The headmaster’s conference

March 26, 2008

This is a fictional story. I am writing about a great fantasy that I masturbate to regularly and all of the characters have had their names changed for legal purposes. I am extremely turned on by spankings no matter who is involved. I would take a spanking from a male or a female and would also give a spanking to either a male or female. I still consider myself straight because nothing else with a male turns me on whereas all the usual things with females turn me on. (breasts, fucking, blow-jobs etc) I just came up with the idea of writing all of my erotic fantasies today after reading a few others from which I find to be the best spanking story website there is with special refference to the stories about Kelly, Jenny, and Adrian Hammersmith. Now that that’s out of the way, on with the story!

If you’d asked me now why I’d done it I couldn’t have told you. I’d earned myself another spanking! On Purpose! I was thinking one day how sexual some points of the smacked bottom I’d recieved from Mrs Alison Lidelle not even a month ago had been. It was Monday and I imagined rather than just sitting in a boring everyday class at school, being smacked hard once again over my “Mistress'” knee. Oh, how it stung! How I cried and begged for mercy, but was just smacked and abused me like the naughty little brat I’d been! I wanted it again. I don’t know what it was about her that made me feel so sexual, but I couldn’t help but imagine once again being ridden (and whipped) like a horse as her warm, moist cotton panties rubbed soothingly on my cold, bare back.

So I waited until no other kids were around then sparked up a cigarette, knowing that a prefect could see me! He ran inside and in no time at all, Mrs Lidelle stormed down to the woods, grabbed me by my ear and began to march me back to her office. Kids watched in disbelief as I was pulled into her office and the door was slammed behind me. Before I could say anything, she pushed me over her desk, pulled my legs back so my bottom was in the air, ready for a good hard smack , yanked down my trousers and my pants and smacked me more than twenty times on my bare, plump little bottom with her hard wooden ruler, each whack making me scream and cry out until I was once again a red bottomed, whimpering mess.

Then, to my utter dismay, without a word she opened the door and left! Fear ran through me as my crimson buttocks stayed facing the door way! I could hear girls gasping and giggling behind me, but I didn’t dare turn around. Around five minutes later the headmaster marched in, slammed the door once again and screamed, “HOW DARE YOU BOY! YOU’VE BEEN PUNISHED BEFORE, BUT YOU CAN CONSIDER THAT A WARM-UP FOR WHAT YOU’LL BE RECIEVING TODAY!” with that he took a long leather strap from his waist and brought it *CRACK!* right across my round behind. It was like the riding crop all over again! My bottom ignited and I Yelped and begged “Soooorrryyy Siiirrr!” “YOU THINK YOU’RE SORRY NOW?! WAIT UNTIL YOU SEE WHAT’S IN STORE FOR YOU’RE NAUGHTY SCHOOLBOY BEHIND!” With that, it was another ten strappings across my exposed bottom.

“Luckily for you,” he continued after my whippings, “I have students coming over from other private schools to learn about our new disciplinarian plan. These children need to see what’s going to happen when they step out of line, knowing that now these delinquents will be sent here for misbehavior to receive legal corporal punishment!” I couldn’t believe it! Surely he wasn’t going to smack me in front of other kids from other schools! He said nothing else. He simply marched me by ear out of his office. Wearing no trousers or pants. I was pulled through a whole corridor, but luckily only teachers saw my well-smacked bottom and my cold so embarassingly small penis. I couldn’t bare to look up and just cried as my wobbling fat red bottom was stared at by all teachers young, old, male and female and by a smiling Mrs Lidelle.

He took me to the side of the assembly hall stage and told me to wait there. I waited in anticipation as the rebelious boys and girls from other schools began to fill up the seats in the assembly hall. I wished that it was Mrs Lidelle punishing me and not the headmaster! At least she smacked me in private and left me with the slightest bit of dignity! (That was, of course, until I wet my panties!) He gave a ten minute speech to the children, which I can’t really remember because I was in such a state of panic, before saying a phrase I’ll never forget. “Now boys and girls, to show you what happens to those who step out of line in my school, I have a very naughty boy waiting for a spanking right here!” Everyone seemed shocked and a few of the boys sniggered, but stopped immediately, so I’m guessing the headmaster must have given them a stern, “You’ll be next” type of look.

