Underpants Memoirs

Stories about boys ending up in compromising situations, preferably naked and embarrassed, as the name suggests.
User avatar
Blondie
Posts: 322
Joined: Tue May 16, 2023 7:09 pm
Has thanked: 151 times
Been thanked: 723 times
Contact:

Underpants Memoirs

Post by Blondie »

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

Image

Chapter 1: Introduction to Roosevelt High

Hi there! My name’s 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.

Sure, every school has its fair share of hazings and bullying, the occasional prank or freshmen being picked on. But at Roosevelt it was taken to a whole different level.

Scratch that—it was a 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 absolute mortification. The number of public strippings and humiliations I witnessed during my four years there was, frankly, mind-boggling.

Don't get me wrong—I absolutely loved being part of that culture.

There was always a buzz in the air—an electric anticipation that anything could happen. You never knew when you’d round a corner and stumble upon some frantic freshman fighting to keep his pants on. And when it happened, well...I’ll admit it—I found it quite titillating. So did most of my classmates. To this day, I still get a delightful little thrill just reminiscing about the deliciously sordid things I saw within the hallowed halls of Roosevelt High.

Which brings me to this memoir. 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.

That night, the idea struck me: Why not preserve these memories? I began scribbling down notes on a few cocktail napkins as the stories poured out. Between those notes and my fairly vivid memory, I think I can retell these episodes in vivid, storybook fashion—which hopefully will be enjoyable for the reader—and for me. :D

Before I close this intro and move on to the first humiliation tale, I feel I should address a question you might be asking: “Where were the adults in all of this?”

Oh, they were there. They just looked the other way.

I’ll never forget the first time I saw a boy get pantsed in the hallway. I was a freshman, stunned beyond belief, and I watched as three separate teachers turned and walked in the other direction. Later, I 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.

Well, that didn’t go over well.

Revenge was swift. Less than 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 spread like wildfire through the faculty. The teacher never named names, but everyone knew who did it, and why.

And just for good measure, the principal—Mr. Jerry Radcliffe, a rather smallish man—was ambushed in front of his home. He was shoved into the backseat of a car, driven off, and returned two hours later...stark naked. He was dropped off two blocks from his house, humiliated and shaken. Only he and the perpetrators 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 were 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’ve called this little project Underpants Memoirs. After all, many victims weren’t just stripped to their underwear—some were stripped completely naked. And yes, those instances were always especially thrilling.

But personally? I’ve always had a particular fascination with the tighty-whities. There’s something especially delicious about watching a panicked, red-faced freshman struggle as he’s reduced to those snug little white briefs. And 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.

Oh, and while most of the victims were freshman boys, there was one notable exception. It 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 even 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, cheeks burning with shame. Another time, Felicity had him drop his pants in the courtyard. But instead of briefs, he was wearing panties. With his smooth legs and small frame, the poor boy looked downright feminine. I got a pretty good laugh out of that, not to mention a bit of a sexual arousal over his humiliation.

And speaking of panties—you might’ve noticed that the cover of this memoir features a cute little pair. That’s because, while 90% of the strippings were boys, there were a few female victims, too. They were usually left in their bra and panties—though I do know of two girls who were stripped naked.

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.

Trust me...Roosevelt had no shortage of material.
Last edited by Blondie on Mon Jul 07, 2025 11:32 pm, edited 2 times in total.
User avatar
Blondie
Posts: 322
Joined: Tue May 16, 2023 7:09 pm
Has thanked: 151 times
Been thanked: 723 times
Contact:

Underpants Memoirs, Chapter 2

Post by Blondie »

Image

Chapter 2: First Tighty-Whities Sighting

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

It happened during my second week of freshman year. I was cutting across the courtyard during recess, headed toward the vending machines for a quick snack before my next class. But I’d barely made it halfway when I heard a high-pitched shriek ring out near the Roosevelt statue.

“No! Please stop! Nooo!”

Naturally, I veered toward the noise. A cluster of students had gathered near the base of the statue. 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.

Flat on his back in front of the statue was a small-framed freshman, squirming furiously as four much larger boys held him down—one on each limb. Towering above them was a fifth student, standing on Roosevelt’s outstretched marble arm, gripping the statue’s neck for balance.

