Tommy's Debasement

Stories about boys ending up in compromising situations, preferably naked and embarrassed, as the name suggests.
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Blondie
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Re: Tommy's Debasement

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Samwor2762 wrote: Sat Dec 09, 2023 7:56 am Hi as someone who is a massive fan of your work is there any way I can view all your stories or alot of them currently or will I have to wait while you upload them then in installments on here?

Thank you
Here is a copy & paste of my answer to the same question on a previous post:

I haven't stored them anywhere else online, other than the three (!) sites that went down over the years. There is always the Wayback Machine, but it's kind of a convoluted way to get what you want.

They will all be here when all is said and done, and I can add a link to all of my stories, so they should be organized.

Thanks for the comment.
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Tommy's Debasement, Chapter 3

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Chapter 3: Naked in the Classroom

Nightgown Stripped Off

Tommy walked briskly back to his desk and sat down, his heart hammering against his ribs. He sensed the grinning gaze of Cindy on his left, but kept his eyes firmly fixed on the desktop.

Sister Ruth began the history lesson by lecturing on the years leading up to the Civil War. Tommy, though quite uncomfortable in his predicament, was thankful that his teacher was not focusing on him. He was just getting lulled into a false sense of security when the history lesson took a profoundly negative turn against him.

“So as you can see,” said Sister Ruth, “The slavery issue was a major factor in the ensuing struggle between the North and the South.” She looked up at the clock. “Okay, Tommy, it’s 9:45. As I promised, I’ll let you take off your nightgown now.”

Tommy froze. His breath caught in his throat, and for a moment, he was certain he had misheard her. A stunned silence filled the classroom. His mind scrambled for a way out. “Can... can somebody go down and get my clothes for me?” His voice cracked, betraying his desperation.

Sister Ruth smiled and said, “No, I don’t think so. I told you I’d take your nightgown back at 9:45, and if you behaved, you could have your clothes returned in time for recess. Recess is still forty-five minutes away, so let’s not concern ourselves with your uniform just yet.” She tilted her head, savoring the moment. “But the good news for you is that the ‘shame clothing’ portion of your punishment is decidedly over. So if you’ll kindly hand over your nightgown, we can get on with our history lesson.”

His fellow students looked on in wide-eyed and open-mouthed anticipation. Tommy’s bewilderment had now escalated to a state of anxiety, the likes he had never felt before. “But... but I don’t have anything on under this.” The student’s frightened look only added to his teacher’s enjoyment.

“Yes, I’m well aware of that,” she replied, her eyes twinkling.

A few scattered giggles broke out among the students. Tommy’s gaze darted toward the chalkboard, where his underpants hung mockingly in full view of the class. His stomach churned. “Can I... can I at least put my underpants on first?” His voice was barely above a whisper.

“Mmm... no, I think not.” She turned her head toward the class as if considering their opinion. “I find it rather amusing to have them on display for us. And I think your classmates feel the same way.”

“B-but...”

“No buts about it!” Her expression darkened as she strode toward his desk. “And I am getting sick and tired of your constant insubordination. Now take that nightgown off immediately!”

She loomed over him, hands on her hips, daring him to disobey. But as intimidating as she was, Tommy still couldn’t bear to strip naked in front of the nun and all of his classmates. His whole body went rigid. His fingers dug deeper into the fabric of the nightgown, his knuckles turning white. His mind screamed at him to move, but his body refused.

“Please, Sister Ruth, let me go down and get my clothes,” Tommy begged, his voice cracking with desperation. “I... I’ll even wear this until recess if... if that’s what you want.”

Sister Ruth was secretly enjoying Tommy’s torment, and his desperate pleas. She knew she would have him naked in a matter of moments, but prolonging the buildup to his inevitable disrobing only enhanced her stimulation, much analogous to foreplay before intercourse. She continued to feign anger. “I’ll give you to the count of five to slip off your nightgown and hand it to me. One...” Her voice was measured and slow, dragging out each number just long enough to make him squirm.

“Two...”

His hands clutched at the nightgown, fingers trembling. Around him, his classmates sat wide-eyed in anticipation. Cindy had a smirk on her face, while a few others exchanged wide-eyed glances, unbelieving in what was transpiring before their eyes. Tommy’s legs pressed together. He hunched forward slightly, his eyes darting across the room.

“Oh, please, Sister...” Tommy whispered, a last, desperate plea.

“Threeeeee...” She conjured up an image of her humiliated victim, squirming naked at his desk, and she felt a stirring in her loins, such was her state of titillation.

“Fooooour...”

Tommy’s hands twitched toward the hem, but he couldn’t do it. His body refused. Sister Ruth couldn’t contain the slight smile that appeared on the corners of her mouth. She knew Tommy's nakedness was imminent. A ripple of excitement passed through the room, and Tommy was visibly shaking, his whole body tense with dread.

“And... five! That does it, Tommy,” she declared, stepping forward purposefully. “Let’s get that nightgown off. And you’ll be sorry you disobeyed me.”

Tommy flinched as she moved behind his chair. Before he could react, she reached down and seized the hem of his nightgown, grasping the fabric from both sides near his legs.

“Lift your bottom!” she ordered. He didn’t move. The weight of the moment rendered him virtually paralyzed. Her tone hardened. “Now!”

While his classmates leaned in, eyes locked on the unfolding spectacle, Tommy, with a barely perceptible shift, lifted himself just enough for her to pull the fabric free. A gasp echoed through the room while the nightgown slid under him and began its ascent. Tommy hunched forward, his arms clamping to his sides in a frantic attempt to preserve whatever dignity he had left.

“Arms up!” Sister Ruth instructed. Somehow, almost involuntarily, Tommy obeyed. His arms lifted, and in one swift motion, the nightgown was gone. Sister Ruth turned and strolled back to her desk, casually tossing the nightie into an open drawer before snapping it shut with a sharp kick of her foot.

And just like that, Tommy—living out any student’s worst nightmare—was sitting at his desk in front of his entire class, completely and totally nude.

The classroom buzzed with disbelief. Some students gawked openly, while others covered their mouths, whispering behind their hands. Cindy’s smirk widened, her eyes sparkling with amusement. Tommy, reeling from the horror of the moment, instinctively hunched forward, his legs locked tightly together, and his hands firmly cupped over his genitals, frenetically struggling to shield himself from their relentless gazes.

Sister Ruth turned back to him, her expression calm, controlled. But there was no mistaking the glint of satisfaction in her eyes. She took her time walking back to his desk, savoring every second. Stopping beside him, she looked down at her quivering student. She trembled slightly, as a wave of pleasure swept through her being. A wicked smile formed on her lips. Time seemed to stand still for her as she continued to luxuriate in the wonderful humiliation scene she had created—a scene she knew she would be able to draw on for pleasure for many moons to come.

“Well,” she said, “this is certainly a captivating scenario, isn’t it, Tommy?” She let the words linger, relishing the sight of her wretched victim squirming beneath her gaze. Slowly, she looked up, taking in the sea of eager, grinning faces. She smiled as she addressed the class.

“I have a feeling this will be one of those once-in-a-lifetime classroom moments—something you’ll all be talking about for years to come. Wouldn’t you agree?” Many in the room nodded their heads animatedly in agreement, while every pair of eyes remained transfixed on the squirming, naked boy.

Sister Ruth, relentless in her torment, turned her gaze back to Tommy and smirked. "Tommy, you do realize that no matter what happens for the rest of the school year—this is what everyone will remember most?" She gestured toward his exposed, trembling form, letting the weight of her words settle over him. Tommy squeezed his eyes shut, his entire body tensing. He wished, more than anything, that he could simply disappear.

But the evil nun pressed on. “I’d like you to sit up straight, Tommy. I’ve told you before how important good posture is.” Tommy stiffened, pressing his back against the hard wooden chair, but his hands remained firmly clutched over his privates. Every muscle in his body locked as he struggled to process the overwhelming humiliation. “Now, kindly fold your hands on top of your desk,” Sister Ruth commanded.

A fresh wave of dread crashed over him. His fingers twitched, but they refused to move. His breathing grew shallow as he stole a furtive glance to his left—only to meet Cindy’s grinning gaze. Tommy’s face burned even hotter as she let out a giggle while unabashedly looking him over with amusement. Around the room, quiet titters swelled into barely contained laughter.

Swallowing hard, Tommy clenched his trembling knees together. He fought against every instinct to resist—then he pushed his penis between his legs as best he could before peeling his hands away and placing them on the desk. His legs shot upward, his knees pressing against the underside of the desk. He curled his toes, the tips barely touching the floor, as he fought to shield himself in any way possible.

