Underpants Memoirs

Stories about girls getting pantsed, stripped and humiliated by anyone or anything.
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Blondie
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Underpants Memoirs

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Author's note: This is part of a multi-chapter story. The majority of the chapters contain ENM material, but this two-parter is for the ENF audience, so I thought I would duplicate the posting here. If interested, the entire story (so far) can be found here.

Chapter 5: The Humiliation of Trudy Pennyfeather, Part 1

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

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

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

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

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

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

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

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

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

"Are you chewing gum, Miss Pennyfeather?"

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

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

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

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

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

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

"Yes," she said.

"Let me have it."

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

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

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

"Answer the question, Miss Pennyfeather."

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

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

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

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

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

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

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

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

"Showtime," giggled another.

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

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

"Our" gum? She is such a devil.

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

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

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

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

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

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

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

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

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

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

"No, Miss Farnsworth."

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

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

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

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

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

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

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

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

To be continued....
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Re: Underpants Memoirs

Post by randomlygenerated »

The gum thing was not something that did it for me, but otherwise I liked it. I hope she loses her bra and panties and gets a spanking next!
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Re: Underpants Memoirs

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randomlygenerated wrote: Thu Aug 15, 2024 12:18 am The gum thing was not something that did it for me, but otherwise I liked it. I hope she loses her bra and panties and gets a spanking next!
Yeah, I went back and forth on the gum sequence, and decided to leave it in just to bring out the wickedness of Miss Farnsworth. But you're right—I could have left that out and it wouldn't have taken away from the story.
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Re: Underpants Memoirs

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Blondie wrote: Thu Aug 15, 2024 5:47 am
randomlygenerated wrote: Thu Aug 15, 2024 12:18 am The gum thing was not something that did it for me, but otherwise I liked it. I hope she loses her bra and panties and gets a spanking next!
Yeah, I went back and forth on the gum sequence, and decided to leave it in just to bring out the wickedness of Miss Farnsworth. But you're right—I could have left that out and it wouldn't have taken away from the story.
No I like it... it's not particulaly my thing but I think you need to mix it up when writing ENF stories and that will be an aspect that makes it stand out.
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Re: Underpants Memoirs

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SDS wrote: Thu Aug 15, 2024 9:25 am No I like it... it's not particulaly my thing but I think you need to mix it up when writing ENF stories and that will be an aspect that makes it stand out.
Yes, there is that. It's pretty hard to come up with something in this genre that hasn't been done before.
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Underpants Memoirs, Chapter 6

Post by Blondie »

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Chapter 6: The Humiliation of Trudy Pennyfeather, Part 2

As Trudy Pennyfeather squirmed in her seat, I found myself completely mesmerized. The sight of the mortified student stripped to her underwear was, quite frankly, pure eye candy. I’m sure the boys—hopped up on fifteen-year-old testosterone—were enjoying the spectacle even more than I was. 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 sat, in the middle of class, wearing nothing but a black bra and panties. Add to that the strip of gum stuck across the bridge of her nose, and the fact that she was being forced to chew a used wad that had come directly from the mouth of the diabolical Miss Farnsworth. It was almost too much. 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 happened during my freshman year. I was standing on the grass near the soccer field, chatting with a boy I had a bit of a crush on. I didn’t know Trudy Pennyfeather yet, but she was nearby with her usual clique of mean-girl friends. I was wearing a black elastic skirt and a cropped top that stopped just below my belly button.

Then, out of the blue, Trudy 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.

I scrambled up and gave chase, red-faced and humiliated, while Trudy and her friends played an impromptu game of keep-away with my skirt. Every time I got close, they tossed it to someone else, laughing hysterically. Eventually I managed to snatch it midair and yank it back on. 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—it felt like it was on fire.

I share that mortifying little tale with you so you’ll understand why, when Miss Farnsworth selected her victim that day, my enjoyment level was heightened considerably. Trudy Pennyfeather, after all, was getting her just comeuppance. And it was delicious.

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 were all 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.

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,” Trudy muttered quietly.

"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 frankly, it’s disrespectful.”

My eye candy became more delectable as the chagrined Trudy hesitated, then slowly turned to face us, her arms trembling as she lowered them to her sides. 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," Trudy stammered, her voice barely above a whisper.

“Good,” said Miss Farnsworth. “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?" she tried, though the answer clearly didn’t satisfy her interrogator.

“No,” Miss Farnsworth said. “I mean, what condition are you in right now that has rendered you shamefaced?”