Then came the moment I had feared the most, “David get out here right now!” he shouted. Slowly I waddelled towards him in nothing but my school shirt and socks. I noticed he was sitting sown on an armless chair, meaning I’d be going across his knee, so I went over and began to bend over his intimidating lap, not looking at anyone, when he stopped me with his arm. He turned me around so that my punished bottom faced the crowd and I heard everyone gasp. “This is just a warm up for naughty boys and girls in my school.” he said, prodding a finger into the left cheek of my cold backside. “Now I’ll show you how to really warm up a bottom that’s in need of a good seeing to!” I gulped, wondering just how bad my “seeing to” would be. “Over my knee!” he comanded. “oh no” I thought, “here we go.”

As I began to bend over his knee he suddenly pulled my cock and rammed it in between his legs! I felt so humiliated as he rubbed my bottom for a few second before lifting his hand and giving it the first hard smack. My flaming behind re-lit it’s unbearable fire as I shouted out and he began to rapidly smack my bottom. I noticed, unlike Mrs Lidelle he found an area right in the center of my bottom and smacked that spot repeatedly rather than moving around my crimson cheeks. On and on he went for ten minutes on the same spot, not stopping or speaking once, smacking my bottom like a mother would spank her child for not doing what he was told.

My face was almost as red as my bottom with embarassment as the bad kids from the other schools watched with there mouths hanging open as I recieved my smacking. Soon later he lifted me off his lap and told me to bend over with my hands on my toes and my bottom in the air as I was going to be caned! A caning! I didn’t know they actually did that! I thought it was a myth! “Please, no Sir, I’ll be good I promise!” “David”, he said in a quiet, stern voice which I knew would mean I’d be getting more if I didn’t do what I was told. With that I got myself into position.

This was bad enough in itself because the position was awkward and uncomfortable even without recieving a smacked bottom at the age of sixteen in front of alot of troublesome teenagers, some of them girls! He retrieved a thin rattan cane from the side of the stage and without warning, began to smack me with it. It was awful. I cried and cried, not even trying to hold back. I urinated a little onto the floor, but he didn’t say anything, he just caned me harder! The sound terrified me as much as the paint! *SWISH, CRACK! SWISH, CRACK! SWISH CRACK!* My bottom electrified and my warm pee soaked my feet! Why did I always lose my bladder during a smacked bottom?!

I could feel a little blood trickling down my right cheek as the unforgiving wooden cane slashed across my upturned backside. It must have been half an hour of good whipping, hundreds of beats of the cane before he finaly let me get up. He told me turn around to the audience and thank them for watching. I turned to them, but couldn’t bring myself to say anything. He gave my botttom a good hard smack from behind and I yelped and blurted out “Than- Thank you for watching” And walked off the stage crying like a little girl.

I was glad to see the bottom half of my uniform lying at the side of the stage beside a grinning Alison Lidelle. Once again she gave my cock a good stare before saying “Hope you learned your lesson”, smirking and walking away. I watched her firm, curved bottom move beautifully under her skirt, remembering that glorious day when she had ridden me and spanked me, before getting changed and leaving the assembly hall.

On my way out a girl from another school, who had been at the conference approached me. “Oh shit” I thought, “And I thought my punishment was over!” She was thin and very pretty, with a slight emo look about her and alot of lipgloss and eyeshaddow. “Hi” she said, “I’m Sophie.” I didn’t say anything. “Don’t worry” she continued, “I’m sure my naughty bottom will be over that man’s knee too soon.” With that she smiled, winked and walked away.


My First Spanking

March 25, 2008

This is a fictional story. I am writing about a great fantasy that I masturbate to regularly and all of the characters have had their names changed for legal purposes. I am extremely turned on by spankings no matter who is involved. I would take a spanking from a male or a female and would also give a spanking to either a male or female. I still consider myself straight because nothing else with a male turns me on whereas all the usual things with females turn me on. (breasts, fucking, blow-jobs etc) I just came up with the idea of writing all of my erotic fantasies today after reading a few others from which I find to be the best spanking story website there is with special refference to the stories about Kelly, Jenny, and Adrian Hammersmith. Now that that’s out of the way, on with the story!
A teacher had caught me smoking cigarettes at the woods outside of my school. I was escorted to my year head’s office and told to wait outside. I waited more curious than worried as I expected a detention and a phone call to my drunken mother who would do nothing but laugh and ask for a “fag.”

She called me in. I walked in slowly and she closed the door and locked it behind her. I turned to see Mrs Alison Lidelle, a strict and strong woman in her fifties at about 5 ft tall. I became a little frightened just from looking at her. “David, your misbehavior has gotten out of hand for alot of teachers.” I smirked, but stopped as she said, “I am not one of them.”

She then said something I couldn’t believe. “I’m going to give you a spanking.”

