Queen of Humiliations

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Status: In Progress  |  Genre: General Erotica  |  House: Stripping and Humiliation

Fourteen-year-old Arnie Benson finds himself standing before a girl with a history of humiliating boys. One who has a nickname of The Queen of Humiliations.

“Just what the hell do you think you are doing?”

Arnie Benson turned.  He wondered where the hell Diana Caulfield had come from.  And just how much trouble he was in.

“You were peaking in my sister’s room, weren’t you!”

The yelling had attracted Olivia Caulfield’s attention.  After wrapping a towel around her upper body, she pulled up the blinds and opened the window.  “What is he doing here?” the thirteen-year-old demanded.

“He was looking in your window.  Your blinds were up an inch or so from the bottom.  Did he see you?”  Diana turned suddenly as she saw the boy take a step.  “Don’t you dare move,” she ordered.  “You’re on your way to big time trouble.  What did you see?”

Arnie was scared.  Diana did that to boys.  She could be quite cruel and mean.  He’d heard she had a title: Queen of Humiliations.  And he’d been caught red-handed trying to get a peek at her younger sister.  “I, uh, nothing.”  He saw the doubt on Diana’s face.  “A little.  Just a quick glimpse of one of her tit, uh breasts.  I hardly even had time to focus.”

“Were you covered below?” she asked her sister.

“Yeah, fortunately.  But if you hadn’t showed up when you did it would have been different.  I was about to remove the towel and get ready for bed.  Should I call 911 and report him as a peeping tom?”

“You could,” Diana reasoned.

“No, please, I hardly saw anything,” Arnie pleaded.  An arrest would ruin his hopes for a major college scholarship in three years.

“You want to see him topless?”  Diana didn’t wait for a response.  “Take your shirt off.”

Embarrassed, he did it.  Anything to keep from having Olivia call the police.

“Shit, you’re a sophomore, right?” Oliva asked.  “Raise your arms.”  The boy did as she ordered.  “He doesn’t even have any pit hair yet.  He’s just a little boy.”

“I skipped fourth grade,” he submitted.  “I’m only fourteen, but I am in tenth grade.”

Diana had an idea.  One she had been meaning to do to someone deserving for a year or so.  But her reputation kept most boys from doing anything stupid around her.

“I suppose you’d rather not have us tell everyone in school that you are a weirdo who gets off looking at younger girl’s chests.  What will you do to keep that our little secret?  And for us to not call the cops?”

“Anything, please.”  He felt horrible, but he had to keep this quiet.  He was already a bit of an outcast.  He wasn’t sure what would happen if other kids found out he’d been trying to see Olivia Caulfield naked, but he was sure it wouldn’t improve his status, especially around girls.  He unbuckled his belt.  “Do you want to, uh, see me?”

“Oh hell yes,” Olivia said.  “Take them off.”

“No,” her sister countered.  “Put your shirt back on.  Here is what you are going to do.”  She pulled the boy under the window so Olivia could hear it all.  She gave him a series of instructions, happy to see the fear in the boy’s eyes.  It was a look she’d seen in other boys in other times.  And one she enjoyed causing.

“You have to make a choice right now.  Do what I just outlined, exactly as I stated it, or we start by calling 911.  And if you fail to complete the task, well, you’d better find some other place to live, because your life here will be ruined forever.”

It was horrible.  Nothing could possibly be worse than following her instructions.  Except being arrested.  Having every kid in school knowing what he’d been arrested for.  His family’s shame and anger directed at him.

“Well?” Diana questioned when he didn’t say anything.  “Do I tell Olivia to make the call right now, or do you want to keep what almost happened here tonight between the three of us?”

“I, uh, want to keep it between us, but can’t I …”

“No, you can’t change anything.  You do it exactly the way I stated or it doesn’t count.”  She knew how hard this had to be for the boy.  Stripping him in public would be fun. But she’d done that three times already.  Making a boy strip himself, making him dependent on her afterward, that was going to be so much better.

