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Re: Tommy's Debasement

Posted: Wed Mar 19, 2025 10:41 pm
by NickTwisp
My Mom would always insist that I take pajamas to the sleepover. But I never wore them at his house. My friend always slept in his underpants, so I did too. Once we retired to his bedroom for the night, we'd strip down to undies. A few times I got up the nerve to walk down the hallway to the bathroom in my underpants past the sister's room; she never came out to catch me. Part of me probably wanted her too.

Tommy's Debasement, Chapter 14

Posted: Fri Mar 21, 2025 7:22 pm
by Blondie
Image

Chapter 14: The Dreaded Dance Class

The Gymnasium

“Alright, class, it’s time to head down to the gymnasium for dance class with Miss Richards,” Sister Ruth announced. “I’ll be joining you today to see how you’re all progressing.”

The class formed two lines, the boys in one line and the girls in the other. Tommy was ecstatic to be wearing his own school uniform (or any clothes at all, for that matter!), and felt relieved to be in the boys’ line for the first time that day. However, despite the relief, there was still a lingering unease about Sister Ruth tagging along to observe the lesson.

The gymnasium was arranged like any standard school gym, with a polished hardwood floor typically used for basketball. Most of the retractable bleacher seats were pushed against the walls, except for one section in the middle that had been pulled out, ready for the students to sit. There were eight rows, each accommodating nine or ten students. There was a total of seventy-three students in the dance class—forty-one girls and thirty-two boys.

Front and center, Miss Richards had positioned a demonstration platform. It stood three feet high, with a sturdy base and locking wheels, offering over three hundred square feet of space—large enough for a few people to dance on it comfortably.

Miss Richards stood atop the platform as the students trickled in. She watched them with a keen eye, hands resting lightly on her hips.

Tommy was among the first in the gymnasium. When he made eye contact with Miss Richards, her lips curled into a knowing smile. He blushed profusely while wrenching his head away and making a beeline for a seat toward the back, heart pounding.

But something told him that no matter how far back he sat, there would be no hiding from her.

Miss Richards always insisted on a strict boy-girl seating arrangement to ensure that every student had a dance partner within arm’s reach. But with more girls than boys in the class, some of the girls inevitably had to double up.

As fate—or rather, Tommy’s abysmal luck—would have it, his eighth-grade tormentors from recess and lunch had already spotted him. They wasted no time claiming the open seats around him like predators circling their prey.

Karen slid onto the bench to his left. Linda took his right. Directly in front of him, Nancy turned in her seat with a wicked grin, while Cindy and Sally plopped down behind him, effectively boxing him in.

The eighth graders were surprised, and more than a little disappointed to find Tommy wearing his own uniform.

“Gee, Tammy,” Karen pouted, trailing her fingers through his hair. “What happened to your pretty skirt and blouse? You almost look like a boy in those pants. And where’s your training bra, you little hussy?” she added in a whisper, just loud enough for the other girls to hear.

Tommy yanked his head away. “Leave me alone. It’s over,” he muttered.

Before she could respond, Miss Richards clapped her hands for attention.

“Alright, class! We’ll begin today’s lesson by reviewing the ballroom dance steps we’ve learned so far.” She let her gaze sweep over the seated students, though she already had her choice in mind. “I need a young man to volunteer as my partner for this demonstration.”

Predictably, not a single hand went up.

“Well then, I suppose I’ll just have to choose someone.” She let the moment stretch just long enough for all of the boys to shift uncomfortably. Then, as if she had only just made her decision, she turned her eyes toward her target.

“Let’s see….Tommy, would you come down and join me up here on the platform, please?”

Tommy’s stomach lurched. Hearing his name spoken so sweetly by Miss Richards sent a fresh wave of dread crashing over him.

As he reluctantly rose to his feet, he felt a sharp pinch on his backside. He spun around just in time to see Karen withdrawing her hand, her expression one of pure mischief.

Tommy swatted her hand away and hurried down the bleachers, trying to ignore the chuckles from the girls around him. He ascended the platform’s steps, his legs feeling heavier with each one.

Miss Richards was waiting, watching his approach with an expression that was far too pleased.

Oh, she had been looking forward to this moment.


Miss Richards

Betty Richards was waiting with quite a bit more anticipation than she usually had for the weekly dance class. She had felt a stirring within her when she first saw the boy’s clothes on the ground under her window, and that feeling had been with her ever since.

She wasn’t sure why she had strong tendencies towards enforced humiliation; all she knew was that it stimulated her like nothing else could.

On more than one occasion she had taken advantage of her position of authority and used humiliation on a student as a form of punishment. One of her favorite practices was pinning a pretty pink bow on a blushing boy. She once made a girl get on all fours on her desk and bark like a dog. Yet another time she put bunny ears on a boy and made him hop around the classroom.

For her, the resulting crimson-faced humiliation was delicious.

And yet….none of those past experiences quite compared to the potential of today. Forced public nudity had to be at the top of the list of the humiliation experience. And she would take advantage of the dance setting to augment the humiliation of the poor unfortunate.

She almost pinched herself to make sure she wasn't dreaming, such was the incredulity of her good fortune.

She had watched Tommy’s earlier ordeal in the schoolyard from her window, her enjoyment only growing as his embarrassment deepened. Now, she had him right where she wanted him—alone on stage, under her watchful eye, with an audience of nearly seventy-three eager spectators.

She had to pace herself, had to savor every moment. After all, there was still a whole hour ahead.

And oh, what a wonderful hour it will be.

Tommy had grudgingly made his way to the platform. Miss Richards watched his approach with barely concealed delight.

“Alright, Tommy,” she purred. “Let’s see what you remember from last week’s lesson. Sister Ruth, would you be so kind as to start the music?”

A Strauss waltz echoed throughout the gymnasium. Miss Richards extended her right hand. Tommy, not much of a dancer, instinctively took the wrong one.

“No, no, my right hand, Tommy,” she corrected, shaking her head.

Tommy quickly switched, already feeling the heat creeping up his neck. He attempted to move through the steps, but his coordination was poor. He moved around clumsily, either stumbling over his own feet or stepping on those of his instructor.

“Stop the music,” she called out, sighing in mock exasperation. “Tommy, it looks like you didn’t learn much of anything last week.”

She let the silence stretch just long enough for the giggles from the stands to swell.

“And you’re awfully stiff,” she continued, tapping her chin thoughtfully. “Sister Ruth mentioned that you’ve already been disciplined today. Would you say you learned a lesson from that, Tommy?”

“Yes,” he mumbled, staring straight down.

Miss Richards tilted her head. “And what form of discipline did Sister Ruth use on you?”

Tommy was silent.

“I asked you a question, Tommy.”

““I-I had to take my clothes off,” he said, barely above a whisper.

The class, hanging onto every word, burst into delighted laughter. Miss Richards met Sister Ruth’s gaze, and the two shared a subtle, knowing smirk. Meanwhile, Tommy stood before them, his face burning a furious shade of red. Betty Richards couldn’t help but smile to herself.

Ahh… there it is. The first blush. And it only gets better from here.

“Well,” Miss Richards mused, “that must have been quite embarrassing for you. But, you know….maybe it wasn’t such a bad idea.”

The boy’s jaw dropped in disbelief at the suggestion.

That’s right, young man....it’s happening all over again….and I’m loving every second of it.…time to start stripping.

“Perhaps your clothes are just too confining,” she continued sweetly. “Maybe you’d move a little more freely on the dance floor if we took some of them off.”

Tommy’s brain scrambled for words, but nothing came out.

“It'll be okay, Tommy,” Miss Richards teased, her lips curving into an amused smile. “Let’s start small. Take off your shoes. That way, if you step on my toes, it won’t hurt as much.”

Tommy stood frozen, not at all keen on yet again removing an article of his clothing.

"Come on, Tommy," prodded Miss Richards. "Time is wasting. Let's get those shoes off."

Tommy reluctantly reached down and removed his penny loafers. Sister Ruth was standing next to the podium and holding her hands out. Tommy handed them over to the entertained nun. Betty Richards had a gleam in her eye.

He’s at my mercy. This is actually happening!

The music started again, but the absence of Tommy’s shoes did nothing to help his fluidity on the dance floor. He again was stumbling all over Miss Richards.

“Stop the music!” she called out, exasperated but clearly amused. “Alright, Tommy, I can see that simply taking off your shoes isn’t going to do the trick. We’re going to have to go back to basics.”

Tommy had a sinking feeling that her version of “basics” wasn’t going to end well for him.

Miss Richards turned him to face the eager audience. With one hand on each of his shoulders, she positioned herself behind him. “Okay, Tommy, let’s practice our steps. Forward two, back two, side to side. That’s it. Keep going until I say stop.”

Tommy obeyed, stepping awkwardly in time with her instructions, hyper-aware of all the eyes on him.

That’s it, my little pet….you keep doing my bidding….in the meantime, I’ll go ahead and relieve you of your shirt.…oh, this is so exciting!

While keeping perfect step with him, Miss Richards reached around from behind and deftly unfastened the top button of his shirt.

“One, two, back, that’s it, Tommy,” she continued, her voice smooth and soothing, as if she weren’t currently stripping her student, one button at a time.

Tommy, lost in his concentration, didn’t notice at first. But the tittering from the bleachers grew louder, and his eyes darted down just in time to see Miss Richards flick open the final button.

Before he could react, she slid his arms back, slipped the shirt from his body, and handed it off to Sister Ruth, who took it with a devilish wink.

The seventh graders were once again in a state of merriment, while the eighth graders were wide-eyed, witnessing a forced disrobing for the first time. Karen especially was so excited at the scene that she almost peed her panties.

Laughter rippled through the gymnasium. Tommy’s face burned as he stumbled through his steps, now clad in just his undershirt and uniform pants.

Miss Richards, of course, wasn’t finished.

I’m so glad he’s wearing a tee shirt.…it will prolong this wonderful moment, and it means there is one more article of clothing I get to take off....oh, this is such a treat.…I just can’t believe my good fortune!

Hmm, what shall I tackle next, his pants or his undershirt?….golly, that’s a tough one.…I could strip him to his waist.…certainly losing his pants would be more disconcerting for him, so I could save that for later.…ah, but it would be so delicious to have him dancing around in his underwear.…yes, let’s get those pants off first.

As she guided him forward, her hands drifted down to his waist, expertly locating his belt buckle.

Tommy’s survival instincts kicked in. His hands shot down to stop her.

“Put your hands on your head, Tommy, and keep them there, please,” she said, softly but authoritatively.

Tommy hesitated, glancing toward Sister Ruth. The nun’s sharp gaze sent a shiver down his spine. He knew resistance was futile. Shoulders slumping in resignation, he raised his hands and placed them atop his head.

Miss Richards chuckled softly to herself. With practiced ease, she unbuckled his belt, unfastened the button, and slowly, deliberately, unzipped his pants.

I really hit home with that one.…he actually put his hands on me….oh, he looks so vulnerable now, in that position.…putty in my hands….okay, the belt’s undone.…feels like one button, then his zipper, and then down they’ll go.…take it slowly, Betty, take it slowly….enjoy the moment.

Tommy froze. The laughter around him swelled as his loose trousers sagged precariously. His mortification deepened with every passing second.

“Just keep dancing, honey,” Miss Richards murmured, gently nudging him forward. “That’s it… don’t stop until I say so.”

Tommy obeyed, his movements stiff and jerky—partly from nerves, partly from sheer desperation to keep his pants up.

But gravity took over. Each awkward step loosened the grip on the waistband, allowing his trousers to inch lower and lower. Tommy tried to spread his legs to keep them up, but the fabric tangled him further, limiting his steps to tiny, humiliating shuffles. Miss Richards watched with stimulation as, while the gymnasium erupted into wild laughter and cheers, his pants inevitably slumped to a heap around his ankles.

Okay, the button’s undone….here’s his little zipper.…down it goes….ooh, I think I felt him flinch; how delightful.…all right then, I’ll just put my hands back on his shoulders and enjoy the show.…hey, the little devil stopped dancing.…gotta keep him moving….there we go.…oh, yes, they’re starting to fall….oh, look at his cute little white undies…listen to the kids out there, they’re enjoying this, too…look at ‘em, their facial expressions, they can’t believe it.…the poor dear, he must be miserable.…oh, how comical, he’s trying to keep his pants up by holding his knees out.…I don’t think so, my little friend.…yep, there they go, all the way down….oh, that was funny....listen to all the laughter...and look at his slender, pretty legs, how delectable….and Ruth was right, they’re so smooth.…oh, this is just precious!


Tommy

From Tommy’s standpoint, it was, of course, a living nightmare. When Miss Richards had first called him down, he had slumped his shoulders, already dreading another round of unwanted attention. But this—this was beyond what he had imagined. Then, when she hinted at removing clothing, he thought she was only trying to scare him into dancing better. Surely, she wouldn’t actually make him strip in front of both the seventh and eighth-grade students. Surely Miss Richards wouldn’t subject him to such debasement.

But then he had to remove his shoes and hand them to Sister Ruth. When Miss Richards removed his shirt and shared a wink and a smile with Sister Ruth, Tommy had a knot in his stomach, and a terrible, sinking feeling came over him.

He was horrified when Miss Richards had her hands on his belt buckle, and he instinctively reached down to pull her hands away. Then he heard the words “Put your hands on your head, Tommy, and keep them there, please.” It was an all too familiar position for him, and everything went downhill from there. In short order, Miss Richards was leading him around the dance floor with his pants around his ankles.

Once again, Tommy was the victim of a teacher’s prurient desires. He could only hope that Miss Richards had a little more compassion in her than the diabolical Sister Ruth.

But as he stood there, pants pooled at his ankles, cheeks blazing, and laughter echoing through the gymnasium, that hope was slipping away fast.

Re: Tommy's Debasement

Posted: Fri Mar 21, 2025 7:45 pm
by Blondie
As noted earlier, Chapters 14 through 18 were lost in a glitch while we had the dreaded spammer. I've decided to delete Chapters 19 through 22 (to be re-added later, of course) so that the chapters would not be posted out of order. As you can see, I have added Chapter 14 today.

As I'm going over each chapter to ensure proper formatting, I have been unable to keep myself from making some changes along the way. Nothing major—the story remains pretty much intact as originally written—but you might see some slight changes to some of the dialogue, for instance. They are changes that I thought might add a little spice to the teasing from the girls, and to Tommy's embarrassment.

Also, I'm experimenting with the type of paragraphing I had been using. I feel that sometimes my paragraphs go on a little too long, so I have separated some of them when appropriate in hopes of making it a tad more readable and easier on the eyes for the reader.

I hope you find these minor changes helpful, and maybe even more enjoyable.

Tommy's Debasement, Chapter 15

Posted: Sat Mar 22, 2025 4:21 pm
by Blondie
Image

Chapter 15: Depantsed Again

The Shuffle

Tommy shuffled awkwardly through his dance steps, his teacher guiding him along with a steady stream of instructions. His tee shirt was tucked into his white briefs, his pants sat bunched up at his ankles, and his classmates were positively eating up the spectacle.

From her spot beside the platform, Sister Ruth was thoroughly enjoying the display. She may have been deriving more pleasure as an observer than when she was the one in control. "Gosh, she's good," she mused, admiring Miss Richards' skill at administering humiliation.

Miss Richards, meanwhile, was basking in her good fortune. She was in total control of the stripping and humiliation of one of her students. It was fantasy turned reality for her, and she was reveling in the moment.

She took her hands off Tommy’s shoulders and stepped in front of him so she could take in his embarrassment.

“One, two, back, three, four, that’s it Tommy, keep moving.”

My, oh, my, would you just look at him!.…his underwear all exposed, trying to dance with his pants all bundled up at his ankles….so ludicrous, it’s laughable….and his cheeks, they’re positively glowing!.…how delectable!.…it’s so tempting just to yank down his undies right now.…patience, Betty, patience, your time will come.…enjoy the moment....well, it IS time to relieve the poor dear of his pants.

Miss Richards clapped her hands together. "You know what, Tommy? I think we need to make this easier for you. Those pants are just getting in your way, aren't they? “Go ahead and take a seat up here," she said, pulling a sturdy wooden chair toward the front of the platform. "Let’s get those pants off so you can move freely.”

Tommy hesitated, but under the watchful eyes of Miss Richards, Sister Ruth, and over seventy classmates who were practically holding their breath in anticipation, he reluctantly sat.

Miss Richards kneeled in front of him, lifting his feet and propping them against her legs. “Now, now, don’t look so nervous. We’re just tidying things up.”

She tugged gently at the cuffs of his pants, but Tommy instinctively dropped his feet to the floor, holding them in place.

Miss Richards looked at Tommy with a slight smile on her face. “Tommy, sweetheart, I would really suggest you be more cooperative. If you keep making this difficult, I might have to get creative. If you consider your position, someone who is about to be prancing around in front of everybody while stripped to his underwear, I think you’ll agree that it is in your best interests to be more cooperative. You do want to keep your underwear on, don't you?”

Tommy's eyes widened as he nodded his head up and down vigorously while quickly stretching his legs out again.

"Okay, then," said Miss Richards.

Sister Ruth chuckled from the sidelines. Oh, Betty, you do have a way about you, don't you? I love it!


Miss Richards resumed her task, slowly sliding the pants down by the cuffs. She slowly backed up as she pulled the pants further and further down. Tommy felt the fabric glide over his shins, the weight of his belt making the process all the more inevitable. He exhaled sharply as the bundled clothing finally slipped off his feet.

