Roosevelt Humiliations

Stories about boys ending up in compromising situations, preferably naked and embarrassed, as the name suggests.
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Roosevelt Humiliations, Chapter 7

Post by Blondie »

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Chapter 7: Brenda's Revenge

Payback

Unfortunately, I have yet another humiliation to recount. This one took place on the penultimate day of my sophomore year, courtesy of my new nemesis, Brenda—who, with the help of a few friends, made sure I paid dearly for my mistake.

As you may recall, Brenda is in my homeroom. She was the one who planted my underwear on my desk following my staggering humiliation in the auditorium. Since then, she had made it her mission to tease me about that mortifying ordeal at every opportunity. It had gotten to the point where all she had to do was slowly run her eyes up and down my body—peeling away my clothes with her eyes—before flashing a knowing grin. Without fail, my face would turn bright red, much to her delight.

After enduring several of these embarrassing encounters, I resolved to exact revenge. The payback was sweet while it lasted, but I'm sorry to say that ultimately, I paid dearly for it.

Three days before the end of the school year, I put my plan into action. You see, Brenda happens to have very small breasts, and I figured that must be a source of insecurity for her. So, in my infinite wisdom, I decided to exploit this probable source of embarrassment. That morning, I arrived at school early, making sure I was the first one in homeroom. Seizing the opportunity, I strode up to the chalkboard and, in large capital letters, wrote:

BRENDA HOLLISTER HAS TINY LITTLE TITTIES.

Smiling to myself, I dusted my hands off, admiring my handiwork. Oh, this was going to be good. This was going to be very good indeed.

To avoid suspicion, I stepped out into the hallway and waited for Brenda to arrive. The plan was simple: casually walk in beside her, act completely innocent, and bask in her embarrassment.

“Hi, Blondie,” she greeted me with a smirk the moment she spotted me. As always, her eyes flickered down to my crotch—just long enough to make me squirm—before locking onto mine with that knowing grin. Satisfied with the inevitable rush of color to my cheeks, she let out a soft giggle, turned, and walked into the room. I followed her in, anxiously anticipating the next few moments.

The classroom was already half full, with about twenty students scattered in their seats. A chorus of giggles rippled through the room as Brenda took her seat, though she didn’t immediately understand why. I kept my eyes fixed on her, watching as confusion crossed her face—her brow furrowing, her head tilting slightly. Then, right on cue, her gaze drifted toward the blackboard.

It was a precious moment for me as I reveled in her reaction. Her eyes widened in shock. Then, just as I had hoped, a deep crimson blush formed on her cheeks, spreading down her neck. She shot from her chair and stormed to the board, erasing my message with quick, frantic strokes.

To make things even better, she was wearing a snug white sweater, and the small nubs of her chest were just barely visible. When she reached her desk, she quickly folded her arms across herself, hunching her shoulders, her eyes darting around the room. She knew exactly where everyone's eyes had landed.

I leaned back in my chair, savoring the moment. Minutes later, I stole another glance at her. The blush on her face hadn’t faded. It wasn't nearly the level of humiliation I had suffered in the auditorium, yet for the first time, I tasted something like vindication.


A Reversal of Fortune

That would have been a great way to finish off the year, but to my utter regret, I made a colossal mistake. I got greedy. I wanted to relive that moment, to feel that rush again. The next morning, I arrived early once more. I had written only "BRENDA HOLLISTER HAS"—when I was startled by a sharp voice behind me.

“You little shit!” Brenda exclaimed. “I had a hunch it might be you, but I didn’t think you had it in you. Well, you’re about to pay, Blondie. Big time."

Shaken, I spun around. She stood near the doorway, blocking my escape, her eyes burning with a fury I'd never seen. I watched her reach into her purse and pull out a roll of bright orange yarn.

“Drop your pants,” she ordered.

"I... I can't do that here. Somebody might come in," I responded, my voice cracking, my eyes darting toward the door.

Brenda was undeterred. "I don't think you want Mitch and Reggie involved, do you, Blondie?"

Oh yes, the “stripped on Main Street” threat again. I swear, next time I might take my chances and call their bluff.

No, I knew better.

My fingers trembled as I unbuckled my belt, unbuttoned my trousers, and lowered them slightly, exposing my underpants. Brenda smiled and took the tops of my jeans in each of her hands and swiftly hauled them down to my ankles. Cold air hit my thighs. I watched apprehensively as she took a pair of scissors—child-sized, orange-handled, matching the yarn—and cut a length of about twenty feet from the yarn.

“Get those undies down too,” she directed.

I stood transfixed, unwilling (or, more accurately, unable) to do her bidding. “Please, Brenda, don’t do this to me!” I pleaded.

“Ah, the hell with it,” she said.

She simply snipped through my underpants and let them fall to the floor, where they grazed my feet as they pooled around my ankles. While I instinctively covered my crotch with my hands, Brenda, smiling with obvious enjoyment, picked up my severed underpants and paraded to my desk, placing them front and center for all to see.

Once again, thanks to Brenda, there was the ridiculous spectacle of my underpants displayed on my desk.

I looked around nervously as Brenda returned, yarn in hand. “Hands on your head,” she commanded.

I raised them, resigned, exposing myself completely to my tormentor.

"Well, well." She circled me slowly, examining her prey. A wicked grin spread across her face. "I see you're still as smooth as ever," she teased. “And look how tiny you are!" She pinched my penis between thumb and forefinger, tweaking it back and forth. I flinched, my hips retracting involuntarily from the sensation and the humiliation.

"Such a cute wittle boy,” said, Brenda giggling at my reaction. “What’s the matter, little boy? Are you embarrassed about your hairless little wee-wee?”

Yes, it was oh, so true. I still was completely hairless down there, a condition that caused me considerable angst. And having my small, hairless penis on display at this girl’s whim brought extreme embarrassment that burned through my entire body.

My embarrassment and apprehension increased as Brenda took the yarn and deftly wrapped one end around my penis and balls, tying a snug knot at the base of my penis.

"Okay, you can get dressed now, my little hairless one," she declared, stepping back to admire her work.

Red-faced, I hastily pulled on my jeans and buttoned them back up. But they didn’t stay buttoned for long, as the devilish Brenda immediately started unbuttoning my fly. I instinctively pulled my hips back, but Brenda was undeterred. She slipped her fingers into the opening, searching for the yarn, her fingers brushing against me, while I flinched at the intrusion. Finding her prize, she slowly threaded the yarn through, buttoning my fly with agonizing deliberation, her smirk never fading. The whole time, she acted like she had complete control over me—like I was hers to toy with. I must say it was quite humiliating having her fumbling around so close to my penis like she owned it.

She then took the roll of yarn and cut another short length and used it to tie my hands behind my back. It was soon apparent to me what wicked mischief she had up her sleeve.


The Obedient Puppy

“Let’s go for a walk." She pulled on the yarn dangling from my fly and headed for the door.

“Oh God, no, Brenda, please!” I implored, my face already burning. But she just laughed and continued walking, leaving me with no choice but to follow.

As we moved through the hallway, I could sense all eyes turning toward us. The giggles and whispers spread like wildfire, and soon enough, the noise level had risen as students pointed and laughed at the bizarre sight. Brenda strolled confidently, leading me along like a prized showpiece. I followed like an obedient puppy, my face scorching, my eyes fixed on the floor.


Courtyard Humiliation

She led me out to the main courtyard, where I was greeted with a similar response. There Brenda caught up with three of her friends, Joanna, Marcia, and Cheryl, who were standing and chatting next to the Roosevelt statue. Their mundane morning was about to become quite stimulating. As you know, I’ve had at least one humiliating experience with each of these girls, so they were predictably gleeful as they appraised my condition.

“Brenda, what have we here?” asked Joanna, relish in her voice.

“Oh, I’m just teaching Blondie a little lesson." Brenda's fingers toyed with the yarn. “Can you believe this little shit was the one who wrote about my tits on the board?"

Her friends laughed as Brenda jerked on the yarn, forcing me to awkwardly stumble forward, catching myself before I fell. Marcia, giggling freely, seized the yarn and merrily started trotting around the courtyard, her ponytail bouncing. Powerless, I was forced to follow her. There were at least two dozen other people in the area, and their laughter resonated throughout the courtyard as they enjoyed the comical sight.

Marcia stopped beside her friends and draped the yarn over Roosevelt's outstretched arm. She then pulled on the end of the yarn. I was drawn forward and upward, forced onto my tiptoes by the tug on my genitals. Marcia held me in that position while the girls chatted among themselves, ignoring me completely, while I stood red-faced and distressed.

My distress level intensified when their topic of conversation turned back to me.


Teased and Tormented

“So, Brenda,” asked Marcia while fingering the yarn and looking at my crotch, “What exactly is this tied to? Is it tied around his balls or his little dick? From what I saw in the auditorium a few months ago you didn’t have much to work with.” I blushed brighter while the four girls giggled.

"Actually," Brenda answered, “I managed to involve both his balls and his little dick. Would you like to see for yourselves?” Brenda moved toward me. My eyes widened in shock at this latest turn of events.

"Oh yes, let's see!" said Marcia, her voice rising with anticipation. "I've been wondering about that since you got here."

Of course, all three of them were in full agreement.

“No!” I yelped, the word tearing from my throat in desperation. "Brenda, please, don't do it!"

Brenda, without a word, crossed the remaining distance between us. Her fingers found the hem of my T-shirt where it tucked into my jeans, and with one smooth motion, she pulled it free, sliding it upward across my chest. I shivered involuntarily as the warm afternoon air touched my exposed skin. She pulled the shirt over my head, and I watched helplessly as she tugged it downward behind my back. With two hands, she scrunched the shirt at the small of my back, just above my tied wrists, effectively pinning my arms in place while leaving my torso completely bare.

“Excellent, my little hairless one,” she smiled while rubbing the palm of her hand back and forth across my bare chest. "So smooth. So boyish. You really do look like a child, don't you?"

I was unable to respond, and my silence only seemed to amuse her further. She lowered her hand until her fingers found my belt buckle. She began working it loose, her eyes never leaving mine as she spoke.

“What do you say we pull your pants down so they all can see what a little boy you look like down there,” she teased mercilessly. "Let's give them a proper show."

"No, Brenda! No! Please!" I begged frantically, my voice cracking embarrassingly on the final word. I looked around the courtyard, desperate for any sign of intervention, any teacher or administrator who might put a stop to this, but as usual, there would be no rescue. Instead, everyone was watching the two of us with fascination, their faces bearing the look of an audience witnessing something it wouldn't soon forget.

She ignored me completely, her attention shifting to the gathered audience as she slowly, deliberately went about her task of unbuttoning my jeans. Each movement was exaggerated, turning the simple act of undressing me into a theatrical production.

"This will be pretty easy," she announced to the crowd while undoing the first button, her voice carrying across the courtyard, "because he's not wearing any underpants."

Gleeful shouts rang out, the sound washing over me. The grins on the faces around me broadened. Brenda could sense that she had everyone’s attention, and she spoke a little louder, playing to her audience.

“You see, I took some scissors and snipped off his little tighty-whities when he refused to take them down for me like I asked him to,” she stated rather matter-of-factly, as if discussing something as mundane as the weather.

The second button came undone. She had the crowd in the palm of her hand, much to my wretchedness, and they were eating up every moment of it.

“Can you believe his impertinence? I give him a simple instruction, and he acts like he has a choice."

The third button surrendered to her fingers. My breathing quickened, my chest rising and falling with increasing speed as I watched helplessly.

“He's going to pay the price, though, because his little wee-wee is about to be put on display for all of us.” Laughter and cheering reverberated throughout the courtyard. "And I think we all have a pretty good idea what we're going to see, don't we?"

She unbuttoned the final button. I clenched my eyes shut, bracing myself for the next humiliation, my mind screaming for this to end. Brenda held onto the top of my trousers, holding the fly closed with maddening restraint. Of course, this would be a temporary situation. She looked up at me, grinning sadistically, clearly savoring every moment of my trepidation.

"Are you ready, big boy?" she teased, the irony of the nickname not lost on either of us. "Are you ready to show everyone what you're working with? To prove all those rumors true?"

“Please... Brenda, I’m begging you... don’t do it!” I pleaded, my voice shaking. “I’ll do anything. Anything you want. Just not this. Please—not in front of everyone.”

“Oh, come on, sweetie, you don’t mean that. Look how much fun everybody is having. They can’t wait to see what you've got down there.” She paused, looked me in the eyes and smiled. “Boy, they’re in for a good laugh, aren’t they, Blondie boy?”

She slipped behind me, her arms circling my waist as she held my pants in place. Leaning in close, she brought her lips right to my ear, her breath warm against my skin, smelling faintly of peppermint gum.

"Prepare yourself, my little hairless one," she taunted, her voice dropping to a whisper meant only for me, tickling my ear in the process and making me shiver involuntarily. “In a few moments, I’m not just going to give everyone a quick little peek. I’m going to pull your pants aaaaaall the way down. And if the mood strikes me, I might just take them completely off!”

"Oh, God!" I squealed, the sound embarrassingly high-pitched. My anxiety was mounting with every passing second, and I swear I could hear my heart pounding against my sternum.

Brenda was relentless with her psychological torture. “Just think, your tiny little hairless bits are about to be exposed for all these people out here.” She paused for effect, letting the image settle in my mind. "They'll all be staring and laughing at you, and you'll be squirming around, totally helpless to do a thing about it."

"No! Brenda! Please!" The words came out of me automatically, even though I knew they would change nothing.

“Oh, yes, Blondie boy. This is going to be a moment you’ll remember for the rest of your life.” She paused, letting that sink in. “And so will all these people out here. Every time any of them sees you, they’re going to think, ‘There’s the guy who was stripped and humiliated by a girl in the courtyard.’” Brenda giggled and continued. “And they’ll always have the picture in their head of your teensy, hairless weenie bobbing about while you wiggle around helplessly.”

I was frantic, as it sunk in that she was absolutely right in that assessment. This wasn't just happening now. This would follow me forever. She took notice of my horrified look, and her smile widened with satisfaction.

“Ah, you know it’s true, don’t you, Blondie? Can’t you just picture the look on everybody’s face in just a few seconds when I pull your pants down? For all intents and purposes, you’ll be naked. And ohhhh, so naked you will look, with no hair on your body. I mean, think about it. You’re out here in broad daylight, and your tiny, hairless, little-boy penis will be on display for all these girls that you’ll have to face for the rest of your days at Roosevelt High." Her voice became almost sympathetic, which made it infinitely worse. "Every time they see you, either in the hallway, or maybe in the same class, they'll picture you naked. It'll almost be like you're reliving this all over again. The image will be burned into their brains. That's the guy with the baby dick. That's the guy who got stripped in the courtyard. Poor little Blondie."

"When I take these down, it should be quite comical, because you’ll be squirming around in absolute humiliation, and your little pee-pee will be jiggling around... oh, my, it will be quite the spectacle, don’t you think so?”


The Unveiling

Brenda pulled her mouth away from my ear, and I felt the inevitable closing in on me.

"Brenda, pl-" I started, but she cut me off.

“Here we go, folks,” she announced, her voice ringing with mischievous delight. "Is everybody ready? Is everyone prepared to witness the big reveal? The moment we've all been waiting for?"

A loud, enthusiastic cheer erupted from the gathered students, their excitement palpable. Brenda stepped back slightly, positioning herself for maximum dramatic effect. Panic surged through me, but all I could do was cry out in desperation.

“No! No!”

“Wheeeeee!” she yelled gleefully while sliding my pants all the way down to my ankles in one steady motion. I was exposed, the warm afternoon air touching places that had never been meant for public view.

The roar of laughter in the courtyard was riotous, immediate, and overwhelming. I writhed and twisted my body frantically, my hips bucking in desperate, futile attempts to conceal myself, but there was nowhere to hide. The yarn leash pulled taut, reminding me of my captivity, and I could only stand there, exposed and trembling.