He made the mistake of glancing at Cindy again. She had shifted, craning her neck in a shameless attempt to peek between his legs. Tommy gasped, jerking his hips to the right—only to lock eyes with Laura. She, too, was grinning, her gaze focused downward with open amusement. There was no escape, no position that would save him.

Sister Ruth took in the scene, her expression one of supreme satisfaction. “You’ll keep your hands above your desk at all times,” she said. With that she turned and swaggered back to her desk, her face flushed with pleasure.

The murmurs of the students had not yet died down when she faced the class again, her gaze instantly landing on the stunned, trembling student. A smile crossed her lips while addressing the class. "Now, where were we before that nude—er, rude interruption?" Laughter rolled through the room. "Oh, yes, the events leading up to the conflict between the North and the South..."

Tommy squeezed his eyes shut, his breath shallow. He could hear the whispers, and could sense his fellow students angling for a better view. No matter how much he wished otherwise, there was no waking up from his nightmare.

Oh, what a glorious morning it’s been... and it’s about to get better... my two favorite fantasies, petticoat punishment and a forced public stripping of one of my students... and they’re both finally coming to fruition today... my heavens, I can’t believe my good fortune... yes, my little plaything, I’m about to drop the bombshell on you... you’re about to surrender your nightgown, and experience the humiliation of all humiliations: enforced public nudity... you’ll be sitting there, stark naked and squirming in shame and panic... my, the anticipation is delicious!... oh, he looks puzzled... he doesn’t quite understand yet... wait, it will sink in... there it is... the look of disbelief, horror and panic, all in one... that’s right, my poor unfortunate, you’re about to become a victim of my lifelong fantasy... aren’t you the lucky one... look at the students, they can’t believe it either... but I get the distinct impression they want it to happen... especially Cindy... look at her, she’s almost salivating... the little devil... and Sally... such an evil grin she has right now... just hoping the dirty deed is done... yes, sweetie, you’re about to see your brother in all his red-faced glory... he’s being defiant, he won’t take it off... I can’t say I blame him... I’ll give him to the count of five, just to draw out the suspense... then I might have to take matters into my own hands... oh, this is so stimulating!... look at him cowering while I count... he can’t believe what’s about to happen to him... five!... okay, that’s it, I’ll pull it off myself, that'll be fun... here we go, pull this up... get your bottom up... that’s it, now pull this up your torso... my, look how smooth and white he his... and slender... how delectable!... control yourself, Ruth... almost home, my little smoothie... just get those arms up... excellent, now up and off, and... voilà!...we now have a naked student in our midst... oh my goodness, just look at him... he’s beside himself... frantically squirming around... covering his privates for dear life... what a moment this is... absolutely breathtaking... even better than I fantasized all these years... I’ll savor this vision forever... not to mention the many hours of self-pleasure it will provide... little does he know what a stimulating experience he’s affording me... of course, he doesn’t care about me right now... he's naked, and in a frenzy... so delicious!... okay, let’s get him sitting up straight... hands on the desk, no more covering up... look at Cindy, trying to sneak a peek... and Laura, too... don’t worry girls, I’ll give you your chance... the humiliation is just beginning.

Take the nightgown off?! I can't do that! I’m naked underneath!... surely she can’t be serious... oh, she is!... no, she can’t do this!... I can’t take this off!... she’s counting to five... I just can’t do it... uh-oh, she’s really mad... no!... she’s lifting it up!... they can see my butt!... please stop!... she’s pulling it off!... no!... it’s gone!... it can’t be!... oh!... oh!... I’m naked!... I’m actually naked!... oh, God!... oh, God!... oh, God!... I’m completely naked!... in front of everybody!... this can’t be happening!... it’s a nightmare!... but it’s not!... oh! oh!... I’m really naked!... gotta keep covered up... oh!... I can’t let anybody see... it’s so small, and I have no hair... no hair anywhere... oh, God!... and the girls... they’re all laughing... I’m naked!... oh no, Sally!... and Cindy!... I’ll never get Cindy to like me now... listen to her giggle... oh, God!... I’m totally naked!... Sister Ruth wants me to fold my hands on the desk... oh, please!... look at Cindy grinning at me... my face is so hot... never been so hot... I must be bright red... oh, help!... I’ll hide my dick between my legs... hands on the desk... here goes... oh, God... Cindy’s trying to see... can’t let anybody see... I’ll turn away from her... no, Laura’s trying to see, too... oh, look at her grinning... and Sister Ruth... why is she just standing there smiling at me?... oh, I want to cry... but that would make it worse... oh, God, I’m naked!

Sister Ruth continued her history lesson, her voice a steady drone in the background. But Tommy absorbed none of it. His mind was consumed with the sheer torment of his situation. He shifted uncomfortably in his chair, hyper-aware of the cool air against his exposed skin and the many pairs of eyes shamelessly drinking in his humiliation, ogling his every move and desperate attempts to shield himself.

His classmates weren’t faring much better in their attentiveness. The sheer absurdity of the moment—one of their own, utterly bare before them—was far more captivating than any lesson on the Civil War.

Remarkably, Tommy's plight was about to worsen. A simple instruction from Sister Ruth would send him further down his already steep spiral. "Class, I’d like you to open your history books to page one hundred and twelve," she said.

At the sounds of desktops opening and books shuffling, Tommy hesitated before lifting his own desktop. He knew every movement he made was being watched, every motion another opportunity for humiliation. But he had more immediate concerns—his history book wasn’t there. Heart pounding, he dug through his desk again, hands trembling. No, no, no... And then it hit him—he’d left it at home. He could still picture it lying untouched beside the toaster as he rushed out the door. "Oh, no," he whispered. In desperation, he grabbed his math book, flipping it open in a shaky attempt at deception. Maybe, just maybe, Sister Ruth wouldn’t notice.

That hope lasted all of five seconds. "Tommy, that doesn't look like your history book," came the dreaded words from Sister Ruth. "Did you not hear me, or are you intentionally disobeying me?”

“I-I-I...” Tommy stammered, his throat dry. “I left my history book at home.” A murmur of amusement spread through the class. Tommy shrank further in his seat.

Sister Ruth let out a slow, dramatic sigh, shaking her head as though deeply disappointed. “You what?” she asked with feigned incredulity. “You’re not having a very good morning, are you, Tommy?” She smiled to herself at what could have been the biggest understatement of the century.

“So let me get this straight,” she continued, tapping her nails against her desk as she spoke. “You already are being shamed by having to sit there stark naked in front of all your classmates, supposedly learning a very important lesson about consequences. And now, on top of that, you forgot your history book?” Tommy’s face flamed as she went on. “And then... instead of owning up to it, you tried to trick me? You actually thought you could sit there, with all your classmates watching, and deceive me?” Tommy wished he could sink into the floor.

Sister Ruth leaned back, folding her arms. “I would have thought someone in your position would know better than to try a stunt like that.” She let the moment hang, stretching out the suspense. Then, with slow deliberation, she pointed to the front of the room. “Come up here right now, young man.”

The class fell into a hush. The excitement in the air was electric.

And for Tommy, his nightmare was only beginning.
Last edited by Blondie on Mon Oct 13, 2025 8:22 pm, edited 5 times in total.
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Tommy's Debasement, Chapter 4

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Chapter 4 : Exposed to His Upskirt Victim

Put on Naked Display

“Come up her right now, young man,” she demanded. Tommy froze in his seat, as the thought of walking to the front of the room in his naked state was more than he could handle. “Now!” Sister Ruth raised her voice and pointed to the floor in front of her feet. Tommy, frightened by his teacher’s tone, jumped out of his seat and shuffled toward the front of the room, both hands cupped firmly over his genitals.

The class looked on in a state of awe and amusement at the extraordinary scene. They couldn’t hold back their laughter, and their teacher did nothing to discourage them. In fact, she seemed to egg them on, knowing that their obvious enjoyment over Tommy's shame only added to the humiliation effect that she had such a passion for.

Tommy cowered before his teacher, looking straight down at the floor, his hands over his crotch. He knew that Cindy was only a couple of feet behind him. He shivered slightly as he considered the display he was being forced to put on.

Sister Ruth stood and observed for a moment, thoroughly enjoying the spectacle. “Tommy, Tommy, Tommy,” she scolded. “No matter how much I try to discipline you, you still act like a naughty little boy. I guess we’ll have to take your punishment a step further. You can start by getting your hands away from your privates. That is a disgusting habit, and I’ll not allow it in my classroom.”