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 opposite directions.

I couldn't explain why, but I felt a flutter deep inside. I knew I should’ve felt sorry for the poor kid—but watching those shoes and socks fly, watching him struggle so helplessly—it sent a strange little thrill through me. And I found myself hoping they wouldn’t 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. The next move was to untuck his shirt. I actually gasped when I saw them pull it free from his waistband, exposing his flat, pale belly. I think I trembled a little. The unmasking of skin—and the now likely possibility for more—was a thrilling prelude to what was to come.

He must’ve sensed it too. His struggles grew frantic, his pleading more desperate. Somehow, his flailing only made the whole thing more delicious.

The crowd around us swelled, wide-eyed and grinning, hungry for whatever came next.

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.

But the tickling was only an appetizer. The main course came next.

My breath caught as one of them began undoing his belt buckle.

"No! Oh shit! Oh God! No! Please!" he wailed, his voice rising into pure panic.

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 small stature. 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, 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.

Eventually, he gave up on the jumping and began to climb. I continued to laugh out loud as I watched him wiggle up the statue. He wrapped his bare legs around the cold marble and shimmied up awkwardly, exposing even more of himself than I'm sure he wanted to. I, for one, thoroughly enjoyed the eye candy—especially the teasing peek of his little butt crack as he inched his way higher.

It took real effort, but he finally managed to perch himself on the outstretched 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. He finally gave up and tossed his jeans to the ground. The crowd cheered.

Then came the shirt. He pulled it 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, to the sound of more cheering and laughter.

Still in nothing but his tighty-whities, he slid down the statue, bare legs wrapped around Roosevelt’s torso, and hit the ground running. His face was bright red. I mean, full-on tomato. I’d never seen anyone look so mortified in my entire life—and no wonder!

He scooped up his scattered clothes and dashed to the far side of the statue to dress in peace, away from the still-laughing crowd.

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 as I entered the building of the school like no other.
Last edited by Blondie on Tue Jul 08, 2025 10:45 pm, edited 1 time in total.
User avatar
Robert Brooks
Posts: 162
Joined: Fri Jan 06, 2023 1:45 am
Has thanked: 649 times
Been thanked: 199 times
Contact:

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…?
User avatar
Blondie
Posts: 322
Joined: Tue May 16, 2023 7:09 pm
Has thanked: 151 times
Been thanked: 723 times
Contact:

Underpants Memoirs, Chapter 3

Post by Blondie »

Image

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.

Down in the front row, three levels below us, sat a lone freshman. He was a cute boy with a slight frame, and he didn't look a day over 12—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 boys—probably juniors or seniors—approached him. Two flanked him on either side, sandwiching him on the bench. The other two casually plopped down in the row just in front, boxing him in completely.

From our vantage point, I had a perfect view—and I could hear just enough to follow the unfolding drama.

“How’s it going?” said the one to Harvey’s left, his tone one of fake friendliness. “I’m Victor. What’s your name?”

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,” Victor continued, flashing a grin. “This is Brent,” he said, motioning to the thick-armed guy on Harvey’s right, who smiled 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,” Harvey replied, his voice wary.

From my spot in the bleachers, I exchanged wide-eyed glances with my friends. We could all sense it—something was about to go down. The suspense was palpable, and my heart was already racing a little.

Would it be another stripping? God, I hoped so.

I looked around. Dozens of other students had tuned in to the scene unfolding below. Most of them were girls. I’d later find out that whenever a boy was about to be stripped, the instigators made sure the audience was stacked with female spectators. Something about female eyes made the humiliation that much sharper.

Meanwhile, Harvey sensed that it would be in his best interests to vacate the premises as quickly as possible. He made a move to stand but was immediately returned to his seat by a forceful hand pushing on his shoulder.

“Don’t go,” Victor said, all smiles. “We just want to get to know you. Plus...we’ve got a little 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,” said Lenny from the front row.

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.

“Well,” Victor said cheerfully, "I guess we'll have to just see for ourselves,"

And with that, he reached around behind Harvey and slid his hand down the back of his dark brown corduroys. Harvey yelped and twisted, trying to stop him, but it was too late. Victor triumphantly yanked the waistband up past the small of his back—revealing a flash of white fabric, along with its pale blue striped band.