“There we go!” Miss Richards chirped, standing up and giving the pants an exaggerated shake before handing them off to Sister Ruth, who accepted them like a prized trophy.

Tommy dropped his feet to the floor.

“Did I say you could put your feet down, Tommy?”

Tommy quickly and obediently extended his legs straight out. Miss Richards took hold of Tommy’s right foot and slowly peeled down his white sock while continuing her monologue.

“I think you’re going to benefit from this experience, Tommy. You’ll probably remember this day for a long time, and you can use it as a reminder that you need to comport yourself properly.”

She had his right sock in her hand and she started pulling off the left one. She was thoroughly enjoying herself as she continued to tease her hapless victim.

“Not only that, I think your dancing will improve. A large part of dancing is losing your inhibitions. Think about it, Tommy, in a few moments you’ll be dancing around in your underwear in front of all of your classmates. That should go a long way towards helping you lose your inhibitions.”

Miss Richards had both socks in her hands. She bundled the two socks together, rolled them into a ball and tossed them underhanded to the grinning Sister Ruth, who caught them with two outstretched hands and added them to her collection.

Let’s see, I’ll have him sit on this chair…….there we go….oh, the poor wretch, he looks miserable.…it’s so fun to tease him, he blushes so….okay, I’ve got him holding his legs straight out, this’ll be easy….just pull these pants off.…take it slowly, Betty.…God, this is fun!.…there they go, you’ve been depantsed, my helpless little victim.…give these to Ruth.…I’ve never seen her grin like that before….she might be enjoying this more than I.…no, that’s not possible.…oh, he put his feet down, let’s get those back up….yes, I’m not quite done with him yet.…let’s get these socks off….I want him barefoot.…just his underwear, he’ll feel more naked, and it’ll be such a lovely sight.…I’ll slip these off really slowly.…draw out the moment.…the poor boy, he’s just hating this….okay, now the other sock.…look at his smooth, slender legs, how adorable….I can’t wait to have him naked, and squirming around in humiliation….easy, Betty, in due time, in due time.…his moment of truth shall come.…toss these to Ruth.…good catch, Sister!….okay, let’s see him dance around in his undies…this should be charming!

Miss Richards clapped her hands together. “Much better! Now, let’s see you try those steps again. Up, up!”

Tommy rose hesitantly as Miss Richards lifted the chair from the platform, leaving him standing barefoot in his tee shirt and underpants. Every eye in the room was locked on him, the audience enraptured by the ongoing spectacle.


Dancing in His Underwear

“Sister Ruth, if you’d be so kind—music, please,” Miss Richards requested of her newfound soul mate..

Once again, the elegant notes of a Strauss waltz filled the gymnasium. Tommy, resigned to his fate, took Miss Richards' right hand in his left while his other hand found its place at her waist. She, in turn, placed her left hand around his back, leading him with the grace and confidence of someone completely in control of the situation.

And so, they danced.

Surprisingly, Tommy was doing better this time—perhaps out of sheer survival instinct. His movements were still clumsy, but at least he was no longer stepping on his teacher’s toes. The memory of his previous missteps and their consequences weighed heavily on him. He had already lost his pants, socks, and shoes—he dreaded to think what might happen if he faltered again.

His classmates, meanwhile, were thoroughly entertained. A memorable sight it was, a boy clad only in his underwear, waltzing earnestly across the gym floor with his beautiful, fully clothed teacher.

Look at the blushing boy, dancing with me in his undies….too precious….my, he’s actually moving a little better.…I’m sure he’s hoping I spare him from removing any more of his clothes….does he really think I’m going to stop now?.…sorry, my little lamb….this is a once in a lifetime opportunity for me.…I’ve got you right where I want you….putty in my hands....before I’m through with you, you’ll be a sight for sore eyes, dancing naked for us….now, let’s see what we can do about this undershirt.


And Then There Were Just the Underpants

When the music ended, Miss Richards stepped back and tilted her head as if assessing his progress. “That was better, Tommy,” she said with exaggerated consideration. “But I still don’t think you’re moving quite as freely as I’d like.”

She paused dramatically. “Do you think we should remove your underwear?”

The room exploded with gasps and laughter while Tommy shook his head demonstratively.

Miss Richards gave a small chuckle. “All right, all right. Let’s try again. Music, please.”

As the music resumed, Miss Richards took a different approach. This time, she lifted Tommy’s hands and placed them gently on her shoulders. Then, with an almost casual air, she rested her own hands on his lower back.

They danced for a few moments before Tommy suddenly felt something—an unmistakable tug at the back of his shirt.

Oh, no!

Miss Richards, ever so methodical, had begun pulling his tee shirt from where it was neatly tucked into his briefs. The girls in the audience tittered as the exposed skin of Tommy’s lower back steadily grew before their eyes, the fabric inching higher.

Tommy’s breath caught as he realized where this was headed. In a matter of moments, I could be dancing in just my underwear. His cheeks burned hotter at the very thought.

Miss Richards, taking her time, rolled the shirt up to his shoulder blades before pausing. Then, smoothly and with seemingly practiced ease, she took Tommy’s hands from her shoulders and raised them high above his head.

Tommy, though utterly mortified, didn’t dare resist. He had learned by now that resistance only prolonged his ordeal.

With a slow, deliberate motion, Miss Richards lifted the shirt higher and higher—over his head, up his arms, and past his hands. For the briefest moment, Tommy instinctively clutched at the fabric as if to hold onto one of the the last shreds of his dignity, but it was no use.

The shirt left his grasp and Tommy watched forlornly as it glided gracefully through the air….straight into the eagerly outstretched hands of the gleeful Sister Ruth.

Let’s put his hands up here on my shoulders.…good, very good….now I can use both hands to pull up his undershirt.…yes, up and out of those underpants.…I wonder what the poor wretch is thinking now.…the anxiety must be overwhelming!….up it goes.…let me roll it up here at the top of his back, it should stay put….good.…let’s get his arms straight up.…perfect….oh, my, look at his face, he’s positively mortified!.…how delightful.…let’s get this shirt up his arms.…upsy daisy.…lovely, just lovely.…their underarms are so cute when they have no hair yet….off it goes.…ha, he’s holding on to it for dear life, does he really think I’m going to let him keep it? I don’t think so, my soon-to-be-naked little pet….that’s it, there we go, I knew he’d see it my way….send this off to Sister Ruth.…good.…would you look at him now, he’s beside himself….I think I’ll make him dance some more before I get to the best part.…make him think about it for a while.…oh, I can’t wait!

There was a buzzing from the crowd as Miss Richards motioned to Tommy to continue dancing with her. Again she had him put his hands on her shoulders, and her hands came to rest on his now naked waist.

“Dance with me, Tommy,” Miss Richards purred, her grin widening as she savored the sight of her flustered partner, his exposed skin only adding to her amusement.

Tommy hesitated, feeling startlingly bare, the cool air from the open windows sending an unwelcome shiver down his spine. Meanwhile, Miss Richards seemed positively radiant, basking in the moment with a warmth that Tommy most certainly did not share.

“Look your partner in the eyes when you dance with her, Tommy.”

His gaze flickered up to meet hers, but it was a challenge to maintain eye contact when his own face was burning with embarrassment while her eyes were dancing with delight.

At one point, while Tommy’s back was facing away from the audience, she teased him by lowering the back of his underpants below his buttocks. Nobody could see his exposed backside, but Tommy’s surprised and horrified reaction undoubtedly pleased Betty Richards.

I’ve got my hands on his bare skin, I’m sure he’s really enjoying that….I’ll make him look me in the eyes….oh, he looks so humiliated….I just love it.…and there’s a certain amount of fear in his eyes.…he’s wondering, “Is she going to take my underpants off?”….well what do you think, silly boy?.…just not yet, though….I want the moment to build up.…maybe I’ll tease him first….I’ll pull this waist band down below his little bum….down they go.…my, his skin is so smooth.…oh, the look of apprehension on his face.…priceless!.…we’ll keep dancing….I’ll let him feel the open air on his bare tushy for a while.


A Devilish Scheme

Let’s see, how should I go about doing the dirty deed?.…hmm, what would be the most humiliating approach?.…what if I let one of the students do it for me?....one of the girls.…yes, even better than doing it myself….he’ll be absolutely mortified….now who should I….I’ve got it!.…Karen seems to be taking quite a bit of pleasure in all of this.…and she had Tommy squirming earlier when they first came in….yes, Karen will be perfect….I think I’ll send him up there in his underpants, and let her and the girls have some devilish fun with him for a while….oh, this is brilliant!

At last, the music came to an end, and Miss Richards gave a satisfied nod. She pulled up the underpants and said, “That was much better, Tommy. You may return to your seat now.”

Relief washed over him—until he remembered where he had to sit.. The thought of climbing the benches and wedging himself between his gleeful tormentors, clad in nothing but his underpants, filled him with dread.

His classmates were still buzzing with excitement as he turned toward the bleachers, with one arm over his chest and the other arm covering the small protrusion in his briefs. He glanced longingly toward Sister Ruth, where his clothes were safely tucked away. But she had a look on her face that seemed to say, “I don’t think so.”

Summoning every ounce of courage he had left, Tommy took a deep breath and began his walk toward the benches.

“Tommy, please keep your hands at your sides" admonished the relentless Miss Richards. "There is no place for modesty in my dance class. Like I said, you need to lose your inhibitions to become a successful dancer.”

A chorus of giggles followed as Tommy reluctantly lowered his arms, fully exposing his underpants, much to the amusement of his classmates. He slowly climbed the steps of the bleachers, his heart pounding as he approached his designated seat.

In a moment he would be sitting there, almost naked, among a group of girls who were salivating at the chance to further his humiliation.

As he approached his seat he glanced up at Karen, who was grinning from ear to ear. He shuddered for the umpteenth time that day.

Tommy's Debasement, Chapter 16

Posted: Sun Mar 23, 2025 6:21 am
by Blondie
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Chapter 16: At the Mercy of a Gaggle of Girls

The Pink Bow

As Tommy navigated the gymnasium stands, his eyes darted around in search of an escape. Spotting a small gap beside one of his friends, he seized the opportunity, motioning for his friend to shift over. Showing compassion, the boy obliged, and Tommy quickly slid into the seat, hoping to avoid the torment awaiting him in his original spot.

Miss Richards, however, was having none of it.

“Tommy, what do you think you’re doing? I told you to return to your seat.”

“Sorry, Miss Richards, I didn’t think it really mattered where I sat,” he answered hesitantly.

Miss Richards raised an eyebrow. “Oh, you didn’t think it mattered? Well, I’ll be happy to show you just how much it matters. Come back down here this instant.”

A heavy silence fell over the gym as Tommy, utterly mortified, began his descent back toward the platform. With every step, his anxiety grew—his underpants were all that stood between him and total humiliation, and the last thing he wanted was to risk losing them. But then, as he reached Miss Richards, he had a different concern.

She was holding something in her hand.

A large, pink bow.

Tommy swallowed hard. He had heard whispers about Miss Richards’ infamous bow—its occasional, dreaded appearances in her class—but had always counted himself lucky that it had never appeared in her dance class.

Until now.

Tommy pictured himself wearing the bow while clad in his underpants (or naked!), which only added to his apprehension.

The giggles from the audience swelled as Miss Richards dangled the bow before him, savoring the moment.

“Tommy, you disobeyed me. I told you to sit in your assigned seat. You know I prefer the seating arrangement to alternate boy and girl, yet you sat next to a boy. Tell me, Tommy, do you think you’re a girl?”

“N-No,” Tommy mumbled, staring down at his bare feet.

“Well, you sat next to a boy, so I think you secretly like the idea of being a girl. It’s your lucky day, Tommy, because I’m going to accommodate and let you wear this pretty girly bow on your head for the rest of the class.” She held up the bow with exaggerated flourish.

He again heard the giggles from the audience as Miss Richards took her time, fastening the oversized bow atop Tommy’s head. Its wide loops framed his face comically, making him look almost like a cartoon character.

Stepping back, Miss Richards placed a finger on her chin, appraising her handiwork with a mischievous glint in her eye. “My, my, don’t you make a darling little girl, Tommy! The bow suits you so well—it even matches those adorable rosy cheeks. Honestly, you’re just missing a cute pair of panties and maybe a little training bra. I’m sure if it comes to that, Sister Ruth would be more than happy to find some for you.”

Tommy’s eyes widened in horror, his entire face burning as the audience roared with delight.

Miss Richards chuckled and gave him a playful swat on the backside. “Now, off you go—back to your proper seat, and behave yourself.”

Oh, he thinks he’s going to weasel out of sitting with the girls, does he? We’ll just see about that….heh, heh, now I get to use one of my favorite little punishments....and wouldn’t you know it—I just happen to have my trusty bow right here in my bag...I didn’t think I’d need it, figuring that stripping the boy naked might be quite enough….but this? Oh, this is just too perfect....a little forced feminization in conjunction with imposed nudity….does it get any better than this?....ah, here he comes….look at the poor dear, shuffling toward me like a frightened little kitten....I’ll bet he thinks I’m about to strip him naked.…oh, just you wait….your time will come, sweetheart.…but first we’re going to have some fun with you....let’s pretty you up a bit, shall we?....clip this bow right….here....perfect!....just enough hair to keep it in place....I hate when I do this to the short-haired boys—it tends to dangle....but this?....this is divine….oh my, would you look at him....he’s blushing more than ever....how delicious!....the bow works its magic every time....and that look on his face when I mentioned the panties and training bra?....priceless!....if only there were time to really sissify him properly….I’d do just that....what a delightful image that would be….ah, but we have other fun and games planned for you, my little lamb....and I’m about to throw you straight to the wolves….okay, I’ll give you a slap on your little butt and send you on your merry way.…oh, how delectable....this just keeps getting better!


The Gaggle of Girls

Tommy, now blushing crimson,, had to make the humiliating trek back to his seat. The ridiculous accessory only added to his disgrace. It weighed almost nothing, yet to Tommy, it might as well have been a brick pressing down on his head.

Averting eye contact, he climbed the bleachers as quickly as possible. As he neared his dreaded destination, his stomach twisted at the sight of the expectant, grinning girls awaiting him. To his dismay, Sally and Cindy seemed even more excited than before. He didn’t know what they were up to, but he knew it couldn't be good. Then he glanced at Karen, and wondered how somebody could be so pretty, yet so mean.

To make matters worse, Karen suddenly giggled before bursting into full-blown laughter at something Sally had whispered in her ear. Tommy swallowed hard. Whatever it was, he knew he wouldn’t like it.

With a strong sense of dread, he reached his original seat. Before he could react, Linda seized the waistband of his last remaining garment and yanked him down onto the bench between herself and Karen. He barely had time to process what had happened before Karen leaned in close, her lips grazing his ear.

"Welcome back, sweetie," she cooed, running her fingers playfully over his bare chest. "Remember, you still owe me a look at your cute little wee-wee.”

Tommy jerked away, brushing her hand aside, only to hear Miss Richards' unmistakable voice ring out.

“Tommy, I don’t want to have to tell you again to keep your hands by your sides. If I have to, I’ll tie them behind your back, believe me, I will.”

Oh, this might turn out even better than I thought. He’s barely sat down, and Karen already has him hot and bothered.

With no choice, Tommy let his hands drop limply to his sides as Miss Richards resumed her lecture on folk dancing. Not that anyone was paying much attention. Every few seconds, another student would sneak a peek at the surreal sight of a nearly-naked boy sitting among a group of fully clothed girls, a bright pink bow perched atop his head.

Tommy, of course, was absolutely mortified. He could do nothing to stop whatever torment the girls had planned for him. And Karen, positively glowing with amusement, wasted no time taking full advantage.

“That bow is just darling, Tammy,” she purred, straightening it on his head with exaggerated care. “Yes, you really do look more like a Tammy now.”

Tommy tensed as Karen’s fingers lazily traced circles on the top of his thigh. With so much more skin exposed, she had a far larger area to work with than she did during recess.

“And such pretty legs, too,” she mused. “Linda, feel Tammy’s legs. They’re so soft and smooth.”

Linda happily obliged, cooing in delight. “Ooh, you’re right! Tammy must’ve shaved them this morning. Nancy, come feel!”

Before Tommy could protest, Nancy had turned around and was running her hands along his calves, giggling with the others. Behind him, Cindy and Sally were practically howling with laughter.

Then he felt a sudden tug at the waistband of his underpants—then a sharp snap as it was released, stinging his lower back.

He spun around just in time to see Sally’s hand retreat, her face alight with mischief, while Cindy burst into fresh giggles. Not to be outdone, Karen and Linda each grabbed the sides of his waistband, yanking it out and letting it snap back into place.

Then Karen smirked and pulled the band out from the front. She started to lean over to look inside.

Tommy tensed, instinctively swatting her hand away.

“What’s the matter, Tammy?” she teased. “Don’t you want to let me have a peek at your little pee-pee? My, aren’t you the bashful one.”

Again she leaned in, and again Tommy warded her off.

It was about that time that there was an occurrence that marked the beginning of the end of Tommy in his clothed state, such as it was. Sally, fully aware of how ticklish her brother was, suddenly launched a two-handed attack on his sides, wiggling her fingers with merciless precision. Tommy practically jumped out of his seat, his body reacting before his brain could stop it. He couldn’t keep from slapping his sister’s hands away, an action that did not go unnoticed by the highly entertained Betty Richards.

She wasted no time pouncing on the opportunity.

