Underpants Memoirs

Stories about boys ending up in compromising situations, preferably naked and embarrassed, as the name suggests.
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Blondie
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Underpants Memoirs

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The following is applicable to all chapters of “Underpants Memoirs:”

© September 2019 by Blondie

This is a work of fiction and is fantasy only. Names, characters, places, and incidents are products of the author's imagination and are used fictitiously. Any resemblance to actual events or locales or persons, living or dead, is entirely coincidental.

For ages 18 and older only.

Chapter 1: Introduction to Roosevelt High
Chapter 2: First Tighty-Whities Sighting
Chapter 3: The Traditional Walk of Shame, Part 1
Chapter 4: The Traditional Walk of Shame, Part 2
Chapter 5: The Humiliation of Trudy Pennyfeather, Part 1 (ENF)
Chapter 6: The Humiliation of Trudy Pennyfeather, Part 2 (ENF)
Chapter 7: The Tighty-Whities Twins, Part 1
Chapter 8: The Tighty-Whities Twins, Part 2
Chapter 9: The Misadventures of Blondie

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Chapter 1: Introduction to Roosevelt High

Hi, my name is Michelle, and I graduated from Roosevelt High School a few years ago. I'm telling you this because Roosevelt High was (and probably still is) a school like no other. I know every school has their share of the occasional hazings and bullying, and that the older kids sometimes pick on the incoming freshmen. But at Roosevelt it was taken to a whole different level.

Make that a whole different stratosphere. It seemed like at least once a week—and sometimes more—some poor kid was having some (and sometimes all!) of their clothing forcibly removed, much to their extreme embarrassment. I have to say that the amount of strippings and humiliations that took take place during my four years there were mind-boggling.

Don't get me wrong—I absolutely loved being part of that culture. One never knew when the next sighting of a frantic freshman fighting to keep his clothes on would arise. And when it did, I must admit that I found it quite titillating, as it seemingly was for most of my fellow students. And to this day I derive considerable pleasure when I reflect on the sordid events that took place during my time in the hallowed halls of Roosevelt High. Which is why I'm writing these memoirs. I think it will be enjoyable to chronicle some of the various depantsings and humiliations that I either participated in, witnessed, or heard about during my four years in high school.

The ability to recount these events recently became more doable, as a few months ago I attended our 5-year reunion. Inevitably—and it didn't take long—the conversation revolved around the many accounts of the assorted humiliations that took place while we were there. In fact, it is fair to say that most of my time that night was joyously spent relating and listening to all the stories, most of which were told in detail. Some of them I had witnessed, but there were many that I had not been aware of, so it was a very stimulating evening for me, to say the least.

At some point early on I got the bright idea that it might be an interesting endeavor to pass along the accounts of some of these events in the form of a memoir. So I actually started writing down some of the specifics as they were detailed. I have a pretty good memory, but while writing this I'll probably refer to the notes that I jotted down on several cocktail napkins. These notes (and the detail that the narrators went into) should enable me to tell the tales in storybook fashion, which hopefully will be enjoyable for the reader—and for me. :D

Before I close this intro and move on to a stripping tale, I feel I should touch on the fact that there was little intervention—if any—by the adults in the room. Early in my freshman year when I witnessed a boy being depantsed, I was absolutely astounded when I watched three different teachers turn the other way while the strippings were transpiring. I later found out why.

Legend has it that the year before a bunch of seniors stripped a freshman boy completely naked, then made him walk the length of the football field. (I'm sorry I missed that one!) A female teacher reported the incident to the principal, so he felt obligated to act on it. After an investigation, some boys were suspended, and the main instigator was expelled.

About a week later the teacher was working late in her classroom and those same boys entered the room, held her down and stripped her naked. They tied her up with her arms above her head and took pictures. They told her she better not divulge their names, or they would release the pictures, and that they knew where she lived. They left her tied up there with the door open, and at some point a couple of students rescued her. Word got out to the rest of the faculty about her stripping. The teacher never gave up the names, but everyone knew who did it and why they did it.

For good measure, that same day they stalked the principal, a smallish man by the name of Jerry Radcliffe. As he was getting out of his car in front of his house they grabbed him and threw him in the back seat of their car. About two hours later they let him out of the car a couple of blocks from his house. He was stark naked, and only he and the perps know exactly what they did to him (or made him do).

In any case, the expelled student was reinstated the next day, and from that day forward the faculty members turned a blind eye to the humiliations that were doled out over my four years at Roosevelt High.

And, of course, no student would dare report these incidents to any authorities, as they are fearful (and rightfully so) of very humiliating consequences.

Oh, and there is one more matter to weigh in on before closing. You may be wondering why I have entitled these accounts "Underpants Memoirs." After all, out of all the depantsings that I'm aware of, I'd say almost half of them resulted in the victim being stripped completely naked. That was always a turn-on for me, but I must admit that I have a soft spot—a fascination may be a better way to put it—for watching a poor, frenzied freshman getting stripped down to his tighty-whities. For whatever reason, the choice of underwear for the smaller freshmen were almost always (much to my stimulation) the small white briefs, or more popularly known as tighty-whities, which will be the term of choice in these memoirs.

And, by the way, the victim of these strippings invariably was a freshman. I guess it was easier to pick on the smaller kids. Over the years the only exception I saw was this kid that went by the name of Blondie. He graduated the same year that I did, and I witnessed him being stripped right up to his senior year. And to make it even more embarrassing for him, it was his sister and her friends that were antagonizing him during his first three years there. Most boy strippings at Roosevelt were carried out by other boys, but that wasn't the case with this Blondie guy. Then, there was a girl named Felicity who must have really had something over on him. During his senior year she made him keep his body completely hairless and he had to wear these short shorts to school. It must have been really embarrassing for him to have to show off his clean-shaven legs like that to the whole school every day. Oh, and Felicity was a freshman at the time. Can you believe it?

Anyway, I'll have to use at least one of my chapters to tell you about one or more of Blondie's strippings that I happened to witness. He had a smaller than average size penis, and without the hair it looked like a freshman's dick (or maybe more like an elementary school kid's dick), and the sight of it made me giggle. And this Felicity girl really had a knack for ratcheting up his humiliation. I remember, much to my entertainment, him being stripped to his tighty-whities right at his locker. I guess at some point Felicity had other ideas, because one day I saw her make him drop his pants in the courtyard, and the poor boy was wearing a pair of panties—which, in conjunction with his hairless legs made him look quite feminine, indeed. I got a pretty good laugh out of that, not to mention a bit of a sexual arousal over his humiliation.

Speaking of panties, you've probably noticed that I did include a picture of a pair of panties on the cover of these memoirs. That's because, though probably over 90% of the strippings were administered to a boy, there was the occasional stripping of a female. In those cases, she usually wasn't stripped naked (though I know of two occasions when she was), but was stripped to her bra and panties, or on occasion, all the way down to her panties.

But I don't want to give too much away so early. I hope you'll stay tuned for my future chapters, which I'll add here as time permits.
Last edited by Blondie on Sat Sep 21, 2024 12:02 am, edited 1 time in total.
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Underpants Memoirs, Chapter 2

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Chapter 2: First Tighty-Whities Sighting

It didn't take long for me to realize that I was attending a school like no other.

It was during our second week of classes in my freshman year. I was walking across the courtyard during recess, on my way to the cafeteria. I had just enough time to grab a snack from the vending machine and munch it down before my next class. My progress was interrupted when I heard a bit of a commotion over by the Roosevelt statue.

"No! Please stop! No!" shrieked somebody in a high-pitched squeal.

I looked over and there were several students gathered around the area where the squeal came from. My curiosity was piqued, so I strode over there to see what the ruckus was all about. When I got there, though I was hungry, my snack became the furthest thing from my mind. The activity transpiring in the courtyard would prove to be much more stimulating.

On the grassy area below the statue there were five students on the ground. Above them was a student who had climbed the large statue and was standing on Roosevelt's outstretched arm, balancing himself with a hand on the neck. Of the five students on the ground, four of them were considerably bigger and heavier than the other—which was unfortunate for the smaller kid, because he was flat on his back, being pinned down by the stronger four. Though he was struggling mightily, I could see he would be no match for his aggressors, and that they would be free to have their way with the unlucky freshman.

I was a little naive at the time, and I hadn't yet heard all the stories of Roosevelt's history. With his arms pinned way above his head, I remember thinking that they were just going to tickle him. I know, that sounds laughable in retrospect.

I first realized that this would be more than a tickle attack when his tennis shoes were yanked off and thrown off to the side. Then they went for his socks. "No! No! Please stop!" he cried out again. He was kicking his legs frantically, but in short order his socks were pulled inside out off of his feet and thrown in two different directions.

I couldn't explain why, but I remember thinking at the time that, though I genuinely felt sorry for the kid, I was quite titillated by the forced removal of clothing (even though it was only a pair of shoes and socks!) and was dearly hoping that his antagonists would not stop there. Admittedly my prurient interests to see him stripped far surpassed any compassion I may have had for him.

My hopes would not be denied. It appeared that the barefoot boy was about to be rendered shirtless. I felt a tingling inside—I think I trembled a little bit—when they pulled his tee shirt from his jeans and exposed his pale, flat belly. The unmasking of skin—and the now likely possibility for more—was a thrilling prelude to what was to come.

I think the boy must have had an inkling at that point that his attackers had more in mind, and that his shirt might not be the last item of his clothing to be removed, because as they lifted his shirt up his torso his feverish struggles rose to another level. Somehow his frenzied flapping and flailing about added extra excitement to the whole affair. I glanced at a few of the faces of the spectators (the number of which had grown and was ever increasing), and their expressions probably mimicked mine—wide-eyed and open-mouthed, brimming with anticipation.

