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. He sensed the grinning gaze of Cindy on his left, but he avoided eye contact with her.

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 had a look of bewilderment on his face. There was a momentary silence while Tommy pondered his teacher’s statement. “Can somebody go down and get my clothes for me?” he asked anxiously.

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

His fellow students looked on wide-eyed and open-mouthed in 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 responded with a smile and a twinkle in her eyes.

Tommy eyed his underpants that hung tantalizingly at the chalkboard. "Can I...can I at least put my underpants on first?" he asked with no small amount of desperation.

"No, I find it rather amusing to have your underpants on display for us. And I think your classmates feel the same way."

“B-But…”

“No buts about it!” shot back Sister Ruth. “And I’m getting sick and tired of your constant insubordination. Now take that nightgown off immediately!” she bellowed while marching over to Tommy’s desk. She stood in front of him with her hands on her hips and a menacing look on her face. As intimidating as she was, Tommy still couldn’t bear to strip naked in front of the nun and all of his classmates.

“Please, Sister Ruth, let me go down and get my clothes,” he begged, his voice cracking. “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 five seconds to slip off your nightgown and hand it to me. One…” She counted very slowly while Tommy squirmed, terrified of his plight. “Two…”

“Oh please, Sister,” implored Tommy as he fidgeted nervously.

“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, visibly shaking, reached for the hem of the nightgown, but just couldn’t bring himself to do the evil nun’s bidding.
Sister Ruth couldn’t contain the slight smile that appeared on the corners of her mouth. “And, five! Okay, that does it, Tommy,” she said as she approached him purposefully. “Let’s get your nightgown off. Any you’ll be sorry you disobeyed me.”

Now standing behind his chair, with both hands she reached around him, taking hold of the hem of the nightgown from both sides of Tommy’s legs. She pulled it toward her. “Lift up your bottom!” she ordered. Tommy was overwhelmed by the nightmarish turn of events. He hesitated, but succumbed to the intimidation of his teacher and briefly lifted up in his seat, which was all the impassioned nun needed to pull the material free from beneath him. Tommy felt the gown slide under him and begin its ascent. He clenched his knees together and leaned forward to obstruct the view of the gawking students. “Arms up!” directed Sister Ruth. Tommy obediently, almost involuntarily raised his arms while Sister Ruth moved to the front of her prey and pulled the nightgown off inside out in one swift motion. Smiling smugly, she calmly sauntered to her desk and deposited the nightgown in the open drawer before promptly slamming it shut with her foot.

And just like that, Tommy, experiencing any young student’s worst nightmare, was sitting at his desk in front of all of his classmates, completely and totally nude.

There was a buzzing throughout the classroom. The students were absolutely incredulous at what they were witnessing, while Tommy was slowly recovering from the shock of the moment, and the realization of his desperate condition had sunk in. He leaned over with his legs together and his hands firmly cupped over his genitals, frenetically struggling to cover his nudity.

Sister Ruth turned from her desk and looked at her naked, frenzied student. A wicked smile formed on her lips. She slowly ambled towards her subject. Stopping at his desk, she smiled down on her hapless victim, fully savoring the moment. She trembled slightly, as a wave of pleasure swept through her body. 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.

The perverted nun was ready to proceed with her depravity. “I’d like you to sit up straight, Tommy. I’ve told you before how important good posture is.” The wretched student leaned up against the back of his chair, keeping his hands clutched over his privates. Tommy squirmed in his seat while enduring the staggering humiliation. “Now kindly fold your hands on top of your desk,” she commanded.

The distraught Tommy shot a furtive glance to the girl on his left and flushed deeper when he made eye contact with Cindy, who was looking him up and down, grinning widely. With the sounds of the giggling students ringing in his ears, the naked student pushed his penis between his legs and desperately clinched his knees together ever so tightly before obeying the sinister nun by folding his hands on top of his desk. He raised his knees as high as he possibly could until they came in contact with the underside of his desk. Only the tips of his toes touched the ground.

Again he glanced over to Cindy, who was now craning her neck in an effort to see between the lad’s legs. Tommy squeezed his knees together yet tighter and turned his hips slightly to his right. But when he glanced to his right he made eye contact with Laura, who was also grinning freely and trying to see between his legs. Tommy squared up. There was nowhere for him to hide.