A spanking! Did I hear that right?! I was shocked and terrified and knew straight away that my mind must have been playing tricks on me. This is why I simply replied, “what?” To that she snapped “DON’T ‘WHAT’ ME! YOU’RE WELL OVERDUE A GOOD SPANKING AND NOW YOU’RE GETTING ONE! NOW COME OVER HERE AND GET READY!” I argued that she wasn’t allowed to do that and that it was illegal. That’s when she opened her drawer. Inside it was a contract signed by my mother saying that after having 3 detentions the year head was allowed to use any method of punishment she found reasonable.

I swallowed hard and said what would happen if I refused. She said that if that were the case the headmaster would have me stand in front of the whole school on the stage in the assembly hall, bend me over, pull down my trousers and pants and smack my bare bottom with a thick leather belt 300 times and force me to count them and thank him for them after each one. I thought to myself that surely a spanking from a middle-aged woman couldn’t be as bad and so unbelievably agreed that she could spank me in her office. How wrong I was. If I knew what I was in for I would have paid for the other option!

“Okay” she said, “let’s get started. First of all I need you to change into this punishment uniform.” I was confused, but strangely aroused by the fact that this was happening and, giving how crazy the whole situation was I imagined her revealing some form of bondage gear. I was surprised when she revealed a tight fitting girl’s shirt, a school tie, trousers 2 sizes smaller than mine and a pair of tigh thin white cotton panties. “Why must I wear that Miss?” I asked. “DON’T QUESTION ME! And for this punishment you will refer to me as mistress! If you must know, the shirt is to humiliate you and the trousers and panties are tight so that your bottom stings more when I’m giving it a good hard smack!” “Where should I change?” I asked. “NO MORE QUESTIONS! YOU’VE ALREADY EARNED PENALTY SMACKS FOR TAKING SO LONG! CHANGE HERE!” This was unbelievable! She wanted me to change right in front of her! Although I knew I couldn’t oblige or my soft bottom would be spanked even more. Slowly I removed my top and struggled to get on the girl’s one. Embarassingly I have small man-tits and it was chilly so I had nipple erections poking through my top. “Trousers and pants too. Come on get on with it boy!” I felt uncontrolably awkward as I began to un-do my school trousers. What was worse was that I’d gotten an erection from the excitement and my cock stuck out when I lowered them. She just stared and muttered “naughty boy” as I grabbed the wasteband of my boxers and pulled them down revealing my pale bottom and my erect cock. Before I stepped into my punishment trousers I was made to stand for ten seconds with my hands on my head in nothing but a blouse. This was humiliating as she stared at my panis the whole time and exclaimed, “That’s big for a boy of your age.” I felt awful imagining other boys in my year having to do this as well. I quickly pulled on the cotton panties and the trousers but to embarass myself once again I couldn’t do them up. She came over and struggled with them for what seemed like forever until they finaly clipped. “Now,” she said sternly, “Over my knee.”

This was it. I was about to recieve my first ever spanking. I knew it would come one day but never thought it would be like this. She sat down on a tall wooden chair and when I hesitated she grabbed by forearm and thrust me over her professional looking lap. I felt like a child. I stared at the floor with my hands on it to keep balance and my plump little behind perched up in the air. She rubbed my bottom with her firm hand for a moment.This was the first time she’d touched me and it felt amazing.A strict woman’s hand running across my soon to be hot bottom and nothing I could do. For a moment I felt extremely sexual towards Mrs Lidelle. This feeling stopped when she slowly raised her hand. “Are you ready to take this punishment you naughty insignificant slave?” she asked. “Yes mistress!” I said sharply to stay on my spanker’s good side. Then it came the first hard smack across my naughty bottom. My erection went and I yelled out. She smacked me so hard and my right cheek went ablaze. Before I knew it she was spankingme rapidly all over my bottom. I instantly began to cry, but she didn’t stop. I screamed “THAT’S TOO HARD!”