To Tommy’s horror, she took hold of his wrists and with both hands she pried them apart. Initially he resisted, but then submitted to his teacher's unrelenting pressure. She then took hold of his hands and clasped them behind his head, while taking his elbows and pushing them straight out to the sides. Tommy clenched his eyes shut as he tried desperately to shut out the world around him.

“Open your eyes, Tommy. I want you to experience the full effects of your shame punishment.” When Tommy opened his eyes, he saw that his teacher had taken a step backward and was looking him up and down with a devilish grin on her face. His cheeks were burning like they had never burned before. Sister Ruth took notice of Tommy’s crimson face.

“Oh, you’re really blushing now, aren’t you, Tommy? I think I may have finally gotten through to you. I might have to keep you naked for the rest of the day, and then maybe you’ll learn your lesson. Would you like me to do that?” The teary-eyed Tommy shook his head vigorously from side to side. “Well, we’ll just have to see about that. I have to admit, I’m finding your... your unclothed, humiliating condition highly entertaining. And judging by the looks on the faces of your classmates, your naked shame is providing considerable amusement for all of us.

"For now, you can stand up here just as you are and think about your behavior. In the meantime, I’d like to get on with our history lesson, as we’ve had far too many disruptions today already.”

Tommy’s face contorted in anguish at the notion of remaining naked throughout the school day. He heard the giggling behind him and stole a quick glance to his right. A couple of girls on the end, including Laura, were craning their necks, trying to catch a glimpse of his genitals. Some of the girls in the class had never seen a penis before, and their curiosity only added to their fascination of what was transpiring before them. Tommy turned his body ever so slightly away from them, trying desperately to shield himself from their prying eyes.

None of which was lost on Sister Ruth, who pounced on the moment. She called on Laura, figuring justice would be served by allowing Tommy’s “upskirt” victim to partake in his humiliation. “Laura, would you like to come up to the front of the class and read aloud from your history book?” Sister Ruth smiled to herself upon noticing Tommy's wide eyes and open mouth.

“Yes, Sister,” Laura beamed as she grabbed her book and bounded to the front of the room.

Before she reached Tommy, the lad instinctively lowered his hands to cover his genitals, bringing an immediate chastisement from his teacher. “Tommy!” she yelled. “What did I tell you about touching yourself down there! Now get your hands behind your head this instant!” Tommy looked up at the grinning, expectant Laura and hesitated. “Okay,” continued Sister Ruth. “Here’s how it’s going to work. Every time you touch your privates I will add another hour to your shame punishment. You just bought yourself an extra hour of enforced nudity. Would you like to try for another? We can carry it over to tomorrow if need be.”

Tommy, certainly not keen on adding any more time to his misery, slowly moved his hands away from his genitals and put them behind his head. Laura stood in front of Tommy and did nothing to disguise her eagerness to familiarize herself with the teenager’s prepubescent anatomy. As she glared at Tommy’s penis, she had one hand over her mouth and giggled uncontrollably.

“Are you going to be able to read for us, Laura?” asked Sister Ruth, who stifled a giggle of her own.

“I’m sorry, Sister,” she giggled. “It’s just that... I never knew it was so... well, so tiny.” The statement elicited another chorus of laughter as Tommy, fighting to keep his hands clasped behind his head, wallowed in his wretchedness. "And," Laura added for good measure while continuing to stare at her current fascination, "I thought boys usually have hair down there at this age. Tommy doesn't have any."

When the giggling died down, Sister Ruth said, “Tommy, it appears you are causing a bit of a distraction for Laura. Perhaps you can turn around and face your classmates, so she won’t be preoccupied with your little penis." Tommy, with an agonized look on his face, shook his head. “That wasn’t a question, Tommy. Now please do as I say.”

Tommy braced himself as the rest of the class waited in eager anticipation. But the prospect of facing his classmates in his naked glory would prove to be unbearable. As he turned, he dropped his hands and covered his genitals.


A Most Embarrassing Reprimand

“Tommy!” chastened Sister Ruth. “What did I tell you about that filthy habit?” Tommy, facing sideways toward the window in a hunched over position, was at a loss for words. “Turn around and look at me when I speak to you, young man.” Tommy turned back and faced his nemesis. “That’s another hour you’ll be providing naked entertainment for us. Now put your hands back behind your head, please.” Tommy complied, slowly and reluctantly. He glanced at Laura, who was grinning with enjoyment as she continued focusing on Tommy’s penis. “Now repeat after me,” directed his teacher. “I will keep my naughty hands away from my little wee-wee.”

The tittering from the students increased. Tommy, now totally shamed, softly repeated most of the words. “I will keep my naughty hands away from my... my wee-wee.”

“That’s not what I said, Tommy,” corrected Sister Ruth. “Let’s try it again. I will keep my naughty hands away from my little wee-wee.”

Tommy forced himself to submit to his depraved teacher’s demands. “I will keep my naughty hands away from my... from my... from my little wee-wee" The giggling from behind him was pronounced.

“That’s more like it, Tommy. Let’s hear it one more time, only louder. I want your classmates in the back of the room to be able to hear you. Loudly and clearly, please.”

The anguished Tommy repeated the humiliating words—louder. “I will keep my naughty hands away from my little wee-wee!”

“Excellent!” Sister Ruth said brightly. “Now, go to the blackboard and write that ten times. Maybe then it’ll finally sink in. And while you’re writing, keep your other hand on your head, so you’re not tempted to touch your little wee-wee." Tommy shuffled to the blackboard, his face burning, and began scratching out the sentence. With each line, he felt the eyes of his teacher and classmates drilling into his exposed backside.

The girls tittered, the boys let out low guffaws. None of them had ever witnessed anything like this, and their wide-eyed amazement only made Tommy’s humiliation deepen.

Sister Ruth, having sent Laura back to her seat, stood at the front of the room, watching in silent bliss as the naked teenage boy she had at her beck and call catered to her every whim. She was thoroughly enjoying every minute of her morning since she had picked Tommy out to play victim to her debauchery. Her fantasy was coming to fruition, and remarkably, it was turning out to be even more delicious than she had ever imagined.

She pondered her next move as Tommy wrote the words “little wee-wee” for the tenth time. When he placed the chalk down, he hesitated, then turned his flushed face toward her. She crooked a finger, beckoning him to come toward her. Tommy shuffled backward from the board, stopping in front of her, one hand still planted on his head, the other hanging stiffly at his side—being very careful not to move it toward his penis.

“You can put both hands back on your head, please. Elbows out.” Tommy obeyed. “Now keep your arms behind your head, but I’d like you to hold on to your left elbow with your right hand, and your right elbow with your left hand. And stand up perfectly straight. No slouching.” Tommy did so, thus stretching out his body to the fullest. He could really feel his nudity now.

On with the history lesson... so hard to concentrate... I’ve never felt so stimulated... is that his math book?... what is he thinking?... let’s get him up here and provide some entertainment for us... my goodness, just look at him walking up here all naked, and clutching his little privates... a wonderful scene in its own right, but it’s time for him to feel more exposure... I’ll put his hands behind his head... he’s resisting... no sense in fighting it, my naked pet... I’ll only make it worse for you... that’s it, let Sister Ruth arrange you into a delightful pose... now push these elbows out... goodness gracious, aren’t you a sight for sore eyes... I’ve never seen anybody blush so red... this beats the heck out of the scarf treatment, doesn’t it?... look how smooth he is, all over... not a trace of hair below his neck... anywhere... so delectable... and his tiny little penis and ball sac... so cute... though I doubt if “cute” is the word he would like... it must be quite a source of embarrassment for him... all the more fun I’ll have with him today... look at Laura trying to see around his backside... and he’s turning away from her... this is so amusing... he so doesn’t want his classmates to see... I'll get Laura up here... talk about poetic justice... he sees your panties, you see his penis... oh, he couldn’t handle it, he covered up... he just bought another hour of this... right, like I was really going to give him his clothes back... okay, let’s get those hands back behind your head... just excruciating for him... look at Laura staring and laughing... oh, this is wonderful!... time for him to turn around... share his little secret with his classmates... they’re chomping at the bit... there he goes, covering up again... I won’t allow that anymore... he can write about his little wee-wee on the board... look at him... naked and doing my bidding... this is just delicious!... good boy, now let’s get your little naked self back over here... time to entertain your classmates... and intensify your humiliation... bet you didn’t think that was possible... you just watch me... let’s get you to hold your elbows behind your head... perfect... he’s really exposed now... how vulnerable he looks... it doesn’t get any better than this!... look at his cute little hairless underarms... oh, he caught my eye... I’ll look at his penis and grin for his benefit... how delightful, he blushed even brighter!

