Thomas Wright's School Days
By Kylie
Copyright 2010 by Kylie, all rights reserved
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This story is intended for ADULTS ONLY. It contains explicit
depictions of sexual activity involving minors. If you are
not of a legal age in your locality to view such material or
if such material does not appeal to you, do not read
further, and do not save this story.
* * * * *
Samantha Warren watched her teacher, Miss Fletcher, leave the classroom. The 10-year-old
girl and her two classmates had to stay after school to wash the blackboard and clean all
of the erasers. She had been caught passing a note in class, while 14-year-old Thomas
Wright and 11-year-old James Morgan had talked in class. Luckily, Miss Fletcher was a
kindly schoolmarm and chose not to use the strap. When Mr. Johnson had been the
schoolteacher at the rural, one-room schoolhouse, the strap would have come out
immediately and the boys' britches would have come down immediately as well. But Mr.
Johnson had been taken by the Scarlet fever two summers ago, and he had been replaced by a
more progressive schoolteacher, who decried the "backwards thinking of the 18th century
now that we are more than halfway past the 19th century," as Miss Fletcher often remarked.
As James slammed the erasers onto the wood floor, dispelling clouds of chalk dust with each slam, Samantha stood on her toes in an effort to reach the top of the blackboard. Thomas winked at James and rushed at the girl, knocking her to the ground. In a moment, he was sitting on her back and Samantha found herself pinned to the floor by the weight of the older boy. Frustrated, Samantha slugged Thomas' thigh with her fist.
"You cannot get me off you that easily," Thomas said. "But hitting me was very naughty, was it not, James?"
The younger boy nodded. "For that, you would surely get the strap if Miss Fletcher had seen you."
"Let me up, Thomas," Samantha cried.
Ignoring her plea, Thomas said, "I shan't use the strap on her, but she still deserves a spanking." He pulled the struggling girl's dress all the way up to her waist, revealing her drawers. "I think this offense calls for a bare bottom spanking."
"Do not dare touch my drawers, Thomas Wright!" the young girl cried to no avail.
Thomas smiled as he leaned over and edged the helpless girl's drawers down, exposing her bare buttocks. He stared at her virgin white flesh and pictured it reddening with each smack of his hand. "How many whacks do you think you deserve?"
"None!" Samantha cried.
"But you struck me, did you not?" Thomas asked.
Samantha hesitated. "Yes, but..."
"No buts," Thomas replied. "Except for your butt, which shall be turned a nice shade of red in a few minutes. The only question is whether you receive 15 whacks or five. Which is it to be?"
The helpless girl knew she was trapped. Miss Fletcher had gone for the day and James was merely a bystander, neither aiding Thomas nor coming to her rescue. "Five, then," she replied reluctantly.
"If you wish five smacks, then you must ask properly for them," Thomas said. "Repeat after me: 'I am a naughty girl and deserve a good spanking. Please, Master Thomas, apply the palm of your hand most forcefully to my waiting bare butt five times.'" He paused. When she made no reply, he added, "Or I could simply give you 15 of my best."
Samantha struggled futilely to free herself and then ceased her writhings. Admitting defeat, she said, "I am a naughty girl and deserve a good spanking. Please, Master Thomas, apply the palm of your hand most forcefully to my waiting bare butt five times."
"With pleasure," Thomas said, bringing his open palm down upon her buttocks. With each smack, the blood rushed to her plump posterior until, by the fifth smack, her once white butt was now a glowing shade of red.
"I bet that must sting like the Dickens," James said. "Are you going to make her stand in the corner holding up her hem until it fades?"
"I should, but I wager she will run out the door the minute I get off her," Thomas replied. "Besides, I would rather she hold her hem up and face us, so we could see her privates as well." Thomas smiled wickedly. "Of course, we can still see her privates." Ignoring her struggles and protests, he rolled her onto her back. With her drawers already pulled down to her knees, Samantha could do little but stare at Thomas' back as he drew the front of her dress up to her waist. As her hem crept up, Samantha's legs slowly gave way to her thighs and then to her hairless vagina.
"I will get you for this, Thomas Wright! I will see you stripped and whipped. I will not rest until every boy and girl in school has seen you sprawled across Miss Fletcher's desk, naked as the day you were born! I shall thoroughly humiliate you, Thomas Wright!"