“Tommy!” she called, her voice sharp with fake reproach. “I’ve asked you to keep your hands at your sides, but you seem to be having trouble obeying me. Well, if you won’t restrain yourself, I’ll just have to do it for you. Clasp your hands behind your head, elbows straight out to the sides. Sit up straight. And this is your last warning—if you can’t maintain that position, I will relieve you of your underpants. Maybe if I make you sit there stark naked, then you’ll learn to behave. Now do as I say.”

A chorus of delighted giggles filled the air as Tommy, burning hotter than ever, reluctantly obeyed. With trembling hands, he locked his fingers behind his head, his pink bow now even more prominent, his elbows jutting out in humiliation.

The laughter swelled around him as he sat stiffly, fully exposed, feeling more vulnerable than ever. And worse yet, he was quite fearful of the prospect of losing his underpants.

Oh, would you look at him now….a sight for sore eyes….squirming, helpless….his smooth little underarms on display….I just LOVE it!....the girls are about to pounce, I can feel it….he’ll be putty in their hands.

Karen wasted no time taking advantage of the situation. With both hands, she pulled the back of Tommy’s underpants down and tucked them as far as she could under Tommy’s buttocks.

Tommy, wide-eyed and open-mouthed, lifted and gyrated his hips in an effort to restore his modesty (of what little remained!), much to the amusement of the giggling girls. But his underpants remained steadfast, wadded underneath him.

Karen leaned in, her lips barely brushing his ear.

“You heard Miss Richards, Tammy,” she teased. “You’d better sit still, or they’re coming completely off. Then you'll be naked! Completely naked in front of all of us. And I’ll finally get to see your little wee-wee.”

She leaned back and looked down at Tommy’s seat. “Your crack is showing, you naughty, naughty boy.”

The giggles turned to shrieks of laughter.

Tommy, beside himself, looked desperately at Miss Richards, silently pleading for mercy.

But to his horror, she was grinning—and, even worse, making a circle with her thumb and index finger, flashing the unmistakable “okay” sign straight at Karen.

Karen grinned right back and returned the gesture.

Tommy swallowed hard. “Oh God…” he muttered under his breath, utterly defeated.

Oh, that Karen is such a little devil.…it’s just a matter of time now, my little pet.…the girls aren’t about to let you sit still....before you know it, you’ll be surrendering your underpants to them at my command….that is, if they can wait that long.


The Feathers

Then, unbelievably, two large red feathers appeared from somewhere within the crowd. No one but the culprit knew exactly where they had come from, but it didn’t matter. What did matter was that they were making their way toward Tommy, hand by hand, amidst rising giggles and hushed whispers.

Tommy’s stomach knotted as he watched the commotion building to his left. He couldn’t quite see what was causing it at first, but then his heart sank. The feathers were coming straight for him.

When they finally reached Karen, he winced, bracing himself for the inevitable.

But instead of using them herself, Karen smirked and turned, passing them to his sister. “I hope you’re not ticklish, Tammy,” she teased.

Sally’s eyes gleamed with excitement as she accepted the feathers. She had seen them working their way up the stands and had been desperate to get her hands on them. For a brief moment, it had seemed like her hopes would be dashed when Karen intercepted them. But Karen, ever the schemer, had recognized an opportunity.

Being tickled from behind—where Tommy couldn’t see it coming—would only heighten his anxiety. And the fact that his own sister would be wielding one of the feathers? That was just the icing on the cake.

Karen and Sally shared a devious grin before Sally handed the second feather to Cindy. The two girls exchanged a knowing look, both of them practically buzzing with anticipation. But they weren’t about to rush things. No, this needed perfect timing.

So they waited.

A couple of excruciating minutes passed. Then, without warning, the first feather struck.

A faint, teasing tickle traced along the cleft at the top of his exposed buttocks.

Tommy jolted, sucking in a sharp breath as he instinctively retracted his hips, sitting up bolt upright, while the sounds of giggles filled the gym.

Sally, giggling wickedly, continued the torment, twirling the feather in slow, deliberate circles just above the back of Tommy’s underpants, which were still scrunched underneath him.

Tommy squeezed his eyes shut, trying desperately to remain still.

Tommy arched his back as Sally’s feather started rising up his torso. He gritted his teeth, still sitting up straight with his elbows pointing straight out, as he struggled mightily to maintain his position.

Then, before he had a chance to recover, he felt another tickling sensation—this one creeping along his right side. His muscles tensed as Cindy worked her feather in agonizingly slow circles, starting low at his waist and ever-so-gradually moving upward.

Sally, Cindy, and Karen all grinned as they watched their helpless victim squirm, knowing full well that they had him exactly where they wanted him.

Sally and Cindy were having the time of their lives. Tommy’s squirming, his desperate little jerks away from the feather’s touch—every reaction was a victory. Sally especially knew that it would be a matter of moments before Tommy would lose the battle. While they were growing up, more than once she had pinned Tommy down and tickled him, and invariably it ended with her tickling his armpits and him losing control, being forced to yell “Uncle!” And now, with an entire audience and a very eager accomplice, she wasn’t about to let this golden opportunity go to waste.

Tommy, meanwhile, was doing everything in his power not to break. He gritted his teeth and tried to block out the ticklish sensations creeping up his ribs, along his stomach and near his underarms. But it was impossible.

A tiny squeak escaped.

“Oooh, did anybody hear that?” Cindy giggled.

S-st-stop!” he gasped, his body jerking in a frantic attempt to escape the strokes of the feathers.

When Tommy felt the two feathers begin circling each of his nipples, he was on the verge of breaking. He squirmed and fidgeted under their unyielding torment. The girls squealed with giddiness at the scene they were creating. It was a most amusing sight for all, with, of course, the exception of the squirming, near-naked lad.

Sally could sense Tommy weakening by the second. Soon she would go in for the kill. She licked her smiling lips in anticipation as her feather crept its way up toward her goal. She could see that Cindy had the same objective, and again they exchanged mischievous glances. Each of the girls had leaned forward to have the best angle to tease their prey.


Girls Win

It was about the time that Karen had grabbed hold of the front band of Tommy’s underpants that Sally and Cindy looked at each other, nodded, and mouthed the word, “Now!” Simultaneously the two feathers reached their target, and Sally and Cindy, grinning wickedly, feverishly stroked the feathers back and forth across Tommy’s vulnerable armpits.

As expected, Tommy was no match for the relentless, aggressive line of attack. He reached down and pulled Karen’s hand away from his underpants. He elbowed away the two hands controlling the feathers. He pulled up the back of his underpants.

He knew he was in serious trouble.

Miss Richards had been watching with amusement. She was in the midst of explaining a dance step when she stopped in mid-sentence. It was the moment she had been waiting for.

It’s time, my helpless little victim.…you held up longer than I expected….one does fight harder when desperate.…but it’s all for naught, because you’ll soon be bare nekkid….and I’m sure Karen will give you a most exquisite stripping.…oh, this is so exciting!

“Tommy, would you stand up, please?”

Tommy had a strong feeling of foreboding as he reluctantly stood up.

“You know, Tommy, I believe I did warn you about what would happen if you interrupted my class again.”

Tommy stared down at his feet without responding.

“And what was it I said?” she continued.

Tommy mumbled something inaudible. “Speak up, Tommy. What punishment did I promise you if you misbehaved again?”

“Y-you said I’d have to… t-take off my underpants…”

There was giggling all around.

“That’s right, Tommy. You’ve given me no choice but to take your punishment to the next level. It’s time to get you completely…..and totally….nuuude.”

She emphasized the word “nude” with a longer than normal “ooh” sound, with pursed lips and gleaming eyes. Grinning wickedly, Miss Richards paused to take pleasure in her blushing, most apprehensive victim.

“Only I thought it might be a little more interesting—and certainly more shameful for you—if I let one of your female admirers have the honor of pulling down your underpants—and removing them, of course.”

The hapless lad cringed while the rest of Tommy’s giggling classmates, in eager anticipation, postured themselves for the best possible view of what promised to be a very entertaining spectacle.

“Class, do I have any volunteers?”

"Oh, me!” squealed Karen, whose hand was high in the air, waiving back and forth wildly.

As was Cindy's. “Me too!” she pleaded hopefully.

Not surprisingly, several hands had shot up in the air, most of them from the group of girls in Tommy’s vicinity. Tommy’s face presented about six different shades of red.

“My, my,” teased Miss Richards. “You certainly have a lot of admirers, Tommy. And they all seem quite intent on relieving you of your underpants.

She paused for effect

“Let’s see.…Karen, you seem quite enthused, and I’ll bet you’d be quite adept at carrying out Tommy’s punishment. Would you like to divest Tommy of his underpants?”

Karen clapped her hands together. “Yes! Oh, thank you, Miss Richards! I would love to take off Tammy’s-er-Tommy’s underpants for him. That way, he'll be naked." She then leaned her head forward and looked straight at the small protrusion in Tommy's underpants while saying, "And I’ll get a close-up view of his little wee-wee,” she grinned.

The laughter from the students was effusive.

“Thank you, Karen. Tommy, would you please turn and face Karen?”

Oh my, I don’t think I’ve ever felt so.…so stimulated!….I think I’ve made the perfect choice….he’ll be so much more shamed to have young Karen do the.…the unveiling.…I don’t know how he’ll be able to stand it!….I wonder how she’ll go about it?.…will she do a slow, excruciating take-down of his undies, or will she just yank them down for the shock effect?.…either way, the humiliation should be out of this world….then, when she’s done with him.…I’ll give her a few minutes to make the most of his naked shame.…when she’s done I’ll have him come down here and prance around on the dance floor.…to force him to put on a show by dancing naked for us.…that might be the ultimate humiliation.…oh, just the image of that in my head.…his little penis bobbing about while I make him shake his hips.…he’ll have an all-time blush going.…oh, Betty.…I think I’ve died and gone to heaven!


Karen Takes Charge

Tommy slowly, grudgingly turned toward his nemesis. He was at the depths of his humiliation, and his anxiety was turning to outright fear. He was about to be stripped naked in front of all of the seventh and eighth-grade students. On top of that, a girl in the eighth grade class who was thrilled with the prospect would be doing the dirty deed.

Plus, his sister and Cindy were barely an arm’s length away, relishing every moment.

He looked under the stands, wishing he could just slide down and disappear.

The titillated Karen was certainly going to make the most of her extraordinary opportunity. “Tammy, would you please come over here and stand in front of me?”

Tommy stayed put. Karen was not a figure of authority, and he did not feel compelled to obey her. To no one's surprise, Miss Richards intervened.

“Tommy, I’d like you to follow whatever instructions Karen gives you. I have the utmost confidence in her ability to discipline you properly, and I want you to consider anything she says to be coming straight from me. Is that clear?”

Tommy nodded disconsolately.

“Good. Now Karen, I’m giving you complete control. Be aware that I am a firm believer in shame and humiliation as an effective means of punishment. Take your time, and feel free to use any measures you wish if you feel it may enhance Tommy’s humiliation.”

“You can count on me,” replied the grinning Karen.

The beleaguered Tommy had no doubts about the veracity of the young fiend's words.

“Come here, Tammy,” said the newly charged Karen as she took Tommy’s wrist and pulled him in front of her. Tommy stood between Karen’s knees with his hands by his sides. His eyes were at the same level as his adversary. Cindy eagerly plopped into the vacated seat to Karen’s left, while Sally leaned in directly over Karen’s shoulder to obtain a better view.

Everyone in the gymnasium gave the twosome their undivided attention. Many students were standing to get an unobstructed view. The gymnasium was completely silent, as no one wanted to miss any of the exchange between the tormentor and her victim.

Karen would not disappoint them.

“Tammy, I’d like you to look me in the eyes as I speak to you.” Tommy nervously raised his eyes to meet hers, and he could see the expression of absolute merriment on her face. She took Tommy’s hands in each of hers. “Now, Tammy, let’s do this properly. I want you to ask me—very nicely—if I would please take off your little underpanties. And please use my name when you address me.”

Guffaws and giggles rang throughout the gymnasium. Miss Richards and Sister Ruth looked at each other and grinned in admiration. Karen was doing them proud.

Tommy hesitated; he wasn’t quite ready to partake in his new debasement. “W-what?”

“Oh, you heard me,” Karen said sweetly. “Now don't keep me waiting, Tammy," persisted Karen. "I’m already becoming impatient with you. Ask me and ask me very nicely. And everybody better be able to hear you.”

Tommy relented, much to his shame. “Karen, would you p-please take off…my underpants?”

“That’s not what I said, Tammy,” scolded Karen. "I asked you to say underpanties. Just for that, you can call them panties.”

She paused, allowing the ignominious command to sink in.

“Now that I think about it, with that pretty pink bow on your head, your silky-smooth legs, and your smooth underarms, panties is more appropriate anyway. Now let’s try it again. What would you like me to do, Tammy?”

Tommy swallowed hard. Then, in the softest, most miserable voice possible, he muttered, “K-Karen… would you… p-please take off my… p-panties?”

The screams of laughter shook the walls.

Karen grinned from ear to ear.

“Why, yes, Tammy, I would love to take off your panties for you. You know I’ve been waiting all day to see your little wee-wee that everyone is so amused about. But I think you should get permission from Cindy first.”

Karen let go of Tommy’s hands and gently guided him toward Cindy with a nudge on his hip.

“Now stand in front of Cindy, look her in the eyes and ask her very nicely if I can take off your panties for you. And make sure you call her by her name.”


Teased and Tormented by Cindy

There was no turning back for Tommy now. He stood in front of the young girl with whom he was infatuated. He looked up woefully at her twinkling eyes. “Cindy, would it be okay…”

Cindy seized his wrists and tugged him forward, and before Tommy could react, he found himself plopped onto her lap. She wasted no time, reaching down to grab his ankles and pulling him in closer. Ever the eager accomplice, Sally took over, yanking his legs even farther until Tommy had no choice but to throw his arms around Cindy to keep from toppling backward. His face burned as he realized just how snugly his groin was pressed against Cindy’s midsection.

Sally held onto Tommy’s ankles while the giggling Cindy rested her hands at the very tops of Tommy’s thighs. Cindy grinned.

“Oh, how adorable!”

To Tommy’s chagrin, he felt her fingers delve just inside the leg opening of his underpants. Cindy, basking in her newfound position of power, grinned at her submissive subject. She opened with a bombshell.

I hear you have a crush on me, Tommy," Cindy teased, her eyes twinkling.

Tommy’s eyes widened, his face turning an even deeper shade of red. He shot a glance at his grinning sister, silently cursing the moment of weakness when he had confided in her.

"Oh yes," Cindy continued, savoring his discomfort. "Sally tells me everything. She told me how shy you are about your body….how you won’t even go swimming because you don’t want anyone to see you in a bathing suit. Is that true, Tommy? Are you bashful about showing your body to us?"

Tommy clamped his mouth shut, his heart pounding.

"Come on, answer me, Tommy. Are you shy about your body?"

“No…I mean…I don’t know…maybe…please, I…”

Cindy giggled, tilting her head playfully. "I understand if you are, Tommy. I mean, you're thirteen years old, and yet…" She let her eyes drift downward, grinning mischievously. "You've got these pretty little legs…."

Cindy took her right hand and ran her fingers up and down Tommy’s leg before returning her hand to the top of his thigh. This time she ran her hand all the way up Tommy’s thigh and under the leg opening of his underpants. Her fingers protruded all the way through the waistband and came to rest at Tommy's tummy.

The beleaguered lad flinched, and Cindy followed suit with her other hand. She inched her hands toward each other, resting them ever so close to Tommy’s genitals. She smiled at Tommy’s look of anxiety before continuing with her banter.

“You haven’t grown any hair at all on your body. I mean, your skin is silky smooth, like a young girl’s.” Cindy strummed her fingers playfully along Tommy’s midsection. “And I’ve seen your tiny little pee-pee.”

As she said “tiny little pee-pee” she took hold of Tommy’s.…well, his tiny little pee-pee. She jiggled it back and forth with her thumb and her index finger. Tommy nearly jumped out of his underpants at the intrusion.

“So it's perfectly.…gosh, it’s so tiny I could barely find it!……so it’s perfectly understandable that you’d be uncomfortable about anyone seeing your body.”

She let her eyes slowly travel over Tommy, her grin widening with amusement.

“Now here you are, stripped to your underpants in front of all these people, sitting on the lap and at the mercy of a girl you probably want to make a good impression on. Can you appreciate the irony of that, Tommy?”

Tommy couldn’t respond. Cindy had moved her other hand over and now was gently cupping Tommy’s testicles. He fidgeted his hips nervously, unsuccessfully trying to extricate himself from her grasp. He fixated his gaze to a dark opening in the bleachers below.

“Look at me, Tommy.”

When he lifted his gaze, Cindy’s smiled sweetly. "Now, what was it you wanted to ask me?"

Tommy took a deep breath. After a long pause while he tried to gather himself, he blurted out the requisite question. “C-Cindy, would it be okay if Karen took off my und…my p-panties?”

Cindy feigned surprise. “What, you want Karen to strip you completely naked? Tommy, I’m shocked! You’re so self-conscious about your body that you won’t even wear a bathing suit in public, and now you want to put this little wee-wee of yours (she jiggles it again) on display in front of all these people? Well okay, Tommy, if that’s what you want, you have my permission. Let Karen take off your little undies and let everyone laugh while they watch your hairless little pee-pee bobbing around. But first you’d better see if it’s okay with Sally.”

Cindy, grinning derisively, planted a big, wet kiss on Tommy’s lips before placing her hands under his armpits and helping him off her lap.

