Eddie's Cunning Backfires


by woodenspoon <woodenspoon@innocent.com>

The school had a strict schedule. For the grade sevens and eights bed time was at 9:00 and the boys were expected to have PJs on and be in their beds with their teeth brushed by "lights out" time. Till 9:30 the duty master would walk quietly up and down the halls making sure that everyone was in bed and there was no talking.

One night, when all the boys were supposed to be in their beds, thirteen year old Eddie Peterson was caught out of bed by Mr. Jones, the master on duty. Mr. Jones was too busy to punish Eddie right away so he said to the boy, "Eddie what are you doing out of bed? You know the rules. Now I want you to get ready for a spanking. I'm going to make a quick phone call and then I'll be back in five minutes to give you the spanking you deserve."

Well Eddie sure got ready all right! With the encouragement of the other boys he rushed to his dresser. Someone turned on a small bed side light, and the youth quickly lowered his pants revealing his hairless bottom, legs and young penis. "Quick, I gotta find some underwear", exclaimed Eddie. With a swift movement the boy stepped out of his pajama bottoms and started searching through his drawers for some underpants. He found a pair of white cotton underpants and quickly stepped into them, pulling them up snugly to cover his smooth bum. He then found another pair, which he also slipped on, and one of his friends threw him two more pairs which he put on over top of the two pairs he was already wearing. Now that Eddie was wearing four pairs of underpants he quickly stepped into his pajama bottoms and pulled them up to his waist. The boys giggled among themselves. When the master got back he would give Eddie the swots he had promised but they shouldn't hurt a bit thanks to Eddies careful planning!

After a few more minutes, during which the boys in the dorm whispered excitedly, the master reappeared. This time he had the small wooden paddle he used for spanking the boys. "Alright, master Peterson, out you come!", he called. Eddie came out into the hall and tried to keep a straight face. "Bend over Eddie", Mr. Jones said, "I'm going to give you three swots, you know that you should be in bed at this time of night."

Eddie's pajamas were of the tight fitting variety with the slightly elastic material which stretches to fit many different sizes of boys. Darker coloured elastic cuffs around the wrists and the ankles held the pajamas in place. Because of the thinness and the elastic nature of the material the outline of Eddie's many pairs of underwear was clearly visible when Eddie bent over. Mr. Jones looked at the outline of the underwear and wondered why Eddie was wearing his underwear. The underwear looked a little thicker than normal so Mr. Jones turned on some additional lights so he could see better.

It looked unusual, however Mr. Jones decided to go ahead with the punishment as planned, thinking perhaps the boy was just shy undressing in front of other boys. Goodness knows was a lot of homo_s_e_x_uality the boarding school, so any boy with as soft and cute a bottom as Eddies would need to be careful if he didn't want some other boy holding him down and cornholing him. With these thoughts in mind the spanking was ready to begin.

Mr. Jones brought back the paddle, and while keeping his eye on Eddie's bottom, brought it down hard on the centre of Eddie's buttocks. After just one swot Mr. Jones knew something was wrong. First of all the boy didn't jump, suggesting he didn't feel it, and secondly it didn't sound right. The paddle sounded more like it had hit a pillow than a boys bottom. After ten years of punishing boys Mr. Jones knew how boys reacted to a cut across the bottom and what it sounded like.

"Eddie?", Mr. Jones asked with a pause. "How many pairs of underwear do you have on?" Eddie swallowed. "I beg your pardon sir?" Eddie asked meekly. "You heard me Eddie", continued Mr. Jones. "How many pairs of underwear do you have on?" The boy turned his head to face the master's and said quietly, "Ummm, four I think sir." Eddie knew that it would be better if he didn't add lying to his list of crimes.

"All right then, stand up and face me." Mr. Jones ordered. Eddie did as he was told. "I would like you to give me your pajamas and all your underwear one piece at a time please." Eddie was no longer laughing, he knew he was in for it. His friends listening from the bedroom also knew the plan hadn't worked. Eddie grabbed the pajama bottoms and slid them down to the floor. Eddie handed the pajama bottoms to Mr. Jones and Mr. Jones draped them over his left arm. Eddie then removed his underpants one at a time and handed them to Mr. Jones who counted the number out loud. "One...Two...Three..." said Mr. Jones.

