Roosevelt Humiliations: The Missing Chapter

Roosevelt Humiliations: The Missing Chapter

Status: In Progress

Genre: Erotica


Status: In Progress

Genre: Erotica


The Blondie character undergoes untoward humiliations at the hands of a posh group of ladies at a tea party.


The Blondie character undergoes untoward humiliations at the hands of a posh group of ladies at a tea party.

Chapter1 (v.1) - Introductions

Author Chapter Note

I got carried away.

I went back to do a minor edit to Chapter 11 (Victoria's Secret) of my "Roosevelt Humiliations" story. There is a scene in that chapter where the Blondie character is forced by his sister Becky to go to the door of her friend Brenda's house to let her know that they are there to pick her up. Blondie is quite self-conscious, because his sister has him dressed in her short shorts, frilly ankle socks and girl's tennis shoes.

Brenda's mother answers the door, and this is where I wanted to make the minor change. All I wanted to do was add a sentence or two in the dialogue between Blondie and Brenda's mother, hoping to add just a tinge of humiliation to the scene.

And that's when I got carried away.

I don't know what came over me, but before I knew it I had added quite a bit more to the scene than I had planned. In fact, I added so much more that I ultimately decided that it was best to just leave the original story alone.

So instead, what we have here is a story of its own. It is called "Roosevelt Humiliations: The Missing Chapter," but technically it will be more than one chapter, since as of this writing I am still not done and have a feeling that I might not be done for awhile. So just consider the chapters within "The Missing Chapter" sub-chapters, if you will.

The story begins as Blondie and Becky arrive at Brenda's house.

Then I got carried away.

Chapter Content - ver.1

Submitted: March 07, 2020

Reads: 2040

Comments: 3

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Chapter Content - ver.1

Submitted: March 07, 2020



“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. It was a borderline mansion, in my estimation. I waited for Becky to get out, but instead she had other ideas.

“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 surprised amusement 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.
She turned her head and called out, “Brenda, there’s a young….” She turned back and looked closely at my face. “There’s 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 responded while shaking her hand.

"Nice to meet you....Blondie," she said.

Again she looked down, then back up to my face. My face was really hot; 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 in the top 1000 of what I'd like to do.

"N-no, thank you," I politely declined.
Finally Brenda came down the stairs.

“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.

“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 wanted to have him come in for a minute and meet my poetry group," said Brenda's mother. "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 for a minute and meet everyone," responded Brenda. "Wouldn't you, Blondie?"

Without waiting for an answer she took my hand and tried to pull me inside. I resisted the tug.

"Please, Brenda, can we just go?" I implored.

Brenda used both hands to pull harder, until I was inside the door, standing in the foyer.

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

"Come, young man," said Brenda's mother as she took hold of my hand and led me toward the living room. I caught her winking at Brenda as she said, "I'm sure my friends will be quite enchanted to make your acquaintance."

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 another woman standing nearby, obviously the maid, dressed in a long, black maid's dress with a white pinafore. She wore a bonnet style maid's cap on her head.

"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.

At that moment Becky entered the room, providing a temporary distraction from their focus on me.

"Oh, hello Becky," greeted Elizabeth. "I was just introducing Blondie to my friends from the poetry group. Ladies, I'd like you to meet Brenda's friend Becky. Becky, please meet Josephine, Katarina, Tatiana and Charlotte."

"It's a pleasure to meet you," said Becky as she nodded at each of the ladies.

There was a momentary awkward silence until the lady introduced as Josephine addressed me.

"Pardon me, young man, if I am approaching the edge of impropriety, but I have to say that I find your choice of apparel rather......intriguing."

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

"He's being punished," stated Becky.

If the ladies were intrigued before that pronouncement, they were absolutely enthralled at this point.

"Oh, pray tell, pray tell, my dear girl!" exclaimed Charlotte. She had a sweet voice with a southern accent.

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

I fidgeted nervously as the ladies' interest in my predicament was piqued.

"My, look at the lad blushing so," commented Katarina. "He does seem quite self-conscious, doesn't he?"

Of course, the comments only caused my face to flush even brighter.

Becky, now grinning, seemed quite pleased at the turn of events.

"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."

I looked up, and the looks of fascination on the ladies' faces indicated to me that the uncomfortable (only for me, of course) topic of conversation was just getting started.

"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?"

"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 were all looking on with bated breath. Even the maid was looking on with rapt attention.

"You see," continued Becky, addressing all of 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 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!" shouted Josephine.

"Such despicable behavior!" said Charlotte.