"It is humiliation you seek?" Thomas asked. "Then how about this? Watch carefully, and learn, James," he told the younger boy, as he slipped his finger into Samantha's vagina. Try as she might, Samantha could not deny the pleasurable sensation that wracked her body. Her breathing hastened and soft moans escaped her lips, to the delight of the two boys. As Thomas entertained his audience, the mortified girl closed her eyes and lay on her back, dreaming of revenge, in between her moans and sighs.
The next morning, Thomas arose at 4 a.m. and walked to the barn to milk the cow and do the rest of his morning chores before the walk to school. He was surprised to find Sarah Carter, a 13-year-old classmate, waiting outside his barn.
"What are you doing here?" he asked.
"I brought you a message from my sister, Margaret. She told me to give you this letter."
"What does it say?"
"I have not read it! It was not mine to read and she chose not to share its content." She handed him the letter.
Thomas' jaw dropped as he read it. It read: "Do not tell my sister, but by the time you read this, I will be swimming in the lake behind the old Ranson barn. If you hurry, you may still find me in the barn, waiting for my clothes to dry. You may help me pass the time until my clothes are once again dry enough to wear to school."
Margaret Carter was an attractive 15-year-old girl who sat two rows in front of him in class. As one of the older girls, she was one of the few with fully developed breasts, and Thomas had often daydreamed in class about what they might look like beneath her pinafore dress. "Your sister really wrote this?"
"Do you not recognize her hand? You have copied her test answers often enough."
Thomas nodded.
"Is it true what Samantha Warren told me? Did you really pull her drawers down and spank her bare butt?"
"She told you that?" Thomas asked, surprised.
Sarah nodded. "Is it true?"
Thomas stuffed the letter in his pocket and replied, "Yes, and I shall do the same to you if you tell anyone about this letter. Now go home."
Sarah turned and walked away. She stopped and turned around. "Samantha was right. You are a naughty boy, Thomas Wright."
Thomas laughed. "Not yet, but I will be very soon." He headed off to the old Ranson barn.
The bank had foreclosed on Mr. Ranson's property last winter, and the barn had sat untouched since the day he left, making it an attractive place for children to play. The sun was not yet up, so Thomas had to rely on moonlight to find his way to the barn. He swung open the heavy wooden door and stepped several feet into the barn. His eyes were still adjusting to the darkness but his form was silhouetted by the moonlight shinning through the open door.
"Margaret?" he called out into the darkness.
"Get him!" he heard a female voice call out. In seconds, Thomas found himself under a pile of bodies. "Light the lanterns!" the voice cried.
Three lanterns were lit and hooked onto nails at various spots in the barn. As it filled with light, Thomas saw that a ring of five girls he knew from school surrounded him. He assumed the three large girls on top of him were also classmates. He recognized 13-year-old Jane Holter, 14-year-old Sally Folger, 13-year-old Sophie Folger, 12-year-old Elizabeth Brennan, 10-year-old Mary Brennan, 11-year-old Kate Morgan, and the Carter sisters, Sarah and Margaret. Sarah apparently had taken a shortcut to beat Thomas to the barn.
"What is going on here?" Thomas asked, as Jane, Sally, and Sophie climbed off him while pinning his arms and legs to the floor.
Samantha Warren stepped out from behind a bale of hay. "I told my friends what you did at school yesterday. They are very unhappy with you, especially since they know you might do that to any of the smaller girls."
Thomas looked up at the angry faces staring down at him. "What—what are you going to do to me?"
Samantha grinned. "I already told you what I would do to you, 'Master' Thomas." She looked around at her friends, and shouted, "Strip him!"
Elizabeth and Mary rushed to Thomas' feet, still pinned down, and gleefully pulled off his shoes. Then they slid down his long dark-colored, over-the-knee stockings and waved them in the air victoriously, leaving the boy barefoot. Kate helped Jane remove Thomas' jacket while keeping at least one of his arms pinned at all times. Sarah Carter unhooked his suspenders and, as Jane and Sally took turns temporarily releasing his arms, her sister Margaret pulled his white linen shirt over his head. Sophie pulled off Thomas' knee pants, leaving the restrained boy clad only in his drawers.
