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Roosevelt Humiliations, Chapter 7

Posted: Fri Jan 12, 2024 2:54 am
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, and she was the one who left my underwear on my desk after 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—her gaze practically peeling away my clothes—before flashing me a knowing grin. Without fail, my face would turn bright red, much to her delight.

After suffering a few of those embarrassing encounters with Brenda, I decided to exact some revenge. The payback was sweet while it lasted, but I’m sorry to say that ultimately, I paid the price—dearly—for this decision.

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 the homeroom. Seizing the opportunity, I strode up to the chalkboard and, in large capital letters, wrote:

BRENDA HOLLISTER HAS TINY LITTLE TITTIES.

Smirking to myself, I dusted my hands off, admiring my handiwork. Oh, this was going to be good.

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 a knowing grin. Satisfied with the inevitable rush of color to my cheeks, she let out a soft giggle, turned on her heel, 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. 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 crept up her cheeks.

Without hesitation, she shot out of her chair and stormed toward the board, erasing the incriminating 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. Judging by the way she immediately folded her arms over her chest, she knew exactly where everyone’s eyes were.

I leaned back in my chair, savoring the moment.

A few 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, but for the first time, I felt something close to vindication.


A Reversal of Fortune

That would have been a great way to finish off the year, but to my utter regret, I made the mistake of getting greedy. I wanted to relive that experience, so on the next day, I again arrived early to school. I had just written the words “BRENDA HOLLISTER HAS” on the board 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 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 anxiously.

Brenda was undeterred. “I don’t think you want me to get Mitch and Reggie involved here, now Blondie, do you?”

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

No, I know better.

I unbuckled my belt and unbuttoned and lowered my trousers 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.

I watched apprehensively as she took a pair of scissors 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 used the scissors to cut my underpants off and let them fall to the floor, where I felt them graze my feet.

While I instinctively covered my crotch with my hands Brenda, smiling with enjoyment, picked up my severed underpants and walked back to my seat, where she laid them on the desk.

Once again, thanks to Brenda, there was the ludicrous sight of a pair of underpants on my desk.

I looked around nervously as Brenda came back to me, the length of yarn in her hand.

“Hands on your head,” she commanded.

Resignedly I raised my hands to my head, exposing myself to my tormentor.

“Well, well, little boy, I see you’re still bald as a cucumber,” she teased. “And look how tiny you are! Such a cute wittle boy,” she taunted while taking my penis between her thumb and index finger and tweaking it back and forth.

Startled, I flinched and retracted my hips involuntarily.

Brenda giggled 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, which was a condition that caused me considerable angst. And having my small, hairless penis on display at this girl’s whim caused me extreme embarrassment.

My embarrassment and apprehension increased as Brenda took the yarn and 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.

Red-faced, I hastily donned 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, feeling around for the yarn as I flinched at the intrusion. Finding her prize, she slowly threaded it through before buttoning my fly back up at an almost agonizing pace, 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, Blondie,” she said as she pulled on the length of yarn dangling from my fly and walked toward the door.

“Oh God, no, Brenda, please!” I implored, my face already burning.

But she just laughed and started 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. My face felt like it was on fire as I followed Brenda like an obedient puppy.


Courtyard Humiliation

She then 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 when their mundane morning suddenly became 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, Brenda, what have we here?” asked Joanna, with relish in her voice.

“Oh, I’m just teaching Blondie here a little lesson,” answered Brenda. “Can you believe this little shit was the one who wrote on the blackboard about my tits?”

Brenda’s three friends laughed as she jerked on the yarn, forcing me to awkwardly jump forward a couple of steps.

Marcia, giggling freely, took the yarn from Brenda’s hand and merrily started trotting around the courtyard. 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 next to her friends and draped her end of the yarn over the outstretched arm of the Roosevelt statue. She then pulled on the end of the yarn, drawing me forward and upward, to a point where I was forced to stand on my tiptoes when I felt the upward tug on my genitals. Marcia held me in that position while the girls chatted among themselves.

The girls continued their laughter-filled conversation, chatting as if I weren’t even there, 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,” answered Brenda, “I managed to involve both his balls and his little dick. Would you like to see for yourselves?”

Brenda moved in my direction. My eyes widened in shock at this latest turn of events.

“Oh yes, let’s see!” Of course, all three of them were in full agreement.

“No!” I yelped.

Brenda, smiling, pulled my tee shirt from my jeans. She lifted it all the way up my chest and pulled it off my head. With two hands she tugged it downwards behind my back and scrunched it up at the small of my back, just above my tied wrists. I shivered involuntarily at the exposure.

“Excellent, my little hairless one,” she smiled while rubbing the palm of her hand back and forth across my bare chest.

She lowered her hand and began unbuckling my belt. She talked to me as she went about her task.

“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.

“No, Brenda! No! Please!” I begged frantically. I looked around the courtyard, and everyone was looking at the two of us in fascination.

She ignored me and addressed the girls while she slowly, deliberately went about her task of unbuttoning the four buttons.

“This will be pretty easy, because he’s not wearing any underpants,” she announced to the crowd while undoing the first button.

Gleeful shouts rang out. The grins broadened.

Brenda could sense that she had everyone’s attention, and she spoke a little louder. “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.

The second button was undone. She was playing the crowd, much to my wretchedness.

“Can you believe his impertinence?”

The third button was undone. My breathing quickened.

“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.

She unbuttoned the final button. I clenched my eyes shut, bracing myself for the next humiliation.

Brenda held onto the top of my trousers, holding the fly closed. Of course, this would be a temporary situation.

She looked up at me, grinning sadistically. “Are you ready, big boy?” she teased.

“Please…Brenda, I’m begging you…don’t do it!” I pleaded anxiously.

“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.

“Prepare yourself, my little hairless one,” she taunted, tickling my ear in the process. “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.

My anxiety was mounting, and I swear I could hear my heart pounding on 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.

“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! No! Please!”

“Oh, yes, Blondie boy. This is going to be a moment you’ll remember for the rest of your life.” She paused. “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 now, as it sunk in that she was absolutely right in that assessment.

She took notice of my horrified look. “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. 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.

"When I take these down, it should be quite comical, because you’ll be squirming around in absolute embarrassment, 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—"

“Here we go, folks,” she announced, her voice ringing with mischievous delight. “Is everybody ready?”

A loud, enthusiastic cheer erupted from the gathered students, their excitement palpable.

Brenda stepped back slightly. 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.

The roar of laughter in the courtyard was riotous.

I writhed and twisted my body frantically, but there was nowhere to hide.

“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.

“And he has no hair!” squealed another.

“Oh, this is too much!”

Mortified to the max, I tried lifting each leg up one at a time in a frenzied attempt at covering up, 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 went off, and the crowd began to disperse.

Marcia let go of the yarn, and Brenda buttoned and buckled me up, making sure the yarn stuck out from my fly.

I was relieved that she didn’t make good on her threat to take my pants completely off. But, to my dismay, she chose to leave my upper body exposed.

“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.

“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 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.

