Tommy's Debasement

Stories about boys ending up in compromising situations, preferably naked and embarrassed, as the name suggests.
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Tommy's Debasement, Chapter 14

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Chapter 14: The Dreaded Dance Class

The Gymnasium

“Okay, class, it’s time to go down to the gymnasium for dance class with Miss Richards. I’m going to come down and join you today to see how you’re all progressing,” announced Sister Ruth.

The class formed two lines, the boys in one line and the girls in the other. Tommy was ecstatic to be wearing his own school uniform (or any clothes at all, for that matter!), and felt relieved to be in the boys’ line for the first time that day. He felt just a little bit uneasy, though, at the prospect of Sister Ruth joining them in the gymnasium.

The large room was set up like a typical school gymnasium. There was a full hardwood floor that was usually used for basketball. Most of the bleacher-type seats were rolled up against the wall, except for one section in the middle that was rolled out for the two classes to sit on. There were eight rows, and each row could seat about nine or ten students. There were a total of seventy-three students in the dance class—forty-one girls and thirty-two boys.

Miss Richards had wheeled out a platform for demonstration purposes. The platform had locking wheels and was three feet high and over three hundred square feet around, or large enough for a few people to dance on it comfortably.

Miss Richards stood on the platform as the two classes filed in. Tommy was among the first in the gymnasium. He blushed profusely and looked the other way when he made eye contact with Miss Richards. He promptly found a seat toward the back of the bleacher seats.

Miss Richards always required the seating arrangement to alternate boy and girl to facilitate having a handy dance partner. With more girls than boys in the class, it was necessary for some girls to sit together. As Tommy’s luck (or, more fittingly, lack of it) would have it, his eighth grade tormentors from recess and lunch spotted him and were headed his way. Karen and Linda sat on either side of him, while Nancy sat directly in front of him. Cindy and Sally entered soon thereafter and sat directly behind him.

The eighth graders were surprised, and more than a little disappointed to find Tommy wearing his own uniform.

“Gee, Tammy, what happened to your pretty skirt and blouse? You almost look like a boy in those pants,” teased Karen as she ran her fingers through his hair. “And I notice you’re not wearing your training bra, you little hussy.”

“Leave me alone, it’s over,” answered Tommy while pulling his head away.

Miss Richards interrupted them. “Class, in the first part of today’s lesson we’ll review the steps we’ve learned on ballroom dancing. I need a young man to volunteer as my partner for this demonstration.” As Miss Richards expected, no one volunteered. “Okay, I’ll have to choose someone myself. Let’s see….Tommy, would you come down and join me up here on the platform, please?”

Tommy was abashed that he again would be the center of attention. He heard the girls near him giggle and felt a pinch on his rear end as he stood up. He brushed Karen’s hand away as he weaved his way down the benches and climbed up the side steps of the platform to join the beautiful Miss Richards.


Miss Richards

Betty Richards was waiting with quite a bit more anticipation than she usually had for the weekly dance class. She had felt a stirring within her when she first saw the boy’s clothes, including underwear, cascading by her window, and that feeling had been with her ever since.

She wasn’t sure why she had strong tendencies towards enforced humiliation; all she knew was that it stimulated her like nothing else could. On more than one occasion she had taken advantage of her position of authority and used humiliation on her students as a form of punishment. One of her favorite practices was pinning a pretty pink bow on a blushing boy. She once made a girl get on all fours on her desk and bark like a dog. Yet another time she put bunny ears on a boy and made him hop around the classroom. The inevitable blushing face on the punished child never failed to bring her to a state of delectation.

She had derived considerable pleasure from those experiences, but they were tame compared to what she had in store for the next hour. Forced public nudity had to be at the top of the list of the humiliation experience. And she would take advantage of the dance setting to augment the humiliation of the poor unfortunate. She almost pinched herself to make sure she wasn't dreaming, such was her incredulity of her good fortune.

Her heart beat a little faster when the classes started filing in and she spotted her prey. Miss Richards smiled, for several reasons. She smiled at Tommy’s embarrassment. She smiled at the memory of his naked humiliation in the schoolyard that she witnessed from her window. And she smiled especially at the prospect of what was about to transpire. She was almost giddy with anticipation.

