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 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

Chapter 1: Introduction to Roosevelt High
Hi, my name is Michelle, and I graduated from Roosevelt High School a few years ago. I'm telling you this because Roosevelt High was (and probably still is) a school like no other. I know every school has their share of the occasional hazings and bullying, and that the older kids sometimes pick on the incoming freshmen. But at Roosevelt it was taken to a whole different level.
Make that a whole different stratosphere. It seemed like at least once a week—and sometimes more—some poor kid was having some (and sometimes all!) of their clothing forcibly removed, much to their extreme embarrassment. I have to say that the amount of strippings and humiliations that took take place during my four years there were mind-boggling.
Don't get me wrong—I absolutely loved being part of that culture. One never knew when the next sighting of a frantic freshman fighting to keep his clothes on would arise. And when it did, I must admit that I found it quite titillating, as it seemingly was for most of my fellow students. And to this day I derive considerable pleasure when I reflect on the sordid events that took place during my time in the hallowed halls of Roosevelt High. Which is why I'm writing these memoirs. I think it will be enjoyable to chronicle some of the various depantsings and humiliations that I either participated in, witnessed, or heard about during my four years in high school.
The ability to recount these events recently became more doable, as a few months ago I attended our 5-year reunion. Inevitably—and it didn't take long—the conversation revolved around the many accounts of the assorted humiliations that took place while we were there. In fact, it is fair to say that most of my time that night was joyously spent relating and listening to all the stories, most of which were told in detail. Some of them I had witnessed, but there were many that I had not been aware of, so it was a very stimulating evening for me, to say the least.
At some point early on I got the bright idea that it might be an interesting endeavor to pass along the accounts of some of these events in the form of a memoir. So I actually started writing down some of the specifics as they were detailed. I have a pretty good memory, but while writing this I'll probably refer to the notes that I jotted down on several cocktail napkins. These notes (and the detail that the narrators went into) should enable me to tell the tales in storybook fashion, which hopefully will be enjoyable for the reader—and for me.
Before I close this intro and move on to a stripping tale, I feel I should touch on the fact that there was little intervention—if any—by the adults in the room. Early in my freshman year when I witnessed a boy being depantsed, I was absolutely astounded when I watched three different teachers turn the other way while the strippings were transpiring. I later found out why.
Legend has it that the year before a bunch of seniors stripped a freshman boy completely naked, then made him walk the length of the football field. (I'm sorry I missed that one!) A female teacher reported the incident to the principal, so he felt obligated to act on it. After an investigation, some boys were suspended, and the main instigator was expelled.
About a week later the teacher was working late in her classroom and those same boys entered the room, held her down and stripped her naked. They tied her up with her arms above her head and took pictures. They told her she better not divulge their names, or they would release the pictures, and that they knew where she lived. They left her tied up there with the door open, and at some point a couple of students rescued her. Word got out to the rest of the faculty about her stripping. The teacher never gave up the names, but everyone knew who did it and why they did it.
For good measure, that same day they stalked the principal, a smallish man by the name of Jerry Radcliffe. As he was getting out of his car in front of his house they grabbed him and threw him in the back seat of their car. About two hours later they let him out of the car a couple of blocks from his house. He was stark naked, and only he and the perps know exactly what they did to him (or made him do).
In any case, the expelled student was reinstated the next day, and from that day forward the faculty members turned a blind eye to the humiliations that were doled out over my four years at Roosevelt High.
And, of course, no student would dare report these incidents to any authorities, as they are fearful (and rightfully so) of very humiliating consequences.
Oh, and there is one more matter to weigh in on before closing. You may be wondering why I have entitled these accounts "Underpants Memoirs." After all, out of all the depantsings that I'm aware of, I'd say almost half of them resulted in the victim being stripped completely naked. That was always a turn-on for me, but I must admit that I have a soft spot—a fascination may be a better way to put it—for watching a poor, frenzied freshman getting stripped down to his tighty-whities. For whatever reason, the choice of underwear for the smaller freshmen were almost always (much to my stimulation) the small white briefs, or more popularly known as tighty-whities, which will be the term of choice in these memoirs.
