Pantsing and Stripping Forums

The following is applicable to all chapters of “Tommy's Debasement:”

© 2001 by Blondie.

This is a work of fiction and is fantasy only. Names, characters, places and incidents are products of the author's imagination and are used fictitiously. Any resemblance to actual events or locales or persons, living or dead, is entirely coincidental.

For ages 18 and older only.

Chapter 1: Shame Clothing
Chapter 2: Nightgown Up, Underpants Down
Chapter 3: Naked in the Classroom
Chapter 4: Exposed to His Upskirt Victim
Chapter 5: Anatomy Lesson
Chapter 6: The Girls' Uniform
Chapter 7: Playground Humiliation
Chapter 8: Forced to Entertain
Chapter 9: The Girls' Bathroom
Chapter 10: Girls' Lunchmeat: Tommy
Chapter 11: Sisterhood of Humiliation
Chapter 12: Forced Outside Naked
Chapter 13: The Spanking Gauntlet
Chapter 14: The Dreaded Dance Class
Chapter 15: Depantsed Again
Chapter 16: At the Mercy of a Gaggle of Girls
Chapter 17: The Naughty Niece
Chapter 18: Submission to a Volleyball Player
Chapter 19: Twelve Peeks Inside the Underpants
Chapter 20: A Sibling Spanking
Chapter 21: The Moment of Truth
Chapter 22: The Final Humiliation



Chapter 1: Shame Clothing

Sister Ruth’s Propensity

It started out as a normal school day in Sister Ruth’s seventh grade classroom. The first hour was devoted to English, and the nun was droning on about diagramming sentences. Boredom was already setting in for the majority of the students, as they were entrenched in what looked like just another mundane Wednesday with Sister Ruth. But thanks to one of their fellow students, coupled with their teacher’s strong propensity towards enforced humiliation, this day would be anything but mundane.

The thirty-four year old Sister Ruth had been teaching grammar school for over eleven years. Over the last year or two her job was starting to feel a little stale. The monotony of it all was setting in for her, and she longed for something to spice up her life. She knew she wasn’t going to find that “spice” in the convent, so she often looked to her students for her diversions.

As alluded to, she took considerable pleasure in embarrassing, if not downright humiliating her students. She had recently started using her position of power for that purpose, but up until this point, not quite to the intensity that she yearned for.

There was the time earlier in the year that she punished one of her students by making him stand in front of the room and sing in front of the whole class. She remembered the pleasure she felt watching him blush profusely while singing his song.

Then there was the time she wrapped a woman’s scarf around another boy’s head. Again, she took extreme pleasure as his face grew redder by the second while she slowly tied the scarf under his chin and purposefully adjusted it until she was satisfied. She had conjectured that imposing female clothing on a young man might be one of the more powerful forms of enforced humiliation, and the boy’s extraordinarily embarrassed reaction to the scarf certainly confirmed that supposition.

It had been over a month since she had utilized the scarf punishment, and since then she had been waiting for the opportunity to humiliate one of her students in a similar manner.

Maybe today will be the day, she thought to herself earlier that morning.

So when she spotted Tommy turning around and whispering something to the boy behind him, she decided to pounce on the moment. Little did Tommy know what the consequences would be of the seemingly minor transgression. As it would turn out, he picked the wrong day to make a false step, and he would pay for it to an extent he could never have imagined.


Introducing Sally and Cindy

“Tommy, is there something you’d like to share with the rest of the class?” inquired Sister Ruth.

Tommy blushed slightly at the admonition. “No, Sister Ruth. Sorry, Sister Ruth,” answered Tommy.

A slight smile formed on the corner of her lip. This was the opportunity she had hoped for. “Well, ‘sorry’ isn’t going to be good enough, Tommy. Stand up, please.” Tommy, who was seated in the very front of the second row of students, apprehensively complied. “This isn’t the first time I’ve had to interrupt our lessons because of you, is it Tommy?”

Tommy shifted his weight uncomfortably. “No, Sister.”

In fact, it was quite true. Tommy, though generally a good kid, did have a habit of becoming restless when the subject matter didn’t interest him. Already during this school year Sister Ruth had punished Tommy on three different occasions. The first time he had to write one hundred times, “I will raise my hand before speaking in Sister Ruth’s classroom.”

The second time he had to stand in the corner for an hour, which he found mildly embarrassing.

The third time came on the day of his thirteenth birthday. On this occasion he had to wear a sign on his chest. Sister Ruth made it on the spot, writing in bold and capital letters, “I HAVE BEEN A NAUGHTY LITTLE BOY.” She took pleasure in pinning it on the blushing boy's chest.
The teasing he received from his fellow students was relentless, especially during the recess and lunch periods. Tommy, embarrassed to no end, seemed to have a constant blush going throughout that day.

That experience was more than a month behind him, and he had been very careful not to give his teacher an excuse to embarrass him again, especially in light of the fact that Sister Ruth’s punishments seemed to be escalating in their level of humiliation. When she tied a feminine scarf around the head one of his fellow students Tommy had cringed, and was ever so relieved it wasn’t happening to him. But now he watched his teacher reach into her drawer and pull out the very same scarf. He felt himself literally tremble with fear as Sister Ruth approached.

Oh, there goes Tommy again, talking while I’m trying to teach. I think I’ll have a little fun with him.…yes, he’ll be a perfect little victim.…I’ll bet I can make him blush….ah, he’s already getting a little nervous while I’m reprimanding him.…I think I’ll utilize the scarf….I do love the way they blush when I do this….get it out of the drawer here.…oh, look at him, he’s already turning red.…just wait until I wrap it around his pretty little head.

