Roosevelt Humiliations

Stories about boys ending up in compromising situations, preferably naked and embarrassed, as the name suggests.
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Blondie
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Roosevelt Humiliations, Chapter 25

Post by Blondie »

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Chapter 25: Shrinkage

Naked on the Barstool

When the laughter had finally settled a bit, Brenda headed into the kitchen and returned carrying a tall barstool. She set it down right behind me.

“Have a seat, Smoothie,” she grinned. “Rest those weary little legs. We girls know how exhausting it is walking around in heels all night.”

I climbed up onto the barstool, knees together, and leaned forward, folding my arms across my thighs in a feeble attempt at modesty. Naturally, Brenda wasn’t having any of that.

She came up behind me and gently tugged me back by the shoulders until I was leaning stiffly against the barstool’s backrest. “I want you to be comfy, Blondie. Just kick back, relax, and enjoy yourself.”

Right, like that’s even remotely possible.

Then she took my wrists and rested them lightly on the barstool’s arms. “That’s it. Just rest your arms here.” Next, she pulled my knees apart, then placed my ankles up on the leg rests on either side of the stool, leaving me exposed to the max. “We’re all friends here, sweetheart. What’ve you got to hide?” She glanced down, then smirked. “Very little, from the looks of things.”

That quip earned a fresh round of animated laughter, and Brenda settled smugly back onto the couch.

Once things quieted down again, Becky picked up the thread. “You’re awfully quiet, Blondie,” she said sweetly. “Say something. We never talk anymore.”

Everyone perked up a little, clearly intrigued by the prospect of hearing me speak. But I stayed silent—I wasn’t exactly eager to provide running commentary on my own humiliation. Naturally, they all knew that too.

“We’d really like to hear about your alone time with Felicity a little earlier,” prompted Becky. “You two were gone a long time. Let’s hear all about it.”

The last thing I wanted to talk about was my one-on-one humiliation at the hands of Felicity. Of course, Becky knew as much. I remained reticent.

“Blondie, I don’t think you’re in any position to be obstinate right now. As you well know, Mitch will drop your naked ass downtown at the snap of my fingers—I don’t think you’d be interested in public nudity, especially now that you’ve got a bald little clitty.”

While I sat there blushing crimson, the room erupted in laughter again.

“Not only that,” she added when the noise simmered down, “we’ve got plenty of pics of you tottering around in those cute pink heels, plus a fantastic video that we’ll all be watching tomorrow night over popcorn. I do think that it’s in your best interests that these visuals don't accidentally get loose around Roosevelt High. Need I say more?” I shook my head disconsolately. “I didn’t hear you, little girl.”

I winced at the “little girl” reference. “No, I understand,” I finally relented, cheeks burning crimson.

“Good.” Becky leaned back and took a leisurely sip of her beer. “So, when I came to tell you Mitch had arrived, you were in a very interesting position. Why don’t you tell us about that, Blondie.”

It was clear there was no escaping this. I spotted Marcia with the video camera trained squarely on me.

“Felicity made me take off the clothes I was wearing,” I said stiffly.

“I’m warning you, Blondie,” Becky said. “We want details. All the details.”

I took a shaky breath. “When you walked in, I was standing on the stool. I only had the panties on at that point. Before that she took off my shoes and socks, the dress, and the petticoat.”

I paused, fidgeting, as their grins widened.

“Go on,” Becky prodded.

“Then she started pulling down the pan—”

“Hold up, Blondie,” Felicity cut in. “Tell them about the song. And why you had to sing it.”

I paused momentarily to gather myself. “Since I would soon be in my birthday suit I had to sing ‘Happy Birthday’ to her while she pulled down the panties.”

Everyone giggled and looked over at the beaming Felicity. They seemed appreciative of her creativity, and Felicity had a proud look on her face.

“That’s when you came in,” I finished weakly.

“Excellent!” said Becky brightly. “See, that wasn’t so bad now, was it?”

Actually, it was excruciating.

“Now I want to hear about how you lost your little pubies. And look at us while you tell us.”