The wretched Tommy stood transfixed before collecting himself. He looked up at his beaming sister and said, “Sally, is it…is it…is it okay for Karen to take off my p-panties?”

Sally, who was having fits of convulsive laughter throughout Cindy’s taunting, could barely speak, such was her state of hilarity. "Well, sure, my dear little brother, it’s okay with me, if that’s what you really want. But maybe you should check with Linda first.”

Tommy was forced to continue his humiliating charade by asking Linda, then Nancy the same question.

It seemed that they were all in full agreement that Karen should take off Tommy’s underpants.

Re: Tommy's Debasement, Chapter 17

Posted: Sun Mar 23, 2025 7:19 pm
by Blondie
Image

Chapter 17: The Naughty Niece

Facing Karen

Tommy felt a sudden tug on his elbow, and before he knew it, he was face-to-face once again with his nemesis, who had been eagerly awaiting his return.

“Well, well, look who’s back,” Karen cooed, her grin widening. “Tammy, it’s finally showtime! Can you believe it? The moment of truth has arrived. And you know what that means…” She leaned in, eyes gleaming with mischief. “I finally get to see your little wee-wee, in all its little glory.”

Tommy’s breaths became shorter and faster, his pulse racing as the room grew silent in anticipation. Every eye was on them. Karen’s hands rested lightly on his bare waist, her fingers teasingly slipping just beneath the waistband of his underpants. Tommy’s entire body tensed. Her face was flushed with excitement as she met his wide-eyed gaze.

“Oh, don’t look so nervous, Tammy darling,” she teased. “It’s the moment we’ve been waiting for. Isn’t it thrilling? Knowing that everyone here is watching just the two of us? And in just a few moments….well, let’s just say all eyes will be entirely on you. And you'll be naked! Don’t you feel special, Tammy?”

She giggled at his visible panic, drawing out the moment as she began to tug ever so slowly at his waistband. Tommy instinctively grabbed her hands.

“Uh, uh, uh….Tammy, you’re not being very cooperative. Please put your hands above your head.”

Tommy obeyed, clasping his hands behind his head, a position that was now all too familiar to him.

“That’s my good little boy.”

Karen removed her fingers from inside the waistband and took hold of Tommy’s underpants from the bottom, one hand on each side. She slowly, teasingly, started pulling down.


Tommy Makes a Run for It

Tommy, meanwhile, was nearing a breaking point. Bowing to authority, bullying and intimidation, Tommy had so far submitted to the depraved whims of Sister Ruth, Miss Richards and the seventh and eighth grade girls. But as he felt his underpants slowly being lowered, his mind raced as he envisioned the sheer humiliation of standing completely exposed in front of the devilish Karen and the entire seventh and eighth grade students.

Tommy could endure no more. He had to make a break for it.

Summoning every ounce of courage, Tommy sprang into action. He slapped Karen’s hands away, yanking his underpants back up. Without wasting another second, he darted through the stands toward the exit, his heart pounding.

The startled Karen had recovered from her victim’s surprisingly bold move and began pursuing her scantily-clad prey. Sally, Cindy, Nancy and Linda were close behind in pursuit. Tommy, transfixed on his objective, could barely hear the boisterous uproar generated by the highly entertained (albeit somewhat disappointed) students.

He had maneuvered his way through the stands to the gymnasium floor, and though he was being closely pursued by the equally determined girls, he saw a clear path to the exit. But in his haste, Tommy’s foot caught on a speaker cord, slowing him down just enough to allow the persistent Karen to reach out and grab onto the back band of his underpants.

A comical scene ensued—though for Tommy it was quite unnerving—as Tommy reached behind him in a frantic attempt to pry Karen’s tenacious grip loose. Tommy flailed desperately, but Karen wasn’t letting go. Not one to let an opportunity go by, she used both hands to yank Tommy’s underpants down to his ankles, sending the crowd into a new wave of cheers and laughter.

“Nooo!” Tommy squealed, his voice cracking as he fought for his dignity.

Now completely panicked, he froze, afraid that one wrong move would send his underpants sliding right off. He had one hand gripping the waistband for dear life while using the other to push Karen’s head away—because she, in her dogged determination to finally see Tommy’s little penis, tried mightily to peek around his front side.

The other girls had paused momentarily, watching the hilarity unfold. But the sight of their squirming, red-faced prey was too much to resist.

Tommy had just managed to pull his underpants up to his knees when Sally grabbed Tommy’s hand and yanked it away from his waistband while Cindy gave a determined tug downward.

Tommy let out a yelp, and, adding to the hilarity, he began hopping frantically on one foot, then the other, in a ridiculous, flailing attempt to keep his underpants in place.

Nancy and Linda, meanwhile, stood front and center, covering their grinning, wide open mouths with one hand, while pointing at Tommy’s bobbing little penis with the other.

Tommy still managed to keep Karen at bay, but it seemed certain that it would be a matter of seconds before he would succumb to the onslaught. It seemed inevitable. Tommy’s struggle was growing weaker, the girls’ persistence stronger. His fate was all but sealed.

But just when it seemed that Tommy’s last shred of dignity was about to be lost, his salvation—though temporary—came from a very unlikely source.


A Reprieve from Miss Richards

Oh my, Karen is a natural at this.…taking her time, taunting him instead of going straight for the kill….just a wonderful buildup…."All eyes will be entirely on you….and you’ll be naked!”.…that was a nice touch.…I love it!.…the poor boy must be ready to faint from embarrassment.…and fright!.…imagine being in his shoes right now.…or more appropriately, his underpants.…no, I really can’t imagine.…I think I’d die on the spot.…ah, she’s had him put his hands on his head….I think we’re getting close.…here we go….oh, yes, she’s starting to draw them down, ever so teasingly.…oh, this is so much fun!.…there, I can see the top of the crack of his little fanny.…oh, it’ll be so cute to see him squirming around naked.…and the look on Karen’s face, what a delight…she is absolutely thriving in the moment.…if only I had that opportunity when I was her age.…lucky girl, she’ll be thanking me until her dying days.…oh! there he goes! I had a hunch he might try to make an escape.…can you blame him?.…ah, this is amusing.…look at him dashing through the stands in his little underpants.…can they catch him?.…Karen looks positively pissed, the little terror.…oh, he tripped on the cord….here she comes….yep, she’s got him by the waistband….he’s in trouble.…oh! down they go!….hee hee!.…how exciting, he’s almost naked….and the bow in his hair, it’s still firmly in place….oh, this is a riot!.…he won’t let her see the goods….she’s just dying to see his little penis, isn’t she?.…there's really not much there.….but I think she'll like that....more ammunition for her to tease him....oh, look at Linda and Nancy, pointing and laughing.…God, I wish I had this on video.…I’d watch it every time I needed a laugh….or some self-pleasuring.…oh, here come the reinforcements.…he’s in deep doo-doo now.…he’s hanging on for dear life.…the poor boy has no chance against these fiends.…he’ll be buck naked in a matter of seconds.…but I think I’ll put a stop to this.…as enjoyable as this is, I’ll stick to my original plan.…that way, we can prolong the suspense.…it’ll make the stripping scene that much sweeter when we get there.

“Let him go!” shouted the grinning Miss Richards over the commotion.

The girls, very much caught up in their endeavor, either didn’t hear or pretended not to hear their teacher’s command. Cindy had worked Tommy’s underpants off the leg he was hopping on and was hell-bent on finishing the task, which at that point seemed a foregone conclusion.

“I SAID, LET HIM GO!” screamed Miss Richards, with considerably more intensity.

Much to the disenchantment of Karen and her cohorts, the girls reluctantly obeyed their teacher and watched dejectedly as Tommy hurriedly stepped into his underpants, hauled them up while he sprinted the remaining twenty yards to the exit, pushed the door open and disappeared from sight.

Karen was visibly upset. She slumped her shoulders and was on the verge of tears, such was her state of anticipation and stimulation of being so close, then being thwarted in her endeavor to unveil and humiliate the seventh-grade student.


Introducing Carlene

As the dejected girls trudged back to their seats, their teacher’s mood was quite the opposite. Realizing the strong potential of her victim possibly attempting escape—all things considered, she would have been surprised had he not—Miss Richards had a contingency plan.

It so happened that her fifteen-year-old niece would be available (and more than willing, as the perceptive aunt had expected) to lend a hand, if things took an interesting turn. Carlene, a sophomore and star volleyball player of the nearby high school, would be using the gym later that afternoon for practice. She and her teammates were warming up outside, waiting for the dance class to finish.

It was not an act of desperation on Betty Richards’ part to involve her niece in the humiliation of a thirteen-year-old student. In fact, it was a calculated gamble on her part. Miss Richards had known for some time that Carlene had a certain….enthusiasm for situations like these. In fact, a conversation between them just a few weeks before had solidified the teacher’s confidence that her niece shared in her proclivity for inflicting humiliation.

That conversation took place on a sunny afternoon in the park. The two were seated on a bench, enjoying ice cream sundaes, when their serenity was rudely interrupted. Nearby, a young boy of about ten was throwing an absolute fit, wailing at the top of his lungs because his mother had told him it was time to leave. His poor mother tried in vain to calm him down, but the little terror was inconsolable.

Miss Richards had chuckled, shaking her head. “If I were his mother I would take the boy over my knee right here in public and give him a bare-bottomed spanking,” she mused, only half-joking. She glanced at her niece to see her reaction.

Carlene, who had been lazily scooping a spoonful of ice cream, suddenly brightened. “And you wouldn’t be wrong,” she replied, her lips curling into an amused smirk. “Honestly, some boys just need to be knocked down a peg.”

Miss Richards raised a brow, intrigued. “Oh? And what, pray tell, would you do?”

“I would teach the little monster a lesson he wouldn’t soon forget.” Carlene stared at the young lad while her imagination took over.

“Please, go on,” prodded a surprised and very interested Betty Richards.

They had both left their plastic spoons impaled in their ice creams, as they were now consumed with their stimulating conversation.

“Well, there are several things I could do. And they all would be quite effective.”

Again there was a pause. Betty wondered if her niece was toying with her.

“Well, are you going to tell me what you have in mind for this impertinent lad, or do I have to pry it out of you?”

Carlene laughed. “Sorry, Aunt Betty. I had so many thoughts running through my head that I didn’t know where to start. I do like the idea of forcing him over my knee and pulling down his pants—and his underpants—right here in broad daylight. The more spectators the better. But I would take it a step further. While I had him over my knee I would pull off his shoes and socks and then completely strip off his trousers. His underpants could hang at his ankles. Oh, and I would definitely pull his shirt off, just to make sure the shirttail doesn’t get in my way. Plus, that way he’d be almost nude, which would give him something to think about while I’m giving him his spanking and his underpants are precariously dangling at his feet, or maybe even his toes. In fact, I think I’d make sure that they came off one foot.”

Carlene paused to catch her breath. Her aunt stared at her wide-eyed, and was more than a little titillated. She listened intently as Carlene continued.

“He’ll be wondering, ‘Will I get my trousers back? Will my underpants fall completely off, and I'll be naked?’ I mean, he’ll be beside himself with the trepidation and humiliation of it all! And while I’m spanking him I’ll be scolding him and teasing him. ‘This is what happens to naughty little boys,’ I’d say. ‘How shamed you must feel. Everyone is looking at you, and they're staring at your naked little bottom. And I do say, it’s turning quite a pretty shade of pink!’

"And then when I’m finished spanking him, I’ll stand him up, facing me so I can scold him some more. He’ll immediately reach for his underpants, but I wouldn’t let him pull them up right away. I’d draw out his scolding for a spell while he stands there with his underpants at his feet. I’m sure he’d have his hands covering his little penis. I’d say, ‘Have you learned your lesson, young man?’ Of course he would be all red in the face and nod his head—he might be crying like a baby and be unable to speak—and I’d make him tell me out loud that he’s learned his lesson. He will, otherwise he can stand there like that until the sun goes down.

"When he eventually does I’ll say, ‘Good. You can pull up your underpants now, but you’re not getting the rest of your clothes back until we get home. You can think about how you’ve been behaving while you walk home with me in your underpants. And if you give me any more grief, those are coming off too, and you’ll walk home stark naked.’ I’d make him take my hand and we’d walk home at a nice, leisurely pace. Can’t you just picture it, Aunt Betty? Oh, how I’d love to be that brat’s mother for a day….”

"My goodness!" Betty Richards gasped, eyeing her niece with a mix of astonishment and admiration. “Where in the world did you get such a sadistic streak? That boy would have the humiliation of a lifetime! Don’t get me wrong, I love it!”

They both burst into hearty laughter.


Carlene's Fantasies

“Maybe it runs in the family, Aunt Betty,” Carlene said with a playful glint in her eye. “I’ll never forget when you told me about how you used to punish unruly boys by making them wear a pretty bow in their hair. I was only around eleven or twelve at the time, and I was so intrigued by the idea. I went home and imagined being in your shoes....though, I might’ve thought up a few more things than just the bow...” Carlene paused, clearly enjoying her thoughts, though Betty could tell she was hesitating just a bit.

“It’s okay, Carlene, you can tell your Aunt Betty. If it's any help, I think I might have had some of those same thoughts when I was that age, too.”

Carlene smiled and continued. “Well, I had some….some naughty thoughts.”

“Please, go on,” prodded her aunt. “Tell me what you imagined.”

“Well, here's what I imagine. And I've done this quite often. Don’t get me wrong, it's not really bad. But after I put the bow on his head and see how red he is and how much power I have over him.…I tell him I am going to take his punishment a step further. I watch the look of terror on his face when I tell him that he is going to have to spend the day wearing only his underpants. I imagine a slow, excruciating strip as I take my time in doing the dirty deed myself as he stands there shamefaced and humiliated to the max while I peel his clothes off."

Carlene paused and looked at her aunt for a reaction. She took in her wide-eyed, grinning face, which added fuel to her fire. She continued.

"I start with his shirt. I want him bare-chested and feeling his nakedness right away. I pull his shirt tail out of his pants and slowly unbutton it. I see he is wearing an undershirt, which I like, since it gives me another article of clothing to strip him out of."

Betty Richards giggled, which spurred her niece on.

"I toss his shirt aside and pull his undershirt from his pants. I take the bow off so I can get the tee shirt off, and momentarily set the bow aside. 'Raise your arms,' I say. He does so halfheartedly. 'Nice and high,' I command. When he complies I say, 'Good boy,' and I slowly pull his undershirt past his outstretched hands. I replace the bow on his head. I look at his red face, pat him on the chest and kneel down, then meticulously remove his shoes and socks. I look up at him and smile, maintaining eye contact while I undo his belt buckle."

"Oh, Carlene!" exclaimed her aunt. "I'm loving the detail!"

Indeed, Betty Richards' state of arousal was ever increasing as her niece wove her titillating tale.

"I unsnap his trousers and pull down his zipper," continued Carlene, unabated. "I slide down his trousers, exposing his underpants. His underpants are always the little white briefs when I do this—they call them tighty-whities. I think that makes it more embarrassing for him. There is more skin exposed, and I can imagine the outline of his penis in his briefs. And he always a little penis. Again, more embarrassing for him.

"Anyway, I have him lift his legs one at a time while I pull his trousers completely off. I stand back and grin while I look him up and down. Then I tell him to go back to his seat and that if he behaves, then he can have his clothes back at the end of the day. I picture him sitting at his desk, all red-faced, knowing that everyone in his class is staring at him."

"Oh, yes," admired the teacher. "That does paint a very interesting picture, indeed."

Probably encouraged by her aunt's interest, Carlene delved further into her fantasies. "Um...." she said. "I don't know if I'm going too far, but I....well, sometimes I....I don't stop there."

She looked at her aunt, and was heartened by her countenance, and then by her response.

"Oh no, Carlene, you haven't gone too far at all. To the contrary. You have a vivid imagination, and you're just exploring your creativity. By all means, feel free to just let go. It's your Aunt Betty you're talking to."

"Thank you, Aunt Betty. I feel like I can open up to you, and I knew you'd get it. What I was going to say was....well, sometimes when I have these....I guess you can call them fantasies....when I have these fantasies, I....like I say, I want to take it a step further, and....well, I get the boy totally naked."

Again Carlene looked over to her aunt, hoping for her approval. When Carlene took in the knowing grin on her aunt's face, it was all the motivation she needed to carry on.

"I have two different ways I use to get him naked. Do you want to hear both of them?" asked Carlene.

Is the Pope Catholic?

"Please," urged the teacher. "Pray tell."

"Okay, well the first one happens a few minutes after he takes his seat in his underpants. His seat is somewhere in the middle of the room, so everyone has the best chance to see him. I let him sit there for a few minutes, all red-faced and humiliated. I'm giving a lesson, then I pause and casually say, 'Stevie'—there is a boy named Steve that I went to elementary school with. I think he's cute, and he has kind of a baby face. I would love to see this happen to him, so sometimes I use him when I do this.

"Anyway, I say, 'Stevie, I'd like you to put your underpants on top of your desk.' He looks at me all horrified. He doesn't think I really mean it. So I continue to pause the lesson and just stare at him. 'I'm waiting,' I say. So everyone watches as he reaches down, slips off his underpants and puts them on his desk. If he felt a bit humiliated before, well, now he is totally nude, and mortified to the max.