“Tighty-whities,” called out the guy on Harvey's right.

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

I was becoming more enthralled by the second.

Harvey made another feeble attempt to escape, but it was hopeless. Two of the boys pinned him down effortlessly. He wasn’t going anywhere.

“Relax, Harvey,” Victor cooed, patting him on the shoulder. “If you just do what we say, this’ll go much easier for you.”

“Please,” Harvey begged. “Just let me go.”

“We will,” Victor replied. "But first you have to do something for us."

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. "Like 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 gets the honor of taking a little stroll up and down the bleachers...in nothing but his tighty-whities.”

My eyes widened and my jaw dropped. 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...I can't do that," Harvey stammered.

Harvey, for the first time, turned around and looked back warily—toward us. 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,” Victor replied coolly. “But he still ended up doing the tighty-whities walk of shame—starting from that very spot. And so will you.”

One of the boys in front leaned forward and reached for Harvey’s shoelace. Harvey instinctively pulled his foot away, but it only earned him a warning.

“If you try to fight us, it'll only make it worse for you," Victor said.

Harvey glanced back over his shoulder again. The look on his face was that of a frightened little schoolboy—one who suddenly realized he was on the brink of humiliation.

The guy reached for his shoe again, and this time Harvey gave his hand a swift kick.

“All right, that’s it. I told you not to fight us," snapped Victor. He stood, stepped behind Harvey, and wrapped him in a tight bear hug, pinning his arms to his sides. With an audible grunt, Victor lifted the flailing boy off the ground like he weighed nothing.

“Pull his pants down,” he ordered.

“No! No!” Harvey shrieked, his legs thrashing in the air. But Harvey was easy prey for the four bullies. Two of them grabbed his legs, holding them steady. The third reached for his waist.

Harvey wasn't wearing a belt, so one of the guys simply unsnapped his corduroys and pulled down his zipper. In seconds, Harvey’s corduroys were undone and tugged down his skinny legs. His shirt was already bunched up from the struggle, so his tighty-whities were on full display.

I felt my heart flutter as they came into view. He looked so adorably helpless, dangling there in just his little briefs. I glanced at my friends and saw they were equally entranced. We exchanged grins without a word—no need to say what we were all thinking.

Victor plopped him unceremoniously back onto the bench, but Harvey immediately reached down, hoping desperately to pull up his pants.

“I wouldn’t do that if I were you,” he warned. “Unless you want to be naked.”

Upon hearing that, I dearly hoped he would continue fighting back. But I'm sure the threat of full nudity clearly terrified him far more than his current predicament. He seemed to grasp, at last, that further resistance might cost him everything.

He slouched forward, crossing his arms tightly over his thighs in a pathetic attempt at modesty.

“Sit up straight,” Victor commanded.

Reluctantly, Harvey did.

“Hands on the bench.”

“Please...just let me go,” Harvey pleaded again, but he obeyed—flattening his hands on either side of him.

"We will, Harvey, we will," Victor promised. “After the traditional walk.”

As Victor spoke, the two boys in front had been quietly working. One untied Harvey’s sneakers; the other tugged them off. Then came the socks, which were stripped from his feet post-haste. They held his ankles on their laps, cradling his bare feet. Harvey made a half-hearted attempt to pull his legs away, but they maintained their grip.

And then came the part I’ll never forget.

It happened fast—but I can picture it in my mind vividly today, almost as if I am seeing it in slow motion.

Victor reached forward and took the hem of Harvey’s shirt in both hands. He began lifting it, slowly, teasingly.

“Arms up,” he said.

Harvey hesitated.

“Do it!” Victor barked.

Whimpering, Harvey complied—raising his arms high in the air.

“Please don’t!” he cried. His voice cracked as the hem rose up his stomach, his chest, then his face.

But there was another development that clearly intensified his distress. He may not have seen it—his eyes being covered by his rising shirt—but he surely felt the swift, undeniable tug of his pants being pulled across his feet.

The timing of it all was absolutely exquisite. Just as his shirt slipped from his fingertips, Harvey was treated to the deeply mortifying sight of his corduroys being whisked off his feet—leaving him seated in nothing but his snug little tighty-whities.