Of course. I knew that was coming. I looked up at the row of amused, expectant faces and took another deep breath.

“First she used scissors.…please, don’t make me tell this.”

“Oh, pray tell, Smoothie, pray tell!” Brenda laughed. “You’re turning into quite the little storyteller!”

I closed my eyes briefly and pressed on. “F-first she used scissors. And I had to sing. When most of it was cut off, we went into the bathroom—”

“Wait, wait, wait!” Becky interrupted, leaning forward eagerly. “Back up. You had to sing? Was it ‘Happy Birthday’ again?”

“No, she made up a different song. Please—”

“Oh, you have to sing it for us, Blondie.” Becky held up her hands theatrically and turned to the group. “Who here wants to hear the song Blondie sang while the little hairs on his little wee-wee were coming off?”

Of course, the response was a gleeful chorus of affirmatives.

“Sing it for us, sweetheart,” she said with a grin.

I hesitated, then finally gave in. My voice trembled, but I managed to get it out.

♬ “My little pee-pee has no hair. Ee-eye-ee-eye-oh.” ♬

They were already losing it.

♬ “With a snip-snip here, and a snip-snip there. Here a snip, there a snip, everywhere a snip-snip….my little pee-pee has no hair. Ee-eye-ee-eye-oh.” ♬

The room was shaking with laughter by the end. Mitch was stomping his feet, clutching his sides.

“Tell them about the snips, Blondie,” said Felicity proudly.

“W-Whenever I sang the word ‘snip’ she snipped off some of my hair down there with the scissors.”

That set off another round of wild laughter, while Felicity looked like she'd just been handed a trophy.

“Ingenious, Felicity,” Becky said with admiration. “Positively ingenious.”

“Thank you,” Felicity replied, now quite full of herself.

“I have a question,” Brenda cut in smoothly.

All eyes turned toward Brenda as it quieted down. She paused dramatically while everyone leaned in, waiting expectantly. “Is it true,” she asked, “that if a guy spends time in a cold pool....it shrivels up?”

Naturally, every pair of eyes immediately shifted to my smaller-than-average penis. My self-consciousness, already through the roof, somehow managed to soar even higher. I instinctively tried to close my knees, but with the way my legs were positioned on the chair, I couldn’t move them.

“Well, Blondie?” continued the unrelenting Brenda. “Is it true?” The gazes rose to my blushing face.

“I-I don’t know,” was my response, while staring at several pairs of feet on the floor in front of the couch. “I don’t think so,” I stated, hoping to nip this conversation before it advanced any further. But that hope was soon shot down.

“Oh, it’s true,” Mitch chimed in casually from the end of the sofa.

Felicity was ready with her next jab. She gestured to my lap with exaggerated surprise. “Well, then it must be freezing in here already. Because it can’t get any smaller than that, can it?

Once again, the redoubtable Felicity had elicited laughter from the entertained group. My cheeks turned scarlet.

“There’s one way to find out,” Becky said, already up from the couch, grinning ear to ear.

I looked at her in alarm. I could already see where this was going. She took my hands and pulled me up from the barstool. “Come on, sweetie pie. Let’s take you for a little dip.”

The whole group sprung from their seats, enthusiastic about the new devilish plan. Becky knelt to slip the high heels off my feet and tossed them aside. Taking my hand, she led me down the hall. “Let’s go in the bathroom and clean off your face. We wouldn’t want your makeup to dirty up the pool.”

“Becky, please,” I begged, panic setting in. “The pool’s not even heated.”

“Precisely, my dear,” responded my unmerciful sister with an unmistakable twinkle in her eye.

She ushered me into the bathroom and got to work removing the makeup from my face. As she did, she called out, “You all might want to grab a sweater or something. There’s a bit of a chill in the air tonight.”

“Good idea, Beck,” answered Joanna while she and the rest scampered for their wraps. “It's getting nippy out there, and the wind really adds a bite to it.”

The absurdity of my situation wasn’t lost on me—while everyone was bundling up, I was about to go out there without a stitch on, and then jump into a cold swimming pool to boot.