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 untied my hands. “Alright, 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 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, I walked to the chalkboard, 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. 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, were my shredded underpants. With practiced shame, I snatched them up and stuffed them away, 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.

Roosevelt Humiliations, Chapter 8

Posted: Fri Jan 12, 2024 5:17 pm
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 made me write on the board:

“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 on her face. And when she turned and looked at me, I swear she looked at 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 do. "I am, ma’am," I admitted, my voice barely above a whisper.

I cringed, dreading Miss Farnsworth’s reaction. I had already found out firsthand during my freshman year that she has a sadistic side to her.

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.

As I recall, the grin on her face when she looked me up and down suggested that she was deriving more than a little pleasure from the experience.

Plus, I subsequently learned that she has the reputation of being quite creative in her manner of dishing out punishments to her students, all of which involved a certain amount of imposed humiliation and usually had to do with clothing.

Take, for instance, what had happened to a girl in her third-period English class. After disrupting the lesson one too many times, she found herself on the receiving end of one of Miss Farnsworth’s embarrassing consequences.

Miss Farnsworth took her behind a partition and dressed her in a baby blue, little girl’s party dress, complete with a petticoat. It had puffy sleeves and was very short. She added frilly anklets, shiny black shoes, and a large bow in her hair that matched the dress. She was forced to wear the ridiculous outfit for the remainder of her classes.

I remember seeing her in the cafeteria during lunch that day. Her face was as red as could be, and she looked as if she just wanted to just crawl away and die.

But I digress. Now, it was about me, and I had an awful feeling that I was about to become the next victim of her 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. "In the future, it would be wise not to advertise your shortcomings."

The room exploded. Laughter boomed from all sides, and my face turned tomato red.


The Bra

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

"Mr. Haggerty, are you familiar with the concept of shame clothing?" she asked, her tone almost conversational.

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 to form a response.

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—a delicate, lacy black bra.

The room erupted. The laughter, the hoots, the absolute glee of my classmates echoed off the walls. Miss Farnsworth held the bra at arm’s length, admiring it as if she had just discovered a rare gem.

“Oh yes,” she murmured, her eyes twinkling as she took in my mortified expression. “I’m quite confident this will do just fine.”

I barely heard the continued cheers and cackles from behind me—I was too busy wishing for the ground to open up and swallow me whole.

Then came the inevitable words.

“Would you please remove your shirt and come up here, Mr. Haggerty?”

My stomach plummeted.

Defying her would only make things worse—much worse. I swallowed hard, feeling the heat radiate from my face, and hesitantly pulled my shirt over my head. The moment it was off, the giggles doubled. I didn’t dare turn around—I knew Brenda was probably on the verge of tears from laughing so hard.

I trudged to the front of the room, my arms hugging my shirt to my bare chest like it was a security blanket. 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 tilting her head. “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.

“Hold your arms out to the sides, please.”

I hesitated. But refusing wasn’t an option. Slowly—so painfully slowly—I lifted my arms.

She stepped behind me and reached around my chest, holding the bra’s unfastened cups in place. She continued teasing me as she went about her task of fastening the cups together.

She was standing very close to me, and her mouth was close to my ear as she looked over my shoulder. 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.

With excruciating precision, she clasped the front of the bra together, giving the lace a little adjusting tug for good measure. “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 and was immediately sorry I did so. She was wiping actual tears from her eyes. 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, she gave the cups one final adjustment, stepped back, and admired her work.

"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. That look alone sent a shiver down my spine. This was not going to end well for me.

And sure enough, my worst fears were about to be realized.

“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 pants, and you were showing off some very pretty legs.”

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.

“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.

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.

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

She sighed, shaking her head. “Now, now, young man, let’s not be difficult. You’ll do as you’re told and pull your trousers down.” Then, her lips curled into a knowing smirk. “Unless, of course, you’d rather I call in Mr. Jennings and have him review the lovely message you left on the board?”

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. Worse still, if he got involved, there was a very real chance my parents would hear about this.

No. Absolutely not.

But still....I had to at least try to reason with her.

I spoke the next sentence very softly, so only she could hear me. "I'm not wearing any underpants."

The moment the words left my mouth I felt my face burn hotter than ever and glow even more when I saw the grin on 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 whetted her appetite for more humiliation.

With deliberate slowness, 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.

The reaction was instantaneous. Laughter exploded behind me, a mix of giggles, gasps, and outright guffaws.

As much as I wanted to tell the truth—that Brenda had cut them off me and that she made me write about my penis on the board—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 about your penis is really true. I must admit, I am skeptical about the hairlessness, considering your age. As for the size, 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 mischief. “Now then, let’s get those jeans down and have a look.”

Have a look?

A fresh wave of panic gripped me. I felt like I was trapped in a surreal nightmare. My hands hovered over my belt, but my body refused to obey. 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 dramatically. “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."

I released her immediately, dropping my hands uselessly to my sides.

That was all the opening she needed. In one swift motion, Miss Farnsworth undid my belt, unfastened my jeans, and yanked them straight down to my ankles.

The classroom erupted. The laughter was deafening, a symphony of hysterics and delighted shrieks. And amidst the cacophony, I somehow make out Brenda’s voice— seemingly louder than the rest, laughing so hard she was probably in tears.

My hands flew to my crotch, shielding myself desperately. But the moment my fingers brushed against something trailing down my leg, my heart stopped.

The bright orange yarn.

It was dangling to the floor

I had completely forgotten about it.

Miss Farnsworth’s curiosity was clearly piqued. With an amused smirk, she reached down and took hold of the yarn, lifting it slightly between her fingers as if inspecting a peculiar specimen.

"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.

“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….now 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.

Miss Farnsworth, clearly enjoying herself, took her time appraising the situation with an ever-widening grin. “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.”

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?

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. "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.


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….hmm, perhaps I can help.” She tapped a finger against her chin. “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.”

Her smile widened. “Very good! Then you must remember Maria singing I Feel Pretty. Would you be so kind as to sing it for us, Mr. Haggerty?”

I shook my head back and forth. “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.”

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. Miss Farnsworth, completely unfazed, turned back to me with a satisfied grin.

“There we go! Now, your turn, Mr. Haggerty.”

“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 with a flourish.

She actually planned for this.

She handed me the sheet, which I accepted with trembling fingers. “Now, face the class and sing for us. Let everyone hear how pretty you feel.…and if you do a really nice job, I’ll let you put your shirt on and pull your pants up before you go to your next class.”

Singing was bad enough. Turning around and facing my classmates? Unthinkable.

“B-but Miss Farnsworth,” I begged, my voice cracking. “I’ll sing, just….please, can I face this way?”

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.

Thirty pairs of eyes locked onto me. More specifically, below 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. 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.

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 managed to sing, though I was barely audible.

♬ “I feel pretty…” ♬

“Hold it!” Miss Farnsworth interrupted. “Keep the sheet music off to the side so we can see your face.”

I lowered the sheet slightly, my cheeks burning hotter than ever.

Miss Farnsworth chuckled. “Oh my, you really are blushing now. Class, have you ever seen a face glow quite like that?” The giggles intensified. “I do believe the shame clothing is working. Do you feel shamed, Mr. Haggerty?”

