Roosevelt Humiliations: The Missing Chapters

Stories about boys ending up in compromising situations, preferably naked and embarrassed, as the name suggests.
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Roosevelt Humiliations: The Missing Chapters

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The following is applicable to all chapters of “Roosevelt Humiliations: The Missing Chapters:"

© March 2020 by Blondie.

This is a work of fiction, and is fantasy only. Names, characters, places, and incidents are products of the author's imagination and are used fictitiously. Any resemblance to actual events or locales or persons, living or dead, is entirely coincidental.

For ages 18 and older only.

Chapter 1: Detained
Chapter 2: Punishment
Chapter 3: Servitude
Chapter 4: Disciplined
Chapter 5: Crumpets

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Author's Note: I wrote the story "Roosevelt Humiliations" about 20 years ago. There was one scene where the Blondie character was on the way to the mall (against his will) with his sister Becky. (It can be found here, if interested.) They stopped at Becky's friend Brenda's house to pick her up. Blondie was wearing short shorts, girlish white tennis shoes and lacy anklets (also against his will, of course). Becky sent Blondie out of the car to ring the doorbell, where Brenda's mother answered the door. She was quite intrigued by Blondie's attire.

I always felt that I could have done more with that scene, and more than 15 years later I sat down to make an adjustment. I proceeded to get carried away, and instead of a modification it turned into a five-chapter story of its own. Below is the result of that "modification."

It's a bit different than what we usually see here (and what I'm used to writing), in that the character's humiliation is carried out by group of posh, middle-aged ladies at a tea party. I enjoyed writing it up, and I hope you will find it entertaining.


Chapter 1: Detained

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

I did, easing her car up the drive of a beautiful, sprawling two-story house—borderline mansion, really. I expected Becky to hop out, but instead she folded her arms and smiled.

“Why don’t you go ring the doorbell? Brenda’s expecting us.”

I looked at her pleadingly, but her smirk said everything. I was not getting out of this.

With great reluctance, I climbed out, painfully aware of the ridiculous outfit she’d stuffed me into: short shorts, girlish white tennis shoes, and—worst of all—frilly lacy anklets. I glanced around, praying for invisibility, then trotted up to the door and rang the bell.

It opened almost instantly. A woman—clearly Brenda’s mother—stood before me. She did a double take at my legs and feet, her expression one of amused curiosity.

“Is Brenda here?” I asked, trying not to fidget.

“She is, yes. Would you like to come in?” Her eyes dipped again to my socks.

“No thank you,” I stammered. “Could you just tell her we’re here to pick her up?” My face was flushing.

She turned slightly and called out, “Brenda, there’s a young—” She paused, clearly reassessing. Her eyes scanned my face, chest, then drifted once more down my legs. “A young man here to see you.”

Again she looked down at my legs, then back up to my face. I thought I detected a smirk on her face. She stuck out her hand. “I’m Elizabeth, Brenda’s mother,” she offered.

“Blondie,” I muttered, shaking her hand.

“Well, it’s lovely to meet you…Blondie,” she said, lingering a moment too long on the name.

Once again she looked down, then back up to my face. I felt like I was burning up; I'm sure I was blushing crimson.

"I'm having a few of my lady friends from the poetry group over for tea. Would you like to come in and meet everyone?" she asked.

Not even in the top 1000 of something I'd like to do.

"N-no, thank you," I politely declined. I started backing away, ready to return to the sanctuary of the car as quickly as possible. "It was nice meeting you. Please tell Brenda we'll be in the car."

But just as I started to turn away, I was waylaid by my nemesis. “Hi Blondie!” Brenda greeted me. "Did you introduce yourself to my mother?"

As her gaze inevitably lowered down my legs, her eyes lit up and she grinned widely.

“Ohhh, what darling little socks!” she cooed. “And they show off your legs just beautifully. Are those Becky’s shorts? Did she help you get dressed today?”

I didn’t answer. I glanced at Brenda’s mother, who now was also smiling.

"I wanted to have him come in for a minute and meet my poetry group," she said. "But he turned down the offer. I think he's a little shy, he was blushing so. And maybe you two are in a bit of a hurry."

"Oh, nonsense, Mother. Blondie would love to come in and meet everyone," responded Brenda. "Wouldn't you, Blondie?"

Before I could protest, she took my hand and tugged me toward the door.

“Please, Brenda, can we just go?” I pleaded.

But she tugged harder, this time with both hands, until I was inside the door, standing in the foyer.

"Don't be rude, Blondie. My mother wants to introduce you to her friends. I think she has taken a liking to you. The least you can do is come in and say hello."

Brenda's mother stepped in, gently guiding my elbow. “Come now, young man. I’m sure the ladies will be quite enchanted.” I caught her winking at Brenda.

Like mother, like daughter.

I looked back and saw that Brenda had opened the front door and was motioning with brisk hand gestures for Becky to come in.

Huh? Why does she want Becky to join us? I don't like this.

Much as I wanted to resist, I knew we weren't going anywhere until I did their bidding. With Brenda close behind, her mother led me into her living room. She let go of my hand when we reached the center of the room.

Sitting about the room were four undoubtedly well-to-do ladies, all elegantly dressed and wearing posh hats, and all about forty-something. There was even a maid in a classic black dress with a white pinafore and bonnet.

"Ladies," began Brenda's mother, "I'd like you to meet Brenda's friend. His name is Blondie."

She paused while I stood there blushing as they sized me up.

"Blondie, this is Josephine in the French Louis chair, that's Katarina and Tatiana on the loveseat, and this is Charlotte sitting in the Victorian piece."

Why she felt the need to identify her furniture while introducing her guests was beyond me. I guess that's just what some of the upper crust do. Whatever, all I knew was that I could sense the stares and just wanted to get the hell out of there as quickly as possible.

Just then, Becky entered the room, providing a temporary distraction from their focus on me.

“Hello, Becky,” Elizabeth said warmly. “We were just introducing Blondie to my friends. Ladies, this is Brenda’s friend Becky.”

“Lovely to meet you all,” Becky said with a gracious nod.

There was a pause—tense for me, but apparently delightful for them—until Josephine broke the silence.

“Pardon me if I’m overstepping, young man, but I must say, your choice of attire is…rather intriguing.”

With all eyes on me, I stood there blushing, not knowing what to say. But Becky took care of that.

“He’s being punished,” she said, her grin practically gleaming.

The room gasped as one. If the ladies were intrigued before that pronouncement, they were absolutely enthralled at this point.

“Oh, do tell!” exclaimed Charlotte with a sweet Southern accent.

"Are you saying his outfit is not of his choosing?" asked Tatiana, visibly delighted.

I fidgeted nervously as the ladies leaned in, clearly intrigued by my predicament.

"My, look at the lad blushing so," Katarina observed. “He seems dreadfully self-conscious, doesn't he?”

Of course, the comment only caused my face to flush even brighter, an effect that seemed to delight the group of ladies.

“Oh, he is,” Becky said, clearly enjoying every second. “So, the shorts, socks and shoes he is wearing belong to me, and it is safe to say that he is not pleased in the least to be wearing them, much less having to display himself in public like this."

The ladies were now thoroughly captivated.

"Becky," pressed Brenda's mother Elizabeth, "Would it be presumptuous on our part to ask what kind of transgression Blondie committed to deserve such an embarrassing punishment?"

Becky raised her voice just a touch, ensuring the room could hear every word.

"Not at all, Mrs. Hollister. I think you should know, and after I tell you I'm certain that you won't have any sympathy for him."

The ladies regarded me in breathless anticipation; even the maid stood transfixed.

"You see," continued Becky, addressing all the ladies, "I was relaxing in the bath one evening, and Blondie—he's my brother, in case you didn't know—Blondie had one of his friends over. Well, the little creep picked the lock on the bathroom door and he and his friend came barging in on me. They were standing over me, staring at me like little perverts."

The collective gasps emanating from the five ladies left no doubt as to their level of disapproval.

“My word!” Josephine exclaimed.

"Such despicable behavior!"” cried Charlotte.

“Abominable,” said Katarina.

“Detestable,” agreed Elizabeth.

“Reprehensible!” added Tatiana.

"I know!" said Becky. "So now—and it's a long story how it came to be, and that's not important right now—Blondie is under Brenda's and my control, and we are making him pay for his dirty deed."

“As well you should!” Katarina said. “The nerve of him!”