Tommy had grudgingly made his way to the platform. Miss Richards eyed him with relish. “Okay, Tommy, let’s see what you learned from your last lesson. Sister Ruth, could you please start the music?”

A Strauss waltz echoed throughout the gymnasium. Tommy was not much of a dancer, and he took Miss Richard’s left hand instead of the proper right. When she corrected him he moved around clumsily, either stumbling over his own feet or stepping on those of his instructor.

“Stop the music, please. Tommy, it looks like you didn’t learn much of anything last week's lesson. And you’re not moving around very well. Sister Ruth tells me that you’ve been disciplined already today. Do you think you learned a lesson?”

“Yes,” Tommy answered softly, while looking straight down.

“Can you share with us what form of discipline Sister Ruth used on you?” The student was silent. “I asked you a question, Tommy.”

“I-I had to take my clothes off.”

There was considerable tittering coming from the stands. The student before her blushed brightly. Betty Richards smiled to herself.

It’s starting. His first blush.…it only gets better from here.

“Well, that must have been quite embarrassing, but it might not be a bad idea to try that right now. Maybe those clothes are just too confining for you. Perhaps you’d move around a little more freely on the dance floor if we were to take some of them off.”

The boy’s jaw dropped in disbelief at the suggestion.

That’s right, young man.…it’s happening all over again….and I’m loving every second of it .…time to start stripping.

“Let’s at least take your shoes off. That way, if you step on my toes, it won’t hurt as much. Come on, off with them.”

Tommy reluctantly reached down and removed his penny loafers. Sister Ruth was standing next to the podium and held her hands out. Tommy handed them over to the entertained nun. Betty Richards had a gleam in her eye.

He’s at my mercy. This is actually happening!

The music started again, but the absence of Tommy’s shoes did nothing to help his fluidity on the dance floor. He again was stumbling all over Miss Richards.

“Stop the music, please! All right, Tommy, I can see that removing your shoes didn’t do the trick. We’re going to have to go back to basics. Evidently you haven’t been paying attention over the last few weeks.” Miss Richards then turned Tommy towards the captivated audience while she stood directly behind him. “Okay, let’s practice our steps, Tommy.” She had a hand on each of Tommy’s shoulders as she directed him forward a couple of steps, then sideways a couple of steps. “Keep this up, Tommy, slowly, until I tell you to stop. One, two, back, three, four, sideways, one, two...”

That’s it, my little pet….you keep doing my bidding….in the meantime, I’ll go ahead and relieve you of your shirt.…oh, this is so exciting!

While Tommy moved about, Miss Richards reached around him from behind and deftly unbuttoned the top button of his shirt. She continued to talk as she did so.

“One, two, back, that’s it, Tommy.” Betty Richards was very adept on the dance floor, and she was able to move along with Tommy without missing a beat as she continued working on the buttons of the poor lad’s shirt. The seventh graders were once again in a state of merriment, while the eighth graders were wide-eyed, witnessing a forced disrobing for the first time. Karen especially was so excited at the scene that she almost peed her panties.

The last button was undone, and Miss Richards pulled Tommy’s arms behind him and slipped the shirt off his arms before handing it to Sister Ruth, who winked devilishly at Betty Richards during the handoff.

I’m so glad he’s wearing a tee shirt.…it will prolong this wonderful moment, and it means there is one more article of clothing I get to take off....oh, this is such a treat.…I just can’t believe my good fortune!

She continued to guide Tommy through his steps.

Hmm, what shall I tackle next, his pants or his undershirt?….golly, that’s a tough one.…I could strip him to his waist.…certainly losing his pants would be more disconcerting for him, so I could save that for later.…ah, but it would be so delicious to have him dancing around in his underwear.…yes, let’s get those pants off first.

She reached around his waist and found his belt buckle. Tommy immediately grabbed her hands and pulled them away. “Put your hands on your head, Tommy, and keep them there, please,” she said, softly but authoritatively. The young student was no match for Miss Richards—plus the presence of Sister Ruth most certainly reminded him of his subjection. He assumed the position, and continued going through his dance steps under the instructor’s guidance. Miss Richards chuckled softly to herself.