Uh-oh, she caught me talking.…and she’s got a funny smile on her face.…oh, no, she’s opening the drawer….she’s got the scarf!.…oh, please, no, I’ll just die!

It was at that moment that another student chose to become involved. The student was Tommy’s sister Sally. Tommy had pulled many a practical joke on his slightly older sister, and she had not been amused by any of them. Her intrusion would go a long way toward leading to Tommy’s fateful punishment.
She raised her hand, and Sister Ruth stopped short of Tommy, somewhat annoyed at the interruption. “Yes, Sally?”

“Sister Mary Ruth, I think you should know that Tommy has done something much more serious than just talk out of turn in class. You may well want to consider a harsher punishment when you hear what I have to say.”

Sister Ruth raised her eyebrows. Sally had definitely piqued her interest. In fact, she secretly was hoping to hear of serious misconduct on Tommy’s part, one that might warrant a harsher, even more humiliating punishment.

Meanwhile, Tommy was becoming panicky, as he knew what his sister was about to divulge. The day before, during the morning recess, Tommy was walking by the drinking fountain with one of his friends. Laura, a fellow seventh-grader, was leaning over the drinking fountain taking a sip of water. Tommy, in an attempt to humor his friend, lifted Laura’s skirt, resting it on her back. The two laughing boys scurried around the corner before the startled and embarrassed girl could see who the culprit was. Tommy had thought no one had seen him, but that night his sister said to him, “I know something that will get you in deeeep trouble.” Tommy dismissed it at the time, but now it appeared his actions were coming back to haunt him.

“I’m listening, Sally,” answered Sister Ruth, somewhat anxiously.

“Well, you’ll be interested to know that yesterday Tommy lifted Laura’s skirt up and exposed her panties while she was leaning over the drinking fountain.”

Tommy clenched his eyes shut in anguish. Sister Ruth outwardly appeared riled, but inwardly she was thrilled with the possibilities that were presented to her by the revelation. She looked at Tommy accusingly. “Is this true, Tommy?” she asked with feigned irritation.

“No, it wasn’t me,” Tommy lied, desperate to recover from his increasingly dire situation.
Sister Ruth turned to Tommy’s victim, who was sitting on his immediate right. “Laura, did Tommy lift up your skirt yesterday? It’s okay, sweetheart, you can tell me.”

“I…I…somebody did it, but I didn’t see who,” answered the young, blushing girl truthfully.

It was at this moment that another student chose to contribute to the discussion, an overture that ultimately would seal Tommy’s extraordinarily ill-fated consequences.

The student was Cindy, Sally’s best friend. Cindy was a pretty little blonde girl who sat immediately to Tommy’s left. Tommy had developed an infatuation with her, but she treated him more like Sally’s little brother than as a peer, so Tommy's infatuation was decidedly unrequited.

She had also been involved as a victim in a couple of Tommy’s practical jokes. The two girls had talked about getting back at him on numerous occasions, but so far the opportunity hadn’t presented itself. Cindy, sensing that her immediate involvement would solidify Tommy’s guilt in the eyes of Sister Ruth, raised her hand.

“Cindy, do you have some insight into these distasteful proceedings?” asked Sister Ruth.

“I certainly do, Sister Ruth. I witnessed the dirty deed, also. It was definitely Tommy, and I have to say I was appalled by his naughty behavior.”

She was lying, since at the time of the violation of Laura, Cindy was engaged in a game of volleyball around the corner from the drinking fountain. But Cindy’s fib notwithstanding, Tommy was now in serious trouble.

Sister Ruth wore a look of agitation. “Thank you, Cindy; you have been very helpful.”

She turned to the troubled youth, who was now overwhelmed with dread. “As for you, young man…” She let the phrase dangle there momentarily as she contemplated how she would deal with what for her was a delicious situation. She held the scarf up. “I think, given the gravity of your offense, that we need to come up with a punishment that is a little more creative…..something that would embarrass you more than this.” Tommy’s trepidation increased, while many of the students sat up in their seats, keenly interested in the scene playing out before them. “Yes, I do believe we can find something much more interesting for you to wear.”

Yes! Sally and Cindy’s revelation really opens the door for me.…bless their devious little minds.…so the little perv is lifting up skirts, is he, checking out the girl’s panties?….if he’s so interested in girls’ clothes then I’ve got just the thing for him.…heh, heh….I’ve always wanted to pull out the nighty….forget this scarf.…we’re about to escalate the humiliation.…oh, this is going to be so much fun!

Oh, please, I’ll never talk in class again.…please don’t put the scarf on me.…what does Sally want….oh no, Laura’s skirt.…she’s telling her!….Oh, God, Cindy’s backing her up….I’m in for it now.…what does she mean, something more embarrassing for me to wear?.…worse than the scarf?….oh my God!….what is she going to do to me?


The Nightgown

Sister Ruth smiled to herself. She had already decided on a course of action. Two months before, she had stowed a nightgown in her desk drawer. It was the nightgown that she had worn when she was a young girl. She often fantasized about forcing one of her boy students to put it on as punishment, but up to this point she had never carried out the fantasy. She was concerned that there might be some backlash from the students’ parents if word got out about what some may consider an act of depravity.

But at this particular moment the need to satisfy her prurient desires far outweighed any concerns about possible repercussions.

“Yes, I’ve got just the thing for you, my dear Tommy.”