“Look at that teeny, little thing!” laughed one of the girls. “It’s like a little clitty!” she exclaimed, drawing uproarious laughter from the crowd that seemed to go on forever.

"And he has no hair!" squealed another, her voice pitched high with delighted shock. "Not a single hair! He looks like a little kid!"

"Oh, this is too much!" someone else called out. "I can't believe this!"

Mortified to the max, I tried lifting each leg up one at a time in a frenzied attempt at covering up, my movements jerky and uncoordinated. But I soon abandoned that effort when I realized my frantic movements threatened to displace my pants altogether. Just as Brenda had predicted, I could only stand there, squirming helplessly, forced to endure the laughter and ridicule of the thoroughly entertained crowd.


Paraded to Homeroom

Mercifully, the warning bell rang out, signaling the end of my public torment. The crowd slowly began to disperse, though not before a few final glances and pointed comments were thrown my way. Marcia let go of the yarn, and Brenda bent down to button and buckle me up, making sure the yarn stuck out from my fly, displaying my continued submission. I was relieved that she didn’t make good on her threat to take my jeans completely off. But, to my dismay, she chose to leave my upper body exposed, my shirt still bunched at my back, my chest bare for everyone to see.

“Alright, girls, time to take my little doggy back to homeroom,” Brenda laughed, giving the yarn a playful tug as she started leading me toward the building. "Show's over for now, but don't worry. There will be encores."

“Thanks for the show, Blondie dearest! Let’s do this again soon!” Marcia called out, her words dripping with amusement as her friends burst into fresh laughter.

The giggling chorus followed me as Brenda paraded me back through the hallway, the same humiliating walk of shame as before—only this time, with my shirt missing, my embarrassment felt even worse. The cool air of the air-conditioned corridor raised gooseflesh on my bare skin, and I could feel the eyes of passing students on me, their gazes lingering on my exposed chest before dropping to the yarn leash that announced my humiliation.

We stepped into homeroom, where most of the students had already gathered. With Miss Farnsworth still absent, Brenda seized the opportunity to extend my humiliation, proudly parading me back and forth across the front of the room like a prize she was showing off. Laughter filled the air as my classmates soaked in the spectacle.

We reached my desk, and Brenda finally untied my hands. “All right, you can put your shirt back on now and tuck your little leash in your pants, my little pet,” she said with a smirk. “Oh, but before you sit down...” She leaned in, whispering her final instruction in my ear. I winced as she pulled away, her eyes dancing with malicious delight, then turned on her heel and strutted to her seat, leaving me to my fate.

With trembling hands, I slipped my shirt back on and stuffed the trailing yarn into my fly, but the worst was still to come. Taking a deep breath that did nothing to calm my racing heart, I walked to the chalkboard. I hesitated, then reluctantly picked up a piece of chalk. My stomach twisted into knots as I forced myself to scrawl out the humiliating words in large, bold letters:

"BLONDIE HAS A TEENSY WEENSY HAIRLESS LITTLE PEE-PEE."

The room erupted into hysterical laughter, the sound crashing over me. I’m sure it was poetic justice for Brenda as I turned and walked briskly back to my seat, staring at the floor while blushing crimson. Waiting for me on my desk, like a final cruel reminder of everything that had happened, were my shredded underpants. Shamefaced, I snatched them up and stuffed them into my pocket, a routine I was growing far too accustomed to.

I couldn’t bear to look back, but I’m sure Brenda was basking in the moment, grinning from ear to ear while soaking in her revenge.
Last edited by Blondie on Wed Sep 02, 2026 9:25 pm, edited 8 times in total.
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Roosevelt Humiliations, Chapter 8

Post by Blondie »

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Chapter 8: Classroom Humiliation

Miss Farnsworth Has Her Way with Me

Well, I suppose I should finish recounting the next-to-last day of my sophomore year. As you may recall, my morning in homeroom had already been quite an ordeal. Brenda had cut off my underpants and tied a bright orange yarn around my dick and balls. As payback for writing on the board about her small titties, she had made me write on the board in large, humiliating letters:

“BLONDIE HAS A TEENSY WEENSY HAIRLESS LITTLE PEE-PEE.”

I sat slouched in my chair, my face burning as my classmates snickered and whispered around me. And just when I thought things couldn't possibly get worse, in walked Miss Farnsworth.

Her eyes immediately flicked to the board, and for a brief moment I detected a slight smirk playing at the corners of her mouth. When she turned and looked at me, I swear her gaze lingered on my crotch. I caught myself self-consciously pushing my knees together. In any case, it was not the look of a teacher about to swoop in and save me.

"Mr. Haggerty," she said. "Would you care to explain who is responsible for this?" she asked me while pointing to the board.

I swallowed hard. My eyes darted to Brenda, who met my gaze with a look that would have pierced my forehead if it was physically possible. I knew what I had to say.

"I am, ma’am," I admitted, my voice barely audible.

"Is that so?" Miss Farnsworth replied, her eyebrow arching. She took two slow steps toward my desk. "And tell me, Mr. Haggerty, what exactly prompted you to broadcast such... personal information about yourself?"

I was flustered. "I... I don't know what you mean," I stammered, and I immediately regretted saying anything at all.

"You don't know what I mean?" she repeated, looking incredulous. She turned back to the board, reading my humiliation aloud with relish: "'Teensy weensy. Hairless. Little pee-pee.' What about that statement do you not understand? My goodness, one might almost think you were proud of these attributes."

The class erupted again, and I felt my face turn a shade of red I was certain had never before been achieved by humans.

I had no response. I cringed, dreading whatever Miss Farnsworth would do next. I had already found out firsthand during my freshman year that she possessed a genuinely sadistic side. As the reader may remember, on that occasion Mitch and Reggie forced me to go into homeroom without my pants. She furthered my humiliation by making me remove my shirt and remain clad in just my tighty-whities for the remainder of the homeroom period. I could still recall the grin on her face when she looked me up and down, her eyes gleaming with something that suggested she was deriving more than a little pleasure from the experience.

Plus, I later learned that she had quite a reputation for the inventive ways she punished her students. Her methods invariably involved some degree of public embarrassment, and more often than not, clothing played a central role.

Take, for instance, what had happened to a girl in her third-period English class just last month. After disrupting the lesson one too many times with her constant chatter, she found herself on the receiving end of one of Miss Farnsworth’s embarrassing consequences. Miss Farnsworth had taken her behind a partition and dressed her in a baby blue little girl's party dress, complete with a stiff petticoat that made the skirt stand out like a bell. It had puffy sleeves and was very short, barely covering her panties. She had added frilly white anklets, shiny black patent leather shoes, and a large bow in her hair that matched the dress perfectly. The poor girl had been forced to wear the ridiculous outfit for the remainder of her classes that day. I remembered seeing her in the cafeteria during lunch, her face as red as a ripe tomato.

But I digress. Now it was about me, and I had an awful, sinking feeling that I was about to become the next victim of her particular brand of depravity.

“Would you please stand up, Mr. Haggerty?” she demanded.

Slowly, dreadfully, I rose to my feet, acutely aware of every set of eyes locked onto me.

"I have a tip for you, young man," began Miss Farnsworth, stepping closer to my desk. "In the future, it would be wise not to advertise your shortcomings."

Laughter boomed from all sides. My face turned beet red, and the heat of my embarrassment was almost unbearable.


The Bra

Miss Farnsworth opened the bottom drawer of her desk and began rummaging through it. My stomach twisted into knots as she spoke.

"Mr. Haggerty, are you familiar with the concept of shame clothing?" she asked, not bothering to look up from her search.

My mouth opened, but no words came out. I had a pretty good guess at what it meant, but my brain was too busy screaming in panic to form a coherent response.

"Cat got your tongue?" she inquired, still pawing through the drawer. "I'll take that as a no. Shame clothing, my dear boy, is an... educational tool I developed myself. The theory is quite elegant, really—when a student misbehaves, particularly when that misbehavior involves inappropriate attention to one's body or the bodies of others, the appropriate remedy is to redirect that attention in a manner that encourages... self-reflection."

She continued her search, unfazed by my silence. "I've found that shame clothing can be an exceptionally effective teaching tool. There's just something about watching a student turn all sorts of lovely shades of red while wearing a carefully selected garment of..." She trailed off, then let out a delighted little “Oh!” as she pulled something from the drawer.

She held it up for the entire class to see—a delicate, lacy black bra. The room erupted. The laughter, the hoots, the absolute hilarity of my classmates echoed off the walls.

Miss Farnsworth held the bra at arm’s length, admiring it as if she had just unearthed some priceless treasure. “Oh yes,” she cooed, her eyes twinkling as she took in my mortified expression. “I’m quite confident this will do nicely.”

I barely heard the continued cheers and cackles from behind me. I was too busy trying to come up with a way out of this horrific nightmare, frantically searching my mind for some escape route that didn't exist.

But then came the inevitable command. "Now then," she said, clapping her hands together. "Let's get you properly attired, shall we? Would you please remove your shirt and come up here, Mr. Haggerty?"

My stomach plummeted. Defying her would only make things worse—much worse. Swallowing hard, my face burning, I reluctantly peeled my shirt over my head. The instant it cleared my head, the giggles behind me doubled in volume. I didn’t dare turn around; I could already picture Brenda laughing gleefully, her face flushed with delight.

I trudged to the front of the room, my arms hugging my shirt to my bare chest. Miss Farnsworth plucked it from my grasp with an amused smirk and draped it over the back of her chair.

“You won’t be needing this for a while,” she remarked.

Then, before I could react, she placed her hands on my shoulders and turned me to face the class. My gaze dropped immediately to the floor, as I couldn’t bear to look any of them in the eyes.

Miss Farnsworth let the moment simmer before continuing. “Given what you wrote on the board about your 'teensy weensy' penis, it seems you’re not feeling very manly today, are you, Mr. Haggerty?”

My lips moved, but any words I might have formed were completely drowned out by the delighted shrieks and giggles of my classmates.

"I asked you a question," she said. "Are you feeling manly today?"

I didn't know quite how to answer. "I... I... um... I guess not."

"How unfortunate for you," she replied, her tone suggesting she found it anything but unfortunate. "But perhaps we can help with that. Or rather, help you embrace the alternative. Hold your arms out to the sides, please."

I hesitated, my muscles locking up. But refusing wasn't an option Slowly—painfully slowly—I lifted my arms. She stepped behind me and reached around my chest, holding the bra’s unfastened cups in place against my skin. She continued teasing me as she went about her task of fastening the cups together.

(It just dawned on me as I'm writing this that she probably intentionally picked a bra that clasped in the front for this very purpose, ensuring maximum exposure and embarrassment while she went about her task.)

She was standing very close to me. Her mouth was near my ear as she looked over my shoulder, her breath warm against my neck. She leaned slightly toward my ear, speaking just loud enough for everyone to hear.

“This is quite the appropriate attire for someone who isn’t feeling very manly, don’t you think so, Mr. Haggerty?”

The only response was another round of laughter at my expense, louder and more raucous than before. With excruciating meticulousness, she clasped the front of the bra together, giving the lace a little tug for good measure. She stepped back to appraise her work, her head tilted to one side

“I like to keep this double-A cup handy for my flatter-chested girls,” she mused.

Heavier laughter ensued. I couldn't help myself and stole a glance at Brenda, immediately regretting it. She was wiping actual tears from her eyes, her body shaking with the force of her laughter. I snapped my gaze right back down just as Miss Farnsworth lifted the straps.

“Arms through here, please... excellent.”

She guided my arms into place and pulled the straps snugly onto my shoulders. Then, as if she were dressing a mannequin in a department store window, she gave the cups one final adjustment, stepped back, and admired her work with the satisfaction of an artist viewing a completed masterpiece.

"Perfect!” she declared, her eyes dancing with amusement. "And my, you’re blushing like a little schoolgirl!”

I glanced up at her and saw that her demonic eyes were dancing with delight. I couldn’t imagine feeling more miserable, or more humiliated.


Trousers Down

Miss Farnsworth’s gaze drifted downward, settling pointedly on my lower half. She tapped a thoughtful finger against her lips, appearing to be deep in thought. I remember thinking that whatever she was considering, it was not going to end well for me. And sure enough, my worst fears were about to be realized, and in spectacular fashion.

“Mr. Haggerty,” she began, her voice carrying a tone of amusement. “As I recall, the last time I had to discipline you, you weren't wearing trousers, and you were showing off some very pretty legs.” She paused, letting her gaze travel slowly down my body. My stomach dropped. “I think, since you’re already standing here on display in such a pretty bra, it would be quite appropriate—and entertaining, I might add—for you to put your pretty legs on display also."

She let that sit there momentarily while the ramifications of her proposal caused my jaw to drop and my eyes to widen. I was too flabbergasted to speak, my mind reeling from the implications.

“I’d like you to lower your trousers now, Mr. Haggerty,” she instructed, her tone light yet firm. “Let’s show off those pretty legs for everyone.”

“I... I can’t,” I stammered, panic creeping into my voice. The words came out before I could stop them, a desperate reflex.

Slightly taken aback, she looked at me sternly. “What do you mean, you can’t?” she asked, her tone carrying the unmistakable warning that resistance would not be tolerated. "Explain yourself, young man. Immediately."

I swallowed hard. “I just... please, don’t make me.”

She sighed, shaking her head slowly. “Now, now, Mr. Haggerty, let’s not be difficult. You’ll do as you’re told and pull your trousers down. Unless, of course, you’d rather I call in Mr. Jennings and have him review the lovely message you left on the board? Perhaps he'd like to discuss your... creative writing... with your parents over dinner this evening?"”

That thought sent a fresh wave of dread coursing through me. Mr. Jennings, the new principal, had already built a reputation for being just as sadistic as Miss Farnsworth—if not more so. I'd heard rumors from the upperclassmen about his "disciplinary methods," stories that made my blood run cold. Worse still, if he got involved, there was a very real chance my parents would hear about this. No, that was not an option. But still... I had to at least try to reason with her, to appeal to whatever shred of mercy she might possess.

I leaned forward slightly and I spoke the next sentence very softly, so only she could hear me, my voice barely a whisper. "I'm not wearing any underpants."

The moment the words left my mouth I felt my face burn hotter than ever, and glow even brighter when I saw the grin spread across her face. My hope that she would show compassion with the knowledge that I was naked underneath my jeans was apparently nothing more than a fantasy. If anything, it seemed to whet her appetite for more humiliation, to give her additional ammunition.

She arched an eyebrow, then turned her head ever so slightly toward the class. "Why aren't you wearing underpants, Mr. Haggerty?" she inquired—loudly, her voice projecting to the back row.

The reaction was instantaneous. Laughter exploded behind me, a mix of giggles, gasps, and outright guffaws. I wanted to sink straight through the floor.

As much as I wanted to tell the truth—that Brenda had cut them off me with a pair of scissors, and that she made me write about my penis on the board under threat of worse—I knew that would come back to haunt me down the road, and in a very big way.

“I... I didn’t have any clean underwear this morning,” I mumbled, barely able to utter the words.

"Well, I guess that will be your regret and our windfall," she said, flashing a wicked smile. "Now we'll get to see if what you wrote on the board is actually true. I must admit, I am skeptical about the hairlessness, considering your age. As for the size..." She let her gaze drift pointedly downward, and I felt my skin crawl. I did see you in your underpants, so I think you might be accurate in that regard."

She let the laughter die down before continuing, her eyes twinkling with anticipation. “Now then, let’s get those trousers down and have a look. Chop chop, Mr. Haggerty. We haven't got all day.”

Have a look?

A fresh wave of panic gripped me. I felt like I was trapped in a surreal nightmare, the kind where you scream but no sound comes out. My hands hovered over my belt, trembling slightly, but my body refused to obey the command. Instead, in a futile act of self-preservation, I crossed my arms tightly over my chest—over the bra—as if that would somehow shield me from further embarrassment.