I really hit home with that one.…he actually put his hands on me….oh, he looks so vulnerable now, in that position.…putty in my hands….okay, the belt’s undone.…feels like one button, then his zipper, and then down they’ll go.…take it slowly, Betty, take it slowly….enjoy the moment.

It was all she could do to control her eagerness. She had the belt unbuckled and deliberately went to work on unbuttoning his pants. Successful with that, she proceeded to zip down Tommy’s zipper, and then put her hands back on his shoulders. The beleaguered student paused his dance steps. Miss Richards prodded him along by pulling on his shoulders. “Just keep dancing, honey……that’s it, don’t stop until I say so.”

She watched with stimulation as Tommy’s steps naturally caused the loosened pants to slowly descend down his legs—much to the enjoyment of his classmates, who voiced their approval with exuberant shrieks of excitement. Tommy tried mightily to interfere with the course of events by strategically spreading his legs, but it was to no avail. Inevitably, his pants dropped to a bundle at his ankles, restricting his steps as he continued his performance.

Okay, the button’s undone….here’s his little zipper.…down it goes….ooh, I think I felt him flinch; how delightful.…all right then, I’ll just put my hands back on his shoulders and enjoy the show.…hey, the little devil stopped dancing.…gotta keep him moving….there we go.…oh, yes, they’re starting to fall….oh, look at his cute little white undies…listen to the kids out there, they’re enjoying this, too…look at ‘em, their facial expressions, they can’t believe it.…the poor dear, he must be miserable.…oh, how comical, he’s trying to keep his pants up by holding his knees out.…I don’t think so, my little friend.…yep, there they go, all the way down….look at his slender, pretty legs, how delectable….and Ruth was right, they’re so smooth.…oh, this is just precious!


Tommy

From Tommy’s standpoint, it was, of course, a living nightmare. When Miss Richards called his name to come down and be her dance partner, he slumped his shoulders. He’d had quite enough attention for the day already and was feeling very self-conscious. Then, when she first mentioned something about removing some of his clothes to free up his movement on the dance floor, he thought she was just threatening him so he would perform better. Surely he wouldn’t have to strip off his clothing here in the gymnasium in front of the seventh and eighth grade students! Surely Miss Richards wouldn’t subject him to such debasement.

But then he had to remove his shoes and hand them to Sister Ruth. When Miss Richards removed his shirt and shared a wink and a smile with Sister Ruth, Tommy had a knot in his stomach, and a terrible, sinking feeling came over him.

He was horrified when Miss Richards had her hands on his belt buckle, and he instinctively reached down to pull her hands away. Then he heard the words “Put your hands on your head, Tommy, and keep them there, please.” It was an all too familiar position for him, and everything went downhill from there. In short order, Miss Richards was leading him around the dance floor with his pants around his ankles.

Once again, Tommy was the victim of a teacher’s prurient desires. He could only hope that Miss Richards had a little more compassion in her than the diabolical Sister Ruth.

But as Tommy was being put through his paces, that hope was becoming ever more fleeting.
Last edited by Blondie on Fri Jul 05, 2024 10:27 pm, edited 2 times in total.
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Re: Tommy's Debasement, Chapter 15

Post by Blondie »

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Chapter 15: Depantsed Again

The Shuffle

Tommy continued to go through his steps at the guidance of his teacher, much to the amusement of his captivated audience. His tee shirt was tucked into his white briefs, and his pants were gathered at his ankles. The bundle of his pants restricted his steps, so he was moving rather awkwardly, shuffling around as best he could.

Sister Ruth witnessed from the side of the platform what for her was a most enjoyable scene. She was having a memorable day. She may have been deriving more pleasure as an observer than when she was the one in control. “Gosh, she’s really good,” she thought to herself about Betty Richards.

Miss Richards, meanwhile, was basking in her good fortune. She was in total control of the stripping and humiliation of one of her students. It was fantasy turned reality for her, and she was reveling in the moment.

She took her hands off Tommy’s shoulders and stepped in front of him so she could take in his embarrassment.