She stuffed the scarf in the pocket of her habit and walked purposefully to her desk and opened the bottom drawer. She looked over at her frightened subject. "Please remove your shoes and socks," she instructed.

Tommy, now aghast at his increasingly woeful plight, sought to soothe his teacher's displeasure with him. "Please, Sister Ruth, I'm begging you. I'm truly sorry for what I did to Laura. I don't know what I was thinking....I....I was just trying to make my friend laugh. I promise....I've learned my lesson!"

But Sister Ruth was resolute in carrying out her devious plan, and would not be denied.

"I believe you, Tommy. But Laura was violated by your actions and she deserves to see you punished. Now kindly take off your shoes and socks and bring them up here."

While his entertained classmates giggled, the abashed Tommy leaned over and slipped off his shoes and socks, then carried them to his teacher's desk.

Meanwhile, Sister Ruth rummaged through her drawer until she found what she was looking for. When she stood up, to the fascination of the students and to Tommy’s utter distress she was holding a long, pink, flannel nightgown with puffy short sleeves at the shoulders, femininely decorated with a pink, flowery design that was a shade darker than the rest of the nightgown.

She held it up and examined both sides. Seeming quite satisfied, she turned her attention to the cowering barefoot boy standing next to her desk. “Do you know what ‘shame clothing’ is, Tommy?” asked Sister Ruth as she draped the nightgown over her arm and relieved Tommy of his shoes and socks and dropped them in the open drawer.

Tommy frantically tried to extricate himself from his dreadful predicament. “I-I’m really sorry, Sister Ruth; I promise…I promise I’ll never misbehave again. Please, I promise!” His quivering voice betrayed his extreme apprehension.

Sister Ruth wasn’t about to back down. “Answer my question, Tommy. What do you think ‘shame clothing’ refers to?”

The nervous student fidgeted noticeably. “I g-guess it would be…clothing that…clothing that…that would…shame somebody.”

“You are quite right, Tommy. And I’m sure when you are on display in front of your classmates wearing this pretty nightgown, you will feel an extreme sense of shame." Sister Ruth held up the garment. “Here you are, Tommy. I’d like you to go back into the cloakroom, get out of your clothes and change into this,” ordered Sister Ruth.

Tommy was frozen in his tracks. His arms remained at his sides, as he was seemingly too stupefied to move. Sister Ruth used that moment to assert her power and establish her authority. With swiftness reminiscent of Muhammad Ali in his prime, she slapped the stunned boy across the face. The noise of the slap reverberated throughout the classroom, and the sting elicited a well of tears in Tommy’s eyes.

Tommy needed no further persuasion. He reluctantly reached out and took the nightgown from her hands. Sister Ruth continued with her instructions. “Now, I’d like you to go back into the cloakroom and take off all of your clothes, including your underwear. Once you are naked, you’re to slip on your pretty new nightgown, then come out and show off your new look for us.” Sister Ruth looked Tommy up and down and used her imagination to envision the unfortunate lad naked, then in the female attire. She looked at Tommy’s blushing face and was unable to suppress a smirk. “Yes, I’m sure you’ll make quite the pretty little model, don’t you think so?" she teased. She paused momentarily while Tommy fixed his stare to the ground, wallowing in his wretchedness. “Now, if you behave yourself then I’ll let you have your school uniform back in time for the morning recess. Move along now. You’ve wasted enough of our precious time already. I’m sure your classmates are very anxious to see you in your new finery.”

My, the look on his face when I pulled out the nightgown.…like a frightened kitten .…oh, he won’t take it….I’ll show him….I hate to slap him, but he needs to know who’s in control here.…there, I think he gets it now….I’ve got him where I want him.…he’ll cater to any humiliation I choose to impose on him.…I can’t wait to see him in my old nighty.…he has some feminine features, he’ll look just lovely.…and I’m sure he’ll be blushing so.…they blush so much with the scarf….imagine what he’ll look like walking out here in front of all his classmates, wearing a little girl’s pink nighty….oh, this will be delicious!

Oh my God, what is that?.…it’s a nightgown!….a pink one!.…I can’t wear that!.…oh, this can't be happening….she’s trying to hand it to me.…no, I can’t take it.…ow!….she slapped me!….oh, that hurts!.…I have to take it.…oh, God.…I have to go put this on….how can I face my classmates? And I have to take all my clothes off first and be naked underneath? Oh! This can't be happening!

Tommy, his face now fire engine red, turned and walked toward the cloakroom with the nightgown. He walked briskly and averted all eye contact by staring straight down to the linoleum floor. He could hear the giggling and could sense everyone’s stares.

When he reached the cloakroom he threw the nightgown on a table, purposely avoiding looking at it. He was trembling, and the feeling of dread for what he was about to do was overpowering.

He started to unbutton his shirt, but he couldn’t bring himself to begin undressing himself. He stood still for awhile and contemplated. He decided to make a last-ditch effort to maintain a small semblance of dignity. He peeked out from the cloakroom and called out to his teacher. “Sister Ruth, may I at least just put it on over my clothes?”

“You mean you don’t have your clothes off yet, Tommy?” Sister Ruth was now genuinely irritated. “As I said, you’re to be completely naked underneath your nightgown. It’s all part of your shame punishment. You seem to be missing the point. You see, not only will your classmates delight in looking at you wearing a girl's nightgown, they will also know that you’re completely naked underneath the nightgown. We’ll all know that you are just one article of clothing from being completely nude. Imagine how vulnerable that will make you feel, Tommy. Think about it. If you make one false move, if the mood strikes me, I can slip the nightgown right off and have you stark naked in front of everybody in a matter of seconds.” The evil nun paused to let her words sink in. “So it is in your best interests, young man, to do exactly as I say. I’ll give you two minutes, and if you haven’t removed all of your clothing and slipped into your nighty, then I’ll come back there and strip you myself.”