Okay... okay... this is a living nightmare, but if I can just hang on until recess... get through this history lesson, then get my clothes back... God, they’re all staring at me... Cindy keeps grinning at me... oh, God, this is awful... where’s my history book?... oh, no... I left it in the kitchen... please, I can’t bring extra attention to myself... I’ll open my math book... she won’t notice... uh-oh, she noticed... please just leave me alone... she’s calling me to the front!... I can’t go up there like this!... she’s really mad... I have to go... she’ll make it worse if I don’t... oh, God!... here I go... oh!... cover up so nobody can see... this feels so weird, walking up here naked... like a dream... a nightmare... listen to them giggling... Cindy’s right behind me... I hear her giggling over everybody... oh please, make this go away... Sister Ruth is pulling my hands away... putting them on my head... oh!... it feels even more naked standing like this!... Laura’s trying to see around me... I can’t let her see... oh, no!... oh, God!... she’s calling Laura up here... here she comes!... I have to cover up... but now I think I’m in trouble... oh, no... she added another hour of this... she’s making me move my hands back up to my head... oh, God... look at Laura, she can’t wait... why did I have to pull her skirt up?!... here goes... oh!... I can’t stand it!... look at her laughing at me... at my hairless little dick... oh, I want to cover up so bad!... but I can’t... oh, she told everyone it’s tiny... and hairless... they’re all laughing... oh, help me!... Sister Ruth wants me to turn around... oh, please... I can’t do it... I have to try... I just want my clothes back... here goes... just do it, Tommy... no, Cindy and Sally are back there... I can’t do it!... I covered up, I couldn’t help it... I think I’m REALLY in trouble now... another hour added... oh, God!... she just won’t let up... oh!... I have to say “my little wee-wee”... she looks like she is really enjoying herself... everybody is... please, I want my clothes... I have to write it on the board now... at least Laura went back to her seat... I can feel them staring at me... I’m naked, writing on the board... naked!... writing about my little wee-wee... oh, this can’t be happening!... okay, I’m done... now what does she want?... hold my elbows?... what for?... oh, now I see... I don’t like this... I’m all stretched out for her now... look at her smiling at me... she’s staring at my hairless underarms and smiling... now she’s looking at my privates... she’s grinning... how can she do this to me?!... oh, please, Sister, no more!

“Lovely,” smiled Sister Ruth. She looked her scarlet-faced, naked victim up and down and beamed. “Oh, yes. I do declare... you are such a delightful subject for shame punishment.” Sister Ruth was under control outwardly, but inside she was almost overwhelmed with stimulation. “We simply must share this with your classmates, don’t you think so, Tommy?” she teased. The only response from the agonized lad was his heavy, rapid breathing.

Again his nemesis smiled. “Now, while maintaining that lovely pose, I’d like you to turn around so your classmates can really take in your naked shame.”
Last edited by Blondie on Mon Oct 13, 2025 10:09 pm, edited 4 times in total.
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Tommy's Debasement, Chapter 5

Post by Blondie »

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Author's note: This chapter contains a segment involving anal exposure humiliation, which I know isn't for all tastes. If this does not appeal to you, simply skip over the section entitled "Rectal Humiliation."

Tommy's Debasement, Chapter 5: Anatomy Lesson

The Reluctant Model

There was no way out for Tommy now. Resigned to his fate, but with an extreme sense of dread, he slowly turned around and faced his fellow students. It was an excruciating moment for the lad, as he felt every eye in the room focusing on his genitals. He listened to the merry laughter from the entertained boys and girls. He had to stand there and take in all the stares from his spellbound audience. Many of the girls had never seen a naked boy before, and those that had certainly hadn’t under such extraordinary circumstances. The boys were enjoying the spectacle for its sheer entertainment value, and they were ever so grateful this was not happening to them.

Sister Ruth was ready to pounce on her prey. “Class, Laura brought up an interesting point a few moments ago when she said... I believe her words were, ‘I never knew it was so tiny.’ I think that while we have a live model standing naked before us, we can use this golden opportunity to learn a little bit about the male anatomy.”

She reached under her desk and produced a twelve-inch-high footstool. She placed it at Tommy’s feet. “Please step up here, Tommy, so your classmates can have a good view of you during our demonstration.”

The wretched Tommy climbed onto the stool, dutifully locking his elbows behind his head as every wide-eyed classmate stared in rapt attention. Sister Ruth strolled to the blackboard, plucked a pointer from the ledge, and took her place beside him. She turned to the class, the tip of the pointer aimed squarely at her objective.

“This is a penis, class. It comes in many different sizes. Laura was right about the size of this penis. It is quite small—much smaller than most penises of boys his age. As you can see, because of its lack of size and weight, it is pointing straight out instead of dangling down. This is unusual for a thirteen-year-old boy, and I’m sure it is a major source of embarrassment for Tommy.”

The girls were giggling, and the boys were snickering. Tommy was beside himself in his mortification while enduring the staggering humiliation.

Sister Ruth was enjoying herself immensely. She moved the pointer towards Tommy’s testicles. “This sac is called a scrotum, and inside the scrotum are two testicles. Testicles also come in different sizes, and I must say that these are quite small for someone Tommy’s age. The size of his testicles is proportional to his tiny penis. It would not be a stretch to say that his genitals are comparable in size to those of an eight or nine-year-old boy.”

Tommy squirmed miserably while being subjected to his teacher’s biting remarks and the giggling of his fellow students, but somehow he held his ground. Had he not been naked, he probably would have bolted straight out of the room.

“Sometimes the testicles hang down lower than this. As you can see, Tommy’s are quite shriveled up at the moment.”

Sister Ruth noticed a hand had risen in the far corner of the room. It belonged to Danny, a boy Tommy had recently clashed with in a schoolyard scuffle. The two boys did not like each other.

“Yes, Danny?” asked Sister Ruth, somewhat annoyed with the interruption.

“Sister,” said Danny, “Tommy’s penis is so tiny, I can’t see it from way back here. Would you mind if I borrowed his seat so I can get a closer look?”

“Certainly, Danny. Tommy won’t be needing his desk for a while, anyway.”

While Tommy winced, Danny sauntered up to the front and sat at Tommy’s desk. He exchanged amused smiles with Cindy, looked Tommy up and down, and grinned wider. “Thank you, Sister,” he said while staring at Tommy's penis. “This is perfect. I see what you mean. You were right. It's quite tiny.”

“Very well,” responded the smiling Sister Ruth.

She wielded the pointer in a circular motion around Tommy’s genitals. “Now, I’m sure you’ve noticed the complete absence of hair in this entire area.” She paused while Tommy grimaced. A few muffled snickers echoed through the room. The teacher had the students’ rapt attention. “In fact, Tommy is as hairless and smooth down here as he was the day he was born.” While the students giggled, she raised the pointer to the area slightly above Tommy’s penis. “When puberty starts, you’ll see hair start growing in this region.” She pointed back to his testicles. “Also here. I’m sure most of you boys have already started puberty, but I don’t see any sign at all that Tommy is anywhere close. It appears to me that Tommy is still a few years away from growing any hair on his body at all.”

Tommy, blushing crimson, closed his eyes, as his humiliation was all but unbearable. Sister Ruth continued.

“As boys get older, they also start growing hair in this area.” She stroked Tommy’s armpit with the tip of the pointer, and he reacted to the tickling sensation by momentarily lowering his elbow to his side. The impish nun smiled to herself, and stroked his other armpit for her own amusement, achieving the same reaction. “As for Tommy, I would not be a bit surprised if his underarms remained hairless throughout high school.”

She paused, as another idea suddenly hit her. As depraved as it was, she couldn’t stop herself.


Rectal Humiliation

“Tommy, please turn around and face the chalkboard, so we can examine your little poop hole... turn all the way around... good... now bend over at the waist... bend, I said... a little more... there, like that... you can rest your hands on your knees... that’s a good boy... now spread your legs out... a little more... excellent... now slide your hands down your legs and take hold of your ankles... all the way down... more... there we are, now turn your heels outward, with your toes pointing towards each other... come on, you can do it... there you go... yes, perfect... now, I’d like you to reach back and put your hands on your buttocks... don’t lift your head, stay bent over... that’s it... now I want you to use your fingers to spread your cheeks... come on, pry them apart... excellent!... hold that position... your little buttonhole is really on display for us now. And we have an interesting perspective of your little testicles.”