"I...I'm in my underwear," mumbled the red-faced girl, her eyes glued to the floor.

"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 undies.”

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 undies.

Eventually, Miss Farnsworth gave the nod. “You may return to your seat, Miss Pennyfeather.”

Trudy didn’t need to be told twice. She scurried back, sliding into her seat and instantly curling forward again, arms tightly folded across her chest in a desperate bid to reclaim some sliver of modesty.

Meanwhile, Miss Farnsworth stood silently, eyes fixed on the thoroughly shamed Trudy. She looked contemplative, almost pensive—as if calculating her next move. After a while, I detected a slight, sinister smile creeping across 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 room, already buzzing with intrigue, grew even more electrified. I looked over at the horror-struck Trudy, then back to the twisted teacher. Whatever was coming next, I had a feeling it was going to be delicious.

“You see,” she continued, “I’ve been debating whether Miss Pennyfeather has been shamed enough—or whether additional discipline might be warranted. So I’ll let you decide. Please write your thoughts down. No need to sign them—your input will remain anonymous. However, they will be read aloud, so do try to mind your language.”

“You have several choices. You can say Miss Pennyfeather has endured enough and may get dressed immediately. Or you may suggest she remain in her underwear for the rest of class. Or, if you have another idea in mind—something more creative—you’re welcome to offer that as well.”

I looked over at Trudy and smiled. I knew right away that I was going to go with "something more creative." The possibilities were just too enticing.

“When you're finished,” she concluded, “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,” Miss Farnsworth said. “Would you be kind enough to collect the responses and bring them 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.

Still shielding herself slightly with crossed arms, she forced herself out of her seat. I watched, utterly enraptured, as she made her brisk, mortified march up and down the aisles—bare legs flashing, black underwear on display, collecting notes that might 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.

At one point, the flustered girl fumbled a sheet and let it slip to the floor, giving us a tasty moment as she bent to retrieve it. By the time she stood upright again, more blood had rushed to her head—and her face was as red as a ripe tomato.

At last, she approached the front, hands full of folded notes. Miss Farnsworth took them and casually shuffled the stack, then dropped them into a shallow cardboard box on her desk—right beside Trudy.

“Thank you 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 Farnsworth.

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 should get dressed immediately. :lol:

“Read it aloud, please,” Miss Farnsworth insisted.

Trudy mumbled something barely audible.

“Miss Pennyfeather, you need to speak clearly so we can all hear you. If I have to correct you again, there will be consequences.”

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

Trudy drew a shaky breath and finally read, "Miss Farnsworth should make her...make her take her bra off and let us see her...her titties."

There were gasps, then a ripple of giggles and gleeful snickers. Trudy's face turned even redder—no small feat, given how crimson she already was—as she stared miserably at the floor.

“Thank you,” Miss Farnsworth said briskly, taking the slip and placing 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’s a sampling 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’s clearly self-conscious about her breasts. A fitting punishment might be having her remove her bra and parade up and down the aisles with her hands behind her head.” Another big reaction, and I had to admit, the thought of it had me more than a little 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 of how to proceed."

Then she turned to Trudy. “You may return to your seat.”

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

None of them came from Trudy Pennyfeather.

She had stopped in her tracks and stood motionless for a moment, contemplating the newest indignity of her ongoing nightmare. For a moment, she simply stared ahead, unmoving—then slowly turned to face her nemesis.

“Please, Miss Farns...” she began, but her voice trailed off. She knew it was useless.

And then, to the absolute delight of her audience, Trudy reached behind her back and unclasped her bra. We drank in the sight of her bare back and watched in fascination as she slipped off her bra and gently laid it atop her growing pile of discarded clothes.

Trudy Pennyfeather was now topless. Our gleeful fascination stood in stark contrast to her sheer mortification. Her arms were clamped tightly across her bare chest as she turned and literally sprinted to her desk, nearly tripping into her seat, painfully aware that thirty pairs of eyes were locked 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 made a half-hearted show of studying trigonometry. Trudy, for her part, managed to open her book without uncovering her breasts, which she was shielding as best she could with both arms. I highly doubt that she digested one ounce of trigonometry in her wretched state.