Brenda's mother looked at me with piercing eyes. "What do you have to say for yourself, young man?"

“I…I’m sorry,” I mumbled. “It was just supposed to be a joke.”

“A joke?” Elizabeth repeated, aghast." A sick joke, at best. I'll bet you don't think it's so funny right now, do you?"

I shook my head, eyes on the floor.

Josephine leaned forward, tapping her chin. "Miss...it's Becky, right?" Becky nodded and Josephine said, "Do you think this punishment quite fits the crime?"

Becky had an inquisitive look on her face and said, "What exactly do you mean, ma'am?"

“Well,” Josephine said, “while the boy’s ensemble is doubtless a source of acute mortification for the young rascal, he did catch you in a far more revealing moment, you poor dear. It seems only proper that he endure a touch of exposure himself, for the sake of balance.”

“Oh, I do adore the idea!” Charlotte giggled behind her fan. "A young gentleman ought to learn that actions carry consequences—preferably embarrassing ones.”

“Oh, yes!” said Tatiana. “An eye for an eye.”

“A tooth for a tooth,” Katarina chimed in.

“Tit for tat,” said Charlotte with a grin.

“Poetic justice,” added Katarina.

“Poetic justice from the poetry group?” Josephine chuckled.

Elizabeth nodded thoughtfully. “I think that’s a wonderful idea. At the very least, he should be required to disrobe to his underpants."

“Hear, hear!” Katarina said, practically giddy.

My heart rate skyrocketed. This was getting out of hand. These ladies seemed to be chomping at the bit over an opportunity to humiliate me.

“Wait! Please—” I tried to protest. "They've already seen me na—"

But Elizabeth was already addressing Becky and Brenda. “Girls, are you two in a rush? Or can you stay a bit longer while we teach this young man a proper lesson?”

Becky and Brenda looked at each other and grinned.

A chance to see me humiliated by a bunch of posh ladies at a tea party? Gee, I wonder how they'll respond.

“Oh, we’re in no rush, Mrs. Hollister,” Becky said sweetly. “We can stay as long as you like.”

“Excellent,” Elizabeth purred. “Now, ladies—how shall we proceed?” she said while looking me up and down.

Josephine jumped in without missing a beat. There was a glint in her eye that told me she was the most dangerous of the lot. “As you astutely noted, Liz,” she said with a devilish grin, “I believe he should parade about for us in nothing but his underwear.”

“Yes,” said Tatiana with a slow nod. “Let’s embarrass him properly. I imagine his poor sister was mortified when the wretch barged in on her during her bath.”

“Perhaps he could serve us tea while he is so exposed,” offered Charlotte sweetly. “I'm sure that would be quite embarrassing for the lad.” All the females tittered at the prospect. The more refined ladies covered their lips with dainty fingers as they giggled, a picture of aristocratic mischief.

For a fleeting moment, I seriously considered making a break for the door, punishment be damned. But both Becky and Brenda were stationed in a spot where they could provide interference, and I wouldn't put it past anyone in the room to give them a helping hand.

I have to at least TRY to talk my way out of this ghastly scenario.

“Please…everyone,” I began, trying not to sound like I was pleading—though I definitely was. “I said I was sorry. I truly didn’t mean any harm. It was supposed to be a harmless joke, but I realize now how wrong it was. I swear, it’ll never happen again.” I turned desperately to Becky. “Can we just go to the car now?”

“I don’t think so,” said Brenda’s mother icily. “You need to learn a lesson about consequences. And from this point forward, you are not to speak unless spoken to. Misbehaving children should be seen, not heard.” Off to the side, Becky and Brenda snickered.

“Now then,” Elizabeth continued smoothly, “we seem to be in agreement that the young miscreant should cavort about in his underwear for us."

“I propose we let him keep those darling girlish shoes and the frilly socks,” Charlotte chimed in with sparkling eyes.

“Oh, yes,” said Katarina. “They’re positively precious. And the added touch of femininity might turn up the heat on his embarrassment.”

“Splendid,” said Elizabeth with a clap of her hands. “Underpants, frilly socks, and Becky’s sweet little shoes it shall be. Now, let me ask you…how shall we handle the manner of his disrobing?”

For gosh sakes, I should have just stripped on the spot and gotten it over with. Brenda’s mother was clearly intent on prolonging the moment for theatrical effect—and, of course, for the fullest possible measure of my humiliation. Judging by the amused glances and barely concealed grins around the room, her audience was thoroughly entertained.

“We might have him perform a little striptease for us,” suggested Charlotte with a wicked grin. “A bit of music to set the mood, perhaps?”

Elizabeth’s eyes gleamed with mischief. “Oh, what a vision that would be. Most unbecoming for the lad—and perfectly delicious. So then, shall he disrobe himself?”

“Or I could do it,” Josephine offered, lifting one brow as a devilish smile curled at her lips.

Her friends burst into delighted laughter.

“Oh, Josephine, you wicked girl!” cackled Elizabeth. “That’s a marvelous idea. All in favor of letting Josie undress the young culprit, raise your hands.”

Gloved hands lifted gracefully into the air, every lady casting her affirmative vote. Becky and Brenda said nothing, but their smirks spoke volumes—they were quite content to watch events unfold.

“It’s unanimous,” Elizabeth declared with far too much cheer. “Josie, the honor is yours. Do proceed.”

A hush fell as every gaze locked onto me, heavy with delicious anticipation.

Josephine crooked a single finger in my direction. “Come,” she said with a sultry smile. “Let’s not keep the ladies waiting.”
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Roosevelt Humiliations: The Missing Chapters, Chapter 2

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Chapter 2: Punishment

With a profound sense of dread, I obediently shuffled forward, each step heavier than the last, until I stood trembling before Josephine like a schoolboy awaiting discipline.

“Gerlinde,” said Elizabeth, “do be so good as to stand by and accept each item of clothing from Josephine as she removes them.”

“Certainly, ma’am,” the maid replied. It was only two words, but I detected a European accent—almost certainly German.

She moved with quiet precision to Josephine’s side, folding her hands primly in front of her. I glanced at her and got the distinct impression that she was enjoying her duties at that moment—I'm guessing more than she ever had.

Josephine took my hands in hers and gently pulled me toward her. She offered a calm smile. “Do you have anything to say for yourself before I carry out your punishment?”

I shook my head. I knew there was nothing I could say to alter what was about to transpire.

“Very well then. I shall proceed.” She reached for the hem of my tee shirt and tugged it gently, loosening it from the waistband of my shorts.

“If you’d be kind enough to kneel, I would be most obliged,” she added with practiced politeness. “I prefer to conduct such matters seated—these knees of mine are no longer what they once were.”

So sorry about your knee pain. As long as you're comfortable, that's all that matters. Don't mind the fact that my dignity is hanging by a thread right now.

I knelt, awaiting my destiny. “Thank you, my child,” she said sweetly. “Now you’re in a perfect position to facilitate the removal of your top.” Her fingers found the hem again. “Arms up, if you please..."

I raised my hands above my head.

"Nice and high, like you're reaching for the sky.”

Resigned, I lifted my arms higher, stretching them to full extension.

"That's perfect. Now I can divest you of your top without any hindrance," she said while sliding the shirt up and off with careful ease.

"Excellent," she said.

The maid reached her hand out and Josephine handed her the shirt.

“Thank you, Gerlinde,” said Josephine.

“You’re quite welcome, ma’am,” she replied, folding the shirt precisely before resting it over her arm. She lingered nearby, poised for the next article of clothing, one which I was loath to part with.

“You may stand,” Josephine said. I rose, crossing my arms over my bare chest instinctively as a hush settled over the gathering. I was feeling my nakedness, and I felt all eyes on my newly exposed upper body.

“I do find his figure rather pleasing,” Charlotte remarked, eyes alight with amusement. “Thin, but not overly so.”

“Slender,” added Josephine.

“Lithe,” offered Tatiana.

“Slim,” Elizabeth added.

“Svelte,” chimed Charlotte again.

“Fragile is the word that comes to mind,” Katarina declared, receiving a chorus of approval.

“Yes, fragile! An exquisite choice, Kat!” Tatiana beamed.

I'm sure the reader has gathered that my having to listen to their back-and-forth observations was nothing less than excruciating for me. It was like I was their plaything, and they could say or do whatever they wanted. And their comments about me weren't exactly flattering for a 16-year-old boy who was eager to be more of a man; instead, I was being verbally reduced to something dainty. It most certainly exacerbated my humiliation, which, of course, is exactly what they had in mind.