The teacher aimed the tip of her pointer at Tommy’s fully exposed anus and addressed her incredulous students. “This, class, is called a rectum. As you know, we use our rectums to expel wastes. Take a good look, because you probably will never again have the opportunity for a view of a rectum as openly spread out as you do right now. Because of the absence of hair, one can see the opening quite clearly. Notice the pinkish color tone in the surrounding area,” she said while moving her pointer in a circular motion just outside the orifice. She paused while the students, some agape, scrutinized the miserable Tommy’s bum hole. “You know, the rectum is considered a very... ’private’ area, so I think we can consider ourselves blessed that we have the chance to observe one displayed in such a stark fashion as we have here today.”

After another pause for effect, the malevolent nun continued. “And I think we should share this special moment with Tommy,” she said while walking purposefully to her desk. She opened her top middle drawer and pulled out a blue-framed, circular hand mirror. Taking it by the handle, she briskly strode back over to her subject and carefully gauged the proper angle to hold the mirror, so Tommy could examine his own rectum.

“How’s this, Tommy, can you see what the rest of us have been scrutinizing for the last couple of minutes?” There was no response. “Answer me, Tommy, what do you see?”

“A r-rectum,” came the timid reply from below.

“Can you try to be a little more descriptive than that?”

“Uh... it’s a h-hole... I don’t know what to say...” The anguish in his voice was quite evident.

“Does anything stand out, such as the color?”

“It’s... it’s...pinkish, like you said...”

“Yes... yes, indeed it is,” she said as she pulled the mirror away. “Okay, let’s move on. Tommy, you can stand up and turn around now. And please return your hands behind your head.”


A Review, and Some Degrading Questions

When Tommy stood up and faced the front, his audience was presented with an unusual sight. The blood rushing to his head from his bent-over position, coupled with the incomprehensible humiliation he’d just endured, had turned his face the blazing red of a neon sign.

Sister Ruth’s smile widened as she picked up a mirror and held it to his face. “My, my, Tommy,” she said. “You are positively glowing, aren’t you?”

Tommy’s jaw dropped slightly, as even he seemed taken aback by the sight of his profusely blushing face. Sister Ruth smiled freely as she laid the mirror on her desk before continuing with the relentless humiliation of her student.

“Okay, class, let’s review.” She pointed her pointer at Tommy’s penis. “What do you call this? Everyone?”

“A penis!” they called out in unison, all too gleefully, at least from Tommy’s perspective.

She pointed a little higher. “Does he have hair or is he hairless?"

“Hairless!” came the immediate response.

She pointed below his penis. “What is this sac called?”

“A scrotum!” they answered.

“And what are the two little round objects he has inside his scrotum?”

“Testicles!” they shouted even louder.

“Very good, class. You've been paying attention. Now let’s see if Tommy has learned anything today.” Again she pointed at Tommy’s penis. “Tell the class what this is, Tommy.”

Tommy took a deep breath. “A p-penis,” he said softly.

“We can barely hear, you, Tommy. Yes, it is a penis... but it’s not just any penis, is it? It’s your penis, isn’t it, Tommy?” Tommy nodded sullenly. “Please tell the class whose little penis we’re all staring at, Tommy.”

“M-mine,” he responded, very softly.

“Tommy, you are not being very cooperative, and I’m becoming impatient with you. Surely you must realize by now that when you make things difficult for me I have no choice but to step up your punishment.” Sister Ruth paused while considering her next move.

“Okay, we’re going to start over. I’m going to point to one of your body parts, and you’re to tell the class, loudly and clearly, exactly what it is. Only you’re to preface each response with ‘my hairless little.’ In other words, if I point here," she said while pointing to his navel, "you’re to say, ‘my hairless little belly button.’ Do you understand, Tommy?” The embattled lad nodded bleakly. “Good. Oh, and one more thing: If I point to your little penis, you’re to call it a ‘wee-wee.’ ” The beaming nun waited for the laughter behind her to die down. “Okay, here we go. What’s this?”

“My... my hairless little belly button,” he said softly.

“Speak up, please. What’s this?”

“M-my hairless little p-penis... I mean... wee-wee,” he muttered.

“Louder!” she said while wielding her pointer and swatting his backside with three swift strikes.

It took a moment for the pain to register, but when it did, Tommy hopped up and down like a jackrabbit. His penis jiggled up and down as he did so, creating a most amusing spectacle for Sister Ruth and Tommy’s fellow students.

“My hairless little wee-wee!” he shouted over the boisterous laughter.

“That’s more like it,” said Sister Ruth with a giggle she was unable to suppress. “This?”

“My hairless little tes... testicles!” Tommy writhed his hips back and forth, as he was still stinging from the three blows.

“Good!” said the grinning, titillated Sister Ruth. “This?”

“My hairless little legs!”

“How about... this?”

“My hairless little... underarms!”

“This?” she asked while pointing at his left nipple.

“My hairless little chest!”

She tweaked his nipple back and forth with the pointer. “Can you be more specific for us, Tommy?”

“My little... my hairless little nipple!”

“Good boy! This?”

“My hairless little wee-wee!” Tommy was on the verge of tears.

“Okay, I think you’ve got the idea, Tommy. This has been a very constructive demonstration. Now I think we should open up the floor to questions from your classmates.” She noticed that Laura immediately raised her hand. “Yes, Laura?”

“I was just wondering,” said Laura. “Are you going to make Tommy stay naked all day?”

Sister Ruth smiled at the question and the hopeful expression on the young girl’s face. “We’ll have to see about that,” laughed the teacher. “Either way, after today’s experience I highly doubt that Tommy will be lifting up your skirt ever again—or anyone else’s for that matter. But let’s try to limit our questions to the male anatomy for the time being. Anyone?”

Sally’s hand shot up. She wasn’t about to pass up the opportunity to further humiliate her brother. “Sally, do you have a question?”

“Yes, Sister Mary Ruth, I do. Actually I have two questions, Sister, if you don’t mind indulging me."

“Not at all, Sally. What’s on your mind?”

“Well first of all, I was wondering... will Tommy always have such an itsy-bitsy little wee-wee, or will it grow bigger? And second, why are his testicles and ball sac so shriveled up? I can barely see them.”

Sally’s eyes drifted up from Tommy’s penis to his face, and for a fleeting moment their gazes met. Hers sparkled with unrestrained delight; his, with anything but. Tommy quickly turned away, cheeks blazing, unable to face his grinning sister.

“Well, it remains to be seen, Sally, if Tommy will always have such a tiny penis. You would hope it will eventually increase in size, and maybe it will—but I’d venture to say that it is quite possible that Tommy will have a child-like penis throughout his adulthood. I would expect that he will be self-conscious and embarrassed about his undersized penis for the rest of his life.

“Now as far as his shriveled testicles and scrotum are concerned,” continued the nun, while again using her pointer on the subject matter at hand, “this can be caused by several factors—such as fear, cold temperatures, or extreme embarrassment. In this case, I’m quite sure it is the latter. As you can see from Tommy’s extraordinarily red face, his embarrassment is quite acute at the moment. Yes, Cindy, what’s on your mind?”

“Sister Ruth, I have a question about the total lack of hair.”

She addressed Tommy, who was now in the throes of wretchedness. “Tommy, I happened to notice that your face turned even redder when Sister Ruth pointed out how bald your little pee-pee is.”

Cindy, sitting just two feet from Tommy, pointed at his penis as she spoke. She knew what buttons to push to further Tommy’s torment. His blush had spread from his face clear down to his chest. It was bad enough having to stand naked in front of the entire class—but listening to the casual, matter-of-fact discussion of what he considered deeply private was nothing short of excruciating for him.

Sister Ruth relished the moment as Cindy asked her question. “When do you think Tommy can expect to finally start growing some hair on his body?”

“Hmm... that’s hard to say, Cindy.” She paused, letting her gaze travel slowly up and down Tommy. “As I mentioned earlier, it’s entirely possible he could stay hairless all the way through high school. And that, of course, would be a source of considerable anxiety... and no small amount of embarrassment. For instance, he’ll have to strip naked and shower in front of the other boys after P.E. classes. The other boys will all have larger penises and will have grown hair on their bodies, unlike Tommy. Having a penis the size of a little boy, along with the complete absence of hair will potentially be a constant source of teasing and ridicule.

"And even when he does start growing hair, it may not be very significant. Some people are just born with genes that don’t produce much body hair. This often makes them look little-boyish and somewhat feminine—like Tommy. You saw how pretty he looked in the nightgown. Not many boys would look so lovely in a girl’s nightgown.

"These are all excellent questions. Anyone else?”

