Chapter 11: Sisterhood of Humiliation
Reminiscences of Humiliations Gone By
During the lunch period Sister Ruth spent most of her time gazing out her window. Her view was of the girls’ play yard, and she was enjoying the entertaining scene of the girls tormenting Tommy.
She reminisced back to her own days when she was in the seventh grade. She had a teacher who, on two different occasions, employed humiliation as a form of punishment. She smiled to herself as she looked back fondly at the memories.
On the first occasion the teacher forced a boy student to stand up in front of the room while she slipped a frilly pinafore over his clothes. She remembered the strange tingling she felt while taking in the lad’s profusely blushing face. She had let her imagination run wild at the time, wondering how embarrassed he would have been if the teacher had made him put on a short skirt and slip on a pair of panties underneath. Her feeling of stimulation at the time was her first inkling of her predisposition toward the enjoyment of enforced humiliation.
Later that year, another one of the boys misbehaved in class. The teacher called the boy to the front of the room. She had a ruler in her hand and asked him to hold his hands out. When he refused, she was so furious that she overpowered him by putting him across her knees, pulling his pants and underpants down to his knees, and giving him a hard, bare-bottomed spanking in front of the whole class. He was then made to go stand in the corner for the rest of the period with his pants and underpants still bundled around his knees and his shirt pulled up to his shoulder blades.
Sister Ruth remembered how she felt when the teacher lowered the kicking lad’s pants. The first glimpse of his exposed derriere had sent a wave of pleasure throughout her body. She remembered wishing that her teacher had stripped all of his clothes off and humiliated him even further. Again she let her imagination go, and envisioned the mortified student being forced to spend the rest of the day naked in class. She recalled being flushed with excitement when she imagined that she was allowed to take charge of the naked boy herself, and inflict all sorts of her own degradations on the poor wretch. She recalled fondly going home that afternoon, lying on her bed and pleasuring herself over that very fantasy, ultimately bringing herself to an orgasm for the first time in her young life. At that point she realized that she had strong, dominant humiliation tendencies, with a burning desire to force a boy to strip naked against his will. In the years since she has spent many a moment closing her eyes and fantasizing about having her own victim at her mercy, to strip and humiliate him as she pleased.
But she had never acted out on her deep-seated predilection—until today. And she was deriving even more pleasure out of the day’s events than she had ever imagined.
She sighed as she realized that her living fantasy would soon come to an end. Class resumed at 1:00, and at 2:00 there was the dance class with Miss Richards. She knew she couldn’t let Betty Richards find out about her sordid dealings, so she’d have to give Tommy back his clothes. But what in the devil had happened to them?
Introducing Betty Richards
Just then she was interrupted by a knock on the door. It was none other than Miss Richards.
“Hi, Betty, please come in.”
Betty Richards was a tall, slim, young, attractive brunette. Just about every boy from the sixth grade on up had a teacher’s crush on her. One of her responsibilities was to teach dance class. Most of the boys didn’t much care for dancing, but having the beautiful Miss Richards as their instructor made it tolerable.
“Good afternoon, Sister,” greeted Betty Richards. She was carrying a small duffel bag.
“What can I do for you, Betty?” asked the curious Sister Ruth.
“Well, I have something here that I believe belongs to one of your students.” She laid the bag on the desk, unzipped it, and, to Sister Ruth’s horror, took out Tommy’s clothes one by one and laid them out on the desk. The last article she removed were his pants, which she held up in the air while staring at the dumbfounded nun before letting them drop to the desk.
“As you may know, Sister, I teach playacting in the second floor room right below you. Well, at about 10:00 this morning, with my peripheral vision I saw some items cascading by the window. I looked down and saw a boy’s uniform, complete with shoes and socks. It could only have come from your room." She looked up at the pair of white underpants which hung incongruously from the chalkboard. In her current state of excitement, Sister Ruth had completely forgotten that they were still hanging there.
Betty Richards smiled wryly. "Then at recess I saw Tommy Dunlop wearing a girls’ uniform. I put two and two together and figured that you must have divested him of his clothes. When it was time for recess, you couldn’t risk sending him out like that—though I suspect that’s exactly what you would have liked to have done. Since I had already picked up his clothes, you improvised with a girls’ uniform. Am I right, Sister?”
Betty Richards was looking her right in the eyes when she made the accusations, and it was Sister Ruth’s turn to blush. “L-let me explain, Betty,” she stalled.
“There’s nothing to explain,” she said, smiling. “I just want you to know that I’ve been quite envious of you all morning. I’ve had this marvelous image in my head of you having a young, stripped teenage boy at your beck and call, putting him through God knows what sorts of humiliations, while I was stuck showing a bunch of fifth graders how to play their parts in the upcoming Snow White school play.”
Sister Ruth started to smile, and it gradually turned into a grin as it sunk in that Miss Richards shared her deviant humiliation tendencies. “You mean you’re not going to turn me in?”