"I let his underpants sit on his desk for a few minutes, so he can look at them right in front of him. Also I think it's a good visual for everybody. Except Stevie, of course. <giggle> He is just praying that I tell him it's okay to put them back on. But instead, I casually walk down his aisle while reading aloud from a textbook. I stop for a few moments when I reach his desk, just to savor the scene. Then I start walking again until I reach the back wall. I turn around and slowly walk back up the aisle. I'm still reading aloud, and as I walk by his desk I nonchalantly gather his underpants from his desk and continue walking. I hear the students giggle and picture the tormented look on Stevie's face. I turn around and smile at naked Stevie. He does not smile back. <giggle> His face is so red, he's fidgeting around, and....well, he's all naked in front of me and all his classmates! I have to say, I get a bit....a bit excited down there...."

The teenager broke off and blushed, prompting her aunt to try to put her at ease.

"It's okay, Carlene," said Miss Richards while putting a hand on her niece's shoulder. "It's quite a normal reaction, and nothing to be ashamed of. I know exactly how you feel. Don't worry, just enjoy yourself while you use your imagination and explore your fantasies. It's quite harmless, and it will bring you a lot of pleasure."

"Thanks, Aunt Betty," said Carlene. "You're so easy to talk to about things like this."

"It's my pleasure, Carlene," answered Betty Richards, quite truthfully.

Carlene paused while gathering her train of thought. "Do you want to hear the second way I get him naked?"

I do believe the Pope is still Catholic.

"Of course, sweetie," answered the teacher. "Don't hold back on my account."

"Okay, well the other one is pretty simple. I strip him while he is still standing there. Even though I told him that I would make him spend the day in his underpants, after I take his pants off, I take him totally by surprise and swiftly pull down his undies. Of course, then I pull them completely off. The shock effect of suddenly being totally naked really adds to it, I think.

"Oh, I forgot to mention....like I said before, he always has a little penis. You might even say a tiny penis. But I forgot to say that he hasn't grown any hair down there yet. I think that adds to his embarrassment, don't you?"

"Yes, absolutely," said Miss Richards. "Of course, it depends on his age. How old is the poor boy in your....your fantasies?"

"I always picture a boy in early high school. About fourteen," answered Carlene.

"Oh, in that case if he's still prepubescent, then he absolutely will feel extra humiliation. Quite a bit, actually," she said with a grin.

"I think so, too. So of course the first thing he does is cover up his hairless little penis with his hands. I say, 'Put your hands on your hips, and keep them there until I say otherwise.' He does so, and then I look down at his little weenie, then back up to his face.

"I usually don't get any further than that. It’s hard to explain, Aunt Betty….but the feeling of power to totally humiliate him, and the picture in my mind of him standing there wearing nothing but a pink bow and blushing crimson….I get a tingly feeling all over."

Betty Richards smiled. Though rather surprised with her niece's revelations, she quite enjoyed them and also felt a new kinship with her.

"I totally understand, Carlene. As much as I enjoy the bow treatment, I've always wondered what it would be like to take matters a little further. And after listening to you I might just have to do that someday."

"Maybe you should, Aunt Betty," laughed Carlene. "And if you do, please don't be shy about telling me all about it."

"It's a deal," answered her aunt.

Little did Betty Richards know that in a few short weeks her opportunity would be handed to her on a silver platter.


A Call for Help From Aunt Betty

Given her previous conversation with Carlene, it was no surprise that Betty Richards had no hesitation about enlisting her niece in Tommy’s ongoing humiliation. So, after she and Sister Ruth finalized their scheme, Betty reached for her phone and dialed Carlene’s number.

“I’m going to be disciplining a thirteen-year-old student of mine this afternoon,” she began coyly. “Let’s just say there’s a good chance it might involve removal of some of his clothing—and I was wondering if you’d be interested in standing by, just in case he makes a run for it.”

Predictably, her niece was more than interested. Betty had to pull the phone away from her ear as Carlene practically shouted her eagerness to be involved from the very start.

“Patience, my dear,” Miss Richards replied. “I promise you’ll be there for the grand finale, no matter what. But for now, I need you as my backup. If he bolts, you may have to overpower him with your size. I think it is possible that you will get your chance for a little one-on-one discipline before we have him stripped completely naked.”

"That sounds awesome, Aunt Betty!" said the titillated Carlene.

Sure enough, when Tommy made his frantic, ill-fated escape attempt, Betty Richards wasted no time. Shooting a knowing wink at Sister Ruth, she retrieved her phone and made the call.

Carlene, who was outside the building doing deep knee bends, snatched up her phone so quickly she answered before it had finished its first ring.

“Aunt Betty?” she asked breathlessly.

“Yes, dear,” Miss Richards replied smoothly, “it looks like our little troublemaker has decided to make a run for it. If you could intercept him and escort him back to the gymnasium, we would all be very grateful.”

Betty Richards smiled to herself, knowing that the person on the other end of the call was quite grateful herself.

“I’m on it!” shouted Carlene excitedly.

“Excellent. The girls have caught up with him, but I’m about to give him a little....reprieve, just for you. Consider it an early birthday present, and a reward for waiting so patiently. Now, if you hurry, you should be able to catch him as he’s coming through the exit. If he gives you any trouble, feel free to use any means necessary to control him. And Carlene, dear—just so you know, he's already stripped to his underpants.”

“YES!” screamed Carlene while ending the call excitedly.

Laughing in delight, she launched into a sprint toward the building, her teammates watching her in bewilderment. As she dashed past an exit door, she pointed a finger at it.

“Watch that door!” she called over her shoulder. “If a boy comes out—don’t let him escape!”

She ran a few more steps, then added gleefully, “Oh, and he’s only wearing underpants!”

Carlene heard the animated reaction and laughed heartily to herself as she breathlessly sped toward the school entrance.

Tommy's Debasement, Chapter 18

Posted: Tue Mar 25, 2025 12:13 am
by Blondie
Image

Chapter 18: Submission to a Volleyball Player

A Short-Lived Escape

Meanwhile, Tommy had mixed emotions as he shoved open the gymnasium door. Relief flooded him—he had escaped, barely, before Karen and her scheming friends could claim his underpants as a trophy.

On the other hand, he wasn’t out of the woods yet. After all, he was in his underpants, and his clothes were inside the gymnasium, a place he had no intention of revisiting any time soon.

Another nagging thought gnawed at him: Why had Miss Richards suddenly ordered the girls to let him go? A rare moment of mercy? Hardly. He had seen firsthand how much she relished his humiliation. No, this was something else.

Still, bigger problems loomed—like finding something—anything—to cover himself. Then it hit him: the old pair of overalls in the cloakroom. He had spotted them earlier that day in the cloakroom during that awful moment when Sister Ruth forced him into the nightgown. Yes, the overalls will do just fine, he thought.

The gymnasium door clicked shut behind him, leaving him alone (or so he thought) in the long, L-shaped hallway. There were only two directions Tommy could go: to the left, which led to an outside door, or to the right, which led to the classrooms.

Wasting no time, he yanked the pink bow from his hair—ripping out a few strands in the process—and flung it against the gymnasium door. Then, with a surge of adrenaline, he bolted right.

Yes! Home free! I did it!

Feeling liberated, he increased the pace of his barefoot gallop. The splat-splat sound of his feet hitting the hard floor resonated throughout the otherwise quiet hallway. His classroom was right around the corner.

But as he rounded the bend, he ran smack dab into a wall of flesh.


An Amazonian Antagonist

“Going somewhere, little boy?” came the voice from about half a foot above his head.

Dazed, Tommy looked up—and up—to see a derisively grinning fifteen-year-old female. The auburn-haired girl smirked down at him, her arms crossed over her chest. Nearly six feet tall, and built like the athlete she was, from Tommy's vantage point Carlene looked absolutely Amazonian. Her volleyball uniform—tight, black spandex shorts and a matching crop top—only made her seem more intimidating.

Tommy took an instinctive step back and stared at her, as he was momentarily mesmerized by her size, her beauty, and mostly by the expanse of exposed skin.

Carlene tilted her head, enjoying his stunned reaction. “Want to take a picture?” she teased.

Snapping out of his trance, Tommy jerked his gaze away and tried to cover the front of his underpants with both hands—an effort that only made Carlene grin wider.

She started walking toward Tommy, holding out her hand. The leery Tommy, still staring at her bare midriff, backed up, matching her step for step.

“Come on,” she said with an outstretched hand. “Miss Richards wants to see you. She’s very disappointed that you ditched her class.”

It was all Tommy needed to hear. With a terrified look on his face, he turned and ran as fast as he could. It was just the reaction Carlene expected—and hoped for.

“I wouldn’t do that if I were you!” she called after him while slowly, confidently walking in his direction.

He dashed past the gym doors and made a beeline for the exit.

“I’m warning you,” she said, still strolling after him, her tone almost sing-song. “You’ll be sorry.”

Tommy, ignoring her, shoved open the door leading outside—and stopped in his tracks.

Waiting just outside, no more than ten feet away, stood a dozen grinning high school girls. Dressed just like Carlene.

For a moment, there was stunned silence.

Then....

“Let’s get him!” shouted one, and they collectively made a move toward the door.

Tommy yelped, spun back inside, and slammed the door shut. It automatically locked from the inside, so he had at least temporarily dodged a bullet.

But he turned around to face the fleshy Carlene, who was still approaching slowly and confidently, her smile widening with every step.

Panicked, Tommy pressed his ear against the door, listening to the girls still laughing right outside. Then he turned, eyes darting between the locked exit and the advancing Carlene.

Unsurprisingly, reacting like a trapped animal, he charged toward his pursuer. Hoping to somehow squeak by her, he faked to her left and veered to her right.

It was child’s play for the athletic Carlene. She grabbed Tommy by the right ankle, and he went sprawling, hands first to the floor.

Tommy scrambled up, and Carlene, toying with him like a cat with a captured mouse, grabbed his ankle just as Tommy started running. Again he fell to the floor.

Tommy tried crawling away, and the giggling Carlene grabbed the back waistband of his underpants. For Tommy, it was the second time in less than five minutes that a girl controlled him by grabbing onto his underpants. His movement forward naturally caused his underpants to be pulled halfway down his buttocks.

His desperation spiked. With a burst of adrenaline, he twisted free and lashed out wildly. Carlene dodged his swings with ease, laughing.

“Feisty, aren’t we?”

She caught his wrists, but Tommy retaliated with a sharp knee to her thigh.

“Fuck! That’s gonna bruise!” Carlene yelped.

The impact momentarily loosened her grip, giving Tommy just enough time to wrench free, hike up his underpants, and bolt toward the classroom.

“Alright, you’ve pissed me off now, you little shit," Carlene growled, shaking her leg.

Within a matter of seconds Carlene closed the gap, wrapped her arms around Tommy’s torso from behind, and pulled him to the ground.

Tommy flailed, kicked, fought—but it was hopeless. Carlene was simply too strong. In short order Tommy found himself on his knees in a scissors lock, his head securely fixed between Carlene’s muscular thighs.

Standing over him, still holding his wrists, Carlene smirked.

“Ready to go back to the gym now?” she asked.

“No! Please, let me go!” came his muffled, desperate response.

Carlene tightened her legs around him.

“Last chance, little boy. Are you ready?”

“No! Let me go!”

It was music to her ears.


Spanked Into Submission

Carlene lowered her knees to the ground, keeping a firm hold on Tommy’s head between her thighs. With slow, deliberate movements, she shifted her weight forward, inching her way down his back while keeping his torso securely trapped. When she reached his mid-back, she settled into a comfortable seated position, her full weight pressing down.

Tommy groaned, his face hovering just above the floor, elbows digging into the hard surface in a desperate attempt to keep from being completely flattened. But his awkward position meant one unfortunate thing—his backside was sticking up prominently, completely at Carlene’s mercy.

He gritted his teeth and pushed weakly at her with one hand, but it was about as effective as trying to move a boulder. Carlene, utterly unfazed, simply grinned. She had him right where she wanted him—utterly trapped, helpless, and at the mercy of her whims.

“Oh, this is too easy,” she mused aloud, licking her lips in anticipation.

Then, without a word, she reached down, hooked her thumbs under the back of Tommy’s waistband, and ever so slowly began tugging his underpants downward.

“No! Please, don’t!” he cried, squirming frantically.

Even though the experience was becoming all too familiar, for Tommy the humiliation effect was no less severe than before, especially with a new person involved.

Tommy’s protests grew louder, his struggles more frantic, but his captor was in complete control. She continued her slow, teasing descent, pulling his underpants lower, inch by agonizing inch, all the way down his thighs, until she reached an impasse with his knees on the floor.

Carlene giggled, thoroughly enjoying her dominance. “Lift up your right knee," she commanded calmly.

Tommy let out a strangled noise, while kicking his feet uselessly against the floor. He made no effort to lift his knee, knowing that would facilitate the descension of his underpants.

Carlene simply reached around Tommy’s back and squeezed his nipple as hard as she could.

"Ow! Stop!" cried Tommy in pain while lifting his knee.

When he did so, Carlene shoved the right portion of his underpants under his knee.

“Now the left one," she directed.

Tommy needed no further prodding, and he lifted his knee while Carlene slid the other side of his underpants to his shin.

“That’s a good boy,” she teased.

She slowly and silently slid his underpants down his leg, then over his heels. She left them scrunched up near his toes, precariously close to coming completely off. She smiled when she heard a muffled yelp from her victim.

Yes! I’ve got him right where I want him….now let’s get these underpants down.…oh, yes, this is just awesome!.…look at him struggle while I pull them down.…he’s just hating this..…so cute, he’s so smooth and white….his little cheeks won’t be white for long.….oh, Aunt Betty, I owe you, BIG time!….talk about a fantasy come true.…I’m getting that tingly feeling again, only it’s better than ever.…this is the real deal, not a fantasy....I'm looking at his naked flesh....I’m think I’m actually getting damp down there, I can’t believe it….okay, let’s get your knee up….oh, he won’t do it willingly.…he’s hanging on to his little undies for dear life..…a pinch on the nipple should do the trick.…yes, there we go.…now the other knee.…excellent…just slide these aaall the way down.…I’ll leave them just over his toes.…give him something else to worry about while he’s getting spanked..…oh, listen to him, he’s positively frightened.…I would be too, if I were you, my little friend.

“Are you ready to find out what happens to naughty boys?” she said, smiling with pleasure.

“No…please…” was pretty much all Tommy could muster at the present stage of his wretched predicament.

“Straighten your legs out.…go on, lay down, completely flat.…all the way down.…that’s it, perfect….now, push your knees into the ground and lift your hips up a little bit.…come on, you can do it….there.…a little more.…excellent, your bottom is sticking up juuuuust right,” she cooed while gently caressing Tommy’s bare bum.

Carlene continued stroking the naked backside in front of her.. "Such cute little white buns.…and so nice and smooth.…since you’ve been so naughty, we’ll warm them up reeeal good for you….we’ll turn your little cheeks nice and rosy, yes we will.”

Carlene rested her hand on her thigh and then sat quietly still, mainly to savor the moment, but also to add to the anguish of her victim.

Tommy’s rapid, heavy breathing betrayed his extreme anxiety.

A full forty-five seconds went by before Carlene leaned over, gently pulled his buttocks slightly apart, then delicately blew into the crevice of her intended target for a few seconds. She leaned back and smiled as Tommy clenched his cheeks together. She waited a few more seconds before deciding the time was right.

Let’s see, I need to reposition him….like he is, his little ass might be a bit too bony.…a good spanking should be on some nice, fleshy skin….let’s lay him down flat, see what that looks like….ah, he’s putty in my hands, doing everything I say now.…that’s better, but let’s stick his butt up just a little bit.…yes, perfect….it’s ready for me now.…my, what a beautiful sight….oh, feel how smooth it is.…it’s so fun to tease him….what must he be thinking right now…can you imagine how nervous, and how humiliated he must feel?.…I can’t wait to tell Aunt Betty all about this wonderful experience….she’ll want to hear all the details, I’m sure.…okay, I think I’ll sit back and take this in for a while.…enjoy it….and make him sweat a little bit.…listen to him breathing so fast.…what a treat….I’ll wait a little longer….it’s so quiet now, except for his breathing.…pretty soon, all hell is going to break loose.…I think I’ll blow into his little butthole.…pull these cheeks apart a bit....and a gentle, loving sensation for him to feel before he gets spanked silly.…oh, look at him tighten up.…this is just delicious!.…okay, I’m ready.…I’ll wait juuust a few more seconds.…the calm before the storm.

The sound of the sudden strike reverberated through the hallway, as Carlene counted ten steady, hard smacks to the left cheek of Tommy’s backside.

Slap! Slap! Slap! Slap! Slap! Slap! Slap! Slap! Slap! Slap!

“That was for not taking my hand when I asked you to.”

She paused and smiled with satisfaction as Tommy squirmed underneath her.

“Keep those hips up!”

Tommy lifted his hips, and Carlene continued.

“And this is for running away from me.”

Slap! Slap! Slap! Slap! Slap! Slap! Slap! Slap! Slap! Slap!

Ten more smacks, this time to the right cheek. Tommy bent his knees and kicked his legs throughout, and somehow still managed to finagle his underpants safely to his shins.

“Ow! Ow!” he screamed.

Tommy struggled with more intensity, much to Carlene’s amusement and stimulation. She giggled as the traumatized skin reddened before her eyes.

But she wasn’t done.

“Hips up!”

Tommy complied and braced himself for another onslaught.

“This is for fighting with me after I caught you.”

Slap! Slap! Slap! Slap! Slap! Slap! Slap! Slap! Slap! Slap!

Again, ten more swats, this time alternating from cheek to cheek. There was only a moment’s hesitation before the next barrage came, in the same fashion, only with more relish.

“And this….this is for the bruise!