The freshman was putty in the older boys' hands, and they pulled his shirt over his head and off his outstretched arms with ease. The shirt was then tossed to the guy on the statue, who reached up and pulled it over the head of the marble figure.

Apparently I wasn't too far off with the tickling thing, because I guess one of the guys couldn't resist, and he used both hands to tickle the boy's now exposed, hairless underarms, causing the gyrations of the beleaguered lad to increase all the more. He wasn't laughing—his anguish was much too severe for that—but I did hear a few giggles emanating from the gathering.

This line of attack was short-lived, as they had bigger fish to fry. I felt my breath quickening when (as I had hoped!) a pair of hands began undoing the boy's belt buckle. "No! Oh shit! Oh God! No! Please!" he begged, but of course his desperate pleas would be in vain. As he continued to thrash about, one of the assailants—rather calmly, I might add—proceeded to finish undoing the belt, unfasten his jeans and pull down his zipper. He then methodically loosened and opened up his pants, affording every one of us our first glimpse of his white underpants. He then unhurriedly, bit by bit, started pulling his jeans down, gradually exposing his underpants entirely, along with a good portion of his thighs, much to the mortification of the crimson-faced, panicking boy.

I think that was the first sign for me that I had a predilection (fetish?) for seeing a boy's tighty-whities forcibly exposed, because the feeling of sexual arousal that swept through my body at that point was breathtaking. I was already looking forward to going home that day, locking myself in my room and gratifying myself, knowing that what I had witnessed so far would provide more than enough stimulus.

But there would be more. After pausing momentarily to take in the scene, the upper classman hauled the boy's jeans all the way down his relatively hairless legs until they were scrunched up at his ankles. For a moment he stopped, and it looked like that would be the end of it, but moments later, with the help of his cohorts, they swiftly pulled the pants inside out and off the feet of the maniacally kicking and screaming youth. Several students in the crowd cheered the lad's indignity while the jeans were tossed to the awaiting outstretched arm of the guy on the statue, who proceeded to wrap the pant legs around the neck of the Roosevelt figure and meticulously tie them in a double knot.

They held him there spread-eagled for a spell while, to my utmost enjoyment I took in for the first time the sight of a boy stripped down to his tighty-whities against his will, and it was a sight to behold. I ogled him from top to bottom for a few seconds before zeroing in on his little underpants. I could see the bulge at his crotch, and it looked like he had a good-sized penis, which I found surprising, considering his size. I was hoping that at some point they would strip off his underpants so I could see it (and because then he'd be naked and his humiliation would have been off the charts), but that didn't happen. Which was only slightly disappointing for me, because I thoroughly enjoyed leering at the scantily clad, humiliated boy in his tighty-whities.

He stopped flailing around so much after they took his pants off. I don't know, he was probably extremely anxious about the prospect of getting stripped naked. Maybe he figured if he stopped fighting they would leave him alone. And maybe it worked, because just like that, they let him go.

The next sequence was probably as enjoyable as the stripping itself. The boy's highest priority was to rescue his clothes. To achieve that, he would have to navigate the statue in his underpants. I'm sure you can picture the scene in your head vividly, and I'm here to tell you that it was as entertaining and stimulating as you might imagine. I watched gleefully as he rose from the ground and sprinted to the statue, his cute little tighty-whities clad tushy shaking about with every step. Several phones (including mine) were capturing the scene with video.

I mentioned that the Roosevelt statue is large. Plus, it is set on a pedestal, so it stands tall over the courtyard. Too tall, it turned out, for the most unfortunate, near-naked boy. He was hoping to grab onto the outstretched arm and hoist himself up—I'm sure that's how the upperclassman handled it—but no matter how hard he tried, he fell inches short. It was quite a comical sight as he futilely jumped up and down several times, only to come away empty handed.

I continued to laugh out loud as I watched him shimmy up the statue. With considerable effort, he finally managed to prop himself up on the arm. It took him all of about two minutes, but he was able to untie the tight knot and retrieve his jeans. They were still inside out, and he had to balance himself with one arm, so he had a difficult time remedying the issue. Eventually achieving that, he thought he would finally get relief and rectify his state of undress, but he found it impossible to balance himself on the arm and put his jeans on at the same time. I was thinking he should have sat down on the arm and pulled them up, but in his state of distress I'm sure he wasn't thinking very clearly. In any case, he finally gave up and tossed his jeans to the ground, eliciting more laughter from the gathering below him. He pulled his shirt inside out over the head of the statue—much like it was pulled over his own head a few minutes earlier—and instead of trying to put it on, he immediately dropped it to the ground.

The entertainment continued as I watched him wrap his bare legs around the statue's torso and shimmy his way back down to the ground. As he dashed to his clothes I looked at his anguished expression and was taken aback at how red his face was. I had never seen anyone that embarrassed in my entire life—and no wonder!

As some of the crowd started to disperse, the poor boy grabbed his clothes and retreated to the other side of the statue, where he could dress himself away from all the prying eyes.

I turned and started making my way to my next class. I had run out of time to get my snack, but the tradeoff was oh, so worth it! I was still grinning and giggling to myself as I entered the building of the school like no other.
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Re: Underpants Memoirs

Post by Robert Brooks »

Yay! One of my absolute favourites of yours! :D
Really looking forward to seeing this series coming to gpns. Maybe even continue it…?
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Re: Underpants Memoirs, Chapter 3

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Chapter 3: The Traditional Walk of Shame, Part 1

It was a warm, pleasant afternoon in early autumn, about two weeks removed from the wonderful scene in the courtyard that I previously described. I was sitting under the sun in the stands overlooking the football field along with a couple of my friends during lunch hour. Three rows in front of us, in the first row, there was a lone freshman staring at his phone while nonchalantly nibbling on his lunch. He was a cute boy with a slight frame, and he didn't look a day over 12. As I would discover early on, he was just the type that often was preyed on by the fiendish predators roaming the grounds of Roosevelt High.

The boy was taking a bite from his tuna fish sandwich when four burly guys approached him. They were probably seniors, but could have been juniors. It didn't really matter, though. It was readily apparent they were up to no good, and the freshman would be no match for whatever dirty deed they had in mind.

Two of the bullies sat on either side of the unsuspecting frosh, while the other two sat directly in front of him. I had a perfect view of the proceedings and was close enough to hear the dialogue. "How's it going?" said the guy on his left. "My name's Victor. What's yours?"

The freshman looked at him, then took in his immediate surroundings, and was rapidly becoming a bit uncomfortable. "Harvey," he answered while glancing at Victor apprehensively.

"Hi, Harvey, nice to meet you," said Victor. "This is Brent," he said while pointing at the figure on Harvey's right, who was smiling menacingly. "Up here is Frank and Lenny." Harvey remained quiet. It was clear he knew something was up, and he had no interest in pleasantries. "We just wanted to welcome you to Roosevelt High," continued Victor.

"Th-thanks," replied Harvey.

The three of us were looking on in fascination. There was a sense that something very interesting was about to go down, though at the time I wasn't sure what it was. Would it be another stripping? A strong part of me was hoping so. I looked around and noticed that most of the other students in the general area were also looking on intently. At least 75% of them were female. I learned later that when a boy was to be stripped the guys doing the deed made a point to make sure there were female witnesses, knowing their victim will be that much more humiliated.

Meanwhile, Harvey sensed that it would be in his best interests to vacate the premises as quickly as possible. He made a move to get up but was immediately returned to his seat by a forceful hand pushing on his shoulder. "Don't go," said Victor. "We just want to get acquainted. Plus, we have a tradition here at Roosevelt. It's a special way we like to welcome a nice young freshman like yourself." Harvey didn't respond. I'm sure he didn't want to be involved in whatever tradition his antagonist had in mind. As for me, I was becoming increasingly intrigued as to where this was going.

"I wonder what kind of underpants he's wearing," asked the guy identified as Lenny.

I immediately felt a wave of delicious anticipation. Giggling, I grabbed the arm of one of my friends and whispered, "I have a funny feeling we're going to find out."

"I don't know," answered Victor. "Let's ask him. What kind of underpants are you wearing, Harvey?" Harvey was not at all interested in the direction the conversation was going, and he chose not to respond. His silence would not help his cause. "I guess we'll have to just see for ourselves," said Victor as he reached behind Harvey's back and delved his hand inside the back of his dark brown corduroys. The rattled Harvey reached back to try to stop the intrusion, but he was too late, as Victor had managed to pull Harvey's underpants up past the small of his back, revealing a striped waistband and a fair amount of the material below it.

"Tighty-whities," called out the guy on Harvey's right, and I was becoming more enthralled by the second.

"Perfect," said Victor with a smile. "We found our boy."

Again the beleaguered boy tried to extricate himself from his increasingly adverse predicament, but was thwarted by two of the upper classmen. It was clear he wasn't going anywhere until his antagonists were finished with him. "Just relax, Harvey," said Victor while putting a hand on his shoulder. "If you do what we tell you to do, it will be a lot easier for you."

"Please," begged Harvey. "Just let me go."

"We will," answered Victor. "But you have to do something for us first."

Harvey was momentarily silent. I'm sure he was frightened and was desperately trying to figure a way out. He probably realized there was none, other than compliance. "What....what do you want me to do?" he asked apprehensively.

"Now you're talking," said Victor. "So, as I said, we have a tradition. A tradition like no other. Every September a freshman—and it's your lucky day, because this year it's going to be you—every September a freshman has to walk up and down these stands in his tighty-whities."

My eyes widened and my jaw dropped at the declaration. I couldn't see Harvey's face, but I'm pretty sure he had the same reaction. Of course, the difference was that he was in a state of panic, and I was becoming ever more titillated.

"No, please, I....I can't....please, I can't do that."

