A Babysitter Gets Caned

A Babysitter Gets Caned

Yesterday I was tidying out the wardrobe in the spare room when I came across a long soft case with a punishment cane inside. My wife had only ever needed to use it on me on one occasion many years before and I suppose it had been there since. I have only experienced 2 bare bottom canings in life and am not keen to repeat the exercise.

The first is an experience which happened to me in 1970 when I was 19 years old. On the road where we lived there was a married couple who knew my parents quite well. He was a successful businessman, and she did not work. I did not have much contact with them when they came to our house, but I fancied the wife like crazy. Maybe this was because she looked like a more mature and real-life version of a comic actress who was popular at that time. Jane was in her mid-thirties and had a face and body that I would have willingly died for. On occasion I used to watch her walk to the shops past our house and I can still remember the effect that her mini skirt and boots and her thighs used to have on me. She was of course completely out of my league, and had a cold unapproachable air about her, and I do not think I had ever seen her smile. She was my favourite teenage fantasy and I used to lie in my bed and masturbate whilst thinking about her.

I went to University and at the end of the first term I returned home for the Christmas holidays. After a few days of mooching around I was getting bored, when one afternoon Jane rang up my Mum and asked her if I would be able to baby sit her 7-year-old daughter that evening. Her normal babysitter was ill. Jane was going out alone to a Christmas party, her husband being abroad on a business trip.

I turned up at about 8 o'clock, by which time her daughter was asleep in bed, and Jane told me she should not wake and I should have no problems, gave me a telephone number where she could be reached, showed me where the tea, coffee, and biscuits were to be found, switched on the television, and telling me as she left she would be back after midnight.

I watched a little television, but viewing choices were limited in those days and within a couple of hours I was bored. I remember there was a photograph of Jane on the sideboard. I cannot remember it being particularly revealing, but as I studied it I developed an erection and started to stroke myself. At first I touched myself under my underpants and trousers but soon I freed myself and undid my flies.

Then the disaster happened. Jane appeared in front of me, and I saw her gazing down at my erect penis. I blushed, lost my erection, and stuffed it back into my trousers, She had arrived early, and quietly come in so as not wake her child, and I had been too "busy" to hear to her enter the house. She was not amused. She shut the lounge door and coldly asked me what would have happened if her daughter had come downstairs.

I remember her specifically say "If you want to wank do it on your own time and in your bedroom."

I suddenly became very frightened she would tell my parents, but she was already ahead of me. I remember her telling me she was not sure if she were going to tell my Mum and Dad about my "disgraceful behaviour" and needed time to sleep on her decision, but if she decided to tell them she would warn me first. She paid me for the evening and sent me home. I spent the night and most of the following morning in agonies of waiting until around lunchtime she phoned the house and told me to come to her house because she had underpaid me the night before. I knew this was untrue but virtually ran up the street to her house. She met me at the door, didn't invite me in, but told me that she had found a solution and that I was to come back at 8 o'clock that evening but not tell my parents where I had gone.

That evening after telling my parents I was going down to the pub, I left the house and then doubled back to Jane's door. She let we in and told me were alone and that she had sent her daughter to her Nan's for the night. As we stood in the entry hallway her next words nearly floored me.

"Have you ever been beaten?"

I hesitated. "Yes at school but not at home" I croakily said.

"By whom, how, and what with" she asked.

"Six of the best by the headmaster" I replied.

"On the bare" she asked.

"No, They made us wear thin pyjamas".

She paused. Looked me in the eye and spoke again. "Then this will be a new experience for you because I'm going to cane you on your bare buttocks...twelve strokes".

She instructed me to go to the lounge/dining room take all my clothes off, fold them neatly on the chair and wait for her. A short while later she came into the room carrying a punishment cane about a metre in length with a black leather grip and I noticed for the first time she was dressed in a miniskirt and showing a length of stockinged thigh, but no boots. Despite my predicament, to my acute embarrassment my penis stood immediately to attention, and I put my hands over my groin to cover my nakedness.

She ignored my arousal and told me to bend over the dining room table with my belly over a pillow she had already placed there, place my feet about two feet apart, and hold onto the far edge of the table and not to get up again until she told me to, otherwise extra penalty strokes would need to be given.

I did as I was told and waited, and then I felt her tap the cane a couple of times on my posterior to get her aim, and then the first stroke whistled and bit into my bottom, and a searing pain spread across my bum cheeks. I gasped and jumped up briefly but remembering what she had said, I quickly and firmly grabbed the end of the table in time to receive the second stroke. The pain was agonising, and I started to rise but was able to stop myself from moving further by holding white knuckled onto the end of the table.

"You are not going to be able to hold still are you" she said and bound both my hands to the top of the opposite table legs with two of her husband's colourful patterned ties.

After that she slowly and efficiently completed the caning. The strokes were deliberately given every ten seconds and covered my entire backside and they hurt like hell. By the time she had finished I was sobbing from pain and my torso was damp with sweat. By then my erection had been beaten out of me and she untied me told me to sit naked on the settee to recover and bizarrely she would make us a cup of tea. She came back in a few minutes with a tray and when she turned around my erection had returned.

What she did next was an even bigger shock. She sat down looked at me and I remember she was a little flushed and the tip of her tongue was visible between her lips. She reached down and took my foreskin between thumb and fingers. She said little except "You can't leave with a hard on like this can you." And then she gave me a slow skilled hand job. She denied my orgasm as best she could by stopping and squeezing but I was more horny than I had ever been in my life and after a few minutes I ejaculated over the settee and the carpet.

And then following this, she stood, picked up the cane again and firmly told me I had four penalty strokes coming.

"Two for not holding still and two for the mess on my carpet."

And for the first time I saw the hint of a smile. She made me bend back over the table, "hold on tight," and delivered four extremely severe rapid strokes. These were given within the space of a few seconds and were even worse than those I had received before, and I think the last two were delivered whilst I was standing.

She told me to put my clothes on and drink my tea and then said I should go home. As she walked me to the door she said to me *none of this ever happened, but I'm sure you'll remember your lesson."

Later that night I ran my hand across my heavily bruised and ridged bum, and I wanked myself off at least another two times before going to sleep, once when I woke up in the morning and a couple of times the following afternoon and evening as I replayed the happening of the previous day in my head. By the time I had finished I remember my penis was sore and the foreskin bleeding. My arse took 2 weeks to heal but fortunately my girlfriend was in Greece, and I did not see her for about another 3 weeks when I returned to University.

I never saw her again because shortly after that She and her husband moved house, and by the time I came home at Easter they had gone.

In hindsight Jane set me up. She had a punishment cane in the house, was extremely proficient in is use, and clearly no novice. She knew we would not meet again. In the days following my caning at her hands and my dawning realisation of her hidden character, I did not know whether to feel happy or sorry for her husband.

I have relived the events of that half hour so often that they are indelibly written on my memory, and I am virtually certain that they happened exactly as I recall, although it is now many years on. I never told my current girl friend at the time about what had happened, but later described it to another who became very horny and would ask me to describe it to her when we had sex. Soon afterwards she bought herself a long rattan cane with a leather grip, and a little later we married.