When Eddie got to the last pair he paused and asked, "Ummm, excuse me sir. This is the last pair would you like me to remove them sir?" Mr. Jones nodded yes. When Eddie handed over his last pair of underpants Mr. Jones said, "Four.", and then after a sigh Mr. Jones began speaking slowly to Eddie who was now naked except for his pajama tops. "Why did you do this Eddie?" Mr. Jones asked. "I dunno, I'm sorry sir." said Eddie looking at his feet.

Mr. Jones was still holding Eddie's four pairs of underpants and pajama bottoms and he made no motion to return them. Eddie was pretty sure that this spanking was going to be a bare bottom one. Eddie fidgeted nervously. Mr. Jones looked at the youth and said "Well I'm not very unhappy about this Eddie. It shows a lack of honesty and respect. We have tried to teach you the importance of honesty in our studies yet obviously we have failed. Perhaps some hard swots across your naked bottom will help you to understand. What do you think Eddie?" Eddie hated those questions, there was nothing you could say. He mumbled, "Umm.. It might help sir."

Mr. Jones continued, "You were going to get three swots this evening but in view of the fact that you put on four pairs of underwear how many swots would you say you now deserve?" Eddie could see where things were heading. "Four sir", he replied. "Do you think you need four swots in total or four in addition to the three you were going to get?", Mr. Jones asked with a glance down at the naked boys penis. Eddie was beginning to imagine the painful sting of the paddle on his naked buttocks, yet he knew there was no use arguing, "I think that four in addition would be appropriate sir.", Eddie said.

"All right lets get it over with. Bend over then." said Mr. Jones. Eddie knew this was going to hurt. Trembling he turned to the side, and bent over, exposing his pale white buttocks vulnerably. Mr. Jones put the paddle up against Eddie's naked bottom for a moment while he prepared for the first swing. Eddie felt the soft touch of the paddle and knew that he would not forget the next few minutes for a long time.

Mr. Jones's arm moved back slowly and then descended swishing. SMACK! The paddle hit Eddie's bottom painfully. Eddie instantly recalled how much more painful a bare bottom spanking was to a spanking over PJs. He held back a cry. The paddle descended again, SMACK! "Oh!" cried Eddie. Yet he stayed still because he dared not move. The pain was agonizing and his bottom felt like it was on fire. Each cut of the paddle left a red mark on Eddie's pale bottom. SMACK! the paddle hit again. This time Eddie breathed in sharply and the other boys in the bedroom heard his gasp. SMACK! Another swot at full force left it's mark on Eddie's scarlet bottom. Eddie felt like his bum was burning up, each swot seemed worse than all the rest. Tears filled Eddie's eyes and he mooned a brief "I'm sorry sir." amid snivels. Eddie was now able to appreciate that even light pajamas provide some protection and a bare bottom spanking hurt a lot more. Mr. Jones could see that the spanking was having a beneficial impact on the boy. He brought the paddle down hard on the boys crimson bottom, again yielding a loud SMACK! As Eddie felt the painful sting he shrieked "OUCH!" and stood up from the submissive position. With both hands he rubbed his aching bottom and turned to face Mr. Jones. "Ohh, I'm sorry!" he sobbed.

Mr. Jones stood expressionless and watched the half naked youth in agony. He had been working with naughty boys for years and if he knew one thing is was that you had to be firm with young teenagers. "Eddie, you yourself said that this punishment was what you needed. If you don't bend over right now and take the remainder of your correction we will start again from the very beginning."

Eddie understood, he quickly said "I'm sorry sir, please continue" while crying heavily. He turned, and bent over once again exposing his smarting red bottom for more punishment. Mr. Jones drew back the paddle and said "This is for your own good Eddie." Mr. Jones then brought the paddle down hard on Eddie's quivering bottom. SMACK! "Ouch!" cried Eddie, tears streaming down his face. Mr. Jones brought the paddle back again for the last strike. Swish, the paddle descended. SMACK! It hit Eddie's bottom. "Ohhh!...Ouch!" said Eddie as he jumped upright. He stood for a few moments rubbing his bottom to try and cool it. He gasped for air. The other boys all knew that Eddie had received a good old-fashioned bare bottom spanking and that Eddie was in pain. Mr. Jones handed Eddie back his pajama bottoms and underwear and Eddie took them as he danced in pain. As Eddie crawled into bed he sniveled a little and his roommates knew that they would never risk putting on extra underwear before a spanking.

THE END

NOTE: This is based on a true event at the boarding school I went to.


More stories bywoodenspoon