Harvey, for the first time, turned around and looked warily at the students behind him. I'm sure he was unnerved to see about twenty or so of us scattered about, looking on with keen interest. The three of us were the closest to him, and he and I made eye contact, much to my delight. I'm sure the smile on my face did nothing to assuage his heightened state of anxiety.

"That's what the guy said last year," retorted Victor. "But he eventually did the tighty-whities walk of shame, starting right where you are right now. And so will you." One of the guys in front of Harvey reached down to untie one of Harvey's shoelaces, and he quickly pulled his foot away. "If you try to fight us, it'll only make it worse for you," warned Victor. Harvey again glanced anxiously behind him. The look on his face was one of a frightened schoolboy.

The same guy reached down again to Harvey's shoe, and Harvey kicked his hand away. "All right, that's it. I told you not to fight us," said Victor, and he jumped up and grabbed Harvey from behind. He had him in a bear hug, arms pinned to his sides. He then lifted his feet off the ground. "Pull his pants down," directed Victor.

"No! No!" screamed Harvey, his legs kicking wildly. But Harvey was easy prey for the four bullies. While two of them took hold of his legs, the other reached for his midsection. Harvey wasn't wearing a belt, so one of the guys simply unsnapped his corduroys, pulled down his zipper, and hauled his trousers all the way down his legs. His shirt was scrunched up his belly due to Victor's hold on him, so his tighty-whities were on full display, much to my pleasure. I glanced at my two friends, and they were clearly enjoying the scene, also.

Victor set the boy back down in his seat, and Harvey immediately reached down in hopes of pulling up his pants. Victor grabbed him by the biceps and held him back. "I wouldn't do that if I were you," said Victor. "Unless you want to be naked."

Upon hearing that, I dearly hoped he would continue fighting back. But I'm sure the prospect of getting stripped naked out there horrified him, and I'm also sure that he was readily aware that if they were provoked, then he would be helpless to stop them from doing just that.

Harvey grudgingly sat back up. Sort of. He was still leaning forward with his arms crossed over his thighs. "Sit up straight," commanded Victor. Harvey grudgingly and deliberately did so. "Hands on the bench," ordered Victor.

"Please, just.....just let me go," said Harvey, but he succumbed and laid his hands flat on the bench on either side of him.

"We will, Harvey, we will," responded Victor. "After the traditional walk." While Victor was speaking the two guys in front of Harold were busy untying and removing his shoes. In short order they took hold of his socks and pulled them off. They continued to hold onto his bare ankles, resting his feet on their laps. Harvey made a half-hearted attempt to pull his legs away, but they maintained their grip.

I really enjoyed the next scene. It happened very quickly, but I can picture it in my mind vividly today, almost as if I am seeing it in slow motion. Victor reached over and took the hem of Harvey's shirt with both hands and began lifting it up. "Hold your arms up," said Victor. Harvey hesitated, and Victor was relentless. "Do it!" he said, loudly and forcefully.

"No! Please don't!" yelled Harold as he raised his arms in the air. His cries of anguish were prompted partially by the hoisting of his shirt up his torso. But there was another development that unquestionably had a greater effect on his elevated level of distress. Though he probably couldn't see it because it coincided with his rising shirt covering his eyes, he certainly had become aware that his pants were being tugged across his feet, and in a rather brisk manner. The timing of the two articles of clothing being removed was exquisite. Just as his shirt was being pulled from his fingertips, Harvey was afforded the discomfiting view of the last thread of his corduroys escaping from his feet.

"Oh, my goodness!" exclaimed one of my friends.

In about the amount of time it would take one to utter the words "stripped and humiliated," poor Harvey was rendered naked but for a little pair of tighty-whities.

To be continued....
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Underpants Memoirs, Chapter 4

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Chapter 4: The Traditional Walk of Shame, Part 2

"Oh no! Oh shit! Oh!" cried out the panicked Harvey when he realized he was expeditiously and simultaneously divested of his corduroys and his shirt and was out in public wearing only his underpants. Harvey wasn't the only one crying out. Cheers of amusement rang out from the twenty or so spectators in the football stands sitting behind him. I was one of them, and I remember giggling with excitement as I watched Harvey leaning down and squirming around in his seat, clad only in his tighty-whities.

"Sit up straight," said Victor while he pulled Harvey more upright by the shoulder. Harvey looked longingly at his pants and shirt, which were teasingly draped over the railing just a few feet in front of him.

"Can I please.....can I please get my clothes back?" begged Harvey, his voice quivering slightly.

"In due time, Harvey. In due time," answered Victor. "We have twenty minutes until lunch is over, so why don't you just relax and finish your sandwich." I almost choked on my saliva. Were they going to make him sit there and eat his lunch? In his underpants?

Harvey made no effort to even acknowledge the unusual request, so Victor picked up the half-eaten tuna fish sandwich and held it up to him. "Eat," said Victor. "You'll need your energy to walk the stands."

"I'm....I'm not hungry," responded Harvey boldly.

"Hold him up," said Victor to his buddies as he stood up. "I'll make him eat this sandwich after I stick it up his ass." His three companions also got up and two of them grabbed Harvey by the arms. I looked on wide-eyed while Harvey was held up and restrained. Victor pulled open the back of his underpants and it looked for all the world like he was going to shove the sandwich right up the crevice of Harvey's ass cheeks.

"No! Okay! I'll eat it!" screamed Harvey. "Stop, I'll eat it I said!"

Victor thought about carrying out the sordid deed, then thought better of it. He let Harvey sit back down, and indeed he slowly munched on his sandwich while sitting there in his tighty-whities. He had to know everyone was staring at him, and it was amusing for all of us, while at the same time a bit surreal. I swear, you never knew what to expect at that school.

"Would you like some water to wash that down?" asked Victor. Harvey shook his head quickly while staring down. I was wondering where Victor was going with this, and I would soon find out—to my delight. "You need to drink some water before your walk of shame. We wouldn't want you to get dehydrated." Victor then pointed to a drinking fountain just off to the right of the stands. "Go get some water."

I think at that point Harvey was resigned to the fact that he would not get his clothes back until he was done doing their bidding. He stared at the drinking fountain for a spell before building up the courage to stand up. It was a delicious sight for me as I watched him make his way to the drinking fountain in his tighty-whities. He had both hands over his crotch as he scampered past his clothes, took a quick drink of water from the fountain, and dashed back to the laughing group. I thought he might make a run for it, but first of all they would have caught him and made it worse for him, and secondly, I don't think he wanted to go anywhere without his clothes.

As I watched him running back I took in the miserable look on his very red face. It was about to get redder. "It's time, Harvey," said Victor as he took him by the arm and pulled him toward the aisle. Harvey reluctantly followed him, keeping his free hand covering the front of his underpants.

Speaking of his underpants, I mentioned that he had been rendered naked but for "a little pair of tighty-whities." Well, "little" is the operative word. I know that the white briefs are, well, pretty brief, but I don't think his mother had been underwear shopping for him in a while, because his were at least a size too small. The waist band was well below his belly button, and the leg openings of the back came up to the very bottom of his ass cheeks. I couldn't see the front because he was covering it up the whole time, but I was thinking it was probably pretty tight. I remember hoping to get a better look, and fortunately that would soon be the case. My heart started beating faster as Victor led Harvey to the middle of the aisle and let go of his arm. The terrified Harvey was facing toward the football field, bent over with both hands securely covering his groin. "Turn around," ordered Victor while nudging him on the shoulder. Slowly but surely, Harvey turned around and faced us. I mentioned that my heart was beating faster, but Harvey had me beat on that front. His chest was heaving in and out at a very rapid pace.

"Okay, here's how it works," started Victor. "You have to walk—don't run—to the top of the stands, touch the top rail, then turn around and walk back down. That's it. When you get back down we'll let you get your clothes. Got that?" Harvey nodded without looking up. "Good. I'll tell you when to start. Now stand up straight, no crouching. And put your hands on your head and leave them there. Show everyone your pits, and all of your tighty-whities. It's tradition."

My heart beat yet faster in anticipation, while my two friends giggled merrily. The beleaguered Harvey ever so slowly removed his hands from the front of his underpants and submissively raised them to his head. He was a sight to behold. I looked him up and down and didn't see a hair anywhere below his head. I remember wondering if he had any around his bits—and I was almost certain that he didn't.

Speaking of his bits, I looked closely and there wasn't much there. Indeed, his little underpants were pretty tight, but even with that I could barely discern the tip of his penis poking at the material. He was already as embarrassed as all get out. I doubt if knowing that everyone was looking at his negligible protuberance helped him feel any better. I couldn't suppress a giggle as I sized him up. He peeked up at me and quickly turned away, abashed. I really enjoyed the moment.

"Okay, get ready, Harvey, here we go!" yelled Victor, loud enough for all to hear. "Ladies and gentlemen, the traditionallllll, WALK OF SHAME!" he bellowed while giving Harvey a robust slap on his ass to start him off.

And start off he did. Much to the fascination of the onlookers—along with a dose of stimulation for me—the profusely blushing lad indeed made his walk of shame up the football stands in his tighty-whities. There was a boisterous reaction from the spectators throughout his mortifying journey, which only must have served to exacerbate his extreme embarrassment.

At one point on his way up, an entertained girl shouted out, "Can we see your little pee-pee?" That elicited a chorus of laughter, which seemed to cause Harvey to speed up his gait in hopes of ending his torment as soon as possible. In fact, on the way back down he picked up his pace to somewhat of a trot, a decision (though probably more of an involuntary reaction than a decision) that decidedly would not serve him well in the end.

"You went too fast," said the grinning Victor when Harvey returned. "You'll have to do it again and take it slow."

"Oh, please, just let me go!" pleaded Harvey breathlessly.

"After you do it again," insisted Victor. "It's a walk of shame, not a run of shame. Now turn around and put your hands on your head."