"Fine, you have all had your fun," Thomas said. "Now release me and we shall say no more about this."
"But Master Thomas, we are just getting started," Samantha said coyly. "We cannot wait to see more of you."
Thomas' face reflected his shock. "Then you mean to strip me bare as I lie here helpless to defend my modesty? You would expose my privates to near every girl in school, knowing that in future I will never be able to look upon their faces without the realization that they are picturing me naked from head-to-toe?"
Samantha smiled. "Little boys should not be so modest."
"But I am not a little boy; I am four years older than you, Samantha."
Samantha flashed another wicked smile. "Older than me you may be, Thomas Wright, but I bet you are still a little boy. We shall ask all of the girls here if they agree. Now, let us see how little you are, boy!" Samantha tugged at his drawers. Thomas watched helplessly while his short and curly pubic hairs popped into view, as the young girl gleefully but slowly pulled down his drawers.
"Gosh, he has more hair than me," Kate said.
"It is not fair that he should have any when I have none yet." Samantha pouted.
"Then tis a good thing I thought to bring this straight-edge from our father's barbershop," Margaret said. "Sarah and I have observed him shave men's faces our whole lives. We could easily shave that small clump of hair off."
"No!" Thomas cried, horrified.
Seeing Thomas' distress at the idea, Samantha said, "Yes, once Master Thomas has been completely exposed before all of us, you shall shave his privates until he be as bald as any boy not yet breeched. In fact, he should not go to school breeched today. Sally, you gather his britches and the rest of his clothes and bury them in the woods. We shall escort Master Thomas to the schoolhouse in the dress that Margaret brought."
Boys always wore dresses like girls until they were about five years old, when they started wearing britches instead. Thomas had never seen a boy over five in a dress once he had been breeched. As he had been out of dresses for nearly 10 years, he was horrified at the prospect of attending school dressed like a little boy, or worse, a girl.
"And now, what we have all been waiting for!" Samantha announced eagerly. "I give you, Thomas Wright's privates, exposed for all."
Thomas wriggled and squirmed, but the girls held him down firmly. He could neither get free nor roll over to obscure his shame. Samantha held a lantern closer to his crotch so as to give the other girls a clear view. "Little Thomas certainly is small, is it not?" she asked.
Mary handed a cloth measuring tape to Samantha. "I took it from Mama's sewing box. Can we do it now?"
Samantha nodded. Taking care not to let her fingers touch the boy's penis, she cautiously stretched out the tape from its tip to its base. "Three inches!" she exclaimed.
"Is that big or small for a boy?" Mary asked.
Thomas cringed. He could not believe that every girl he knew was examining and discussing his penis.
"Very small, I would say," Sarah replied. "Our brother is the same age and when he steps from his bath it hangs at least five inches!"
Margaret smiled. "True, but I have caught him several times when he thought he was alone and he made it even bigger!"
"How did he do that?" Samantha asked.
"It is so easy, even you can do it," Margaret replied. "Just touch his privates and watch what happens."
Cautiously, Samantha reached out and her fingers touched the tip of the restrained boy's penis. In seconds, it throbbed and grew thicker and longer. The girls gasped and Samantha pulled her hand back.
Margaret laughed, and told the younger girl, "You can make it even bigger and harder if you stroke it. But I should warn you; if you do, he will likely loose control and expel a creamy fluid. When my brother realized I had seen him do that, for weeks he was too embarrassed to say a word to me, or even look me in the eye."
Samantha flashed a wicked smile. "So if I made a boy do that in front of all the girls in school, he would be too humiliated to face them?" She turned to Thomas. "I think all of us girls would like to see that! You would not be humiliated if I tried that, would you, Master Thomas?"
A terrified expression crossed Thomas' face. "You would not really do that, would you, Samantha?"
"Why not?" Samantha asked. "You humiliated me in front of your friend, did you not?"
"Please, Samantha!" Thomas pleaded. "I beg you, do not do it! I apologize for what I did at the schoolhouse. I swear, I shall never do it again."
"I think he will enjoy it," Margaret said. "My brother did-- until he realized he was being watched."
Samantha laughed and grasped his penis. She stroked it slowly, exposing the foreskin. As the air hit Thomas' exposed glans, his penis grew stiffer and he began panting. "Am I making him pant like dog?" Samantha asked.