Slap! Slap! Slap! Slap! Slap! Slap! Slap! Slap! Slap! Slap!

It felt to Tommy like his backside was on fire.

“Ow! Oh God! Ow! Ow! Oh! Oh! No more! Please!”

Tommy gyrated his hips and kicked his legs wildly.

Carlene was flush in the face, partially from exertion, but more from stimulation.

Oh, I’m loving this!….look at him squirm while I’m spanking him.…and we’re just getting started.…I love the feeling of power….listen to the slapping sounds….it echoes in the hallway….okay, a second dose of ten, this time on the other cheek.…get those hips up, little boy.…that’s it….ah, his cheeks are turning pink.…he’s making noise now, that didn’t take long….he managed to get his underpants to his legs.…I see where his priorities are.…here comes another ten.…I’ll alternate cheeks this time.…oh, they’re getting redder by the second….this is great!.…my hand stings—imagine how HE feels.…okay, these last ten are coming, as hard as I can.…whew!.…that had to hurt….he’s really thrashing about now.…and listen to him....I think I got my point across.…oh, God, that was awesome!

Carlene took a few breaths, and quite satisfied with herself, addressed the whimpering lad as she rose.

“Stand up, little boy, I want to talk to you,” she ordered.

Tommy, keeping his back to Carlene, quickly got to his feet and, while jumping up and down from the pain, he immediately reached down for his underpants.

“Uh-uh-uh!” warned Carlene. She grinned at the amusing scene, and his colorful derriere. “You can leave those right where they are while I’m talking to you. And turn around and face me.”

Forced into subservience, Tommy complied. He wiped a few tears from his eyes and turned around, clutching his privates. Still throbbing from the spanking, and apprehensive about his nudity, Tommy shifted his weight back and forth from foot to foot.

Carlene delighted in the scene and smiled, as Tommy’s blush increased by the second. It was just like her imagined scene that she had related to her Aunt Betty a few weeks before, only exponentially better, since her victim was in the flesh.

She bent at the waist, put her hands on her knees and her face close to his.

“Now here’s what we’re going to do, little boy. You and I are going to march into that gymnasium and report to Miss Richards,” she said while pointing to the door. “You can walk in willingly, or I’ll carry you in there myself. If you choose to do it the hard way, then your underpants are coming off and you’ll be carried in there buck naked.”

Carlene stood up and continued addressing the miserable lad.

“Maybe before that I’ll let my teammates in here so they can have some fun with you first.”

Tommy’s eyes widened at the suggestion, bringing a smile to Carlene’s lips.

“Well, what’s it gonna be, little boy?”

Tommy nodded his head sullenly, but Carlene would not let him off easily.

“I didn’t hear you. Do we need to remove your underpants?”

“No! I mean…I mean, yes…I’ll…I’ll go…”

“Okay then. You can pull up your tighty-whities now.”

Oh, how funny!.…look at him hopping around.…this is hilarious, I’m just loving it!….my hand still stings, but it was sure worth it..…those underpants are staying down….I want to see him squirm some more.…now I’ll have him turn around….oh yes, this is choice.…he’s still bouncing around, and he’s covering his little penis, just like I told Aunt Betty the little boy would do when we talked in the park.…and he’s blushing so much.…well of course he is.…I think I’d just DIE if I were him right now.…I can’t even imagine!


The Dreaded Bow, and a Peek from Carlene

Tommy turned away from Carlene before reaching down and hurriedly yanking up his underpants. The smiling Carlene took Tommy by the hand and led him back down the hallway toward the gymnasium door. The defeated Tommy walked along grudgingly. He gloomily stared at the door as they walked, knowing that once he entered, a most miserable fate awaited him.

“I have a feeling we’re going to make a lot of people very happy, don’t you think so?” asked Carlene.

No answer was forthcoming from Tommy, but that didn’t stop Carlene from continuing her banter as she merrily escorted her captive.

“I wonder what kind of punishment Miss Richards has in store for you for cutting out of her dance class? Hmm, let me take a guess.…do you think it might involve the removal of a certain article of clothing?”

She smiled as she turned and watched Tommy’s face redden.

“Do you think she’ll make you dance around naked in front of the whole class?”

Again she looked down at Tommy, and again she delighted in his increasingly flushing face.

“I’d really like to see that," said the smiling Carlene as she treated herself to the mental image.

They reached the door, and Carlene reached down to pick up the pink bow that Tommy had tossed aside just a few minutes before. She looked at it curiously.

“What have we here?” mused Carlene. “I see my Aunt Betty is up to her old tricks.”

Tommy flinched at the revelation but wasn’t the least bit surprised to learn that the two demons were related.

"Let's get this pretty bow on your pretty little head," she said.

Carlene meticulously fastened the bow to Tommy’s head, then leaned back to admire the effect.

“Oh, how darling!” she exclaimed while tweaking Tommy’s now crimson cheek with her thumb and index finger. “Aren’t you just pretty in pink?”

Chuckling to herself, she started to open the door, then hesitated when she was hit by an impulse. She kneeled to one knee in front of Tommy.

“Before we go in, I simply must see what you’ve been so desperately hiding from me.”

She reached for Tommy’s waistband, and he immediately tried to push her hands away. Carlene grabbed Tommy’s wrists and pulled them toward her.

“Put your hands on my shoulders,” she directed. When he did so, she said, “If you dare interfere with me again, I’ll blister your little buns like never before, and I can guarantee you’ll be walking through that door showing off all four of your rosy cheeks.”

She smiled at Tommy’s now submissive demeanor, and was confident that she could continue unimpeded.

"Please....please don't do this," begged Tommy as Carlene reached for his waistband.

"Oh, it'll be okay, sweetie. I'll just have a little peeky weeky here," she said as she pulled open Tommy’s waistband, leaned forward and peered inside.

The anguished Tommy felt her hair brushing against his stomach and could even feel her breaths on his most private parts. He listened to her giggle as she continued staring into his underpants for what Tommy thought was an inordinate amount of time.

While still holding his underpants open, she looked up and met his eye.

“Now I know your little secret.…your tiny, little hairless secret,” she teased.

She grinned as Tommy looked downward and somehow blushed even brighter. Carlene followed Tommy’s gaze, and they shared one last look before she gently replaced the waistband to his midsection. She gave him a couple of love taps on his bare tummy, then stood up and looked at him with a wicked grin.

“You’ll just die of embarrassment if they all see that, won’t you, little boy?”

With that, she took Tommy’s hand and started to open the door to the gymnasium.

Yes, I’ll take him by the hand and walk him back to my aunt and all of his classmates.…I’m sure they’ll be happy to see him.…oh, look at him blush while I tease him.…especially when I brought up dancing naked.…wouldn’t THAT be fun to watch….I hope Aunt Betty has that on her agenda.…ah, look at the pink bow….he must have taken it off….one of her favorite punishments….now I get the pleasure of pinning it on his pretty little head.…wow, I see what she means….he’s blushing even more while I do this.…oh, this is rich!.…look at him squirming around….the boys must really hate this.…I must say, it looks kinda cute on him.…he has such soft features.…I could make him look like a pretty girl….if I only had some lipstick….and some little panties..…maybe Aunt Betty will let me borrow him for an evening.…I’d really have fun disciplining him….I’d have him prancing around in my little sister’s panties….and her training bra.…what do they call that?.…oh yeah, “petticoat punishment,” I think….I love the idea….he would hate it and he’d look adorable.…and I’d let my little sister join in the fun….she’d be all over it….we’d really have him blushing crimson.…oh, here I go again….I’m letting my dirty little imagination run wild….and I’m getting myself all hot and bothered.…okay, Carlene, back to matters at hand...let's get you inside....wait....one last humiliation for you before we go in....let's check out the merchandise.…he’s been so careful to make sure I don’t see it…sorry, pretty boy, but I’m going to make it happen.…oh, he’s pushing my hands away.…I’ll give him one warning.…touch me again and that last spanking will seem like love taps compared to what you’ll get……not only that, I’ll strip these off and haul you in there butt naked.…yes, I thought you’d see it my way.….get your hands on my shoulders.…that’s it….clear sailing now….oh, he's begging me....he SO doesn't want me to do this....sorry, my little playmate, it's going to happen....here we go….just pull open this elastic band and peek inside….this should be inter….oh!.…it’s so tiny!….look at that little thing!.…and it’s totally hairless!.…it’s like an eight-year-old’s….oh, this is too much!.…poor boy, no wonder he didn’t want me to see it.…and such cute little balls.…like little cherries….he’ll absolutely die of embarrassment if they all see this….oh, Aunt Betty, strip him naked, in front of everybody.…totally naked!....make him dance, and we can all watch his tiny bits jiggle around.…I’m sure he’s just hating this.…I think I’ll keep holding these open and keep staring, just to make him squirm.…it IS a cute little thing….cute as a button.…and not much bigger.…<giggle>....I saw my boyfriend’s once when he was peeing, and his is at least twice as big….look how it’s so small that it’s pointing straight out, not even hanging down….poor little boy.…okay, just a few more seconds.…look, he’s moving his hips around.…he’s really getting antsy….I’m sure he’s thoroughly humiliated by now.…I’ll look up at his face….oh, yes, he’s red as a fire truck.…that’s right, sweetheart, I’ve been staring at your hairless little pee-pee.…oh, he’s looking down there, too….we’ll share one last look.…together.…oh, that was special….he knows I caught him peeking at his own little bits….and his face got even redder.…what a treat this is!....okay, my smooth little friend, let’s go show you off to all your admirers.


Invasion of the Volleyball Players

Just as Carlene was about to push the door to the gymnasium open, she had an inspiration, one that brought a huge grin to her face.

"How would you like to make some more friends before we go inside, sweetie pie?" asked Carlene as she eyed the exit door.

Tommy followed her gaze and immediately comprehended what she had in mind. He shook his head vigorously.

"No! Please!"

"That was a rhetorical question, dear boy. I'm pretty sure you'll find that my teammates will be quite friendly, and very excited to meet you."

She punched a couple of buttons on her cell phone. In a matter of moments the recipient picked up.

"Hey, Carlene!"

"Paula, are you all still out there?"

"Oh yeah, we've been listening at the door. What the hell has been going on in there? I heard a lot of slapping sounds. Was that what we think it was?" asked Paula excitedly.

"It was," responded Carlene with a chuckle. "My little friend here required a little.....a little attitude adjustment. But he's completely under my control now."

She pulled the phone away and addressed Tommy, whose state of misery was quite apparent in his expression.

"Aren't you, little boy?"

Tommy looked downward, and Carlene smiled while putting the phone back to her ear.

"Anyway, how would you all like to join us?"

"YES!" came the boisterous response from the other end.

The laughing Carlene disconnected the call and looked down at Tommy.

"The girls are very anxious to make your acquaintance."

Tommy's Debasement, Chapter 19

Posted: Wed Mar 26, 2025 5:22 am
by Blondie
Image

Chapter 19: Twelve Peeks Inside the Underpants

The Volleyball Players

Carlene straightened the pink bow perched atop Tommy’s head, adjusting it with an almost sisterly touch before stepping back to admire the look. She grinned. Perfect.

“Now, do me a favor,” she said sweetly, “and go let the girls in. I’ll wait right here.”

Tommy, taken aback by the turn of events, stood transfixed. Carlene knew how to move him along. "I'll give you two choices," she said. "You either go let my friends in right this minute, or I'll do it for you—right after I take your underpants off."

That was all the motivation Tommy needed.

Under Carlene’s amused gaze, the underwear-clad teenager trudged the length of the hallway. When he reached the door, he hesitated, gripping the bar-shaped door release.

Recognizing that he was only delaying the inevitable, he pushed the heavy door slightly open. No further exertion was necessary, as eager hands on the other side yanked it open the rest of the way.

A dozen high school girls flooded into the doorway, their laughter unrestrained.

Tommy barely had time to register their delighted faces before the shrieking and excited chatter filled his ears. He stood frozen, crimson-faced, acutely aware of his humiliating state—standing there in nothing but his underpants, with a bright pink bow still perched on his head.

The girls, utterly enchanted by the spectacle, surged forward.

Panic jolted Tommy into action. He instinctively threw both hands over his groin, spun around, and made a hasty retreat down the hallway toward Carlene. He could hear the volleyball players in hot pursuit, their laughter growing louder.

A sudden tug on the waistband of his underpants made his heart nearly stop. With a yelp, he swatted the offending hand away and quickened his pace, breaking into a panicked trot. He didn’t stop until he reached Carlene and stood behind her, ironically using his tormentor as a shield from the onslaught.

Carlene, relishing every second, raised her palms to her giggling teammates, signaling them to hold back.

“Easy, girls,” she laughed. “Don’t worry—you’ll get your chance.”

They'll get their chance? Chance at what??

While Tommy nervously cowered behind her, Carlene reached back and wrapped her fingers around his wrist, giving it a gentle tug.

"Come on now, little boy, don’t be shy,” she teased, pulling a little harder. “Let’s not be rude to our guests."

Tommy resisted for a second, but with another firm tug, he reluctantly stumbled forward, now standing in full view of his grinning audience. His hands were clamped tightly over his crotch, his face burning as the volleyball players took in the sight of the crimson-faced, nearly-naked boy.

One of the girls wasted no time stepping up.

“My name’s Paula,” she said with a friendly smile, extending her hand. “What’s yours?”

There was no response until Carlene nudged the boy not so gently on the shoulder.

“T-Tommy,” he muttered, reluctantly accepting Paula’s handshake with a feeble grip.

Paula beamed. “Nice to meet you, Tommy. That’s a very pretty bow you’ve got in your hair.”

Tommy didn’t respond—he simply lowered his head, his blush deepening to a shade that matched the bow itself.

Paula wasn’t about to let the moment pass. With a mischievous glint in her eye, she reached out and flicked the waistband of his underpants, watching with delight as the elastic snapped lightly against his skin.

“And you look absolutely adorable in your little tighty-whities,” she cooed.

Tommy let out a mortified squeak as he flinched his hips, his grip over his groin tightening. The chorus of giggles around him made it abundantly clear that Tommy's apprehension was fully justified.

Carlene, enjoying herself immensely, decided to up the ante.

"Would you like to see what's inside?" she asked with an innocent smile. “I did.”

Tommy’s head snapped up, his wide eyes darting between Carlene and Paula in pure panic.

Paula gasped dramatically. "Oh, yes!" grinned Paula. "What do you think, Tommy? I'd love to take a peek inside your tighty-whities."

Tommy let out a strangled noise and took an instinctive step back—only to bump right into Carlene, who placed a steadying hand on his shoulder.

"Alright, girls, here's what I'd like to do,” Carlene announced with a mischievous grin. “If you could all form a nice, orderly line, you can all take turns peeking inside his underpants."

The girls giggled excitedly as they hurried into formation, some bouncing on their toes in anticipation. Meanwhile, Tommy, decidedly less enthusiastic, stood frozen in front of Carlene, his wide eyes darting from one grinning girl to the next. His stomach twisted at the horrifying prospect of what they were planning.

Carlene rested a firm but playful hand on his shoulder. “Tommy, I’d really appreciate a little cooperation here,” she said sweetly. “As you can see, your new friends are very eager to get to know you better. Now, be a good boy and put your hands behind your head,” she instructed. “Let’s make sure the girls have easy access to your underpants.”

Tommy slowly, very reluctantly, removed his hands from their protective position and laced them together behind his head.

The girls squealed in delight. Carlene, however, wasn’t quite satisfied.

“Mm-mm,” she tutted, noticing how Tommy’s elbows were still squeezed together, partially shielding his face. “Move your elbows out, please.”

Tommy hesitated.

“More.”

He shifted them slightly outward.

“More.”

He grimaced and spread them a little further.

“More.”

With a defeated sigh, Tommy finally positioned his arms straight out to the sides.

Carlene beamed. “There we go! Perfect! Now you'll be in a nice, submissive posture while you submit to the girls."

Tommy’s face burned as a fresh round of giggles erupted around him. He felt utterly exposed, his whole body tensing in humiliation.

The girls, meanwhile, were practically buzzing with excitement as they were figuratively licking their chops in their increased state of stimulation.


The Twelve Peeks

Carlene clapped her hands together. “Alright, girls! Let’s get this show on the road. Paula, would you like to do the honors?”

Without hesitation, Paula stepped forward, her eyes twinkling with excitement. Tommy, on the other hand, was paralyzed with dread. He swallowed hard as Paula kneeled before him, gazing up at him with a smirk that sent shivers down his spine.

She curled her fingers just under the waistband of his underpants, making sure her cool fingertips brushed his skin. Tommy instinctively flinched, his body betraying his discomfort. Paula, of course, noticed everything.

“Oh my,” she teased, her grin widening. “A little jumpy, aren’t we?”

Tommy stared straight ahead, refusing to acknowledge her playful taunts. But Paula wasn’t about to let him off the hook so easily.

“This is so exciting, don’t you think?” she continued, her fingers lightly tugging at the elastic.

Tommy, of course, was in no mood for conversation, which did not deter the effervescent Paula. "I'll bet you don’t have any hair down there yet, do you?" she asked.

Tommy bit his lip, staying silent. His only response was a small twitch of his hips—an involuntary reaction that Paula found utterly delightful.

She let go of his waistband for a moment and trailed her fingers down one of his calves. "No, I don't think you do. Look at these legs, for example,” she cooed. “So smooth… just like a little girly’s.”

Tommy gave a tiny, embarrassed squirm as she stroked his skin.

Paula giggled. “Aw, how darling!”