“Oh my goodness,” one of my friends gasped, unable to contain her glee.

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....
Last edited by Blondie on Wed Jul 09, 2025 6:40 pm, edited 3 times in total.
User avatar
Blondie
Posts: 322
Joined: Tue May 16, 2023 7:09 pm
Has thanked: 151 times
Been thanked: 723 times
Contact:

Underpants Memoirs, Chapter 4

Post by Blondie »

Image


Chapter 4: The Traditional Walk of Shame, Part 2

“Oh no! Oh shit! Oh!” cried the panicked Harvey as the reality set in—he’d just been stripped of both shirt and corduroys in one swift, humiliating motion. Now here he was, out in public, sitting in the front row of the football stands in nothing but his snug little tighty-whities.

And Harvey wasn’t the only one hollering. Cheers and laughter erupted from the two dozen or so spectators scattered behind him. I was among them, giggling with delight as I watched him wriggle and squirm in his seat, red-faced and half-naked.

"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?” he asked, his voice quivering with humiliation.

“In due time, Harvey. In due time,” Victor replied. “Lunch isn’t over for another twenty minutes, so why don't you just relax and finish your sandwich."

I nearly choked on my own saliva. Were they really going to make him eat? Like that? In just 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. “Eat,” he instructed. “You’ll need the energy—for your walk.”

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

Victor turned to his crew. “Hold him up. I'll make him eat this sandwich after I stick it up his ass."

They stood in unison, two of them grabbing Harvey by the arms and hoisting him upright. 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! Stop! I said I’ll eat it!” Harvey screamed, panicking.

Victor paused, clearly weighing the threat, then smirked and let him sit back down. Harvey, thoroughly rattled, took the sandwich and began nibbling at it miserably—still seated in just his tighty-whities while the rest of us looked on, snickering and whispering. It was both surreal and ridiculously entertaining. I swear, you never knew what to expect at that school.

“Need a drink of water to wash that down?” Victor asked.

Harvey shook his head quickly, eyes downcast.

“You really should hydrate before the walk of shame,” Victor said. “We wouldn’t want you passing out halfway up the bleachers.” He gestured toward a drinking fountain off to the side. “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 a beeline 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, his face a deep shade of red.

It was about to get redder.

"It's time," said Victor as he took Harvey by the arm and guided him to the center aisle.

Harvey reluctantly followed him, keeping his free hand covering the front of his underpants.

And speaking of those 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 for a while, because his were at least a size too small. The waist band sat well below his belly button, with the back riding up high enough to expose the very bottom of his cheeks. I couldn’t see the front—Harvey guarded it with all his might—but I imagined it didn’t leave much to the imagination. I remember silently hoping for a better look. And lucky for me, I wouldn’t have to wait long.

Victor positioned him at the base of the aisle and let go of his arm. The terrified Harvey was facing toward the football field, hunched over with both hands glued to his crotch.

“Turn around,” Victor commanded, nudging him on the shoulder. Slowly but surely, Harvey turned around and faced us.

My heart was pounding. But not as fast as his. His bare chest was rising and falling so quickly it looked like he might hyperventilate.

“Okay, here’s how it works,” said Victor. “You walk—don’t run—to the top of the stands, touch the rail, and walk back down. That’s it. When you get back, you get your clothes. Got it?”

Harvey nodded without looking up.

“Good. Now stand up straight. No crouching. Hands on your head—and leave them there. Show everyone your pits, and all of your tighty-whities. It's tradition."

My friends burst into giggles beside me. I was too breathless to join in—I just stared, wide-eyed, as Harvey hesitated, then slowly, submissively, peeled his hands away from his underpants and raised them to his head.

He was a sight to behold. I looked him up and down and there wasn’t a hair on him. I couldn’t help but wonder if that smoothness extended everywhere. Judging from what I could (barely) see in the front of his undies...probably so.

Speaking of his bits, I looked closely and there wasn’t much to behold in that department. His tight little briefs clung tightly to his hips, but even so, there was barely a hint of a bulge.

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!” Victor shouted, rallying the crowd. “Ladies and gentlemen… the traditionallllll WALK OF SHAME!”

