The Making of a Masochist

Author's Note: This is a story. If you are offended by descriptions of strapping, birching, or caning please do not read on. All of the participants in this story are adults over the age of eighteen years. As usual none of the characters depicted are real and any similarity to real places or people living or dead is purely coincidental.

The events described in this story happened over sixty years ago in a world with very different moral and social values and this story should be read within this context.

Preamble

The reasons why so many of us have fetishes are varied and complex. Are we born with certain sexual preferences, do events in our lives drive them, or is it a combination of both?

I am a masochist. I have a deep need to have my bare bottom disciplined by a woman wielding a cane, strap, paddle, or whip. I want the punishment to hurt badly and leave my bottom badly bruised, welted, or deeply ridged. I don't want to be maimed, slapped, kicked in the balls, or hit anywhere else, and I don't want to be tortured or hurt in any other way. Neither does bondage do it for me, although I prefer to be tied down for a sound thrashing of my bare buttocks.

My wishes are simple.

I need real and severe punishment when the pain is awful whilst it is happening. Eventually, when I reach subspace the pain becomes pleasurable.

And after I have submitted, and I run my fingers across my bum cheeks so ridged they feel like corrugated paper, or I look in the mirror and see them glowing bright tomato red I feel as horny as hell.

First experiences

I attended a minor public school in the fifties and sixties, and I doubt you have ever heard of the place. Twenty years on, I still get a magazine sent to me every year or so inviting me to become a member of the Old......ians and describing the yearly reunions, the improvements to the new science block or squash courts, the demise of old staff or students, or the achievement of the still living. They are proud of the forward-looking education they provide for both girls and boys, but when I attended the school it was a very different time and a very different place.

I had been sent to boarding school because my father was an officer in the army and was constantly on the move. By the time I was eight years old, I had attended half a dozen different schools and my parents decided I needed more stability in my life. And so when I was just turned eight I was packed off to boarding school in England. Because the Army was paying I was sent to a cheap third-rate establishment.

At the time It was an all-boys school and life was hard. Discipline was extremely rigid and corporal punishment was extremely widespread. For minor infringements, four with the plimsoll on your trousered bottom might be considered appropriate whilst more serious misdemeanours would often result in six strokes of the cane applied whilst wearing pyjamas. These punishments would be carried out in the housemaster's study in private before bedtime. The punishment of the final resort was a birching, but when I was in my final year at school I had never known this punishment to have been carried out during my ten years there. I had, of course, been caned on many occasions over the years and I can assure you it is a painful and quite unforgettable experience.

I was one of the older students at the school and had turned eighteen years old just after Christmas in my final year at school. I was a good student and was studying for my A levels that Summer, following which I planned to go on to University. Despite my comparative maturity, I was not a prefect. I think this was because of my quietly rebellious spirit and that I was a loner, liked my own company, and had very few friends.

At that time, as an upper-sixth student, I had more freedom than most of the younger boys and had my own study-bedroom and a key to the house where I resided. I was allowed into the small local town unsupervised, but was meant to wear school uniform at all times and only leave the school grounds at strictly proscribed times and be back in the house no later than nine p.m. Under no circumstances was I permitted to enter a pub or bar. This would have been quite impossible anyway since the publican would almost certainly have reported me to the school's headmaster.

***

I also had a secret. I had a girlfriend, and this was an incredibly risky thing to do. I met Natalie whilst I was walking along the river one day in early January and had gone behind a boathouse to have a cigarette when Natalie appeared. She was short and slightly plump but very pretty with big brown eyes and hair and spoke with a broad West County accent. I remember she followed me behind the building where I had gone for an illicit smoke and had asked me for one, after which we started to talk.

She was a twenty-year-old "townie" who worked as a barmaid but aspired to leave the town where she felt trapped, and I think that was why she was originally attracted to me. That first Sunday afternoon we only talked for ten minutes when she suddenly looked at her watch.

"If I don't get home soon my parents will want to know where I've been. They know I finish around three o'clock and they'll want to know where I've been. If they think I've been talking to a boy from the school my mum will take the strap to my bare bum. Thanks for the cigarette. I walk this way every day at this time but Tuesdays. Bye."