Becky finished her task in short order and led me into the hallway. “Wait here, sweetie, while I go get my sweater.”

I stood in the hallway, momentarily alone, and shivered in anticipation. Suddenly: SLAP! Then I felt a slight stinging sensation on my backside.

Julie giggled, having just delivered the playful swat. “Let’s go, cute cheeks,” she teased, throwing an arm around my waist. Then, glancing down, she added with a smirk, “Time to see if your little weenie can get even weenier.”


The “Before” Measurement

While giggling at her derisive remark, she led me to the large pantry, where a festive, eager group stood near the back door. They were properly attired for the chilly night air. I most certainly was not.

Someone opened the back door when Becky interrupted. “Hold it!” she barked. She held a roll of measuring tape above her head. A few inches of the tape dangled from the roll. “We need to get a ‘before’ and ‘after’ measurement,” she said with a wicked smirk. Everyone leered at me. “Who wants to measure Blondie’s little winkie?” she asked sweetly.

Several hands shot up amid excited giggles.

“Well,” Becky laughed, “you can’t all do it. Let’s let the birthday girl do the honors.”

The delighted Felicity sprung forward. “Oh, goodie!” she yelled while snatching the tape from the grinning Becky.

I groaned as she knelt in front of me, tape measure in hand. She looked up at me and smiled. “Isn’t this fun, Blondie?” she teased, brushing her hair out of the way. I remained silent, unbelieving of what was transpiring.

Felicity looked down at her objective. “Becky,” she requested, “Would you mind holding his little thingy up while I measure it?”

“Sure,” laughed Becky. She placed two fingers underneath my penis and held it up. The humiliation of my sister handling my penis under the extremely embarrassing circumstances was torturous.

Felicity stretched the tape across the length of my penis. To obtain a reading, she lowered her head very close to my midsection and squinted at the numbers. I felt her hair brush against my bare stomach.

“It looks like two and one-eighth inches,” she announced gleefully, eliciting giggles and guffaws from the entertained group.

“If this pool thing really is true, then we’ll need a magnifying glass to see how long—I mean how tiny it is,” Cheryl quipped.


The Pool

The pool light was on, and the entire area was well lit. The chilly air—I’d say the temperature was in the mid-forties, and there was a steady breeze to boot—sent shivers throughout my body, and immediately produced goose bumps all over. I folded my arms across my chest in a futile attempt to stay warm.

“Brrrr,” Joanna shivered. “It really is chilly out here.” She looked at me and said, “You must be freezing, Blondie.” She looked down at my penis, which may have dwindled in size already. I could tell that my scrotum had tightened and contracted. “You may not need to go in the pool, little boy," taunted Becky. "I think it’s already shrinking.” The comment generated another chorus of laughter, and I self-consciously lowered my hands and covered my shriveling package as we approached the pool.

“Let’s see,” Becky mused aloud. “What’s the best way to do this?” She snapped her fingers. “I know—you should go down the slide, Blondie. I know how much you love the slide.”

Groaning inwardly, I trudged over to the ladder. I’d climbed it hundreds of times before—but never like this. Never naked. Never with a pit in my stomach and an audience ridiculing me through every step. As I began the slow, shameful ascent, the laughter behind me grew louder—partly mocking their naked victim, partly eager for what would come next.

At the top, I perched nervously, my legs trembling as I looked down. Thirty feet below, they were already chanting.

“Go Blondie! Go Blondie! Go Blondie!”

With no other choice, I gave myself a silent countdown and pushed off. No reason to delay the inevitable. I slid down to the accompaniment of cheers, clapping and laughter. I braced myself for the shock.

I had seriously underestimated its extent. Sure, anyone who’s jumped into a cold pool knows there is an initial jolt—but this was on a whole different level. It felt like a charge of electricity had surged throughout my body. When I surfaced, I was still overcome from the shock to my system.

“Ah! Ah! Oh shit! Shit! Oh God! It's freezing!” I screamed. My tormentors were laughing and cheering. I swam toward the side of the pool, intent on escaping the biting cold.