Once again, the agonized Harvey turned and faced us with his hands on his head. Only this time the "tradition" would take a turn for the worse for Harvey—and conversely, a turn for the better for me, and presumably everyone in attendance other than the harried victim. For, as Victor shouted out the command, "Go!" to Harvey, he simultaneously reached down and pulled his underpants swiftly to his knees. The astonished Harvey bent down and pulled them back up, posthaste. It happened so quickly that I hardly got a chance to see what Harvey desperately was trying to hide, though that did nothing to quell my laughter and excitement, nor apparently anyone else's that witnessed the ignominious deed.

"Oh, my goodness!" said one of my friends.

"Make him do it naked!" shouted a girl, and I suddenly realized that girl was me. I had impulsively vocalized what was on my mind.

"Michelle!" said my friend as she looked at me in surprise. "You little devil, you!" she said with a laugh.

"I know," I laughed. "I can't believe I said that." I paused for a moment. "But I hope he does it," I said as I leaned into my friend kittenishly. We both laughed as we looked on intently in hopeful anticipation.

Evidently I wasn't the only one who felt that way, because momentarily someone started a chant. "Na-ked! Na-ked!" Before you knew it, most of us had joined in. "Na-ked! Na-ked! Na-ked!"

Victor looked up at us and grinned, then turned back to his favorite freshman. He again reached for Harvey's underpants, but the frantic Harvey had a firm grip on them, holding on as if for dear life.

"Na-ked! Na-ked!" came the continuous chant. The atmosphere was electric.

"Let's do it!" said the energized Victor to his buddies, and they all swarmed on the terrified lad. Instead of holding him down, all four of them went straight for his underpants.

"No! No!" screamed Harvey as he slapped at them with his hands—for them it probably felt like a nuisance fly—and kicked his legs wildly like a trapped animal in an effort to fend them off. But his underpants were soon sliding down to his knees.

"Na-ked! Na-ked! Na-ked!"

"Stop!" Harvey continued kicking and screaming. It was quite a scene, and a very entertaining one at that. His undies were pulled down to his ankles, and Harvey was desperate. In a last-ditch effort to keep from forfeiting his precious underpants, he spread his legs out as far as he could to keep them from sliding off. He pulled his legs forward and grabbed onto the waist band and tried to pull them back up his legs. But he was unable to make much progress.

"Na-ked! Na-ked!"

Harvey was fighting a losing battle, but ever so valiantly. He held on to the waist band with both hands, but there were four sets of hands pulling in the other direction. It was a tug-of-war, and a distinctly uneven one. But Harvey's desperation must have given him added strength—desperation can make for a powerful weapon—because he was holding his own over his four combatants.

That is, until Victor got the bright idea to try a different line of attack. He let go of Harvey's underpants and instead focused on his bare torso. Digging his fingers into his ribcage, Victor tickled Harvey unmercifully until he inevitably relinquished his vice grip on his tighty-whities in order to dislodge the fingers that were poking into his sides ever so persistently. He was successful in that endeavor, but the tradeoff was decisively not in his favor, as he was quite unsuccessful with his main objective, which led to significant consequences.

In the end, the outcome was predictable. Much to his utter consternation and to my delectation, Harvey's underpants were in the possession of his aggressors. The moment they were slipped off his feet we stopped the na-ked chant and rejoiced, in unison, "NAKED!" Cheering and clapping broke out. It was quite the festive atmosphere.

In the immediate moments after the stripping, the unfortunate naked boy was beside himself, and reacted much like a fish out of water. The laughing foursome kept him at bay while he flailed about at the bottom of the aisle. Whenever he tried to make a run for his clothes—it had to be so tantalizing for him because they were only a few feet away—his efforts were easily thwarted.

After a bit Harvey finally settled down, and was on his knees, leaning completely over with his arms on the ground. He was facing sideways, so I couldn't see his privates or much of his bum, but I have to say I was deriving considerable pleasure from his naked shame. I can't explain why that is—it seems cruel and sadistic when you think about it, being that the poor kid was enduring the humiliation of a lifetime—but I can tell you unequivocally that I found the scene quite enjoyable. And looking around, I could tell that I was not alone in this regard. I guess this is a dark side of human nature, but it was one that I honestly had no interest in resisting. I was having way too much fun.

"You still have to do the walk of shame again," said Victor.

Harvey looked up, wide-eyed. "I can't....like this........can I do it....do it in....in my underpants again?" I chuckled, mainly at the absurdity that he was begging to do the walk of shame again in his tighty-whities. That clearly illustrated how terrified he was of the alternative.

"No, definitely not," replied Victor. "If the freshman has to do the walk of shame a second time, it always has to be naked. It's tradition." I had a pretty good inkling that Victor was making up this "tradition" on the fly. Not that I was complaining.

A few moments went by with nothing happening. Harvey seemed too overwhelmed to move, and Victor was content to let him sort it out. But not for much longer. "If you want to see your clothes again, Harvey, you'll have to do the walk. And I'm not going to wait much longer," said Victor.

"Please.....let me have my under.....ohhh......can I.....can I at least cover up with my hands?"

Oh, yes. He realizes he has no choice. He's really going to do it!

"No, I'm afraid not. Hands on your head during the walk of shame. It's tradition." Harvey was silent, and again there was a standstill. Victor was ready to move things along. "All right, you guys," he said while addressing his friends. "Gather all of Harvey's clothes and go hide them where he'll never find them."

"I got it," said one of them as he made a move toward the rail.

"No! Okay! I'll do it!" cried Harvey.

We all waited with bated breath as Harvey ever so slowly picked himself up off the deck. His hands remained securely clasped over his genitals. He was facing backward, affording us a delightful view of his naked bum. But of course, I wanted more.

"Turn around, Harvey. Come on, you can do this," encouraged Victor. "The sooner you get it over with, the sooner you can have your clothes back and put this all behind you."

Yeah, right, like he'll ever forget this. I don't think so.

Harvey turned around, ever so deliberately. He was quite the vision, all naked and red-faced with his hands clenched firmly over his goodies, as if exposing them to us would be his doom.

"Good, Harvey," continued Victor. "Now after you put your hands on your head I'll tell you when to start."

The tension had built to a crescendo. I think I was literally holding my breath. Most everyone had their phones held up in video mode. I did not, preferring to take it all in without the distraction, knowing I could obtain it later from one of my friends.

Harvey knew what he had to do, but it was an excruciating moment for him. His breaths were rapid as he shifted his weight from one foot to the other while calling on every fiber of his being to dig up the courage to do what he knew he had to do. He took a quick look up at the stands. I'm sure he noticed that most of the spectators had gathered closer to the aisle on both sides to achieve a better view of what promised to be an entertaining display for them. Once again, he and I made eye contact, and I smiled at him. It definitely added to the moment for me.

"It's time, Harvey," prodded Victor.

And so it was. With great effort, Harvey extricated his hands from his privates and raised them to his head. The uproar was raucous as all eyes immediately zeroed in on Harvey's genitalia. In case the reader is wondering—and I have a feeling you are—Harvey had a small penis, which, not surprisingly, was completely devoid of any hair. His testicles were proportionately small, and his nut sack was all shriveled up and only visible if scrutinized—and scrutinize I did. I'm not sure if his balls were always like that or if it was due to his overwhelming humiliation. Whatever, I can tell you that his little bits were a source of amusement for me, and most certainly were a source of extreme mortification for naked Harvey.

* * * * *

Before I finish describing Harvey's ordeal, please bear with me while I venture off course for a moment and discuss penises. During my four years at Roosevelt, I saw my share of penises—more than any teenage girl rightfully should. This is not because I was promiscuous—I was a virgin all the way through high school—but because of the many strippings that occurred at Roosevelt High School.

As I'm sure you know, penises come in many shapes and sizes. I probably didn't get a true sample of penis sizes, since almost all the ones I saw belonged to freshmen—and most often the victims were the smaller freshmen who really hadn't started developing much yet. Harvey was certainly in that category.

I'd say the smallest penis I ever saw at Roosevelt belonged to a boy named Johnny. I mentioned in the introductory chapter that a girl named Felicity had abused and humiliated a boy named Blondie while Blondie was an upperclassman. Well, she had other victims—all freshmen—and Johnny was one of them. Anyway, as small as Harvey's penis was, Johnny's was even tinier. I only saw him exposed a couple of times, but I remember getting an uncontrollable case of the giggles both times. The poor boy!

Incidentally, Harvey's and Blondie's penises were similar in size when Blondie was a freshman (I witnessed Blondie getting stripped by his sister and her friends before Felicity started at Roosevelt). Blondie's penis grew incrementally over his time there, but not by a lot. It had to be especially embarrassing for Blondie, because he was older—I did see him naked once when he was a senior—and, as I mentioned, Felicity made him keep his whole body completely hairless. So to have a hairless penis not much bigger than that of an underdeveloped freshman while at the age of 17—well, his humiliation must have been through the roof!

As I said, most of the stripping victims at Roosevelt did have a relatively small-sized penis, but there were several exceptions. I found it interesting that the boys with the smaller bits invariably took painstaking efforts to cover up, whereas the boys with average or larger penises (and those with hair), though still obviously embarrassed to be stripped naked, they sometimes didn't try to hide their bits with their hands, or at least didn't seem as self-conscious about them. The underdeveloped boys were more ashamed to have their genitals exposed, so I'm sure their humiliation was greater because of their deficiency.

* * * * *

Which brings me back to Harvey (thanks for indulging my getting a bit off track with my penis fascination). As he stood there, to say he was shamed to have his genitals exposed would be an understatement. I'm sure all of us laughing with amusement and delight only exacerbated his torment.