“One, two, back, three, four, that’s it Tommy, keep moving.”

My, oh, my, would you just look at him!.…his underwear all exposed, trying to dance with his pants all bundled up at his ankles….so ludicrous, it’s laughable….and his cheeks, they’re positively glowing!.…how delectable.…it’s so tempting just to yank down his undies right now.…patience, Betty, patience, your time will come.…enjoy the moment....well, it IS time to relieve the poor dear of his pants.

“Tommy, I think you’ll be able to move around a lot better if we relieve you of your pants. Why don’t you have a seat up here.” She had pulled a wooden chair up close to the front of the platform, and patted the seat as she spoke. Tommy sat in the seat, all too aware that his humiliation was about to be exacerbated. His audience looked on in fascination. They watched Miss Richards lift Tommy’s feet and prop them against her thighs. She talked to Tommy as she leisurely slid his pants off.

“I really think we’re getting somewhere, Tommy. The last few minutes you looked like you might be catching on.” She started to pull on the bottom of the legs of Tommy’s pants, but he lowered his feet to the ground, inhibiting Miss Richards’ efforts. “Could you please hold your legs straight out, Tommy? I would appreciate it if you wouldn’t make things difficult for me. If you consider your position, someone who is about to be prancing around in front of everybody while stripped to his underwear, I think you’ll agree that it is in your best interests to be more cooperative. You do want to keep your underwear on, don't you?” Tommy's eyes widened as he nodded his head up and down vigorously. "Okay, then," said Miss Richards. "If you don't want to be parading naked for us, I would suggest you be more cooperative with me."

Sister Ruth smiled wider as she marveled at her friend’s humiliation technique.

Tommy turned a deeper shade of red as he held his legs straight out. Miss Richards again took hold of the cuffs of Tommy’s pants and started pulling. She slowly backed up as she pulled the pants further and further off Tommy’s legs. Tommy felt the belt buckle slide across his shins, down his legs, and off his toes as the weight of the belt buckle sped the descent of his pants to the floor of the platform. He watched Miss Richards hand off the pants to the tickled Sister Ruth. Tommy dropped his feet to the floor.

“Did I say you could put your feet down, Tommy?” Tommy quickly and obediently extended his legs straight out. Miss Richards took hold of Tommy’s right foot and slowly peeled down his white sock. She continued her monologue.

“I think you’re going to benefit from this experience, Tommy. You’ll probably remember this day for a long time, and you can use it as a reminder that you need to comport yourself properly.” She had his right sock in her hand and she started pulling off the left one. She was thoroughly enjoying herself as she continued to tease her hapless victim. “Not only that, I think your dancing will improve. A large part of dancing is losing your inhibitions. Think about it, Tommy, in a few moments you’ll be dancing around in your underwear in front of all of your classmates. That should go a long way towards helping you lose your inhibitions.” Miss Richards had both socks in her hands. She bundled the two socks together, rolled them into a ball and tossed them underhanded to the grinning Sister Ruth, who caught them with two outstretched hands and added them to her collection.

Tommy sat with his legs straight out, feeling more naked by the second. All he had left to protect his modesty were his tee shirt and underpants.

Let’s see, I’ll have him sit on this chair…….there we go….oh, the poor wretch, he looks miserable.…it’s so fun to tease him, he blushes so….okay, I’ve got him holding his legs straight out, this’ll be easy….just pull these pants off.…take it slowly, Betty.…God, this is fun!.…there they go, you’ve been depantsed, my helpless little victim.…give these to Ruth.…I’ve never seen her grin like that before….she might be enjoying this more than I.…no, that’s not possible.…oh, he put his feet down, let’s get those back up….yes, I’m not quite done with him yet.…let’s get these socks off….I want him barefoot.…just his underwear, he’ll feel more naked, and it’ll be such a lovely sight.…I’ll slip these off really slowly.…draw out the moment.…the poor boy, he’s just hating this….okay, now the other sock.…look at his smooth, slender legs, how adorable….I can’t wait to have him naked, and squirming around in humiliation….easy, Betty, in due time, in due time.…his moment of truth shall come.…toss these to Ruth.…good catch, Sister!….okay, let’s see him dance around in his undies…this should be charming.