“I, uh, damn.” He paused.  “Okay, like you said, but you two need to keep it …”

“Are you saying we might not keep our end of the bargain?  Do you think we’re a couple of cheats?”

“No, I just wanted to be sure,” he pleaded.  “I mean, it’s a uh, it will be, uh …”

“Embarrassing,” Olivia smiled.  “Just like it would have been for me if my sister hadn’t caught you.  We are trusting you to do it all.  I don’t think you want to find out how much worse things can get if you try and backout of a deal with her.”

Arnie hardly slept that night, thinking about the plan.  He hoped he was brave enough to do it.  He knew that Diana wouldn’t hesitate for a second to completely destroy his little world.

The next day, after school, he got all the materials he would need.  The following day, Saturday, he’d be in the park at 9:00 a.m.  Or else.

That night, he did some of the preps.  He didn’t have a lot of hair down below, but the chemical he’d bought took care of what little he did have.  Same with his armpits, which had even less to start with.

Saturday morning, he pulled out an old pair of briefs.  He used a permanent marker to put his name on the outside of the elastic band, and put them one.  Then shorts, a pull-over shirt, socks and shoes.  He left early, hoping to be able to stage himself before other kids showed up.  He had to assume that the Caulfield sisters had invited their friends.

Getting there early didn’t help.  A score or more of kids were already there, including Diana and Olivia.  Shaking, he was committed to doing it.  He started by clipping the handcuffs to two crossbars of the playground monkey bars.  Then he pulled his shirt up to his neck, with his arms out of the sleeves.  He hesitated, but a look from Diana made him continue.  Kids moved closer, eager to see what this was all about.  He unsnapped his shorts and let them fall to his ankles.

Laughter came from the audience.  Kids started asking why he was doing this. And if he was going to remove everything.  Arnie did his best to ignore them.He pushed the briefs down on top of his shorts.  And then, as the ultimate humiliation, he called on a sixth-grader, Luca McBride, to come and do the crowning act.  He had once made fun of Luca’s Halloween costume.  Now the boy was eager to be given the only chance for revenge he was likely to ever get.

The boy, who he had called the night before, proudly stepped up and snapped each of the open cuffs from the two pairs of handcuffs over his wrists.  As the kids gathered around laughing, he pulled the keys from the lock and hung them around Arnie’s neck.  Then he turned and took a bow.

Arnie was now naked from his neck to his ankles, with his arms pulled out to the sides and raised slightly.  And he now sported an erection.  Fear had not kept it from rising.

“He’s a baldy,” a ninth grader yelled.  “With a tiny little dick.”

The baldy part was accurate, the chemical he had used the night before had seen to that.  But tiny dick was unfair.  He knew he was just slightly below the peak of the age curve for penis length. But how could he possibly defend himself as he stood there naked in front of dozens of his peers, with more still arriving.

Olivia stepped forward.  “I want those,” she said as she pointed to his briefs.  “You will not wear underpants again until you remove these from where I hang them.”  She turned to the boys in the crowd.  “Just think how embarrassing it must be when you guys pants a boy.  Think of how much worse it would be if that boy wasn’t wearing underpants.”

Arnie knew the next few days were going to suck.  He was sure to get pantsed on a regular basis.  Something that only freshmen were supposed to endure.  He was a sophomore.

“Lift,” Olivia ordered as she touched his right leg.  He complied, and she removed the shorts and briefs from over his shoe.  Then she repeated the process with his left leg before discarding the shorts and showing his briefs to the crowd, with his name clearly visible on the waistband.  But she wasn’t done with him.  “Until you have these back, you will do nothing to prevent kids from having fun depantsing you.  No belts, no tight pants.  Wear loose shorts that can slip over your hips.”

“I think I’ll claim these,” Luca McBride declared as he picked up the shorts.  “If you figure out how to get someone to unlock the handcuffs, you and I can talk about getting them back.  Or you can just go home naked.”  He looked at Arnie and saw the shirt.  “Oh, I almost missed that.”  He reached up and pulled the shirt over Arnie’s head.