In hopes of getting his living nightmare over as quickly as possible, Harvey didn't wait for Victor to give him the go-ahead. With his hands behind his head and his hairless little package on full display, he began the torturous trek up the stands. His walk of shame had evolved into a walk of abject humiliation, as the wretched Harvey endured the laughter, the catcalls, and the prying eyes while he traversed the stands in his naked state. He completely avoided eye contact with anyone and had the most pained expression on his face that one can imagine.

The scene is portrayed nicely in the drawing below. While at the reunion, I was relating the tale of Harvey's walk of shame. One of the guys listening was so inspired that he pulled me aside afterward. I had mentioned that I was considering writing these memoirs, and he offered to draw this picture for me, and that I was welcome to use it. I took him up on the offer, and I'm glad I did. Harvey was a little shorter and slenderer, but I think you'll agree that Harvey's shameful walk is captured splendidly in the rendering below.

The artist goes by the online moniker of clashofstyle, and you can see more of his impressive work by Googling "clashofstyle art."

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As Harvey's humiliation increased, so did his pace. What started out as his mandated slow walk—much to my pleasure, as I ogled him while he passed by me—gradually progressed to a faster walk, then a slow trot. After reaching the top and turning around, he galloped pretty much all the way down. The hysterically laughing Victor did nothing to rebuke him. I mean, he probably figured that under the circumstances it was almost physically impossible for Harvey to do anything but break into a run. His humiliation was that intense.

Victor let him run right past him and straight to the front rail, where he feverishly threw on his clothes. He grabbed his shoes and socks and carried them away while running barefoot, disappearing into the distance, where the sounds of laughter surely were still ringing in his ears.

* * * * *

I didn't realize it until after the event, but Harvey was in my 4th period Spanish class that year. I really enjoyed running into him. I can tell you with certainty that he did not enjoy running into me. Whenever we crossed paths (okay, I know this is a little mean, but I couldn't help myself) I would look him up and down and smile. He would blush every time—and I would enjoy it every time—and I never had to say a word. Just looking at him with a devilish smile was equivalent to me saying, "I saw you naked." You could probably add, "And I know you have a small penis," for good measure.

There was another girl in our Spanish class who took it a step further. She was also in the stands on that ill-fated (well, for Harvey) day. She would often pass by him, smile and say, "Como esta tu pene diminuto hoy?" I understood all the words except "pene diminuto," so after the third time I heard her say that to him I looked it up. I broke out into laughter when I learned that the English translation is "How is your tiny penis today?" I'm willing to bet that Harvey looked it up, too. Oh, the poor boy.

* * * * *

In closing, I want to mention a somewhat interesting encounter I had about a week after the stripping. I was standing in the lunch line in the cafeteria, and the guy behind me asked, "How did you like the Harvey show?" I turned around and it was Victor, who had obviously recognized me.

"Oh, hi," I turned around and said while gathering my thoughts. "It was....extraordinary, that's for sure," I said with a laugh.

"Wasn't it?" responded Victor. "As I recall, you're the one who wanted us to get him naked."

I felt my face turning red. "Guilty as charged," I said, still flushing.

"Hey, that's okay, I'm glad you said something," said Victor with a smile. "It helped spur me on."

"Well, I can't say I regret it," I said. "That was really fun to watch."

"Yeah, glad I could help," grinned Victor.

"Hey, I have to ask," I said. "Is that walk of shame really a tradition?"

"It is now," said Victor with a twinkle in his eye.

I knew right then and there where I would be spending my lunch hour over the next three Septembers.
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Underpants Memoirs, Chapter 5 (ENF)

Post by Blondie »

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Chapter 5: The Humiliation of Trudy Pennyfeather, Part 1

The great majority of the strippings and humiliations that transpired at Roosevelt were carried out by the students. There were a few instances, though, when a sadistic teacher would get in on the act. I know of at least three teachers who on occasion would take it upon themselves to humiliate a student.

One of those three—and probably the most infamous—is a depraved woman by the name of Gertrude Farnsworth. There are stories abound of her penchant for humiliating her students, and of her obvious enjoyment of doing so. One of her favorite tactics was to force a student to strip down to their underwear—and, in a few cases, more! She would stand there and smirk at the squirming student, and there was no question that she would be thoroughly enjoying the student's shame and humiliation.

I was fortunate enough to witness her depravity on two occasions. I'll tell you about one of them in these two chapters.

It was my sophomore year. I was 15, as was the unfortunate student who that day became another victim of Miss Farnsworth. It was soon after the beginning of the trigonometry class. I was already yawning, but my boredom would soon be alleviated, and in a big way.

Trudy Pennyfeather was a tall, athletic, slender brunette who could turn heads in the hallways—of both the boys and the girls, especially when she wore one of her tight-fitting sweaters, which she was often wont to do. She had a smallish nose that was turned slightly upward, a feature that I always thought was somewhat appropriate for her, as she figuratively turned her nose up at people like me—that being anyone who was not a part of her of select group of friends who all thought they were better than most anyone else outside of their clique. I never cared for her, which made it that much more appetizing for me when I sensed that she was about to fall prey to the perverted Miss Farnsworth. I think I literally licked my lips in anticipation.

The tediousness of listening to Miss Farnsworth drone on about sines, cosines and tangents took a distinct turn—for the better, in my estimation :)—when Trudy Pennyfeather decided to pop two sticks of chewing gum into her mouth. Chewing gum in class was against the rules, but in a normal environment, on a scale of one to ten the seriousness of the offense ranked somewhere between one and three.

But there were days when a class with Miss Farnsworth would resemble anything but a normal environment. I think there were days that Gertrude Farnsworth's desire for doling out humiliation was so strong that she would find any excuse possible to satisfy that desire. And, unfortunately for Trudy Pennyfeather, the day she decided to stuff some gum into her mouth in Miss Farnsworth's class was one of those days, and poor Trudy had no inkling of the dreadful consequences she would face because of her relatively innocuous act.

"So the hypotenuse of the triangle....Miss Pennyfeather!" barked Miss Farnsworth.

The startled student jerked upright in her seat. I was sitting directly to her left, so I was in a good spot to observe whatever would transpire. "Yes, Miss Farnsworth?" asked Trudy, playing innocent for the time being.

"Are you chewing gum, Miss Pennyfeather?"

Trudy hesitated, probably thinking she might be able to weasel out of her jam. But she realized she had been caught red-handed. "Yes, Miss Farnsworth," she replied. "Sorry, Miss Farnsworth," she quickly added.

The teacher walked the few steps necessary to stand in front of the now nervous Trudy Pennyfeather. "Do you know what the rules are regarding chewing gum in class, Miss Pennyfeather?" she asked.

"Yes, but....." Trudy tried, but really had no recourse.

"Do you think you deserve to be punished?" asked Miss Farnsworth.

"Please, I....I promise I won't do it again, Miss Farnsworth."

"Do you have any more gum?" asked Miss Farnsworth as she looked down at Trudy's backpack.

"Yes," she said.

"Let me have it."

The discombobulated student fumbled around her backpack and eventually pulled out a package that contained four sticks of gum. She put it in the outstretched hand of Miss Farnsworth. Curiously, the teacher opened one of the wrapped sticks and stuffed it into her own mouth. Then another piece. And another. Then the last piece. We were all looking at her, truly wondering where this was going.

"Do you know what shame punishment is, Miss Pennyfeather?" she asked as she chomped on the big wad of gum. I had heard that the twisted teacher started out all her humiliation sessions with that question. I suspect it was part of the foreplay for her, to help get her juices flowing, so to speak.

"I....please, I...."

"Answer the question, Miss Pennyfeather."

"Yes....um....I guess....I guess it is punishment that....that shames people."

"Very good, Miss Pennyfeather. I'm glad you understand, because you are going to be shamed today. When we are done, I'm fairly certain that you will never chew gum in my classroom again."

I felt my heart beating faster in anticipation. Trudy's face had turned pale, and I'm sure her heart was also going at an accelerated pace.

Miss Farnsworth held her open hand out in front of the anxious student's mouth. "Spit out your gum," she ordered. She did so, and Miss Farnsworth took the gum from her palm, stretched it out, and meticulously fixed it across the bridge of Trudy's upturned nose. "You're to leave that there for the rest of the school day," she instructed. Trudy's face was now very red, and she looked like she wanted to just crawl away into a hole somewhere. I thought that would be the end of her disgrace, but there would be more. Oh, so much more. Miss Farnsworth reached into her mouth and extracted the huge wad of gum that she had been masticating. She held it up to the mouth of the appalled Trudy. "Open your mouth," she said. Trudy was wide-eyed and resistant to the unseemly request. Well, it really wasn't a request. "Open it!" she bellowed, much more forcefully. Trudy succumbed to the coercion. When she opened her mouth Miss Farnsworth deposited the wad of gum onto her tongue. Cries of "Eww!" rang throughout the room. It was pre-Covid times, but it was still disgusting. And much more so for Trudy Pennyfeather, I'm sure.

The bewildered Trudy left her mouth wide open, temporarily unable or unwilling to accept the latest violation of her sensibilities. "Close your mouth and chew," pressed Miss Farnsworth. "It was your choice to chew gum in my class. Now you're to chew on that gum until class is over." We all watched as the beleaguered Trudy closed her mouth and forced herself to bite into the gum that included the spittle of her antagonizer. As Miss Farnsworth turned and walked back toward the front of the room, I was sure that the shaming of Trudy Pennyfeather was complete.

But I grossly underestimated Gertrude Farnsworth's predilection for enforced humiliation. And, truth be told, I'd be lying if I said I wasn't stimulated by what ensued.

Before Miss Farnsworth reached the front of the room she said in a loud voice, without turning around, "Miss Pennyfeather," she said. "Please remove your shoes and place them on my desk."

"Oh, here we go," I heard someone behind me murmur jovially. It was obviously someone familiar with Miss Farnsworth's history.