Sister Ruth observed the scene and smiled with satisfaction. “You’ll keep your hands above your desk at all times,” she directed. With that she turned, her face flushed with pleasure, and swaggered back to her desk. When she turned back around, her gaze automatically turned to the stunned, trembling, naked teenager. She smiled with delight before addressing her students. “Okay, class, where were we before that nude—er, rude interruption?” Giggles abound. “Oh, yes, the events leading up to the conflict between the North and the South…”

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 boy 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’ll 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….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 with the history lesson. Tommy didn’t hear a word she was saying as he squirmed in his chair, stealing frequent glances at the clock. Time was moving painfully slowly for him.

His fellow classmates weren’t digesting very much of the lesson either, as their concentration level was considerably distracted by the naked classmate, a truly extraordinary development. The excitement level in the room was palpable, and it had absolutely nothing to do with the Civil War.

“Class, I’d like you to open your history books to page one hundred and twelve.” To the sounds of desktops opening and books being shuffled, Tommy opened his desktop to search for his history book. He knew tha t all eyes in the room were scrutinizing his every movement.

But he now had more immediate concerns. He had gone through every book in his desk, but for the life of him he couldn’t find his history book. Then he remembered seeing it lying next to the toaster on the kitchen counter while he was eating breakfast earlier that morning. He had forgotten it.

“Oh, no,” the distressed Tommy whispered to himself. He pulled out his math book and opened it up on his desk. He hoped his teacher would overlook the fact that he didn’t have his history book. His hopes died in about five short seconds.

“Tommy, that doesn’t look like your history book. Did you not hear me or are you intentionally disobeying me?”

“I-I-I....” Tommy was stuttering badly. “I left my history book at home.”

Sister Ruth was secretly relishing his disclosure, but she feigned exasperation. “You what? 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. “You already are being shamed by having to sit there stark naked in front of all your classmates. Then you realize that you forgot to bring your history book, and you have the audacity to try to deceive the class and me by pulling out your math book. Don’t you think you are in enough of a predicament already not to pull a stunt like that?” She didn’t wait for an answer, and there was none forthcoming.

“Come up here right now, young man.”
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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 this 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 prepubescent teenager’s 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 towards 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! Now I want you to go to the blackboard and write that ten times. Maybe then you’ll have it ingrained in your mind. And while you’re writing you’re to keep your non-writing hand on your head so you’re not tempted to touch your little wee wee.”

Tommy obeyed by walking straight to the blackboard and performing his punishment. He could almost feel the glares from his teacher and classmates zeroing in on his backside and overall naked state.

The tittering from the girls and the guffaws from the boys continued. Of course they had never seen a spectacle anything like this before, and their eyes were wide in amazement.

Sister Ruth, who had sent Laura back to her seat, stood in 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.

Tommy put the chalk down and turned his head back toward his teacher. She motioned with her index finger for him to come toward her. He walked backward from the board and stopped in front of her. He still had one hand on his head and the other 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….oh, he’s just hating this, isn’t he?.…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.…how delectable….and his tiny little penis and ball sac.…so cute.…though I doubt if “cute” is the word he would use.…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!….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 so 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.”
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Tommy's Debasement, Chapter 5

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Author's note: This chapter contains a segment devoted to 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 stepped up on the stool, dutifully holding his elbows behind his head, while his enthralled classmates looked on wide-eyed. Sister Ruth walked to the blackboard and picked up a pointer from the ledge. She stood next to Tommy and addressed the class while pointing the pointer 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 anxiously 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 with whom Tommy had recently gotten into a schoolyard fight. 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 couple of snickers could be heard. 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. With the blood having rushed to his head due to his bent-over position, coupled with the incomprehensible humiliation he had just endured, Tommy’s face was the color of a red neon sign. Sister Ruth beamed with pleasure. She held the mirror up to Tommy's face. “My, my, Tommy, 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?"

“He's 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 coed’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 let the opportunity to further humiliate her brother go by. “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 ever grow bigger? And second, why are his testicles and ball sac so shriveled up? I can barely see them.”

