Diary of a Naughty Boy


by Anonymous

I was a teenager, nearly fourteen years old. My mother had died when I was only eight years old, and my father had maried again, this time a really gorgeous girl og only twenty-one - my new stepmother !

I had been away at boarding school for the better part since they married, but the long summer holiday I spent at home.

During my lifetime I had been incredibly naughty, but had shown great skill in not been found out. I had therefore never received any sort of punishment worth recording.

My father was a wealthy man, and we had a staff which included cook, housemaid and nanny (for my baby brother). The cook was enormously fat, and each afternoon would lie on her bed, having removed her dress, in a purple slip, for a sleep. I could see her from the top of a three in the garden, from which I would peep down and look through her bedroom window.

It was a hot summer's day, and the cook had left the bedroom window wide open. Then I saw a hose, which the gardener had left on the ground by the house. This was too good a chance to miss.

I climbed down the three, turned the hose full on, and directed a jet of icy cold water straight through the bedroom window, onto the enormous figure of cook, lying on the bed.

She let out a scream of rage, leaped of the bed, and slammed the window shut, as I hooted with laughter. The water suddenly ceased coming through the hose, and I turned to see that my step-mother had turned the hose off at the tap, and had witnessed the whole afair.

This time I really had been caught red-handed! This was a test case - if she took no action, I would do exactly as I liked from then on.

"This is the first time you have been caught in the act," she said, "but for a long timeI have been very souspicious of what you have been up to. This time, there is no escaping, and you are going to be punished accordingly. I am going to take you straight upstairs to my bedrrom and smack your bottom. Come with me." She took me by the arm and led me into the house, up the stairs, across the landing, and into her bedroom. She shut the door behind us, and turned the key in the lock. She then placed an armless chair in from of her dressing-table, pulled open a drawer and took out a large hairbrush, with a hard wooden back to it, placing it on the dressingtable within easy reach of the chair.

My step-mother seated herself on the chair, "Come over here" she ordered. I walked over to where she was sitting and stood by her side. "Pull your jersey up - higher than that - right." She unbuckled my belt, undid the top trouser button , and unzipped my flies. She then took down my short trousers, and dropped them around my ankles on the carpet. "Now bend over my knee," she ordered. I lay across her lap in the traditional 'face-downwards' position adopted by one who is going to receive a spanking. My hands touched the floor on the one side, and my toes just touched the floor on the other. My step-mother folded my shirt-tails up over my back, and slipped her fingers under the waist elastic of my pants, which she then pulled right down, and deposited on top of my trousers around my ankles. I was now quiete bare from the middle of my back down to my ankles, and had been fully prepared to receive my first-ever bare-bottom spanking. Without allowing me to slip of her knees, my step-mother picked up the hairbrush from the dressing-table. I felt her place her left hand firmly in the small of my back, to hold me down, and I realised that nothing could save me from the punishment I so richly deserved for my naughtiness.

Before the spanking she was about to administer, my step-mother had this to say: "This is the first time in your life that you are going to have your bottom smacked , This is very much overdue, but I am now going to make up for lost time. By the time I have finished spanking you, you are going to have a very sore bottom, this I can promise you. I am now going to smack your bottom."

I tensed the wobbly cheeks of my bottom , as I saw her raise the hairbrush over her head for the first spank. Then -"smack" as she brought it down in the middle of the right cheek. A pain shot through me. But it was not too bad. Up went the hairbrush and another "smack" rang out, as it landed in the middle of the left cheek. Again I certainly felt it, but again it wasn't too bad. The third and fourth spanks were again on alternate cheeks, and I realised that each cheek would be spanked in turn, initially at least. The spanking continued, and after I had received about a dozen spanks, and my bottom was beginning to turn pink in colour, each spank seemed to be hurting more.