And, by the way, the victim of these strippings invariably was a freshman. I guess it was easier to pick on the smaller kids. Over the years the only exception I saw was this kid that went by the name of Blondie. He graduated the same year that I did, and I witnessed him being stripped right up to his senior year. And to make it even more embarrassing for him, it was his sister and her friends that were antagonizing him during his first three years there. Most boy strippings at Roosevelt were carried out by other boys, but that wasn't the case with this Blondie guy. Then, there was a girl named Felicity who must have really had something over on him. During his senior year she made him keep his body completely hairless and he had to wear these short shorts to school. It must have been really embarrassing for him to have to show off his clean-shaven legs like that to the whole school every day. Oh, and Felicity was a freshman at the time. Can you believe it?
Anyway, I'll have to use at least one of my chapters to tell you about one or more of Blondie's strippings that I happened to witness. He had a smaller than average size penis, and without the hair it looked like a freshman's dick (or maybe more like an elementary school kid's dick), and the sight of it made me giggle. And this Felicity girl really had a knack for ratcheting up his humiliation. I remember, much to my entertainment, him being stripped to his tighty-whities right at his locker. I guess at some point Felicity had other ideas, because one day I saw her make him drop his pants in the courtyard, and the poor boy was wearing a pair of panties—which, in conjunction with his hairless legs made him look quite feminine, indeed. I got a pretty good laugh out of that, not to mention a bit of a sexual arousal over his humiliation.
Speaking of panties, you've probably noticed that I did include a picture of a pair of panties on the cover of these memoirs. That's because, though probably over 90% of the strippings were administered to a boy, there was the occasional stripping of a female. In those cases, she usually wasn't stripped naked (though I know of two occasions when she was), but was stripped to her bra and panties, or on occasion, all the way down to her panties.
But I don't want to give too much away so early. I hope you'll stay tuned for my future chapters, which I'll add here as time permits.
© 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

Chapter 1: Introduction to Roosevelt High
Hi, my name is Michelle, and I graduated from Roosevelt High School a few years ago. I'm telling you this because Roosevelt High was (and probably still is) a school like no other. I know every school has their share of the occasional hazings and bullying, and that the older kids sometimes pick on the incoming freshmen. But at Roosevelt it was taken to a whole different level.
Make that a whole different stratosphere. It seemed like at least once a week—and sometimes more—some poor kid was having some (and sometimes all!) of their clothing forcibly removed, much to their extreme embarrassment. I have to say that the amount of strippings and humiliations that took take place during my four years there were mind-boggling.
Don't get me wrong—I absolutely loved being part of that culture. One never knew when the next sighting of a frantic freshman fighting to keep his clothes on would arise. And when it did, I must admit that I found it quite titillating, as it seemingly was for most of my fellow students. And to this day I derive considerable pleasure when I reflect on the sordid events that took place during my time in the hallowed halls of Roosevelt High. Which is why I'm writing these memoirs. I think it will be enjoyable to chronicle some of the various depantsings and humiliations that I either participated in, witnessed, or heard about during my four years in high school.
The ability to recount these events recently became more doable, as a few months ago I attended our 5-year reunion. Inevitably—and it didn't take long—the conversation revolved around the many accounts of the assorted humiliations that took place while we were there. In fact, it is fair to say that most of my time that night was joyously spent relating and listening to all the stories, most of which were told in detail. Some of them I had witnessed, but there were many that I had not been aware of, so it was a very stimulating evening for me, to say the least.
At some point early on I got the bright idea that it might be an interesting endeavor to pass along the accounts of some of these events in the form of a memoir. So I actually started writing down some of the specifics as they were detailed. I have a pretty good memory, but while writing this I'll probably refer to the notes that I jotted down on several cocktail napkins. These notes (and the detail that the narrators went into) should enable me to tell the tales in storybook fashion, which hopefully will be enjoyable for the reader—and for me.