Dancing in His Underwear

“You can put your feet down now, Tommy. I’m anxious to see how much better your dancing will be without all those clothes hindering you. Stand up, please, and let’s see how you do.” Tommy stood up, and Miss Richards lowered the chair from the platform. Tommy stood barefoot with his tee shirt tucked unto his underpants. He had the rapt attention of his classmates. “Please start the music, Sister Ruth,” requested Betty Richards, her newfound soul mate.

Once again, the Strauss waltz played on the stereo. Miss Richards strolled towards Tommy and he took her right hand with his left. His other hand went around her waist, while she placed her left hand around his waist.

And they danced. The previous admonition must have helped, because Tommy was moving around the dance floor a little more adeptly. Not perfectly, but better. He tried his best, because he feared a faux pas would bring on further reprisals—or, more specifically, the loss of more clothing.

The class was thoroughly enjoying the spectacle. A memorable sight it was, a boy clad only in his underwear, dancing about the dance floor with his fully clothed, beautiful teacher.

Look at the blushing boy, dancing with me in his undies….too precious….my, he’s actually moving a little better.…I’m sure he’s hoping I spare him from removing any more of his clothes….does he really think I’m going to stop now?.…sorry, my little lamb….this is a once in a lifetime opportunity for me.…I’ve got you right where I want you….putty in my hands....before I’m through with you, you’ll be a sight for sore eyes, dancing naked for us….now, let’s see what we can do about this undershirt.


And Then There Were Just the Underpants

The music ended, and Miss Richards spoke. “That was better, Tommy, but you’re not moving around quite as freely as I’d like you to. Do you think we need to remove your underwear?” The students giggled and Tommy shook his head demonstratively. “All right, let’s try it again. Music, please.”

Once again, they danced. This time, Miss Richards took Tommy’s hands and put them on her shoulders. She placed her hands on his lower back. After a couple of minutes, Tommy felt an unmistakable tug on the back of his tee shirt. He felt it pull out from within his white briefs. At that point he realized that in a short time he could quite possibly be dancing around in just his underpants. His cheeks burned even more at the prospect.
Miss Richards had both hands on either side of Tommy’s shirttail. She slowly started lifting it up and out of his underpants. The girls in the audience tittered as the exposed skin of Tommy’s back increased before their eyes.

When Miss Richards had the tee shirt rolled up to Tommy’s shoulder blades, she let go. The shirt stayed fixed while she took Tommy’s hands from her shoulders and lifted them high above his head. Tommy was chagrined, but knew better than to put them down. Miss Richards then slowly continued the shirt’s ascent, lifting it up over Tommy’s head, up his arms and over his hands. For one brief moment Tommy held on to the shirt as it passed his fingers, but ultimately he surrendered to the inevitable as he watched his tee shirt gliding through the air into the two outstretched hands of the gleeful Sister Ruth.

Let’s put his hands up here on my shoulders.…good, very good….now I can use both hands to pull up his undershirt.…yes, up and out of those underpants.…I wonder what the poor wretch is thinking now.…the anxiety must be overwhelming!….up it goes.…let me roll it up here at the top of his back, it should stay put….good.…let’s get his arms straight up.…perfect….oh, my, look at his face, he’s positively mortified!.…how delightful.…let’s get this shirt up his arms.…upsy daisy.…lovely, just lovely.…their underarms are so cute when they have no hair yet….off it goes.…ha, he’s holding on to it for dear life, does he really think I’m going to let him keep it? I don’t think so, my soon-to-be-naked little pet….that’s it, there we go, I knew he’d see it my way….send this off to Sister Ruth.…good.…would you look at him now, he’s beside himself….I think I’ll make him dance some more before I get to the best part.…make him think about it for awhile.…oh, I can’t wait!

There was a buzzing from the crowd as Miss Richards motioned to Tommy to continue dancing with her. Again she had him put his hands on her shoulders, and her hands came to rest on his now naked waist.

