In 1941, I was almost 12 and 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 mum’s friends I’d met before. Willow lived in London – or rather had. My mum 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 mum 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 Mum and I tried everything. In the end, Mum 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 Mum 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, Mum was rushing about getting ready. Willow hadn’t yet put in an appearance, and Mum 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 Mum 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 mum 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 bare 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 Mum 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, Mum 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 Mum 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 Mum 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 Mum said to Miss Matthews was to asked whether she had spanked many children. Of course, corporal punishment was almost universally accepted in those days, and Miss Matthews acknowledged with a smile that her daughters were no strangers to sore bottom, although she didn’t use a hairbrush or other object, finding spanking with anything other than a hand too cruel. But she had never spanked a boy before.
Hearing this, Mum told Miss Matthews in front of me that she and Willow had to leave for London immediately, but that I needed a very sound spanking and asked Miss Matthews to give me one, and to my dismay my host agreed with a broad smile.
Mum 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. Fortunately, her daughters had all gone to school. She lost no time in getting down to business, as it were, She sat down on the settee and in a brisk but polite voice told me: “Right, then – shorts and shoes off, please.” I did as I was told and suddenly felt very vulnerable standing in front of her in just my shirt, socks and underpants.
Miss Matthews glanced briefly at my pants and bare legs, 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, from her right because she was right-handed. I put myself there as best as I could, and she moved me so my bottom was directly over her right thigh. Although I knew I was going to be walloped, I was at least comfortable in that position.
Miss Matthews then asked me if I deserved what was coming, and I couldn’t say anything but a very quiet ‘yes’. Then she roughly pulled my pants down.
Unfortunately the comfortable position my penis was in was disturbed by my pants being yanked past it, and my willy was now in a very uncomfortable position. I hadn’t been circumcised, and in the position against Miss Matthews’ lap my foreskin was yanked right back, painfully stretching its connection to the rest of my anatomy.
“Ready?” Miss Matthews asked. I managed to say I was. Then she raised her hand and began spanking me, hard, making my bottom hotter and sorer with each smack. Worse still, my penis was getting squashed even more painfully as the smacking proceeded. It wasn’t a very long spanking, though – I guess that because as far as she knew at that time I had only kissed Willow.
Finally, Miss Matthews gave me a very solid ‘one for luck’ smack, telling me first that the harder it was, the more luck I’d have. Then I heard her saying I could now get up, but all I could do was to move myself backwards toward the right side of the settee, thankfully relieving the ache in my pinched penis, and try to cuddle her.
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 there was something else I knew I must do – to tell her about lifting the bedclothes to look at Willow’s bare 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 was disappointed. This revelation made Miss Matthews far more irate than she had been when I told her about kissing Willow. She told me what I did was disgusting, horrid, disgraceful and all sorts of other things. And she quashed my hope of no further spanking by telling me her hand was so practised from walloping her daughters she could still give me much more.
Then, at length, she ordered me back over her lap. I could only move slowly and painfully, and got in a position with my bottom a few inches to her right so my penis wouldn’t get squashed again. But Miss Matthews roughly moved me back into my earlier position and although she didn’t know it, the soreness in my front was worse than the ache from my bottom.
She began spanking me again, this time with more vigour. I wailed at the pain both back and the front, but it did no good. Every few spanks she punctuated each one with scolding.”Like looking at ladies’ bare BOTTOMS, do you? I’ll set YOUR bottom on FIRE. A lady’s BOTTOM is her own BUSINESS!”
It was horrible, and it went on and on until I thought I’d suffocate with all my crying and pleading with her to stop, only realising later that every time I begged her to stop spanking me the spanks got a bit harder.
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 to make the anticipation worse, then asked:”What makes a spank for luck really lucky?” Of course, I could only gasp out the words she had uttered after the first walloping she’d given me. “The harder it is, the luckier I’ll be.” “That’s correct!: she answered, raising her hand and driving it with all her force into my bare bottom.
Then she stood me back on my feet. I couldn’t do anything but jump round the room, screaming, holding my scorched bottom. My pants round my ankles hindered this a bit, but they were soon shaken off one leg entirely.
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 Mum and one of my babysitters had spanked me soundly, but not so nearly as hard as she just had.
I took her advice about rubbing my bottom, but subconsciously put one of my hands near my throbbing penis. This drew Miss Matthews’ attention to it, and her eyes widened in wonder when she saw how red the end was. She didn’t seem worried about what she might have accidentally done,.
“Good gracious!” she said. “That willy looks sorer than your bottom! How did that happen?” I tearfully enlightened her how it had been squashed against her thigh, expecting her to be a bit sorry and say she didn’t mean for that to happen.
But her reaction was the opposite. Her smirk turned into a slight laugh she didn’t bother to try to hide, and she told me: ‘Well that’s an even better lesson not to look at ladies’ bottoms!” She beckoned me to come closer and had a good look at my penis concluding out loud with a real laugh: “Yes, that will ache for days, just as your bottom will – bad luck, you naughty boy!”
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 but with my penis a bit further from her than before.
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, retrieved my pants from one ankle and pulled them back up again briskly. “Now get your trousers back on, there’s a good boy – the girls will be home for their lunch any minute.”
On their arrival, I did think that Miss Matthews’ eldest –º who was 18 – 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.
Mum 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, getting a proper look at all my private parts. “Sorry!” she tittered, “I thought my sister was in here.” Yeah, right.
Of course, I couldn’t help feeling that Mum 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 children before.
I didn’t realise until the apology Mum subsequently forced me to make that our guest knew precisely how to use a hairbrush – and a cane. Soon after that, Miss Matthews and her eldest daughter came for tea. Afterwards, I was sent upstairs afterwards to read, but I heard uproarious laughter coming from downstairs.
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.
To my chagrin, this included the tale of a teasing, laughing walloping and rough-handed inspection of both bits the eldest daughter had given me the day after her mum had, when everyone else was out.
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 both my bottom and penis is something I will never forget.
Contributor: Tim