Again Tommy heard the giggling from his classmates as he returned to the cloakroom. He was resigned to his nightmarish fate as he unbuttoned and removed his shirt. He then grudgingly pulled off his undershirt. It was a strange feeling to be naked from the waist up with his teacher and classmates just on the other side of the wall.

He started to unbuckle his belt, but then wavered, and chose to take another path. He would put the nightgown on first. He shuddered as he lifted the feminine garment over his head and slipped it on. He saw his reflection in the full-length mirror and realized how humiliating it was going to be to have to model the nightgown for his classmates and teacher. He reached underneath and slowly started undoing his belt buckle.

“Tommy, you have one minute. Trust me, you don’t want me to have to come in there,” he heard Sister Ruth warn. “If I do, I’ll drag you out here, put you over my knee and warm your bare behind in front of the whole class. Then you’ll really know the meaning of shame.”

The giggling became louder. Tommy needed no further encouragement. He hastily undid the belt and slipped off his pants. He looked in the mirror and saw an image of a red-faced boy wearing a girl’s nightgown. The hem came down to the tops of his knees, leaving the rest of his slender, hairless, white legs exposed. The sight of himself and the feeling of the cold floor on his bare feet caused him to shiver.

He started to reach under the nightgown to remove his underpants, but then hesitated. His sense of shame was already at a high level. To be entirely naked underneath the nightgown was more than he thought he could endure. He did remember being told to remove all of his clothes, but surely, he thought hopefully, he could get away with leaving his underpants on. Besides, she would never know the difference, thought Tommy. She certainly wouldn’t pull up the nightgown to check.

Would she?

Tommy’s level of anxiety was already extremely high, but it intensified as he considered how Sally and Cindy would be reveling in his humiliation. Tommy had cringed when he heard Cindy’s distinctive giggle as he was walking back to the cloakroom with the nightgown.

He knew the giggling would turn into outright laughter in a few short moments. He took in the mental image of walking out there, and he buried his face in his hands at the prospect.

Oh, God.…I can’t believe I have to put this on….I can’t do this…maybe I can at least put it on over my clothes….I’ll ask her….oh, God, I have to be completely naked underneath….I have two minutes or she’ll come back here and do it herself.…I can't let her see me naked, that would be WAY too embarrassing....I have to start stripping.…oh, this is a nightmare....she’s so mean!.…here goes my shirt.…and my undershirt.…brrr….I’ve got goose bumps..…now the pants.…no, I’ll put the nightgown on first in case she comes back here.…I can’t let her see me in my underpants.…oh, look at me in this nightgown.…it smells….smells like perfume.…eww….oh, how can I go out there like this?....it will be unbearable!….oh, I have one minute or she’ll spank me.…on my bare bum!.…how did I get in this mess?….oh, how I wish I never lifted Laura’s skirt.…I didn’t think anybody would see.…I have to take my pants off.…oh, now my legs are showing….I never even wear shorts.…I wish I had hair….it makes me look girlie.…and look how red my face is.…and I’m not even out there yet.…why do I blush so much?….oh, this is terrible.…do I have to take off my underpants?.…she wants me totally bare underneath.…here goes…no!.…I can’t do it.…she’ll never know.…she wouldn’t go that far.…oh, please, don’t let her go that far!.…oh, this is just awful!.…how can I go out there and have them all see me like this?.…especially Sally and Cindy….I know they’re just loving this.…oh, they’ll all be laughing at me.…I’ll never get over this!.…oh!

“Okay, Tommy, time’s up,” announced the nun as another smile formed on her lips. “Please come out and show your classmates how pretty you look.”

It would be hard to top the level of embarrassment of wearing a nightgown.
Perhaps when Tommy's attempt at deception is found out, the wearing of his underwear, seeing panties pulled out next for
him to wear will ramp up the humiliation. Or will it be straight to a naked "Time Out" in the corner?

A fun start to this one.

Hello blondie I was wondering is there anywhere to view all your stories or a portion of them or will it only be the stuff you post here and at the pace you decide to post them, thank you

Massive fan of your work

Answerlife75 wrote: ↑Fri Dec 08, 2023 3:02 am Hello blondie I was wondering is there anywhere to view all your stories or a portion of them or will it only be the stuff you post here and at the pace you decide to post them, thank you

Massive fan of your work

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.

Chapter 2: Nightgown Up, Underpants Down

Taunted in the Nightgown

Back in the cloakroom, Tommy could hear the buzzing emanating from the students. With considerable trepidation he poked his red face out and saw the faces of thirty-five students (twenty-one girls and fourteen boys) and one teacher staring back at him with looks of anticipation. He quickly retreated and leaned against the wall, closing his eyes. He braced himself and finally emerged, looking straight down and making a beeline for his desk.

Laughter filled the room as the students took in the extraordinary scene. Tommy walked briskly up the aisle, just wanting to crawl into the seat of his desk to secure at least a minimal amount of relief. When he arrived at his desk in the front of the second row he quickly sat down and self-consciously put his knees together, pulling the hem of the nightgown toward his knees as best he could. He couldn’t help but to turn and steal a glance at his “audience,” and he wasn’t surprised to find his gaze answered by a host of grinning faces.