As for me, I’ll admit I didn’t learn any more trig than she did that day. I couldn’t stop looking at her. I mean, she was practically naked, she had a beautiful body, and she was squirming with embarrassment. The situation was surreal. 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. Apparently, Trudy found my staring bothersome. I caught her glancing at me several times, clearly rattled, but I was undeterred in my fascination of her and her predicament. I was too mesmerized. Eventually, it must’ve pushed her over the edge, and she made a surprising and consequential mistake.

“Stop staring at me!” she whispered sharply.

Unfortunately for Trudy, it was loud enough to attract the attention of Miss Farnsworth.

“Miss Pennyfeather!” she bellowed, causing the startled Trudy to jump in her seat. “Why are you disturbing Michelle when she’s trying to study?”

"I...she wasn't studying," Trudy stammered. “She was...staring at me.”

“Come up here this instant, young lady,” Miss Farnsworth commanded.

Once more, Trudy made the humiliating walk to the front, arms still locked across her chest. She stopped at the front of Miss Farnsworth's desk and stood there submissively.

“Lean over,” Miss Farnsworth instructed. “Palms flat on my desk.”

Trudy obeyed. As she bent forward, I discreetly leaned to the side so I could see her tits hanging down. Others to my left and right had an even clearer angle—and none of them hesitated to take full advantage.

Miss Farnsworth opened her desk drawer, calmly retrieved a wooden paddle, and circled around to where Trudy stood trembling.

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 repeated, more firmly.

“Yes,” Trudy whispered.

“Yes, what?”

“Yes, I deserve a paddling,” she said meekly, eyes cast downward.

“How many swats do you think you deserve?”

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

“How many pieces of gum are stuck to your nose?” asked the teacher.

"Two," said Trudy quietly.

“And how many pieces of our gum do you have in your mouth?"

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

“Sounds like you’ve earned six of the best.”

Miss Farnsworth stepped to Trudy’s other side and took her stance, paddle in hand, as we watched with rapt attention.

“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 raised the paddle high in her right hand—then paused. Instead of striking, she set it down on the desk beside Trudy. Then, without a word, she moved behind the frightened girl and tugged her panties down to her knees, baring her soft, rounded bottom for the entire room.

Trudy yelped in shock, though the sound was nearly swallowed by the eruption of gasps and laughter from her highly entertained classmates. I had been watching closely—of course—and saw that her tush was twitching becomingly. The spectacle was, frankly, magnificent.

“I want you to count each one aloud, Miss Pennyfeather. And after every swat, you’ll say, ‘I’m sorry, Michelle.’”

I couldn't suppress a giggle. The whole scene was so delicious.

(I should note that Miss Farnsworth was well aware of the infamous de-skirting Trudy subjected me to the previous year. After I’d scrambled to pull my skirt back up, I distinctly remember anxiously scanning the crowd of grinning witnesses—and there she was, smiling along with the rest of them.)

The next sound we heard was a sharp, echoing THWAP! as the paddle smacked against Trudy’s left butt cheek.

"Oh! One...thank—I mean, I'm sorry, Michelle!"

Then came another THWAP!, as her right cheek was serviced accordingly.

“Two! I’m sorry, Michelle!”

THWAP!

“Three! I’m sorry, Michelle!”

THWAP!

“Four! I’m sorry, Michelle!”

Her cheeks were already beginning to flush, the pale skin turning a bright, telling 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 set the paddle gently on her desk. Trudy started to rise, but the teacher pressed a firm hand between her shoulder blades.

“Remain in position,” she instructed. “Your bottom is still blossoming into a nice shade of red, and I think your classmates would enjoy watching the full effect.”

As the color darkened from pink to something more vivid, I noticed with morbid fascination how her cheeks would occasionally clench—her muscles twitching involuntarily.

I slowly shook my head in wonder at the whole unbelievable scene.

Miss Farnsworth stepped behind Trudy again, her tone almost cheerful.

“Oh yes, they're turning such a pretty red,” she noted. “I imagine your bottom feels quite warm right now, doesn’t it, Miss Pennyfeather?”

“Y-Yes,” Trudy murmured faintly.

“Class, while we wait for Miss Pennyfeather’s bottom to reach its fullest shade of red—and I must say, it’s glowing rather nicely—we should take a moment to address the matter of her panties.”

A ripple of interest passed through the room. All eyes shifted—first from Trudy’s reddening backside, then to Miss Farnsworth’s face, and finally to the pair of panties bunched around Trudy’s knees, held aloft only by her slightly spread legs.

“I think it’s only fair we decide as a class how they should be dealt with going forward,” said Miss Farnsworth, her tone as composed as if she were taking lunch orders.