That was a mistake. “That’s it.” she said quietly and she stopped smacking me. I thought she was finishing, but little did I know I’d only just begun. She then pulled out a thirty centimetre wooden ruler from her drawer and hit me across the middle of my bottom with that. It was even worse than the hand! I couldn’t believe it! I thought I could take no more, but just had to! She began to shout as she spanked me with the ruler. “*SMACK* DON’T *SMACK* EVER *SMACK* TELL *SMACK* ME *SMACK* TO *SMACK* CALM *SMACK* DOWN *SMACK* MY *SMACK* PUNISHMENTS *SMACK* YOU *SMACK* NAUGHTY *SMACK* NAUGHTY *SMACK* NAUGHTY *SMACK* LITTLE *SMACK* BOY!” *SMACK, SMACK, SMACK, SMACK, SMACK!*

I cried and cried knowing that my bottom was going to be punished for alot longer now! She then said, “Get up” I slowly got off her knee and stood up, still whimpering like a little three year-old who’d just been smacked by his mummy. I began to rub my bottom and she exploded! “HOW DARE YOU?! DID I SAY YOU COULD RUB YOUR FAT LITTLE BOTTOM?!” “no mistress” I sobed quietly. “Right, I’m going to have to heat you up again before the next stage of punishment.” I only had a second to think about what sort of awful punishment could be in store for “The next stage” before she forced me to bend down and touch my toes then smacked my bottom with the ruler another ten times before letting me up. I cried again and felt humiliated having just been spanked over my teacher’s knee!

Things just got worse. Next she took out a wooden paddle, dark wood and about half the length of a cricket bat. I stared at it in shock as she said, “Oh yes, now things start to get fun!” Before she began she approached me from behind and slowly rubbed the crotch area of my trousers to deliberately make it hard which embarassed me even more, but I did nothing to stop her in fear of an extra smack! “Now bend over and place your hands on my desk” she ordered. I did so traight away. “Perch your fat arse out more lad, or I’ll get the headmaster in here too!” I did so very quickly to make sure no one else saw my smacking, even if the whole school could hear me cry.

Once again she rubbed my bottom, this time with the paddle before bringing it *SMACK* right across the center of my flaming behind. This time I actually yelled out as the pain blasted across the whole of my plump and very well-spanked bottom. For about another twenty minutes all you could hear was “*SMACK* AOOWW! *SMACK* AOOWW! *SMACK* AAAAAAAAAAAHHHHHHHHH!”

Then the worst thing that could possibly of happened did happen. I needed to urinate. REALLY badly. “Mistress,” I said. “What?” She replied. “I really need to pee.” I said. What she said next frightened me the most out of anything she’d said all day.

“Then pee.”

“What do you mean?” I replied, completely confused. She smacked me again and shouted “PEE!” I was the most shocked I’d been all day. She wanted me to wet myself right there in her office! SMACK! Down came another violent slap from the paddle. ooohh how it hurt! “I SAID PEE YOU NAUGHTY BOY!” SMACK! another spanking and my bladder couldn’t hold back any more. My cock burst with hot, steaming urine and it flooded into my panties and ran all down my leg in my tight trousers leaving a wet stream stain on the leg and I began to cry once again feeling like a little child once again as a puddle began to form at the bottom of my warm, wet socks. She placed the paddle to the side and came over to me. She smacked me another six times with her hand on my bottom, which was still perched in the same position before pressing up against me from behind and bending down and rubbing my thighs down using both hands. I was disgusted as I noticed her licking her hand afterwards. “This is the first time a nughty boy has wet himself in my office”, she said, “And this mess is just unacceptable.” I just stood crying with my face in my hands, too embarassed to reply. She smacked me 12 more times with her hand really hard. I squealed and she told me I had to clean up the mess I’d made or I would be punished in front of the whole school by the headmaster. I felt sick, but replied with another simple, “Yes Miss.” Not thinking. This annoyed her and she revealed her next spanking toy.

It was a riding crop. I didn’t have time to think before I was throwen back across her desk and whipped multiple times across the center of my roasting rump. She shouted “I *THWAP* TOLD *THWAP* YOU *THWAP* TO *THWAP* CALL *THWAP* ME *THWAP* MISTRESS!” *THWAP! THWAP! THWAP!* I cried and bawled, “sooooorrrryyy Mistress!” “Now it’s time for your cleaning duties! If you think you’ve had a rough spanking before just wait until I have you on your hands and knees!” With that she came over, unclipped my trousers, pulled them down, smacked me once on my panties before yanking them down, had me take of my top and stand there wearing nothing but my urine soaked socks.