"Showtime," giggled another.

I looked over at Trudy and she had a horrified, surprised look on her face. Either she was unaware of Miss Farnsworth's humiliation tendencies, or she thought she was immune to them. I reflexively looked down at her shoes. She was wearing a pair of sandals, no socks. In anticipation, I took in the rest of her clothing, which consisted of a pair of skintight jeans and a close-fitting lavender sweater. I wondered if she would be wearing them for much longer and smiled to myself.

Miss Farnsworth reached her desk, then turned around and stared at the aghast Trudy Pennyfeather, who had not moved a muscle. "Miss Pennyfeather," admonished the teacher, "If your shoes are not on my desk in three seconds, you will be sorry. One...." Trudy must have still been too dumbfounded to move. "Two....." Trudy reached down and removed her sandals, then rose from her seat. "And, three," we all heard her say while Trudy was only halfway to the desk, sandals in hand. Trudy reluctantly laid her sandals on the desk and turned to retreat to her seat. "Hold it right there, Miss Pennyfeather," instructed the teacher. Trudy winced and stopped in her tracks. "You did not obey me in a timely fashion, Miss Pennyfeather, and I told you that you would be sorry if you didn't," said Miss Farnsworth. Trudy still had her back to her so I was able to take in her pained expression. "Turn around and face me while I'm talking to you," admonished Miss Farnsworth. The now petrified student slowly rotated and faced her adversary. "And chew on our gum," was her next directive. "I expect to see you chewing on our gum for the rest of this class."

"Our" gum? She is such a devil.

"Now, Miss Pennyfeather," continued Miss Farnsworth. "You're to remove your blue jeans and place them on my desk." Gasps of astonishment echoed throughout the classroom. Trudy Pennyfeather again was too stupefied to move.

"But Miss....Miss Farnsworth...." she whimpered.

"No buts!" roared Miss Farnsworth. "Take those jeans off immediately, or you'll be sorry!" I think she was already sorry. But there were various degrees of "sorry" in Miss Farnsworth's class, and apparently Trudy Pennyfeather had not yet reached a high enough level of sorriness.

One may be wondering why Trudy (or any student, for that matter) would submit to Miss Farnsworth's deviant demands. I asked myself the same question. All I can say is that Miss Farnsworth had a very authoritarian, intimidating way about her. There was a feeling that to defy her would only invite even more dire consequences. Plus, there would certainly be no recourse in going to the principal, or any other person of authority. Such was the climate at Roosevelt High School.

So, to no one's surprise, yet at the same time to a certain amount of everyone's disbelief, Trudy Pennyfeather reached for the top button of her snug-fitting blue jeans. The room was very quiet, but for the soft sniveling I could hear emanating from mouth of the star attraction. I watched eagerly as the traumatized student finished with the rest of her buttons, then, with a fair amount of effort, pushed her jeans down to the tops of her knees, revealing a pair of black panties. (Incidentally, the panties were a close resemblance to the picture of the panties that I used for the cover art of these memoirs.) We could only see the bottom half or so of the panties because Trudy had taken great pains while lowering her jeans to make sure to pull down on her sweater, stretching it as far as she could to conceal as much material of her panties as humanly possible. I'm sure that did little to assuage her acute embarrassment, though. As she struggled to get her jeans off, I caught glimpses of her face, and her cheeks were blushing profusely. It didn't help her cause at all that her jeans were so tight, as it only prolonged her task, and thus her embarrassment. She always seemed to be pulling her sweater down with one hand while pushing on her jeans with the other.

She finally did manage to wrestle her jeans off her feet and lay them on the desk. I sized her up (as I'm sure everyone did), and she had beautiful, long, shapely legs. Her tan line was high up her legs, and moving upward one could see the white skin at the tops of her thighs feed into the black material of her panties.

Trudy stood there momentarily with her back to us, while continuing to stretch her nice sweater down as far as she could. Hard as she tried, she still only managed to cover about half of her panties. Quite self-consciously, she also tried adjusting the back of her panties slightly downward, but I could still make out the very bottom of her shapely buttocks.

Trudy turned to go to her desk, but again was waylaid by the diabolical Miss Farnsworth. "Miss Pennyfeather, did I say you could return to your desk?" she asked.

"No, Miss Farnsworth," said the admonished Trudy as she turned back around.

"That is correct, Miss Pennyfeather, I did not. Yet you continue to act like you have the upper hand in this situation. Do you think you have the upper hand, Miss Pennyfeather?"

"No, Miss Farnsworth."

"I wouldn't think so," replied the teacher as she looked Trudy up and down. "You're standing there depantsed and barefoot in front of all of us. You have gum draped over your pretty little nose, plus you're chewing on a fat wad of gum that is impregnated with my saliva. You're blushing brilliantly, obviously in a state of acute embarrassment. So, you're presenting a girl who not only doesn't have the upper hand, but is in a decidedly inferior, submissive position." She let that sit there for a spell. I couldn't see her face, but I suspect that Trudy's face turned even redder. She stood still with her head facing downward while persistently pulling on her sweater. That was about to change. "Pull your sweater up above your navel," ordered Miss Farnsworth. She slowly did so, unveiling the rest of her panties, along with a few inches of freshly bared skin. I don't think I was the only one in the room becoming a bit more stimulated. "You may return to your seat now," said Miss Farnsworth.

Only slightly relieved, the abashed Trudy Pennyfeather turned and scurried to her seat. Not really knowing what to do with her hands, she had them clasped to the front of her panties. She took her seat, knowing the eyes of everyone in the room were focused on her, and that many of us were probably deriving pleasure from her humiliation. I must admit that I couldn't take my eyes off her. I watched delightedly as she squirmed in her seat.

After a while she couldn't take it anymore, and again pulled her sweater down, which brought an immediate reprimand from Miss Farnsworth. "Miss Pennyfeather!" she bellowed. "Did I say you could lower your sweater?"

"S-Sorry, Miss Farnsworth....I just...."

"It's too late for sorries," said Miss Farnsworth as she stormed down the aisle and stepped behind Trudy's chair. She reached around her and took hold of the hem of her sweater with both hands. "Arms up," she ordered.

Trudy was beside herself. "Miss Farns...."

"ARMS UP!" she repeated, with considerably more force. Trudy, intimidated and panic-stricken, thrust her arms up in the air. The fiendish teacher wasted no time pulling the sweater upward. I could hear Trudy yelping something unintelligible through the material as it momentarily passed over her face. A split-second later Miss Farnsworth was walking back to her desk, sweater in hand, while the agonized Trudy Pennyfeather writhed anxiously in her seat, clad only in her underwear, which consisted of a matching bra and panties set.

For me, it was a sight to behold. Now, I'm not gay, or even bisexual, but I can tell you that I was sexually aroused while I gawked at her. She had a beautiful body, and her bra and panties were exquisitely sexy. The fact that she was stripped to her underwear against her will in front of the whole class....well, that put it over the top for me.

To be continued....
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Underpants Memoirs, Chapter 6 (ENF)

Post by Blondie »

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Chapter 6: The Humiliation of Trudy Pennyfeather, Part 2

As Trudy Pennyfeather continued to writhe in her seat, I was mesmerized. The vision of the mortified student stripped to her underwear was pure eye candy for me. I'm sure the boys (consider the raging testosterone of 15-year-old boys) were enjoying themselves on an even higher level than I. I'd venture to say that the over/under for the percentage of boys with hard-ons was probably at least 75%.

As for Trudy, when I try to imagine myself in her situation.....well, put it this way, I blush just thinking about it. There she was, sitting among all her classmates clad only in only her black bra and panties. To boot, she had a strip of gum draped over the bridge of her nose. Plus, she was forced to continue chewing on a big wad of gum that originated in the mouth of the sinister Miss Farnsworth. And, incredibly, her shameful plight was about to worsen.

But before I go on, I have to tell you something—something I've been holding back. I wasn't going to put this in these memoirs—mainly because I am still embarrassed about it to this day—but I think full disclosure would be best.

It was during my freshman year. I was standing on the grass near the soccer field, talking to a boy that I was interested in. I didn't know Trudy Pennyfeather at the time, but she was standing nearby with her usual clique of friends. I was wearing a black elastic skirt, and a top that came down to just below my belly button. Then, out of the blue, Trudy Pennyfeather snuck up behind me and pulled my skirt all the way down. As I reached down to pull it back up, she shoved me forward, and I fell to the ground, but not before stepping out of my skirt. Trudy grabbed my skirt and ran toward her friends. With laughter all around (and my light green, cotton panties on full display!) I chased her, and when I almost caught her she tossed my skirt to one of her laughing friends. They played keep-away with me for a bit until I nabbed my skirt in midair. The whole thing probably lasted less than a minute, but it was by far the most embarrassed I've ever been. I know my face was bright red, as it felt like it was on fire.

I felt compelled to tell you that story so you would know that when Miss Farnsworth picked a student to be her victim that day, my enjoyment level was heightened considerably by the fact that it was Trudy Pennyfeather. I felt she was getting her just comeuppance.

Anyway, back to the wonderful details of Trudy's humiliation. She was leaning a bit forward, with her arms crossed over her chest. She was hiding them at the moment, but we all were aware of the size of her boobs. Like I said, Trudy often wears a tight-fitting sweater. The one she was wearing ("was" being the operative word, LOL) today flaunted her endowment rather prominently. Plus, I caught a quick glimpse of her chest while Miss Farnsworth was pulling off her sweater. Sitting directly to her left, I had a good vantage point. She has disproportionately large breasts, considering her slender physique.

I continued to enjoy the display, until Miss Farnsworth interrupted my fascination. "Miss Pennyfeather, would you come up here, please?" she asked.
An energetic murmuring could be heard throughout the room, as we all anticipated the delicious scene of Trudy Pennyfeather parading for us in her underwear. And we would not be disappointed.

