Willow had been delayed in London and asking Miss Matthews to keep me overnight.
I’m fairly sure Miss Matthews privately told her eldest daughter about my two horribly sore bits, because later that evening she ‘accidentally’ burst in on me while I was getting into the bath, . “Sorry!” she tittered, “I thought my sister was in here.” Yeah, right.
Of course, I couldn’t help feeling that Mother would eventually make me tell Willow exactly what I’d done and apologise to her. Willow was younger than Miss Matthews, so at the time I drew a tiny bit of comfort from the thought that she probably hadn’t smacked any before.
Later, when I had to apologise to Willow, she explained that my actions had been very naughty indeed. She told me that a proper lesson was needed, and so she gave me four quick smacks with a hairbrush, followed by two with a cane. Each one was counted, and I promised to remember my lesson and never repeat my mistake.
I’m sure the women were all exchanging accounts of how each one had punished me and the effects they’d had on each part of my anatomy.
The next day, Miss Matthews’ eldest daughter, with a mischievous smile, decided that I needed a reminder of my lesson. She gave me three quick smacks, each one making me wince, and told me that good manners were very important. I thanked her politely, even though I was sore, and promised to be on my best behaviour.
During this, she demanded to know which of the four girls I thought had the prettiest bottom. I told her she did, hoping she’d be complimented and not spank me so hard. But the revelation that I’d looked at her bottom to that extent just made her wallop me even harder – and the ‘one for luck’ she bestowed on my bottom was the hardest of all, leaving me sore and chastened for days.