“On the contrary, Sister,” smiled Miss Richards. “I do have a favor to ask of you, though.”
“Sure, how can I help?” The relieved Sister Ruth stared at her associate with interest.
“Well, as you know, I have the seventh and eighth graders for dance at 2:00. I was wondering if we could work something out. Do you think it would be possible for me to.…how shall I put this….continue the lad's humiliation for my own pleasure?”
Sister Ruth was beside herself with delight, and smiled wickedly. “No problem, Betty, he’s all yours!” Sister Ruth paused momentarily, her mind racing with excitement. “But now I have a favor to ask of you. Would you mind terribly if I sat in on your class? I’m having a glorious time with Tommy’s….‘debasement,’ if you will, and I’d hate to miss out on whatever you might have in store for him.”
“It’s a deal, Sister.” She smiled and said, “After all, it appears that we’re two birds of a feather. You could say that we’re the charter members of the ‘Sisterhood of Humiliation.’”
The women shared a laugh over the declaration. Betty leaned against the edge of the desk, bending slightly at the waist toward her counterpart. “You
must fill me in on your exciting morning.”
Sister Ruth’s Recap
“Oh, Betty, you wouldn’t believe it. I had the poor boy blushing so brightly that I thought his face would catch fire.”
“Oh, pray tell, pray tell!” urged Betty eagerly.
“Well, for starters, I made him.…I don’t know how much time you have. Would you like the long version or the condensed version?”
“Oh, please, I want details.…all the details!”
Both women laughed again. Sister Ruth reached into her desk drawer and pulled out the nightgown, holding it up for her colleague to see. “When I found an excuse to punish him, I had him put this on.”
“Oh yes, the old ‘shame clothing’ punishment,” Betty beamed. “A favorite fantasy of mine,” she said with a chuckle. “And one I’ve used on more than one occasion. It’s such an effective form of punishment, because they really are terrified by the concept of enforced feminization. I relish the spectacle of the boy recoiling in fear when I pull out the pretty pink bow from my desk drawer. And the sight of his blushing face when I pin it to his head is absolutely breathtaking.” She smiled to herself while summoning up the image of her most recent unfortunate. “But I’ve interrupted you, Sister. Tell me, was he wearing anything underneath?”
“He was, but not for long,” laughed the evil nun. “I sent him to the coatroom and told him under no uncertain terms that he was to be naked underneath the nightgown. But the little rascal kept his underpants on. Well, that was a blessing, since I was able to use his defiance as a means to further his shame.”
Betty Richards’ interest was piqued. “Do continue!” she prompted enthusiastically.
“So I called him up to the front of the room and had him lift the nightgown over his face and show off his underpants to the class.” The nun was thrilled to be recounting the events, and her listener’s obvious fascination bolstered her enthusiasm.
"Oh, what a wondrous scene that must have been!" said Miss Richards.
“Yes, indeed it was. Anyway, I decided right then and there that his underpants were coming down. He just looked so vulnerable, I couldn’t help myself!”
"Of course you couldn't," laughed Miss Richards.
Sister Ruth paused for a moment and smiled at the recollection. “If I do say so myself, I was quite creative in the tactic I used to take them down. I was teaching the class how to diagram sentences, and I had one of the girls read that out loud.” She pointed to the chalkboard, and Miss Richards read the words, “The naughty student disobeyed and then he lied, leaving his teacher no choice but to pull down his underpants in front of the whole class.”
Miss Richards broke into a wide grin. “Oh, you devil, you! So please tell me you did the dirty deed yourself.”
“I most certainly did, and I’m here to tell you it was exquisite. I couldn’t see his face because the nightgown covered it, but I could hear him cry out above the ruckus his classmates were making, and he was shuffling his weight back and forth from one foot to the other….”
“Oh, Sister, I have to tell you, the image I have of the poor lad, squirming in naked shame.…how wonderful! Please, go on. What happened next?” she asked anxiously.
“Well, I kneeled down and pulled his underpants free from his feet. I guarantee you he was taken unawares before it hit him that I wasn’t stopping at taking his undies down, but that I was stripping them completely off….”
“Oh, how delightful!” chimed in Miss Richards. “I'm sure he was quite chagrined!"
Sister Ruth smiled and nodded zealously. “Oh, and you’ll like this. While I was down there, my face was unavoidably close to his cute little penis.…and it is very little, as you hopefully will see for yourself this afternoon….<giggle>” The grinning Sister Ruth held her thumb and index finger out, less than an inch and a half apart. She paused while Betty Richards tilted her head back in laughter.
“Oh, the poor little dear,” she quipped. “How delectable! And that had to intensify his humiliation.”
“Oh, most definitely. Anyway, I made him aware of my close proximity to his bare privates by breathing just a little heavier than normal. I know he felt it, because he contracted his hips.”
“Oh, I appreciate the details. What an extraordinary scene! Then what happened?”