Not that it mattered now, but it was sure to in the next hour or so.  The only change for now was that he was naked from the top of his socks upwards.  And the realization that Diana hadn’t given him any instructions on how to get free.  He assumed she would take care of that. If it was to be up to him to figure it out, he thought this might be a much longer day than he had anticipated.

“Do you cum yet?” Luca suddenly asked.

Arnie was surprised the eleven-year-old even knew anything about that.  He hadn’t back when he was in sixth grade.  “Yes,” he replied.  “I’m fourteen.”

“Well, we’ll see.  I cum too.  Do you believe that?”

“I guess,” Arnie lied.  No way did a kid that age shoot.

“You don’t sound like you believe me,” the kid continued.  “Are you sure you want to stick with the answer you gave?  Or would you rather demand some proof that I’m not lying?”

Arnie realized the boy really wanted him to not believe, but he couldn’t figure out why.  This whole thing was strange.  Clearly this had been set up by Diana and-or Olivia.  “You can prove it if you want,” he stated, taking a middle ground.

“We’ll see.  But first, I’m going to demand that you prove you can.  You said you were fourteen, like that means anything.  But you look younger than me.  Are you right- or left-handed?”

Arnie was not liking where this was going.  “Right,” he stated.

“Then I’m going to release your right hand.  If you reach for anything except your tiny dick, I will kick you in the balls.  You will have three minutes to prove you can cum.  It’s a condition for your release.”  Luca pulled one of the two keys from around Arnie’s neck and tried it on the handcuff to his left.  It worked, and as the teen reached for his dick, he pocketed the key and then stepped aside so that he wasn’t blocking anyone’s view.

Girls gasped and giggled.  Boys cheered and laughed.  Arnie couldn’t ignore them.  He was stroking his dick, but it wasn’t working.  In fact, the opposite was happening.  As more kids crowded in, especially girls from his grade, his dick began to soften.

“Time’s up,” Luca said after about three minutes.  “I’ll give you more time if you’ll call on three girls to come up and give you a spanking for failing.”

Arnie suddenly realized the trap he was in.  He couldn’t fake it.  In order to shoot, he would have to somehow get really turned on.  To do that in front of a mixed group of boys and girls just because Luca was making him do it might be impossible.  But the boy said it was a condition for his release.

“I’ll pick the girls if you don’t,” Luca warned.

Younger, and smaller girls who couldn’t hit as hard was Arnie’s choice.  He picked the smallest three he could see.

“Ten smacks each,” Luca instructed.  Olivia told him to invite a few girls from sixth grade because of this, and he knew he’d be a hero to them.  They eagerly stepped forward, each trying to be the first one.

They didn’t hold back, and after the first girl was done, Arnie’s cheeks were burning.  Those on his face because of the humiliation of being spanked by a girl 3 years younger than him.  And those on his ass because she hit hard.

“Thank her,” Luca ordered.

Another humiliation.  The second girl didn’t hit quite as hard, but it didn’t matter, the ten strokes nearly brought tears to his eyes.  Arnie thanked her without being ordered to.  Before the last girl reached her fifth stroke, he was dancing around, bound to the monkey bars by his left arm.  The girls got a big cheer as she finished.

“I’ll double the time,” Luca said.  “You now have six minutes to prove you can cum or you’ll have to choose three more girls.”

Arnie used his free hand to wipe snot and tears from his face.  This was worse than his worse nightmare.  If he was to get free, he had to find a way to cum.  In order to do that, he would have to want it.  He had to get into the comfort region he normally was in when in bed, alone.  With an audience that now numbered in the mid-twenties, he had to somehow want to let them see him shoot.  He closed his eyes and tried to calm himself.  He thought about what he’d seen two nights ago.  Not one brief look at Olivia’s tit, he’d actually seen both of them.  Clear, and for several seconds.  He could estimate the size.  The large pick circle around each nipple.  His hope that she would drop the towel.