I gave a small, miserable nod.

“Excellent! Now, from the top.” She motioned for me to continue.

♬ “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.

♬ “And I pity….any girl who isn’t me tonight….I feel charming….oh so charming…” ♬

Mercifully, the bell rang, signaling the end of homeroom.

Miss Farnsworth started clapping as she strode to the front of the room. The class followed her lead, applauding my performance with glee. Thoroughly shamed, I turned away and bowed my head as my classmates, still laughing, gathered their books and began filing out.

Miss Farnsworth retrieved the sheet music from my hands. “That was well done, Mr. Haggerty.” She picked up my t-shirt 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. I reached back 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 in horror.

She smiled sweetly. “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. 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, thoroughly entertained. “Brenda, would you be so kind as to keep an eye on Mr. Haggerty today? His black bra should be quite noticeable under his white tee. If at any point he removes it, do let me know. I have a pair of panties for him to wear tomorrow for us if he disobeys me. I probably can't send him to classes with his little penis on display, but I can certainly send him off in a bra with matching panties.”

Brenda’s grin widened. “Oh, I’d be delighted, Miss Farnsworth. I hope he takes it off.” She looked at me and grinned. “I think Blondie would look adorable in a pair of panties.”

Miss Farnsworth chuckled. “Indeed."

They both watched as I donned my tee shirt over the bra. I looked down at my chest. Miss Farnsworth was right; to my utter chagrin, the bra stood out prominently

"Now, off you go, Mr. Haggerty. And tuck your shirt in. I want you to feel pretty all day long.”

As I hurried out, face burning, I could still hear the demented lady cackling to herself.

Roosevelt Humiliations, Chapter 9

Posted: Sat Jan 13, 2024 6:57 pm
by Blondie
Image

Chapter 9: Stripped on the Soccer Field

A Lunch Date with Brenda

I walked through the hallway as quickly as I could, somehow hoping I could 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 sighed. 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 smoothly. “I’ll be with some friends on the north end of the soccer field at, let’s say, 12:15. 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. “Did I mention Mitch is my cousin? He absolutely adores me. He’d do anything I ask.”

With that, she gave me a gentle—but unmistakable—squeeze on my ass before veering off in another direction, leaving me standing there, dreading whatever she had planned.

“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 go into detail about the harassment I dealt with 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.

Brenda? She was not predictable.

And that terrified me more than anything.

By 12:15, I found myself making the dreaded trek to the soccer field, every step heavier than the last.

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 as she pointed in my direction, mouthing the words “There he is.” The others turned, their faces lighting up with grins of pure anticipation.

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

I barely had time to respond before Joanna, smirking, tilted her head at my shirt. “Didn’t your mother teach you to wear a white bra under a white shirt?”

Undoubtedly, Brenda had apprised them of my harrowing experience in homeroom.

Brenda wasted no time carrying out her torment. She sidled up next to me and, without hesitation, reached for the middle buttons on my fly.

My body tensed. “Brenda—”

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, completely unbothered. Then, in a voice that left no room for argument, she said, “Put your hands on your head and keep them there until I say otherwise. Unless you want me to get Mitch involved.”

I hesitated, and then, with a sinking feeling, I slowly raised my hands and placed them on my head.

Brenda, satisfied, slipped her hand back into my jeans. Her fingers brushed against my balls, causing me to flinch.

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

She retrieved the end of the yarn, and with a triumphant tug, she pulled it through the opening of my fly and started leading me down the soccer field.

Her friends giggled as they walked alongside us, delighting in my submission. I could do nothing but follow, hands locked behind my head, humiliation radiating from every pore.

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

At that point Brenda decided to take it to the next level.

Grinning wickedly, she reached down, unbuckled my belt, and undid the remaining two buttons of my jeans.

I froze.

For now, my pants remained 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.

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

I hesitated, but the expectant looks from Brenda left me with no real choice. Slowly, I raised my hands.

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.

A cool breeze swept over my skin, but the real shiver that ran through me came from the intense humiliation.

The four girls erupted into delighted whoops, eyes glued to my now fully exposed lacy black bra. My blushing face only encouraged them.


Pants Come Down

“Okay, pretty boy, you can put your hands back on your head,” Brenda giggled. “And just so you know, if you dare move them, your pants are coming off completely—never to be seen again.”

I swallowed hard and obeyed.

Then, with that wicked glint in her eye, Brenda turned and started leading me back across the field. She walked backward, keeping a close eye on my pants, 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, all watching, whispering, laughing.

At first, my pants mercifully stayed in place.

But then Brenda picked up the pace.

And I felt it.

The waistband loosened. The denim slipped ever so slightly.

“They’re starting to come down!” Cheryl squealed gleefully.

I clenched my jaw, desperately trying to keep them up without breaking Brenda’s rule. I stretched my legs out as much as I could, 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 pants dropped to my knees.

Another two steps, and...

They collected at my ankles.

The outcry from the girls in front of me and from the rest of the onlookers remains embedded in my memory to this day. Laughter. Cheers. Shouts of delight. What a sight I must have been, naked from the ankles up but for a black bra, awkwardly trying to keep pace with Brenda.

“Look at his little weenie!” laughed Joanna.

“And ‘little’ is the operative word,” countered Marcia gleefully.

“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 zigzagging me across the field, 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 done.

With a flourish, she led me straight to the goalpost, where she tied the end of the yarn securely to the net.

Then, kneeling down, she grabbed my ankle.

“Hold your leg up,” she instructed.

I hesitated. “Please, Br—”

“LEG UP!” she barked while giving my naked butt a hard swat with her bare hand.

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 but complied, and within seconds, she had me standing in nothing but a black bra.

A fresh wave of mortification crashed over me.

Brenda dusted her hands off and stood. “You’ll find your clothes in the other goal,” she informed me sweetly. “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. “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 girls sauntered off, still laughing.

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.

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

The crowd wasn’t losing interest throughout my ordeal. If anything, their laughter seemed to increase 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 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 stood up 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, sitting on the bench with her friends, holding my pants high in the air.

“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 crotch, took in the sight with wicked delight while I stood there, trembling.

I swallowed. “Please, Brenda….may I have my pants?” I asked miserably.

All four of the girls were giggling freely.

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

“Y-you own me, Brenda, and I promise to obey you, no matter what.”

“Good boy. Now say, ‘I’m so embarrassed. I’m a boy wearing a bra, I have no hair on my body, and my teensy little wee-wee looks like a little clitty.’ ”

Amid the uproarious laughter, I repeated the humiliating words.

“I’m s-so embarrassed. I’m a boy wearing a bra....I have no hair on my body.…and my.…teeny.…little wee-wee looks like a little.…a little c-clitty.”

That was extremely difficult. But I wasn’t done.

“No, no,” scolded Brenda, while smiling deviously. “You said, ‘teeny,’ and I told you to say ‘teensy.’ Now try it again. Only this time, say, ‘I’m sooooo embarrassed—and make sure you say it like that—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 deafening, a relentless chorus of amusement at my expense. I had to get through the latest humiliation and get the hell away from the sinister Brenda.