“Thank you,” said Katarina with a modest smile. “I'm gratified that you agree. I must say, there’s a delicateness to him...smooth skin that is almost bereft of hair."

"Yes, there is definitely a paucity of hair," said Tatiana.

"Virtually hairless," Josephine nodded, appraising me clinically.

“A baldy,” snorted Charlotte.

“A real smoothie,” added Tatiana.

“He does lean toward the feminine, don’t you think?” asked Katarina.

“Soft,” commented Elizabeth.

“Silky,” Tatiana said, savoring the word.

“Tender,” concluded Josephine.

“Oh, look at his cheeks,” Katarina observed delightedly. “Absolutely scarlet. I do believe we’ve thoroughly embarrassed the poor dear.”

It was true. Just when I think my face can't get any hotter, it reaches another level.

And I'm about to lose my shorts!

"Oh my, you are so right, Tatiana," said Josephine. "I think we'd best suspend our teasing, lest the poor lad faints from embarrassment before we get our chance to undress him."

After a pause, Josephine looked up to me and gave me a command. “Now then. I’d like you to ask me—very politely—if I would be so kind as to remove your short pants. And you will address me as Miss Josephine.”

A ripple of approval moved through the seated ladies.

“Miss...Miss Josephine…would you remove my shorts...my short pants...for me?" I barely choked out the words.

Josephine raised an eyebrow. "Such manners. Were you not taught common courtesy, and how to use the word 'please?' Now try again. Only this time you can ask me if it would be acceptable to prance around in your underpants for our entertainment."

The maid could not suppress a snicker, and she was not alone.

“M-Miss Josephine...would you…may I…may I prance around in my underpants for your entertainment…please?”

Laughter rippled less cautiously now. My face felt like it was inside a furnace.

“It would be our pleasure,” Josephine answered smoothly.

The room was deathly quiet as Josephine drew me closer by the hips. I was now in a position where my shorts were easily accessible to a lady who was intent on separating them from my body.

She broke the silence as she deliberately worked on the button.

“I daresay this method of correction will prove quite effective,” she said conversationally as she popped the button. “Really, what better tools have we at our disposal for the improvement of unruly behavior than a touch of well-applied shame and a thoroughly red face?”

Everyone leaned forward slightly as she lowered the zipper in slow motion. The shorts clung stubbornly to my hips, but Josephine was undeterred. She grasped the hems and tugged, inch by inch, until the waistband of my white briefs was exposed.

She paused and leaned back. “Before we continue…I wonder what thoughts were dancing through your head when you decided to barge in on your sister in the bath like that?”

I didn't know what to say, as in all honesty not a lot of thought went into it, other than I thought it would be fun to piss off my sister—and to see her naked.

"Well, I...I...I really wasn't thinking...I guess."

“Clearly,” she replied dryly. “Think about it now, then. Put yourself in your sister's position. Suppose she and a friend of hers—say, Brenda—walked in on you while you were naked in the bath. Would you be embarrassed?"

“I guess.”

“You guess?” she echoed with mock indignation. “Are you embarrassed now?”

Of course I am, you bitch, and I'm becoming more and more embarrassed by this line of questioning. But that's what you have in mind, isn't it?

“Yes,” I whispered, staring at the carpet.

"Of course you are. Your cheeks are a dazzling shade of red."

She addressed her friends. "Ladies, I'd say the lad looks pretty embarrassed right now, does he not?"

“Indubitably,” said Charlotte.

“Positively mortified,” said Tatiana.

"Quite shamed, indeed," added Elizabeth.

"Abashed," said Charlotte.

“Humiliated,” concluded Katarina.

“Excellent,” Josephine smiled. “Then we’re on the right path.”

She turned to me. “Shall we continue?”

What am I supposed to say? If I say yes, she will take the shorts off. If I say no, I'll have to deal with more humiliating dialogue, then she will take the shorts off.

"Yes," I answered subserviently.

“Yes…what?”

“Yes, please.”

“Much better. Let’s proceed.”

Again she took the hems of my shorts on either side, but this time she didn't stop pulling on them until they reached my ankles.

“Step out of them, please.”

I did, and she plucked them up delicately, passing them to Gerlinde.

"Thank you, Gerlinde," she said.

"You're quite welcome, ma'am," she responded. The maid properly folded the shorts in half and laid them neatly over her arm with my previously discarded shirt.

I stood with my shoulders slumped and my hands crossed over the front of my underpants. I was embarrassed as all get-out.

“I do declare,” said Tatiana. "We have managed to embarrass him to the nth degree."

“Indeed,” said Charlotte. “Look at that body language—defensive, self-conscious.”

“Crimson cheeks,” Elizabeth noted.

“Positively glowing,” said Katarina.

“Well,” said Josephine with a satisfied sigh, “our dear boy stands here stripped to his underpants against his will, a flock of ladies gazing upon him. It's no wonder he is so embarrassed. I do declare, I can't imagine what it would feel like to be in his predicament."

"Unimaginable, indeed," said Charlotte.

“Unfathomable,” added Tatiana.

“Unthinkable,” said Elizabeth.

“Incomprehensible,” Charlotte finished.

“And I daresay,” Tatiana drawled, “his choice of underpants adds to the spectacle.”

“Indeed,” said Josephine. "My son wore white briefs like these during his childhood. He said he felt like a baby in them. I let him graduate into something more sophisticated in lieu of his childish underwear. I believe he was eleven at the time."

From somewhere behind me, I heard Becky and Brenda giggle. I looked up at the maid and detected a smirk on her face. Everyone in the room was thoroughly enjoying my descent into wretched embarrassment.

And the worst was yet to come.
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Roosevelt Humiliations: The Missing Chapters, Chapter 3

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Chapter 3: Servitude

“I find it rather fascinating,” said Katarina, cocking her head thoughtfully, “that he insists on keeping his hands over his private parts.”

“Yes, quite,” agreed Tatiana. “I mean, it would make sense if he weren’t wearing underpants, but…”

“I think—oh, forgive me, Tatiana,” interjected Josephine. “How terribly rude of me to interrupt. Please, finish your thought.”

“Oh no, not at all,” Tatiana replied graciously. “I’d much rather hear what you were going to say.”

“Well,” said Josephine, lowering her voice slightly, “I was only going to observe that he is indeed wearing…shall we say, snug little boyish underpants. The kind that would certainly reveal a—shall we call it—protuberance, were there one to see.”

“Ahh, I see where you are going with this, said Tatiana, nodding. “You’re suggesting he’s a bit bashful about letting us examine his...protuberance.”

“Exactly,” said Josephine. “And I dare say it’s entirely plausible—especially given how slender and delicate he is—that he’s more than a little embarrassed by its…lack of prominence.”

“I do believe you’re quite right, Josie,” said Elizabeth, her lips curving into a sly smile. “Having taken in the full measure of our little guest—as I’m sure we’ve all done multiple times—it’s hard to imagine he’s blessed with...let's see, how shall I phrase this...anything particularly formidable in the realm of his endowments."

A ripple of delighted tittering passed among the elegantly dressed ladies. One touched her fan to her lips as she giggled.

“Well said, Liz,” Charlotte added cheerfully. “In fact, I should imagine the reality may lean rather in the other direction.”

“Hence the hands,” said Tatiana.

"Because he is too shy—or too embarrassed, to be more accurate—to display the front of his boyish underpants," said Josephine.

“Precisely,” said Charlotte. “Why else would he stand like that unless he had something—”

“Or nothing—to hide,” Katarina cut in with a grin.

“Well played,” said Elizabeth, as the ladies burst into delighted laughter.

“I must say, though,” said Charlotte, “that pose is unbecoming. Perhaps we should give him something useful to do with those hands. Tea service, perhaps?”

“Capital idea,” said Elizabeth. “Young man, if you please—my guests are all in need of a refill. You’ll find the teapot behind you, along with the necessary accoutrements.”

I turned to see the silver teapot gleaming on the coffee table behind me, flanked by a set of delicate china cups and saucers, each adorned with its own dainty spoon.

“Gerlinde,” Elizabeth continued, “Would you be a dear and demonstrate for the lad how to properly serve tea? You can serve Josephine first, and then he can take over.”