Trudy momentarily hesitated, but everyone—including Trudy—knew that she would have to do Miss Farnsworth's bidding. She reluctantly extricated herself from her chair and, with her arms still crossed over her chest, made the short but torturous walk to the front of the room. All eyes were on her, and her fellow students were, figuratively speaking, devouring the scene. She stopped in front of Miss Farnsworth's desk. I thought I detected her trembling slightly.

"Miss Pennyfeather," addressed Miss Farnsworth. "Because of your indiscretions today, you have taken up valuable time from your classmates. I think they deserve an apology, don't you?"

"I'm sorry," replied Trudy.

"Turn around and face your classmates while speaking to them, please. And lower your arms to your sides. Crossing your arms is poor body language and is disrespectful." My eye candy became more delectable as the chagrined Trudy turned and faced us. Her sexy underwear was on full display, and her face was tomato red. "Now," persisted Miss Farnsworth. "Apologize properly to the class."

"I'm....I'm sorry for....for taking up your time," obeyed Trudy.

"Good. Now tell us how you feel right now."

"I....I feel....I don't know. I'm sorry."

"Do you feel shamed, Miss Pennyfeather?

"Yes," she responded timidly. I swear she blushed brighter.

"Good, now tell us why you feel shamed."

"For....for taking up everyone's time?"

"No, I mean what condition are you in that has rendered you shamefaced?"

"I....I'm in my underwear," replied the red-faced girl. Her head was down, and her stare was fixated on the floor in front of her.

"Yes you are!" replied the devilish teacher. "Everyone else is fully clothed, and we're all basking in the vision of you stripped to your underwear." Miss Farnsworth remained silent for a spell. Trudy stood there squirming, not really knowing what to do with herself while we....well, while we basked in the vision of Trudy stripped to her underwear.

Finally, Miss Farnsworth was ready to proceed. "You may return to your seat, Miss Pennyfeather," she said. Trudy didn't have to be told twice, and she scuttled back to her seat. She quickly sat down and, as before, she leaned forward with her arms across her chest.

Meanwhile, Miss Farnsworth stood and stared at the embattled Trudy. The teacher looked like she was deep in thought, as if she was trying to come up with a plan. After a while, I detected a slight smile on her face. What she concocted was downright diabolical. "Class," she began, "I also want to apologize for the numerous interruptions of your lesson today, due to Miss Pennyfeather's misbehavior. With that in mind, I think it would only be fair to involve you in deciding Miss Pennyfeather's fate for the remainder of the period." The level of interest and intrigue was already at a high level, but it had just ratcheted up a notch. I looked over at the horror-struck Trudy, then back up to the twisted teacher. "You see," she continued, "I've been trying to decide if Miss Pennyfeather has been shamed enough, or if further punishment is in order. So I'll let you decide. Please write your thoughts on a piece of binder paper. You don't have to sign it; your thoughts will remain anonymous. They will be read out loud, so try to mind your language.

"You have several choices. You can say that Miss Pennyfeather has been shamed enough, and that she can get dressed immediately. Another option is that she is to remain in her underwear for the duration of the class. Or, if you have something else in mind, you may offer your suggestions, whatever they may be." I looked over at Trudy and smiled. I knew right away that I was going to go with "something else." "When you're finished, fold the paper in half and leave it on your desk."

It didn't take long for everyone to finish their task. I noticed that some did so rather eagerly.

"Miss Pennyfeather," said Miss Farnsworth. "Would you be kind enough to collect all the papers and bring them up to the front?" There were a few cackles of delight. Trudy's jaw dropped, and her face went pale, a color that would soon turn to crimson as she gathered herself and slipped out of her chair. I watched with relish as she traipsed up and down the aisles—as briskly as she could—in her underwear, snatching up the sheets of paper with content that could well determine her level of humiliation for the rest of the period. Many—especially the boys—looked her up and down and grinned lasciviously as the scantily clad girl passed them by.

On one occasion the harried girl dropped a sheet on the floor, affording us a tasty moment as she bent over to pick it up. As more blood rushed to her head, when she stood up her face was as red as can be.

Upon finishing, she stopped in front of the teacher's desk, holding about thirty pieces of paper. Miss Farnsworth took them from her, shuffled them and then placed them in a shallow, rectangular cardboard box. She laid the box on her desk, right next to Trudy. "Thank you, class, for your input," she said. "Miss Pennyfeather will now read your submissions aloud for us."

Oh, my goodness!

Trudy still had her back to us, but I did see her shoulders slump. The poor girl! But I knew it was going to be entertaining.

Trudy stood motionless, temporarily reluctant to do the teacher's bidding. "Stop stalling, Miss Pennyfeather. You've wasted enough of our time already. Now reach into the box, pick one out and read it for us. When you're done, hand it to me and go on to the next one." Trudy gingerly reached into the box and pulled out one of the sheets. "Turn around and face your classmates, please," instructed Miss Pennyfeather. The beleaguered girl slowly turned around and opened the piece of binder paper. As she silently read it over, a pained expression developed on her face. I was pretty sure that it didn't say that she could get dressed immediately. :lol:

"Read it aloud, please," insisted Miss Farnsworth. Trudy read from the page, but her mutterings were inaudible. "Miss Pennyfeather, you need to speak loudly and clearly so we all can hear you. If I have to reprimand you again there will be consequences."

Consequences? More severe than what she is doing right now? Yikes!

Trudy took a deep breath and read from the sheet. "Miss Farnsworth should make her.....make her take her bra off and let us see her....her titties." Shrieks of approval could be heard throughout from the increasingly enthusiastic students. Trudy stared down to the floor, probably wishing it would open and swallow her whole.

"Good," said Miss Farnsworth as she took the sheet from Trudy, looked it over and placed it on her desk. "Next?"

Trudy again reached into the box and pulled another sheet. She had no problem reading that one. "Trudy has suffered enough. She should be allowed to get dressed."

"Okay," said Miss Farnsworth. "That's one vote for putting clothes back on, and one for taking more off. Continue, Miss Pennyfeather."

Trudy continued to read her fellow students' submissions. Here is a sampling of some of the more titillating ones. All told, only two students thought Trudy should get her clothes back.

"Make her strip to her underwear in class every day for the rest of the year."

"To be thoroughly shamed, Trudy's bra and panties need to come off. She should sit at her desk completely naked for our entertainment. If she tries to cover up, Miss Farnsworth should spank her." That one elicited a huge reaction, which I enjoyed, since I wrote it.

"Make her take her bra off, split the gum in her mouth in two and put them on her nipples."

"She seems very self-conscious about her breasts. A good punishment would be to have her take her bra off and walk up and down the aisles with her hands behind her head." Another big reaction, and I have to say that the idea had me turned on.

"Completely naked!"

"Make her stand on Miss Farnsworth's desk and do a striptease dance."

"She should get a spanking for the naughty girl she is."

"Sing a song for us topless."

You get the idea. I wasn't the only one getting caught up in the moment and hoping for an uptick in Trudy's humiliation.

Trudy somehow managed to read through all the "suggestions." Her voice quivered often, especially while reading the bawdier ones.

"Thank you class, that was very helpful," concluded Miss Farnsworth. "You have spoken, and I now have a better idea on how to proceed. Miss Pennyfeather, you may return to your seat now." The sniffling Trudy turned to go back to her desk. She didn't get very far. "But first I'd like you to leave your bra on my desk."

There was a commotion in the room, as everyone seemed to sit up a little straighter in their seats all at once. There were a few squeals of surprise and delight, and a few giggles.

There were no squeals of delight or giggles coming from Trudy Pennyfeather. She stopped in her tracks and stood motionless for a moment, contemplating the newest indignity of her ongoing nightmare. Eventually she turned back around and faced her nemesis. "Please Miss Farns...." She didn't bother finishing the sentence, knowing that it would be fruitless. Instead, much to everyone's enthrallment, she slowly reached behind her and unfastened her bra. We drank in the sight of her bare back and watched in fascination as she slipped off her bra and laid it on top of her previously discarded clothes.

Trudy Pennyfeather was now topless. Our feeling of delectation was diametrically opposite to Trudy's abject mortification. The half-naked girl had her arms crossed over her newly bared chest as she turned and literally sprinted to her desk and tumbled into her seat, knowing that thirty sets of eyes were focused on her.

"Very well," said the sadistic teacher. "Now please open your books to Chapter 7 and read it over quietly."

With one eye on our textbook and the other on Trudy Pennyfeather, we pretended to study our trigonometry lesson. For her part, Trudy managed to open her book without uncovering her breasts, which she was protecting as much as possible with both of her arms. I highly doubt that she digested one ounce of trigonometry in her wretched state.

As for me, I must admit that I didn't learn any more trig that day than did Trudy. I couldn't take my eyes off her. I mean, she was almost naked, she had a beautiful body, and was embarrassed as all get-out. The circumstances were extraordinary. So yes, I was staring at her, and I was smiling with delight to boot.

As things would turn out, I am to blame (though I'm taking credit, LOL) for the escalation of Trudy Pennyfeather's humiliation. Trudy apparently found my staring bothersome. I did see her glance at me periodically, but I was undeterred in my fascination of her and her predicament. I guess it finally reached a point where she couldn't take it anymore, and she made a surprising and consequential mistake. "Stop staring at me!" she whispered to me. Unfortunately for Trudy, it was loud enough to attract the attention of Miss Farnsworth.

"Miss Pennyfeather!" she yelled, causing the startled Trudy to jump in her seat. "Why are you bothering Michelle when she's trying to study?"

"I....she wasn't studying," answered Trudy. "She was....staring at me."