Sally had raised her hand again and was waving it eagerly. "Sally, do you have another question?"

"I do, Sister Ruth, but I was wondering if I could ask Tommy directly."

"Of course, Sally. Please," the smiling nun answered while holding out an open palm toward Sally.

Sally stood up and made eye contact with her brother, then grinned mischievously. "Tommy, I was wondering... obviously this whole scene is extremely embarrassing for you. I've never seen your face so red. I can certainly understand why. I mean, you're standing there totally naked in front of all of us, and we're all staring at your hairless little wee-wee. I'm curious—as we stare at it, which is a larger source of humiliation for you—your little boy wee-wee, or the fact that it is completely devoid of hair?"

Sister Ruth nearly choked on her saliva, and was unable to suppress a giggle, which spread to the rest of her students. When the laughter died down, Tommy still hadn't answered the question.

"Sally asked you a question, Tommy," prodded the nun.

"I... I don't know," Tommy muttered, his gaze fixed on a spot on the floor in front of him.

"Pick one, so we can move on."

"I guess... I guess the size," he said ashamedly.

"The fact that it's so tiny?"

"Y-yes."

Sister Ruth addressed Sally, who still hadn't completely controlled her giggling fit. "Does that answer your question, Sally?" she asked.

"Yes, Sister, thank you. I thought it might be his tiny penis more so than his hairlessness, although I'll bet he's very embarrassed about both."

"I'm sure you're right, Sally," said the grinning Sister Ruth. "Any other questions?"

Cindy had her hand raised again. The teacher noticed a devious grin on her face, and didn't hesitate to call on her. "Yes, Cindy, did you have another question?"

"Yes, Sister. I would also like to address Tommy directly. It's a rather personal question, if that's okay."

"By all means, Cindy," answered Sister Ruth. "Tommy has already bared his body for us. Maybe now he can bare his soul."

"Thank you. Tommy," said Cindy as she looked at his penis. "Obviously your penis is really tiny when it's like that. But does it get much bigger when you get a stiffy?"

While Tommy winced, there was considerable laughter throughout the room. There was no response from Tommy, so the teacher intervened

"Class, I was planning on including what Cindy is referring to when we discuss human sexuality toward the end of the year. But since Cindy brought it up, I will tell you what many of you already know—that a boy's penis usually enlarges when he becomes sexually aroused. The clinical term is called an erection, but there are many slang terms for it, such as the one Cindy just used. Now, Tommy, you may answer Cindy’s question."

"I... I guess it gets bigger," said Tommy, who looked like he would rather endure a root canal without anesthesia than deal with the line of questioning.

"How much bigger?" asked Cindy, who was clearly enjoying herself.

"I don't... I don't know. A couple of inches?"

"That's it?" persisted Cindy. "So when you get a stiffy it must look really cute. Kind of like a mini sausage." Again there was considerable laughter. There was no response from Tommy, so Sister Ruth took over.

"Are there any other questions?" asked a giggling Sister Ruth. A couple of hands shot up, but Sister Ruth glanced at the clock. “It’s time for recess, class. Maybe we can get to your other questions some other time.”

The room was silent, and for the next few moments all the students—including the beleaguered Tommy—pondered the burning question: Would Tommy get his clothes back before going outside?
Last edited by Blondie on Mon Oct 13, 2025 10:14 pm, edited 5 times in total.
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Tommy's Debasement, Chapter 6

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Tommy's Debasement, Chapter 6: The Girls' Uniform

An Embarrassing Alternative

At first, a wave of relief washed over Tommy—recess meant his torturous experience would at least be temporarily over. But then the dreadful thought struck him: Recess also meant going outside. Surely she didn’t expect him to go outside without his clothes on in front of the whole school, he figured.

The rest of the class wondered the same thing—many secretly hoping for just that. It had been an unusually thrilling morning, and no one wanted the show to end. Normally, they’d leap up at the word recess, but not today. They stayed rooted in their seats, eyes fixed on Tommy, eager to see what fresh humiliation awaited him.

Fortunately for Tommy, Sister Ruth had enough sense not to send him outside naked. If one of the other teachers learned of the depraved activities that had taken place in her classroom that morning (an inevitable occurrence at some point), then her fun would be prematurely over. There was still the better part of the day left, and she had more perverted plans for Tommy. Instead, she was already plotting a compromise—one that would keep fellow teachers quiet while allowing her to stretch Tommy’s humiliation—and thus her pleasure.

“Tommy,” Sister Ruth began, “you can’t be expected to go outside like that, so I’ll let you get dressed for recess.” It was hard to say which reaction was stronger—the disappointment rippling through the class or Tommy’s sheer, unmitigated relief. “Take a look out the window to make sure your clothes are still there,” she added. “I’ll run down and fetch them for you.”

But Tommy’s relief would be painfully short-lived. Unbeknownst to him—or to anyone in the room—Sister Ruth had glanced outside only minutes earlier and discovered the bundle of clothes was no longer there, much to her surprise and confusion.

Tommy anxiously walked over to the window and peered down. He then moved to the next window and did likewise. Now with a look of panic on his face, he tried the last window, but he still couldn’t locate his precious clothes. His classmates were enjoying the scene of the naked Tommy bending over the windowsill, and they had a pretty good idea at this point that he was unsuccessful in locating his long-lost clothes.

“Well?” asked his teacher.

“They’re not there!” Tommy answered frantically.

“Hmm... that does create a problem,” she said, tapping her chin as though deep in thought. “According to school policy you can’t go outside during school hours without a uniform.” Her expression suddenly brightened, as if struck by an inspiration. “Oh, wait! You’re in luck, Tommy. I just remembered—I’ve got a spare uniform you can wear.”

She strode to her desk, crouched, and pulled open the bottom drawer. Tommy, though a flicker of hope sparked inside him, couldn't shake the nagging sense of unease. At this point, he didn’t trust his cunning teacher any further than he could throw her.

“Ah, here we are,” Sister Ruth announced cheerfully. She stood, holding high the girls’ uniform skirt and blouse. “See? The policy doesn’t say which uniform you have to wear. This belonged to a fifth grader, but I think it’ll fit you perfectly.”

The room erupted—giggles from the girls, loud howls from the boys. Their earlier disappointment evaporated, replaced by gleeful anticipation. Tommy heard Cindy’s distinct giggle above the rest and, glancing at Sally, caught sight of the devilish grin spreading across her face. Still by the window, Tommy again peered outside, hoping beyond hope that his clothes had magically reappeared.

“Come here, Tommy,” Sister Ruth called. “It’s time you put some clothes on.” Tommy, while chagrined at the prospect of putting on the girls’ uniform, nevertheless was somewhat consoled, since the skirt and blouse would at least cover his nudity. Slowly, he walked toward his teacher. She patted the top of her desk with a smile. “Up you go,” she said. “I’ll help you get dressed.

The wretched Tommy perched on the edge of the desk, feet dangling, facing his sadistic teacher. He kept his trembling hands rigidly at his sides, resisting the desperate urge to cover himself. He had the rapt attention of the captivated audience on his right.

“Hold out your leg, please,” Sister Ruth said, tapping his shin with a gentle but commanding touch. Tommy complied, and she rolled a crisp white knee sock snugly up his calf, then repeated the process with his other leg. Tommy winced when she opened a drawer and produced shiny black patent shoes with little buckles. His discomfort drew a knowing smile from the nun.

“Don’t worry, Tommy,” she cooed. “You’ll be a big hit in your new Mary Janes.” She slipped the shoes onto his feet one by one, buckling them with exaggerated care before stepping back to admire her work. She smiled in satisfaction. “Today really is your lucky day,” she said. “They fit like a dream! Let’s see how you look so far.” She grasped both his hands and guided him off the desk, grinning with amusement as she watched his little penis jiggle up and down from the impact of landing on the floor. Giggles swept through the room. Tommy stood stiffly, a captivating sight in nothing but white knee socks and little girl’s shoes.

“Lovely,” mused Sister Ruth, stepping back and admiring the display as she held Tommy’s hands. She lifted her eyes to his ever-blushing face and smiled wider. She reached over to the top of her desk and snatched the white blouse, holding it open while Tommy obligingly slipped his arms through. She continued to tease the unfortunate student as she slowly buttoned up the blouse.

“I apologize if this blouse isn’t quite like the other girls’,” she said. “The lacy collar makes it a bit more feminine.” She smoothed the collar with her fingers and tilted her head. “Oh yes... you’re beginning to look like a little schoolgirl now—and a blushing one, at that.” She leaned in with a sly grin. “Tell me, Tommy—are you starting to feel like a little girl yet? Perhaps this will be therapeutic... maybe once you’ve gotten in touch with your feminine side, you’ll think twice before harassing a fellow coed like you did Laura.”

