Tommy's Debasement

Tommy's Debasement

Status: Finished

Genre: Erotica


Status: Finished

Genre: Erotica


A young teenager endures the humiliation of a lifetime at the hands of his sadistic teachers and classmates (mostly female).


A young teenager endures the humiliation of a lifetime at the hands of his sadistic teachers and classmates (mostly female).

Chapter1 (v.1) - Chapter 1: Shame Clothing

Chapter Content - ver.1

Submitted: January 27, 2020

Reads: 2213

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Chapter Content - ver.1

Submitted: January 27, 2020



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. For 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 now, not quite to the extreme that she desired.

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 would 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.
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.” 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 use 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 towards 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. She was now suddenly quite interested. In fact, she secretly was hoping to hear of serious misconduct on Tommy’s part, one that might warrant a severe, 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 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.
It was at this moment that another student chose to contribute to the discussion, an overture that ultimately would seal Tommy’s miserable fate. The student was Cindy, Sally’s best friend.

Cindy was a pretty little blond girl who sat immediately on Tommy’s left. Tommy had always had a crush on her, but she treated him more like Sally’s little brother than as a peer. 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.
“Yes I do, Sister Ruth. I saw the dirty deed, too. It was definitely Tommy.”

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 a little more embarrassing 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 nightie…forget this scarf…we’re about to escalate the humiliation…oh, this is going to be 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, God!…what is she doing?
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 she never had 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 her concern about any possible repercussions.
“Yes, I’ve got just the thing for you, Tommy.”

She stuffed the scarf in the pocket of her habit and walked purposefully to her desk and opened the bottom drawer. 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 darker pink flowers.

She held it up and examined both sides. Seeming quite satisfied, she turned her attention to the cowering boy standing next to his desk.

“Do you know what ‘shame clothing’ is, Tommy?” asked Sister Ruth.  
Tommy frantically tried to extricate himself from this most disconcerting 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 apprehension.
Sister Ruth wasn’t about to back down.

“Answer my question, Tommy. What do you think ‘shame clothing’ refers to?”  
“I g-guess it would be…clothing that…clothing that…that would…shame somebody.”

The nervous student fidgeted noticeably.
“You are quite right, Tommy. And I’m sure when you’re on display wearing this nightgown for the class you will feel an extreme sense of shame.”

Sister Ruth walked over to where Tommy was standing and held out the garment for him.

“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 too stupefied to move.

Sister Ruth used that moment to assert her power and establish her dominance. 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.

It was obvious to Tommy that his teacher meant business. Tommy grudgingly 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. When you’re 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 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 stings…I have to take it…oh, God…I have to go put this on…how can I face my classmates?
Tommy, his face now fire engine red, turned and walked towards 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 stepped 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, the whole class will know that you’re naked underneath your 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 a matter of seconds.”

The evil nun paused to let her words sink in.

“So it is in your best interest, 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 nightie, then I’ll come back there and strip you naked 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 partition.

He reached down and pulled off his loafers and his socks. 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 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…here go the shoes and socks…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.”

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