“I’m soooo embarrassed,” I forced out, my voice barely above a whimper. “I look like a little girl… I’m wearing a bra….I have….I have no hair on my body....I’m….my t-teensy weensy.…wittle w-wee wee looks like.…an itty b-bitty.…an itty bitty clitty.”

As the words left my mouth, a fresh wave of giggles and mockery erupted around me. My face burned—hotter, redder—more intensely than ever before.

“Excellent!” exclaimed the laughing Brenda while clapping her hands for me. “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.”

My stomach dropped. “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.

Miss Farnsworth. A matching bra and panty set.

I caved.

Voice trembling, I forced out the words.

♬ “I feel pretty… oh so pretty… I feel pretty and witty and gay…” ♬

My voice cracked. “P-please… I can’t remember any more…”

Brenda and the girls were laughing so hard they couldn't speak.

With a final chuckle, 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 survived my last two classes, finally returned the bra to Miss Farnsworth, and slinked out, determined to put the whole nightmare behind me.

* * * * * *

As I stepped through the doors on the final day of my sophomore year at Roosevelt High, I took one last glance over my shoulder at the school building and shuddered.

It was clear that new bounds had been set for the extent of my humiliation.

I’m here to tell you, I had never been so relieved for summer vacation to begin.

Roosevelt Humiliations, Chapter 10

Posted: Sun Jan 14, 2024 6:38 am
by Blondie
Image

Chapter 10: Forced Naked at a Public Beach

Starting Puberty

I had completed my third year at Roosevelt High. If there was one silver lining, 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 was still well behind what it should have been, 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.

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 in the courtyard when I spotted Brenda and Joanna lingering near the Roosevelt statue. Our eyes met, and with a smirk, Brenda curled her index finger, motioning for me to come over.

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.

"Hi, Blondie," Brenda greeted me with a honeyed smile. "It’s good to see you. We’ve missed you these last three months."

"What do you want?" I asked defiantly.

"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. But this time, I wasn’t having it.

"Fuck off," I snapped. "I’m not your plaything anymore." 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.

"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.

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.

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. He was already waiting, and as soon as I slid into the passenger seat, we sped off. 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 my account 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. That meant we shared a homeroom, where—lucky me—she sat directly behind me.

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, and I had a friend over. Becky was taking a bath. 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, 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.

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 water every which way, her voice ringing through the house. And oh, did she let the profanities fly. She was swearing like a sailor.

It was quite dramatic.

Of course, she told my parents, 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 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. But what I didn’t know was that over the summer, Becky had forged an alliance with them.

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, I caught a glimpse of Becky, 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—my swim trunks were being yanked down!

They were already past my knees, and before I even had a chance to kick my legs, they were pulled off my feet.

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

“Oh shit! Oh shit!” I shrieked..

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. I doubled over, trying to cover myself by lifting one leg in a desperate, awkward attempt at modesty. But the damage was done.

The first faces I saw were grinning—no, beaming—with delight. Mitch. Becky. Brenda. Marcia. Joanna. Cheryl. They were all there to witness my humiliation.

I whipped my head around, searching for an escape, but there was nowhere to hide. 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.

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.

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.

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 bathrooms. I took them two at a time, desperate for refuge. My heart nearly burst with 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 it 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 my wrists 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. Or it’s just gonna get worse.”

“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.”

Mitch nodded. “Fine. Give Blondie his swimsuit, Becky,” he said as he 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 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. A tie bikini. I recognized it immediately as one of Becky’s.

“Here you go, Blondie,” she chortled. “This color should really bring out your eyes.”

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. “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 what, my humiliation would be extreme.

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.

I guess my decision was made. Resigned to my fate, I turned my back to them and reached for the bikini bottom. Grimacing, I slid it up my legs, cringing as the snug fabric settled around my hips.

I welcomed the coverage, though the femininely styled hipster would not have been my first choice.

I looked down at the top and turned around 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.”

She spun me around, sliding the straps over my arms. The spaghetti straps rested on my shoulders as she pulled the ties tight behind my back.

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

The room burst into laughter once more.

Becky spun 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. The spandex clung too well, outlining everything. I looked down in horror—so did everyone else.

“Oh, God,” I muttered.

There was more laughter 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. The faster I got it over with, the better.

I cracked open the door.

The beach was still packed.

I swallowed hard, then bolted.

“Don’t even think about taking your top off!” Mitch called after 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. The uproarious cackles. I even heard a couple of wolf whistles.

It’s hard to say which was worse, the swimsuit or the nudity. I wouldn’t wish either on anybody.

I didn’t dare look at anyone.

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. She was standing twenty feet away, twirling my keys around her finger.

“Looking for these?” she teased.

I lunged toward her.

She took off running.

For the next minute, I chased her across the beach, dodging sunbathers, while she shrieked with laughter. Finally, I tackled her to the sand, prying the keys from her grip.

“Help! I’m being attacked by a lesbian!” she howled.

The entire beach erupted in hysterics. 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 unlocked the door and collapsed 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.”

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.

I sped away, 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.”

She didn’t have to tell me twice. I sat up, staring straight ahead, my face flushing brightly.

But my ordeal wasn’t over.


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—no, we can make it home—”

“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 only make things worse. 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, my stomach twisting into knots.

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!”

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 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.

“Oh, she’s playing hard to get,” the brunette teased.

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

That was a mistake.

Becky, still grinning like the devil himself, 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 sweetly.

“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, African American 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, grabbing the first Diet Coke I saw. That part was easy. But the second part of Becky’s cruel and unusual punishment? Not so much.

“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, 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. 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, shaking her head in amusement as she handed me the change. Throughout the exchange, she never stopped laughing, and was so flabbergasted, she never said a word.

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.

Blushing crimson, I dashed past them. I mean, I couldn’t get to the car fast enough.

Thankfully, Becky let me in, and I threw the bag onto Becky’s lap before collapsing into the driver’s seat.

Becky was howling. She had tears in her eyes. “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. Every few moments, she’d look at me and smile.

I 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.

Re: Roosevelt Humiliations

Posted: Sun Jan 14, 2024 11:48 am
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.

Roosevelt Humiliations, Chapter 11

Posted: Sun Jan 14, 2024 7:50 pm
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, as always, had other plans.

“I’ll take my swimsuit back now, please,” she said sweetly, holding out her hand.

“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. 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 coastline. And now that I think of it….you never even thanked me.”

She looked at me expectantly. Did she really expect me to thank her?

I blinked. “Are you serious?”

She gave me a look. One that said: Try me.

“I’m waiting,” she sang.

“Thank you,” I muttered, defeated.

“For what?”

Ugh. “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?"

She didn’t answer. Instead, she leaned forward and laid on the horn. A long, loud BLAAAAAAT filled the garage.

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 casually, checking her nails. “Not sure about Mom, though. Her car’s here.”

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 “I hit the horn by accident!”

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

“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 audibly and glared at Becky, who was clearly on the verge of losing it. Her whole body was shaking from silent laughter.