With that, he gave Harvey a hearty smack on his ass to get him started.

And off he went. To the utter delight of the onlookers—and, I’ll admit, to a delicious wave of stimulation on my part—the profusely blushing lad began his mortifying ascent up the bleachers, hands behind his head, his snug little underpants clinging to him. The crowd erupted with cheers, whistles, and gleeful catcalls that followed him every step of the way, adding to his already extreme embarrassment. And there I sat, eyes locked on every moment, positively buzzing with delight.

At one point on his way up, an amused girl shouted out, "Can we see your little pee-pee?"—a shout that triggered a fresh chorus of raucous laughter. Poor Harvey visibly panicked and quickened his pace, desperate to end the torment as soon as humanly possible. On the way back down, he was practically trotting—a move (whether deliberate or just pure instinct) that would, unfortunately for him, backfire spectacularly.

“You went too fast,” said Victor, grinning ear to ear. “You’ll have to do it again—and this time, sloooowly.”

“Oh please, just let me go!” Harvey begged, breathless and red-faced.

“After you do it right,” Victor replied matter-of-factly. “It’s a walk of shame, not a run of shame. Now turn around. Hands on your head.”

Harvey obeyed, albeit with trembling reluctance, once again presenting himself to us again—his snug little tighty-whities on full display. Only this time, Roosevelt’s so-called “tradition” was about to get a spicy new twist.

As Victor shouted, “Go!” he simultaneously reached down and yanked Harvey’s underpants to his knees.

Harvey let out an amusing, high-pitched squeal and bent forward in blind panic, yanking his undies back up with lightning speed. It all happened so fast—but not quite fast enough. I caught just the briefest peek at the poor boy’s most private little bits, and even that fleeting glimpse was enough to send me into a fit of gleeful laughter. Judging by the shrieks and giggles around me, I wasn’t the only one who’d gotten a glimpse—and thoroughly enjoyed the humiliating little flash.

“Oh my goodness!” gasped 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 said, giggling. “I can’t believe I said that.” I paused, then leaned in with a wicked grin. “But I hope he does it.” We both laughed as we looked on intently in hopeful anticipation.

Clearly, I wasn’t alone. A chant broke out—“Na-ked! Na-ked!”—and soon nearly everyone had joined in, the rhythm echoing through the bleachers.

“NA-KED! NA-KED!”

Victor looked up at us, grinned, and turned back to his favorite freshman. He reached for the waistband again, but this time Harvey was ready, clutching his underpants like his life depended on it.

“NA-KED! NA-KED!” the chant grew louder. The energy was electric.

“Let’s do it!” said the energized Victor, and all four boys lunged at Harvey. No more playing around—they all went straight for his undies.

"No! No!" shrieked 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. But the briefs began to slide down his thighs.

"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 shins, 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 clutched the waistband with both hands while four sets of hands tugged in the opposite direction. It was a tug-of-war, and a distinctly uneven one. Yet somehow, the poor boy was holding his own. Desperation can lend surprising strength—and Harvey was drawing on every last ounce of it.

That is, until Victor got the bright idea to try a different line of attack. Abandoning the waistband, he went straight for Harvey’s ribs, digging in with ten relentless fingers. The effect was instant. Harvey howled, squirmed, twisted—desperately trying to shake free of the maddening tickles.

He succeeded in doing that—but the cost was high.

In that moment, Harvey’s fingers lost their grip, and his precious underpants slipped past his knees...then his ankles...and finally, with a triumphant tug, into the eager hands of his tormentors.

As soon as the briefs cleared his feet, the chant stopped on a dime, replaced by a single, gleeful roar: “NAKED!”

Applause, cheering and laughter broke out. It was a full-blown celebration—and an absolutely unforgettable moment.

In the immediate moments after the stripping, the unfortunate naked boy was beside himself, and reacted 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.

Eventually he dropped to his knees, doubled over with his arms planted on the ground—facing sideways, doing everything he could to shield himself. From my angle, I couldn’t see much, but that hardly mattered. The image of him crouched there, naked and red-faced, was more than enough to get my pulse racing.

And I have to admit—shamelessly, really—that I was deriving considerable pleasure from his naked shame.