Margaret nodded. "He may feel most shamed, but if he is like my brother he will be enjoying it so much that he will not want you to stop. My brother could not bring himself to stop, even when he saw me watching, until he had expelled the fluid."
Samantha was thrilled with her newfound power. "See, Master Thomas? With just my small hand I can make you pant like a dog or..." She released her grasp and pulled her hand away.
"No!" Thomas cried. "For the love of God, pray continue! I beg you, do not stop!"
"Hand me the measure again, Mary," Samantha said. She took the tape and remeasured his penis. "Five and a half inches!" she announced. The girls gasped. The restrained boy's unrestrained, rock-hard penis careened back and forth, as helpless as he was. "I shall continue if you swear to beg me later for a whipping, for I would whip you as you spanked me, and you did make me ask for my spanking."
"Whatever you say; just pray continue," Thomas begged.
Samantha laughed and resumed stroking his penis. She enjoyed being in control of the older boy. Finally, he jerked and shot several jets of creamy fluid from his penis. The girls gasped and giggled at the display and Thomas' horniness subsided, to be replaced by mortification.
He closed his eyes. "I am so ashamed. It would be horrible enough were a single girl to witness this, but to be seen by every girl I know is more than I can bear!"
Samantha laughed gleeful, savoring both her revenge and the fact that it was only beginning. "Margaret, it is time for you and Sarah to shave Master Thomas like a babe."
Margaret took out the strop and sharpened the razor. Sarah prepared shaving soap, mixing it in the shaving bowl. Sarah grasped the brush and applied the soap lather to Thomas' pubic hair. Margaret held up the sharp straight-edge, which glistened in the night. Thomas' eyes grew wide and he was too frightened to cry out.
"Wait!" Samantha called out. "He is much smaller now. He is only three inches again. Perhaps you should cut that little thing off as well, so it will no longer be an embarrassment to him."
Thomas was terrified. "No!" he cried.
Samantha laughed. "If that is your wish, Master Thomas, them you had best let your wish to have only your hair sliced off be made clear. Beg Margaret, in front of all of these witnesses, to shave off all your hair and to leave that stump of potential manhood, so that we may take pleasure in its unusual smallness."
Thomas' eyes were glued to the blade of the straight-edge. He knew he had no choice but to humiliate himself further. "Please, Margaret, I beg you in front of all of these witnesses, to shave off each of my short and curly hairs, but to leave this stump of potential manhood, so that each and every girl present may take pleasure in its unusual smallness."
The girls laughed loudly, as Margaret held up the sharp straight-edge and shaved off Thomas' pubic hair. "Bald as a newborn babe, just as you requested," she said to Samantha.
Samantha ran her hand over Thomas' smooth pubic region, embarrassing the boy even further. "As I suspected, you are a very little boy, Master Thomas. Tie him to the post."
Jane, Sally, and Sophie dragged Thomas to a wooden post and tied his wrists above his head to it with leather bridle straps. The naked boy's nose pressed against the post as he heard the girls gather behind him. Samantha circled around, coming within his range of vision. She carried a leather strap.
"You swore to beg me for your whipping," Samantha said. "You would not break a sworn oath, would you?"
"You know I would never break a sworn oath," Thomas replied.
Samantha smiled. "Then beg, boy! Beg for your whipping."
Thomas shut his eyes. "I beg you, Samantha Warren — give me a proper whipping."
"A proper whipping?" Samantha repeated. She brought the lash down upon his back, causing him to yelp. "I doubt your back could stand 50 lashes." She whipped his thigh and Thomas cried out in pain. "Your skin is far too sensitive. Better that you should beg for only your buttocks to be whipped." Samantha whipped his thigh again and Thomas screamed.
"Please, please, whip only my buttocks!" he cried.
"Repeat after me, then," Samantha said. "I have been a naughty boy. Please whip my ass until it is red and raw and I am crying like a newborn babe."
Thomas had no intention of crying in front of all of the girls in his class, but he knew he could not bear more lashes to his back or thigh. At least his buttocks was well padded, he thought. He steeled himself and repeated, "I have been a naughty boy. Please whip my ass until it is red and raw and I am crying like a newborn babe."