“No, 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?

Then Becky rolled down her window.

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

“It was very interesting, Mom,” she said brightly. “Blondie was the star of the beach today.”

"Oh, really," answered our mom curiously.

“Oh yeah. Everyone got to know him really well. You should’ve seen him. I think he thought we were at a nude beach.”

"Whaaaat?" answered my mom, who was agape.

"Oh, shit!" I whispered. "Becky! Knock it off!"

“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!”

“Oh my God!” Mom gasped.

“I—I wasn’t trying to—” I stammered.

“Well," Becky said, ignoring me. "Brenda got even. She pulled his trunks right down in front of everyone.”

“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 sink into the floor.

“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, for heaven's sake," 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.

“Well, that was fun,” Becky said, wiping tears from her eyes. “God, your face was priceless.”

"Son of a bitch!" I said breathlessly. "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 eye, I started shimmying out of the bottoms. 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 officially reached the point where I own you. Like, completely. I snap my fingers, you jump. From now on I can make you get naked for me, anytime and anywhere—at my pleasure. It's honestly kinda beautiful."

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. Group chat’s blowing up—Brenda, Joanna, Marcia, Cheryl, and Mitch. They want an update.”

"Please, Beck. Let me get dressed."

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

She then held up her phone to me and took a picture.

"They wanted to see," she said with a grin.

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.

“I’ll just put these on your bed,” she said sweetly, opening her door.

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

"Well, she'll 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.

"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 sweetly and trotted up the stairs, my trunks in 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, building up the courage to go into the house. Finally, after one last big sigh, I opened the car door and crept out, bare feet on 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 did hear her in the kitchen, moving around, humming. That was my window.

Ahead of me was a long hallway that led to the living room and the stairway to my room. Halfway down the hallway was a standard-size 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, closed 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. Before I reached the kitchen, my mom stepped into the hallway, towel in one hand, nonchalant as anything.

That nonchalance quickly turned to surprise when she turned and saw her 16-year-old son, who had stopped suddenly with a deer-in-the-headlights look on his face. He was naked.

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

When I saw her, I stood momentarily frozen, not knowing which way to turn. I quickly covered my modesty with my hands—though I think my mother might have managed to attain a quick glimpse of my genitals, something she hadn't seen since I was a child. I could feel the heat rising up my neck.

Her voice cut through 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, she can be quite 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.”

I turned slowly, miserably, still shielding myself.

She crossed her arms and gave me a once-over. "You stay right where you are, and don't move," she said while pointing at me.

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

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

It all goes back to the time I intentionally walked in on Becky while she was in the bathtub. My mom was pretty upset with me, and even though I was grounded for the rest of that month—my dad had decided on the punishment—I don't think she felt that the penalty fit the crime. Being of the female persuasion, she had felt more empathy for Becky than my dad or I did.

Compound that with Becky's bogus story about how I tried to pull off Brenda's top 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 my mom, who was walking briskly in my direction. They both stopped a few feet in front of me.

“Oh my God, Mom! Why is Blondie naked?” she said, with an impish grin on her face.

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.

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 tub....well, let's just say that this is his moment of reckoning."

"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." They both were quiet for a moment as they continued to stare at me. "What shall we do with him?" asked my mother. "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. "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 was fully exposed." 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....even though he is naked....he saw a bit more of you than what you're seeing of him right now."

"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 like to take a gander at his goose!" remarked Becky.

"Oh, that's a good one, Becky!" laughed my mom. They both laughed lustily, while I stood there immersed in my wretchedness.

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 too far!”

“You didn’t think it was too far when you burst in on your sister’s bath time,” Mom said.

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

Becky gave me a look. “Please. You walked in gawking at me, and your eyes looked like they were gonna come out of their sockets.”

“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."

"Yes, but I never thought your punishment was harsh enough," said my mother. "Considering how shameful your action was, I think you deserve to be shamed. And Becky deserves to witness your shame, taking into account how you violated her." I glanced at Becky, whose smirk seemed to be permanently plastered on her face. "Now I'd like you to remove your hands from your privates and put them on your head," ordered my mother.

It looked like I was really going to have to go through with this. That being the case, I had to at least try to modify the conditions. The notion of exposing myself to my mother added considerably to my anxiety.

"Mom, please. Can I....if I have to do this....can you please go away so just....just Becky will see?"

"Hmm, I do understand," said my mom. "You are a little old to be displaying yourself to your mother like that. But that puts me in a bit of a quandary. The intention of this little punishment session is to shame and embarrass you, as you did to Becky."

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

She paused as she pondered my request. "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?

"Well, I agree with you, Mom, that after what he did to me, we need to embarrass him. To that end, he's sixteen years old, and I think having his mother see his bare privates would be very embarrassing for him. And I caught a glimpse of his little bits when Brenda pulled down his trunks, so I understand why he wouldn't want anyone to see what he's got down there—or what he doesn't have, to be more accurate,” she said with a giggle.

My mother's lips curled into a slight smirk. "So you think I should stick around to witness his shame."

"I do, Mom. One hundred percent. Also, Blondie had a friend with him, so there were two witnesses to my nakedness.

Oh shit, I think that swayed her.

"That's a very good point. Okay, a witness I shall be. Blondie, let's get those hands on your head."


Exposed and Teased

"Mom, please..." I begged, my voice barely a whisper.

"NOW!" Her authoritative voice echoed throughout the hallway, with that unmistakable do-not-test-me finality.

My hands shot to my head. I stayed hunched over, legs tightly crossed in one last act of desperation.

"Can you get him to stand up straight and spread his legs?" asked Becky sweetly. "We can't really see anything."

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

I winced like I’d just been sentenced to a firing squad. But slowly—and painfully—I obeyed. Back straight. Feet apart. Every nerve in my body screaming with humiliation as I stood there as my mother and sister unabashedly stared straight down at my genitals.

Both of them were smirking now with no shame. Just open, unfiltered amusement at my expense.

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

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

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 per orders. The humiliation was excruciating.

I expected Becky to be soaking up every ounce of my discomfort—of course she was—but it was disconcerting to see that my mother was clearly enjoying this little spectacle just as much.

It was all I could do to keep myself from turning around and running back into the garage. But I knew that defying my mother would only worsen my situation, and I had the sense that this would be over momentarily.

That sense was....incredibly naive.

Roosevelt Humiliations, Chapter 12

Posted: Mon Jan 15, 2024 6:26 pm
by Blondie
Image

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 sanctity of my room. But just when I figured that we were about finished, the sound of the doorbell gave me a start. My eyes widened while the three of us exchanged open-mouthed glances. There was a momentary silence while all three of us pondered the ramifications of someone being at the door while a naked 16-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 declared. "Shall I bring her back here?"

"No!" I shouted.

"Hmm," said my mother. "It might be good for Blondie to have another witness to his punishment—and someone from outside the family to boot, just like when you had your dreadful incident. Sure, have Brenda join us."

The giggling Becky practically skipped out of the room in her delight, leaving me alone, facing my mother. Naked. "Uncomfortable" doesn’t begin to explain how I felt at that moment.