I can't explain why that is—it seems cruel and maybe even a little sadistic when you think about it, being that the poor kid was enduring the humiliation of a lifetime—but I was loving every second of it.

One look around told me I wasn’t alone. The stands were alive with laughter, gasps, and wide-eyed grins. We were a captivated audience, spellbound by Harvey’s humiliation.

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," Victor persisted.

Harvey looked up, wide-eyed. "I can't...like this...can I do it...do it in...in my underpants again?"

I chuckled—not at the question itself, but at the absurdity of it. The poor kid was literally begging to do the walk of shame again in his tighty-whities. That clearly illustrated how terrified he was of the alternative.

“Nope,” said 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.

There was a pause. Harvey wasn’t moving, still paralyzed with shame.

"If you want to see your clothes again, Harvey, you'll have to do the walk," warned Victor. "And I'm not going to wait much longer."

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

He’s going to do it! He’s really going to do it!

“Nope. Hands on your head. It’s tradition.”

Harvey was silent, and again there was a standstill. Victor nodded to his crew. "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.

The crowd hushed. Every eye turned to watch.

Harvey slowly rose to his feet, still turned away from us, both hands locked tightly over his genitals. The view from behind—his bare butt on full display—was delectable. 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. And what a vision he was—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,” Victor said. “Now hands on your head. I’ll tell you when to go."

The tension was unbearable—in the best way. 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 the footage later from one of my friends.

It was an excruciating moment for Harvey. 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 slowly raised them to his head.

Gasps and delighted squeals rippled through the crowd as his tiny bits came into full view. 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 wrap up 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. Not that I'm complaining. :D

As I’m sure you’re aware, penises come in a variety of shapes and sizes. That said, I probably didn’t get a true cross-section of what’s out there, since most of the ones I saw belonged to freshmen—and most often the victims were the more delicate boys who hadn’t really begun to develop much yet. Harvey was a textbook example of that type.

Still, if we’re ranking, 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 made a sport out of humiliating a boy named Blondie when he 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!

For comparison, Harvey's and Blondie's penises were similar in size when they were freshmen. I recall seeing Blondie get stripped by his sister and her girlfriends even before Felicity entered the picture. 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. Imagine being seventeen-years-old and still looking like an underdeveloped twelve-year-old down there. His humiliation must have been through the roof!

As I said, the boys who found themselves stripped at Roosevelt tended to be smaller—not just in stature, but in every sense of the word.

There were a few exceptions, and they handled their ordeal differently. I noticed that the boys who were more generously equipped—or who at least had a bit of hair to suggest some maturity—were still embarrassed, of course, but they didn’t always scramble to cover themselves. Some even stood there red-faced but exposed, maybe hoping that confidence—or at least the illusion of it—would soften the sting of their humiliation.

But the underdeveloped boys? Oh, they were a different story entirely. They clutched themselves like their lives depended on it. Their shame was more acute, more visible—I could see it written all over their poor blushing faces. I don’t doubt for a second that their humiliation was magnified—intensified by the very thing they were trying so desperately to hide.

And I have to admit—that only made it more fascinating to watch. The smaller they were, the redder they got—and the more fun it was to witness. I know that probably says something terrible about me, but at the time I didn’t care one bit.

* * * * *

Which brings me back to Harvey (and thank you for indulging my little detour into penis ponderings). To say he was humiliated to have his genitals exposed would be putting it mildly. And with all of us laughing, pointing, and delighting in his shame, I can only imagine how much worse it felt for him.

Desperate to end his living nightmare, Harvey didn’t even wait for Victor’s signal. With his hands on his head and his hairless little package fully on display, he began his agonizing ascent up the bleachers. 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 retelling the infamous tale of Harvey’s walk of shame, and one of the guys listening was so inspired that he pulled me aside afterward. I had mentioned I was toying with the idea of writing these memoirs, and he offered to create an illustration for me—one I’d be free to include. I took him up on the offer, and I'm glad I did.

Harvey was a bit shorter and slighter in real life, but I think you’ll agree: the artist truly captured the essence of his mortifying march.