Sally’s gaze rose from Tommy’s penis and testicles to his face. The two made brief eye contact. One pair of eyes was dancing with delight. The other pair most certainly was not. Tommy turned his flushing face away from 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 still have a teensy penis throughout his adulthood.

“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 by 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. “Sorry, Tommy, but I happened to notice that your face turned even redder when Sister Ruth pointed out how bald your little pee-pee is.” Cindy, sitting two feet away from Tommy, pointed at his penis as she spoke. She knew what buttons to push to further Tommy’s torment, and he now seemed to be blushing from his head and down his chest. Not only did he have to stand naked in front of the whole class, but also, the matter-of-fact discussion about what for him were extremely private matters was absolutely 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 and looked Tommy up and down. “As I mentioned earlier, it is quite possible that he could remain hairless throughout all of high school. This, of course, would be cause for considerable anxiety and embarrassment. For instance, he’ll have to take his clothes off 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 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 bodily hair. This often makes them look little-boyish and somewhat feminine, like Tommy. You saw how pretty he looked in his 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 see 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," said Tommy as he stared at 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, Cindy asked you a 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?
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Re: Tommy's Debasement, Chapter 6

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

An Embarrassing Alternative

Initially a sense of relief came over Tommy, as his torturous experience would at least be temporarily over. But then it dawned on him that recess meant venturing 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 was wondering the same thing, and many were hoping for exactly that. It had been a very exciting morning for them, and they were hoping that their entertainment would be sustained. Normally, they all would have jumped out of their chairs at the word “recess,” but Tommy’s plight carried much more weight for them. They remained in their seats, waiting to see how the next scene would play out.

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 to satiate her desires. She had a compromise in mind that would help keep the rest of her fellow teachers quiet, but would also extend Tommy’s humiliation—and thus her pleasure.

“Tommy,” began Sister Ruth, “You can’t be expected to go outside like that, so I’m going to let you get dressed for recess.” It is hard to say which was more pronounced: Tommy's classmates' disappointment or Tommy’s unmitigated relief. “Take a glance outside to make sure that your clothes are there, and I’ll run down and get them for you.”

But Tommy's sense of relief would be short-lived. Unbeknownst to Tommy and his classmates, when Sister Ruth had looked out the window a few minutes before, Tommy’s clothes were 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 window sill, 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. According to school policy you can’t go outside during school hours without the uniform on.” She paused for effect, cupping her chin with her hand as if she was deep in thought. Then her face brightened, as if she just had an inspiration. “I just remembered! You’re in luck, Tommy. I have an extra uniform in my drawer that you can wear,” she said as she walked over to her desk and opened the bottom drawer. Tommy, though hopeful, looked on apprehensively. At this point he felt he couldn't trust his devious teacher as far as he could throw her.
“Oh, yes, here we are,” she said as she pulled out the girls’ uniform skirt and blouse and held them high for all to see. “The policy doesn’t state which uniform you have to wear. This used to belong to a fifth grader, but I think it’ll fit you just fine.”

The giggling from the girls and the howling from the boys echoed throughout the room. Their disappointment had suddenly turned to gaiety, as their interest and amusement were rejuvenated. Tommy could hear Cindy’s characteristic giggle over everyone. He shot a quick glance at his sister Sally and noticed the devilish grin on her face.

Tommy, still by the window, again peered outside, hoping beyond hope that his clothes would magically reappeared.

“Come here, Tommy, it’s time you put some clothes on,” instructed Sister Ruth. 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. He walked over to his teacher, who patted the top of her desk. “Have a seat up here and I’ll help you get dressed.”

The wretched Tommy sat on the desk, his feet dangling, facing his sadistic teacher. He was careful to keep his hands at his sides, fighting to keep from covering himself. He had the rapt attention of the captivated audience on his right. “Hold out your leg, please,” Sister Ruth said as she tapped his right shin. She unrolled a white knee sock up his leg, and then repeated the process with his left leg. Tommy winced as she reached in her drawer and pulled out a pair of shiny, black-patent shoes with buckles on them. Tommy’s disconcerted expression was not lost on the smiling nun. “Don’t worry, Tommy, you’ll be a big hit in your new Mary Janes.” She slipped each shoe on his feet and deliberately buckled them. She smiled in satisfaction. “Today really is your lucky day, Tommy.…they’re a perfect fit! Let’s see how you look so far.”