I heard Becky whispering something to Brenda. 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.

"I know this is embarrassing for you, Blondie," said my mother, in what might have been the understatement of the decade. "But when you think about it, this really is Karma at its finest. After what you did to Brenda today, I think it was fate that brought her here right now."

Or more likely a text from your diabolical daughter.

Just then, the gruesome twosome entered the hallway. "Oh, my goodness! Why is Blondie naked?" asked the delighted Brenda. I could tell by Brenda's genuine, astonished reaction that Becky had purposely neglected to tell her friend of my state of undress.

"That's the question of the day," responded my mother. "Brenda, Becky told me what happened at the beach today. I want to express my sincere apologies to you for my son's behavior."

"Oh, it's okay, Mrs. Haggerty. It was embarrassing, but I'm over it now." Grinning, she pointed at me. "This more than makes up for it," she said. The three of them laughed, adding fuel to my persistent blush.

"Yes, that's why I wanted you to come see this," said my mom. "It's the least I could do to make you feel better."

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

"I'm glad to hear it," said my mom. I shifted my feet and fidgeted anxiously, as the humiliation was becoming unbearable. "Judging by how red his face is, I'd say his punishment is having the desired effect," continued my mom.

"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 small side," said my mom. "Becky and I were commenting on that earlier."

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

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

"I'd say both," answered Brenda. "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.

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. "I don't....please, I don't know. A while ago."

"There's not that much hair there," said Becky. "I don't think it's been that long."

"I can tell you for a fact that it hasn't," said Brenda. "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 had no hair on his....on his genitals. He also told me how little—he used the word 'tiny,' actually—he mentioned how tiny his penis was. 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 be so underdeveloped."

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

"So, Blondie," persisted my mother. "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 hard for you to be fifteen years old and prepubescent," she commented.

"Just like it must be hard for him to be sixteen years old and have such tiny little bits," followed Becky devilishly. Brenda and Becky broke out into convulsive laughter while my mom looked at them and smiled.

After the laughter died down, my mother said, "Okay, girls, I think we've succeeded in giving Blondie his comeuppance. Are you satisfied now?"

About freaking time! Let me out of here!

After thinking for a moment, Becky said, "Mom, um....there is one other thing I'd like to see you do to him...."

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

Our mom looked at her curiously. "What would that be, Becky?" she asked with her head tilted to the side.

"Well, do you remember whenever Blondie was a bad little boy, how you would punish him?"

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

"Yes," answered my mother. "I used to put him over my knees and give him a spanking."

"I would love to see that again," said Becky.

Becky looked at me and smiled impishly. I looked at Brenda, who was making eye contact with me, and had a lascivious grin on her face. I looked warily at my mother. My mother looked at me with a devilish grin of her own. I had a very bad feeling about this.

"We do still have that same armless chair in the living room that I used to use for his spankings," was my mother's response.

"Yes, we do!" said Becky. "You know, you always let Blondie keep his pants on when you gave him a spanking. I must confess—I always wanted you to do it on his bare bottom."

"Well, by golly," said my mother while looking at my midsection, "Then I think it's high time that we do just that."

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

"Mom! Wait, you can't be serious!" I said as I stood there agape, dropping my hands from my head. "I thought we were done here!"

"First of all," answered my mother, "I never told you to remove your hands from your head." She stopped and stared at me until I complied by slowly moving my hands back behind my head. "Second of all," she continued, "We are done with your punishment when I say we are done. What you did to Becky before, then today to Brenda deserves proper discipline. I'm glad Becky brought this up. Under the circumstances, a spanking on your bare bottom seems rather appropriate. After I'm done with you, I suspect you will be cured of your naughty behavior."

I stood there miserably, incredulous of what apparently was about to transpire.

"I never told you this, Becky, but one of the times I put him over my knees I actually did spank him on his bare bottom, said my mother." She looked at me and said, "I'm sure Blondie remembers it well." I didn't answer, but of course I remembered it well. It's not something one would ever forget.

"I'm so sorry I missed that!" said Becky.

"Yes, you were already asleep, or I would have let you watch. I only gave him a spanking a handful of times, and he was usually wearing a pair of pants. But one time it was at night, and he was wearing his pajamas, without any underwear. I think he was 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.

"Absolutely. 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 pulled his pajama bottoms down."

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

"I should have," laughed my mom. "Anyway, I still remember to this day how he was taken by surprise when I pulled down his pajamas bottoms. He let out this high-pitched little squeal."

"Oh, I love it!" exclaimed Becky.

"Delectable," chimed in Brenda.

"I have to admit, it was much more satisfying for me to spank his bare bottom instead of having the material in the way. The slaps had this nice, rich sound to them. I'm sure he felt it a little more than usual, too. That was nice, but I guarantee you that the embarrassment of having his mother baring his bottom had more impact than any pain he felt. So the punishment had the desired effect."

"Was he crying?" asked Becky.

"Not out loud. But when I let him up, he quickly pulled up his pajamas—that was his number one priority—and I had him turn and face me to apologize. He did have tears running down his face. And his face was just as red as it is right now.

"Anyway, he certainly learned his lesson, because that was the last time I had to spank him."

"Until now," corrected Becky.

"Until now," concurred our mother.


The Spanking

She turned and addressed me, pointing toward the living room. "You know where the chair is," said my mother. "I'd like you to lead the way and go stand next to the chair and await your punishment."

Oh my God, this is really going to happen!

My mother stepped aside to one side of the hallway, while Becky and Brenda did the same right across from her, clearing a path for me. With my hands still behind my head, I made the excruciating naked walk of shame. The girls were giggling freely as I passed by them, and as the three of them followed me into the living room.

I stopped next to the infamous chair and waited as my mother took her seat. She used both hands to smooth out her long, cotton skirt. She was ready. "Assume the position, please," she directed while gesturing to her lap.

There was a tantalizing, almost palpable feeling of anticipation in the air. For Becky, Brenda, and even my mother, one could probably describe it as delicious anticipation, whereas my anticipation was filled with profound apprehension.

Under the watchful eyes of the three females, I laid myself out over my mother's lap. Even though it had been many years, it was an all too familiar, ignominious position—though this was exponentially more humiliating than in the past.

I felt her use both hands to adjust my torso to her liking. A few seconds went by as I lay there in total silence. My heart was beating at an accelerated rate, and I suspect the same could be said for the other occupants of the room.

Without a word, my mother began. I heard the first slap reverberate throughout the room before I felt the stinging pain register. She continued with a slow but steady volley, alternating from one side to the other.

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

"Oh, I think we can warm him up more than this," remarked my mother as she continued her onslaught.

"Yes, it's definitely getting redder," noted Brenda. "Oh, this is so much fun!"

The "fun" continued for a few more seconds before my mother stopped. I felt a slight sense of relief that my ordeal was finally over. That is, until my mother's next utterance. "Would you like to finish up, Becky?"

Noooooooo!

"Would I!" she said, and before I knew what hit me, Becky was in the chair, and I was face down on her lap. "Come help me, Brenda!" said my excited sister.