He blushed brightly as he caught Cindy’s eye. She was obviously enjoying the moment. He glanced up at Sister Ruth and noticed that she was smiling broadly to herself—she seemed to almost be glowing in her state of pleasure.

Indeed, Sister Mary Ruth was in her glory. She always knew she had a dominant side, with a strong bent for humiliation, especially involving the male gender. And here she had a thirteen-year-old boy completely under her control. Not only that, it was Tommy, whom, given her choice she would have picked over any of her other students to play victim to her deviant desires. She was getting an extra thrill out of humiliating the innocent looking, slender, blond-haired, baby-faced and blue-eyed boy. She felt a stimulation in her loins that she hadn’t felt in some time, and there was no telling to what extreme she would pursue her sordid fantasy. She knew full well that she could get herself into serious trouble, to the point of being dismissed from the convent—or even worse.

But her prurient desires were inordinately seductive, and superseded any concerns of the potential consequences of her actions. Instant gratification was in the offing, and she certainly was going to make the most of her opportunity.

“Tommy, could you please come up here so we can have a good look at you in your shame clothing?” invited Sister Ruth. The abashed Tommy hung his head as he trudged to the front of the classroom. He stood facing his nemesis. Sister Ruth took his hands in hers and reveled in his blushing, downcast face. “You look lovely in your new nighty, Tommy,” teased his teacher. “And you smell so nice, too.” She paused to look Tommy up and down before continuing. “You know, I used to wear this very nightgown when I was a little girl, but I don’t think I looked nearly as pretty in it as you do right now.” Tommy heard the giggling behind him, and turned yet redder under the taunting from the nun. “And you’re blushing so much, Tommy, that your face matches the bright pink flowers on your gown. I think we should share this with your classmates, don’t you?”

With that she pulled his hands around until he had turned to face his peers. She let go and walked a full circle around him, eyeing him up and down and smiling broadly. She left him standing there feeling his shame, as his classmates soaked up the unusual spectacle. Tommy stood and absorbed the humiliation, looking straight down and fighting off tears.

“You may return to your seat now, Tommy, and if you behave yourself I’ll take your nighty back at 9:45.”

Tommy returned to his seat and glanced at the clock. It was 9:15, so he would only have to endure the agonizing experience for another half hour. There was no way he would do anything to jeopardize his fate at that point.


Missing Underpants

Sister Ruth had already decided that Tommy was not going to get his clothes back, though, and she found the perfect justification to deny him. When she had taken hold of his hands she had inadvertently brushed her fingers against his sides and had felt the unmistakable outline of his underpants. She decided right then and there to take full advantage of Tommy’s disobedience.

She let a couple of minutes go by before taking her next step. She called on one of the students in the back of the room. Not coincidentally, she picked Tommy's sister. “Sally, would you do me a favor and go back to the cloakroom and retrieve Tommy’s clothes for me?”

Tommy stiffened in his seat. He wasn’t sure what his teacher had in mind, but he didn’t have a positive feeling about the direction that things were heading.

Momentarily Sally emerged from the cloakroom with Tommy’s clothes and sauntered up to the front of the room.

“You can lay them on my desk, Sally.” Sally complied and looked over at her brother. She grinned as she turned and returned to her seat. “Thank you, Sally,” said Sister Ruth.

Sister Ruth began sifting through Tommy’s clothes. She picked them up one by one and set them aside, forming a new pile. For effect, she had a confused look on her face and again picked each article of clothing up one by one. Tommy’s heart raced as he realized what his teacher was up to.
“Sally,” asked Sister Ruth, “Are you sure you brought all of Tommy’s clothes up here? We seem to be missing his underpants.”

“I’m sure,” responded Sally. “I didn’t see Tommy’s underpants back there." After a pause, she volunteered, “Maybe he’s still wearing them, Sister Mary Ruth.”

Sister Ruth glared at Tommy, who had a panicked look on his face. Then he had an idea. “I know where they are, Sister Ruth, I’ll go get them.”
Tommy rose from his desk as if to run back to the cloakroom.

“You stay right where you are, young man! Sally will get them for you if you just tell her where they are.” She was enjoying herself as she watched Tommy fidget anxiously. “Well, what did you do with them, Tommy? Did you hide them? You’d better not be lying to me, young man. You’re already in enough trouble as it is. Now tell us where your underpants are.”

Tommy’s situation was hopeless. He had to confess before digging an even deeper hole for himself. Looking downward, he spoke softly. “I’m still wearing them.”

“You WHAT?” exclaimed Sister Ruth, feigning incredulity. “Did I or did I not tell you that you were to be naked under the nightgown?” Tommy was silent. “Answer me, young man. What does the work 'naked' mean to you?”

“I didn’t know you meant my underpants, too, Sister. I’m sorry. I’ll....”

"You didn't answer my question," she interrupted. "What does the word 'naked' mean to you?"

"It means....no clothes," Tommy answered quietly.

"Yes!" answered Sister Ruth. "No clothes. And yet apparently you are not naked under your nightgown."

Tommy desperately tried to find a way out of his predicament. "I'll take them off right now if that's what you want."

“It's way too late now," she answered. "You’re in hot water, buster. Come up here right now.”