The windows high on the wall were wide open, and the breeze sifting through the gym caused Tommy to shiver. As for Miss Richards, she was warm as could be, almost feverish in her excitement. “Look your partner in the eyes when you dance with her, Tommy.” Tommy looked up at his teacher’s dancing eyes, and could see the cruel enjoyment she was having at his expense.

At one point, while Tommy’s back was facing away from the audience, she teased him by lowering the back of his underpants below his buttocks. Nobody could see his exposed behind, but Tommy’s surprised and horrified reaction undoubtedly pleased Betty Richards.

I’ve got my hands on his bare skin, I’m sure he’s really enjoying that….I’ll make him look me in the eyes….oh, he looks so humiliated….I just love it.…and there’s a certain amount of fear in his eyes.…he’s wondering, “Is she going to take my underpants off?”….well what do you think, silly boy?.…just not yet, though….I want the moment to build up.…maybe I’ll tease him first….I’ll pull this waist band down below his little bum….down they go.…my, his skin is so smooth.…oh, the look of apprehension on his face.…priceless!.…we’ll keep dancing….I’ll let him feel the open air on his bare fanny for a while.

Then the piece mercifully ended and Miss Richards pulled up Tommy’s underpants and said, “That was much better, Tommy. You can go back to your seat now.”


A Devilish Scheme

Let’s see, how should I go about doing the dirty deed?.…hmm, what would be the most humiliating approach?.…what if I let one of the students do it for me?....one of the girls.…yes, even better than doing it myself….he’ll be absolutely mortified….now who should I….I’ve got it!.…Karen seems to be taking quite a bit of pleasure in all of this.…and she had Tommy squirming earlier when they first came in….yes, Karen will be perfect….I think I’ll send him up there in his underpants, and let her and the girls have some devilish fun with him for a while….oh, this is brilliant!

Tommy was relieved to be finished with his latest humiliation, and even more relieved to be spared from being stripped totally naked. At the same time he felt quite a bit of trepidation at the thought of climbing the benches and sitting between the tormenting girls while stripped to his underpants. He looked longingly towards his clothes and at Sister Ruth, but she had a look on her face that seemed to say, “I don’t think so.”
He headed towards the benches, with one arm over his chest and the other arm covering the small protrusion in his briefs. Miss Richards was relentless.

“Tommy, please keep your hands at your sides. There is no place for modesty in my dance class. Like I said, you need to lose your inhibitions to become a successful dancer.”

The profusely blushing Tommy dropped his hands to his sides as he stepped down the stairs of the platform and started climbing the benches toward his seat. The giggling and tittering continued unabated. He glanced up to his saved seat between the grinning Karen and Linda. He shuddered at the thought of sitting there, almost naked, among a group of girls who were salivating at the chance to further his humiliation.
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Re: Tommy's Debasement

Post by TeenFan »

With just a little work with Mrs. Richards, Tommy should be able to pull off dance performances like this one.

https://v.qq.com/x/page/c3128kkc0ka.html

Very little clothing and looks more like a girl than a boy in the first performance. In the second one, one of his classmates took scissors to his
costume.

This is an old video of Russian contortionist Alexey Goloborodko in 2007. He is known as the world's most flexible human.
Performs with Cirque du Solei now.
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Re: Tommy's Debasement

Post by Blondie »

Ha! No amount of yoga (or training from Miss Richards) would enable Tommy to bend like that. Though his classmates would love to see him do that naked.
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Tommy's Debasement, Chapter 16

Post by Blondie »

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Chapter 16: At the Mercy of a Gaggle of Girls

The Pink Bow

As Tommy traversed the gymnasium stands he spotted a little opening next to one of his friends. Trying to avoid sitting in his original seat with the girls, he made a motion to his friend to move over. Showing compassion, he did so, and Tommy sat next to him. Miss Richards would have none of it.

“Tommy, what do you think you’re doing? I asked you to go back to your seat.”

“Sorry, Miss Richards, I didn’t think it really mattered where I sat,” answered Tommy.

“You didn’t think it mattered? Oh, I’ll show you how much it matters. Please come back down here right this instant.”