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

Image

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 actually in my 4th period Spanish class. 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’d been in the stands that ill-fated day (well, ill-fated for Harvey), and she clearly hadn’t forgotten the show. Every so often, she’d walk past him with a sweet smile and say, “¿Cómo está tu pene diminuto hoy?” I understood most of it—except pene diminuto. After hearing her say it a third time, curiosity got the better of me and I looked it up.

I burst out laughing when I discovered it translated to: “How is your tiny penis today?”

I’m almost positive Harvey looked it up, too. You should’ve seen the way he turned crimson every time she said it. Oh, the poor boy!

* * * * *

About a week later, I was standing in the cafeteria lunch line when someone behind me asked, "How did you like the Harvey show?"

I turned around and it was Victor, who was grinning freely.

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

“Wasn’t it?” he said. “I think I remember you being the one who wanted us to get him naked."

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

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

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

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

I leaned in slightly. "Hey, I have to ask...is that ‘walk of shame’ thing really a tradition?”

Victor’s eyes twinkled. “It is now.”

And right then, I knew exactly where I’d be spending my lunch breaks over the next three Septembers.
Last edited by Blondie on Thu Jul 10, 2025 6:20 am, edited 1 time in total.
User avatar
Blondie
Posts: 322
Joined: Tue May 16, 2023 7:09 pm
Has thanked: 151 times
Been thanked: 723 times
Contact:

Underpants Memoirs, Chapter 5 (ENF)

Post by Blondie »

Image

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. She had a reputation, and it was well-earned. She didn’t just tolerate humiliation—she relished it. Her favorite tactic was forcing students to strip down to their underwear—and sometimes further! And she didn’t bother hiding how much she enjoyed it. I saw her smirking more than once as a poor, squirming kid tried desperately to preserve a shred of dignity.

I had the pleasure (and yes, I mean that exactly how it sounds) of witnessing two of her depraved episodes. These two chapters are devoted to one of them.

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 tall, athletic, and slender—a striking brunette who could turn heads in the hallways, and often did. Boys noticed her. So did plenty of girls. Especially when she wore one of her tight-fitting sweaters, which she seemed to favor.

She had a small, slightly upturned nose—a feature I always found fitting. After all, she had a habit of turning that nose up at people like me. Anyone outside her carefully selected circle of friends, really. The kind of clique that carried itself as if it were just a little better than everyone else.

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 when Gertrude Farnsworth's desire to dole 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!" Farnsworth barked.

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?"

"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.

Farnsworth walked over with purpose. "Do you know the rules about gum, Miss Pennyfeather?"

"Yes, but..."

"Do you think you deserve to be punished?"

"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."

She fumbled in her bag and pulled out a mostly-full pack. Farnsworth took it, unwrapped a stick, and—without a word—popped it into her mouth. Then another. And another. Then the last one. 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..." Trudy stammered.

"Answer the question, Miss Pennyfeather."

"It’s...um...I guess it’s punishment that...shames people?"

"Very good. I’m glad you understand. Because you, Miss Pennyfeather, are about to be shamed. And when we’re done, I suspect you’ll never chew gum in my classroom again."

My heart picked up speed. Trudy's face had turned pale, and I'm sure her heart was also going at an accelerated pace.

"Spit it out."

Trudy complied, dropping her chewed gum into the teacher’s hand. Miss Farnsworth took the gum from her palm, stretched it out, and meticulously fixed it across the bridge of Trudy's upturned nose.

"You’ll leave that there the rest of the day."

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 own mouth and pulled out the enormous wad she’d been working on. Then she held it out in front of Trudy’s face.

"Open your mouth."

Trudy recoiled, horrified.

"Open it!" she bellowed, much more forcefully.

Trudy obeyed, trembling. Miss Farnsworth deposited the wad of gum onto her tongue.

Cries of "Eww!" echoed around the classroom. 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. Whether from shock or sheer refusal, she couldn't—or wouldn't—close it.

"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 in fascinated disgust as Trudy slowly did as she was told, forcing 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.

Without even turning around, Miss Farnsworth said, loud and clear, "Miss Pennyfeather, please remove your shoes and place them on my desk."

A ripple of amused whispers passed through the room.

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

"Showtime," giggled another.

Trudy’s eyes went wide. Either she’d never heard the stories—or she never thought they’d apply to her. 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 skin-tight jeans and a close-fitting lavender sweater. I wondered if she would be wearing them for much longer and smiled to myself.