Holding up the blue-and-white plaid skirt, she gave it a shake. With a resigned sigh, Tommy stepped into it. Sister Ruth zipped up the side and then took a few steps back, eyeing him closely, appraising every detail. “Oh, how lovely you look,” she purred. “If it weren’t for that short hair, I’d swear you were a young schoolgirl.”

Tommy’s gaze fell to the skirt. It barely reached his mid-thigh, while the other girls’ skirts all fell neatly to their knees. He couldn’t help but notice the difference. Sister Ruth, skilled with a needle and thread, had deliberately raised the hem by several inches, in hopes of this very application.

Panties

“All right, class, it’s time to go outside,” Sister Ruth announced cheerfully. She paused, tilting her head as if suddenly remembering something. “Oh dear... Tommy, we almost forgot your panties.” Gasps and giggles spread through the class as she opened a drawer and drew out a pair of lavender panties, holding them up with both hands and stretching the fabric wide for everyone to see. Tommy cringed when he saw the ruffles lining the backside.

This is what they looked like:

Image

The giggles intensified as Sister Ruth knelt, holding them at his feet. Tommy hesitated, then gingerly stepped in while she guided them up his legs, taunting him as she did. “I can’t believe you were even thinking of going outside without your panties, Tommy,” she chided playfully. “Why, somebody might peek right up your skirt and see your little naughties.” She yanked them snugly into place, giving the waistband a sharp snap against his midriff. She stepped in front of Tommy and gestured at the skirt. “Lift it up, Tommy. Let’s see those pretty panties.” Tommy’s head bowed in shame as he raised the front hem. Giggles and snickers filled the room, making his face burn brighter.

Sister Ruth planted her hands on her hips, a wicked smirk on her lips as her gaze dropped to Tommy’s exposed panties. “Oh, how adorable,” she purred. “And just look at that face! Now you know exactly how Laura felt when you lifted her skirt.” Both Sister Ruth and Tommy glanced at Laura, who was positively beaming at what she considered to be poetic justice. Sister Ruth motioned with her index finger, twirling it in a half-circle. “Turn around now, Tommy, and lift up the back of your skirt so we can all see the pretty frills.” Tommy obeyed, hiking the skirt up his back. “That’s nice,” Sister Ruth cooed. “Now, bend over at the waist.” Tommy did so, and the nun stepped closer, adjusting the ruffles on his panties with meticulous care.

“Pretty, pretty,” she chimed, punctuating each t. “I do declare, you’ll have the prettiest panties of all the girls on the playground.” The classroom erupted in gleeful laughter. Sister Ruth’s eyes were filled with mischief as she gave Tommy’s behind a light pat before addressing the class.

“Alright, everyone, please form two lines—girls in one, boys in the other. Tommy,” she said, turning back to him, “given your lovely outfit, you’ll join the girls’ line. Naturally, you’ll play on the girls’ side of the playground. It’s a breezy day, so do take care not to let your skirt fly up. A proper young lady never lets her panties show.” She paused, savoring Tommy’s miserable expression. "Sally and Cindy, can I count on you to include Tommy in whatever games you play? He's had a rather difficult morning, and I think some exercise will do him good."

“Oh, we’ll take good care of him, Sister Ruth,” Sally replied with a sly grin.

Tommy slunk toward the girls’ line, Sally and Cindy close behind. He felt the back of his skirt flutter, exposing the frilly panties underneath. Instinctively, Tommy reached back to push the hand away, only to glance over his shoulder and see Laura grinning at him derisively.

The giggles from his classmates were relentless. Tommy could feel every eye trained on him as they entered the hallway and descended the stairs. He was painfully aware of how out of place he looked and how uncomfortable he felt. He was about to step outside, in front of the entire school, no less, in a girls’ uniform—including panties! There were still five long hours of school ahead, and he couldn't help but wonder what other humiliations his mischievous teacher had planned for him.

And what on earth had happened to his clothes?
Last edited by Blondie on Mon Oct 13, 2025 10:16 pm, edited 5 times in total.
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Tommy's Debasement, Chapter 7

Post by Blondie »

Image

Chapter 7: Playground Humiliation

Skipping Around the Playground

When the class stepped outside to join the rest of the students, Sally and Cindy—grinning mischievously—each grabbed one of Tommy’s hands and began parading him around the girls’ side of the playground. Within moments, a crowd of curious, giggling girls trailed behind them, while the boys across the yard paused their games, staring from a distance.

Word of Tommy’s earlier humiliation had already spread, and now, as the buzz intensified, the excitement among the girls became palpable. The playground was alive with laughter and whispers, all eyes focused on Tommy, whose face had flushed a deep crimson.

Trying to avoid eye contact with anyone, Tommy kept his head down. Sally and Cindy, still clutching his hands, began to pick up the pace—first walking briskly, then skipping. Tommy had to jog at times just to keep up with the grinning pair.

“Come on, Tommy, skip with us!” Sally called out cheerfully. “We promised Sister Mary Ruth we’d get you some exercise. You want us to give her a good report, don’t you?”

Tommy had no choice but to follow the lead of his two tormentors. While he skipped around the yard his skirt bobbed up and down, briefly exposing his ruffled panties with each skip. His attempts to hold the skirt down were rebuffed, as the girls had a firm grasp of his hands. The girls’ laughter grew louder, egged on by the appreciative audience. Sally and Cindy were having the time of their lives It was certainly a recess session no one would soon forget.


The Eighth Graders

The girls eventually became winded, so they stopped with Tommy by a bench against the wall of the school building. Tommy used the opportunity to sit down, being careful to smooth down his skirt.

Most of the girls lingered nearby, clearly enjoying the unusual spectacle. Tommy shifted uncomfortably, feeling the weight of their stares. Three girls from the eighth grade approached, looking at him with a mixture of curiosity and amusement. Two of them sat down on either side of him, while the third stood next to Sally and Cindy, her arms folded as she observed the scene. Not far behind them a large gathering of girls looked on with considerable interest. Tommy was becoming more ill at ease by the second.

The cute girl on Tommy’s left smiled sweetly as she ran a hand through his blond hair. "Hi, pretty boy, I’m Karen," she said with a teasing tone. "This is Linda next to you, and that's Nancy," she said while pointing to the grinning girl standing above him.

“Please, just leave me alone,” pleaded Tommy while staring down to the ground.

"His name is Tommy," Sally chimed in, clearly enjoying his discomfort.

Karen’s smirk widened. "Tommy, huh? You're dressed more like a ‘Tammy’ to me," she teased. "May I call you Tammy?”

Tommy started to rise, but Nancy persuaded him back down with a gentle but purposeful push to his shoulders. “Don’t leave, Tammy,” Karen said. “We’re just trying to be friendly. We heard you were quite the exhibitionist in class today, with your little striptease act. We feel like we really missed out. We’re thinking that since you showed your goodies to the seventh graders, then maybe you can put on a little show for your upper-class girls.”

Karen’s grin widened, and Tommy’s fear grew. It was clear they weren’t going to let him go without a fight. But no matter how much he wanted to run, he knew he had no choice but to stay and endure the teasing.

"We think you owe us a little show too, don’t you think?" persisted Karen. Tommy’s face paled. His worst nightmare was unfolding before his eyes—these girls wanted to see more. The thought of stripping again in front of them caused his anxiety level to rise considerably.

Tommy’s skirt had ridden up slightly when he sat down, exposing more of his thighs than he would have liked. Karen, her grin widening, casually ran her fingertips across the top of his left thigh. "You have such pretty legs, Tammy," she cooed. "So smooth and soft—just like a girl’s." Tommy flinched, shifting uncomfortably as giggles rippled through the crowd. "Feel them, Linda," Karen encouraged, her teasing tone in full effect. "They’re so nice and silky smooth.”

Linda obliged, running a finger along his right thigh. “Ooh, you’re right, Karen,” taunted Linda. "Smoother than a baby’s bottom. Maybe as smooth as Tammy’s bottom! Can you show us your baby smooth bottom, Tammy?” The gathered girls erupted into laughter as Tommy’s blush deepened to an impossible shade of red. He squirmed in place, wishing he could sink into the bench and disappear.

Then Karen’s hand delved a little higher up Tommy’s thigh, probing under his skirt. Tommy instinctively grabbed her wrist and pulled her hand away. Karen immediately slapped him across his face, marking the second time that morning that his face had been slapped.