Miss Farnsworth sighed. “Oh, for Pete’s sake. I’ve had just about enough of your nonsense,” she said, her patience clearly wearing thin. “Trousers. Down. Now.”

Then, much to my absolute horror, she took a step forward and reached for my belt.

“No!” I yelped, pure instinct taking over as I grabbed her wrists. She stopped and looked me in the eyes with a cold stare that seemed to sear its way into my core.

"If you ever dare touch me again, Mr. Haggerty, you will feel wrath and humiliation the likes of which you've never experienced. Do you understand me?"

I released her immediately, dropping my hands uselessly to my sides. That was all the opening she needed. In one swift, terrifyingly efficient motion, Miss Farnsworth undid my belt, unfastened my jeans, and yanked them straight down to my ankles.

The classroom erupted. The laughter was loud and merciless. And amidst the cacophony, I somehow made out Brenda’s hearty laugh, seemingly louder than the rest. My hands flew to my crotch, shielding myself desperately. But the moment my fingers brushed against something trailing down my leg, my heart stopped. I had completely forgotten about the bright orange yarn, which was now dangling to the floor.

Miss Farnsworth’s curiosity was clearly piqued. With an amused smile, she reached down, took hold of it, and gave it a gentle tug. A jolt of panic shot through me.

"Why, pray tell, did you tie your genitals with yarn, Mr. Haggerty?"

It was a simple and reasonable question, one I couldn't answer truthfully, and one where I had no backup answer for the truthful one.

“I-I-I... I don’t know,” I answered wittily.

Miss Farnsworth’s brows shot up. “You don’t know?” She let the words hang for a second before repeating, her voice dripping with incredulity. “You don’t know? What are you, some kind of pervert?”

I could have thrown that same question right back at her, but I was in no position to do so. My pants were around my ankles, I was wearing a bra, and my genitals were decorated with yarn.

“No! I mean, I’m not... it... it was just a silly game, and I forgot to take it off,” I finally managed, my voice barely above a squeak.

Miss Farnsworth gave a slow, exaggerated shake of her head. “A silly game, indeed.” She let go of the yarn and took a step back. “Well, whatever the case... let’s get those hands away from your privates.”

Panic surged through me. My hands were the only thing standing between me and complete humiliation. “Oh, please!” I pleaded, my voice cracking. “Don’t make—”

She cut me off with a sharp, authoritative tone. “Put... your hands... on your hips, Mr. Haggerty. NOW!”

The forcefulness of her voice compelled me to quickly move my hands to my hips, exposing my nudity to the now very amused Miss Farnsworth, who was staring at my newly bared genitals with a devilish grin on her face. Clearly enjoying herself, she took her time appraising me.

“My, my, Mr. Haggerty... now I see why you were so reluctant to show me your privates.” She paused for dramatic effect, letting the class revel in my misery before adding, with a mocking touch of sympathy, “You poor, dear boy.”

My entire body burned as she continued her slow, deliberate examination, while I stood there—rigid, mortified, and desperately wishing for the floor to swallow me whole.

Another grin. And then, "You must be awfully embarrassed."

Embarrassed? What was your first clue? Maybe my glowing, pulsating face? The fact that I was wearing women's lingerie? The yarn?

Miss Farnsworth turned to look at the chalkboard, then back to me. "Mr. Haggerty, please read aloud what you've written on the board. And please be loud enough so all your classmates can hear you."

I winced, then carried out her directive, my voice cracking on every word: "Blondie has a teensy weensy hairless little pee-pee."

Miss Farnsworth waited for the laughter to die down, then looked down at my penis. "Indeed, you do," she said while nodding, drawing out another chorus of laughter that seemed to go on forever.


I Feel Pretty

Miss Farnsworth beamed at me with amusement. “You look very pretty. Do you feel pretty, Mr. Haggerty?”

I remained silent, hoping she might move on. But she demanded a response.

“I asked you a question, Mr. Haggerty. Do you feel pretty?”

“I... I... I don’t know,” I stammered, feeling utterly ridiculous.

She nodded thoughtfully. “Well, you certainly look pretty..." She tapped a finger against her chin, and a slow, wicked grin spread across her face. "Hmm, perhaps I can help you find the answer. Tell me, have you ever seen the movie West Side Story?”

I had no idea where this was going, but I figured honesty was the safest route. "Um... yes, I saw a school play of it. Last year. It was... it was fine."

Her smile widened, showing teeth. “Excellent! Then you must remember Maria singing I Feel Pretty. Would you be so kind as to perform it for the class?”

I shook my head back and forth, demonstrably, desperately. "No. No, I can't—I don't sing, I... I can't."

“Oh, but I’m sure you can,” she cooed. “And since you look so pretty, it would be simply delightful if you could sing it for us.” She turned to the class. "Don't you think so, class?"

The chorus of agreement was immediate. It was officially a nightmare.

“Here, let me refresh your memory.” She cleared her throat and broke into song. ♬ “I feel pretty... oh so pretty... I feel pretty and witty and gay...” ♬

The class erupted in laughter—at her performance, at my situation, at the sheer absurdity of it all. Miss Farnsworth, unfazed by their reaction, turned back to me with a satisfied grin.

"There we go! Now, your turn, Mr. Haggerty. From the top, if you please."

“Please, I... I can’t... I don’t know the words...” I tried weakly.

“Well, we’re in luck! I just happen to have the sheet music.” She slid open her middle drawer and produced it. She handed me the sheet, which I accepted with trembling fingers.

She actually planned for this.

“Now, face the class and sing for us. Let everyone hear how pretty you feel. And if you do a really nice job—if you really sell it, Mr. Haggerty—I'll let you put your shirt on and pull your pants up before you head to your next class."

Singing was bad enough. Turning around and facing my classmates? Unthinkable. The thought of thirty pairs of eyes on me, on that, while I sang about feeling pretty...

“B-but Miss Farnsworth,” I begged, my voice cracking into a high-pitched plea. “I’ll sing, just... please, can I face this way? I'll sing loud, I promise, just don't make me turn around—”

She scoffed. “Nonsense, my dear. That would be quite rude to your audience. You’ve captured their attention, after all. It’s only polite that you face them. Plus, you have written on the board that you have a teensy weensy hairless little pee-pee. So it would only be fitting for you to put what you call your teensy weensy hairless little pee-pee on display, so your classmates can make that judgment on their own. Don't you think so, Mr. Haggerty?"

I swallowed hard. My body refused to move. But I knew what was expected. With every ounce of willpower I had, I turned around.

Immediately, thirty pairs of eyes locked onto me. More specifically, onto my mid-section. For now, the only thing standing between me and total exposure was the sheet music I was gripping like a lifeline—a situation that would, of course, be temporary, thanks to the demonic Miss Farnsworth.

She clapped her hands. “Mr. Haggerty, kindly hold the sheet music to the side with one hand and place your other hand behind your back. I've had enough of your impertinence." She paused, her eyes dropping to my exposed midsection. She smiled. And if you think about it, you don't have much to hide down there anyway, do you, Mr. Haggerty?"

This is it. This is how I die. My little penis will be fully exposed to all, and there is no hair for it to hide behind.

Laughter rippled through the room as I reluctantly complied, shifting the sheet to my side. Even after all I had endured at Roosevelt High up to that point, at that moment it was the most embarrassed I had ever been in my entire life. And I had a sinking feeling that Miss Farnsworth was only getting started.

Miss Farnsworth grinned from the back of the room. “Excellent! Now, let’s hear how pretty you feel.”

I swallowed the lump in my throat, lifted the sheet music to my face, and began to sing, though I was barely audible.

♬ “I feel pretty...” ♬

“Hold it!” Miss Farnsworth interrupted. “Keep that sheet music away from your face, so we can see you glow.” I lowered the sheet, exposing my burning cheeks. She chuckled. “Class, have you ever seen a face quite that red?"

The giggles intensified. “I do believe the shame clothing is working. Do you feel shamed, Mr. Haggerty?” I gave a small, miserable nod. “Excellent!" She clapped her hands again. "Now, from the top. With feeling!” She motioned for me to continue. "And remember, Mr. Haggerty—the more you commit to the performance, the sooner we can all move on with our day. Your classmates are waiting."

I drew a shaky breath, and began again: ♬ “I feel pretty... oh so pretty... I feel pretty and witty and gay...” ♬

The class was howling with laughter now. My voice wavered.

“Continue, Mr. Haggerty!” Miss Farnsworth commanded. "Louder! With conviction! Make us believe you feel pretty!"

♬ “And I pity... any girl who isn’t me tonight...” ♬

I stood there, my chest heaving beneath the bra, my arms still pinned behind my back in a posture of submission.

Mercifully, the bell rang. Miss Farnsworth started clapping as she strode to the front of the room. The class followed her lead, applauding my performance with glee, some of them rising to their feet in a standing ovation of mockery. Thoroughly shamed, I turned away and bowed my head in pure humiliation as the room began to empty.

Miss Farnsworth walked up and plucked the music from my hand. “That was well done, Mr. Haggerty.” She picked up my tee shirt from the back of her chair and held it out to me. “Here. You’ve earned this.”

I all but snatched it from her, shoving it under my arm as I hastily pulled my pants up, my fingers fumbling with the zipper in my haste. I reached up to undo the bra clasp, when...

“Uh, uh, uh!” Miss Farnsworth tutted. “I said you could have your shirt back. I didn’t say you could remove your bra.”

I froze, staring at her, my mouth open in horror. She smiled. “You’re to wear your pretty bra for the rest of the day, Mr. Haggerty. You may return it to me at the close of classes today."

“But...”

“No arguments. Or I’ll take your shirt back, and you can show off your lovely bra all day long. Imagine the conversations, Mr. Haggerty. Imagine the laughter." She leaned slightly closer, her perfume overwhelming. "Now be on your way, or you'll be late for your first class. And don’t you ever write on my board again about your physical deficiencies.”

Miss Farnsworth turned to Brenda, who was lingering nearby, wearing a grin. “Brenda, dear, would you be so kind as to keep an eye on Mr. Haggerty today? That black bra shows quite nicely through his white tee. She turned back to me, her eyes dropping to my chest with obvious satisfaction. "If at any point he removes it, do let me know. I have a pair of matching panties in my drawer for tomorrow if he decides to disobey me." She paused, considering. "I probably can't send him to classes with his little penis on display, but I can certainly send him off in a bra and panties set. Perhaps with a little bow in his hair to match."

Brenda’s grin widened. “Oh, I’d be delighted, Miss Farnsworth. I actually hope he tries it." She looked at me and grinned. “I think Blondie would look adorable in a pair of panties. Maybe with some little ruffles?"

Miss Farnsworth chuckled. “Indeed."

They both watched as I donned my T-shirt over the bra. For a moment I allowed myself a spark of hope—maybe it wouldn't be so visible. I looked down. Miss Farnsworth was right. To my utter chagrin, the dark outline of the bra was unmistakable. The straps were visible through the thin cotton, and the cups created dark shadows that no one could possibly miss.

"Now, off you go, Mr. Haggerty." She made a shooing gesture with her fingers. "And tuck your shirt in. I want you to feel pretty all day long.”

I stumbled toward the door, my face burning. As I hurried out into the hallway, I could still hear the demented lady cackling to herself, the sound echoing in my ears.
Last edited by Blondie on Wed Sep 02, 2026 9:26 pm, edited 10 times in total.
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Roosevelt Humiliations, Chapter 9

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Chapter 9: Stripped on the Soccer Field

A Lunch Date with Brenda

I walked through the hallway as quickly as I could, hoping I could somehow put my ordeal in Miss Farnsworth's class behind me. But then I heard Brenda’s familiar voice calling out to me.

“Oh, Blondie,” she called out, her voice singing my name.

I stopped in my tracks, shut my eyes, and took a deep breath. It wasn’t over. Not by a long shot.

Within seconds, she was beside me, casually draping an arm around my shoulder as we walked.

“I’d like you to meet me during lunch today, my pretty bra-wearing friend,” she instructed. "North end of the soccer field. Let's say... twelve-fifteen sharp. I expect to see you there.” Her grip tightened ever so slightly, just enough to remind me that I had no real choice in the matter. “Oh, and make sure you’re still wearing that little leash I made for you.” I swallowed hard. “Don’t be late, sweetie. I’d hate to have to tell Mitch you’ve been misbehaving.” She leaned in closer still. “Did I mention he's my cousin? He absolutely adores me. He’d do anything I ask. Anything at all.”

With that, she gave me a gentle squeeze on my ass before veering off in another direction, leaving me rooted to the spot, my mind racing with terrible possibilities.

“Oh, God...” I muttered under my breath, forcing myself to move toward my first class.

The bra experience? I don't think I need to elaborate on the harassment I endured throughout the day. Needless to say, the torment was ruthless and unrelenting. I constantly fought the urge to just reach under my shirt and rip the damn thing off.

But at least the harassment was predictable. I knew what to expect, could brace myself against it.

Brenda, however, was not predictable. I had no defense against her.

By 12:15, I found myself making the dreaded trek to the soccer field. As I inched closer, to my dismay I discovered that Brenda was with Marcia, Joanna, and Cheryl. Marcia was the first to notice me approaching. I watched her elbow Joanna, pointing in my direction and mouthing the words, “There he is.” The others turned, their faces lighting up with grins of delight.

“Hi, Blondie!” they greeted me in perfect synchronization.

I barely had time to respond before Joanna, smirking, tilted her head at my shirt. “Honestly, Blondie... didn’t your mother teach you never to wear a dark bra under a light shirt?"

The girls erupted in giggles while Brenda stepped forward. Without a word, her hand drifted down to the front of my jeans. Her fingers found the middle buttons of my fly. My body tensed.

“Brenda, please...” I croaked.

But before I could finish, she was unbuttoning them. I couldn’t restrain myself and I grabbed her wrists and pulled them away before she could go any further. Brenda simply stared at me. Then, in a voice that left no room for argument, she said, "Put your hands on your head. Keep them there until I say otherwise." A pause. "Unless you want me to get Mitch involved. Your choice, Blondie."

I hesitated, and then, with a sinking feeling, I slowly raised my hands and placed them on my head. Satisfied, Brenda slipped her hand back into my jeans. Her fingers brushed against my balls, and I flinched involuntarily.

"A little twitchy, are we, Blondie?" she giggled.

She retrieved the end of the yarn, and with a triumphant tug, she pulled it through the opening of my fly.

"Let's go for a walk," she announced, and she began to stroll down the field, strolling backward, leading me by the yarn like some prize poodle at a dog show. Her giggling friends walked alongside us, delighting in my submissiveness. I could do nothing but follow, hands locked behind my head, my humiliation mounting with each step.

It didn’t take long for the bystanders to notice. Their murmurs turned into laughter, and by the time we reached the far side of the field, all eyes were on me, drinking in my degradation.

At that point, Brenda decided to escalate. Grinning wickedly, she reached down, unbuckled my belt, and undid the remaining two buttons of my jeans. I froze. For now, the denim stayed up. But we both knew... the moment I took another step, they were bound to start sliding down.

“Please, Brenda, I’m begging you, don’t do this to me. I’m not wearing any underpants,” I pleaded desperately. "Please."

Brenda merely smirked. “You should’ve thought of that before you wrote on the board about my tits." Then she added, “Now, hands up—high in the air.”

I hesitated, but the expectant look from Brenda left me with no real choice. Slowly, trembling, I raised my hands high above my head, a position of total vulnerability. Brenda wasted no time. She grabbed the hem of my shirt, pulled it up, and yanked it over my head, stripping it off completely. With an air of satisfaction, she tossed it to Marcia, who caught it with a titter of delight.

A cool breeze swept across my exposed skin, raising goosebumps, but the real shiver that ran through me came from the intense humiliation. The four girls erupted into delighted whoops, their eyes fastening upon my now fully exposed lacy black bra with expressions of pure, unadulterated glee. My blushing face only encouraged them further.