The girls laughed and cheered. Thomas jerked as Samantha lashed his butt. "Let us see how many lashes it takes to turn him into a bawling babe," Samantha said. Thomas swore to himself that he would not let a single tear roll down his face. He would not even give them the satisfaction of crying out.
The leather ripped into his butt. Thomas bit his lip.
Thomas squeezed his buttocks tight, shut his eyes, and prayed or his ordeal to end soon.
Thomas let out an involuntary yelp, which delighted his audience. Samantha paused to watch the six welts redden on the boy's buttocks. "Are you enjoying your flogging, Master Thomas?" she asked.
Thomas stifled a sob.
Samantha ran the tip of her finger over the longest of the welts. "Soon, your buttocks shall be naught but a patchwork of such marks. Cry your eyes out and spare yourself the rod, or else beg me further."
Thomas remained resolute in his vow not to cry. He repeated, "I have been a naughty boy. Please whip my ass until it is red and raw and I am crying like a newborn babe."
"Allow me a turn." Sally Folger said, taking the leather strap from Samantha. "I shall give him a good trouncing," The 14-year-old, being one of the oldest girls was also one of the strongest. She brought the lash down forcefully upon Thomas' ass. The boy yelped and shouted, as a dozen more red marks joined those already on his backside.
Sally handed the strap to her younger sister Sophie. "I shall give you a dozen lashes as well, Thomas Wright. You shall soon enough be moved to tears." Sophie began whipping the bound boy.
"Please!" Thomas cried. "Have mercy!"
"Mercy?" Sophie asked. "You have not even shed your first tear! Wait until your buttocks is on fire and you have cried until you have no tears left within you, and then beg for mercy." She flogged him again.
Thomas' ass was covered with crisscrossed red welts. "Those must be painful," Kate Morgan said.
Sophie finished her portion of the flogging and offered Kate the strap. "Maybe you can do better and bring tears to his eyes."
The 11-year-old grinned. "I do not mind if you beg me for mercy, Thomas Wright. You shan't receive any, but I shall enjoy listening to your pleas nonetheless." She gave him half a dozen lashes, as did 12-year-old Elizabeth Brennan. Elizabeth turned the strap over to her sister, Mary.
Mary leaned over and whispered into Thomas's ear. "I know you are holding back, desperate to cry. You think that as you have endured floggings by the oldest girls that you will easily endure a whipping from a weak 10-year-old like me. But know this, Thomas Wright: I shall give you 12 lashes. The first six will be to your buttock and they shall be less powerfully delivered than those you have already received. But I shall aim lower for the last six. Should you not release the tears and cries you've pent up so well, I shall flog your testicles as they dangle helplessly, and claim my aim was off."
Thomas was terrified. He wished he had cried when Samantha first whipped him. Now, he faced a choice of mortification from being seen breaking down in tears under the hand of a 10-year-old little girl or having his balls lashed repeatedly with the leather strap. He pulled on the leather bridle straps that bound him to the post, but they were tied too tightly.
The force of the blow was half that of most of the others he had received. Thomas knew he could handle five more like it without crying. It was the promised seventh blow that he feared.
Thomas took a deep breath and awaited the lash. He did not have long to wait.
"Owww!" he screamed. The lash cut across his balls, bringing indescribable pain. "God have mercy!" he cried. "Thomas knew he could not bear another such blow, let alone five like it. He had desperately wanted to break down, and this was his opportunity. "No more! No more!" he screamed, bursting into loud sobs. Tears streamed down his face.
"Well done, Mary," Samantha said. She approached Thomas and cupped the crying boy's chin in her hand. "How does it feel to be reduced to tears by a 10-year-old, Master Thomas? To have your buttocks whipped red and raw and to be crying like a newborn babe before every girl in school?"
Thomas continued crying. He found that once he had released the floodgate of tears, he could not stop. "No more! Please, I beg you!"
Samantha grinned like a cat that had cornered a mouse. "As you wish, Master Thomas. But if you are bald as a babe, and bawling like a babe, then you must dress as one as well." She cut him down and handed the naked boy a diaper. "You shall wear this swaddling cloth beneath your dress."
The sobbing boy accepted the diaper without a word.
"Lie on the floor and Sarah and Margaret shall diaper you," Samantha ordered.