“Let’s start with a simple show of hands: How many of you would like Miss Pennyfeather’s panties pulled back up?”

Not surprisingly, only a couple of hands rose. Trudy remained frozen in place, her face no doubt burning even hotter than her rear.

“Hmm. Very well. Now—how many of you would prefer they stay just where they are?”

A good majority of the class raised their hands, mine included, mainly because we didn't realize there would be a third option.

“And lastly...how many of you would prefer Miss Pennyfeather’s panties be removed altogether?”

Every hand, save for the same two dissidents, shot up immediately.

There was no ambiguity now. Trudy’s fate had been sealed—by near-unanimous vote.

If Trudy had any doubt how the vote had gone—though I suspect she already knew—Miss Farnsworth ended her suspense straightaway. And as it turned out, I would be the benefactor, in more ways than one.

“Miss Pennyfeather, your classmates have spoken,” she announced, “and it’s clear they would like you to be naked.”

Trudy remained quiet, but the sudden, tight clench of her cheeks betrayed her anxiety.

“Michelle,” Miss Farnsworth said, turning toward me with a calm smile, “would you like to do the honors?”

"Certainly, Miss Farnsworth," I said as I blissfully sprang from my seat.

I practically floated to the front of the room, positioning myself behind the soon-to-be-nude Trudy. I was completely caught up in the moment, and I played my part to the hilt. Slowly, playfully, 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 toy with her nipples, causing her to flinch and let out a small yelp, much to my delight.

Then slowly, teasingly, I slid my fingers down her sides, caressing her skin tenderly and teasingly until I reached the waistband of her panties. She shivered at my touch, which only fueled my delight.

I slipped my fingers inside the waistband and began to draw the panties down—slowly, deliberately. My hands never lost contact with her skin as I inched the fabric lower, stretching out both the moment and the tension. When I finally pulled my hands free, the panties pooled neatly at her ankles.

I knelt and tapped the outside of her left ankle, a silent signal for her to lift her foot. She didn’t move. Without hesitation, I stood back up and gave her already-reddened ass cheeks two swift smacks with my open palm.

“Oh! Ow!” she yelped, her voice cracking with equal parts shame and surprise.

I knelt again and tapped her ankle. This time, she complied. I slipped the garment free from one foot, then tapped the other. After a brief hesitation, she lifted it—just enough to let me slide the panties free.

Trudy Pennyfeather was completely naked, and the realization thrilled me.

Grinning, I turned and held the panties aloft in both hands, proudly displaying them for all to see. The class responded with a gleeful uproar of cheers, laughter, and applause, furthering her already staggering humiliation.

For a final touch, I spread her panties out neatly on Miss Farnsworth’s desk, placing them directly beneath Trudy’s blushing face. She was still bent over, too stunned to move, her face burning with shame.

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, flushed with satisfaction.

“Very well, then,” said Miss Farnsworth. “Miss Pennyfeather, you may return to your seat."

Trudy reached instinctively for her panties, then stopped herself—wisely, all things considered. Arms crossed in a frantic effort to shield herself, she turned and made the short, humiliating walk back to her desk, a couple of tears slipping down her burning cheeks.

I had gotten my wish. Trudy Pennyfeather was sitting at her desk, completely naked, for our entertainment.

Her discomfort was delicious. 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, trying to shield herself like her life depended on it. Every so often, 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 final time, adding just a touch more spice to an already unforgettable moment.

“Miss Pennyfeather, would you please stand up?”

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 gaze fixed to her bare toes.

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

"Um...because...I'm...I'm naked."

The class giggled again. 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 by her desk for the remainder of the period. I kept hoping Miss Farnsworth would make her do something else, like walk up and down the aisles, 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 the teacher’s desk at the end of class, Trudy was hastily throwing her clothes back on, her face still burning. 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.
Last edited by Blondie on Wed Jul 16, 2025 2:23 am, edited 1 time in total.
randomlygenerated
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Re: Underpants Memoirs

Post by randomlygenerated »

So no more parts with girls?
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Blondie
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Re: Underpants Memoirs

Post by Blondie »

randomlygenerated wrote: Fri Aug 23, 2024 6:55 am So no more parts with girls?
None that I've written so far, but it's an ongoing story, so there is potential for more ENF down the road.
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Re: Underpants Memoirs

Post by skillbox »

I’d love to see that potential used for either the author of this story or Felicity! :D
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