Pants Come Down

“Hands back on your head, pretty boy,” Brenda giggled. “And just so you know, if you dare move them, your jeans are coming off completely. And you'll never see them again."

I swallowed hard and obeyed. Then, with a wicked glint in her eye, Brenda turned and began leading me back across the field. She walked backward, keeping a close eye on my jeans, and her three friends followed suit, their faces lit up with anticipation.

As I trudged behind her, I risked a glance around. The audience had grown—at least forty or fifty people now, perhaps more, all watching and laughing.

At first, my jeans mercifully stayed in place. But then Brenda picked up the pace. And I felt it. The waistband loosened. The denim slipped ever so slightly around my hips.

“They’re slipping!” Cheryl squealed gleefully.

I clenched my jaw, desperately trying to keep them up without breaking Brenda's rule, without dropping my hands. I stretched my legs out as much as I could, taking exaggerated steps, trying to slow their descent. But I was only delaying the inevitable. The waistband hovered precariously on my hips, then Brenda, sensing the moment, sped up. One step. Two steps. My jeans dropped to my knees. Another two steps, and they collected at my ankles.

The outcry from the girls before me and from the assembled onlookers remains embedded in my memory to this day—laughter, cheers, and shouts of delight. What a sight I must have been, naked from the ankles up but for a black bra, my hands still clamped behind my head, awkwardly trying to keep pace with Brenda's relentless backward march.

"Look at his little weenie!" Joanna laughed, pointing with glee.

“And ‘little’ is the operative word,” countered Marcia, her voice carrying across the field.

“It looks so cute, the little hairless thing bobbing around like that!” chimed in Cheryl.

Brenda continued leading me, dragging me across the field as I struggled to keep up, my gathered pants hobbling my steps. As if the spectacle wasn’t enough, she made a game of it, zigzagging across the grass, forcing me to awkwardly shuffle behind her as she ran, her laughter ringing in my ears.


Naked But for a Black Bra

By the time we reached the far end of the field, I was gasping—not just from exertion, but from sheer, overwhelming humiliation. And yet, Brenda wasn't finished. She led me straight to the goalpost, where she tied the end of the yarn securely to the net, tethering me like she would her pet dog. Then, kneeling down before me, she grabbed my ankle.

“Leg up,” she commanded.

I hesitated. “Please, Br—”

SPLAT. The sound of her palm hitting my naked ass echoed across the field like a gunshot.

“LEG UP!” she barked.

Heart pounding, I obeyed. Brenda tugged off my sneaker, then slipped my pants leg free. As an afterthought, she stripped off my sock as well. Then she grabbed my other ankle.

“Leg up.”

I whimpered, a sound of pure abject misery, but I complied. Within seconds, she had me standing in nothing but a black bra, tethered by my own genitals to a soccer net, surrounded by what felt like half the student body. A fresh wave of mortification crashed over me, so intense I thought I might faint.

“You’ll find your clothes in the other goal,” she said, dusting her hands off. “Once you untie yourself, I want you to crawl on your hands and knees like the nice doggie you are until you reach your... goal.” She giggled at her own wordplay. “And if you ever make another reference to my tits then today will seem like a day at the beach compared to what I’ll do next time.”

With that, the laughing girls sauntered off. I was left standing there—wearing only a bra, tied by my genitals to a goalpost—and surrounded by a crowd of extremely amused onlookers who showed no signs of dispersing.

Panic surged through me as I frantically began working on the knot at my groin. The yarn was tight, the fibers digging into my sensitive skin. My hands were fumbling, my fingers were shaking, and my face was burning hotter with every second that passed. The laughter seemed to intensify the harder I struggled.

Finally, after what felt like perpetuity, the knot gave way. I wasted no time. I dropped to my hands and knees and started crawling across the field. My face continued to burn as the roar of laughter followed me the entire way.

As I neared the opposite goal—it seemed I had been crawling on my hands and knees forever—I caught sight of Brenda and her friends sitting on the sideline bench eating their lunch. They were laughing heartily as they took in my humiliation.

When I reached the goalpost, I scrambled to my feet and scanned desperately for my clothes. My heart pounded. Nothing. A fresh wave of panic seized me. Then...

“Yoo-hoo!”

I turned. There was Brenda, from her spot on the bench, holding my jeans high in the air, waving them like a flag.

“Are you looking for these?” she cooed.

I groaned. Mortified, I rushed toward them, instinctively dropping my hands to cover myself. When I reached the bench, Brenda admonished me.

“Let's get those hands on your head where they belong.”

With major effort, I raised my hands to my head. The girls, sitting at eye level with my exposed crotch, took in the sight with wicked delight while I stood there, trembling. I swallowed.

“Please, Brenda... may I please have my jeans back?” I asked miserably.

"Okay, I'm almost done with you-for today," she announced. "Repeat after me: ‘You own me, Brenda, and I promise to obey you, no matter what.’ ”

"Y-you own me, Brenda," I forced out, my voice breaking, "and I promise to obey you, no matter what."

"Good boy," she praised, her smile widening. "Now say, 'I'm sooooo embarrassed. I look like a little girl. I'm wearing a bra, I have no hair on my body, and my teensy-weensy wittle wee-wee looks like an itty-bitty clitty.'"

Amid the uproarious laughter, I repeated the humiliating words. “I’m s-so embarrassed. I look... like a g—a little girl... I'm wearing a bra... I have no hair on my body... and my... teeny... little wee-wee looks like a little... a little clitty.” That was extremely difficult. But I wasn’t done.

“No, no, no,” scolded Brenda, while smiling deviously. “You have to exaggerate 'so,' like soooo. Draw it out. And you said, ‘teeny,’ and I specifically told you to say ‘teensy.’ Now try it again. Only this time, say it properly: ‘I’m sooooo embarrassed—and make sure you say it like that, with feeling—I’m sooooo embarrassed. I look like a little girl. I'm wearing a bra. I have no hair on my body, and my teensy weensy wittle wee-wee looks like an itty bitty clitty.’”

The laughter was abundant. I had to get through this latest humiliation and get the hell away from the sinister Brenda and her pack of delighted tormentors.

“I’m soooo embarrassed,” I forced out, my voice shaky. “I look like a little girl... I’m wearing a bra. I have... have no hair on my body... I’m... my teensy weensy... wittle wee wee looks like... an itty bitty...." It felt like the words were choking me. "...an itty bitty clitty.” As the words left my mouth, a fresh wave of giggles and mockery erupted around me. My face burned more intensely than ever before.

"Excellent!" exclaimed Brenda, laughing so hard she had to wipe tears from her eyes, clapping her hands for me like a delighted child. “Now just one more thing. Your other girlfriends here didn’t get to hear you sing this morning. Sing your song for us and tell us how pretty you feel.”

“Please... I—I don’t remember the words...”

Brenda’s expression darkened. “Sing, or I’ll tell Miss Farnsworth you took your pretty bra off. And you know what she’ll do.”

The image hit me like a truck. Me wearing nothing but a matching bra and panty set.

Voice trembling, I forced out the words: ♬ “I feel pretty... oh so pretty... I feel pretty and witty and gay...” ♬

"P-please..." I begged, my hands still clamped behind my head, my nakedness still on full display. "I can't remember any more..."

Brenda and the girls were laughing so hard they couldn't speak. With a final gasp of laughter, Brenda tossed my clothes at my feet. I grabbed them and bolted to the side of the bench, hastily pulling them on before marching off the field, my face as red as ever.

The rest of the day passed in a blur. I somehow survived my final two classes, returned the bra to Miss Farnsworth, and slunk away, determined to put the entire nightmare behind me.

* * * * * *

As I stepped through the doors on the final day of my sophomore year at Roosevelt High, I paused and took one last look back at the building. I shuddered.

It was clear that the limits of my humiliation had been redefined.

Never in my life had I been so relieved to see summer vacation begin.
Last edited by Blondie on Wed Sep 02, 2026 9:28 pm, edited 9 times in total.
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Roosevelt Humiliations, Chapter 10

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Chapter 10: Forced Naked at a Public Beach

Starting Puberty

I had completed my third year at Roosevelt High, and if there was one silver lining to my dismal fate, it was that I was finally starting to show some signs of physical maturity. I’d grown a few inches since my last account, and though my development still lagged well behind where it should have been for a guy my age, during the summer before my junior year I finally started sprouting some pubic hair, a change I was most grateful for.

Unfortunately, I regret to report that my growth spurt did not extend to my ability to avoid humiliation. I still have a few tales to tell, tales of fresh indignities suffered at the hands of my ever-persistent tormentors during my junior year.

Determined to change my fate, I spent the summer convincing myself that this year would be different. I resolved to stand my ground, no matter what threats they used against me. I would not be their plaything anymore. I practiced speeches in front of my mirror, imagining myself defiant and unbreakable, imagining their surprise when I finally refused to bend to their whims.

What follows is an account of how, and why, that plan failed miserably.


An Attempt at Defiance

It was only the third day of school when my resolve was put to the test. I was crossing the courtyard after lunch when I spotted Brenda and Joanna lingering near the Roosevelt statue. Our eyes met across the distance, and with a slow, knowing smirk, Brenda curled her index finger in a beckoning motion, commanding me to come to her.

For a fleeting moment, I considered ignoring her. But this was my chance to prove I was done, and things would be different from then on. This was the moment I had rehearsed for.

"Hi, Blondie," Brenda greeted me with a smile. She reached out and brushed an imaginary speck of dust from my shoulder. "It’s good to see you. We’ve missed you these last three months. The summer was so dreadfully dull without our little Blondie to keep us entertained."

"What do you want?" I asked defiantly. I kept my chin up, my shoulders back, trying to project a confidence I absolutely did not feel.

Brenda's smile never wavered. "Don’t cop an attitude with me, Blondie Boy. My shoe’s untied. Would you kindly bend down and tie it for me?”

It was a test, one designed to reassert her dominance. The command was deliberately demeaning, calculated to put me on my knees before her. But this time, I wasn't having it.

"Fuck off," I snapped. "I’m not your plaything anymore. Find someone else to humiliate."

Without another word, I turned and walked away, my heart pounding. I barely made it ten steps before Brenda’s voice rang out behind me, carrying across the courtyard.

"We’ll see what Mitch has to say about that!" she called, her tone sing-song and ominous. "You’re in trou-ble." The last word flowed mellifluously from her lips, sending an involuntary shiver down my spine despite the warm September afternoon.

For the rest of the day I was a nervous wreck. I remembered Mitch’s previous threat all too well, his promise to tie me up naked on Main Street if I ever defied him. And while he hadn’t explicitly included Brenda and her friends in that warning, it had long since evolved to include them by default. They were a pack now, and I had just challenged his niece.

Thankfully, I had arranged for a ride home with a friend that day. The moment the final bell rang, I bolted straight to his car, not bothering to stop at my locker, not daring to look behind me. He was already waiting with the engine running, and as soon as I slid into the passenger seat, we sped off into the afternoon traffic. At least for the time being, I had escaped.

That was a Wednesday. I also made it through Thursday and Friday unscathed. By the weekend, a comfortable feeling of complacency started to creep in. Maybe, just maybe, since I was now sixteen years old and a junior, they had lost interest in me. Maybe they had found a new freshman to torment.

Oh, how wrong I was.


Introducing Becky

At this point, I suppose I have no choice but to introduce another key player in the ongoing saga of the sordid humiliations I’ve been subjected to. I’ve deliberately left this person out of these accounts until now—not because she wasn’t involved, but because it hits a little too close to home. Writing about it will be painful. But maybe putting it into words will be cathartic for me.

So, here goes: The person in question is my sister, Becky.

Becky is just eleven and a half months younger than me. Because of how the school’s cutoff dates worked, we ended up in the same grade, moving through the same classes year after year. That meant we shared a homeroom, where, lucky me, she sat directly behind me, close enough that she could whisper commentary on my every humiliation directly into my ear. And let me tell you, Becky has realized considerable enjoyment over my embarrassing episodes. Whether it was Mitch, Brenda, Miss Farnsworth, or any of the other tormentors parading through my life, my dear sister took great pleasure in every single one of my humiliations.

You see, a couple of years ago, when I was fourteen and she was thirteen, I did something pretty nasty to her, and she has never forgiven me.

It was a Saturday night. Our parents were out at some dinner party, and I had a friend over. Becky was taking a bath upstairs. We’d been fighting a lot lately—nothing unusual for siblings—but that night, I decided to take things to another level. The lock on our bathroom door was one of those flimsy kinds that could be tripped with a knife. So, with my friend egging me on, whispering that it would be hilarious, that she deserved it for being such a brat, I slipped a blade into the keyhole, turned it, and with a triumphant click, the door swung open. We barged in, gazing wide-eyed at my naked sister, her body pink from the hot water.

And she lost it. I want to tell you, she screamed so loud I think the walls shook. She thrashed in the tub, kicking water in every direction, splashing it across the tile floor, onto the mirror, onto our clothes. Her voice rang through the house, and oh, did she let the profanities fly. She was swearing like a sailor. It was quite dramatic, really.

Of course, she told my parents the moment they returned, and I was grounded for the rest of the month. But that punishment hardly appeased my sister. Because Becky didn’t just want me grounded. She wanted revenge. She wanted me to feel what she had felt. She swore she would get even with me, and up until that fateful day in September, she seemed content just sitting back and enjoying my humiliations from the sidelines, watching others do what she dreamed of doing herself. But what I didn’t know was that over the summer, Becky had forged an alliance with them. She had approached Mitch with information, with access, with the kind of insider knowledge that only a sister could provide. She was soon to have the upper hand in our sibling rivalry, in a big way.


Stripped at the Beach

It was a Saturday, three days after I had dared to stand up to Brenda. It was a warm, Indian Summer type day. I had been out late the night before, and I decided to take a drive to the coast and sack out on the beach.

As I was heading out the door, keys in hand, I caught a glimpse of Becky in the living room, whispering into her phone. I didn’t think much of it at the time, but looking back, I realize now she was likely informing either Brenda or Mitch of my plans.

The beach was crowded, but I managed to find a patch of sand among a gaggle of sun worshipers. I laid out my towel, stretched out on my stomach, and let the warmth lull me to sleep.

I have no idea how long I was out before I was jolted awake. By the time my groggy brain processed what was happening, it was already too late. My arms were pinned behind my back—I found out later they were handcuffed, and I felt a sudden rush of air against my lower body, the unmistakable sensation of fabric being dragged down my legs. My swim trunks were being yanked down! They were already past my knees, and before I even had a chance to kick my legs in protest, they were pulled off my feet entirely.

To my utter horror, I was completely naked in the middle of a public beach.

"Oh shit! Oh shit!" I shrieked, my voice cracking with panic. The next few moments were a blur, but I recall scrambling to my feet in an absolute panic, my heart hammering and my mind racing for a way out, any way out. I doubled over, trying to cover myself by lifting one leg in a desperate, awkward attempt at modesty, my hands cuffed uselessly behind me.

The first faces I saw were Mitch, Becky, Brenda, Marcia, Joanna, and Cheryl. They were standing over me, grinning. I whipped my head around, searching for an escape, but there was nowhere to hide. The beach stretched in every direction, packed with witnesses. My only two options were a mad dash to the ocean or a frantic sprint to the bathroom, both of which meant running fifty yards past dozens of beachgoers who had definitely noticed the commotion, who were already turning to stare, already starting to laugh.

I chose the bathroom. Eyes locked straight ahead, I took off, refusing to make eye contact with the countless amused spectators. Not that it mattered—I felt their stares. I heard their laughter. The sound of it still haunts me to this day. I ran as fast as I could, my body hunched forward, knees pressed together in a futile attempt to preserve what little dignity I had left. In retrospect, that ridiculous posture probably just made things even funnier for everyone watching, emphasizing my nakedness rather than concealing it.