Another six spanks on each cheek, and I found I could not prevent myself giving a cry of pain, as the hairbrush smacked my bottom, which was now a dark pink in colour. I was now really beeing hurt, and allready had the beginnings of the sore bottom my step-mother had promised me. Each spank was deliberate, and stung my bottom, as it was meant to. I kicked my legs to lessen the pain, and tried to roll off my step-mother's lap, but her left hand in the middle of my back held me down too firmly. Both cheeks of my bottom were now 'aflame', as my step-mother relentless continued to punish me. The time had come to give som attention to the surrounding area, not forgetting a few spanks on my thighs, and some well directed whacks soon much increased the area of pain.

To protect my bottom, I took my hands of the carpet and spread them over my inflamed cheeks. the spanking stopped. My step-mother pulled a large handkerchief out of my trouser's pocket, them tied my wrists together in the middle of my back, well above my bottom.

I was really going to get it now - I thought. How right I was ! Up went the hairbrush, and once again the room was filled with the sound of hairbrush smacking a bare bottom, each smack being greeted by a cry of pain. I was experiencing my first-ever spanking , and didn't like it one litle bit! The pattern of a bare bottom spanking was becomming aboundantly clear to me. Innitially the spanks only 'soften up' the bottom, and areal punishment doesn't begin until this period is over. To be effective, a spanking must be prolonged, say for a period of five minutes, during which time perhaps two hundred or more spanks are ministered to the miscreant's bottom. The gratest pain from the hairbrsh commes when it whacks the same spot again, again and again, provided the bottom has been well 'softened up' initially, with a sucsession of stinging smacks. Anyone receiving a smackbottom who only gets a dozen or so spanks is indeed fortunate, as it takes this amount just to change the colour to a pale pink.

The usually wobbly cheeks of most bottoms just 'shrug off' a few smacks, in fact the effect is often stimulating ! A five minute spanking is very different, however, and will leave the bottom 'on fire' and very sore. If the hairbrush 'spanker' is properly applied then the receiver will certainly have to be held down very firmly for the latter part of the spanking, for this is the part which really hurts, as the bottom gets very sore.

These thoughts flashed through my mind, as my step-mother continued with her self-appointed task, in the manner most appropriate to my misdeeds, by giving me a sound bare bottom spanking.

My cries of pain were almost continous, and i frantically kicked my legs, restricted though any movement was, by my trousers and pants around my ankles, in an abortive attempt to move my sore and inflamed bottom away from the sting of the hairbrush. I was too firmly held, however, to escape, and a few well directed smacks on the back of my thighs, where they hurt very much, made it very clear that excessive kicking would attract more stinging smacks in the same area.

Unable to move my arms, discouraged from moving my legs, I was just going to have to accept the spanking I was recieving, without any interruptions! What a very sore bottom she was giving me !

A final six stinging smacks on each cheek, and at last my first-ever spanking had come to an end. How thankful i was, my bottom felt 'on fire!' She undid the handkerchief fastening my wrists together, and said - "You can get up. Pull your trousers up and then go downstairs. I hope you have learned a lesson. Just watch your behaviour in future, or you will find yourself across my knee with your trousers down, very quickly, and you now know what will inevitably follow."

I painfully climbed to my feet, pulled up my pants and trousers, but before doing so, was able to catch a glance of my bottom in a long wall mirror. It was dark red in colour, and seemed so hot, that I half expected it to be giving of steam! She had promised me a sore bottom, how well she had kept promise.

I glanced at my step-mother, who was putting the hairbrush back in the drawer, and saw that her exertions had brought a flash to her cheeks. What a lovely girl she was, with long hair hanging down her back! But what a strong right arm she had, as I had found out to my cost. So there are advantages in being good at tennis! A strong right arm helps your tennis considerably, but is essential for spanking the bottom of a naughty boy. I must be careful, I thought, in future NOT to be caught, the result was too painful ! I had just received my first ever spanking, and had a nasty suspicion that this was only the beginning!

Now that my step-mother had so effectively punished me, I was very sure that I was going to find myself face downwards across her knee, with my bottom bared, very frequently in future. I went downstairs and back into the garden, but this time with a very sore bottom for my naughtiness.


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