“You keep your hands off me, Tammy!” warned Karen, “Do you hear me? You touch me again and we’ll strip off your girly clothes and have you skipping naked around the playground. From what I hear, it would be quite a site, what with your little-boy penis bobbing up and down for us all to laugh at.” Tommy now had tears in his eyes. “Oh, poor baby,” said Karen as she softly wiped a tear from his cheek with her thumb. “Did Auntie Kawen make you cwy?”


Nearly Stripped

"Hey, Tammy," Karen went on, her eyes dancing with mischief, "how about a little twirl for us? You know, to show off those pretty legs."

Tommy shook his head, gripping the hem of his skirt protectively. "N-no... just... please, just leave me alone."

"Aww, don’t be shy, Tammy," said Karen. "You did a little show for your class earlier, didn’t you? I think we deserve one, too!"

Before Tommy could protest further, Linda—who had been fiddling with the back of his skirt—gave a triumphant tug, and suddenly the zipper was all the way down. Tommy, oblivious to his impending doom, was too preoccupied with Karen’s teasing to notice. Karen didn’t miss a beat. “All right, you can go now, Tammy,” she said. “I’m sorry; I didn’t mean to make you cry.”

Desperate for an escape, Tommy scrambled to his feet—only to feel a sudden rush of cool air around his legs. A collective gasp was followed by peals of laughter as his skirt slipped right down to his ankles. Tommy froze in horror before bending over to snatch it up, affording the giddy girls a marvelous view of his pantied behind.

"Awww, look at Tammy’s little ruffles!" Nancy teased, clapping her hands in delight.

Tommy hastily tried to step back into the skirt, but in his panic, he stumbled. Cindy swooped in, swiping it up before he could grab hold of it. "Looking for this?" she asked with a giggle, holding it just out of reach.

"Give it back!" he pleaded, reaching for it as the girls passed it between them like a game of keep-away.

"Not so fast, pretty boy!" Linda teased. "I think we deserve a peep show first!"

Tommy’s mortification was at an all-time high. But it was about to intensify, because the devilish Karen reached for the back of his panties and managed to pull them down far enough to completely expose his rear end, eliciting yelps of glee from the spectators and a cry of anguish from Tommy. He reached back with one hand to pull them up while trying to reach out for the skirt with the other. But Karen continued tugging on the panties. In serious danger of having them pulled further down and possibly completely off, Tommy had to forgo his efforts with the skirt to devote full attention to Karen’s onslaught.

Meanwhile, Linda and Nancy swooped in to the aid of their friend Karen. Linda pulled upward on Tommy's blouse while Nancy pulled on his arms.
“Let’s strip him!” cried Linda. Tommy was in serious trouble. There was no way he would be able to stave off the attack much longer.

“Strip him naked!” shouted an energized girl from the crowd, and when Sally and Cindy moved to join in, it appeared that they would do exactly that. Indeed, for one brief moment, Linda had pulled the panties halfway down his thighs, affording her a fleeting glimpse of the teenager’s prepubescent package.

“No! No, please!” Tommy cried out in distress.

Then, for the first time that day, something positive occurred for the beleaguered Tommy. It was the classic “saved by the bell,” as the loud shrill rang throughout the schoolyard. A teacher opened the doors, and the girls—grinning from ear to ear—reluctantly backed off, allowing Tommy to quickly yank up the panties. Cindy tossed the skirt back at Tommy, who fumbled to zip it up as quickly as possible.

“I saw it!” squealed Linda to Karen. Grinning derisively, she held out her thumb and index finger, spreading them about an inch and a half apart. Both girls laughed bawdily.

“Thanks for the sneak preview, Tammy,” Karen chortled as she walked past him while he was zipping up. “But it wasn’t nearly enough, you little tease. I saw your cute little bum but not your little weenie. Let's pick up where we left off at lunch time.” Tommy, unnerved, shuddered as he shuffled into the building amid the throng of thoroughly entertained students.

Back in class, he slumped into his seat, hoping—praying—that math would provide some much-needed relief from his ordeal.

"Pull out your math books and turn to page ninety-two," Sister Mary Ruth instructed. Tommy exhaled in relief. Maybe, just maybe, he’d survive this lesson without any further humiliations.

But, as the reader has probably surmised, that would not be the case. It would be five minutes into the math lesson when Sister Mary Ruth pulled her calculated move. “Okay, you have x=2y + 7, and you have... Tommy, why aren't you naked?” Tommy was disheartened. “Please come here, so we can remedy that for you.”

The interest level of the students suddenly increased exponentially.
Last edited by Blondie on Mon Oct 13, 2025 10:19 pm, edited 4 times in total.
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Re: Tommy's Debasement

Post by TeenFan »

I used math the humiliate a boy in a story...hoping something similar happens here.
In the story, a thirteen year old boy (in Re-Writing Actual Movie Scenes), who was given a Naked at home punishment, assists some other kids during
a tutoring session. Math problems are being worked on, and Romeo is forced to have his penis measured erect and soft so the percentage increase
can be calculated. Who said math can't be fun?

I think I would have preferred to stay naked in the classroom rather than go outside in the girl uniform. At that age I'd have been more afraid
of the mob of girls than scared of the teacher.
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Re: Tommy's Debasement

Post by Blondie »

TeenFan wrote: Wed Dec 13, 2023 5:38 pm I used math the humiliate a boy in a story...hoping something similar happens here.
In the story, a thirteen year old boy (in Re-Writing Actual Movie Scenes), who was given a Naked at home punishment, assists some other kids during
a tutoring session. Math problems are being worked on, and Romeo is forced to have his penis measured erect and soft so the percentage increase
can be calculated. Who said math can't be fun?
I like it!
TeenFan wrote: Wed Dec 13, 2023 5:38 pmI think I would have preferred to stay naked in the classroom rather than go outside in the girl uniform. At that age I'd have been more afraid
of the mob of girls than scared of the teacher.
Retrospectively, given the choice (which he wasn't), I think Tommy might have availed himself to that.
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Re: Tommy's Debasement

Post by imanewb »

Blondie wrote: Wed Dec 13, 2023 6:21 pm
TeenFan wrote: Wed Dec 13, 2023 5:38 pm I used math the humiliate a boy in a story...hoping something similar happens here.
In the story, a thirteen year old boy (in Re-Writing Actual Movie Scenes), who was given a Naked at home punishment, assists some other kids during
a tutoring session. Math problems are being worked on, and Romeo is forced to have his penis measured erect and soft so the percentage increase
can be calculated. Who said math can't be fun?
I like it!
Don't forget geometry - make a shape, angle, whatever using your body / with a partner - lots of possibilities for interesting views and 'inadvertent' touching.

Or ratios, foot size to penis length? (statistical testing/correlation would require more than one victim however).

Something I did with kids in class a few times (not naked, obviously) was estimating volume - break the body down into appropriate shapes, cylinders, cubes, spheres, etc - class measured each other as best they could and calculated out approx. volume.

For a story like this, could they all measure tommy, and then have an embarrassing discussion about differences in calculated values? How much due to difference between flacid/erect vs, 'sloppy measuring', if sister M can get her hands on a big enough tank of water do a simple displacement test to see who got the closest and award them a prize?
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Re: Tommy's Debasement

Post by Blondie »

imanewb wrote: Wed Dec 13, 2023 8:10 pm
Blondie wrote: Wed Dec 13, 2023 6:21 pm
TeenFan wrote: Wed Dec 13, 2023 5:38 pm I used math the humiliate a boy in a story...hoping something similar happens here.
In the story, a thirteen year old boy (in Re-Writing Actual Movie Scenes), who was given a Naked at home punishment, assists some other kids during
a tutoring session. Math problems are being worked on, and Romeo is forced to have his penis measured erect and soft so the percentage increase
can be calculated. Who said math can't be fun?
I like it!
Don't forget geometry - make a shape, angle, whatever using your body / with a partner - lots of possibilities for interesting views and 'inadvertent' touching.

Or ratios, foot size to penis length? (statistical testing/correlation would require more than one victim however).

Something I did with kids in class a few times (not naked, obviously) was estimating volume - break the body down into appropriate shapes, cylinders, cubes, spheres, etc - class measured each other as best they could and calculated out approx. volume.

For a story like this, could they all measure tommy, and then have an embarrassing discussion about differences in calculated values? How much due to difference between flacid/erect vs, 'sloppy measuring', if sister M can get her hands on a big enough tank of water do a simple displacement test to see who got the closest and award them a prize?
All good ideas, but I plan on keeping with the original as best I can. But good food for thought for future stories!
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