It was working!  He was hard again.  He worked to keep focused.  To try and ignore the laughter, cheers, and comments coming from in front of him.  Especially the memory that this all had started with Diana yelling “Just what the hell do you think you are doing?” moments before her sister was about to show her slit.  He managed to bury that and instead focused on a fantasy.  That he was back at her window, jacking off as she danced inside her bedroom, totally naked and unaware he was there.

Before he was even aware it was starting, his first burst shot out of his dick.  It ruined the dream state he was in and left him suddenly aware that he was jacking off in front of dozens of kids.  But he managed three more bursts before all desire melted away again.  He opened his eyes.

Strange.  Not a single person had a cell phone out.  He would have bet that videos of his performance would have gotten to everyone in school, yet nobody had thought to make such a video.  Or, more likely, Diana had forbidden it.

“Okay, I guess you weren’t lying,” Luca laughed.  “I’m sure everyone here is proud of you.”  He smiled as he listened to the laughter and comments his statement had drawn.  “But I want to know if you can do it twice.  I can’t, not yet anyway.  Do it a second time, right now, and you win your freedom and your shorts.  Fail, well, it probably is best that you don’t think about that.  Focus on a happy thought, like getting dressed again.”

The first try had utterly failed.  Maybe he’d just gotten lucky the second time.  But to do it again would be even more difficult.

Arnie looked at Diana, who simply smiled at him.  He was more and more coming to believe that she really would leave him out here naked if he didn’t keep doing what she wanted.  The crowd of kids moved closer.  A few started chanting, “Do it.”

As before, he tried shutting out all distractions.  This time, instead of picturing Olivia, he focused his inward attention on Diana.  The curve of her breasts.  The way her pants hugged her hips.  Then he imagined her slowly stripping.  An idea struck, and he added himself, in her room, watching as she stripped for him.

Of course, he had never seen her in anything less than a bikini, but he did possess a powerful imagination.  In his mind, he made her tits bigger.  Much bigger.  And as she removed her panties, she handed them to him.  Then they kissed, her tongue reaching into his mouth, touching, touching, …  Wham!  The first shot of cum jolted him. The second was even better.  Even though the dream was busted, he managed two more before surrendering to the reality of the situation.  He was the one who was naked.  And not just her, but upwards of thirty other kids had just watched him jack off for the second time.  The horror of it made his dick wilt in his hand.

“Wonderful, I’m sure everyone enjoyed your show.  I’m glad you offered to do it for us.”

Arnie didn’t think that anyone believed he had ‘offered’ to do this.  But that would from this day forward be the way kids would speak of it.

“As we agreed earlier, your briefs will be hanging somewhere.  Remember, you are not to wear any underpants until you find and remove the pair you wore here today.”

He looked around for Luca, who was in the back, spinning the shorts around over his head.  It was clear that he was not going to come forward.  He would have to push through the crowd to go to him.

Hands touched him as he pushed through.  A few girls stood in front of him, getting a good look, and forcing him to go around them.  Finally, he reached the spot where Luca stood.

“We’ll start with your shirt.  Ask me to give it to you,” the boy demanded.

“Give me my shirt.”

“You didn’t ask, you demanded.  Try again.”

Arnie considered just taking them from the boy.  The idea that maybe that was exactly what they wanted him to do made him pause.  “Would you give me my shirt?” he asked, trying very hard to make it sound casual and not angry.

“You didn’t say the magic word,” Luca replied with a giggle.

In his head, he’d already busted the sixth-grader’s nose and taken his clothes.  But he was convinced that any attempt to get them without them being offered would be met with even more humiliations.  “Would you give me my shirt please?” he asked.

Luca was living for the moment.  His fifteen minutes of fame.  Humiliating a boy almost three years older than him.  “Only if you promise to thank me after I do.”

