Roosevelt Humiliations
Posted: Sat Jan 06, 2024 3:01 am
The following is applicable to all chapters of “Roosevelt Humiliations:”
© May 2004 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: The Wedgie
Chapter 2: Pantsless in Homeroom
Chapter 3: Stripped in the Car
Chapter 4: The Naked Crawl
Chapter 5: Bus Stop Humiliation
Chapter 6: Naked and Molested in the Auditorium
Chapter 7: Brenda's Revenge
Chapter 8: Classroom Humiliation
Chapter 9: Stripped on the Soccer Field
Chapter 10: Forced Naked at a Public Beach
Chapter 11: Maternal Discipline
Chapter 12: A Very Embarrassing Spanking
Chapter 13: Under My Sister's Control
Chapter 14: Victoria's Secret
Chapter 15: A Mortifying Measurement
Chapter 16: Tormented by Becky and Brenda
Chapter 17: The Bubble Bath
Chapter 18: Spanked and Pantied
Chapter 19: The Slumber Party Begins
Chapter 20: Petticoated
Chapter 21: Felicity
Chapter 22: Denuded by a Thirteen-Year-Old
Chapter 23: Shake That Ass!
Chapter 24: Hairlessness Revealed
Chapter 25: Shrinkage
Chapter 26: Forced Orgasm
Author's Note: In Chapter 13 there is a scene where Becky stops at Brenda's house to pick her up on the way to the mall. She makes Blondie ring the doorbell, and Brenda's mother answers. She is quite intrigued—and amused—by Blondie's attire, which consisted partly of short shorts, frilly socks and Becky's tennis shoes. I always thought I could do more with that scene, so some fifteen years later I sat down and started writing a modification to that scene, and proceeded to get completely carried away. Long story short, Blondie ends up being thoroughly humiliated by a few of Brenda's mother's friends that were there for a tea party.
The "modification" turned into a five-chapter story of its own. If you are interested in checking it out, you can find it here: Roosevelt Humiliation: The Missing Chapters

Chapter 1: The Wedgie
Intro
It was my first week at Roosevelt High School, and I was scared. I had heard stories about how the smaller kids were tormented by the bigger ones. Unfortunately, I was one of the smaller kids. Standing at only five feet, four inches and weighing just one hundred and seventeen pounds dripping wet, I knew I was an easy target.
I had already seen some of the older, bigger students, and maybe it was just my imagination, but I felt like they were sizing me up, their amused smirks making me uneasy. Whenever I caught one looking at me, I found myself walking a little faster, my heart pounding.
And sure enough, my time would come
My Humiliation Begins
It was lunchtime on Friday, and I was standing by myself watching a group of kids play baseball. The week was almost over, and so far I had escaped unscathed, so I was thinking that maybe those stories are just unfounded rumors.
I was starting to feel a little more comfortable with that thought when out of the corner of my eye I noticed someone kneeling on his hands and knees right behind me. Before I had time to react, another student pushed me backward by the shoulders and I fell to the ground.
That was when I made a fateful mistake that probably went a long way toward inviting future torment. Without thinking, I vented my anger by getting up and kicking dirt on the guy who was on his hands and knees.
He at first had an incredulous look on his face, probably because a little freshman like me had dared to lash back.
That look was instantly replaced by one of anger, and the next thing I knew, he grabbed my ankles and hauled me back down to the ground, saying to his friend, “Come on, Reggie, let's teach this little shit a lesson.”
Struggle as I might, I couldn’t fight off the two attackers, as they were almost twice my size. I felt my shirttail lifting out of the back and then felt fingers reaching inside the back of my pants.
My white briefs were then pulled violently up my back. I was on my knees while the guy called Reggie held me in a headlock. The other attacker straddled my neck, facing toward his objective while pulling my underpants up my back.
"No! Please! I'm sorry!" I screamed, attracting more attention, as the baseball players stopped their game and were looking on in amusement.
Before I knew it, the leg holes of my underpants were completely outside of my pants.
Reggie’s friend was relentless. He grabbed the leg holes and pulled even harder. My balls were starting to hurt from the pressure when the unmistakable sound of ripping fabric could be heard. He kept pulling and before long my underpants were ripped completely off.
He then took my torn underpants and wrapped them around my neck, tying them in a knot.
They both got up, full of themselves from their accomplishment. My main attacker addressed me. “What the fuck were you thinking, you little shit?” he said. “Nobody fucks with Mitch, especially a freshman. What’s your name?”
I gave him my nickname without thinking, which I immediately regretted.
“Blondie,” I answered tearfully.
Mitch's grin widened. “Blondie, huh?” He chuckled, shaking his head. “Well, Blondie, you and I are gonna get to know each other real well.” He turned to Reggie and added with a glint in his eye, “I think we’ve found ourselves our freshman plaything.”
