Underpants Memoirs
Posted: Wed May 29, 2024 9:07 pm
The following is applicable to all chapters of “Underpants Memoirs:”
© September 2019 by Blondie
This is a work of fiction and is pure fantasy. Names, characters, places, and incidents are products of the author’s imagination and are used fictitiously. Any resemblance to actual events, 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

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.
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 kind of 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.
© September 2019 by Blondie
This is a work of fiction and is pure fantasy. Names, characters, places, and incidents are products of the author’s imagination and are used fictitiously. Any resemblance to actual events, 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
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.
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 kind of 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.