Underpants Exposure

Tommy, head bowed, walked up to the center of the room where he again faced his teacher. “What am I going to do with you, Tommy? First you disobey me and then you lie to me. Well, I guess making you wear this nightgown wasn’t shameful enough for you. So here’s what you’re going to do: Since you think so highly of your underpants, I think it’s only appropriate that you show them off for your classmates.” She reached down and grasped the hem of the nightgown with each of her hands “Raise your arms up in the air.” Tommy’s jaw dropped, and he was too dumbstruck to move a muscle. “Get your arms up, or I’ll slap your face even harder this time!” commanded Sister Ruth. Tommy, remembering that experience all too well, shot his arms straight up. Sister Ruth promptly lifted the hem of the nightgown, pulling it inside out and draping it over Tommy’s outstretched hands.
A collective gasp, followed by loud giggling emanated from the students, as Tommy’s underpants were completely exposed. The nightgown was inside out over Tommy’s head and the remaining material drooped halfway down his chest, just below his nipples.

Since his eyes were covered Tommy couldn’t see Sister Ruth grinning at what was for her an entertaining sight. He couldn’t see her scrutinizing the small, nearly non-existent protrusion in his white briefs and grinning even wider. He couldn’t see her walk the full circle around him, inspecting him from every angle. But he could feel the cool air on his stomach and thighs, and he could certainly hear the giggling from his classmates. He felt his face flushing as he stood there, exposed and helpless.

Sister Ruth lifted out the front of the upturned nightgown just enough to poke her head in and made eye contact with the red-faced, agonized Tommy. “Are you happy now, Tommy, with your decision to disobey me and keep your underpants on?” Tommy shook his head back and forth. “I thought not. But I can tell you, your classmates are happy with your decision, judging by the expressions on their faces. They obviously find your exposure highly entertaining. Would you like to give them a frontal view of your underpants now?” Without waiting for an answer, she lowered the gown back down to his chest and turned him by the shoulders towards the students. Tommy listened to the renewed laughter and felt his face flush yet brighter. In one respect he was relieved to be hiding his blushing face, but in another way the awkward feeling of being on semi-naked display without being able to see anything somehow added to his humiliation.

Oh, here he comes.…my, would you just look at him!.…a sight for sore eyes….his face is even pinker than the nighty.…how adorable…this is so much better than the scarf….I’ll have fun teasing the poor lad.…let’s get him up here….yes, this is delightful.…I’m glad I sprayed the nighty with perfume.…he gets to experience his humiliation even with his sense of smell….he’s ideal for this.…baby-faced, blond, slender.…delicate features.…and look at him blushing so brightly….this is wonderful!.…my, I’m getting a little hot and bothered.…I might have to put him through his paces today.…an opportunity of a lifetime.…you’ve been waiting a long time for this, Ruth….like I tell my students, carpe diem.…let’s turn him around so his friends can see his blushing face.…wait!….what’s this I feel?.…the little rascal left his underpants on….thought he could pull one over on me.…thank you, my little pet….that’s just the excuse I need.…we’ll just have to step up the humiliation another notch.…is it getting warmer in here?….no, it’s me…....let’s take it slowly, Ruth.…have some fun with this….okay, I’ll send him back to his seat.…I’ll get Sally to bring his clothes up here.…yes, he’s fidgeting a bit already, wondering what I’m up to.…I’ll toy with him for a bit.…go through his clothes one by one….oh, he’s sweating now….it’s time, my frightened one, you’ve got no way out of this….time to ‘fess up.…that’s it, now come up here and let’s have some fun with you….you can show off your precious undies to us….oh, I’m actually trembling.…this is so exciting!….get those arms up….look at him, he’s trembling, too.…for a different reason.…up it goes….just drape this over his hands….perfect….oh, what a treat this is.…look at the tiny bulge in his undies….poor little lad, it appears he’s been deprived in the penis department.…all the more embarrassing for him, I suspect.…and even more fun for me....let’s take a little stroll around the poor wretch.…look how nice and smooth his legs are….I’ll bet he’s like this all over.…we’ll soon find out, won’t we?.…take it slowly.…enjoy the moment.…I think I’ve died and gone to heaven….and this is just the beginning.…there’s no turning back now, Ruth….you’ll never get a chance like this again.

Oh, God….I’ve got to go out there….I’ll make a run for it….here I go….oh, listen to them laughing.…oh, this is awful.…here’s my seat.…pull this nightgown down….oh, it doesn't even reach my knees.…they’re all grinning and laughing….look at Cindy….I’ve never seen her laugh so hard….oh!.…and look at Sister Ruth, just standing up there and smiling at me.…just do the English class, would you?.…oh, no, she wants me to come up there.…here I go.…she won’t stop teasing me.…oh, no, she’s turning me around to face them.…oh, my face is so hot!….Sally, she’s grinning so evilly.…looks like the devil….I can always hear Cindy over everybody….Sister Ruth is walking all the way around me, grinning.…she’s really enjoying herself….I never knew she could be so mean….I’ve got to keep from crying.…please, just let me sit down.…oh, thank you.…I get my clothes back at 9:45….just a half hour.…oh, I can’t wait….just sit here quietly and it’ll be over…wait!….why is she sending Sally for my clothes?.…oh, I don’t like this at all!….she’ll notice my underpants aren’t there!.…oh, why didn’t I take them off?….I just couldn’t….she’s going through them.…I think she notices already….how did she know?….oh, God, I’m in trouble.…she’s going through them again….oh, Sally’s trying to get me in trouble….I hate her….what can I do?….I know, I’ll run back there, take them off and act like I’m finding them.…yes!.…oh, no, she won’t let me.…I’m in for it now….Oh, God, she wants me to come up there again.…what will she do to me?.…oh!.…she’s lifting up the nightgown!….no!….she wants me to raise my arms.…I just can’t!.…oh, she’ll slap me….gotta do it.…oh, she’s lifting it way up, over my arms.…they can see my underpants!….oh!….I can’t believe this!.…listen to them!.…how can I ever face them again?….oh, she’s turning me around to face them!.…this is awful!….this is so weird.…I can’t see them, but I know what they can see….my underpants!.…they’re laughing so hard….oh!