Miss Farnsworth turned at her desk and faced the now-frozen Trudy. "Miss Pennyfeather. If your shoes aren’t on my desk in three seconds, you will be sorry. One..."

Trudy must have still been too dumbfounded to move.

"Two...."

Trudy kicked off her sandals and scrambled toward the desk.

"And, three," she said, while Trudy was only halfway to the desk, sandals in hand.

Trudy reluctantly laid her sandals on the desk and turned to walk away.

"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 flinched. She 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."

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—and yet, somehow, to everyone’s disbelief—Trudy Pennyfeather reached for the top button of her snug-fitting blue jeans. The room was silent, save for the soft, humiliated sniveling coming from the reluctant center of attention.

I watched eagerly as the shaken student undid the rest of the buttons and, with considerable effort, pushed her jeans down to her knees. A pair of black panties came into view. (They bore a striking resemblance, incidentally, to the pair 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 doubt it eased her embarrassment much. Her face, when I managed a glance, was flushed deep red. Her jeans, so tight to begin with, made everything worse—prolonging her task, and thus her embarrassment. She seemed to be in constant battle—one hand yanking her sweater downward, the other shoving at her jeans.

Eventually, she managed to wrestle them off completely and laid them across the desk. Like everyone else, I took a moment to size her up. She had long, shapely legs, with a tan line high on her thighs that faded into pale skin before meeting the black fabric of her panties.

She stood there with her back to us, still tugging at her sweater. 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 was waylaid again 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," she replied, letting her eyes travel deliberately over Trudy’s form. "You’re standing there, depantsed and barefoot in front of all of us. You have gum draped over your pretty little nose, and you’re chewing a fat wad of gum laced with my saliva. You’re blushing furiously, clearly 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 assessment hang in the air.

I couldn’t see Trudy’s face, but I was certain her blush deepened. She stood frozen, eyes downcast, fingers tugging compulsively at the hem of her sweater. That was about to change.

"Pull your sweater up above your navel," ordered Miss Farnsworth.

Trudy hesitated, then slowly complied, revealing the remainder of her panties and a few fresh inches of freshly bared skin. I doubt I was the only one in the room becoming a bit more stimulated.

"You may return to your seat," Miss Farnsworth said evenly.

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 far too late for sorries."

She strode briskly down the aisle and stopped behind Trudy’s chair. Without warning, she reached around and seized the hem of Trudy’s sweater with both hands.

"Arms up," she said coldly.

Trudy was unraveling. "Miss Farns—"

"ARMS UP!" she barked again—louder, sharper, leaving no room for hesitation.

Startled and panic-stricken, Trudy shot her arms into the air. Miss Farnsworth wasted no time. She seized the sweater and yanked it upward in one swift motion. Muffled, desperate yelps came from Trudy as the fabric passed over her face.

A 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. But it wasn’t just the view. It was the context. 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....
Last edited by Blondie on Sun Jul 13, 2025 12:18 am, edited 1 time in total.
User avatar
Blondie
Posts: 322
Joined: Tue May 16, 2023 7:09 pm
Has thanked: 151 times
Been thanked: 723 times
Contact:

Underpants Memoirs, Chapter 6 (ENF)

Post by Blondie »

Image

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.
User avatar
Jeepman89
Posts: 1366
Joined: Sat Oct 12, 2019 12:10 am
Has thanked: 3552 times
Been thanked: 1293 times
Contact:

Re: Underpants Memoirs

Post by Jeepman89 »

Shouldn't this be in the ENF section?
User avatar
Blondie
Posts: 322
Joined: Tue May 16, 2023 7:09 pm
Has thanked: 151 times
Been thanked: 723 times
Contact:

Re: Underpants Memoirs

Post by Blondie »

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.
User avatar
Jeepman89
Posts: 1366
Joined: Sat Oct 12, 2019 12:10 am
Has thanked: 3552 times
Been thanked: 1293 times
Contact:

Re: Underpants Memoirs

Post by Jeepman89 »

No worries. Thanks for clearing that up.
Post Reply

Who is online

Users browsing this forum: Ahrefs [Bot] and 7 guests