She took both of his hands and pulled him off the desk. She grinned with amusement as she watched his little penis jiggle up and down from the impact of landing on the floor.

The giggling in the classroom persisted, as Tommy was quite a sight, wearing only white knee socks and little girl’s shoes.

“Lovely,” mused Sister Ruth, stepping back and admiring her handiwork as she held Tommy’s hands. She looked up at 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 that this blouse isn’t quite like the other girls’, Tommy. The lacy collar on this one is much more feminine. Oh, yes, you’re starting to look like a blushing little schoolgirl now,” she taunted as she buttoned the last button and smoothed down the collar with her fingers. “Are you starting to feel a like a little girl, Tommy? Actually, this is probably quite therapeutic. Maybe if you get in touch with your feminine side you’ll be less likely to harass a fellow coed like you did Laura.”

She held out the blue and white plaid skirt and Tommy reluctantly stepped into it. She zipped up the side zipper and stepped a couple of feet back to survey the results. “Oh, how lovely you look, Tommy. If it wasn’t for your short hair I’d swear your are a young schoolgirl.”

Tommy looked down forlornly at the skirt he was wearing. He couldn’t help but notice that it only came down to his mid thighs, whereas the hem of the skirts the girls were wearing came down to their knees. Sister Ruth, quite competent with a needle and thread, had raised the hem some six inches in hopes of this very application.


Panties

“All right, class, it’s time to go outside.…oh dear.…Tommy, we almost forgot your panties.” Sister Ruth opened her drawer and pulled out a pair of lavender panties and held them up with both hands, stretching them out sideways for effect. Tommy cringed noticeably when he saw the fuchsia-colored ruffles lining the backside.

The class continued their giggling as she held them open at Tommy’s feet. Tommy gingerly stepped into them while his teacher pulled them up, talking to him as she did. “I can’t believe you were even thinking of going outside without your panties, Tommy. Somebody could look right up your skirt and see your little naughties.” She pulled the panties all the way up, snapping the band on Tommy’s midriff as she did so. She stepped in front of Tommy and pointed at the skirt. “Lift up your skirt, Tommy. Let’s see how you look in your pretty panties.” The chagrined Tommy bowed his head and lifted the front of the skirt. His face flushed with shame as he endured the giggling and snickering from his classmates.

Sister Ruth, her hands on her hips and a smirk on her face, stared at Tommy’s exposed panties. “Oh, how adorable,” teased the nun. “My, how red your face is! Now you can appreciate 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 on the back of your panties.” Tommy obeyed, lifting the skirt up his back. “That’s nice, Tommy, now bend over at the waist.” When the miserable Tommy bent over, the evil nun moved forward and fiddled with the frills, as if to make minor adjustments. “Pretty, pretty," she said, accentuating the "t" sounds. "I do declare, you’ll have the prettiest panties of all the girls on the playground.”

The merry giggling from the students exacerbated his extreme anguish. Sister Ruth patted Tommy’s behind and addressed the class. “All right, class, please form two lines, girls in one line, and boys in the other. Tommy, considering your attire, you’ll be in the girls’ line, and of course you’ll play with the girls on their side of the playground. It’s a little breezy out there, so be careful to make sure your skirt doesn’t blow upward. Proper girls don’t let their panties show.” She paused and smiled at Tommy’s dolorous expression. “Sally and Cindy, can I count on you to include Tommy in whatever games you play? He’s had a somewhat difficult morning, and I think some exercise will be beneficial for him.”

“Oh, we’ll take good care of him, Sister Ruth,” replied Sally wryly, smiling brightly.

Tommy filed into the girls’ line, with Sally and Cindy close behind him. He felt the back of his skirt lifted up, exposing the frilly panties. Tommy reached back and pushed a hand away. He looked back and saw that the owner of the hand was Laura, who was grinning derisively.

Giggles were aplenty, as Tommy’s fellow students were in a state of giddiness over the events of the most extraordinary morning. He felt all eyes on him as they entered the hallway and stepped down the stairs. Tommy was, of course, very self-conscious, and quite apprehensive. He was about to step outside in front of the whole school and endure the recess while wearing a girls’ uniform—including panties! Plus, there were five long hours to go, and who knows what his wicked teacher had in store for him?