Mitch and the girls weren’t just watching. They were running alongside me, howling with laughter, savoring every second of my humiliation. Even now, I shudder when I replay the moment in my head. And I always hear the laughter.


Temporary Sanctity

At long last, I reached the stairs leading to the bathroom. I took them two at a time, desperate for refuge. I felt a surge of relief when I found an unlocked door. I rushed inside, ready to shut out the world. But before I could slam the door shut, Mitch and the girls barged in after me, locking the door behind them. I collapsed onto the toilet seat, folding myself up, my chest pressed to my knees. Laughter echoed around me as my tormentors reveled in the spectacle they had just witnessed.

“Please!” I cried out. “Unlock these handcuffs and let me get dressed!”

“We’ll do that, Blondie,” Mitch drawled. “But you’re gonna have to do what we tell you from now on. No more attitude. Or it’s just gonna get worse. You understand me?"

“Okay, okay!” I hastily agreed, on the verge of tears. “Just let me get dressed so I can go get my keys and go home. I'll do whatever you want."

Mitch nodded. "Fine. Give Blondie his swimsuit, Becky," he said as he produced a key and unlocked the handcuffs.


The Swimsuit

I exhaled in relief as my hands came free, using one to cover myself while reaching toward Becky with the other. She rummaged through her bag, grinning mischievously.

“Hmm,” she hummed, pretending to search. "Now, where did I put those trunks? I know I packed them. I was so sure I had them right here."

I swallowed hard, my stomach twisting into knots. Finally, she pulled out a swimsuit, but to my horror, instead of my swimming trunks she dangled a neon yellow bikini in front of me. I recognized it immediately as one of Becky's own, probably packed specifically for this moment.

“Here you go, Blondie,” she chortled. "This color should really bring out your eyes. And your... other features." The room erupted in laughter.

“Come on, I can’t wear that!” I protested. “Please, just give me my trunks.”

Becky smirked and tossed the swimsuit at me. “Suit yourself, Blondie. Get it? Suit yourself?” She giggled at her own pun. "Hahaha! Either way, you're going back out there with us, whether it's in this or your birthday suit. Your choice."

“Make it snappy,” Mitch added, folding his arms.

I stared down at the bikini lying at my feet, my entire body stiff with dread. The thought of stepping outside naked again was unbearable. I looked down at my feet, where the swimsuit lay on the ground. I shook my head at my desolate situation. I still had to go back to the beach and get my keys, knowing it would be futile to ask any of them to retrieve them for me. No matter how I sliced it, my humiliation was going to be monumental.

I hesitated too long. Mitch grabbed my elbow. “All right, that’s it. We’re going out.”

“No! Okay, okay—I’ll wear it!” I yelped, yanking my arm free from his grasp.

I suppose my decision was made for me. Resigned to my fate, I turned my back to them, my heart racing as I reached for the bikini bottom. Grimacing, I slid it up my legs, cringing as the spandex clung to my hips like a second skin. I welcomed the coverage, even if the femininely styled hipster would not have been my first choice.

I glanced down at the top, then turned to face my captors, pleading. “Please, can I just go like this?”

“Oh, I don’t think so,” Becky cooed, plucking the bikini top off the ground. “It’s a matching set, sweetie.”

She spun me around, deftly sliding the spaghetti straps over my shoulders. I felt the ties tighten across my shoulder blades as she finished it with a neat, feminine bow.

“There,” she said cheerily. “This isn’t a topless beach, silly girl. Everyone would see your little boobies.”

The room burst into laughter once more, while Becky grabbed my shoulders, turning me to face the mirror above the sink.

“Check it out, sweetie. You look hot!”

I groaned. “Oh, shit.” My face burned crimson, nearly as bright as the neon suit itself. The spandex clung too well, outlining everything I wished remained hidden. I looked down in horror.

“Oh, God,” I muttered.

The room erupted again as the group followed my gaze. I tried to convince myself that it wasn’t so bad, but realistically I knew otherwise. I squeezed my eyes shut and took a deep breath. I had to do this. Just run, I told myself. The faster you move, the sooner it’s over.

I cracked open the door. The beach was still packed. I took a deep breath, steeling myself, then bolted.

“Don’t even think about taking your top off!” Mitch’s voice boomed behind me.

A roar of laughter and cheers followed as I tore down the stairs and sprinted across the sand. Mitch and the girls clapped and hooted, ensuring that everyone looked. I heard the gasps and the uproarious cackles. I even heard a couple of wolf whistles. I didn’t dare look at anyone. It’s hard to say which was worse, the swimsuit or the nudity. I wouldn’t wish either on anybody.

I reached my destination, only to realize—oh shit, my keys and towel were gone! Panic surged through me. I ran in frantic circles, searching. Then I heard Brenda’s voice.

“Yoo-hoo, Blondie!” I whipped around. Twenty feet away, Brenda was leaning against a lifeguard stand, twirling my keys around her finger. “Looking for these, sweetie?” she teased, her eyes dancing.

"Come on, Brenda! Give them back!" I shouted, my voice cracking with desperation.

"You look so cute! Do a little twirl, then you can have your precious keys," laughed Brenda.

I lunged toward her, and she took off running. For the next minute, I chased her across the beach, dodging sunbathers, while she shrieked with laughter. Finally, I managed to tackle her, our momentum sending us rolling into the hot sand. I pinned her wrists with my knees, prying the keys from her grip.

"Help! Help!" she howled at the top of her lungs, making no effort to actually escape. "I'm being attacked by a lesbian!"

The entire beach erupted in hysterics. People were doubled over, pointing and clutching their stomachs as they took in the ridiculous scene. Their day at the beach had become quite memorable.


A Most Embarrassing Drive Home

Alas, I was free. I shot to my feet and sprinted toward the parking lot. By the time I reached my car, I was breathless and shaking. My fingers fumbled, dropping the keys twice before I finally managed to unlock the door and collapse into the driver's seat. I exhaled in relief—until I turned to the passenger seat.

Becky was sitting there, grinning like the devil.

“Well, what are you waiting for, sweetie? Take me home.”

“Becky, please,” I begged. “Do you have my trunks?”

She smirked. “I sure do, brother dear—or should I say ‘sister' dear?” She giggled to herself. "If you’re nice to me on the way home, maybe I’ll give them back before we go inside. I think Mom’s home—she'd love to see you like that. She always wanted another daughter.”

"That's not funny," I groaned.

Then Mitch appeared at Becky’s open window. “See you girls around!” He cackled, then added, “Make sure she keeps her top on till you get home.”

“Oh, that’s the plan,” Becky beamed. "Wouldn't want her getting arrested for indecent exposure."

He laughed, slapping the roof of the car. "Drive safe, ladies!"

I sped away, tires kicking up sand, Becky snickering beside me. She never stopped watching me, her grin smug and triumphant. I’m sure she felt vindicated from the time I walked in on her while she was in the bathtub.

At one point, she reached over and ran a hand up my leg. “When was the last time you shaved?” she teased. “Maybe we should do that when we get home.”

I flinched, praying she wouldn’t follow through with that disturbing notion. I had finally sprouted some hair on my body, and the thought of losing it was very unsettling.

Then we hit a stoplight. I ducked low in my seat, terrified of being seen. Becky caught it immediately.

“Sit up, Blondie, or I’ll have you get out and model for everyone.”

"Becky, come on, there's a truck right next to us," I whispered urgently.

"Sit. Up." She enunciated each word emphatically.

I sat up, trying to convince myself that the truck driver wouldn't notice me. I just stared straight ahead, my face flushing brightly.


The Gas Station

Becky leaned toward the gas gauge. “Oh,” she said innocently. “We’re low on gas. Better stop at the next station.”

“No... we can make it home," I answered anxiously.

“Nonsense, dear bro. Mom and Dad don’t want an empty tank. There, pull into that Fast Gas.”

I shot her a pleading look. Becky just grinned. Heart hammering, I pulled into the station and up to a pump. Again I looked at her pleadingly.

“Well, what are you waiting for?” she asked with an impish grin on her face. She held out our parents’ credit card. “Fill it up.”

I knew resisting would be futile. With a deep breath, I snatched the card from Becky’s hand, my eyes darting nervously around the gas station. At that moment, it was empty—no witnesses yet. If I moved fast, I could be back in the car before anyone noticed. I stepped out, shivering despite the heat.

Oh, God.

I jammed the card into the slot and fumbled with the pump. Then, just as I started fueling—a car pulled up at the next pump.

“Oh, shit,” I groaned under my breath. I risked a quick glance over my shoulder. A plump brunette in her early twenties stepped out of the driver’s seat. Worse yet, there was another woman in the passenger seat. At first, they didn’t seem to notice me, but I knew that wouldn’t last. My best bet would be to sit in the car until the gas was finished pumping. I shuffled toward the door, ready to duck inside—but the second I reached for the handle... CLICK! Becky had locked it. I whirled around to see her grinning at me from inside, laughing so hard she had to hold her stomach.

“Becky, please!” I pleaded, knocking frantically on the window. “Let me in!”

"What's the magic word?" she called through the glass, cupping her hand to her ear.

"Please! I'm begging you!"

"Louder!"

"PLEASE!"

Of course, that only succeeded in attracting attention to myself. I winced as I heard the brunette call out to her friend. “Hey, Tina, you’ve gotta come check this out!”

The passenger door of their car opened, and a woman with purple-streaked hair stepped out. She took one look at me and smirked. “Oh, how darling!” she cooed. “Look at you! That swimsuit is just adorable." She giggled to herself while continuing to stare at me. “And such a pretty girl. Hey, do you want to join us for a threesome, sweetheart?”

Great, now I have a couple of lesbians harassing me.

I clenched my teeth and ignored them, hurriedly pulling the pump out and shoving it back into its holder, my face practically glowing with embarrassment.

"Aw, don't be like that," the brunette called out. "You look like you'd be fun. What's your name, cutie?"

"Yeah, tell us your name," Tina added. "Don't be shy, sweetie."

"Oh, she's playing hard to get," the brunette teased. "I love a challenge."

I lunged for the car door again, yanking on the handle desperately. “Becky, please! Let me in!” I begged, pounding on the window. "Come on, you fucking bitch!"

That was a critical mistake. Becky calmly reached into her purse. She pulled out a twenty-dollar bill, then cracked the window just enough to slip it through.

“Not until you buy me a Diet Coke,” she said.

“Oh, shit, no! Please, Becky, I’m sorry. Please let me in! I apologize!” I screamed, ignoring the money.

Becky didn’t budge. “Oh, and some tampons, too.”

“Oh, God,” I whimpered, yanking the bill from her hand. I bolted toward the convenience store, racing past the two women, who were now howling with laughter.

A young, pretty, Black girl was behind the counter. She was in the middle of sipping a soda when she saw me. She froze, her mouth slightly open, before breaking into a wide, amused grin. I kept my head down and beelined for the refrigerators, my bare feet slapping against the linoleum. I grabbed the first Diet Coke I saw. That part was easy. But I was having considerable trouble with the second part.

“Where are your tampons?” I called out breathlessly.

The girl behind the counter completely lost it. She doubled over laughing, shaking her head as if she couldn’t believe what she was seeing. She tried to answer but was gasping for air through her giggles. Eventually, she just pointed to the aisle next to me, her arm waving vaguely, unable to get a word out. It was another excruciating minute before I found them. I snatched one of the boxes, nearly tripping over myself as I ran to the counter.

"Found everything you need, honey?" she managed to ask, wiping tears from her eyes.

I slapped the twenty onto the counter. “Keep the change,” I blurted out, but then hesitated. "Actually, I better get the change.”

The cashier, still grinning, looked me up and down with obvious delight, shaking her head in amusement as she handed me the change.

"You have a good night, baby," she managed. "And good luck."

Throughout the exchange, she never stopped laughing, and was so flabbergasted that she barely got those words out.

I dashed out of the store, and sure enough, the two women were waiting for me. They greeted me with more laughter, and one of them threw in a wolf whistle for good measure.

"Call us if you change your mind about that threesome, princess!" the brunette called out.

Blushing crimson, I dashed past them. I mean, I couldn’t get to the car fast enough. I yanked on the handle, expecting resistance, but thankfully, Becky let me in. I threw the bag onto Becky's lap before collapsing into the driver's seat.

Becky was howling. She had tears in her eyes, streaming down her flushed cheeks. “Oh, brother Blondie, that was a riot! Wait ‘til Brenda and the gang hear about this!” I groaned and peeled out of the gas station like there was no tomorrow.

We drove in silence for a minute—well, I was silent. Becky, on the other hand, kept giggling to herself, replaying the scene in her head with obvious relish. Every few moments, she’d look at me and smile. I just stared straight ahead, still breathing heavily. My face was still burning.

We made it the rest of the way without incident—that is, until we got home.
Last edited by Blondie on Wed Sep 02, 2026 9:29 pm, edited 7 times in total.
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Re: Roosevelt Humiliations

Post by TeenFan »

This is probably my favorite chapter I've read in a Blondie story so far. It feels more real, this chapter does.
Having to buy tampons at a convenience store, while wearing his sister's bikini is good enough to be a stand-alone short story.
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Roosevelt Humiliations, Chapter 11

Post by Blondie »

Image

Chapter 11: Maternal Discipline

Swimming Trunks Not Forthcoming

When I pulled into the garage, I turned to Becky with a pleading look, hoping—praying—she’d finally hand over my swimming trunks. But Becky had other plans.

“I’ll take my swimsuit back now, please,” she said, holding out her hand with an expectant wiggle of her fingers.

I shifted in my seat. “Can you, uh, give me my trunks first? You can go inside—I’ll just change here in the car and bring them in.”

Becky tilted her head, amused. “Oh, Blondie. Let’s get a few things straight. One, you’re not exactly in a position to negotiate, especially in that getup. You have zero leverage. None. Zero. And two, I let you borrow my swimsuit out of the goodness of my heart, so you wouldn’t have to go back out on the beach flashing your little bits to the entire shoreline. You're welcome, by the way. And three..." She paused, smiling at me. "You never even thanked me.”

She looked at me expectantly.

I blinked, genuinely caught off guard. "Are you serious?"

“I’m waiting,” she sang.

“Thank you,” I muttered, defeated.

“For what, sweetie?”

I squeezed my eyes shut. “Thank you for loaning me your swimsuit.”

“You’re welcome,” she said with a wicked grin. “Now please give it back."

Resigned, I started peeling off the swimsuit top.

"May I please have my swimming trunks?" I asked as I handed her the discarded top.

"In due time," she responded. "But first I want the rest of my swimsuit back."

"Come on, Beck. Can you just hand me my trunks first? I'll give you the bottoms, I promise. I just want something to—"

She didn't argue. She didn't even look at me. Instead, she leaned across the center console and slammed her palm against the horn. A long, loud BLAAAAAAT filled the garage, reverberating off the concrete walls. I practically leapt out of my seat.

“Jesus, Becky!” I swatted her hand off the horn in a panic. “Okay! Okay, I’ll do it! Just—what if Mom or Dad came down?"

“Dad’s playing golf,” she said. But Mom’s car is right there,” she said, nodding toward the sedan parked next to us. “And she’s got really good hearing. So... do you want to keep arguing, or do you want to give me my bottoms back before she decides to come see what all the noise is about?”

Right on cue, the door at the top of the stairs creaked open, and my mom's head poked out. “Is everything okay down there?”

"It’s fine, Mom! Totally fine!” I yelled anxiously through the window, my voice cracking on the second "fine." “I hit the horn by accident!”

“Oh, alright,” she said. Then she paused, squinting into the dim garage. “You know, you really should wear a shirt when you’re out and about. It’s just more... appropriate. More decent.”

“Yes, Mom. Got it. Shirt next time,” I said, trying to shrink into my seat.

She kept squinting. “Is that a new swimsuit? I haven’t seen that one before.”

“Uh... yeah. It’s new.” I lowered my hands to my lap in a hopeless attempt to cover myself.

"It looks small from up here. Are you wearing a Speedo?"