“Uh, uh, uh!” admonished Becky as she used her foot to obstruct my effort to climb out of the pool. “You need to spend a few minutes in there, Blondie boy, to get the full effect, if you know what I mean.” She paused and giggled to herself. “Now go out to the middle of the deep end and stay there until we tell you to come out.”

I obeyed, and treaded water for what seemed an interminable amount of time, shivering all the while.

“I think it’s getting smaller,” observed the squinting Marcia after a couple of minutes.

“I’ll say,” chimed in Julie as she bent from the waist and peered in my direction. “I can barely see it!” she exclaimed, eliciting more hearty laughter.

I reached down and surreptitiously checked it out myself. Much to my dismay, there indeed had been a change. The cold water had done a number—there was nothing there but a little nub! “Oh, God,” I said to myself in a semi panic. I turned my back to the group and pulled on it, hoping to pull it from its depths. But the forces were against me, and in mere moments my humiliation would be exacerbated.

“Okay, Blondie,” called Becky, right on cue. “Come on out, let’s have a look.”

I swam toward the edge of the pool, where eight pairs of eyes were fixed on me, each face a mix of amusement and eager anticipation. Just before climbing out, I reached down in a final, futile attempt to restore what the cold had claimed. I pulled on my shrunken penis, almost pleadingly, in one last desperate effort to somehow resurrect it to its regular size.

I don’t think it helped.

“Oh my God, check it out!” shrieked Brenda when I climbed out of the pool, causing me to instinctively cover myself with my hands. Immediately I heard three loud slapping sounds, which was followed by a sharp stinging on my wet backside.

“Put your hands on your head and keep them there!” ordered Becky.

Blushing furiously, I complied. And just like that, the floodgates opened—the teasing came fast and mercilessly.

Becky: “Oh my gosh....it really did shrink!”

Marcia: “Did it just….disappear? I swear it was there before!”

Julie: “Okay, that’s seriously the tiniest one I’ve ever seen.”

Cheryl: “I can barely see anything!”

Joanna: “Oh, this is too much!”

And, of course, Felicity: “Blondie, sweetie….you might actually be breaking records right now.”


(Not) Measuring Up

“Come on,” Becky said, grabbing my hand. “let’s go in the poolroom. We must get a measurement of this."

Of course, everyone eagerly followed. It was warmer there, but I was still dripping and shivering and mortified beyond belief.

For the first time, I afforded myself a look at my shrunken state. I’ll never forget the sight and the feeling of disbelief I experienced at that moment. I could barely see the head of my penis sticking out from my midsection, and my ball sack had shriveled up to almost nothing. And of course, I was completely devoid of hair. I swear, it looked like I had the genitals of a two-year-old!

The grinning Felicity approached me with the measuring tape. “I don’t need your help this time, Becky,” she stated gleefully to yet more laughter. “There’s nothing to hold up anymore.”

Indeed, she was right. My little penis was sticking straight out, it’s lack of size and weight keeping it from drooping down. Felicity bent over and once again stretched the tape across my now almost-absent penis. She came up beaming.

“One and three-quarters!” she announced gleefully, much to everyone’s utter delight and amazement.

“Aww, such a cute wittle baby boy,” Becky cooed, giving the underside of my chin a playful tickle with her fingers.

“Does wittle Bwondie need a diaper?” mocked Julie.

The hilarity was now at its highest point of the evening, as was my mortification. I stood there helpless—hands on my head, shivering, and soaking in the full weight of my humiliation.

Cheryl lowered a camera to the object of everyone’s amusement and snapped a couple of pictures. Mitch was gleefully capturing a video. I remember thinking that with this moment caught on camera and video that I may never live this godawful experience down. That no matter how hard I try to get over this, there will always be a picture, a video, or a knowing smile. That my humiliation will never completely subside.

* * * * *

I think I’ll stop here for a while. I do have one more episode in store for you, but chronicling these latest events has left me spent. I’ll try to muster up the nerve to relate to you the last shameful experience I had at the hands of the loathsome terrors from Roosevelt High.
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