And what on earth had happened to his clothes?
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Tommy's Debasement, Chapter 7

Post by Blondie »

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Chapter 7: Playground Humiliation

Skipping Around the Playground

When the seventh grade class stepped outside to join the rest of the students, Sally and Cindy, grinning freely, each grabbed one of Tommy’s hands and began parading him around the girls’ side of the playground. Within a matter of moments there was a crowd of wide-eyed, giggling girls trailing the trio. The boys on the other side of the yard had halted their baseball and basketball games and were watching from a distance.

Word quickly spread about Tommy’s earlier female clothing shame and his forced nudity in the classroom. There was a buzz in the air, and the excitement level was pronounced.

As all eyes focused on him, Tommy, blushing crimson, avoided eye contact with everyone. Sally and Cindy, clutching Tommy’s hands securely, gradually started walking faster and faster, until they sped to a skip. Tommy walked briskly, occasionally speeding to a trot to keep up with the grinning twosome.

“Skip with us, Tommy,” ordered Sally. “We promised Sister Mary Ruth you’d get some exercise. You want us to give Sister Ruth 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.

Sally and Cindy were having the time of their lives while being cheered on by their appreciative audience. 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 were milling around in the vicinity of Tommy, very much absorbed in the unusual spectacle. Within moments after he was seated, three girls from the eighth grade approached him. Two of them sat down on either side of him, while the other stood facing him next to Sally and Cindy. 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 his left spoke first. “Hi, pretty boy, my name’s Karen,” she said as she ran her hand through Tommy’s blond hair. “This is Linda, and that’s Nancy.”

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

“His name is Tommy,” Sally offered.

“Gee, Tommy,” teased Karen, “You’re dressed more like a ‘Tammy.’ 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.”

A look of fear swept across Tommy’s face. Although wearing the girl’s uniform caused him considerable humiliation, in his estimation it sure beat the hell out of public nudity.

Tommy’s skirt had risen up a couple of inches when he sat down. Karen, eyeing Tommy’s thighs, ran the tips of her fingers back and forth across the top of his left thigh. “You have very pretty legs, Tammy. They're girly legs.” Tommy squirmed uneasily. “Feel Tammy’s legs, Linda,” continued the grinning Karen. “They’re so nice and silky smooth.”

Linda stroked Tommy’s right thigh. “Ooh, you’re right, Karen,” taunted Linda. “They’re smoother than a baby’s bottom. Maybe as smooth as Tammy’s bottom. Can you show us your baby smooth bottom, Tammy?”

There was giggling all around as Tommy sunk deeper into the throes of wretchedness. 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

Meanwhile, on his other side Linda was surreptitiously working on the zipper of Tommy’s skirt. It had gone completely unnoticed by the unsuspecting Tommy that his skirt had been zipped as far down as it would go
.
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.”

The devious girls' plan worked to perfection. When Tommy stood up, the skirt instantly dropped to his ankles. Panicking, he bent over to pick it up, affording the giddy girls a marvelous view of his pantied behind. Karen reached for the back of his panties and managed to pull them down far enough to 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 struggling with his 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. In doing so, the skirt dropped to the ground, and as Karen pulled, Tommy moved with her, causing him to step out of the skirt, much to the hilarity of the onlookers.

Meanwhile, Linda and Nancy swooped in to the aid of their friend Karen. Linda pulled upwards 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 seemed quite possible that they could 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 aggressors backed off, allowing Tommy to quickly yank up the panties and recover the skirt.

“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. I’ll see you again at lunchtime.”

Tommy, unnerved, shuddered as he shuffled into the building amid the throng of thoroughly entertained students.

Back in class, Tommy slithered into his seat, still wearing the girls’ uniform. It was time for math class, and he hoped to survive the whole period without drawing any more attention to himself. His hopefulness increased when Sister Ruth paid him no notice and said, “Pull out your math books, class, and open up to page ninety-two.”

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, my little schoolgirl, so we can remedy that for you.”

The interest level of the students suddenly increased exponentially.
TeenFan
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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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Blondie
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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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