I groaned and glared at Becky, who was clearly on the verge of losing it entirely. Her whole body was shaking with suppressed laughter,.

“No, Mom. They’re just... a little smaller than my old trunks.”

"How was the beach?" she asked.

Oh, for fuck's sake! Can you just go back in the house? Please?

Then Becky rolled down her window.

“No! Becky, please,” I whispered, panicked.

“It was very interesting, Mom,” she called out. “Blondie was the star of the beach today. He gave quite a performance. Really memorable.”

"Oh, really," answered our mom, her curiosity clearly piqued.

“Oh yeah. Everyone got to know him really well. You should’ve seen him. I think he thought we were at a nude beach, the way he was carrying on."

"Whaaaat?" My mom's jaw dropped, her eyes widening.

"Oh, shit!" I whispered, my face burning "Becky! Knock it off!"

“I mean, not literally,” Becky said with a shrug. “But Brenda got mad at him, and they ended up wrestling. Blondie tried to yank off her top, and actually exposed her boob for a second. In front of everyone!”

"Oh my God!" Mom gasped, her hand flying to her chest.

“I—I wasn’t trying to...” I stammered.

“Well," Becky said, ignoring my pathetic protest, "Brenda got even. She pulled his trunks down to his knees. Fair's fair, right?"

“Oh, for heaven’s sake, Blondie,” my mom muttered. “What in the world is the matter with you?”

“I wasn’t—she just...” I buried my face in my hands, wishing I could melt into the seat.

“Well, it sounds like you got what you deserved,” Mom said briskly. "I'll bet you were pretty embarrassed."

"Oh yeah," said Becky. "Blondie was embarrassed, alright. Brenda had him in a hold and turned him face forward. His little bits were out there for all to see."

"Oh, my," said our mom. "Well, it serves him right. Blondie, I'll deal with you later," she said, as she disappeared and closed the door.

I bowed my head and had one hand over my eyes, shaking my head slowly.

“Well, that was fun,” Becky said, wiping tears from her eyes. "God, the look on your face was priceless. I wish I would've recorded it."

"Son of a bitch! Please, can I just get my trunks?" I asked.

“Not until I get my swimsuit back,” she said again, smugly.

Resigned, under Becky's watchful, amused gaze, I started shimmying out of the bottoms. The material caught on my hips, and I had to wriggle awkwardly to work it down. From my standpoint, Becky was attaining way too much enjoyment from watching me strip at her behest.

"You know what's pretty cool?" she asked as I pulled the garment down my legs. I didn't answer, but that didn't slow her down. "We’ve reached a new stage in our relationship. I officially own you. I snap my fingers, you jump. I want you naked? You’re naked. Anytime, anywhere, at my pleasure. It's honestly pretty awesome." She leaned back in her seat with a smile of smug satisfaction. "I should've started doing this a long time ago."

I groaned and slipped off the last of the swimsuit and handed it over to Becky.

“Please, now may I have my trunks?”

Just then Becky's phone pinged a few times in succession. She looked down and smiled.

“Becky, come on. Please.”

“Hold on. The group chat is blowing up. Brenda, Joanna, Mitch... they want an update.”

"Please, Beck. Let me get dressed!"

She ignored me. “I just told them we’re in the car in the garage, and that you’re naked."

She held up the phone to me. CLICK. "They wanted proof," she grinned.

I sat there and listened to many more pings while Becky continued to text.

“Jesus Christ,” I groaned.

At last, she reached into her bag and pulled out my trunks. I reached for them—but she pulled them back at the last second, holding them just out of reach.

“I’ll just leave these on your bed,” she said, popping her door open.

“No! Becky, please! What if Mom sees me?”

"Well, she probably already thinks she brought up some kind of pervert," Becky shrugged. “She's still mad at you for walking in on me while I was in the tub. And now she thinks you were trying to take Brenda's top off." She grinned. "Besides, what's the big deal? She's seen you naked more than anybody."

"But... that was a long time... this is different!"

"Well, you best avoid her then,” she said, hopping out of the car. “And don't you dare try to cover yourself with something in the garage. I'd better see you running into your room naked. And it better be soon, or I'll have to text Mitch and tell him you disobeyed me."

She smiled and trotted up the stairs, my trunks dangling from her hand. And just like that, she vanished, leaving me alone, naked, humiliated... and completely under her thumb.


Making a Run for It

I sat there, naked—oh, so naked—for a minute or two, trying to build up the courage to go inside. Finally, after one last deep breath, I opened the car door and crept out, my bare feet touching the cold cement. After climbing the stairs, I opened the door to the house with excruciating care and peeked inside. I breathed a sigh of relief to see that my mom was nowhere in sight. I could hear her in the kitchen, though—moving around, humming to herself, the sound of dishes being stacked.

That was my window. Ahead of me stretched a long hallway leading to the living room and the staircase to my room. Halfway down the hallway was the open doorway to the kitchen. I’d have to sprint past that opening and up the stairs and hope to hell that she wouldn't see me.

I slipped inside, quietly shut the door behind me, and took off like a shot.

I thought the odds were in my favor.


Spotted by My Mother

Ten feet in, those good odds turned 100% against me. Just before I reached the kitchen doorway, my mom stepped casually into the hallway, a dish towel in one hand. Her nonchalance lasted exactly one second—right up until she turned and saw her sixteen-year-old son frozen in place like a deer in headlights.

Her sixteen-year-old son who was naked.

She blinked. Her eyebrows shot up. “Blondie?”

When I saw her, I stood momentarily frozen, not knowing which way to turn. Instinctively, I clapped my hands over my modesty, though I had the sinking feeling she might have already caught a glimpse of something she hadn’t seen since I was a young child. I could feel the heat rising up my neck.

Her voice echoed in the hallway. “Why are you naked, Blondie?”

“I, uh... it’s a long story...” I was already turned away, aiming for the garage again, when she switched from surprised to stern.

"Hold it right there, young man!" she bellowed.

Now, my mother is normally as nice as can be, but during the rare times when her ire is up, when someone has truly crossed her line, she can be absolutely authoritative. I knew from her tone of voice that this was one of those times. I stopped in my tracks, my bare ass facing her.

“Turn around,” she said firmly.

“Mom, please...”

"Turn. Around." She spaced the words deliberately, leaving no room for negotiation. I turned slowly, miserably, still shielding myself with both hands. She crossed her arms and gave me a long, deliberate once-over. “You stay right where you are,” she said, pointing at me for emphasis. “Don’t move.”

She walked briskly into the living room and called up the stairs. “Becky! Come down here, please!”

I groaned inwardly. I knew immediately where this was going, and it didn't bode well for me. Not well at all.

It all went back to the time I had intentionally walked in on Becky while she was taking a bath. My mom was pretty upset with me, and even though I was grounded for the rest of that month—my dad decided on the discipline—I don't think she felt that the punishment fit the crime. Being of the female persuasion, she had felt more empathy for Becky's violation of privacy than my dad or I did. Compound that with Becky's bogus story about how I tried to yank Brenda's top off at the beach—well, I had a hunch that she planned on teaching me a lesson. The poetic justice variety.

Becky must have been listening at the top of the stairs, because she was down in a heartbeat. She followed Mom into the hallway, both of them stopping a few feet in front of me.

“Oh my God, Mom!” Becky said, staring at me with an impish grin. “Why is Blondie naked?”

I might have tried to strangle her if I wasn't in the predicament I was in.

“I've been wondering that myself,” Mom said coolly. “But that’s not the important part. The important part is that he is naked, which is why I called you down here."

"I'm glad you did, Mom," said Becky as she stared at me, grinning. "Very glad."

Meanwhile, I'm still crouched over, with my hands firmly clenched to my groin.

"Yes, well," my mother continued, "Blondie's reprehensible conduct when he and his friend purposely walked in on you while you were in the bathtub... well, let's just say that this is his moment of reckoning. His comeuppance, if you will."

"Thank you, Mother. This does make me feel a little better, though the scars from that day may never totally disappear."

Oh, please, just stop.

"I know, dear," she said while putting her arm around Becky and giving her a squeeze. "But I hope this helps. Closure is important."

They were both quiet for a moment as they continued to stare at me, taking in every detail of my exposed skin.

"What shall we do with him?" asked my mother, her tone almost conversational, as if she were discussing what to order for dinner. "Will this be good enough for you, or is there something else you'd like?"

DO with him? Something else? What the fuck?

"Well, now that you mention it," responded Becky, "there is something. When he barged into the bathroom that night, he really got an eyeful. I happened to be washing my hair at the time, so I had my hands on my head... and I was fully exposed. Completely vulnerable."

Becky left that out there so my mom—and I—could digest the implications of her statement.

"Yes," said my mother thoughtfully. "I do see what you mean. He saw you in all your glory—sorry, Becky, I know it's hard for you to have to look back on that dreadful experience—whereas Blondie...” She glanced down at my crotch. “Even though he’s naked... he saw a bit more of you than what you're seeing of him right now. He's still hiding behind his hands."

"Exactly," said Becky. "You really do understand, Mom."

"What's good for the goose is good for the gander, right?" said our mother.

“Yes! And I’d very much like to take a gander at his goose!” Becky shot back.

They both laughed lustily, the sound filling the hallway, while I stood there immersed in my wretchedness, my face burning.

"Oh, that's a good one, Becky!" laughed my mom. "A very good one."

Once their laughter died down, Mom turned to me with a calm but deadly kind of authority.

“Blondie, if you really want to show you're sorry—and I mean truly sorry—then you’ll stand up straight and put your hands on your head.”

I flinched. “What?! No! That’s going too far!”

“You didn’t think it was going too far when you burst in on your sister during her bath?” Mom replied.

“I didn’t even see that much!” I protested weakly.

Becky gave me a look of pure disbelief. “Please. You walked in gawking at me like your eyes were about to pop out of your head.”

“I just—it wasn’t like that! Please, can I just go get dressed?" I pleaded. "I'm really sorry for what I did, and... and I was already punished for it. Dad grounded me for almost a month!"

"Yes, but I never thought your punishment was harsh enough," said my mother. "Considering how shameful your action was, I think you deserve to feel some shame yourself. And Becky deserves to witness your shame, after the way you violated her privacy."

I glanced at Becky, whose smirk seemed to be permanently plastered on her face.

“Now,” Mom continued calmly, “I’d like you to remove your hands from your privates and put them on your head.”

It looked like I was actually going to have to go through with this. That being the case, I had to at least try to modify the conditions. The idea of exposing myself to my mother added a whole new layer of humiliation to the scene.

“Mom... please,” I said desperately. "Can I... if I have to do this... can you please go away so just... just Becky will see? Please, Mom. I'm begging you."

She considered that. "Hmm, I do understand," said my mom, and for a moment I dared to hope. "You are a little old to be displaying yourself to your mother like that. Sixteen years old, practically a man. But that puts me in a bit of a quandary. The whole point of this little punishment is to shame and embarrass you the way you embarrassed Becky. To give you perspective."

No! No quandary! You walk away, Becky looks at my dick again, and we're done with this madness.

She paused, then turned to my sister. "What do you think we should do, Becky?" she asked.

Oh, shit. You're leaving it up to HER? What the hell do you THINK she's going to say? Have you met her?

“Well,” Becky said thoughtfully, “I do agree that after what he did, we need to embarrass him properly. And he is sixteen years old... so I think having his own mother see his bare privates would be very embarrassing for him.” She giggled. “And honestly, I already caught a glimpse of his little bits when Brenda pulled down his trunks at the beach. So I understand why he wouldn’t want anyone seeing what he’s got down there... or what he doesn’t have, to be more accurate.”

She paused, and a faint smirk appeared on my mother's face. To my detriment, Becky wasn't finished.

"But don’t forget," she added. "Blondie had a friend with him when he walked in on me. That means there were two witnesses to my nakedness.”

Oh shit, I think that sealed it.

"That's a very good point," our mom said, predictably. "So you think I should stick around and witness his shame."

"I do, Mom. One hundred percent."

"All right. A witness I shall be. Blondie, let's get those hands on your head."


Exposed and Teased

"Mom, please..." I begged, my voice cracking.

"NOW!"

Her authoritative voice echoed throughout the hallway, with that unmistakable do-not-test-me finality. My hands shot up to my head. I stayed hunched over, legs tightly crossed in one last act of desperation, my body angled to preserve some modicum of coverage.

Becky grinned unabashedly at my posture and my nakedness. "Can you get him to stand up straight and spread his legs?" she asked. "We can't really see anything."

“Stand up straight, Blondie,” Mom said firmly. “And uncross your legs.”

I winced. But slowly, painfully, I obeyed. Back straight. Feet apart. Every nerve in my body screamed with humiliation as I stood there while my mother and sister stared blatantly at my exposed genitals. Both of them were smiling with no shame—just open, unrestrained amusement at my expense.

After a long, tormenting silence, my mother spoke. "I see what you mean, Becky," was her biting remark, still staring.

“I know, right?” Becky giggled. "It's pretty small. No wonder his face is so red."

The humiliation was excruciating. I groaned softly and resisted the urge to bury my face in my hands—which, of course, were still locked up on top of my head.

I expected Becky to be soaking up every second of my misery—of course she would—but what unsettled me even more was seeing how much my mother seemed to be enjoying it too, watching me with that same faint, amused smile.

It took everything I had not to turn and bolt straight back into the garage. But I knew defying Mom would only make things worse. And besides, I had the faint sense that this would all be over in a moment.

That sense turned out to be... incredibly naive.
Last edited by Blondie on Wed Sep 02, 2026 9:29 pm, edited 7 times in total.
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Roosevelt Humiliations, Chapter 12

Post by Blondie »

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Chapter 12: A Very Embarrassing Spanking

Another Witness to My Humiliation

As I stood naked in front of Becky and my mother, I was dearly hoping that my mortifying ordeal would soon end, and that I could escape to the sanctuary of my room. But then... the doorbell rang.

I froze, eyes wide. The three of us exchanged open-mouthed glances. There was a momentary silence while we pondered the ramifications of someone being at the door while a naked sixteen-year-old boy was being put through his paces.

Becky broke the silence, and it gave me another start.

“Oh, that must be Brenda!” she said merrily. “Should I bring her back here?”

“No!” I yelped, horrified. "Please, no. Mom, tell her no. Please, I'm begging you!"

My mother didn’t even flinch. “Hmm... it might actually be good for Blondie to have another witness. You know, someone outside the family. After all, Becky had to deal with embarrassment in front of others too. Fair is fair.”

“No, please—Mom!” I pleaded, but my words fell on deaf ears.

Becky practically skipped off to answer the door, giddy with anticipation. That left me standing there, red-faced and exposed, with my mother eyeing me calmly like I was some art piece in a gallery. "Uncomfortable" doesn’t begin to explain how I felt at that moment.

"I know this is embarrassing for you, Blondie," said my mother. "But think of it as karma in its purest form. After your little stunt with Brenda today, I think it was fate that brought her here right now."

Or more likely a text from your diabolical daughter.

I heard Becky whispering something to Brenda at the front door. I suspect she wanted to keep their stories straight and was apprising her of the phony account of how Brenda and I got in a wrestling match and that I tried to take her top off.

My mother folded her arms, still watching me with the kind of patience that only made things worse. A moment later, the two girls returned, Brenda coming around the corner—and promptly freezing mid-step.

“Oh. My. God!” she gasped, her eyes traveling south. “Why is Blondie naked?!”

She was clearly delighted—and just as clearly, Becky had kept my nudity a secret to maximize the surprise.

"That's the question of the hour," responded my mother. “Brenda, Becky told me what happened at the beach today, and I want to personally apologize for my son's behavior.”

Brenda waved it off with a wide grin. “Oh, no worries, Mrs. Haggerty. It was definitely embarrassing at the time... but I think I’m over it now.” She turned to me and grinned wickedly, her eyes roaming over me with deliberate slowness. “This more than makes up for it. Like, way more.”