"Love to!" said Brenda, who instantly was on one knee next to me, facing Becky.

"I'll do the left cheek and you do the right," instructed Becky.

"Got it!" replied Brenda.

"Readyyyyy, go!" shouted Becky.

Without further ado, the girls went at it, and I felt a steady flow of simultaneous slaps on my now-traumatized backside.

"You're missing a spot!" said Becky at one point. "Just off to the side—it's not red yet."

"I'm on it!" said Brenda as I felt the slaps on a spot they had not yet covered.

They continued their barrage, and the pain was becoming unbearable. "Ow! Oh! Stop! Please! Mom, make 'em stop!"

"Alright, girls, I think Blondie has had enough," announced my mother. "Good job; you warmed him up quite nicely."

Indeed, the girls let up, and I clumsily extricated myself from my sister's lap. I turned away from everyone and held my backside with both hands. It felt like I had been set on fire back there. "Oh! Oh!" I said out loud while absorbing the pain.

"Mother, can you make Blondie go stand in the corner for a while for being the bad little boy he is? I remember you did that once after one of his spankings."

"Sure, I think that's appropriate. Blondie, go stand in that corner while you think about your naughty behavior and the consequences it brings." She pointed to a corner of the living room that was right next to the flat-screen TV, which was mounted to the wall. I quickly walked over there and planted my nose against the wall. My hands still covered my buttocks.

"Hands on your head," was my mother's somewhat predictable command. I did so and could almost feel three pairs of eyes zeroing in on my glowing rear end.

"Hey, wanna watch a Seinfeld?" said Becky.

"Sure, we could do that," answered my mother.

Within moments the TV was on, and they were all sitting on the sofa. Then, just as the episode was starting, the doorbell rang.

Uh-oh.


Yet More Visitors

"Oh, that must be Joanna and Marcia," said Becky as she got up from the sofa. "I told them if they came over it would be worth their while."

You've got to be KIDDING me!

I made a move away from the wall and was immediately reprimanded by my mother. "You stay right where you are!" she ordered.

"Please, Mom!" I pleaded while facing the wall again. "Let me go before they come in!"

"I don't think so," answered my mom. "I'm not quite done with you yet."

Within moments I recognized the voice of Joanna. It took her a couple of moments to notice that Becky's naked brother was in the room. "Thanks for inviting us over, Beck," she said. "I'm really curious why you said it would be worth......oh, my God!" Then, "Why is Blondie naked?"

"He's being punished," answered Becky merrily.

"Wow! I can see that. Look how red his little fanny is!" said Marcia.

"Did you do that, Mrs. Haggerty?" asked Joanna.

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

"Hey, have a seat," offered Becky. "We're just about to watch a Seinfeld."

"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 as they watched the episode.

I had to endure many cutting remarks throughout. For instance: The Seinfeld episode they watched was the one that took place in the Hamptons. In one scene the George character had gotten out of the pool and was changing in his bedroom. A woman walked in on him while he was fully exposed. Supposedly his penis had shrunk because of his extended pool time. The woman looked down at his penis and grinned while putting her fingers to her lips.

"It still was probably bigger than Blondie's," said Brenda, to the tune of more laughter. I felt my face flush; though no one could see it, I'm sure it was as bright as my ass cheeks.

Finally, the episode ended, and so would my ordeal. "Okay, Blondie, you can go get dressed now," declared my mother. "Say good-bye to your guests and go up to your room."

"Bye," I said as I put my hands over my crotch and dashed toward the stairs.

"Blondie! Don't be rude," called out my mother. "Turn and face your guests and thank them for coming."

I turned, and said, "Thank you for coming." Mercifully, my mother did not make me move my hands.

"No, thank you!" answered Marcia.

"Yes, the pleasure was all ours!" chimed in Joanna.

I turned once again and scampered up the stairs, leaving five delighted and amused females in my wake.


Owned by My Sister

About an hour later my door opened. I looked up to see a smiling Becky. Normally she would have been required to knock, but evidently that ship had sailed. "I own you now, Blondie,” was all she said before turning back and quietly closing the door.

As I lay on my bed still trying to process the abject humiliation I had endured, I considered what I had just heard. Much to my dismay, I recognized that indeed, it was oh, so true.

Roosevelt Humiliations, Chapter 13

Posted: Tue Jan 16, 2024 3:26 pm
by Blondie
Image

Chapter 13: Under My Sister’s Control

Becky’s Dominance

I know it’s been awhile since I’ve chronicled my latest disgraces at the hands of my sadistic tormentors. You see, it’s quite difficult for me to recount, as my humiliation intensified throughout my junior year. But I’m hoping it will be good therapy for me to continue with this account, so I’ll trudge on.

You may recall when we last connected that my sister Becky joined Mitch, Brenda and the gang in their fun at my expense. Since then, Becky has been a major thorn in my side. She still brings up the time my friend and I purposely walked in on her while she was taking a bath. That incident has really stuck with her, and she has been taking great pleasure in her retribution now that she has the upper hand on me.

She didn’t take long to use her newfound dominance over me. It was the morning after my mortifying experience at the beach, the gas station, and the god-awful encounter with my mother. I was sitting alone in my room reading the sports section. I was still trying to recover from the horrid events from the previous day. Suddenly, without knocking, Becky let herself in. “Brother Blondie,” she said, “Would you be so kind as to clear my dishes off the dining room table and wash them for me? Oh, and when you’re done with that you can make my bed.”

I sat dumbstruck and agape for a few seconds. “B-but…”

“No ‘buts’ about it, my little pet. I own you now, and unless you want to find yourself stark naked in public again, you’ll abide by my rules. Now I’m going on a bike ride, and when I get back I expect my chores to be done. And since you put up a fuss, you can clean up the mess I left in the bathroom, too. The sink in there is filthy. I swear, it seems like whenever I brush my hair, half of it ends up on the sink. And the toilet needs a good scrubbing, too. Make sure you scrub underneath the lip; it’s absolutely disgusting.

"Also, I noticed there are a couple of stray pubic hairs on the floor—they must be mine, ‘cuz they’re too long to belong to you—I don’t want to see those when I get back. You’ll find my panties on the floor; you can just put them in the hamper. And if I get any more backtalk, you’ll find yourself wearing them to school tomorrow.” She paused and smiled to herself. “Now that I think about it, I think you’d look rather cute in my panties.” With that she disappeared out the door, her laughter resonating throughout the hallway. My younger sister had become a little monster.

Reluctantly, I washed her dishes and made her bed. I then cleaned the dirty bathroom. I picked up her panties with my thumb and index finger, and while grimacing, I carried them through the hallway to the hamper. I shuddered while recalling her threat to make me wear them to school. At that point I wasn’t putting anything past her. And I'd probably be forced to show them to anyone who asked.


Lacy Anklets

For the next few weeks Becky continued having me do her chores for her. She told our parents that I had lost a bet, so they didn’t bat an eye at my subservience.