Reggie looked me up and down, his smirk matching Mitch’s. “Yeah, we’ll have some fun with him, alright.”
My face burned as they walked away, their laughter lingering in the air..
Mitch glanced back over his shoulder. “Watch your back, Blondie. I’ll probably be there.”
Recovery
I had to put my worries about Mitch aside, as I had more immediate concerns. I tugged at the underpants wrapped around my neck, but the knot was very tight.
I looked up and noticed quite a few people staring at me, including a group of about five girls who were giggling freely.
I felt my face turning bright red as I sat on the ground and struggled with the knot. After a couple of agonizing minutes, a compassionate fellow freshman came to my rescue.
“Here, let me help you with that,” he said as he took two hands and tore the underpants from my neck.
“Thanks a lot,” I told him gratefully.
“No problem. My name’s Robert, what’s yours?”
“Most people call me Blondie.”
“I can see why,” he said with a grin, eyeing my shock of light blond hair. “A pretty unnerving experience, huh?”
“Yeah. I’ve heard about this place—I should have known better. I was an idiot for fighting back.”
“You’d better be careful, Blondie,” Robert warned. “From what I hear, next time they’re liable to take off your pants.”
“Oh, God,” I muttered, literally quivering at the thought. “Seriously?”
“Yeah. I don’t mean to scare you, but my brother is a senior here, and he's told me a few stories. For instance, last year they stripped a freshman completely naked and greased him from head to toe with baby oil. Then they took turns sliding him down a newly waxed hallway. They made bets on how far the poor kid would slide. A crowd started gathering and they were making bets, too. Supposedly, the winning bet was forty-seven yards. Every time he got up, he just kept slipping all over the place. Can you imagine the humiliation?”
“Oh, God,” was all I could say.
“The scary thing is,” Robert continued, “when these guys got caught, they got in trouble—not for stripping and humiliating the freshman, but for greasing up the hallway.”
“Oh, man,” I groaned. “Why don’t the teachers do something about it?”
“Well, I’ll tell you,” Robert said. “A couple of years ago, a bunch of seniors stripped a freshman near the football field. They made him walk naked the full length of the field with his hands behind his head.”
"Oh, shit," I said.
“Yeah. One of the teachers—a woman—reported the incident to the principal. He had to act on it, and there was a full investigation. One guy already had a history, and he was expelled. Three others got suspended.”
“That’s a good thing,” I said, hopefully.
“Well, here’s the deal,” Robert continued. “The guy who got expelled was out for vengeance, and his three friends felt the same way.”
“Uh-oh,” I said.
"Uh-oh is right. They stalked the female teacher, and about a month after the incident she was attacked."
"Oh, jeez, what did they do?"
"Well, she wasn't physically harmed, but I guarantee you there are emotional scars. She was working late in her classroom after school one day, and they burst in, ganged up on her and stripped her naked."
“Whoa,” I murmured, wide-eyed.
"They tied her up with rope from a fixture on the ceiling, then took pictures. They told her that if she ever told anyone who did it, they would release the pictures, and that she could expect much worse—and that they knew where she lived."
"Holy shit!"
"They left her tied up there with the door open. At some point a couple of students saw her from the hallway and rescued her. Word got around the school quickly, including to the faculty.
“She never gave them up, but everyone had a pretty good idea who did it and why. In any case, the boys got off scot-free. Ever since then, the teachers turn a blind eye when anything like what happened to you today—or worse—takes place.”
“Oh, God. Um, which teacher was it?”
“Her name was Miss Hartford. She’s not here anymore. She took a leave of absence and never came back. I’m guessing she left town. I mean, can you blame her?”
“No, I guess not,” I said, shaking my head.
“And there’s more,” Robert went on. “It involves Mr. Radcliffe—he was the principal then—and still is. My brother never got the full story of how they got to him. More naked pictures? He’s not a big guy, so they could have easily overpowered him if they wanted to. In any case, about a week after Miss Hartford’s naked episode, Mr. Radcliffe reinstated the guy who was expelled.”
"Jeez, that's crazy."
“And just to show that they had free rein to do whatever they wanted, they found that same freshman—he helped with the investigation, so they weren’t happy with him—and they stripped him naked and made him walk the length of the football field again. This time, they didn’t give him back his clothes.”
“Holy shit!” I said. “What did the kid do?”
“I don’t know how he finally got some clothes, but he had to go back into the building naked. I’m sure it was a very humiliating experience.”
“Oh, man,” was all I could say as I imagined myself in the same position as that unfortunate freshman.
“Anyway,” Robert sighed, “watch yourself, Blondie. The inmates are running the asylum here.”
The warning bell sounded, and Robert and I went our separate ways. As I tried to shake off my awful experience and Robert’s harrowing stories, I shuddered at what might lie in store for me in my future at Roosevelt High.