“Well, after teasing him for a spell I allowed him to let the nightgown drop back down. I must say, the look of wretchedness on his face was something to behold. Then I told him to drop his clothes out the window. His expression of disbelief was priceless.”
“I’ll bet! Obviously, he obeyed,” she said, pointing to Tommy’s clothes.
“Reluctantly, yes. Then, after he took his seat I waited a couple of minutes before dropping the bombshell.” She paused, and was delighted in her cohort’s look of anticipation. “By the by, at some point while he was standing there half-naked with the nightgown over his head, I had decided that there was no turning back, that I wasn’t about to get this far in the game without stripping him completely nude.”
“Of course! How could you
not strip him naked after all that?” laughed Miss Richards.
“Thus the bombshell. I informed him that the ‘shame clothing’ portion of his punishment was over, and that he could hand over his nightgown. First there was the look of bewilderment, and then, when the ramifications of my statement set in, when he realized that would render him stark naked.…his eyes widened, and his jaw dropped….oh, it was precious, Betty.”
“I can only imagine! Did he hand over the nightgown?”
“No, he resisted. I mean, can you blame him? <giggle> It took a bit of ‘persuasion,’ but I stripped it off of him myself. I had the poor dear standing before me in short order, naked as the day he was born. I’m here to tell you, it was a delicious sight, Betty, watching him standing there naked and squirming, desperately covering his privates with his hands. I think he was red from head to toe, and the students’ animated reaction only added to his torment. You know how self-conscious they are at that age about their bodies. And this one is at least a couple of years on the shy side of puberty, a point I made sure to call attention to later on.”
“Oh, you really do have a wicked streak, Sister Ruth. I love it!”
“<Giggle> Thank you. And please, just call me ‘Ruth.’ Anyway, I told him to face me and put his hands behind his head. He was reluctant, but I think he understood that he was going to do my bidding one way or the other, and he eventually relented. He was quite exposed now, and of course the poor lad was absolutely miserable.” She paused momentarily and smiled to herself as she conjured up the image in her head. “Oh, and Betty, I have to tell you, he’s so smooth! I mean, not a hair anywhere below his head, which, for a teenager, I’m sure added considerably to his shame.…and to have to stand there on display like that….his hairless little penis and undersized testicles out there for me to see <giggle>.…oh, it was really something! I made a point of catching his eye then looking him up and down, and smiling—believe me, I couldn’t help but smile at the delicious scene <giggle>—and somehow his face turned even redder.
"Then I…..you’ll really love this, Betty.…I decided it was a good opportunity to teach the class a few things about the male anatomy. I had him stand on the stepstool while I used my pointer, and we went over every inch of his genitalia. Then, I don’t know what came over me—I think the devil had taken over me <giggle>—but I had him turn around and bend over, putting his little buttonhole on display.”
“Oh, my word, the lad must have been positively mortified!” exclaimed the incredulous and stimulated Miss Richards.
“Yes, it was delightful. <giggle> And then I had a question and answer period, and a couple of my students.…I picked only girls, figuring that would exacerbate his humiliation.…anyway, they asked some very pointed questions about his underdeveloped penis and his.…as one of the girls put it, his ‘total lack of hair.’ <giggle>”
The amused and titillated Betty Richards clapped her hands together. “What a brilliant idea, involving his peers. They can be so wicked. I’m sure he was beside himself.” The grin on her face betrayed her own wicked nature.
“Indeed, Betty, I thought he was going to faint from embarrassment. I don’t think I’ve ever seen anyone’s face so red before.”
Both ladies laughed aloud. Sister Ruth finished recounting the morning’s activities while her fellow teacher listened attentively. At one point Miss Richards rubbed her palms together, both in enthusiasm over the tale and in her eagerness to partake in her own depravity.
The Plan
Before parting, they concocted their strategy for the afternoon. With both of their devious minds working together, it was ensured that Tommy’s debasement would reach a new level.
The plan was to give him his clothes back some time before dance class. This would serve dual purposes: First, it would allow Miss Richards the pleasure of stripping Tommy anew, and second—this is where a mean streak comes into play—Tommy would have a false sense of security, having his clothes back and believing that Miss Richards would never be involved in such debauchery. Then, suddenly he’d have the rug slipped right out from under him—or, more accurately, his clothes stripped right off of him.
The two ladies laughed and nodded approvingly at their plan and their newfound partnership. They exchanged a friendly handshake, and, as Betty departed with her empty duffel bag she called over her shoulder, “See you at two, Ruth. Don’t be late. And don’t forget to bring our little friend!”
The grinning Sister Ruth replied, “Oh, don’t you worry, Betty. I’ll have him in tow, and then he’ll be yours for the picking. Or, I should say, the ‘yours for the
stripping.’ <giggle>”
As the sound of Miss Richards’ laughter echoed through the empty hallway, the shrill of the bell drowned her out. Sister Ruth peered out her window and saw Tommy being put through his paces by the eighth grade girls. She afforded herself yet another smile.