The chagrined Tommy timidly made his way back down toward Miss Richards. He climbed the steps up to the platform. He feared he might lose his underpants, and his anxiety level was extreme.

Then he noticed Miss Richards held in her hand a large pink bow. Tommy had heard about Miss Richards’ occasional employment of the bow and was grateful it had never appeared in her dance class. But there it was, looming ominously in Miss Richards’ hand. Tommy pictured himself wearing the bow while clad in his underpants (or naked!), which only added to his apprehension.

All was quiet in the gymnasium as everyone waited to hear Miss Richards’ chastisement. They would not be disappointed. “Tommy, you’ve disobeyed me. I asked you to go back to your seat. You know I prefer the seating arrangement to alternate boy and girl, yet you sat next to a boy. Do you think you’re a girl, Tommy?”

“No,” Tommy answered softly while staring down at his bare feet.

“Well, you sat next to a boy, so I think you secretly like the idea of being a girl. It’s your lucky day, Tommy, because I’m going to accommodate and let you wear this pretty girly bow on your head for the rest of the class.”

He again heard the giggles from the audience as Miss Richards deliberately fastened the bow securely to the top of Tommy’s hair. The wide bow extended the full width of his head, rendering Tommy to appear almost cartoonish.

Miss Richards stepped back and admired her creation with a smile on her face, while Tommy stood miserably, wallowing in his new disgrace.

“I do declare, you make a very pretty girl, Tommy. The bow looks quite lovely on you, and it compliments your blushing cheeks rather nicely. I must say, you’re looking more feminine by the second. All you’re missing now is a pretty pair of panties, and maybe a training bra. If I find it necessary, I’ll bet we could prevail on Sister Ruth to round them up for us." Miss Richards took notice of Tommy's wide-eyed expression and smiled to herself. "Now go back to your original seat, and behave yourself,” she said as she playfully slapped his behind.

Oh, he thinks he’s not going to sit with the girls, does he? We’ll just see about that.…heh, heh, now I get to employ one of my favorite punishments….I just happen to have the bow in my bag….I didn’t think I’d need it, figuring that stripping the boy naked might be quite enough….but this might be a real nice touch….a little forced feminization in conjunction with imposed nudity.…does it get any better than this?.…oh, here he comes….look at the poor dear, he looks like a frightened little kitten.…I’ll bet he thinks I’m going to strip him naked.…oh, just you wait….your time will come, my precious little friend.…but first we’re going to have a little fun with you….let’s pretty you up a bit.…clip this bow on up here….excellent, he’s got just enough hair so it will stay put.…I hate it when I do this to the short-hairs, it tends to dangle.…yes, this looks divine….oh, my, look at him, he’s blushing more than ever….how delicious….the bow does the trick every time….and the look on his face when I threatened to send for the panties and training bra….priceless….I wish there was time to sissify him.…I would do just that…what a delightful image that makes.…ah, but we have other fun and games planned for you, my little lamb….I’m about to throw you to the wolves….okay, I’ll give you a slap on your little butt and send you on your merry way.…oh, how delectable....it just keeps getting better!


The Gaggle of Girls

Tommy, now blushing crimson, had to make the tormenting trek back to his seat. The bow added considerably to his shameful plight. It only weighed a couple of ounces, but it felt to him like he was supporting the weight of a brick.

Averting eye contact, he climbed the bleachers as quickly as possible. When he neared his destination, he looked up and cringed at the expectant, grinning girls who awaited him. To his dismay, Sally and Cindy seemed even more excited than ever. He wondered what mischief they were up to. He looked at Karen, and wondered how somebody could be so pretty, yet so mean.

Then, to exacerbate his considerable trepidation, Karen giggled, and then laughed out loud at something Sally had just whispered in her ear. With a strong sense of dread, he reached his original seat. Linda grabbed the waistband of his last remaining garment and pulled Tommy onto the bench between herself and Karen. Immediately Karen turned toward him, and brushed his ear with her lips as she spoke to him.

"Welcome back, sweetie. Remember, you still owe me a look at your cute little wee-wee,” she chortled as she caressed his bare chest.