Carlene chuckled. “Alright, Paula, I believe you were about to do something?”

“Oh, of course!” Paula chirped, standing up. She was at least half a head taller than her subject. "Okay, time to have a little look-see."

She tilted Tommy’s chin up with two fingers, forcing him to meet her gaze. Tommy’s eyes were full of misery, while Paula’s sparkled with pure mischief.

“Don’t worry, sweetie,” she said, her voice dripping with mock reassurance. “I’ll be gentle. I just want to have a quick little gander down here, then I'll be done with you. No harm, no foul, as they say, right, Tommy?"

How Tommy wished that applied. As he looked down, all he could see was a mass of blonde hair. He was all too aware of a pair of eyes on the other side of that blonde hair, and of what the intentions were of the owner of those eyes. His senses were quite acute at the moment, and the aroma of shampoo permeated his nostrils. He felt a tickling sensation on his tummy, as the hair from the top of the young lady's head brushed against him.

It was only a matter of moments before he felt the front of his underpants being pulled ever so slowly away from his midsection. No less disturbing was the sensation of feeling the breaths from his tormentor throughout the insides of his underpants.

Then came the worst part—the laughter. Soft giggles at first, then a full eruption of delighted shrieks, a sound which seemed to Tommy to go on for a very long time. It was all he could do to maintain his position as he endured the shameful indignity.

Eventually Paula released the waistband with a snap, stepped back and faced the crimson-faced teenager. She bent down slightly and took a pinch of his cheek between her thumb and forefinger.

"Thanks, sweetheart, that was just delightful!"

She patted his bottom, turned around and winked at the girl at the front of the line.

"Next!"

A brunette eagerly stepped forward, extending her hand.

“Hi, Tommy! I’m Katy.”

Tommy, beyond mortified, gave her a quick, lifeless handshake before placing his hands back behind his head.

Katy wasted no time. With a teasing grin, she tugged on the front waistband of his underpants and peered inside. The inevitable giggling ensued. She had put her fingertips of one hand to her mouth while holding open the underpants with the other.

“Oh, this is too good,” she mused. “I simply must have a picture of this.”

Before Tommy could even process what was happening, Katy had darted off to retrieve her phone. When she returned, she gave him a sweet, almost innocent smile.

"Could you please do me a favor, sweetheart, and pull out your underpants for me? I have my hands full here and would really like to get a perfect shot of your cute little bits."

Tommy groaned inwardly but knew there was no point in resisting. His face burned as he reached down, hooked his thumbs in his waistband and pushed open his underpants.

Katy leaned in, her camera aimed right at her target.

"A little more, please," she instructed.

Tommy pushed his thumbs out a little further.

"A little more."

Again he complied.

"That's good, now go down a little bit."

Tommy lowered his thumbs. He didn't look down, but he was quite cognizant of how much exposure this was creating for the photographer, who at this point was deriving considerable pleasure from her role in the boy's humiliation.

“Ah, that’s perfect!” she chirped. “Hold it right there.”

Katy backed up a foot or so to capture the subject matter in a good frame.

"Just give me a moment to set this up. I think I'll use the flash. Oh, I think you moved a little bit. Hold your underpants more open for me. Good. Now down a little bit. More. Down, I said. Yes, just like that. Now I can see your little winkie and your little balls. Don't move, hold it right there. Nice and steady. Yes, that's adorable. I'll get a nice clean shot."

A bright flash. Then another. And another.

Katy beamed as she scrolled through her camera roll. The first two were close-ups at different angles of pre-pubescent male genitalia. The third was a full body shot of a young teenager, clad only in his underpants, holding said underpants open just enough to expose the same previously described genitalia. The pink bow atop the head was a considerable shade lighter than the color of the cheeks of the teenager in the picture.

“Oh, these are fantastic!” she gushed. “Here, Tommy—"Do me a favor and type in your cell number for me. The least I can do to repay you for your troubles is to send you these wonderful pictures."

Tommy, utterly defeated, knew that trying to give a fake number would only make things worse. Reluctantly, he typed it in and handed the phone back.

Katy tapped a few buttons. “Done! Now you can check yourself out anytime you want,” she teased, showing him one of the closeups.

Tommy wanted to sink into the floor.

The photographer clicked off her phone. The grin on her face suggested that she was quite satisfied with her effort. "Thank you so much!" said Katy. "You were a very good subject, and quite accommodating."

Katy turned to her teammates, holding up the phone like a prize. “Alright, ladies… next!”

"Hi Tommy, my name's Heather."

And so it went. One by one, the girls took their turns, each adding her own playful touch—some teasing his underpants with a little tug, others making mock assessments of his prepubescent package, and all of them reveling in his embarrassment.

The laughter and joviality at his great expense is something the poor lad would never forget.

He would certainly remember his experience with Victoria, the last of the girls to participate. Carlene would also remember it well, and quite fondly.

Victoria had finished peeking inside Tommy's underpants. After the requisite smirk and giggle, she started to walk away before stopping herself. She looked up at Carlene, who had been enjoying the proceedings at a position behind Tommy. She had been delighting in the expressions on the faces of her teammates as they took their turns peering inside the underpants.

"Carlene," said Victoria. "We have Katy's pictures of his little penis, but it would be nice to have photo or two of his naked little tushy. Would you mind?" she asked as she held up her phone.

"What a great idea, Vickie," responded Carlene. "Tommy, why don't you turn around and face me while Victoria takes some pictures of your cute little bottom."

Tommy slowly, grudgingly turned until he was facing Carlene, who delighted in his wretched expression. "Good boy, Tommy," she said. "Now stay just as you are and keep those hands behind your head while Victoria gets some pictures of you from behind. Okay, Vickie, you're on."

Victoria, grinning freely, approached her miserable victim. Using both hands, she slipped the back of Tommy's underpants to the bottom of his buttocks. Tommy's genitals remained covered, much to his relief.

"My, oh my, would you look at that!" exclaimed Victoria while the eleven girls behind her roared in wonderment. "Carlene, you must have really disciplined him. His ass cheeks are really red. You did a great job!"

Carlene beamed. "Thank you, I thought so too," she said.

Victoria stepped back and held up her phone.

Click.

"Oh, that should be nice," said Victoria. "The red color of his bum will show up nicely with this new phone."

Click.

"Yes, very nice," confirmed Victoria. "But we need to get a full shot of the backside."

Victoria approached her subject and before Tommy knew what was happening, he felt his underpants being yanked down to his knees, eliciting loud giggling from her teammates.

Meanwhile, from the other side of the beleaguered youth, Carlene had a grin on her face from ear to ear. Between the visual of the mortified Tommy and his audible, high-pitched yelp at his sudden exposure, it was an exquisite moment for her. She looked Tommy up and down, then had another nice moment when the two made eye contact right after she checked him out.

"Thank you, Tommy," teased Carlene. "I'm sure this is very humiliating for you, but I have to tell you that you are bringing me a lot of pleasure right now."

She looked down at Tommy's penis again.

"I mean, this little thing is just so cute!" she said as she moved forward and tweaked Tommy's penis back and forth with her fingers.

"AAGHHH!" shouted the taken aback Tommy. He instinctively reached down and pushed her hand away. Carlene was laughing too hard to reprimand him.

"Okay, Tommy," she laughed. "It's time to take you back to the gymnasium."

Tommy swiftly pulled up his underpants. It was a small and temporary comfort, as he had to know that further humiliation awaited on the other side of the door.

"Girls, would you like to join Tommy and me in the gym?" asked Carlene.

"YES!" was the resounding response.

"Okay, let's go, then. My Aunt Betty and Tommy's classmates are anxious to see us, I'm sure."

She turned toward the door to lead the way, taking Tommy's hand.

"Well, I don't know if they're looking forward to seeing us, but I know they're looking forward to seeing you," she said to Tommy.


A Naked Threat

As they approached the gym doors, a voice piped up from the group. It was Katy, still brimming with excitement.

"Um, Carlene?" she asked, her tone filled with mischief. "Do we have a few more minutes?"

"What did you have in mind, Katy?" asked Carlene with a sparkle in her eyes.

Katy hesitated for a second, savoring the moment as she glanced over at Tommy, whose expression betrayed his apprehension over whatever Katy had in mind.

"Well, um....this has been great....awesome, in fact. But… wouldn’t it be even better if we made him… you know…" she smirked, letting the suspense linger. "If we made him get naked for us?"

Oh please, no!

A wave of excitement swept through the group. The girls giggled and exchanged eager glances. Evidently everyone was fully on board with Katy's suggestion.

Well, almost everyone. The lone male in the group wore an expression that indicated that it would definitely not be awesome for him.

Carlene checked her phone. “Hmm, we should be heading back in…”

But Carlene issued that statement with a perceptible lack of resolve. She looked back at Tommy and used her vivid imagination to picture him in a state of forced nudity, and felt a familiar stimulation in her loins.

"But I think we can squeeze that in," declared Carlene.

Tommy made a strangled sound in the back of his throat, his legs trembling slightly, while the hallway erupted into cheers and laughter.

Carlene raised her hand to calm the chaos. “Alright, alright! If we’re doing this, we need a plan. How should we go about getting him naked? Any ideas?”

In their excitement, the girls were talking over each other. It seemed that many of the girls not only wanted to render Tommy nude, but they had ideas on exactly how they would like the dirty deed to play out.

"Easy, girls, easy!" laughed Carlene. "Let me see a show of hands."

Ten hands sprang up. The two who didn't raise a hand were deep in thought on how they would like the plan of completely baring Tommy to come to fruition.

“Katy, since it was your idea, you go first,” Carlene said. “Tell us—how would you like the stripping scene to unfold? And maybe you also have some idea on what you would like to do with him once he's naked."

Do with me? DO with me??

Katy clasped her hands together like she was giddy with anticipation. “Okay, so here’s what I’m thinking. Let's get him naked, but we take his underpants down slowly—make it a real tantalizing unveiling. Draw it out, really let him feel it. Then—” she turned to the others dramatically “—we make him do a little walk down the hall and back, hands behind his head, of course. We'll make him parade naked for us, and I'll record a video of the whole thing."”

Laughter and claps of approval erupted.

“Oooh, I love that!” Paula chimed in. “I was going to say the same thing—reeeal slow to make him feel every second of it. And yeah, making him walk around naked for us sounds great!"

“Alright, that's two votes for the slow takedown and the walk of shame,” Carlene mused. “Shelly, what about you?”

Shelly cracked her knuckles. “I say we just yank them right off in one go—before he even knows what hit him. If we lift him up, I could do it easily.”

She paused momentarily before adding on.

"Then maybe we can make him play with himself. Or if he needs some help maybe one of us can play with him. I can do that, too. It'd be fun to see him with a cute little boner."

Tommy let out a tiny squeak, and more laughter ensued.

“Wonderful!” Carlene grinned. "I'll take one more. Heather?"

Heather tapped her chin. “I say we make him do it himself. He could do a nice little striptease for us. I have some great dance music on my phone, and after his striptease he could shake his naked booty for us."

The girls howled with laughter at the idea.

Carlene nodded her head, smirking. "Ha! Fantastic idea, Heather. I have a feeling my Aunt Betty might have something similar in mind, so maybe we'll save that for her. But I think we should get him naked right now and go from there. We have two votes for the drawn-out strip, so let's go that way."

Her gaze slid to Tommy, who had been shifting uncomfortably, his face a deep, hopeless red. “Are you ready, Tommy?”

She was well aware that the lad was anything but ready for what was about to transpire. Which of course only served to add to the young lady's enjoyment.

"Yes," Carlene said teasingly, "I can see that you are." She smiled and shivered slightly, such was her state of arousal.

“Okay, who would like to do the honors?”

Every single girl’s hand shot up.

Carlene laughed. “Easy, girls, easy! You can’t all do it.” She scanned the eager faces, then turned to Katy. “Katy, your ‘tantalizing unveiling’ sounds delicious. You get the honor.”

She turned to Tommy, eyes twinkling. “Now, sweetheart, hands stay right where they are while Katy pulls off your undies and gets you nice and naked for us."

Carlene stepped back, joining the group as Katy took center stage. She knelt in front of Tommy, placing her hands on each side of his waistband. She looked up at the trembling boy.

"Here we go, dear boy," she purred. Are you ready?"

That same question had now been posed to Tommy twice in a short amount of time. He was decidedly no more ready at that moment than he was the first time it was asked

“Just think,” she teased, “before long you'll be walking up and down the hall for us—completely naked!"

The room went silent, all eyes focused on Katy’s hands as she gave the waistband a slight tug. Tommy felt the movement, felt the anticipation. He looked down and noticed that Katy had moved to his side, offering his captivated audience an unobstructed view of the sordid proceedings. He clenched his eyes shut, but he could not tune out his other senses. He felt his underpants ever so slowly descending, and the cool air he felt on his bare skin made him fully aware of his exposure.

It was unusually quiet; the loudest sound in the room was his own heavy breathing. He opened his eyes momentarily and saw twelve grinning fifteen-year-old girls who seemed to be spellbound. Most of them had their mouth open, as if awestruck, and all were looking squarely at his ever-increasing exposure below his waist. Tommy closed his eyes again, awaiting his doom.

But the next sound he heard was completely unexpected. And the result would be an abrupt end to the proceedings, much to the relief of one, and to the bitter disappointment of thirteen.

The door to the gymnasium had swung open, and none other than Sister Ruth stood at the threshold. Katy, a bit intimidated by the appearance of the nun, discontinued her undertaking and stepped back to join her colleagues.

Tommy swiftly pulled up his underpants, which had descended enough to afford Sister Ruth a display of his naked backside. She smiled at the spectacle.

"It's time to bring Tommy back inside now," she said to no one in particular.

"Yes, Sister," answered Carlene, who took Tommy by the hand and guided him toward the door. "Follow me, girls," instructed Carlene.

While Sister Ruth held open the door, Carlene and Tommy, followed by the twelve volleyball players, proceeded into the gymnasium.

As the reader surely recognizes, the girls' disappointment and Tommy's sense of relief would prove to be short-lived.

Tommy's Debasement, Chapter 20

Posted: Wed Mar 26, 2025 8:41 pm
by Blondie
Image

Chapter 20: A Sibling Spanking

Confrontation with Miss Richards

The sound of cheering was robust as the tall, athletic high school volleyball player entered the gymnasium hand-in-hand with the slender, red-faced, seventh grade student. One was grinning freely, while the other most certainly was not. Both of them were scantily clad, but only the seventh grader appeared embarrassed by his attire.

Carlene had heard the roar of a crowd many times before, but for Tommy, this was his first-ever standing ovation—and, from his perspective, it was for all the wrong reasons.

To much less fanfare, but not without a certain degree of fascination, twelve female high school students followed the twosome into the gymnasium. They were dressed similarly to the girl holding the hand of the underwear-clad boy, and they carried similar grins on their faces. The first row of the stands was free, so they took their seats there, directly in front of the seventh and eighth grade students. Their eyes twinkling with anticipation as they watched their red-faced “guest of honor” being led toward the center of attention.

As the twosome approached the platform where Miss Richards stood waiting, Tommy instinctively slowed his steps. Carlene felt the resistance and gave his arm a firm tug, shooting him a look that promised trouble if he didn’t keep moving. With a resigned gulp, Tommy picked up his pace, shivering slightly as they reached the front of the platform.

Miss Richards stood tall, hands on her hips, her gaze locked onto the hapless boy in his underpants. Her expression was stern—though Tommy, in his distress, failed to notice the slight smirk forming at the corners of her lips.

“What in heaven’s name were you thinking, young man?” she demanded, her voice ringing through the gym. “Do you honestly believe you can just walk out of my class whenever you feel like it?”

The room was deathly quiet. The students were eagerly absorbing every word of the chastisement, and enjoying the sight of the underwear-clad boy again.

There was no response from the angst-ridden boy below her.

Miss Richards wasn’t about to let him off that easily. “Answer me!” she barked.

“I—I mean, no, ma’am,” Tommy mumbled miserably while staring down at his bare feet.

“No, you can’t!” Miss Richards shot back, sounding convincingly outraged. “I ought to pull you up here, take down your underpants, and give you the spanking you so clearly deserve!”

A fresh wave of laughter erupted from the students.

“Oh, don’t worry, Aunt Betty—I already took care of that,” Carlene chimed in with a mischievous grin, squeezing Tommy’s hand for emphasis. The giggling behind her intensified. Carlene turned to her teammates, sharing in their amusement before looking down at her crimson-cheeked captive with a beaming smile.

“Yes, I’m sure you have,” Miss Richards replied knowingly, a grin of her own creeping onto her face.

She turned her attention back to Tommy, who was desperately using his free hand to cover the slight protuberance in his underpants. She relished his obvious discomfort.

“I’ll deal with you later, young man,” she declared. “I have a very special punishment in store for you. Without spoiling the surprise, let’s just say that before this class is over, you will be providing the entertainment.”

Tommy flushed brighter, and Carlene experienced what she previously described as “that tingly feeling.”

Miss Richards let the moment linger, taking in the sight of the trembling young student before speaking again.

“But first things first,” she said smoothly. “Before your little attempted escape, Karen was in the middle of administering your punishment. And she has been very patient, waiting for you to return.”

Karen, sitting among the students, was already bouncing eagerly in her seat.

“Karen, would you be so kind as to stand up?” Miss Richards gestured toward the eager eighth grader, who wasted no time springing to her feet.

“Carlene,” the dance teacher continued, turning back to her niece, “this is Karen. Would you be a dear and escort our little runaway back up the bleachers? Karen still has some unfinished business with him.”