The three of them laughed, adding fuel to my persistent blush.

“Good,” my mom said cheerfully. “I thought inviting you in might provide a bit of catharsis.”

"Oh, yes, thank you! I'm feeling better by the second," laughed Brenda as she looked me up and down lewdly.

I shifted my feet, my face burning so hot I thought I might spontaneously combust.

"I'm glad to hear it," said my mom. "Judging by how red his face is, I'd say his punishment is having the desired effect."

"Oh, you're right, Mrs. Haggerty. I hadn't noticed. I couldn't take my eyes off his little bits."

Again the three of them laughed, while I stood there and soaked up the mortification.

"Yes, they are on the smaller side," noted my mom, her tone as conversational as if she were discussing the weather. "Becky and I were just remarking on that before you arrived."

Oh, just shoot me. Now. Somebody. Please!

"What do you think he's more embarrassed about," asked Becky, "the fact that he's standing there naked while we watch, or the fact that he has such a small penis?"

"I'd say both," answered Brenda without hesitation. "He'd be embarrassed either way, but it might be a little less so for him if he had a normal-size penis."

"And it must be humiliating to stand there all naked and listen to us talk about his little bits," said Becky.

"I can't even imagine," agreed Brenda. "Standing there nude and exposed while we all discuss his shortcomings. How humiliating for him."

My mother decided to join in the conversation again. Her level of enjoyment seemed to be mounting, much to my chagrin.

"Blondie," she said. "I can tell by the hair you've grown down there that you've started puberty. How long ago did it start for you, would you say?"

I really was in no mood or state of mind to partake in the sordid discussion, with my mother or anyone else. "I don't... please, I don't know. A while ago."

"There's not that much hair there," Becky interjected, leaning in for a closer look. "I don't think it's been that long."

"I can actually confirm that," Brenda said. "My brother... he must have seen Blondie in the shower at school," she said. "It was less than a year ago, and he told me Blondie was completely smooth down there. He also told me how little it was. He used the word 'tiny,' actually. I guess he brought it up because Blondie was fifteen at the time, and he thought it was very unusual and kind of amusing for a boy that age to have such small, hairless bits. Or, in his words, a hairless little pecker."

Becky and Brenda laughed, while my mother smiled. All three had their eyes focused on the topic of conversation. I wanted to die on the spot.

"I'll bet the other boys must have teased him about it," Becky said.

"No doubt," Brenda replied. "A fifteen-year-old boy with hairless little bits? I'm sure they were laughing at him, making fun of him."

"So, Blondie," my mother persisted, refusing to let the topic drop. "Would you say you started puberty sometime between your fifteenth and sixteenth birthday?"

"I... I guess," I answered softly while staring at a discolored fiber on the hallway carpet.

"It must have been difficult for you to have been fifteen years old and still prepubescent," she commented.

"Just like it must be difficult for him now, to be sixteen years old and have such tiny little bits," followed Becky devilishly.

They all burst into laughter again—my mom chuckling lightly, while Becky and Brenda nearly doubled over. I just stood there, blushing furiously.

Eventually, the laughter tapered off. My mother looked at the two girls with a satisfied smile. She seemed ready to conclude the proceedings.

“Well, ladies,” she said, “I think Blondie’s had his fair share of humble pie today. Are we satisfied with his little lesson?"

About freaking time! Let me out of here, please!

Becky tilted her head, pretending to think. "Mom, um... there is one other thing I'd really love to see you do to him..."

See her DO to me? What the fuck? Just stop it!

Our mother raised an eyebrow, her curiosity piqued. “And what would that be, dear?”

“Well,” Becky said slyly, “do you remember how you used to punish Blondie when he was a naughty little boy?”

Oh, shit. I see where she's going with this. No fucking way!

“Oh, yes,” my mother said, eyes lighting up. “I used to sit in that armless chair in the living room and give him a good old-fashioned spanking.”

“I’d love to see that again,” Becky said, her smile practically diabolical.

I turned to Becky with a horrified expression, then glanced at Brenda, who wore a lascivious grin on her face. I looked warily at my mother, who looked like she was actually considering it. I had a very bad feeling about this.

“We do still have that chair,” she mused.

"Yes, we do!" chirped Becky. "You know, you always let Blondie keep his pants on when you spanked him back then. I must confess, I've always, always wanted to see you do it on his bare bottom. Just imagine how much more effective it would be."

"Well, by golly," said my mother while looking at my midsection, "then I think it's high time that we do just that. I suppose there's no time like the present for a proper lesson."

Wait, no... you can't be serious!

“Mom! Come on, you can't be serious!” I protested, practically choking on my own words as I dropped my hands from my head. “I thought we were done here!”

“First of all,” my mom replied calmly, “I never said you could take your hands down.”

She stared pointedly until I slowly, miserably returned my hands to their designated humiliating position atop my head.

"Second," she continued, stepping closer, “we’re done when I say we’re done. Not a moment before. What you did to Becky back in the day, and then to Brenda today, absolutely calls for proper discipline. Real consequences. And thanks to your sister's helpful reminder, I agree that a spanking on your bare bottom feels perfectly appropriate. After this, I suspect your naughty streak will be thoroughly corrected.”

I stood there in stunned silence, barely able to process the absolute horror of what was apparently about to happen.

“I never told you this, Becky,” Mom said, transitioning back to a casual, chatty tone as if I weren't even present in the room, “but I actually did bare his bottom once before.” My mother looked back at me meaningfully. "I'm sure Blondie remembers it well. Don't you, Blondie?"

Of course I remember. It's not something one would ever forget.

"I'm so sorry I missed that!" said Becky, her grin stretched ear to ear.

“You were already asleep,” Mom chuckled. “Otherwise, I might have let you watch. I only gave him a spanking a handful of times, you know, and he was usually wearing his trousers. But one time it was at night, and he was wearing his pajamas, without any underwear. He was about eight or nine at the time. Anyway, he was sitting in front of the TV, and I had told him numerous times that it was past his bedtime. I gave him one last warning, and he finally got up to go to bed, but not without using some foul language. It was very unbecoming for a young child."

"So he deserved to be spanked, just like now," said Becky.

Brenda giggled. “Naughty Blondie!”

“Very naughty,” Mom said, nodding. "Well, he got my dander up, so I dragged him by the arm and put him over my knee. I spanked him a couple of times as before, and then, on a whim, I pushed his shirt up and swiped his pajama bottoms down."

"Oh, I wish you would have woken me up!" Becky lamented.

"I should have," laughed my mom. "Anyway, I’ll never forget the sound he made. He was so shocked, so completely unprepared, that he squealed like a startled little piglet."

"Oh, I love it!" laughed Becky, clapping her hands together. "I can just picture it!"

"Awesome," Brenda added, her twinkling eyes fixed on me.

“And I have to say,” my mom continued, clearly savoring the memory, “it was remarkably more effective to spank his bare bottom. The swats had a nice, crisp sound—quite satisfying, really—and I'm sure he felt them more than usual, too. That sharp sting without any clothing to dull the impact." She paused, visibly replaying the scene in her mind. "That was nice, but I guarantee you that the embarrassment of having his mother bare his bottom had more impact than any pain he felt. It's the psychological effect that matters, you see. The moment I let him up, he yanked those pajamas bottoms up like his life depended on it.”

"And his face?" Becky asked, leaning in, hungry for every humiliating detail.

"Red as a tomato," Mom said with satisfaction. "Just like it is right now.” She gave me a knowing smile while I felt my face burn even hotter.

“Did he cry?” Becky asked, grinning from ear to ear. "Did he actually cry?"

“Not loudly,” Mom said, "not heaving sobs or anything so dramatic. But when he turned to apologize, there were definitely some tears. Anyway, he certainly learned his lesson, because that was the last time I had to spank him."

"Until now," Becky corrected.

"Until now," our mother concurred, her eyes meeting mine.


The Spanking

She turned to face me and pointed toward the living room. “You know the chair,” she said, her voice calm but commanding. “The one with no arms. Go on now. Stand beside it and wait for me.”

Oh my God, this is really going to happen!

My mother stepped to one side of the hallway while Becky and Brenda moved to the other, creating a narrow gauntlet I would have to traverse. I gulped and, with my hands still obediently locked behind my head, began the mortifying march past the gleeful girls.

“Oh, the walk of shame,” Becky giggled as I passed. "Look at the naked boy go!"

"Go, Blondie! Go, Blondie!" Brenda sang, and I felt my face grow even hotter.

Their laughter floated behind me as I led them into the living room and stopped next to the infamous chair, where I stood trembling until my mother took her seat. She smoothed out her cotton skirt and looked me square in the eyes. She was ready. They were all ready.

“Assume the position, please,” she said, while gesturing to her lap.

The air in the room was electric. For the three of them—especially Becky and Brenda—it was a moment of delicious anticipation. For me, it was pure, unadulterated dread.

With a whimper of total surrender, I lowered myself across her knees. It was surreal—even though it had been many years, it was an all too familiar, ignominious position. But now it was infinitely worse, as I was completely exposed, vulnerable, with two very amused witnesses soaking in my every twitch and flinch. The fact that I was sixteen only deepened the shame. I was far too old for this—and far too naked.

I felt her use both hands to adjust my torso to her liking. A few seconds passed in absolute silence, broken only by my heavy breathing. My heart was racing, and I had little doubt the same could be said for everyone else in the room, though for entirely different reasons.

Then... SMACK! The first slap echoed like a firecracker. A split-second later, I felt the sting bloom across my backside.

“Ooh!” Becky squealed, leaning in. “Did you see him jiggle? Did you see that?”

“That definitely got a reaction,” laughed Brenda. "Look at him squirm!"

My mom settled into a steady rhythm, alternating sides as she went. Each smack prompted an involuntary twitch from me, followed by a fresh wave of giggles from the "peanut gallery" behind me.

"Ooh, it's starting to turn pink!" observed Becky after several spanks evidently had begun to leave their mark.

“I think we can do better than ‘pink,’” my mom said, unfazed, delivering another crisp swat that made me gasp. “Let’s aim for raspberry.”

“I vote cherry red!” Brenda laughed. "Oh, this is so much fun!"

The "fun" continued for a few more seconds. After a few more stinging spanks, my mom finally paused, her hand resting lightly on my heated butt cheek. I felt a slight sense of relief that my ordeal was finally over. That is, until her next utterance.

"Would you like to finish up, Becky?" she asked, her voice casual, as if offering her a cookie.

Noooooooo!

"Would I!" Becky squealed, springing into action. Before I even had time to protest, I found myself face down across my sister’s lap.

“Come help me, Brenda!” she chirped gleefully.

"Love to!" Brenda was on one knee in an instant, facing Becky across my traumatized backside.

“I’ll take the left cheek, you take the right,” Becky instructed. "Synchronized, okay? On three."

"Got it!" replied Brenda, positioning her hand. "Ready when you are!"

"One... two... three... go!" shouted Becky, and then all hell broke loose. A flurry of slaps descended—sharp, fast, and merciless. I squirmed helplessly as the two of them delivered synchronized humiliation.

“You’re missing a spot!” Becky called out mid-barrage. “Just off to the side—it’s not red yet.”

"I'm on it!" replied Brenda as she redirected her efforts. I felt the sudden sting on a previously untouched patch of skin, and I yelped despite myself. My entire backside was ablaze, and my dignity was long gone.

“Ow! Oh! Stop! Please! Mom, make ‘em stop!”

“Alright, girls," my mom finally intervened, her voice amused and satisfied. "I think Blondie has had enough. Well done—you really warmed him up nicely. Excellent teamwork.”

At last, the slapping ceased. I awkwardly rolled off Becky’s lap, clutching my scorched hindquarters with both hands.

“Owwww... Ohhh!” I yelped, hopping from foot to foot, my voice embarrassingly high and pitiful. "Oh God, oh God..."

“Mother,” Becky said, “can you make Blondie go stand in the corner for being the bad little boy he is? I remember you used to do that after his spankings.”

“Oh, absolutely,” my mother said with a grin. “That’s a fitting next step. Blondie, go plant yourself in that corner by the TV and reflect on your behavior. And I mean really reflect. Think about why you're standing there with a bright red bottom."

Still clutching my burning butt with both hands, I shuffled across the carpet until I reached the corner, then faced the wall.

“Hands on your head,” my mom added sharply.

I raised my arms slowly, locking my fingers behind my head once more. The position thrust my hips back, leaving my glowing, raspberry-colored backside completely exposed to the room. I could sense every pair of eyes on me as though they were physical touches.

“Hey, wanna watch a Seinfeld?” Becky asked, flopping onto the couch like we weren’t in the middle of the most humiliating moment of my life.

“Sure,” said Brenda.

And just like that, the three of them got cozy on the sofa. The sound of theme music filled the room, while I stood in the corner—naked, red, and utterly humiliated.

Then the doorbell rang.

Uh-oh.


Yet More Visitors

"Oh, that must be Joanna and Marcia," Becky said, and I could hear the delight in her voice as she hopped up from the couch. "I told them if they stopped by, it'd be worth their while.”

You've got to be KIDDING me!

I instinctively took a step away from the wall, but my mother’s voice cracked like a whip.

“Stay right where you are!”

“Please, Mom!” I begged, forehead resting against the wall. “Let me go before they see me! I'll be good, I promise. Just let me—"

“I don’t think so,” she replied coolly. “I’m not quite finished with your lesson yet.”

Moments later, I heard Joanna’s voice drifting in from the hallway. Footsteps approached. I held my breath, bracing myself for more witnesses to my shame.

It took her a couple of moments to notice that Becky's naked brother was in the room.

“Thanks for inviting us over, Beck. I’m really curious what you meant by—oh, my God!” The footsteps stopped abruptly. Then, the inevitable: “Why is Blondie naked?”

“He’s being punished,” Becky explained merrily. "Isn't it obvious? Look at that bottom."

“Wow, I can see that,” laughed Marcia. "Look how red his little fanny is! It's practically glowing!"

“Did you do that, Mrs. Haggerty?” Joanna asked, the amusement in her voice evident.

“Oh, I'd say we all had a hand in it," answered my mom, eliciting laughter from all.

“Come have a seat,” offered Becky. "We were just starting a Seinfeld. The one where they go to the Hamptons, actually."

"Sounds good," said Joanna. "Though I think watching your brother might be more entertaining."

More laughter ensued, and I was forced to stand in the corner with my naked, glowing backside serving as side entertainment (well, more likely the entertainment) as they watched the episode.

The mockery didn’t stop there. Of all the episodes in the series, it had to be the one in the Hamptons—the "shrinkage" episode. George is changing after a swim, and the woman walks in on him while he was fully exposed. She looked down at his penis and grinned while putting her fingers to her lips.

“Still probably bigger than Blondie’s,” Brenda said.

Laughter exploded around the room. I closed my eyes, squeezing them shut. My face, though unseen, was burning just as hot as my ass cheeks.

Eventually, the episode ended, and my nightmare drew to a close.

“Okay, Blondie, you can go get dressed now,” said my mom, finally taking mercy. “Say good-bye to our guests and go on up to your room.”

“Bye,” I muttered, shielding myself with both hands as I made a break for the stairs, desperate for the sanctuary of my room.

“Blondie!” my mother called sharply. “Don’t be rude. Turn around and thank them properly.”

I froze, turned slowly—thankfully she didn’t make me move my hands—and managed to choke out, “Thank you for coming.”

“No, thank you,” Marcia grinned.

“Yes, the pleasure was all ours!” Joanna added. "We'll have to do this again sometime."

I fled up the stairs, the sound of five delighted females laughing behind me echoing in my ears.


Owned by My Sister

About an hour later, my bedroom door creaked open. I looked up from where I lay on my bed to see Becky standing in the doorway, her arms folded and a smug little smile on her lips. Normally, she'd have knocked, but apparently, that ship had sailed.