“Of course, ma’am,” said Gerlinde, sounding far too eager for my comfort.

"Young man,” Elizabeth turned to me, her voice sharpening slightly, “I expect you to observe Gerlinde’s every move carefully. You are to replicate her actions precisely.”

Now in full-fledged anxiety mode, I watched Gerlinde, who now had a white towel draped over her arm instead of my shirt and shorts. A quick survey of the room did not satisfy my hope of spotting my clothes.

Gerlinde gently nudged me to the side so she could address Josephine. “How do you take your tea, ma’am?”

I suspected she already knew—this was clearly a performance for my benefit.

“No milk or sweetener, dear,” said Josephine.

Gerlinde poured the tea with elegant precision, handed it over with a polite curtsy, and received a gracious “Thank you” in return.

“You’re welcome, ma’am,” she replied, then turned to me.

She held out the towel expectantly. I didn’t move. I wasn’t ready. The prospect of serving tea to these ladies in my underpants seemed to have rendered me temporarily paralyzed.

With quiet insistence, Gerlinde took my left wrist and lifted it, draping the towel over my arm. My right hand stayed pressed to my groin like it had been superglued there.

“If any guests request milk or sweetener,” instructed Gerlinde, “the proper order is: milk first, sugar after the pour. One teaspoon, unless otherwise requested.”

Gerlinde stepped aside, gesturing with her palm for me to proceed.

Oh, shit, I guess I'm really doing this!

I moved to the coffee table, hesitated, then picked up the teapot with my right hand. Eight sets of eyes immediately zeroed in on my crotch.

For me, the best course of action was to get the fucking tea poured as quickly as possible. I picked up Katarina’s cup and saucer.

“How do you take your tea, ma’am?” I asked, my voice a bit higher than usual.

“A spot of milk, please,” she replied.

I identified the milk container, set the teapot down awkwardly, bent over to fetch a teaspoon—and heard the tittering behind me intensify.

Becky and Brenda were openly giggling now. I flushed hot as I poured the tea and handed it to Katarina.

“Thank you, dear,” she said with exaggerated sweetness.

“You’re welcome…ma’am,” I stammered.

I moved on to the next guest and picked up Tatiana's cup and saucer. "How do you take your tea, ma'am?"

And so it went, until they each had a full cup of tea, and I was thoroughly mortified.

By the time I’d finished, I didn’t know where to stand—or where not to stand. I edged toward the next room, but Gerlinde gently tugged me back into the middle of the parlor.

“You must remain at the ready,” she said, adjusting the towel on my arm. Then she took my right hand and placed it firmly at the small of my back, nudging my shoulders upright.

“Stand up straight,” she instructed softly, before slithering off to the side of the room, leaving me to fend for myself.

All the ladies stared at me, smiling. It was uncomfortably silent for what felt like forever before Katarina spoke up. In retrospect I think I would have preferred the silence.

“I must say,” Katarina finally broke it, “he really is a delectable sight—standing there subserviently, nearly naked, and blushing so prettily.”

“Indeed,” said Elizabeth. “That fair hair against those rosy cheeks…so lovely.”

“Exquisite,” offered Charlotte.

“Enchanting,” added Tatiana.

“Delicious,” purred Josephine, licking her lips.

“I do find his legs rather fetching,” Tatiana remarked with an appraising glance.

“Oh, yes,” agreed Katarina with a sly smile. “They’re quite dainty, really. So slim and smooth…not a trace of hair, and not a hint of manliness about them. More befitting a debutante than a boy.”

“They're so nice and slender,” Charlotte observed, still grinning over Katarina's remarks. “They have that graceful line you usually only see in girls.”

“And really not much muscle definition,” said Katarina. “Just smooth skin and soft curves.”

Enough about my legs! Jeez!

"If I had legs like that, I’d never wear pants again,” Josephine teased, drawing giggles from the ladies.

“Indeed,” Katarina added, smiling. “Smooth, shapely, and just enough curve in the calf to seem…ladylike.”

“Surprisingly delicate,” Tatiana observed. “Gracefully long, slender throughout, and tapering quite perfectly at the ankle. So pretty.”

“They're are almost too pretty,” Elizabeth said. “They could belong to a figure skater—or a fashion model.”

“Feminine,” said Charlotte.

"Attractive," said Tatiana.

“Lovely,” said Elizabeth.

“Charming,” said Josephine.

“There really isn’t much hair anywhere below the neck,” Katarina observed again.

What's with this Katarina lady and the hair obsession? Stop it!

"That's true," said Tatiana. "I do find it captivating."

“I wonder,” mused Katarina, “has he even started growing underarm hair?”

Oh, for fuck's sake!

“I did get a glimpse,” Josephine offered. “When I took off his shirt, he clamped his arms down quickly, but I can't say that I saw any hair in that split second."

"I do wonder," said Charlotte.

“I’m curious too,” said Katarina.

“As am I,” said Tatiana.

“Inquiring minds, as they say…” Katarina said.

“There is, of course, a very simple way to find out,” said Elizabeth. “Gerlinde, would you kindly position our young lad so we may observe his underarms?”

Why don't they just ask me? I don't want to do this, but I really don't like the maid being involved. She seems to be enjoying herself way too much.

“Gladly, ma’am,” said Gerlinde, with a hint of glee.

She took the towel from my arm, stepped behind me, and gently but firmly lifted my wrists up behind my head, locking my fingers together. Then she pulled my elbows back until they were parallel behind my head.

She leaned forward to peek at my underarms before sauntering off a few steps to the side with a pleased smile.

“Thank you, Gerlinde,” said Elizabeth. "This is perfect."

“My pleasure, ma’am,” she replied.

Yeah, I'm sure it was. Schadenfreude, anyone?

And sure enough, to the absolute delight of my audience, my underarms were completely hairless. I had finally started puberty (about fucking time!), and had started growing pubic hair, but so far not much else.

I prepared myself for having to suffer through more of their repartee, and true to form, they started right in.

“A delightful presentation,” said Tatiana.

"Yes, a lovely display," added Charlotte, lifting her teacup with a satisfied smile.

“I believe that settles the matter quite conclusively,” Katarina said, her eyes gleaming. “His underarms are smooth as silk. Devoid of even the faintest suggestion of masculinity.”

“I must say,” Elizabeth noted, “his innocence, his blushes…his virginal skin...it’s all quite delightful to behold.”

“Mmm, yes,” Josephine purred. “Tall, slender, skin like porcelain—and that expression! So embarrassed, so sweet. So delicious. He’s like a little strawberry sundae, and that blush is the cherry on top.”

"I simply must have a picture of this," declared Katarina, pulling out her phone. “You don’t mind, do you, Liz?”

“Not at all. And do share it with the group, won’t you?”

“Of course, I'll be happy to. This should be a darling photograph,” said Katarina as she carefully framed the shot. She snapped a photo of an utterly mortified sixteen-year-old boy—red-faced, smooth-skinned, standing in nothing but his underpants, frilly ankle socks, and girlish tennis shoes—his posture a portrait of humiliation. “Perfect!” she beamed.

“Did you get a close-up of his underpants?” asked Tatiana. “I’m still not sure what he was trying to hide earlier.”

"I didn't get a close-up," answered Katarina. "But we can always enlarge the picture with our fingers and zoom in. I do see what you mean, though, Tatiana. I don't see much there with the naked eye."

"I don't either," said Charlotte.

Then Tatiana tilted her head. “This might be a silly question, but…are we certain he’s a boy?”

There was a soft gasp that emanated from one of the ladies, followed by a hush as they continued to size me up. I could feel their eyes traveling down my body, landing on my underpants as if to obtain an answer from the barely-there bulge.

I glanced down at my underpants, and, though it wasn’t anything to brag about, there was enough there to leave no doubt as to my gender.

Still, that wasn't going to stop them.

"Hmm, one does wonder," answered Charlotte. "He does have some feminine features."

“Such a deliciously provocative question, Tatiana,” said Josephine. “So what you’re proposing is that he—or ‘she,’ as the case may be—is a girl masquerading as a boy?”

“Well, yes and no,” Tatiana replied thoughtfully. “He’s got a boy’s haircut, sure—but his socks and shoes are clearly feminine. So maybe it’s the other way around? A boy pretending to be a girl pretending to be a boy? Honestly, it’s a riddle.”

“An intriguing perplexity indeed,” added Katarina.