"Come up here right now, young lady," commanded Miss Farnsworth. Once again the tormented Trudy traipsed to the front of the room, arms crossed over her chest. She stopped at the front of Miss Farnsworth's desk and stood there submissively. "Lean over with your palms flat on my desk," ordered Miss Farnsworth. She did so, and if I leaned to the side I could see her tits hanging down. Those sitting to my left and right had a better angle, which they all took full advantage of.

Miss Farnsworth opened her desk drawer, pulled out a paddle and walked around her desk, standing next to the trembling student.

Of COURSE she has a paddle in her desk.

"Do you think you deserve a paddling, Miss Pennyfeather?" asked the teacher.

"Please....I ...."

"Do you think you deserve a paddling, Miss Pennyfeather?" she persisted.

"Yes."

"Yes, what?"

"Yes, I deserve a paddling," she answered meekly.

"How many spanks with the paddle do you think you deserve?"

"I....I don't know....please, I...."

"How many pieces of gum do you have on your nose?" asked the teacher.

"Two," said Trudy quietly.

"How many pieces of our gum do you have in your mouth?"

"I don't....um, four?"

"Sounds like you deserve six of the best." While we looked on intently, Miss Farnsworth walked to Trudy's other side and readied herself. "Are you ready for your paddling?" she asked.

"No....please...."

"Are you ready for your paddling?"

"Yes."

"Yes, what?"

"I'm ready....ready for my paddling. Oh, please!"

Miss Farnsworth reared back with her right hand, appeared to be ready to strike.....then she stopped. She set the paddle down on her desk next to Trudy, walked behind the frightened girl, and without a word she lowered her panties down to her knees, exposing her nicely rounded bottom for all to see. Trudy let out a yelp, which I was able to discern over the uproar that emerged from her highly entertained classmates. I was looking closely, and her tush was twitching becomingly. The entertainment level was high.

"I'd like you to count them for me, Miss Pennyfeather. And after each spank, you're to say, 'I'm sorry, Michelle'." I couldn't suppress a giggle. The whole scene was so delicious.

(I should interject that Miss Farnsworth was aware of my de-skirting at the hands of Trudy the previous year. After I pulled my skirt back on I looked around at all the entertained witnesses. Miss Farnsworth—who was smiling, of course—was one of them.)

The next sound we heard was a loud "THWAP!" as the nasty paddle smacked into Trudy's left butt cheek. "Oh! One......thank—I mean, I'm sorry, Michelle!" Then another "THWAP!" as her right butt cheek was serviced accordingly. "Two! I'm sorry, Michelle!" THWAP! "Three! I'm sorry, Michelle!" THWAP! "Four! I'm sorry, Michelle!" Trudy's cheeks were already turning pink. All of us were watching in fascination, many of us open-mouthed, somewhat awestruck by the extraordinary spectacle. THWAP! "Five! Oh! I'm sorry, Michelle!" THWAP! The last one was delivered with a little extra gusto. "Ow! Oh, gosh! Six! I'm s-sorry, Michelle!"

Miss Farnsworth laid the paddle down on her desk. Trudy started to lift up, but Miss Farnsworth gently pushed her back down by the back of her neck. "Remain in that position for a few moments," instructed the teacher. "Your bottom is still getting rosier, and I think it will be enjoyable for your classmates to watch it develop into a nice shade of red." We all focused on Trudy's increasingly reddening ass cheeks. She obviously knew it, and she occasionally would use her gluteus muscles to squeeze her cheeks together. I slowly shook my head in wonder at the whole unbelievable scene.

Miss Farnsworth stepped behind Trudy momentarily and ogled along with us. "Oh, yes, they're turning a nice, pretty shade of red," she remarked. "I'll bet your bottom feels quite warm, doesn't it, Miss Pennyfeather?"

"Y-Yes," we heard her murmur.

"Class, while we're waiting for Miss Pennyfeather's bottom to achieve its fullest degree of reddishness—and I think we're getting close, because it's glowing rather nicely right now—we should decide on the future state of play regarding Miss Pennyfeather's panties." We collectively looked up from Trudy's naked bum to Miss Farnsworth's face, then down to Trudy's panties, which remained at half-mast, held up only by Trudy's slightly spread knees. "Let's have a show of hands. How many of you would like Miss Pennyfeather's panties pulled back up?" Not surprisingly, only a couple of hands went up in the air. "Okay, now how many of you would like Miss Pennyfeather's panties to remain where they are?" A good majority of the students' hands went up, including mine, mainly because we didn't realize there would be a third option. "Now, how many of you would like Miss Pennyfeather's panties removed completely?" Other than the two dissenters, everyone's hand abruptly shot up in the air.

If the wretched Trudy was unaware how the vote came out (though I think at this point she had a pretty good idea), Miss Farnsworth ended her suspense straightaway. And I would be the benefactor, in more ways than one. "Miss Pennyfeather, your classmates have spoken, and it is clear that they would like you to be divested of your panties." Trudy stood silently and motionless as she absorbed her imminent indignity. "Michelle," said Miss Farnsworth, "Would you like to do the honors?"

"Certainly, Miss Farnsworth," I said as I blissfully sprang from my chair. I bounded to the front of the room and stood behind the soon-to-be-nude Trudy. I was caught up in the moment, and I played my part to the hilt. I placed the tips of my fingers high on Trudy's sides, ever so close to her breasts. While I was there I used my index fingers to fiddle with her nipples, causing her to flinch and let out a small yelp, much to my delight. I then slid my fingers down her sides, caressing her skin slowly, tenderly, and teasingly until I reached the tops of her panties. I smiled devilishly when I noticed her trembling at my touch. I then slipped my fingers inside her panties, on the outsides of her knees, and ever so slowly, while maintaining full contact with her skin, I lowered my hands down as far as I could. Trudy's panties came along for the ride, and when I pulled my hands out her panties were resting at her ankles. I kneeled and tapped the outside of her left ankle, indicating for her to lift her leg, but she didn't budge. Not wasting any time, I stood up and gave her reddened ass cheeks two hard swats with my open palm.

"Oh! Ow!" she squealed, as much from shock and shame as from pain. Again I kneeled and tapped the outside of her left ankle. This time she was compliant, and when she lifted her leg I slipped the material free from her foot. I tapped her right leg, and after a moment's hesitation she lifted it up, allowing me to gleefully strip off her panties. I turned and proudly held up the panties with both hands for all to see, eliciting a boisterous reaction from Trudy's classmates, furthering her already staggering humiliation. For a final touch I spread Trudy's panties out on Miss Farnsworth's desk, directly below the profusely blushing face of the hapless victim. Before walking away, I rested my palm on one of her bare ass cheeks.

"You're right, Miss Farnsworth. Miss Pennyfeather's bottom is quite warm," I said before strutting back to my seat, quite full of myself over the performance.

"Very well, then. Miss Pennyfeather, you may return to your seat now." Trudy started to reach for her panties but thought better of it. (A wise decision on her part, knowing Miss Farnsworth.) She turned, and with a couple of tears trickling down her cheeks, she had one arm over her breasts and her other hand over her sex while she quickly strode to her desk and plopped into her seat.

I had gotten my wish. Trudy Pennyfeather was sitting at her desk, completely naked, for our entertainment. To say I felt vindicated would be an understatement. Of course, I continued to stare at her for the remainder of the period. I so enjoyed watching the naked, beyond mortified Trudy squirming in her seat, covering her breasts and her vagina like her life depended on it. Occasionally she would glance over at me. I know she hated me staring at her, and I'm sure she didn't appreciate the smirk on my face.

Miss Farnsworth addressed her one more time, adding more spice to the moment. "Miss Pennyfeather, could you stand up, please?" Trudy forced herself out of her chair. She was slightly bent over, with her hands and arms in their most strategic spots. "Do you feel shamed, Miss Pennyfeather?" asked the teacher.

"Y-Yes," she replied, with her eyes peeled down to her toes.

"Tell us why you feel shamed, Miss Pennyfeather."

"Um.....because.....I'm....I'm naked." There was giggling all around. I can't quite explain why, but it was both humorous and stimulating to make the humiliated naked girl tell us that she was naked.

"Yes, I can see that. It must be quite shameful to be standing there on display, naked as a jaybird." There was no response, and Miss Farnsworth persisted. "Isn't it, Miss Pennyfeather?

"Yes."

"Yes, what, Miss Pennyfeather?"

"It is shameful to.....to be on display."

"What else?"

"And to be naked."

"Excellent," said the teacher. "Now, class, you can go back to reading Chapter 7 in your textbooks. Miss Pennyfeather can stand there on naked display while you study."

And she did. Not much else transpired, but Trudy was forced to stand naked by her desk for the remainder of the period. I was sort of hoping Miss Farnsworth would make her do something else, like walk up and down the aisles naked, or at least make her move her hands to her sides—or better yet, on top of her head. That didn't happen, but I have to say that to this day I still smile—and, yes, become sexually aroused—whenever I conjure up the images of Trudy Pennyfeather's humiliation.

As I passed by the teacher's desk at the end of the class, Trudy was hastily pulling on her clothes. I made eye contact with Miss Farnsworth.

"Thank you," I said.

"It was my pleasure," she answered honestly with a smile on her lips and a twinkle in her eye.
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Re: Underpants Memoirs

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Shouldn't this be in the ENF section?
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Re: Underpants Memoirs

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Jeepman89 wrote: Sat Aug 17, 2024 1:59 am Shouldn't this be in the ENF section?
This is a hybrid story containing both ENM and ENF chapters (mostly ENM). I didn't want to break up the story, so I posted these two chapters here (and also in the ENF section). Sorry if that's a problem. I did label the chapters ENF so one could simply skip over it if they so desired. The next chapter(s) will contain ENM, FWIW.
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Re: Underpants Memoirs

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No worries. Thanks for clearing that up.
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