“Now down on your hands and knees you fat little dog!” I couldn’t believe this abuse, but obeyed my mistress and bent down on my hands and knees, right in front of the puddle I’d made when I’d wet myself. She told me I was to use my punishment uniform to soak up my mess so I began by using my panties (which I had just noticed had frills on them and therefore were in fact more women’s clothing) and soaking up the puddle from it’s edges. Then something happened that once again gave me an erection purely out of disbelief and adrenaline. Mrs Lidelle climbed over onto my bare back with one leg on each side! IN A BUSINESS SKIRT! I couldn’t believe the feeling. I was disgusted because this woman generally had no sexual attraction to her, yet I couldn’t stop mmyself from being so turned on! This was the most a female had ever done to me and although I was about to be punished it felt so great for just a few seconds, those warm smoothe thighs in those beautiful see-through tight. oooohhh and the panties! You wouldn’t believe the panties! Nice warm, soft cotton rubbing on my back, knowing that a vagina was right on me with only a couple of milimetres of cotton on between us! Then came the smacked bottom.

Once again, like letting air out a balloon the erection left as she brought her riding crop aross my bare bottom! It was like torture. I’d never felt anything so painfull! I’d have given anything to have gone back to the paddle with clothes on, even if I had to stand in my own urine. I screamed. I couldn’t stop screaming. I screamed like a bratty little girl who’s daddy had just had enough, taken her across his knee, pulled up her skirt and belted her! I’d been such a naughty boy for so long. Getting cocky with teachers and, of course, pissing of my year head. Now I was paying for it. “I thought you’d like it.” she said. I hated her, but loved her at the same time at that point. There I was with a woman all over me, her panties rolling across my back, she’d even gone a little moist I noticed, but at the same time she was whipping me like an animal and she knew she was getting to me.

For the next hour she spanked me non-stop with the whip saying “you naughty, naughty boy, you naughty, naughty boy!” My bottom was bleeding slightly and I felt faint and couldn’t condure up anything else to say. I didn’t even have the energy to cry so I just whimpered. She then stopped. She began to walk forward, rather than dismounting me, meaning that for one heavenly moment, her moist panties strode up the back of my neck and glided across the top of my head. I had finnished cleaning up my puddle. “Get up you punished little brat, I have one last thing I want you to do!”

“Oh no,” I thought, “no doubt she had an even more painfull spanking implement!” I was surprised when instead she took my wet girl’s panties and made me step inside them then pulled them back up. This time they were cold, wet and stinking all over. She then took off her bra! I couldn’t believe what I was seeing or just how screwed up this whole day was! Unfortunately she managed it without removing any other clothing so my cock didn’t harden to much… until she soaked it in my urine and put it on me! It was warm and felt so sexual I almost ejaculated! She then made me put on the blouse which was also drenched in my pee. She reached under her desk for what I thought would be a spanking implement, but was actually a tartan skirt!! This was uncontrolably farfetched. She made me wear it!

“Now I’m going to treat you like a naughty girl, do you understand me?” I didn’t know what to expect, but off course said, “Yes Mistress” “Right then” she said as she grabbed my arm, walked me to the chair and took me back across her lap. At this point I feel so naughty, dressed in a naughty schoolgirl uniform, wearing another woman’s bra, soaked in warm urine all over and, off course, over a lap about to recieve the smacked bottom that every schoolgirl deserves!

She lifted my skirt slowly then bagan to rub my wet bottom, just on the panties this time. It felt so good. “I’m going to give you a little smack to before you leave because you’re a very naughty girl. Understand?” I was confused to what a “little smack” was, but found I would thoroughly enjoy it, rather than hating the pain a “naughty boy” recieves.

I asked nicely if she could be quick because I needed to use the bathroom again and didn’t want to make any more mess. She gave me the best reply I could have asked for at that moment. “I’ll take down you’re panties and you can wee on my lap.” This woman was nuts! But for some reason I couldn’t wait to stay across her lap and get to share that moment with her when I peed! Slowly, she rolled my panties down to my ankles and began to smack. But it wasn’t like the smacks before. It was gentle and loving. I wished I could have stayed over her lap forever and just never get up. It felt so good. I felt like a naughty boy, being punished, but through love and care rather than abuse. The warm pee came slowly. It was the greatest feeling ever. She didn’t mind at all and just kept smacking my plump red behind softly. The warm urine ran onto her skirt and created a warm puddle to soak my penis in.

When I was finished she let me up. I changed into my normal clothes again quickly and ironicly she wrote me a detention slip. “I just need to ask one more thing,” she said, “Have you been a naughty little boy?” “Yes Mistress.” “Are you going to behave now to avoid future smackings?” “Yes Mistress.” “Good, then you can leave.” She unlocked the door and on my way out she gave my bottom a cheaky little smack.

I hated that dayy, but was glad that I had recieved a spanking and knew what I was in for if I ever got on the wrong side of Alison Lidelle again!

Hey, smoking’s not just harmful to your lungs, It can be harmful to your bottom too if you’re not careful!”