Underpants Hauled Down

Sister Ruth turned Tommy back around so he was facing her again. “I think we’ll proceed with our English lesson now, class,” Tommy heard her say. It appeared as though he would have to stand there as the centerpiece while English class continued.

“How would you diagram this sentence, class?” Tommy could hear her writing on the blackboard, and then heard the tittering from the students behind him. “Cindy, would you please read this sentence aloud for us?”

Tommy heard Cindy giggle before reading from the board. She read it loudly and clearly. “The naughty student disobeyed and then he lied, leaving his teacher no choice but to pull down his underpants....<giggle>....in front of the whole class.”

Sister Ruth noticed Tommy’s body tense up and his knees clench together when Cindy finished the sentence and the realization of what was about to unfold set in. Her heart raced with excitement. A most humiliating stripping was imminent, and it was all she could do to maintain her composure, such was her state of stimulation.

“Tommy, you’re standing there exposing your underpants because you disobeyed me and didn’t take them off like I asked you to,” explained Sister Ruth. “Then you lied to me about it, so you must be punished.” Tommy felt her hands on the elastic band of his underpants. “Don’t you dare lower your arms while I take these down.”

“No! No! Please, you can’t!” came the muffled cry from inside the nightgown.

“Ah, but I can, my dear boy,” responded the titillated Sister Ruth. She bent down to one knee and, still holding on to the elastic band, she paused momentarily to savor the moment. She looked up at her trembling victim, then to the open-mouthed, wide-eyed students, and then back to the pair of underpants that was the focus of everyone’s attention.

“Dowwwwwwn they go!” she declared, and in one continuous, fluid motion she lowered Tommy’s underpants all the way to his ankles.

As she stood up, Sister Ruth could barely hear Tommy’s cries of anguish over the uproarious reaction from the students, and she could tell by the heaving from his stomach that he was breathing hard and fast—almost hyperventilating—while his weight shifted rapidly from one foot to the other.
She grinned to herself as she took a few moments to take pleasure in the scene she had created—that of a prepubescent thirteen-year-old boy standing before her with a nightgown turned inside out over his head and his underpants bundled at his ankles. She imagined his intense feeling of humiliation and smiled wider.

She bent down and lifted Tommy’s right leg while freeing his underpants from his foot. “You won’t be needing these now. No more boy clothes for you for awhile.” She repeated the same maneuver on his left leg, then took the underpants to the chalkboard, spread them out and fastened them with two clamps that were normally used for hanging posters. Tommy's underpants were on full display, dangling whimsically for everyone's amusement.

Meanwhile, Tommy was beside himself over the devastating turn of events. A few moments before his underpants were exposed to his classmates. Almost before he could digest his disgrace he felt icy fingers on the inside of his waistband and suffered the ignominious experience of having his underpants hauled down by his sadistic teacher. Panicky, he cried out some unintelligible sounds that were somewhat muffled by the nightgown, and to a greater extent by the robust reaction from the astonished and entertained students. As he stood there he could only imagine what a vision he must be, his naked ass fully exposed to all of his classmates, while his teacher was soaking up a frontal view that even his own mother hadn’t seen in at least five years. Then, just as disconcerting, he felt his teacher lift his legs one by one and remove his underpants completely.

He stood there for what seemed to him an interminable amount of time, mortified beyond comprehension. When the noise subsided he felt a hand on his shoulder and felt his teacher’s mouth touch his ear through the flannel material. “You’re putting on quite a show for everybody, Tommy,” teased the devilish nun. “Can you believe you’re almost naked in front of the whole class? All of your classmates are staring at your bare bottom and I can see your naked little wee-wee.”

“Oh! Oh please!” was all the agonized Tommy could muster.

“How humiliated you must feel right now,” she continued. There was no response from her most unfortunate victim except his rapid, heavy breathing. The depraved nun basked in her state of delectation. She let the scene play on for a few moments before continuing. “Would you like to turn around and face your classmates?” She gently tried to turn Tommy around by his shoulders and felt his body stiffen as he strongly resisted the overture. She afforded herself another smile. “Well, I see you are still defying me, Tommy. You’ll pay for that later. For now, though, it’s time you show us your shamefacedness. You can put your arms down now.”