"Abominable," said Katarina.

"Detestable," said Elizabeth.

"Reprehensible!" agreed Tatiana.

"I know," said Becky. "So now—and it's a long story how it came to be, and it'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!" said Katarina. "The nerve of him!"

"What do you have to say for yourself, young man?" asked Elizabeth.

"I....I'm sorry. I'm really sorry I did it. My friend and I were just playing a joke."

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

I shook my head while staring at the floor.

"'s Becky, right?" asked Josephine. Becky nodded and Josephine said, "Do you think this punishment quite fits the crime?"

Becky had a smirk on her face and said, "What exactly do you mean, ma'am?"

"Well," replied Josephine, "While his enforced outfit is certainly embarrassing for the young rascal, he did see you much more exposed than you are seeing him right now, you poor dear. One might think that it would be appropriate if the young man were to have to shed some of his clothing as a fitting punishment."

"Yes," agreed Tatiana. "An eye for an eye."

"A tooth for a tooth," said Katarina.

"Tit for tat," offered Charlotte.

"Poetic justice," chimed in Katarina again.

"Poetic justice from the poetry group?" laughed Josephine.

"I think that is a wonderful idea," affirmed Elizabeth. "He should at least be required to disrobe to his underpants."

"Here, here!" said an enthusiastic Katarina.

I was getting really nervous, as one might expect. These ladies seemed to be chomping at the bit over an opportunity to humiliate me.

"Girls," said Elizabeth, addressing Becky and Brenda, "Are you two in a rush, or can you stay a bit while we teach this little devil a good 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 she'll respond.

"Oh, I think we can stay, Mrs. Hollister," said Becky. "We can stay as long as you deem necessary."

"Very well, then," said Elizabeth. "Ladies, how shall we go about disciplining this young man?" she said while looking me up and down.

Josephine spoke right away. She seemed like someone I should be wary of. Hell, they all did.

"As you astutely noted, Liz, I think we should have him parade around for us in his underwear."

"Yes," agreed Tatiana. "We need to embarrass him, as I'm sure his poor sister was quite embarrassed when the wretch barged in on her in the bath."

"Maybe we can have him serve us tea while he is so exposed," suggested Charlotte. "I'm sure that would be quite embarrassing for the lad."

All the females tittered at the prospect. A couple of the especially refined ones held the tips of their fingers to their lips as they did so.

I have to at least TRY to get out of this ghastly scenario.

"Please....everyone," I started. "I said I was sorry, and I promise I will never do anything like that again. It was a meant to be a joke, but now I know it was a bad idea."

I looked at Becky.

"Please, can we just go to the car now?"

"I don't think so," countered Elizabeth. "You need to be taught a lesson for your contemptible behavior. And from here on you will not speak unless spoken to. Misbehaving children should be seen and not heard."

Becky and Brenda, who were standing together off to the side, let out an audible chuckle.

"Now, where were we, ladies? Oh yes, the discipline session. We seem to be in agreement that having the young miscreant cavorting about in his underwear would be an appropriate way to proceed."

"I propose that we allow him to retain his shoes and socks," declared Charlotte with a gleam in her eyes.

"Oh, that's a marvelous idea," agreed Katarina. "They do look adorable on him, and I suspect it might raise his embarrassment level up a notch."

"Okay, then," smiled Elizabeth. "Underpants with Becky's shoes and frilly socks it shall be. Now, let me ask you. How shall we go about the disrobing procedure?"

For gosh sakes, I should have just torn the clothes off right then and there. Becky's mother was intentionally drawing out the scene to add to my discomfiture, and she was certainly succeeding in that effort. Plus, I'm sure it was very enjoyable for her and her guests.

"We could have him do a striptease for us," suggested Charlotte.

"That would be entertaining," said Elizabeth. "And quite embarrassing for the lad, I'm sure. So we should have him take his own clothes off?"

"Or I could do it," said Josephine with a sly grin, much to the merriment of her friends.

"Oh, you little devil, Josephine!" cackled Elizabeth. "I think that's a fine idea. All those in favor of Josie undressing the young culprit, please raise your hands."

The hands of all five ladies rose in the air. Becky and Brenda seemed content, at least for the moment, to not be active participants in the proceedings. But, judging by the looks on their faces they were enjoying themselves immensely.

"It's unanimous," declared Elizabeth. "The removal of his clothing will be carried out properly by Josephine."

All eyes turned to me.

"Come," beckoned Josephine as she motioned with her fingers for me to approach her.

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