Carlene’s grin widened. Tommy’s stomach twisted. And the gymnasium filled once again with laughter.


Another Escape Attempt

“My pleasure, Aunt Betty,” Carlene replied with a broad grin. She turned toward Karen, who was practically bouncing with excitement, and with an extra spring in her step, she led her reluctant captive up the stands.

Tommy, on the other hand, was not bouncing with excitement. Dragging his feet, he followed Carlene’s lead, his anxiety spiking as he took in the faces of those awaiting him. His sister Sally was grinning ear to ear. Karen looked absolutely giddy. But it was Cindy—a girl with whom he had an unrequited infatuation with—who sent his stomach plummeting. The way she smirked at him, clearly enjoying his predicament, was too much to bear.

He broke free from the grasp of the unsuspecting Carlene and made the now familiar run toward the exit. But the odds were stacked against him this time.

Carlene hesitated for only a fraction of a second before taking off after him. A natural athlete, she covered the distance with ease, closing the gap in mere moments. She caught her prey well shy of the exit, which by then had already been blocked by three of the volleyball players. Before Tommy could even process his impending doom, he found himself lifted clean off the ground.

The gym erupted with laughter and cheers.

Carlene hoisted him effortlessly over her shoulder, securing him with one strong arm wrapped around the backs of his knees. Tommy, now hanging upside down, flailed wildly in protest. As he desperately tried to reach back and free himself from her grasp, he found himself face to face with Carlene’s bare midriff.

Adding to his consternation—and to the great amusement of the onlookers—her every step caused his face to bounce up and down against her flat stomach, and in turn his lips continuously paid involuntary homage to her exposed bellybutton.

“W-wait! Carlene! L-let me go!” Tommy stammered between the humiliating boing, boing of his lips brushing against her navel.

Carlene grinned and patted his thigh. “Sorry, kiddo. You're in for it, now.”

Now intent on delivering the goods, she trotted back up the stands, the extra bounce in her step ensuring maximum boing-age for her captive. By the time they reached the waiting girls, Tommy was dizzy, breathless, and burning red from both exertion and sheer embarrassment.

Before Tommy could say “extreme mortification” he found himself amid his seventh and eighth grade antagonists. They were very excited to see him, and more than a bit irritated with him. That combination of emotions would lead to regrettable consequences for the ill-fated Tommy.

“Oh, good,” Sally said brightly, clapping her hands. “Lay him right here, over my lap! We’ll make sure he doesn’t try to run away again.”

“My pleasure,” Carlene replied, effortlessly flipping Tommy down onto his sister's waiting lap.

Tommy, however, was not about to surrender quietly. Fueled by desperation, he kicked and twisted, managing to slip free and scramble to his feet.

“You might need to hold him down,” Sally observed dryly. “He’s quite the feisty one right now.”

Karen, Cindy, and Linda instantly moved to grab his arms and legs, but Carlene held up a hand.

“I’ve got this.”

Before Tommy could even think about running, he was once again captured, and he found himself in a familiar position—his head securely trapped between Carlene’s powerful thighs.

Pinned in place, all he could do was let out a muffled groan. He desperately tried prying the clenching thighs open, but to no avail.

Carlene took hold of Tommy’s nipple between her thumbs and forefingers and squeezed as hard as she could. For Tommy, the pain was quite intense.

“OWWWW! Please! Stop!” he screamed.

Carlene smirked. “Are you gonna be a good boy now and not try to run away again?”

“Yes! Ow! Please! Oh! Stop! Stop!”

With a satisfied chuckle, Carlene released him. Tommy, breathing heavily, scrambled upright and clasped his hands over his nipples as a rush of pain swept through his body, as if he was jolted with a wave of electricity.

“Oh! Oh!” he cried as he pressed on his throbbing nipples with the palms of both hands.

Karen clapped her hands together, eyes gleaming. “Alright, now that that’s settled… shall we continue? Sally, I believe Tammy was about to lie on your lap.”

Tommy gulped as everyone else settled in, eagerly anticipating whatever was about to unfold.


Over Sally’s Knees

“Come to Mommy now,” cooed Sally as she patted her lap.

The defeated Tommy let out a long breath and, with great reluctance, draped himself over his sister’s knees. The gym erupted in giggles at the sight of the nearly naked boy stretched out over his sister’s lap like a naughty child about to be disciplined.

“That’s a good boy,” teased Sally, giving his backside a few light, playful pats. She leaned down, her voice adopting a sing-song tone. “Doesn’t this bring back memories, Tommy? Remember how Mommy used to do this when you were a naughty little boy?”

Tommy squeezed his eyes shut, his face burning as the audience hung on Sally’s every word.

“Yes, I’m sure you do,” she continued. “And I’m about to give you a good spanking, just like Mommy used to. Only it’ll be just a liiiiiittle different this time.”

Sally paused and looked about the gymnasium. Her face was beaming, as she clearly was enjoying the attention. She spoke louder as she addressed her spellbound audience.

“You see, our mother used to take Tommy over her lap, just like this. I used to watch, and to tell you the truth I enjoyed it, because he was usually being punished for doing something mean to me. But she always let him leave his pants on, and I always wished that she would pull them down—along with his underpants—and give him a spanking on his bare bum. So much more humiliating for him that way, don’t you think so?”

Sally looked back down at the nervous boy on her lap.

“What do you think, Tommy? Wouldn’t it be much more humiliating to have your underpants pulled down and get a spanking on your bare bottom?”

The only response from Tommy was heavy breathing. Sally looked over at Cindy, who was eagerly taking in the proceedings. She had taken a position just above Tommy’s head, her legs straddling the bench seat, facing the action.

“I’ll leave it up to your…..your heartthrob. What do you think, Cindy, should I pull down Tommy’s underpants and spank his bare booty?”

“Oh, most definitely, Sally,” responded the smiling Cindy. “We need to teach Tommy a lesson, and if you pull down his little underpanties in front of all of us I think he’ll be so embarrassed that he wouldn't dare try to test us again.”

Cindy bent at the waist and faced Tommy. They were nearly touching noses.

“That’s right, Tommy. Sally’s going to pull down your little underpanties and spank your naked little boom-boom, yes she is!” she said while taking hold of Tommy’s profusely blushing cheek and tweaking it back and forth. She looked up at Sally and nodded.

“Be careful not to let me see his little wee-wee yet,” interjected Karen, who was waiting in anticipation for her key role in Tommy’s shame punishment. "I'd like to do the honors myself."

“Don’t worry, Karen,” smiled Sally. “I’m just going to expose his little tushy right now. I’ll let you take care of the really fun part.”

Tommy felt his sister's small fingers inside the back of his waistband. He flinched noticeably, his body becoming more rigid.

“Let’s go back to when you were about six years old, Tommy," said Sally. "Pretend you’re a naughty little boy, and Mommy is carrying out your punishment. Now let’s get these down so Mommy can give your little bum-bum a niiiiiice little paddling.”

Sally calmly drew the back of Tommy’s underpants down to the tops of his thighs, fully exposing his buttocks, much to the merriment of the enthralled audience.

“Well, lookee here!” exclaimed Sally. “My, my, look how red your bottom is!”

Sally looked up at the smiling Carlene while the surrounding students stood wide-eyed and open-mouthed, craning their necks to see the object of everyone’s attention.

“I see you’ve already been punished for your naughtiness. But apparently not enough, since you tried to run away again. I’ll make sure that you don’t entertain any more ideas about trying to get away from us. Let’s see….Cindy, how many spanks do you think our red-cheeked little boy deserves?”

“Hmm….quite a few, I would say. How old is he? Six, right?” The grinning Sally nodded. “How many times did he try to run away? Twice here in the gym, and once during lunch. That’s three. So three times six seems like a fair punishment.”

“Excellent!” agreed Sally. “What’s three times six, Tommy?”

There was nothing but silence.

“No answer? Well, I guess I’ll just have to take these all the way off,” said Sally as she took hold of Tommy’s underpants and feigned like she was going to pull them down. She was reasonably sure that it wouldn’t be necessary, and she was right.

“No! Eighteen!” came the anguished cry.

“Eighteen?” repeated Sally. “You say you want eighteen spanks on your bare bottom? I think we can accommodate that.”

“Shall we have him count?” interrupted Cindy.

“What a great idea!” approved Sally. “Tommy, why don’t you count out loud for Cindy and me while you’re getting your bare bottom spanked. It’ll be fun to have you actively participate. Oh, and for my troubles I'd like you to say, 'Thank you, Sally' after each smack. Okay, ready or not, here we go!”

Sally, flushed with excitement, administered the first slap. It was hard and precise, and the slapping sound resonated throughout the gymnasium. She paused momentarily, waiting for her victim’s response. Hearing nothing, she slapped again, and then again.

“I can’t hear you, Tommy. I guess I’ll have to start over.”

She slapped again, with a little more verve.

“Four!” came the somewhat muffled comeback from Tommy.

“No, I said we were starting over. If you don’t cooperate, I’ll have you completely nude in a heartbeat, and you’ll never see your little underpanties again. Now let’s start over.”

Slap!

“One!” shrieked Tommy.

"You forgot to thank me. Let's start again."

"Oh!"

Slap!

"One! Thank you Sally!"

“Louder!” commanded Sally as she slapped again.

“Two! Thank you Sally!" shouted Tommy as he began wiggling his hips under her attack.

“That’s a good boy,” said Sally, whose soothing voice was in pronounced contrast to the ruthlessness of her next strike.

“Three! Thank you Sally!" cried Tommy as he braced for the next smack.

“Four! Thank you Sally!”

Then another.

“Ow! I mean five! Thank you Sally!” Tommy was squirming noticeably.

“Oh, my, look how much redder your little fanny is getting! And we still have a ways to go! What number are we on, Tommy?”

Slap!

“Six! Oh! Thank you Sally!”

“Good boy, Tommy,” teased Sally as she continued her assault. She alternated from cheek to cheek, being careful not to miss any area of Tommy’s exposed buttocks.

“For a six-year-old, you count very well,” she teased while executing the next stroke.

“Seven! Thank you Sally!” Tommy thrashed about and nearly slid off her knees. She repositioned him before taking dead aim and slapping again.

“Eight! Thank you Sally! Please, no mo…”

But the next one hit authoritatively.

“Oh! Nine! Oh! Thank you Sally!” cried the anguished lad.

“So cute, how you’re shaking your little booty for us, Tommy.”


An Unwelcome Erection

Meanwhile, Cindy crouched down, bringing her face close to the howling Tommy. Both were baring their teeth—Cindy with a mischievous grin and Tommy with a strained grimace.

“What comes after nine, Tommy?” asked Cindy in a sweet, soft voice immediately before she heard the next slap.

“Ten! Thank you! Sally! Oh!”

“Very good!” laughed Cindy. She winked at Sally. “How old were you when you first had a crush on me?” she asked while adjusting the pink bow on his head.

Slap!

“Eleven! Thank you Sally!” bellowed Tommy. His face was as red as a ripe tomato.

“Is that right? And how old were you when you finally stopped wetting the bed?”

Slap!

“Twelve! No! Thank you Sally! Ple…”

“How old were you when you first started playing with your little pee-pee?”

Slap!

“Thirteen! Oh! Thank you Sally! No!”

It was during the fourteenth slap that Cindy reached underneath and between Sally's thighs, and Tommy felt her fingers slide into the front of his underpants, and to his horror, take hold of his penis.

“Four…aah! F-fourteen! Oh! Th-Thank you.....Sally! Oh! Cindy! Please don't!”

Tommy tried to pull away, but Sally, well aware of what was transpiring, held him firmly. She temporarily paused the spanking to allow the moment to play out.

“I can see you’re not as excited as I am, Tommy,” said Cindy. “Your pee-pee is as tiny as ever. Just like a six-year-old.”

Cindy’s giggle was one of many who were witnessing the most unusual spectacle. She then grasped the front waistband of Tommy’s underpants and freed up his genitals by wedging the underpants between Sally’s and Tommy’s thighs. Tommy flinched, and Cindy put her mouth to his ear.

“What’s the matter, Tommy? Don’t you want your little goodies out there where the girl of your dreams can play with them?” she said while lowering her fingers to his testicles. Much to the chagrin of the wide-eyed lad, she began stroking his scrotum.

“Such cute little balls,” she cooed. “And so smooth.”

"Please," begged Tommy softly. "Cindy....please.....no...."

Unrelenting, while continuing to tickle his balls with her fingers, Cindy used her thumb to stroke the underside of Tommy's penis.

"Oh, gosh," said the tormented, squirming lad in a loud whisper.

For Tommy, his situation presented quite the paradox. Though his circumstances were dire and utterly humiliating, there was no getting around the fact that indeed, the girl of his dreams was intimately fondling him. He had never experienced anything close to his present state of physical and emotional arousal, as his (somewhat limited) experience with self-stimulation had never triggered the high degree of sensation that he felt at that moment. Hard as he tried to resist, Tommy felt himself starting to become erect.

“Oh no,” whispered Tommy to himself.

Again he tried to squirm free, but Sally had leaned forward and had one arm pressing down on his back and her other on his buttocks. As a precaution, Carlene had taken hold of his ankles. Tommy wasn’t going anywhere.

“Oh, you naughty boy!” shrieked Cindy when she became aware of Tommy’s elevated state of arousal.

She looked up at Sally and grinned wickedly. “He’s getting a little stiffy!” giggled Cindy.

"Ha! I guess the little pervert enjoys a good spanking," laughed Sally.

"Please! Cindy, no....no more," cried Tommy in a soft, throaty voice.

"But Tommy," said Cindy. "Your voice says no, no, no, but your little boner says yes, yes, yes!"

The giggling Cindy continued toying with Tommy’s boyhood, and he became fully erect, such as it was. She was able to completely envelop Tommy’s maximum size in her petite little hand.

“Is that it?” she laughed.

She let go of Tommy’s penis and put her face close to his. The sadistic girl grinned wider as she took in Tommy’s wretched expression.

“Such a cute wittle boy, yes you are!” she teased while running her fingers upwards along his neck and under his chin.

She nodded to Sally, her cue to resume the spanking.

Slap!

“Ow!” screamed Tommy.

The sudden attack caught him off guard, and he forgot to shout out the number.

“That one didn’t count, Tommy, since you didn’t tell us which one it was,” scolded Sally. “I guess your mind was elsewhere, like on your little stiffy. Now let’s try it again.”

But before he felt the next strike, there was another disconcerting turn of events for Tommy. During his struggles, Sally’s skirt had crept upward, an occurrence that enabled her to corral Tommy’s still-erect little penis between her bare thighs. She gave it a sisterly squeeze while administering another slap to his now crimson buttocks.

“Oh!” cried the beleaguered lad.

“That didn’t count either. How many?”

Slap!

“Ow! Fifteen! Please! No more!”

"Doesn't count. You didn't thank me."

Slap!

"Fifteen! Ohhh! Thank you Sally!"

“That’s more like it,” said Sally.

Tommy’s penis began to shrink, and it escaped from Sally’s clutches. She reached underneath and with her fingers she managed to restore it back between her thighs. Tommy, startled and chagrined by his sister’s intimate contact, let out a high-pitched yelp.

Sally and Cindy exchanged knowing grins while Sally gave her brother another playful squeeze with her thighs. She smiled to herself as she lifted her arm and forcefully brought it down on Tommy’s backside.

Slap!

“Are you going to try to run away from us again, Tommy?”

“Ow! No! Oh! Six….sixTEEN! Thank you Sally!”

Tommy’s penis was well on its way to returning to its flaccid state. Its diminutive size now made it prohibitive for Sally to grasp it with her thighs.

“Do you promise to do everything we say from now on?” she asked while administering yet another robust slap on her inviting target.

“Yes! I.…seventeen! I promise! Thank you Sally! Ohhhh!”

“Do you promise to cooperate with Karen while she pulls down your underpanties so she can finally see your tiny little wee-wee?”

Slap!

“Oh no! Yes! I will! Oh! EighTEEN! Thank you! Sally! Please, no more!”

“Good boy! Now let’s do one more, just to make sure you understand. What are you going to let Karen do?”

"Oh! Let her....please!....oh gosh.....let her see my.....you know....

"Let her see what, Tommy? Your tiny little...."

"Wee-wee! Please, let me go!"

"After you tell me exactly what you're going to let Karen do. Start with what she's going to pull down."

"Oh, gosh," replied Tommy breathlessly. "She's going to....to pull down my underpants and....and....look at my....my tiny little wee-wee!"

The laughter throughout the gymnasium was almost deafening.

"Very good, Tommy!" giggled the boy's fiendish sister while exchanging healthy grins with the eager Karen.

Sally waited for the laughter to subside, then took a deep breath, reared back and slapped her brother's traumatized derriere one last time for good measure, then pushed Tommy off her knees and watched him land in a heap at her feet.

“OW! OW! OW!” screamed Tommy as the pain fully registered.

With tears streaming down his face, he hastily pulled up his underpants while scrambling to his feet. The thoroughly humiliated, crimson-faced boy held his backside while jumping up and down, much to everyone’s amusement.

“Oh! Oh!” he howled, while continuing to rub.

Meanwhile, Karen sat just a couple of feet away, smiling devilishly. Her time had come, and she was positively euphoric, such was her level of delicious anticipation.

Please Ignore

Posted: Sat Mar 29, 2025 6:17 pm
by Blondie
Please ignore. It seems I have to create a post in this spot of the thread in order for the links to the chapters to work properly. This is probably due to the trouble we had with the spammer.