And then she was off down the towpath. As she walked away I watched her big round bottom and tried to imagine her skirt and panties being removed and a leather strap being vigorously applied to her wriggling cheeks... and I grew hard.

The following Wednesday I cried off rugby with a sprained wrist and just before three o'clock arrived at the boat house and, a few minutes later, Natalie came past. After that, we started to meet two to three times a week, following which Natalie would hurry home.

We were both taking a risk. In the early sixties, there was a huge social divide between public school boys and pupils of state schools. They considered us to be upper-class snobs and we thought of them as common. Fights between "townies" and my classmates were common. It was the era of the Teddy Boys who would have been only too happy to give me a hiding if they caught me with Natalie.

For her part, Natalie was risking the wrath of her parents in seeing me and was also risking a good hiding. I was very happy she had no brother or sister to disapprove of me.

About three weeks later, one Saturday afternoon, we met as usual. Nancy was in a hurry but also very excited. "My parents are leaving this afternoon for Plymouth. My Mum's sister is very ill, and they'll be away until at least Monday morning. I've told my boss I've got to look after the animals on the farm. We've got today and tomorrow to ourselves. Can you come over in about an hour? You know where I live in Moor Farm. It's a half mile down the towpath on the right You can't miss it.... For fucks sake don't be seen."

She was gone before I had time to think but an hour later I knocked on the farmhouse's back door. To this day I can't say what I expected but I will never forget what happened next.

***

Natalie let me in, and no sooner had she closed the door behind me than she started to kiss me. I felt her push her tongue into my mouth and I kissed her back and pulled her towards me. Her breasts pressed against me as I held her tight, and inevitably I started to harden.

I was a virgin until that afternoon, but Natalie was most certainly not. I felt her hand reach down, open my zip, and take me in her dainty hand. I don't think I had ever been harder in my life than I was at that moment and would have probably disgraced myself and come in her hand just from her touch had I not had a wank earlier that morning. I ached for her to start to rub me, but she didn't. Instead, she stood back and looked down at my rock-hard erection protruding from my trousers.

She was flushed and moist-lipped as she spoke. Oh My. Is that all for me? I'm not wasting that in my hand. Come with me.

She led me upstairs to her bedroom. It was a small windowless room with an old iron bedstead standing against one wall with a mirrored double wardrobe standing opposite it. On one side of the bed was a rickety wooden chair and on the other side a small bedside cupboard with an alarm clock standing on it. There was nothing on the bare white walls except an evil-looking leather strap hanging on a hook on the wall. It was made of well-worn dark brown leather about a foot and a half long and 4 inches wide with 2 parallel rows of four performed holes at its end. This strap was attached to a wooden handle which was whitened by age and sweat. The handle had a loop of leather attached to it by which it hung in place.

We entered and she locked the door behind us. Then she started to undo her dress, stepped out of it, and pulled her sweater over her head. She stood in front of me in white ankle socks, a white bra, and panties. We must have looked ridiculous. I was still wearing my school uniform of trousers and jacket with shirt and tie, but my erect cock was protruding in front of me.

"Take off your clothes," she said, as she unclipped her bra and removed her socks and panties, and I didn't have to be told twice.

Soon we were both naked. I had never seen a woman naked before and was trembling with excitement as I looked at her large pale breasts and her hairy sex. She had thick thighs and a round flabby arse.

And I knew I was going to fuck her!

She bent over and retrieved a small paper packet from under her pillow and as she did I had a glorious view of her bum and slit.

"Put this on. I nicked it from my Dad's bedside drawer."

It was a condom. I had never seen one before and my inexperience must have been obvious because as I fumbled with it Natalie took it back from me and quickly and skilfully rolled it over my erect member.

She lay back on the bed with her legs spread and knees bent. "Put it in me. I don't need foreplay. I'm so fucking wet."

I lay between her legs and felt her take my dick in her hand and guide me inside her and, for the first time, I felt the warm grip of a vagina around me. I knew what to do and started to move in and out of her. My strokes were long and smooth and made easy by her copious secretions. Then she started to moan and then talk, and I increased my pace. The old bedstead started to rhythmically bang against the wall as I banged Natalie, and her cries and entreaties became more strident.