“Quite,” said Charlotte, leaning in to inspect me further.

Oh, fuck me, I see where they might be going with this.

“Or perhaps,” offered Elizabeth, “he isn’t pretending at all. Perhaps he is, in fact, a boy—but one who’s been put in feminine attire against his will as a form of retaliation. A well-earned punishment for a vile transgression against his sister.”

Oh, thank you for that. Can we please just stop here and let that be the end of it?

"That is certainly a possibility," persisted Josephine. “But I, for one, feel we’d be remiss if we left today without being entirely certain of this young person’s gender.”

Oh, fuck me again!

Katarina’s gaze dropped to my underpants, her eyes twinkling. “Oh Josephine,” she said, giggling. “Are you thinking what I think you’re thinking, you devil, you?"

“I daresay I am,” Josephine giggled back.

“Great minds,” Charlotte added with a mischievous grin.

“And devious ones,” chimed in Katarina.

“It does seem like the most efficient way forward,” said Tatiana, now openly staring at my crotch. “After all, the proof is in the pudding.”

“It appears we’re in agreement,” declared Katarina. “Now then—does anyone have a proposal as to how we should…conduct the unveiling?”

“There are options,” Tatiana mused. “He could, upon request, simply lower his underwear for us while we inspect the evidence.”

"Or I could do it," said Josephine, echoing her earlier offer—though this time, the reaction from the others was far more enthusiastic.

“Yes!” Tatiana exclaimed. “Josephine is the perfect candidate for the task.”

And just like before, Josephine turned to me, crooked her finger, and said a single word. “Come.”

And just like before, I obediently walked over and stepped in front of her, only this time with an even bigger sense of trepidation.

The room held its breath.

“Déjà vu, wouldn’t you say?” she said with a sly smile. I said nothing.

“But this time,” she added, eyes sparkling, “there’s quite a bit more on the line, wouldn’t you agree?”

Still silent, I stood frozen as she slid her fingers inside the waistband of my underpants. A full-body shiver ran through me. My heart pounded as I clenched my eyes shut, bracing for the imminent humiliation.

She began pulling downward.

“Wait!” came Elizabeth’s sharp voice.

Josephine froze, surprised by the interruption, but still holding onto my waistband. She glanced up at Elizabeth.

“I hate to be a killjoy,” said Elizabeth, “but I'm wondering if we might possibly be taking this a bit too far."

Finally, someone shows a hint of human decency. The debauchery ends here? Oh, please!

“Let’s be honest,” she continued. “Our intention was to embarrass the lad, to ensure he understands the severity of what he did to his sister. And judging by the hue of his cheeks, I think we’ve achieved that goal quite thoroughly. My gosh, I've never seen anyone blush so brightly and for so long in my entire being." She turned her attention to me. “Look at me, young man.”

She was behind me, and Josephine still had a firm grip on my underpants, so I was hesitant to turn around.

Could you let go of my underpants? Give it up, would ya'? You heard the lady of the house.

I turned my head as best I could. Josephine stubbornly maintained her grip, and I swore I felt my underpants slip just a little lower.

Please! Someone make her stop!

“Have you learned your lesson?” Elizabeth asked.

“Yes, ma’am,” I said instantly. “I promise.”

“Very well. I believe it’s time you got dressed, and you and the girls can be on your way.”

I had a feeling that the level of disappointment among the rest of the females in the room was only matched by the level of my sense of relief.

“Gerlinde,” Elizabeth continued, “Would you be so kind as to fetch Blondie’s clothes?”

“Yes, ma’am,” Gerlinde replied, turning toward the hallway. But before she could get far, she was intercepted.

“Gerlinde,” said Brenda, speaking for the first time since we’d entered the room. “Would you mind holding off for just a moment?"

Gerlinde stopped mid-step and turned with a curious look.

“Mother,” said Brenda, “There’s something I need to tell you. It’s about Blondie.”

What the fuck? Oh, no. What is she up to? Whatever it is, this can't be good.
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Roosevelt Humiliations: The Missing Chapters, Chapter 4

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Chapter 4: Disciplined

Elizabeth looked at me with a furrowed brow, then at her daughter. "What is it, dear?"

Brenda hesitated just long enough to send a chill through me. “Well…it’s something he did to me a while back. At school. I probably should have told you then, but it was a bit embarrassing...”

Oh, shit. I think I know where this is going. Oh, shit!

Elizabeth leaned forward slightly. “It’s all right, Brenda. You can tell me. Would you prefer to speak in private?”

“No, it’s okay, Mother. I’m over it now. But I think it’s time you knew what he did.”

Oh. Shit.

Elizabeth took another look at me—a stern one—then looked back at Brenda. "Okay, dear—please, get it off your chest."

That was an interesting choice of words, as the reader will soon see.

Brenda gave a rueful little smile. “One morning I walked into homeroom, and...he’d written something on the chalkboard. It was...he was trying to embarrass me, and I have to say that he was successful. Everybody was looking at me when I walked in, then I looked at the board."

Elizabeth’s face darkened. “What exactly did he write?”

Uh-oh.

"Well, in deference to your guests," said Brenda as she gestured toward the enraptured foursome with an open palm, “I won’t quote it verbatim. Let’s just say…it was vulgar. A crude comment about the size of my chest.”

There were gasps from the women. Josephine, who had been idly toying with the waistband of my underpants, let go in surprise.

Elizabeth remained silent for an extended time, but I could almost see the blood rising to her head as she contemplated Brenda's disclosure.

Then, suddenly, it was like she lost control, such was her state of fury. I know she was upset that I had made fun of her daughter, but man, she was really pissed. In retrospect, I'm thinking I struck a nerve, maybe because she shared a similar physical characteristic with Brenda, that of a less than average-sized chest.

Whatever the reason, I would suffer the consequences of her wrath. In spades.

"That does it! How dare you embarrass my daughter like that in front of her classmates!” she exploded. “You shameless little wretch! I know just how to deal with naughty boys like you.”

She turned sharply. “Gerlinde, would you fetch one of the dining room chairs, please? One without arms.”

“Certainly, ma’am,” said Gerlinde, already moving.

She returned with military efficiency, carrying a straight-backed chair with a red cushion. She set it down dead center in the room.

I think the sudden turn of events must have thrown my brain for a loop, because I'm pretty sure I was the last one in the room to comprehend the purpose of the chair. But I finally realized that if things transpired as I suddenly suspected, then eventually I would have my own built-in red cushion—and a painful one at that.

Elizabeth sat down and smoothed her skirt. She looked up at me with fire in her eyes.

“You get over here right now, young man!”

Oh, this would be way too humiliating. I just can't let it happen.

My eyes darted to the hallway—an open path. I took off running.

But I didn't get very far. I don't even know where the hell I thought I would go. After all, I was clad in a pair of underpants, and I had no idea where my clothes were. I just knew I had to get out of there and somehow avoid being spanked like a child in front of eight females, all of whom were probably licking their chops at the prospect.

I also had no inkling that the maid's quickness, agility, and strength were far superior to my own.

She caught me from behind, wrapped her arms around me and lifted me in the air like a rag doll. For a fleeting second I envisioned her younger, as a German athlete on steroids.

I wasn't going down quietly. I kicked my legs wildly as she started walking me over to Brenda's mother. I was kicking up a storm and I know I managed to kick her in the shins a couple of times. I don't think she appreciated it.

“Ma’am,” she said calmly, still holding me with zero effort, “may I remove his shoes? I don't want him to hurt you if he happens to kick you while he struggles."

"Certainly, Gerlinde. By all means, please do. Would you like some help?"

"No thank you, ma'am. I can manage him."

And man, could she.

There’s probably a proper wrestling term for the hold she locked me into—but I haven’t the faintest idea what it is. What I did know was that she was perched on the small of my back, and I was going nowhere. Every attempt to break free sent a sharp jolt of pain through my body.

"Get the fuck off of me!" I screamed. The outburst of profanity elicited gasps of shock and dismay from the guests.

"You'll suffer consequences for that with a separate punishment," admonished Elizabeth.

Meanwhile, Gerlinde went to work on my shoes. She knew I was defenseless, so she made the effort to untie them instead of just yanking them off. She then pulled them off and placed them neatly side by side next to us.

"You might as well remove his socks while you're at it," Elizabeth added. “He’ll receive his punishment in just his underpants.”

Why? I'm glad to lose these fucking socks, but....