The kids had all gathered around.  A naked, hairless fourteen-year-old all but begging a kid who was only twelve.  His ears were so hot he thought they might burst into flames.  “I promise to thank you.  Please give me my shirt.”

“Here,” Luca said after letting a few seconds of suspense go by.  He held it out.

“Thank you,” Arnie said as he took them.  It was buttoned.  He dropped it.

“Would you please give me my shorts?  I’ll thank you if you do.”  Before he could move, someone grabbed his shirt.

Luca handed over the shorts and got his thank you.  The shorts were buttoned and zipped, and before he could put them on, he had to stand there exposed for several more seconds while he fixed it.

His shirt was gone.  Perhaps a trophy for some girl.  It was one more bit of humiliation.  He would have to go home shirtless.

He was able to hide in his house and yard the rest of the weekend, but Monday morning he had to go to school.  He picked a pair of shorts that were too big for him in the waist, and a button-down shirt that came down to around dick level.  That was the best he could do.

He was pantsed twice on the way to school, and again at his locker. This slowed him down, and he was almost the last person to enter his homeroom.  There, on the back of his chair, was his briefs, his name clearly visible.  He snatched them and shoved them into a pocket, nearly pantsing himself in the process.  His whole homeroom was laughing as the teacher entered.

“What’s so funny,” Mr. Hartman asked.  Nobody answered, and the room got quiet as he took attendance.  “May I go to the bathroom?” Archie asked when the teacher called his name.

“No, you had plenty of time to go.  I heard a lot of laughter coming from around your locker this morning.  If you needed to go, you should have done that instead of entertaining your fellow students.”

He was pantsed again after homeroom was dismissed, and again before his third class.  Both classes had been at opposite ends of the school, which didn’t leave him time to use a restroom.

Then came lunch.  He was about to enter a restroom just outside the cafeteria, but the janitor got there three steps ahead of him.  “Sorry, there’s a leak in here.  This restroom is closed until I repair it, you’ll have to use another one.”

Arnie was pretty sure that if he went to another one there would be someone else there to keep him from going in.  He entered the cafeteria and got in line.

As he was carrying his tray to an empty table, he was pantsed again.  He had a choice.  He could drop his lunch, or waddle his way to the only table he knew he was to go to.  The one where Diana Caulfield sat with two of her friends.  Maybe this would be the end.  With a roaring sound of laughter, he made his way to the table, his lower half exposed for nearly half of the student body.

He set his tray down and pulled up his shorts just as the principal entered, demanding to know what the noise was about.  It quieted down, and Mrs. Johnson looked at the table he had just sat down at.

“Mr. Benson,” she boomed.  “I’ve heard three reports of you causing a commotion in the halls and your homeroom.  If it happens again, you will be in my office until you can explain what you are doing.”  She didn’t wait for an answer, but continued staring at him as she left.

“My, my, my,” Diana said.  “That sounds pretty serious.  Perhaps you should put your undies on now.”

“Here?” Arnie asked.  He looked around.  Over a hundred of his school mates were looking in his direction.

“Yes, for your own safety.  You wouldn’t want for old Mrs. Johnson to wonder why you have your underpants in your pocket and not on your body.  Who knows, maybe she’d even pants you just to see if you had a second pair under your shorts.”

He was scared.  Horrified.  He started to unsnap the shorts, but Diana grabbed his hand and pulled it back.  “No, you can’t do it under the table.  Stand here, against the wall, and put them on.  You’ll have to hurry in case the principal returns.”

He looked around in horror.  He didn’t know if the rest of the kids knew what was going on, or if they were just sure that he was going to do something entertaining just because he was sitting next to the Queen of Humiliations.

“Or, you can let me keep your underpants safe until tomorrow when things have calmed down.  Of course, I wouldn’t expect you to be wearing another pair when you come to school.”