"Like that. Like that. Just like that!"

"I love. it I love. Oh, how I love it!"

"I'm going to come! I'm going to come! I'm going to come!"

"I'm coming! I'm coming!"

"Ohhhhhhhhhhhhh!"

And for the first time, I watched a woman take her orgasm. Her face flushed, her eyes widened, and her mouth formed a perfect o, as I felt her drive her perineum against me.

As her passion had grown so had mine, and as she took her climax I shortened my stroke, my penis pulsed rhythmically, and I groaned and collapsed over her.

Natalie was not finished and over the course of the late afternoon, my sex education continued. She showed me how to use my fingers to rub her clitoris and as I took her beautiful tits into my mouth I masturbated her to climax and watched her writhe in pleasure. Then she sat on a chair and had me kneel between her thick thighs and lick her to a further orgasm.

A little later when I had recovered she gave me the first blow job of my life. Before she started she asked a question.

"Have you ever had a blowjob?"

"Is it that obvious?"

"Everybody has to lose their cherry sometime honey. Nothing to be ashamed of. I'm told I do a great blowjob so lie back and enjoy it."

Then she leaned over and retrieved something from under the bed and handed it to me. "My kink. It's a polaroid camera. Take two. One each. A souvenir of your first blow job. I can't promise to say cheese I'm afraid." And she giggled.

I lay on my back, and she knelt facing me and took me between her lips, and with her bum in the air and her tits swinging she used her mouth and tongue to fellate me. She watched me intently as she worked, taking me to the edge and then away from it, and smiled with pleasure at my need. I thought I had died and gone to heaven. Then when I could suffer no longer I came, and my penis pulsed its milky load into her mouth, and she grinned in triumph.

The following morning it was Sunday so Church was obligatory. After lunch, I returned to Moor Farm and my lessons continued. The curriculum included Natalie on top, doggy-style, and soixante-neuf. I was a happier and wiser young man when I returned to the house later

After that weekend we did not get a chance to screw for several weeks. It was utterly impractical for us to hire a hotel room, taking Natalie to my room was out of the question, the weather was freezing and any attempt to get naked outside would have resulted in frostbite and permanent damage, and Natalie's Aunt had suddenly and miraculously recovered.

One Sunday afternoon we met at the boathouse and Natalie told me her parents had gone to Exeter to look at livestock and would be away until late evening and shortly afterward were both naked in her bedroom. Natalie was insatiable and I fucked her to orgasm twice in the missionary position before she climbed on top of me and rode me to further climax. It was only when she knelt for me to take her doggy style that I saw her bum. Each of her bum cheeks bore the bruises of a spanking and was traversed by dark blue oblong bruises.

I said nothing but gave her more of what she wanted whereupon she turned, removed the condom from my prick, knelt, and took the entire length into her mouth. She used her lips and tongue to take me to the edge before head bobbing, her eyes watching my passion, she took my cum and swallowed it.

***

A little later I asked her about the marks on her bottom. She snuggled up to me, put her head on my chest, and started to speak.

"Although my parents have always been very strict, up until I was eighteen neither of them ever raised their hand to me. Then about a year ago, things changed, and my mother bought that strap. The one hanging on the wall. My mother calls it the "corrector." "An adult instrument for an adult's sins," she says. She first used it on me when I kissed a boy. She used it on me last Christmas when I came home from a party two hours late, and two days ago when I told her to go fuck herself.

She's a cow. A mean bitch. She's always been selfish but lately, she's got worse. My father has always given in to her and she always gets her way. She wears the trousers in this house. I just wish my father would grow some balls and stand up to her. It's too late. He never will but that doesn't mean I have to.

She's very religious and into the sins of the flesh and so on. I think she imagines I'm having it away with every man I meet, and the thought horrifies her. I've decided that when I've saved enough money I'm out of here. For the moment I just have to put up with it. I've nowhere else to go.