“Yes, ma’am.”

She effortlessly removed the socks and diligently placed them inside the shoes. I felt the cool air on my bare feet.

Oh, now I see. It feels more naked. I'm sure it LOOKS that way, too.

I don't know how Gerlinde did it, because I was fighting her tooth and nail, but the next thing I knew I was lying face down on Brenda's mother's lap. Gerlinde had a firm grip on my biceps, and try as I might I was unable to extricate myself from her grasp. For good measure, Becky and Brenda had each taken hold of one of my ankles to keep me from kicking my legs.

I braced myself for the first smack. But there was something Elizabeth felt the need to do before beginning her onslaught. I should have seen it coming, but I was completely caught off guard when I felt her fingers slip inside the waistband of my underpants.

Oh no, not on my bare ass! Not in front of these ladies. I'm way too old for this!

"No!" I screamed. "Please don't!"

Of course, my pleas were ignored. With one quick tug, my underpants were yanked down to my thighs, leaving my quivering cheeks completely exposed.

"No!" I cried again, mortified.

But the only reply was the sharp smack of a hand against bare skin. Then another. And another. And another. I lost count. They came in quick, relentless succession.

"Ow! No! Please stop!" I begged.

I glanced back and noticed she’d switched to her left hand—her right must have started to hurt. The change made no difference; each smack still landed with a sharp sting, her blows peppering my backside with unyielding precision.

"Oh! No more! Please!" I begged. I had tears in my eyes, as the pain was really registering.

"I think you all can let go," said Elizabeth. "I don't think he'll be putting up much of a fight anymore."

She was right. I had been spanked into submission. Gerlinde and the girls released my arms and legs, but I compliantly remained on Elizabeth's lap.

For good measure she slapped me a few more times while I clenched my eyes shut and held onto the legs of the chair.

"Oh! Oh! Oh God, please, no more!"

Finally, she relented. "You can get up now," she said.

I pondered my next move. Even though it felt like someone was holding a torch to my ass, my main concern was that my underpants had been pulled halfway down my thighs. My priority was to pull them back up without anyone catching a glimpse of my privates. I slid off her lap and quickly put one hand over my crotch while simultaneously reaching for my underpants with the other.

"Leave those right where they are," commanded Elizabeth, quite authoritatively.

I froze, then slowly pulled my hand away and covered myself with both hands. “Awkward” doesn’t even begin to describe my situation—I had no idea what to do or where to go.

Brenda's mother took care of that. “You can go stand in the corner for a bit and reflect on your behavior.”

Just like a 6-year-old boy. Oh, the shame.

She pointed to a spot a few feet away, squarely in view of everyone. With a pitiful waddle, I made my way to the corner, walking bowlegged to keep my underpants from slipping any lower.

Once I reached my destination, I pressed my nose into the wall. Relieved that my privates were hidden from view, I placed the backs of my hands over each butt cheek.

Apparently, that wasn’t allowed.

“Put your hands by your sides and keep them there,” Elizabeth ordered.

I obeyed. My red-hot backside was now fully on display.

“Gerlinde,” said Elizabeth sweetly, “would you be a dear and fetch a fresh bar of soap from the cabinet?”

“Will do, ma’am,” Gerlinde replied.

While Gerlinde walked out my mind raced, trying to figure out what the bar of soap was for, and was hoping beyond hope that it didn't involve me.

What, is she going to give me a fucking bath?

Efficient as always, Gerlinde returned promptly, carrying a pink, oval-shaped bar of soap.

“Thank you, Gerlinde,” said Elizabeth. “You may insert it into the naughty boy’s mouth. Perhaps his memory of the aftertaste will give him cause for pause next time he considers using such filthy language."

“Indeed, ma’am,” Gerlinde said with quiet satisfaction.

As she approached, I instinctively covered my crotch. She held the soap near my lips.

“Open,” she said.

The scent was flowery and deceptively pleasant. I kept my mouth shut and leaned away, but she pressed the bar firmly against my lips.

“Open,” she said again—firmer this time.

Of course, she would win, regardless of how hard I might try to avoid it. I parted my lips, and she pushed the bar in until it hit my soft palate. Only an inch or so stuck out.

“Bite down with your teeth so it doesn’t slip out,” she instructed.

Before walking away, she gently guided my head back into the corner and used her hands to pull my arms to my sides again.

In case the reader has never had the pleasure of tasting soap, let me help you out—DON'T! It's horrible! I've never tasted anything so bitter in my life, and hope to hell I never do again.

Meanwhile, I was about to be subjected to another volley of stinging commentary from the ladies.

“Elizabeth,” said Katarina, “I must commend you on the spanking. You did a marvelous job warming his behind.”

“Thank you,” Elizabeth replied with a demure smile. “He gave me plenty of motivation.”

“His derriere is quite a magnificent shade of red,” remarked Josephine, leaning forward for a better look.

“Yes,” Tatiana agreed. “It’s almost glowing.”

“I’m simply thrilled you did it on the bare,” said Charlotte, smiling over the rim of her teacup.

“Much more embarrassing for him that way,” Josephine added with a knowing nod.

“He definitely deserved it,” said Tatiana.

“I have to admit,” said Katarina, her smile turning wicked, “I found the whole scene...rather titillating.”

Pervert.

“I know what you mean,” Tatiana said with a throaty laugh.

“I think Elizabeth really caught him off guard when she yanked down his little underpants,” Charlotte chimed in. “‘No! Please don't!’" she mimicked. "I found that part rather stimulating."

“I noticed how his little tush gave a twitch the moment it was bared,” said Josephine.

“Delightful,” Charlotte echoed, eyes gleaming.

“Provocative,” purred Katarina.

“Delicious,” added Josephine with a wink.

“Utterly scrumptious,” cooed Tatiana.

Perverts. Every last one of them.

“He really does have a cute little bottom,” Charlotte said.

“Quite captivating,” agreed Tatiana.

“Oh! Did you see that?” said Katarina. “Another twitch! We must be embarrassing him.”

You think?

“There it goes again!” Josephine giggled. “Every time he squeezes his cheeks together!”

"Silly boy," said Katarina. "I think it's a defensive reaction, but it only serves to tickle our fancy."

“It tickles our fancy when he twitches his fanny,” Josephine quipped with glee, setting off another burst of laughter.

“Gerlinde,” said Elizabeth, still laughing, “I believe you may remove the soap now. We don’t want the poor dear to ingest too much. I think he’s gotten the message. I highly doubt that we'll be hearing any more ugly profanity spewing from his mouth.”

“Yes, ma’am.”

“Oh, and Gerlinde…” Elizabeth leaned in to whisper something. I couldn’t make it out, but I heard Gerlinde chuckle softly.

“Yes, ma’am,” she said, and began walking toward me.

I covered myself reflexively as she gently pulled the soap from my mouth. As awful as the experience had been, I was genuinely grateful to have that vile thing gone. I swear I had the bitter taste in my mouth for a week.

I was exponentially less grateful for her next maneuver. To my horror, I felt my underpants being whisked down to my ankles.

What the...no!

Just as swiftly, my legs were pulled up one at a time and my underpants were slipped off my feet. Efficient as always, she had me disrobed in less than five seconds.

Oh, my God! I'm naked!

“He’s naked,” Katarina observed gleefully.

“Nude,” said Elizabeth, deadpan.

“Au naturel,” sang Josephine.

“In the buff,” added Charlotte.

“Exposed,” said Katarina, relishing the word.

“Vulnerable,” offered Charlotte.

“Helpless,” added Josephine.

“Shamed,” said Elizabeth.

“Oh yes,” agreed Tatiana. “Positively mortified.”

“Humiliated, I’d say,” said Katarina.

“It’ll be a long time before he gets over this,” said Charlotte.

"What nightmares are made of," said Josephine with relish.

A living nightmare," Charlotte agreed, eyes dancing

“And yet, I get the distinct sense it’s not quite over," said Katarina ominously.

“He must be wondering, ‘What’s next?’” Tatiana mused.

“I do believe there is potential for more,” Katarina noted with a gleam in her eye.

“Indeed,” said Josephine. "There is definitely still room for escalation."

“Right—more before we close the book,” said Charlotte.

These ladies are fucking nuts! Get me out of here!

There was silence for a long spell (thank you!), until Gerlinde cleared her throat gently.

“Ma’am, if you please?” she said.