© May 2004 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: The Wedgie
Chapter 2: Pantsless in Homeroom
Chapter 3: Stripped in the Car
Chapter 4: The Naked Crawl
Chapter 5: Bus Stop Humiliation
Chapter 6: Naked and Molested in the Auditorium
Chapter 7: Brenda's Revenge
Chapter 8: Classroom Humiliation
Chapter 9: Stripped on the Soccer Field
Chapter 10: Forced Naked at a Public Beach
Chapter 11: Maternal Discipline
Chapter 12: A Very Embarrassing Spanking
Chapter 13: Under My Sister's Control
Chapter 14: Victoria's Secret
Chapter 15: A Mortifying Measurement
Chapter 16: Tormented by Becky and Brenda
Chapter 17: The Bubble Bath
Chapter 18: Spanked and Pantied
Chapter 19: The Slumber Party Begins
Chapter 20: Petticoated
Chapter 21: Felicity
Chapter 22: Denuded by a Thirteen-Year-Old
Chapter 23: Shake That Ass!
Chapter 24: Hairlessness Revealed
Chapter 25: Shrinkage
Chapter 26: Forced Orgasm
Author's Note: In Chapter 13 there is a scene where Becky stops at Brenda's house to pick her up on the way to the mall. She makes Blondie ring the doorbell, and Brenda's mother answers. She is quite intrigued—and amused—by Blondie's attire, which consisted partly of short shorts, frilly socks and Becky's tennis shoes. I always thought I could do more with that scene, so some fifteen years later I sat down and started writing a modification to that scene, and proceeded to get completely carried away. Long story short, Blondie ends up being thoroughly humiliated by a few of Brenda's mother's friends that were there for a tea party.
The "modification" turned into a five-chapter story of its own. If you are interested in checking it out, you can find it here: Roosevelt Humiliation: The Missing Chapters

Chapter 1: The Wedgie
Intro
It was my first week at Roosevelt High School, and I was scared. I had heard stories about how the smaller kids were tormented by the bigger ones. Unfortunately, I was one of the smaller kids. Standing at only five feet, four inches and weighing just one hundred and seventeen pounds dripping wet, I knew I was an easy target.
I had already seen some of the older, bigger students, and maybe it was just my imagination, but I felt like they were sizing me up, their amused smirks making me uneasy. Whenever I caught one looking at me, I found myself walking a little faster, my heart pounding.
And sure enough, my time would come
My Humiliation Begins
It was lunchtime on Friday, and I was standing by myself watching a group of kids play baseball. The week was almost over, and so far I had escaped unscathed, so I was thinking that maybe those stories are just unfounded rumors.
I was starting to feel a little more comfortable with that thought when out of the corner of my eye I noticed someone kneeling on his hands and knees right behind me. Before I had time to react, another student pushed me backward by the shoulders and I fell to the ground.
That was when I made a fateful mistake that probably went a long way toward inviting future torment. Without thinking, I vented my anger by getting up and kicking dirt on the guy who was on his hands and knees.
He at first had an incredulous look on his face, probably because a little freshman like me had dared to lash back.
That look was instantly replaced by one of anger, and the next thing I knew, he grabbed my ankles and hauled me back down to the ground, saying to his friend, “Come on, Reggie, let's teach this little shit a lesson.”
Struggle as I might, I couldn’t fight off the two attackers, as they were almost twice my size. I felt my shirttail lifting out of the back and then felt fingers reaching inside the back of my pants.
My white briefs were then pulled violently up my back. I was on my knees while the guy called Reggie held me in a headlock. The other attacker straddled my neck, facing toward his objective while pulling my underpants up my back.
"No! Please! I'm sorry!" I screamed, attracting more attention, as the baseball players stopped their game and were looking on in amusement.
Before I knew it, the leg holes of my underpants were completely outside of my pants.
Reggie’s friend was relentless. He grabbed the leg holes and pulled even harder. My balls were starting to hurt from the pressure when the unmistakable sound of ripping fabric could be heard. He kept pulling and before long my underpants were ripped completely off.
He then took my torn underpants and wrapped them around my neck, tying them in a knot.
They both got up, full of themselves from their accomplishment. My main attacker addressed me. “What the fuck were you thinking, you little shit?” he said. “Nobody fucks with Mitch, especially a freshman. What’s your name?”
I gave him my nickname without thinking, which I immediately regretted.
“Blondie,” I answered tearfully.
Mitch's grin widened. “Blondie, huh?” He chuckled, shaking his head. “Well, Blondie, you and I are gonna get to know each other real well.” He turned to Reggie and added with a glint in his eye, “I think we’ve found ourselves our freshman plaything.”