She has a routine that never varies. When I'm to be punished the strap disappears from the wall. I have a shower and put on my long black dress with a bra but no panties. In the evening at ten o'clock exactly I lie over the kitchen table and my father stands at the far end and holds my wrists. Then my mother pulls my skirt up and over my head exposing my bare bum and pussy to her, but not my spineless prudish Dad, and she gives me half a dozen with the strap. Then I'm sent to bed.

"What will they do if they find out about us?" I asked.

"Don't even think about it," she replied.

Found out

But find out they did. I suppose it was inevitable. Let's face it, human beings have ignored the consequences of illicit sexual liaisons for thousands of years, and we were no different.

The problem was contraception. Not because we weren't using it but because we were. Neither Natalie nor I could easily buy condoms. I couldn't buy them from a chemist or enter a pub to access a machine in a male toilet and she had a similar problem. Our solutions were twofold; withdrawal, and theft from Mr Evans's supply. Natalie would remove the occasional one from his bedside drawer and hope he wouldn't notice. Until one day in early April he did, and then mentioned it to his wife.

It was a Saturday afternoon and Natalie's parents told her they would be away for the afternoon and evening, and we had taken our opportunity. She was bent over the end of the bed, and I was fucking her doggy-style when the bedroom door was flung open, and I made my acquaintance with Mrs Evans.

She screamed, "Natalie what are you doing?" Taken by surprise I looked across at Mrs Evans, withdrew my rapidly wilting dick, and knelt open-mouthed as Natalie turned and tried to hide in the bed sheets.

"Get dressed and come downstairs."

When Natalie and I reached the kitchen five minutes later Mrs Evans was already drinking cooking brandy from a tumbler. She was trembling with anger. Mr Evans was much calmer and sat quietly at the kitchen table.

"I knew she was fucking someone she," said. "She's been stealing your Durex. You slut! You fucking little slut!

Then she turned to me. "And who the fuck are you?"

"Martin, Mrs Evans."

"Well Martin whomever the fuck you are, if I was a man I'd give you a sound beating. But I'm not and my man is bloody useless. So fuck off out of my house and don't come back. I'll be talking to your headmaster first thing Monday. Go to your room, Natalie. I'll deal with you later and I SHALL beat you.

The Choice

Late on Monday morning, I was in the chemistry laboratory completing an experiment when the headmaster's secretary came into the room and spoke to Mr Gordon, the chemistry teacher. I saw him nod his head gravely, and when the secretary had left he called me over.

"Walters... Finish up what you are doing and then go directly to the headmaster's office. Be sharp about it and don't keep him waiting."

I did as I was told, and it was with a great deal of trepidation that I spoke to the headmaster's secretary who sat behind a large wooden desk in the anteroom outside the headmaster's study. She was a plump middle-aged lady with an unsmiling face. I didn't have to introduce myself.

"Take a seat, Mr Walters. I'll tell Mr James you're here."

She knocked on his door and I heard his voice. "Come," and she entered.

After a few seconds, she reappeared. "He'll see you now."

I walked into the study, and she closed the door behind me and I almost immediately I realised I was in deep trouble. Sitting in the corner of the room was a very angry-looking Mr Evans and an even angrier-looking Mrs Evans

Mr James spoke first. "Do you know why you are here? Mrs Evans says she found you in bed with her daughter. Is this true?"

I swallowed hard ."Yes Sir."

"So you admit to seducing her daughter?"

There was little point in telling them that Natalie, with negligible effort, had seduced me.

"Yes Sir."

"Very well. Mr and Mrs Evans are understandably very angry indeed. As am I."

"Yes Sir."

Do you have anything to say in mitigation?

"No Sir." (Later I wondered what he would have done if a big-arsed, big-titted, and pretty young woman had offered him sex on a plate when he was my age.)

"You have led a young girl astray and brought dishonour to this school and I am minded to expel you from the school. However... as serious as your offense is I do not believe expulsion, which would blight your entire life, is an entirely appropriate punishment. Mr Evans tells me his wife has already taken the strap to Natalie and they want me to birch you. Simply put you have a choice. Accept a birching or face expulsion.