“Yes, Gerlinde?” Elizabeth turned, already intrigued.

“There are some mini crumpets prepared in the kitchen, ma’am. I’m quite ready to serve them. However...” She let the word hang momentarily. “...perhaps the lad might do the honors instead? I suspect your guests would be most entertained. And it would, of course, be a fitting continuation of his correction—serving you all, as he is, in his current state of...undress. But of course, that’s only if you believe he could benefit from...an extra helping of embarrassment."

Elizabeth’s eyes lit up. “Why, Gerlinde... that’s a wonderful idea.”

No. No it isn't. It's a terrible idea! In fact, it is probably the worst idea any human has ever come up with in the history of mankind. Ohhhhhh.....

"Why don't you take him with you into the kitchen," Elizabeth instructed, "and teach him how to properly serve our guests,"

“Yes, ma’am.” Gerlinde took my elbow and led me toward the kitchen while I frantically covered myself with both hands.

“Oh, and Gerlinde,” Elizabeth called after us, “when he returns, I expect that filthy habit of his—touching himself in public—will be thoroughly corrected.”

“Indeed, ma’am,” Gerlinde said, just as the kitchen doors closed behind us.
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Roosevelt Humiliations: The Missing Chapters, Chapter 5

Post by Blondie »

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Chapter 5: Crumpets

Gerlinde walked me through the large kitchen and brought me to a stop in front of one of the sinks.

"Wash your hands," she ordered.

With my back to her, I finally allowed myself to remove my hands from covering myself. I turned on the water and reached for the bar of soap. I was pretty sure it was the same bar of soap that she had removed from my mouth a few minutes before.

"From this point forward," she said firmly, "you are not to have your hands anywhere near your privates."

Oh God, this is going to be torture.

I finished washing, dried my hands, and stood still, facing the sink with my back to the devilish maid.

"Turn around. Let's have a look," she said.

A look? Have a LOOK? What we have here is another pervert.

I turned slowly, forcing myself not to cover up. Gerlinde’s eyes dropped immediately to my crotch, her smirk widening with no attempt to hide it.

"Poor boy," she said. "The ladies are going to have such fun with you out there."

She turned back to the counter and began arranging finger foods on a silver tray. I assumed these were the “mini crumpets” she had mentioned earlier—tiny rounds, each pierced by a dainty toothpick.

I instinctively turned away again, but that didn’t sit well.

"Face me," she snapped. I obeyed. "Now put your hands behind your head, elbows out. Feet together. Stand tall."

I hesitated, but complied. The pose made me feel very naked and vulnerable.

"We will call this the submissive position. Whenever I tell you to assume the submissive position, you will stand exactly as you are now. Do you understand?"

I nodded.

"What is this position called?" she asked, eyeing me up and down.

"The submissive position," I answered meekly.

"Good. You will remain in this position until you are told otherwise. Miss Elizabeth has instructed me to train you properly, and I take that responsibility seriously. It is a reflection on me if you are not properly trained, and I will not have you tarnish my standing with the lady of the house. Do you understand?"

Again I nodded.

"'Yes, ma'am' would be your proper response."

"Yes, ma'am," I replied.

"Excellent. And should you defy me," she added, picking up a wooden spoon for emphasis, "I will not hesitate to take you over my knee for another thrashing. And believe me, you do not want to be on the receiving end of a thrashing from me if I become angry."

I had no doubt as to the veracity of that statement.

"Now, let’s get you ready to serve. The guests are waiting." She held up the tray for me to examine. "As you can see, there are two varieties. You will be asked about the ingredients, so listen closely. On the left: butter pecan with apricot preserves. On the right: smoked salmon blended with cream cheese and quartered cucumber slices. Got it?"

"I...I think so."

"Okay, what kind of crumpets are these?" she asked while pointing to the ones on the left.

What the fuck? I have to stand here naked and recite hors d’oeuvres ingredients in this so-called ‘submissive position’?

"Uh...pecan with apricot?"

"It’s butter pecan with apricot preserves. Try again."

"Butter pecan with apricot preserves."

"And these?"

"Salmon with cheese and...cucumbers?"

SMACK! The wooden spoon landed squarely on my already tender backside.

"Ow! Oh!" I said as the pain hit home.

"They are smoked salmon blended with cream cheese and quartered cucumber slices. Say it."

"They are smoked salmon blended with cream cheese and quartered cucumber slices," I groaned, shifting my hips from the sting.

"Good. You best not forget—lest you’d like another reminder."

I best not! Fuck! Butter pecan with apricot preserves, smoked salmon blended with cream cheese and quartered cucumber slices. Butter pecan with apricot preserves, smoked salmon blended with cream cheese and quartered cucumber slices. Fuck!

"When you serve, you will ask: ‘May I interest you in a mini crumpet, ma’am?’ Say it."

"May I interest you in a mini crumpet, ma’am?"

"Excellent," she said. "And hand them one of these napkins as they accept. Also—you are never to let this tray shield their view from your little privates. I know the ladies will be eager to look them over."

Of course they will. They're perverts.

She handed me the tray, then held out an open palm, indicating for me to lead the way.

"It's time," she said.

I took a deep breath and began walking toward the living room. It felt like a death march.

I didn’t get far before Gerlinde stopped me. "Wait," she said.

I stopped, and she stepped in front of me. She had taken off her maid's mob cap and was holding it in her hands. Without a word she reached up and placed it around my head, then carefully arranged it to her liking, like someone dressing a doll.

She stepped back and looked me up and down, her gaze lingering with amusement. Then she gave a satisfied little nod before stepping aside, clearly pleased with her handiwork.

"Proceed," she said. "And hold the tray out to the side."

I continued walking, and along the way, I was greeted by my reflection in a decorative, full-length mirror. Tray in hand, maid’s cap perched on my head, and completely nude—I saw myself as they soon would, and the weight of it sent a wave of dread crashing through me. There was no masking how I looked—just a naked and humiliated boy on display.

Oh God. Oh God. Ohhhhh.

As I stepped into the living room, a chorus of delighted gasps and amused laughter greeted me.

"Oh, my!" someone exclaimed.

Becky and Brenda were doubled over with laughter. The other ladies were grinning with open delight.

Trying to stay composed, I walked straight to Josephine.

"May I interest you in a mini crumpet, ma’am?" I asked.

Of course, she was looking past the tray of crumpets and straight at my privates. "Why, these look delectable," she said, still staring at me instead of the food. She finally gestured toward the left side of the tray. "And what have we here?"

"They are butter pecan with apricot preserves," I said, voice cracking.

She took one, and I handed her a napkin.

"Thank you, dear. They’re so cute and petite," she added, casting another glance downward.

I took a deep breath and turned to Katarina.

"May I interest you in a mini crumpet, ma’am?"

"Why, I’d be delighted," she said, her gaze already dipping below the tray. She plucked one delicately with her fingertips and arched an eyebrow. "And what is this charming little morsel called?"

"Smoked salmon blended with cream cheese and quartered cucumber slices," I said, trying to sound composed.

I glanced over at Gerlinde, who was smiling approvingly.

This is humiliating as all hell, but at least I'm not going to experience the wide end of the fucking wooden spoon.

"Mmm, lovely," Katarina said—but her attention was clearly not on the food. She took a dainty bite, then added with a wicked smile, "Though I must confess, I’m far more intrigued by the other little delicacies you’ve brought to the party."

She paused just long enough for a few of the ladies to titter behind their teacups.

“Presentation is everything,” she continued. “And yours is just precious. Such delicate offerings...so small, so sweet.”

She dabbed her lips with the napkin I’d handed her, then—with a twinkle in her eye and another slow, deliberate glance downward, she added, "Between the crumpet and the server, I’m not sure which is the more adorably undersized.”

A ripple of amusement passed through the circle. Fans fluttered, gloved hands rose to smother grins, and a few of the ladies let out barely restrained titters. I stood there, cheeks burning, my humiliation deepening with every dainty giggle and lingering glance

"Gerlinde," Elizabeth called out as I approached the next guest. "I must commend you on a superb job you did of training the lad."

"Hear, hear," added Charlotte.

"Thank you, ma’am," Gerlinde replied.

"And the cap was a brilliant touch," Elizabeth continued.

"Indeed," said Tatiana, smiling devilishly at me as she took a crumpet.

"Yes," said Josephine, eyeing me carefully. "The cap is a nice feminine touch to compliment his somewhat feminine features."