Before I close this intro and move on to a stripping tale, I feel I should touch on the fact that there was little intervention—if any—by the adults in the room. Early in my freshman year when I witnessed a boy being depantsed, I was absolutely astounded when I watched three different teachers turn the other way while the strippings were transpiring. I later found out why.
Legend has it that the year before a bunch of seniors stripped a freshman boy completely naked, then made him walk the length of the football field. (I'm sorry I missed that one!) A female teacher reported the incident to the principal, so he felt obligated to act on it. After an investigation, some boys were suspended, and the main instigator was expelled.
About a week later the teacher was working late in her classroom and those same boys entered the room, held her down and stripped her naked. They tied her up with her arms above her head and took pictures. They told her she better not divulge their names, or they would release the pictures, and that they knew where she lived. They left her tied up there with the door open, and at some point a couple of students rescued her. Word got out to the rest of the faculty about her stripping. The teacher never gave up the names, but everyone knew who did it and why they did it.
For good measure, that same day they stalked the principal, a smallish man by the name of Jerry Radcliffe. As he was getting out of his car in front of his house they grabbed him and threw him in the back seat of their car. About two hours later they let him out of the car a couple of blocks from his house. He was stark naked, and only he and the perps know exactly what they did to him (or made him do).
In any case, the expelled student was reinstated the next day, and from that day forward the faculty members turned a blind eye to the humiliations that were doled out over my four years at Roosevelt High.
And, of course, no student would dare report these incidents to any authorities, as they are fearful (and rightfully so) of very humiliating consequences.
Oh, and there is one more matter to weigh in on before closing. You may be wondering why I have entitled these accounts "Underpants Memoirs." After all, out of all the depantsings that I'm aware of, I'd say almost half of them resulted in the victim being stripped completely naked. That was always a turn-on for me, but I must admit that I have a soft spot—a fascination may be a better way to put it—for watching a poor, frenzied freshman getting stripped down to his tighty-whities. For whatever reason, the choice of underwear for the smaller freshmen were almost always (much to my stimulation) the small white briefs, or more popularly known as tighty-whities, which will be the term of choice in these memoirs.
And, by the way, the victim of these strippings invariably was a freshman. I guess it was easier to pick on the smaller kids. Over the years the only exception I saw was this kid that went by the name of Blondie. He graduated the same year that I did, and I witnessed him being stripped right up to his senior year. And to make it even more embarrassing for him, it was his sister and her friends that were antagonizing him during his first three years there. Most boy strippings at Roosevelt were carried out by other boys, but that wasn't the case with this Blondie guy. Then, there was a girl named Felicity who must have really had something over on him. During his senior year she made him keep his body completely hairless and he had to wear these short shorts to school. It must have been really embarrassing for him to have to show off his clean-shaven legs like that to the whole school every day. Oh, and Felicity was a freshman at the time. Can you believe it?
Anyway, I'll have to use at least one of my chapters to tell you about one or more of Blondie's strippings that I happened to witness. He had a smaller than average size penis, and without the hair it looked like a freshman's dick (or maybe more like an elementary school kid's dick), and the sight of it made me giggle. And this Felicity girl really had a knack for ratcheting up his humiliation. I remember, much to my entertainment, him being stripped to his tighty-whities right at his locker. I guess at some point Felicity had other ideas, because one day I saw her make him drop his pants in the courtyard, and the poor boy was wearing a pair of panties—which, in conjunction with his hairless legs made him look quite feminine, indeed. I got a pretty good laugh out of that, not to mention a bit of a sexual arousal over his humiliation.
Speaking of panties, you've probably noticed that I did include a picture of a pair of panties on the cover of these memoirs. That's because, though probably over 90% of the strippings were administered to a boy, there was the occasional stripping of a female. In those cases, she usually wasn't stripped naked (though I know of two occasions when she was), but was stripped to her bra and panties, or on occasion, all the way down to her panties.
But I don't want to give too much away so early. I hope you'll stay tuned for my future chapters, which I'll add here as time permits.