Thomas obeyed, lying down at her feet. Sarah and Margaret rushed to attach the diaper. Thomas was mortified at the thought that the girl he had hoped to impress was now diapering him. When they had finished, Thomas sat up and Samantha handed him a bottle.
"What's this?" he asked.
"Cod liver oil," she replied. "Drink it."
Thomas thought about refusing but, after glancing at the determined faces surrounding him, thought better of it and swallowed the foul liquid. The girls laughed at the faces he made as he drained the bottle.
Sarah Carter tugged on his diaper. "We have each wagered on what hour of the school day you will need this changed. My brother swallowed half as much cod liver oil and he could not hold it in for more than two hours!"
Samantha handed Thomas a dress. "Sarah tells us that you came here this morn seeking to get into Margaret's dress. Indeed you shall, but not the way you had intended."
The girls laughed as Thomas took the dress. "What have you done with my clothes?"
"We buried them where you shall not discover them," Jane Holter replied. "Of course, if you would rather walk to the schoolhouse in just a diaper, I am sure none of us will object."
"I would instead go home and change into my school clothes," Thomas replied.
"And how would you explain your current state of dress?" Sally Folger asked. "Do what we say and after school we will tell you where to find your buried clothes."
"I cannot go to school like this! The teacher will—"
"Miss Fletcher will read this note from your mother, which I have written in her hand," Samantha said. "It explains that you have a stomach ailment that has caused you to soil all of your britches and that is why you must wear a diaper and a handed down dress to school."
Thomas cringed as he realized the girls were actually going to go through with their plan.
"The letter also explains that, as you have grown up without sisters, your mother fears that you have become entirely too modest about your body. She asks that, in the event you soil yourself whilst at school, the teacher ask for volunteers from your female classmates to assist in changing your diaper."
Thomas gasped. "You mean two of you will take me out to the school yard and change my diaper if the cod liver oil causes me to soil it?"
Samantha smiled fiendishly. "Oh, no, Master Thomas! We would never do that in the school yard where the entire class could watch from the window."
Thomas breathed a sigh of relief. "Where then? Behind the bushes?"
"Why, Master Thomas!" Samantha exclaimed. "Can you not guess? Did I not promise to see you stripped and whipped?"
Thomas nodded. "And so you have, Samantha Warren. You have kept your word,"
"And did I not swear that I would not rest until every boy and girl in school has seen you sprawled across Miss Fletcher's desk, naked as the day you were born?" Samantha asked.
Her words sunk in to Thomas. "Across Miss Fletcher's desk? You plan to change my diaper on the teacher's desk?"
"Recall that I swore an oath to thoroughly humiliate you, Thomas Wright!" Samantha replied. "We shall escort you to the schoolhouse, so do not think you may flee. Every boy at school will see you arrive in a Margaret's pretty dress. I am sure they shall snicker at your 'problem' and wonder if you shall also soil yourself at school." She tapped the empty cod liver oil bottle. "Of course, we know you shall. And then, as I swore, every boy and girl in school shall see you sprawled across Miss Fletcher's desk, naked as the day you were born!"
"Please!" Thomas pleaded. He pictured himself lying nude atop Miss Fletcher's desk, exposed for all to see. As if that were not bad enough, his buttock would no doubt be soiled and his classmates would watch as one of the girls standing before him cleaned him like a baby. "Allow me some dignity!"
Samantha laughed. "Did you allow me any dignity, Thomas Wright, when you exposed the bare flesh of my buttock to your friend? Did you allow me any dignity when you made me beg for a spanking, or when you spanked my bare bottom in James' presence? And what thought had you of dignity when you placed your finger inside me, again, in front of James, so as to make me moan and behave in a most undignified manner?"
Thomas gazed at the ground. Thomas glanced into the faces surrounding him: 13-year-old Jane Holter, 14-year-old Sally Folger, 13-year-old Sophie Folger, 12-year-old Elizabeth Brennan, 10-year-old Mary Brennan, 11-year-old Kate Morgan, and the Carter sisters, 13-year-old Sarah and 15-year-old Margaret. He glanced back at Samantha Warren. He realized he would receive neither mercy nor reprieve from his captors. In 30 minutes, he would step into the schoolhouse and the most mortifying experience of his life would be permanently etched in the minds of every boy and girl he knew!