"Quite delightful indeed," said Charlotte as she also sampled a crumpet.

"I think he makes a lovely maid," said Tatiana.

"A lovely naked maid," added Katarina, earning a round of chuckles.

"Especially a reluctant naked maid," said Charlotte.

"I must say," laughed Josephine. "To be served and entertained simultaneously—what a delightful little indulgence."

I moved in front of Elizabeth, and it was momentarily quiet, so I felt obligated to repeat my compulsory line. "May I interest you in a mini crumpet, ma'am?"

"Thank you, I don’t mind if I do," she said, plucking one from the tray. Then she gestured toward Becky and Brenda, who were standing off to the side. "And don’t forget to offer some to the girls."

Oh, crap.

I grudgingly turned to them and held out the tray. They just grinned, waiting.

"May I interest you in a mini crumpet?"

That was painful.

They burst out laughing as they each grabbed a crumpet.

"Thank you, Blondie," Brenda giggled, resting a hand lightly on my bare waist.

Face burning, I turned and stepped toward the center of the room. Unsure what to do, I stood awkwardly.

Gerlinde came over, took the tray from my hands, and set it down on the coffee table. Then she moved behind me, turned me toward the group, and gently removed the maid’s cap, placing it back on her own head.

"Assume the submissive position," she said.

Oh, no.

I laced my fingers behind my head, raised my elbows, brought my feet together, and stood tall. Eight pairs of eyes studied me with unrestrained glee. I was absolutely miserable.

"I do declare," said Tatiana. "He really is a sight for sore eyes."

Oh Jesus, here we go.

"Oh, he really is," agreed Katarina. "Standing there, all naked and vulnerable."

"It's quite a lovely display," said Josephine.

"And Gerlinde chose the perfect name for that stance: the submissive position," added Elizabeth.

"Most appropriate," nodded Charlotte.

"It exudes submissiveness," said Katarina.

"Servility," said Elizabeth.

"Obedience," Tatiana chimed in.

"Subservience," offered Josephine.

"Meekness," added Elizabeth.

"Surrender," said Katarina.

"Acquiescence," said Charlotte.

"Oh, that's good," said Tatiana. "Acquiescence. I can't top that."

There was a brief pause...and then they kept going.

"His embarrassment is showing through quite delightfully. Just look at those cheeks—such a darling shade of pink," Josephine cooed.

"Tinge of fuchsia, maybe?" mused Tatiana.

"I’d say more like hot pink," said Charlotte.

"Yes!" Tatiana agreed. "Hot pink it is. Well done, Charlotte."

Whatever color they want to call it, I can tell you that my face is blazing hot. And I'm fucking naked!

"Becky," said Elizabeth, turning to my sister. "May I ask how old your brother is?"

Becky smiled, a mischievous glint in her eye. "Would you care to venture a guess, Mrs. Hollister?"

Elizabeth gave me a slow once-over, clearly enjoying herself. “He’s tall, but I’m guessing that’s misleading. I’d say he’s tall for his age.” Then, without hesitation, she pointed directly at my crotch. “I say that based on his very modest level of development. There is some sparse hair, but very little. And his privates are certainly undersized for an adolescent. I'd say he started puberty just recently."

God help me.

"So, I'll go with thirteen? Fourteen maybe, if I’m being generous.”

"He's sixteen," said Becky with a grin.

“Oh, my!” said Tatiana, her voice nearly drowned by the ripple of surprised gasps.

Every gaze, predictably, dropped right to my nether regions.

“A late bloomer,” Josephine observed matter-of-factly.

“Delayed puberty,” Charlotte chimed in.

“Quite boyish for such an advanced age,” Elizabeth added.

“Just a faint dusting of pubic hair,” Katarina noted.

There she goes again with the hair. That lady is twisted.

“I’ll bet he was as smooth as a billiard ball down there not long ago,” she added.

“Bald as a cucumber,” Tatiana agreed with a smirk.

“It appears,” Josephine mused, “that the onset of puberty hasn’t translated into much in the way of any growth of his private parts.”

“I don’t think so either,” Charlotte agreed.

"If it has, imagine what it looked like when he was prepubescent," offered Katarina.

Oh please, somebody just shoot me. Now!

"It is on the small side," said Elizabeth.

“Undersized,” echoed Tatiana.

“Diminutive,” added Charlotte.

“Miniature,” said Tatiana again, as if determined to top herself.

"A cute little thing, wouldn't you say?" offered Katarina.

"A petite penis," Josephine concluded, prompting more giggles.

"A piddling, petite penis," added Katarina, fueling their fire.

“You know,” Tatiana added, catching her breath, “when you look at the...total package, all his bits are rather on the miniature side."

There was a long, suspenseful pause as everyone collectively regarded my “total package” like art critics appraising a very small sculpture.

Then Josephine brought the house down.

“He has mini crumpets,” she declared, deadpan.

That was it. Any sense of decorum or propriety that the ladies had exhibited up to that point had left the premises. Bawdy laughter resonated throughout the room while I stood there, crimson-faced, wishing for the earth to open up and swallow me.

It took a long while, but the laughter finally died down to breathless chuckles and tear-dabbing. Katarina dabbed her eyes with a handkerchief. “Mini crumpets, indeed,” she said, still giggling.

“Oh dear,” Tatiana sighed. “I haven’t laughed like that in years.”

“Neither have I,” Charlotte agreed. “It’s positively good for the soul."

“So,” said Josephine, her eyes dancing with mischief, “what shall we do now?”

All eyes turned to her in curiosity, then back to me.

“Such a provocative question,” said Katarina.

“Quite intriguing,” Tatiana agreed.

“Whatever do you have in mind, Josie?” Katarina asked hopefully.

“Well,” Josephine began, “don’t get me wrong—I’m very much enjoying having him on display for us in the altogether like this. But I thought perhaps we could...amplify things a bit. Stretch the moment. Just a touch more embarrassment, for the greater good.”

“And for our own amusement,” added Charlotte with a sly grin.

“Two birds, one stone,” Tatiana nodded.

“The best of both worlds,” said Katarina.

“Have our cake and eat it too,” Charlotte finished.

Katarina clapped her hands gently. “Oh! Perhaps he has a talent he can share. A song and dance number, perhaps?”

Please, God, no. I can’t...I can’t do this.

"Oh, yes. A naked dance would be rather titillating," mused Josephine with a sly grin.

"More like downright stimulating," countered Katarina with a chuckle. "Shall we have him clear off the coffee table and do his dance up there?"

I stood frozen in dread, heart pounding, as the deranged ladies seriously considered turning me into their own private burlesque act. But much to my relief, saner heads prevailed, thanks to some compassion (finally!) from the lady of the house.

“As entertaining as that sounds,” she said with a chuckle, “I do think we’ve accomplished our mission. The boy’s been properly humbled—and then some.”

A muffled but discernable groan of disappointment emanated from at least two of the ladies.

“Besides,” she added, "I worry that he might just faint from the humiliation and hurt himself if we made him get up there and dance for us with his boy bits on display and bobbing about."

Turning to the maid, she said, “Gerlinde, would you be so kind as to fetch the lad’s clothes?”

“Of course, ma’am,” said Gerlinde, who undoubtedly was also disappointed that the depravities were coming to an end.

While she was gone, Brenda’s mom turned her attention to me.

“As for you, young man,” she said firmly. “I hope you’ve learned a valuable lesson. What do you have to say for yourself? You may speak now.”

I was still standing there stark naked in the submission position, a condition I was dearly hoping to remedy, so I chose my words carefully.

“Yes ma’am. I’ve learned my lesson. Thank you.”

It was not lost on me that I had just thanked someone for orchestrating my thorough humiliation.

Gerlinde reappeared with my clothes bundled neatly in her arms.

“Very well,” Elizabeth said. “You may get dressed.”

The moment my last stitch of clothing was on, she addressed me again. "You may bid farewell to my guests and properly thank them for helping you with your discipline."

Oh, jeez. One last degradation before I go.

"Good-bye and thank you for...for helping me with my discipline," I said, making a point to look each of them in the eye, lest Brenda's mother detain me any longer.

“Oh, the pleasure was all ours,” purred Katarina.

"Indeed it was," said Josephine with a smile, and a twinkle in her eye.

No doubt about that, you perverts, I thought to myself as I made my way, briskly, to the exit.

End
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