Reggie looked me up and down, his smirk matching Mitch’s. “Yeah, we’ll have some fun with him, alright.”
My face burned as they walked away, their laughter lingering in the air..
Mitch glanced back over his shoulder. “Watch your back, Blondie. I’ll probably be there.”
Recovery
I had to put my worries about Mitch aside, as I had more immediate concerns. I tugged at the underpants wrapped around my neck, but the knot was very tight.
I looked up and noticed quite a few people staring at me, including a group of about five girls who were giggling freely.
I felt my face turning bright red as I sat on the ground and struggled with the knot. After a couple of agonizing minutes, a compassionate fellow freshman came to my rescue.
“Here, let me help you with that,” he said as he took two hands and tore the underpants from my neck.
“Thanks a lot,” I told him gratefully.
“No problem. My name’s Robert, what’s yours?”
“Most people call me Blondie.”
“I can see why,” he said with a grin, eyeing my shock of light blond hair. “A pretty unnerving experience, huh?”
“Yeah. I’ve heard about this place—I should have known better. I was an idiot for fighting back.”
“You’d better be careful, Blondie,” Robert warned. “From what I hear, next time they’re liable to take off your pants.”
“Oh, God,” I muttered, literally quivering at the thought. “Seriously?”
“Yeah. I don’t mean to scare you, but my brother is a senior here, and he's told me a few stories. For instance, last year they stripped a freshman completely naked and greased him from head to toe with baby oil. Then they took turns sliding him down a newly waxed hallway. They made bets on how far the poor kid would slide. A crowd started gathering and they were making bets, too. Supposedly, the winning bet was forty-seven yards. Every time he got up, he just kept slipping all over the place. Can you imagine the humiliation?”
“Oh, God,” was all I could say.
“The scary thing is,” Robert continued, “when these guys got caught, they got in trouble—not for stripping and humiliating the freshman, but for greasing up the hallway.”
“Oh, man,” I groaned. “Why don’t the teachers do something about it?”
“Well, I’ll tell you,” Robert said. “A couple of years ago, a bunch of seniors stripped a freshman near the football field. They made him walk naked the full length of the field with his hands behind his head.”
"Oh, shit," I said.
“Yeah. One of the teachers—a woman—reported the incident to the principal. He had to act on it, and there was a full investigation. One guy already had a history, and he was expelled. Three others got suspended.”
“That’s a good thing,” I said, hopefully.
“Well, here’s the deal,” Robert continued. “The guy who got expelled was out for vengeance, and his three friends felt the same way.”
“Uh-oh,” I said.
"Uh-oh is right. They stalked the female teacher, and about a month after the incident she was attacked."
"Oh, jeez, what did they do?"
"Well, she wasn't physically harmed, but I guarantee you there are emotional scars. She was working late in her classroom after school one day, and they burst in, ganged up on her and stripped her naked."
“Whoa,” I murmured, wide-eyed.
"They tied her up with rope from a fixture on the ceiling, then took pictures. They told her that if she ever told anyone who did it, they would release the pictures, and that she could expect much worse—and that they knew where she lived."
"Holy shit!"
"They left her tied up there with the door open. At some point a couple of students saw her from the hallway and rescued her. Word got around the school quickly, including to the faculty.
“She never gave them up, but everyone had a pretty good idea who did it and why. In any case, the boys got off scot-free. Ever since then, the teachers turn a blind eye when anything like what happened to you today—or worse—takes place.”
“Oh, God. Um, which teacher was it?”
“Her name was Miss Hartford. She’s not here anymore. She took a leave of absence and never came back. I’m guessing she left town. I mean, can you blame her?”
“No, I guess not,” I said, shaking my head.
“And there’s more,” Robert went on. “It involves Mr. Radcliffe—he was the principal then—and still is. My brother never got the full story of how they got to him. More naked pictures? He’s not a big guy, so they could have easily overpowered him if they wanted to. In any case, about a week after Miss Hartford’s naked episode, Mr. Radcliffe reinstated the guy who was expelled.”
"Jeez, that's crazy."
“And just to show that they had free rein to do whatever they wanted, they found that same freshman—he helped with the investigation, so they weren’t happy with him—and they stripped him naked and made him walk the length of the football field again. This time, they didn’t give him back his clothes.”
“Holy shit!” I said. “What did the kid do?”
“I don’t know how he finally got some clothes, but he had to go back into the building naked. I’m sure it was a very humiliating experience.”
“Oh, man,” was all I could say as I imagined myself in the same position as that unfortunate freshman.
“Anyway,” Robert sighed, “watch yourself, Blondie. The inmates are running the asylum here.”
The warning bell sounded, and Robert and I went our separate ways. As I tried to shake off my awful experience and Robert’s harrowing stories, I shuddered at what might lie in store for me in my future at Roosevelt High.