“I own you now, Blondie,” she said simply. "Just think about that. Every time you look at me, every time you hear my voice, remember who decides what happens to you."

She didn't wait for a response; she didn't need one. She simply turned and closed the door softly behind her.

As I lay face-down on my bed, still feeling the sting of the afternoon, I mulled over her words.

Much to my dismay, I realized they were oh, so true.
Last edited by Blondie on Wed Sep 02, 2026 9:29 pm, edited 9 times in total.
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Roosevelt Humiliations, Chapter 13

Post by Blondie »

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Chapter 13: Under My Sister’s Control

Becky’s Dominance

I know it’s been a while since I chronicled my last series of public disgraces at the hands of my sadistic tormentors. You see, it is quite difficult for me to recount these episodes, as my humiliation intensified throughout my junior year. But I'm hoping it will prove therapeutic to continue with this account, so I'll trudge on, however reluctantly.

As you may recall, my darling sister Becky had recently joined forces with Brenda, Mitch, and the rest of the gang in the ongoing campaign to destroy every shred of dignity I had left. Ever since that alliance formed, Becky has been a persistent thorn in my side. She still refused to let go of that ancient incident when my friend and I barged in on her while she was taking a bath. That experience has really stuck with her, and she has been taking great pleasure in her retribution now that she holds the upper hand.

She didn’t waste any time flexing her newfound dominance over me, either. It was the morning after my mortifying experience at the beach, the gas station, and that god-awful encounter with our mother that makes me cringe to this day. I was in my room, trying to decompress, quietly reading the sports section, when suddenly, without knocking, Becky let herself in.

“Brother Blondie,” she said, “would you be a dear and clear my breakfast dishes off the table and wash them for me? Oh, and when you’re done with that you can go make my bed. I'd do it myself, but you know how busy I am.”

I stared at her, wide-eyed, clinging to the faint hope that she was merely joking. But that was wishful thinking.

"But..."

“No ‘buts,’ my little pet," she interrupted. "I own you now. And unless you want to end up stark naked in public again—and believe me, I have plenty of ideas for making that happen—you'll do exactly as I say." She stepped closer. "I’m going on a bike ride, and when I get back, I expect my chores to be done. Oh, and since you put up a fuss just now...” She smirked, clearly pleased with herself. "...you can clean up the mess I left in the bathroom, too. I swear, whenever I brush my hair, half of it ends up all over the sink. The whole thing's a mess. And the toilet needs a good scrubbing, too. Make sure you scrub underneath the lip. It's absolutely disgusting down there."

She turned to leave, then paused in the doorway, with one hand on the frame. “Oh, and I noticed there are a couple of stray pubic hairs on the floor. They must be mine, ‘cuz they’re definitely too long to belong to you." She giggled at her own joke. "I don’t want to see those when I get back. You’ll also find a pair of my panties on the floor. Kindly place them in the hamper." My mouth opened, but she cut me off with one last zinger. “And if I hear even a whiff of backtalk, you’ll be wearing them to school tomorrow." She paused and smiled to herself. “Now that I think about it, I bet you’d look adorable in my panties. Maybe with a little bow in your hair to match.”

Without waiting for a reply, without giving me any chance to process the horror of her threat, she disappeared, her laughter resonating through the hallway. My little sister had become an absolute monster.

So yeah, I did the chores. What choice did I have? I washed her dishes and made her bed, trying not to think about what I was doing. Then, I tackled the bathroom. Hair everywhere, just like she said, long blonde strands clogging the drain. The toilet. And of course... the panties. I found them on the floor where she had dropped them. I picked them up with my thumb and index finger, holding them as far from my body as possible, and with my arm outstretched I carried them through the hallway to the hamper like they were contaminated. I shuddered while recalling her threat to make me wear them to school. And I couldn’t shake the horrifying thought that she might actually make good on that threat. That somehow I’d find myself being asked to show them off to anyone curious.

It was official. I was completely at her mercy, and we both knew it.


Lacy Anklets

For the next few weeks, Becky kept me firmly under her little thumb. I was her go-to elf, her personal servant, expected to hop to attention anytime she needed something done, no matter how trivial or demeaning. She told our parents I'd lost some kind of bet, which somehow they accepted without question.

As much as I hated doing my sister’s bidding, I took comfort in one thing: At least she hadn’t subjected me to any new, major public humiliations. A little scrubbing here, a little fetching there—yes, it was degrading, but it didn't compare to the catastrophic humiliations I had suffered through during the summer. Those memories still haunted my dreams.

But it all came crashing down one Saturday in late October. Our parents were away for the weekend on some couples retreat, leaving us alone in the house, and I had decided to escape for a while and go take in a matinee—some mindless action flick to forget about my servitude, if only for a couple of hours. I tiptoed through the hallway, grabbed the doorknob, and just as I started to ease it open...

“And just where do you think you’re going?” bellowed my sister from the other end of the hallway..

I jumped back in surprise. “I’m just... going for a walk,” I lied, my voice cracking. "I need some fresh air. I'll be right back.”

Becky folded her arms across her chest. “No, you’ll stay right here. I need you to drive me to the mall today. Mom gave me the credit card before she left. I want to go shopping, and you're going to be my chauffeur."

I bowed my head and disconsolately came back in and sat down in the living room, my brief hope of escape gone.

“And how dare you try sneaking out without telling me,” she scolded, hands now on her hips. "Without asking permission." She shook her head in mock disappointment. "Just for that you’ll have to be punished.” She tapped a finger against her lips in mock contemplation. “Hmm... yes. I’ve got just the thing for you.”

I sat in dread as she disappeared into her bedroom. When she returned, she had a devilish grin on her face. She was holding a pair of her bright white tennis shoes, and, more ominously, a pair of white anklet socks with delicate lace frills around the tops.

“Here you go, brother Blondie,” she said, dropping them at my feet. “Take off those ugly shoes and socks of yours. You’ll be wearing these today.”

I stared at them like they were a live grenade. I was wearing shorts, and those girly socks and shoes would be on full display for anyone to see. The thought of going out in public like that was incomprehensible.

“Becky, please,” I begged. “I didn’t know you needed a ride, I swear. I would have asked if I'd known. I'll ask next time, I promise. Just... don’t make me wear those. People will see.”

“Oh, I’m counting on it,” she replied. "I'm absolutely counting on it. And I do have a darling little floral skirt that would complete the look perfectly. Pale pink with little daisies. Would you like me to go get it, or are you going to put those on without giving me any more lip? Your choice, Blondie. But choose quickly."

"No!" I yelped, horrified at the image she painted. "I’ll wear them!”

"Good boy," she said with a smirk, patting my head like I was a trained dog.

Resigned to my fate, I slowly removed my shoes and socks and pulled on the frilly anklets. The lace tickled my skin and made me feel instantly self-conscious, acutely aware of how ridiculous I must look. The tennis shoes fit perfectly. Of course they did. I sat stiffly, staring at the floor, trying to pretend the white ruffles hugging my ankles didn't exist.

“Stand up, Blondie,” Becky ordered, her voice bubbling with delight. "Let's have a look. I want to see the full effect."

She took my hand and led me to the center of the living room. "Hmm," she said as she circled me, scrutinizing my footwear. "You look adorable, absolutely precious. But we need to do something about those shorts. Those cargo things are completely wrong for the look I'm going for. I'll be right back," she said as she headed back to her bedroom.

Wait, what's wrong with these shorts? They're fine.

I waited anxiously, wondering what Becky had in mind. Surely she didn't expect me to wear a skirt out in public. She reappeared moments later, holding... oh no. Not a skirt, thank God, but it was probably the next worst thing—a pair of short, white denim shorts, clearly designed for a female. The frayed inseam was probably no more than a couple of inches. To compare, the cargo shorts I was wearing went past my knees, whereas these wouldn't even come close to mid-thigh.

"Put these on," she commanded, thrusting them toward me. "I'd like you to show off those pretty legs of yours."

"Oh God, please, Becky,” I pleaded, my voice cracking again. “I can’t go out like this!”

“Ohhhkay,” she said, turning back toward her room with a shrug. “If you’re going to be difficult, we’ll just go with the floral skirt. The pink one with the daisies. I think it would suit your coloring, actually."

"No! Wait!" I blurted out. "Okay, I'll do it! I'll wear the shorts!"

Becky stopped and turned around with a grin on her face. I'm sure she had a pretty good idea it would go that way. I took the shorts from her, my cheeks burning.

“I’ll go change,” I muttered, shuffling toward the hall.

“That won't be necessary,” she said cheerfully. “Right here is fine. No need to be shy. I mean, it’s not like I've never seen you naked.”

Red-faced and defeated, I turned my back to her and stepped out of my cargo shorts. I slipped into the short shorts she’d given me, while listening to her giggling behind me. They were tight, and indeed waaaay too short. I tugged on the hems in a desperate effort to cover more skin, but it was fruitless. My long, slender legs would be fully exposed, all the way down to the fucking anklets.

Becky clapped her hands with delight. “Oh, this is just precious!” she teased as she did a slow three-sixty around me while staring at my legs and feet. “But that shirt’s ruining the whole look. Tuck it in—or should I go grab one of my cute little crop tops instead? The pink one with the sequins, maybe? You'd look adorable."

I glanced down at myself. My blue tee was hanging almost to the hem of the shorts, and the last thing I needed was to add a crop top to this humiliating ensemble. Without a word, I quickly tucked it in. Then I stood stiffly, blushing furiously, eyes fixed straight ahead. Becky stepped forward and knelt to adjust the ruffles on my socks.

“Come, you must have a look at this.” She took my hand and led me to her room, where she positioned me in front of her full-length mirror. “Go on,” she said, “take a good look at yourself.”

I did. And I wished I hadn’t. Staring back at me was a tall, slim, red-faced sixteen-year-old boy wearing short shorts, lacy socks and girl’s tennis shoes. It felt like my legs were practically glowing with embarrassment. My face was definitely glowing.

Becky gave my elbow a soft squeeze and kissed my cheek with mock affection. “Don’t you look just darling, brother Blondie?”

Without answering, I turned away from the mirror, my face burning like I'd been standing too close to a fire. If Becky’s goal was to give me a girlish look, she’d certainly succeeded. Accentuated by the frilly anklets, my long, slim legs took on an unmistakably feminine appearance. Sure, I had grown some hair, but it was so fine, sparse, and light in color that it might as well not have been there at all.

As if she had read my mind, Becky glanced down at my legs and smiled. “I was thinking we might need to shave your legs before we went out,” she said, pausing just long enough for effect, “but they’re already looking pretty girly. Smooth as a baby's bottom, practically.”

With that, Becky skipped toward the door. I opened my mouth to protest, but then the image of her skipping back with a skirt in hand silenced me instantly. Submissively, I followed her out.

Once outside, I glanced around nervously. The suburban street looked empty for the moment, but it felt like a stadium full of spectators was watching me parade around in short shorts, lacy socks, and pristine white tennis shoes. Though the shoes and socks weighed only a few ounces, it felt like I was dragging a pair of balls and chains, every step being a reminder of my shame. And the breeze blowing on my bare thighs helped remind me of the short shorts—not that I needed a reminder!

I jogged stiffly to the car, while Becky strolled behind me at a leisurely pace, a smug grin plastered across her face. I hovered near the driver's side door, glancing around nervously for any passersby. The door was locked. Of course it was. I tugged at the handle again, doing a nervous little dance from foot to foot while she fumbled with her keys, taking her sweet time. Finally, after what felt like an eternity, Becky unlocked the car before casually tossing me the keys.

I scrambled inside, grateful for the small sanctuary the car provided. For a brief moment, I felt shielded from the world, and from my embarrassing attire. I took a deep breath, started the engine, and slowly backed out of the driveway, with a sinking feeling in my stomach as I braced for whatever fresh humiliation Becky had in store for me next.


Brenda's House

“Take a left at the stop sign,” Becky chirped from the passenger seat. “We have to go pick up Brenda.”

She watched me as my shoulders slumped. Of course Brenda was involved. My humiliation had barely begun, and already the other half of my nightmare duo was about to join in. Becky and Brenda had grown way too close lately. They certainly had something in common, that being their unbridled enjoyment of my humiliation.

“I didn’t tell her what you’re wearing,” Becky added. “I thought we’d surprise her.”

I didn’t respond. I just gripped the steering wheel tighter. Becky reached over and pinched my cheek like I was five years old, jiggling it gently with a little squeal. “We’re going to have so much fun today, Blondie! Just think—you, me, Brenda, and a whole mall full of people who've never seen your legs before. It's going to be magical."

I continued driving, looking straight ahead, longing for the day to end.

“Slow down, this is it,” Becky announced, pointing to a wide brick driveway of a huge, two-story home. “You can just pull in here.” I stopped the car, expecting Becky to get out. But no. “Why don’t you go ring the doorbell?” she said with a grin. “Brenda’s expecting us.”

I looked at my sister pleadingly, but she just pointed at the house. Reluctantly, I opened the door and stepped out, suddenly hyperaware of every inch of my legs exposed to the sunlight. I scurried up to the door and rang the bell, fidgeting as I waited, looking furtively side to side for any neighbors, any witnesses.

The door opened. It wasn't Brenda. It was her mother. I stiffened while she blinked at me, her eyes lingering on my legs with obvious curiosity, then dipping further to the socks and shoes with a kind of fascinated disbelief. Her brows rose in amused surprise.

“Uh, is Brenda here?” I squeaked, my voice about two octaves higher than normal.

“Yes, would you like to come in?” she asked, clearly trying not to smile. Her gaze once again dropped to my feet, as if she couldn't quite believe what she was seeing.

“N-no thanks. Just... just let her know we’re here to pick her up.” My face was flushing, and I was fidgeting nervously, shifting my weight from foot to foot.

She turned slightly and called inside, “Brenda, there’s a young...” She turned back to look at my face, then back at the lace. “...a young man here to see you.”

Moments later, Brenda bounded to the door. Her eyes lit up the second she saw me.

“Hi Blondie!” she chirped. Her eyes went straight to my legs. “Oh my gosh, what darling little socks! And they set off your pretty legs so nicely.” Her smile widened as she scanned me from head to toe, taking in every humiliating detail. "And such cute little shorts! Let me guess—Becky helped you get dressed today?"

I glanced at Brenda's mother, who was now also smiling with the tips of her fingers covering her mouth, her shoulders shaking with silent laughter. I had to get out of there, so without answering I turned and started running back to the car.

“He’s such a shy one, that Blondie,” I heard Brenda say, followed by a burst of shared laughter between mother and daughter.

I collapsed into the driver’s seat. Becky gave my thigh a cheerful little pat as Brenda approached the car.

“Oh, Blondie,” she said softly, “I'm really looking forward to taking you shopping. We're going to find you the cutest accessories. Maybe some hair ribbons? A little purse?" She straightened up, clapping her hands together. "This is going to be the best day ever!"

As humiliating as the morning had been, there was no rationale for me to believe things would get any better. With Brenda now in tow, I could only brace myself as we pulled away toward the mall—and whatever fresh humiliation waited there.
Last edited by Blondie on Wed Sep 02, 2026 9:29 pm, edited 8 times in total.
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Re: Roosevelt Humiliations

Post by TeenFan »

Going shopping at the mall. I can see the girls wanting to check out the latest fashions in the Lingerie Department.
Or perhaps check out the swimsuits at the sporting goods section.
Blondie in a girl's tennis outfit, just to match the shoes, would work well...followed by wearing the outfit to the Food Court for lunch.
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Re: Roosevelt Humiliations

Post by Blondie »

TeenFan wrote: Tue Jan 16, 2024 6:28 pm Going shopping at the mall. I can see the girls wanting to check out the latest fashions in the Lingerie Department.
Or perhaps check out the swimsuits at the sporting goods section.
Blondie in a girl's tennis outfit, just to match the shoes, would work well...followed by wearing the outfit to the Food Court for lunch.
As you will see when I get a chance to edit and post, you are on the right track!
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