In other words, he’d keep on being pantsed until he submitted to her horrible plan.  With shaky legs, he rose and moved around the table.  He found that when in front of the wall, the staff at the serving line couldn’t see him.  More and more kids were still coming in.  The longer he stood there, the number who would see him would keep growing.

He could see dots in front of his eyes as he undid his shorts and let them fall to the floor.  The roaring of laughter started up immediately as he stepped out of them.  He thought he was going to faint as he bent over to get his feet into the briefs, but he managed to get them on.  He was just fastening his shorts when Mrs. Johnson returned.  She looked at where he stood the moment she entered.  “My office, Mr. Benson.  NOW!”  she stormed out and he had to hurry to catch up, his lunch abandoned on the table.

Once in the office, she slammed the door closed.

“I was told you are not wearing underpants, and that you encouraged other students to lower your pants,” she accused.  “Is that true?”

“No ma’am,” Arnie said.

“Do you have underpants on?”  When he nodded, she added, “Let me see.”

He could have refused.  She had no right to demand he remove any of his clothing.  But if he did refuse, she would likely suspend him.  Again, his chances of getting a major college scholarship would vanish if that happened.  He stood and unzipped his shorts, pulling the opening as wide as it could go.

“I can’t tell for sure.  Lower your shorts.”

A very unusual and illegal request.  And exactly as Diana had said she would do.  Meaning that the person who told her he was entertaining his classmates by exposing himself was her.  He unbuttoned them and let them fall to his ankles.

She stared for five seconds before telling him to get dressed.  “There had better not be any further disturbances surrounding you today young man,” she instructed.  “If there are, this will go to the police.” She held up a picture taken from the top of the hallway near his locker.  It was blurry, but he was clearly shown surrounded by other students pulling up his pants.  And he didn’t have underpants on.

“You didn’t know we have security cameras in the hallways, did you?”

“No ma’am,” he gulped.  He hadn’t known it.  And now she had a picture of him proving her original accusation.  He could now add her to the list of people who’d seen his dick.

“I’m only going to let this slide because I know you want to go to a good college.  I can see from this picture that you are, uh, shall we say, less developed than a typical sophomore.  Maybe you thought this was funny.  Your fellow classmates seemed to agree.  But even if you are a child, I can’t have pranks like this occurring in my school.  It needs to end.  Now.”

“Yes ma’am,” he mumbled.  She thought him a child.  She’d seen him basically naked.

“One last thing.  You were having lunch with Diana Caulfield.  Did she have anything to do with this? Did she encourage you to act out?  Or somehow convince you that you should?”

Arnie considered this the last test.  Of course Mrs. Johnson knew that Diana was behind it all.  But would he admit it?  Was she trying to finally catch the evil girl?  Or was she allowing it to occur?  If the later was correct, telling her now that Diana forced him into it would launch a whole new series of humiliations.  But admitting that it was all his idea would forever keep him from blaming her.

“No ma’am.  Her table was the only one open.  I don’t know much about her, really.”  He tried to read her eyes, but she gave nothing away.  She stared at him for a few seconds before saying, “Go and finish your lunch.”

His tray was right where he’d left it, but Diana and her friends were gone.  He ate quickly, finishing just before the bell rang.  He had to run to his next class, his shorts threatening to come off with each step.  But he made it on time, and was not pantsed again.

Submitted: November 08, 2021

© Copyright 2023 Pietar. All rights reserved.

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Add Your Comments:


Callum white

Great story

Mon, November 8th, 2021 4:21pm


Good story. And re your forum post - no, I don't mind in the least that you used a few of my words to write the kind of story I like best.

Tue, November 9th, 2021 6:04am

Robert Brooks

Brilliant story Pietar! I loved the bit about Arnie having to put on an old pair of briefs and write his name on them specially for his punishment! Very embarrassing for him to find them draped over his chair at school where everyone can see! Telling him he had to make it super easy for people to pants him was a really nice idea, I look forward to more stories involving the Queen of humiliations, she seems like a lot of fun!

Tue, November 9th, 2021 7:01pm

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