The underpants have to come down, no question about it.…he’ll be shocked, and thoroughly humiliated.…plus it will be such a lovely sight.…now, how shall I go about it?.…maybe I can involve one of the students in some way….like his little friend Cindy….oh, I’ve got it.…she can read out loud what will happen, right before I haul them down.…I just love my creativity sometimes.…just write this on the board….oh, listen to them, they’re tittering already.…okay, Cindy, read it and watch him weep….oh, look at him tense up.…the realization has set in….that’s right, my little friend, brace yourself….it’s about to happen….easy, Ruth.…control yourself.…savor the moment.…oh, the delicious anticipation.…there's nothing like it….okay.…now!…dowwwwwwn they go!….oh!.…too precious!.…I was right, there’s not much there.…even smaller than I thought.…poor little wretch….and he’s smooth all over.…not even any peach fuzz.…he’ll just die if I let his classmates see this….in due time.…let this play out for a bit this morning first.…he must be absolutely mortified right now.…can you imagine?….I wish I could see his face….I’m sure it’s red as a beet, with a horrified expression….look at him squirming….and his stomach heaving back and forth.…I hope he doesn’t hyperventilate.…okay, let’s get these undies completely off.…I’m sure he’ll enjoy this.…oh, look, he felt me breathe on him and flinched his hips….this is all so delicious….okay, let’s get that leg up….good, now the other leg….excellent….it’ll be well into the afternoon before he gets these back.…let's see, why don't I hang these up....just for fun....clip them up right here....now his little undies are on full display for all to admire....how delectable....he won't be wearing any of his boy clothes for some time....I’ll have him wear the girls’ uniform for recess….I’m sure he’ll love that.…what a delight.…it’s either petticoat discipline or enforced nudity for the rest of the day….a win-win situation if there ever was one.…but first things first.…I think I’ll tease him for awhile.…then I’ll have him drop his clothes out the window….I can’t wait to see the look on his face when I have him do that.…and pretty soon I’ll have him naked as the day he was born.…oh, I can’t wait!


Clothes Dropped Out the Window

Tommy lowered his arms and the nightgown came down with them, the hem dropping back down below his knees. Sister Ruth smiled at the glowing red face of the tormented boy before her. “Okay, Tommy, you may go back to your seat now.” Tommy, though still shaking from the ordeal, was grateful to be able to escape to the relative sanctuary of his seat. “Oh, but before you do I’d like you to gather up all of your clothes from my desk.…” Sister Ruth paused, and Tommy breathed a sigh of relief as he picked up his beloved clothes from his teacher’s desk. But she wasn’t finished.
“.…and drop them out the window.”

She watched the startled boy’s horrified reaction as he stopped in his tracks, looking at her dumbfounded. He was sure he must not have heard her correctly. “Don’t worry, if you behave yourself for the next hour I’ll go down and get them for you before the morning recess. Now don’t waste any more of our time—do as I say.”

The distraught youngster had no other option but to obey the outrageous directive. To his chagrin and to the amazement of his classmates, he walked with his bundle to the side of the room and, after a moment of hesitation, dropped his clothes through the open window. He longingly watched them settle on the ground three stories below.

Sister Ruth smiled in satisfaction. “Thank you, Tommy, now please take your seat so we can begin our history lesson.”

In your first story posted here, the fourteen year old is a "late developer".
In this story Tommy, who is thirteen, has yet to begin his growth spurt.

These are not SPH stories, as these boys probably reach normal, typical size once the puberty monster finally gets hold of them.

Do your stories typically use an underdeveloped character? Or do you have some stories where a boy is "Big" for his age, more developed
than other boys in his class?

Another question: Do all your stories fit the CFNM category, or will there be a naked girl here and there?

____________________

Great second chapter. Considering there are only 30 more minutes left in the class period, it won't be long till poor Tommy has to lose his
nightie as well. English class with be combined with Human Anatomy...or perhaps call it Art Class, and Tommy is the first volunteer to be a nude
model.

TeenFan wrote: ↑Fri Dec 08, 2023 3:26 pm In your first story posted here, the fourteen year old is a "late developer".
In this story Tommy, who is thirteen, has yet to begin his growth spurt.

These are not SPH stories, as these boys probably reach normal, typical size once the puberty monster finally gets hold of them.

Do your stories typically use an underdeveloped character? Or do you have some stories where a boy is "Big" for his age, more developed
than other boys in his class?

Another question: Do all your stories fit the CFNM category, or will there be a naked girl here and there?

____________________

Great second chapter. Considering there are only 30 more minutes left in the class period, it won't be long till poor Tommy has to lose his
nightie as well. English class with be combined with Human Anatomy...or perhaps call it Art Class, and Tommy is the first volunteer to be a nude
model.

Yes, I do often (mostly, when writing of boys of a certain age) write humiliation stories involving “late bloomers.” It just seems to me that they would be more self-conscious about their bodies, and therefore even more embarrassed when stripped naked. I try to exacerbate the humiliation level when possible. I have occasionally used a boy with a larger than average penis. When I do it is usually to add to the embarrassment of the lesser endowed male when comparing the two.

My stories are probably about 70% ENM and 30% ENF. I have already posted a story entitled “The Satanic Psychiatrist” in the ENF section.

Quite prescient of you in your Human Anatomy prediction. Stay tuned for a later chapter.

Sorry to pester with another question.
I guess I wasn't clear enough before. Do your ENM stories also have one or more girls getting naked in the same story, a mix of both?

Often what I do is use semi-clad girls to keep the embarrassed boy at a high level of arousal. The boy is humiliated in part because he
sometimes can't keep his body parts under control, and a girl topless can add to his problems. That is what I meant by having girls naked in
your story. The same question for a story that is basically an ENF one at the ENF section.

In Neverdoubted's story about DARE ME, there is a chapter where the brother is naked the whole time.
Just wondering what will be in your upcoming story postings.

Off the top of my head I can’t remember having a girl naked in any of my ENM stories, but I do like the idea and will keep it in mind for future stories.

There are a couple of occasions where a girl, though not naked, is dressed rather sexily and uses that, as you say, to keep the embarrassed boy at a high level of arousal. In fact, as you will see (much) later in “Tommy’s Debasement,” that is exactly what takes place.

I have written at least two stories with several chapters where, in a predominately ENM story there are a couple of chapters featuring ENF, and vice versa. But that’s not what you’re referring to.

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