Chapter 5: The Humiliation of Trudy Pennyfeather, Part 1

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Status: In Progress  |  Genre: Humiliation Sex  |  House: Blondie's Humiliation Stories

Reads: 434

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 embarrassment.

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

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 up 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 of 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."

" 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 pretty 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, 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 back 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 pretty 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 very snug 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 of this book.) 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 "unmentionables" 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 of 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 you 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 have to admit that I couldn't take my eyes off of her. I watched delightedly as she squirmed in her seat.

After awhile 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, a matching bra and panties set.

For me, it was a sight to behold. Now, I'm not gay, or even bi, 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.....well, that put it over the top for me. be continued



Submitted: November 14, 2021

© Copyright 2021 Blondie2. All rights reserved.


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