As much as I hated doing my sister’s bidding, I took solace in the fact that at least I was spared any major humiliation. But as you may have guessed, that would be a temporary situation, which ended one Saturday in late October. Our parents were away for the weekend, and I had decided to escape for a while and go take in a matinee. I tiptoed through the hallway and quietly turned the doorknob before I was interrupted.

“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. “I’ll be right back.”

“No, you stay here. I need you to drive me to the mall today. Mom gave me the use of her credit card, and I want to do some shopping.” I bowed my head and disconsolately came back in and sat down in the living room. “And how dare you try to go out without telling me,” Becky scolded. “Just for that you’ll have to be punished.” She paused and stood with her hand on her chin and her index finger over her lips, as if deep in thought. “Yes, I’ve got just the thing for you,” she said as she disappeared into her bedroom.

I remember cringing while wondering what the mischievous little devil had in mind for me. To my chagrin, she returned holding in her hand a pair of her girlish white tennis shoes, along with a pair of white anklets, complete with lace all around the tops. She dropped them at my feet. “Here you go, brother Blondie,” she said. “Now take off your shoes and socks and put these on. I want you to wear these today while we go shopping.”

I looked at her, horrified. I was wearing a pair of shorts, and the thought of wearing her shoes and very feminine socks out in public was incomprehensible. “Please, Becky, I’m sorry, I didn’t know you needed me today. I promise I’ll ask your permission from now on when I want to go out. Please don’t make me wear these,” I implored.

“I have a cute little skirt that would look darling with those shoes and socks,” was her response. “Would you like me to go get it or are you going to put those on without giving me any more lip?”

Without answering I forlornly leaned over and removed my shoes and socks. Reluctantly I pulled on the lacy anklets, followed by the tennis shoes, which unfortunately fitted me perfectly. I leaned back in my chair, trying not to look at my newly adorned feet and ankles.

“Stand up, Blondie,” ordered the grinning Becky. “Let’s have a look.” I stood up and Becky took my hand and led me to the middle of the living room. "Hmm," she said as she scrutinized my legs and footwear. "You look adorable, but we need to do something about those shorts. I'll be right back," she said as she headed back to her bedroom.

Wait, what's wrong with these shorts?

I waited anxiously, wondering what Becky had in mind. Surely she didn't expect me to wear a skirt out in public.

Becky reappeared momentarily. She didn't come back with a skirt, but it was probably the next worst thing. Smiling, she held up a pair of short, white shorts. 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 said. "This way you can show off more of your pretty legs."

I stood transfixed. "Oh, God, please, Becky," I pleaded. "I can't wear those out in public."

Becky turned and started walking toward her bedroom. "Okay," she said. "A skirt it shall be."

"No! Wait! Okay, I'll do it!"

Becky stopped and turned around with a grin on her face. She probably had a pretty good idea it would go that way.

I took the shorts from her hand and started to walk to my bedroom before Becky stopped me. "You can change right here, brother Blondie," she said. "No need to be shy. After all, I just recently saw you naked."

Defeated, I turned my back to Becky, dropped my shorts and stepped into the short shorts, while hearing Becky giggling behind me. They were tight, and indeed waaaay too short. I pulled on the hems in an 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.

“Oh, this is precious,” teased Becky as she did a 360 around me while staring at my legs and feet. "You need to tuck your shirt in, though." I was wearing a blue tee shirt that was hanging down almost to the hem of the shorts. I dutifully tucked it in. I just stood there, staring straight ahead and blushing profusely.

Becky kneeled and adjusted the anklets to her liking. “Come, you must have a look at this.” She was enjoying herself immensely as she again took my hand and led me to her bedroom, where she stood me in front of a full-length mirror. She continued taunting me, lightly holding my elbow and kissing me on the cheek. “Don’t you look just darling, brother Blondie?”

I couldn’t muster up an answer, as staring back at me was a tall, slim, red-faced sixteen-year-old boy wearing short shorts, lacy socks and girl’s tennis shoes. If Becky's aim was to make me look girlish, then she was successful, much to my embarrassment. I had grown some hair on my legs, but it wasn't much, and it was fine and very light-colored, so it was hardly noticeable. I turned away from the mirror, having seen quite enough.

“Too bad we don’t have time to shave your legs; that would be a nice touch. Maybe some other time. Time to go now.”


Brenda's House

With that she tossed the keys to the car to me and headed toward the door. I was about to argue, but the image of me in a skirt changed my mind, so I followed her out submissively. Once outside, I looked around nervously, as I was quite cognizant of my attire. Though the shoes and socks weighed only a few ounces, it felt like I was dragging a pair of balls and chains. And the breeze blowing on my bare thighs helped remind me of the short shorts—not that I needed a reminder!

I ran to the car in the driveway while Becky ambled slowly, grinning broadly. Once Becky got in, I started the car and backed out of the driveway, dreading what lay ahead for me.

“Take a left at the stop sign,” ordered Becky. “We have to go pick up Brenda.” She watched me as my shoulders slumped. My spirits were dampened even further, as it appeared that my other main nemesis was about to partake in whatever sordid events were about to unfold. Much to my consternation, Brenda and Becky had become good friends over the last month. They certainly had something in common, that being their unbridled enjoyment of my humiliation.

“I didn’t tell her about your attire; I thought we’d surprise her,” said Becky. I didn’t respond, and Becky pinched my cheek between her index finger and thumb and jiggled it back and forth. “We’re going to have so much fun today, brother Blondie!” I continued driving, looking straight ahead, longing for the day to end.

“Slow down, this is it,” declared Becky. "You can just pull into the driveway."

I did so, in front of a beautiful, sprawling, two-story house—a borderline mansion, in my estimation. I waited for Becky to get out, but instead she directed, “Why don’t you go ring the doorbell. Brenda’s expecting us.”

I looked at my sister pleadingly, but in short order I ascertained that she would be unyielding. I got out of the car and, still very self-conscious, looked around anxiously and trotted to the front door. I rang the doorbell and stiffened when a woman, decidedly Brenda’s mother, answered the door. She did a double take at my legs and feet, and a look of surprise came upon her face.

“Is Brenda here?” I asked.

“Um, yes, would you like to come in?” Again she eyed my feet curiously.

“No thanks, if you could just tell her that we’re here to pick her up…” My face was flushing, and I was fidgeting nervously.

She turned her head and yelled, “Brenda, there’s a young….” She turned back and looked closely at my face. “There’s a young man here to see you.”

Within moments Brenda appeared at the door. “Hi Blondie,” Brenda greeted with an effervescent smile. As her gaze inevitably lowered down my legs, her eyes lit up and she grinned widely. “Oh, what darling little socks! And they set off your pretty legs so nicely." She looked me up and down and grinned some more. "And such cute little shorts. Did Becky help you get dressed today?”

I glanced at Brenda’s mother, who now was also smiling. 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 as she shared a laugh with her mother.

As mortifying as that experience was, there was no rationale for me to think things would get any better as the three of us drove off to the mall.

Re: Roosevelt Humiliations

Posted: Tue Jan 16, 2024 6:28 pm
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.

Re: Roosevelt Humiliations

Posted: Wed Jan 17, 2024 12:09 am
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!