Tommy brushed her hand away and Miss Richards called out, “Tommy, I don’t want to have to tell you again to keep your hands by your sides. If I have to, I’ll tie them behind your back, believe me I will.”

Oh, this might turn out even better than I thought. He’s barely sat down, and Karen already has him hot and bothered.

Tommy lowered his hands to his sides as Miss Richards began a review of the steps involved in folk dancing. The distracted students continually turned to gape at the very unusual sight of a boy with a pink bow in his hair, clad only in his underpants, seated among a group of fully clothed girls.

Tommy, of course, was absolutely mortified, and totally helpless to fend off whatever torments the girls would deal him. Karen, who was beside herself in her cruel enjoyment, continued to tease her victim. “That’s a really cute bow, Tammy. Just adorable,” she said as she pretended to straighten it on his head. “Yes, you look much more like Tammy than you did when you first came in here.” She ran her hand back and forth across the top of Tommy’s left thigh, much like she did during recess, but with more exposure she had a larger area to cover. “And you’ve got such pretty legs, Tammy. Linda, feel Tammy’s legs. They’re so nice and smooth.”

Linda did so, cooing “Ooh, you’re right, Karen. Tammy must have shaved them this morning. Nancy, feel Tammy’s legs, they’re just velvety smooth.”

Tommy now had two girls running their hands across the tops of his thighs, taunting him all the while. Nancy, sitting in front of him, had turned around and began stroking his calves. Cindy and his sister Sally were giggling freely directly behind him.

Tommy then felt the elastic band on the back of his underpants being pulled back, then released like a slingshot as it sprang back, making a snapping sound and slightly stinging his lower back. He looked back just in time to see Sally’s hand retreat as Sally and Cindy giggled merrily. Karen and Linda joined in the fun, pulling the band from the sides and letting it snap back. Karen then pulled the band out from the front, and started to lean over to look inside. Tommy fidgeted anxiously and managed to ward off the unseemly advance without moving his arms from his sides.

“What’s the matter, Tammy, don’t you want to let me get a peek at your little pee-pee? My, aren’t you the bashful one.” Again Karen tried to look down the front of Tommy’s underpants, and again he managed to fend her off.

It was about that time that there was an occurrence that marked the beginning of the end of Tommy in his clothed state, such as it was. Sally, knowing how ticklish her brother is, used both of her hands to tickle Tommy’s sides with her fingers. Tommy almost jumped out of his seat, as he couldn’t keep from slapping his sister’s hands away, an action that did not go unnoticed by the highly entertained Betty Richards.

“Tommy!” warned Miss Richards, “I’ve asked you to keep your hands at your sides, but you seem to be having trouble obeying me. Now I want you to clasp your hands behind your head and have your elbows pointing straight out to the sides. And sit up straight. This is your last chance. If you can’t restrain yourself and maintain that position, then I’m going to have to relieve you of your underpants. Maybe if I make you sit there stark naked then you’ll behave yourself. Now do as I say, and this is your last warning.”

Amid the animated giggling from the students, Tommy, turning yet redder, complied with his teacher’s instructions. The tittering from his classmates continued, as Tommy sat perfectly erect with his hands clasped behind the pink bow on his head and his elbows pointing straight out. He was feeling more and more embarrassed by the second, and quite fearful of the prospect of losing his underpants.

Oh, would you look at him now….a sight for sore eyes…squirming about, totally helpless….his hairless underarms on display….I just LOVE it!.…the girls are getting ready to pounce.…you can feel it.…he’ll be putty in their hands.

Karen wasted no time in taking advantage of the situation. With both hands, she pulled the back of Tommy’s underpants down and tucked them as far as she could under Tommy’s buttocks.

Tommy, wide-eyed and open-mouthed, lifted and gyrated his hips in an effort to restore his modesty (of what little remained!), much to the amusement of the giggling girls. But his underpants remained steadfast, wadded underneath him.

Karen put her lips to his ear. “You heard Miss Richards, Tammy,” she teased. “You’d better sit still, or they’re coming completely off. Then you'll be naked. Completely naked in front of all of us. And I’ll finally get to see your little wee-wee.” She leaned back and looked down at Tommy’s seat. “Your crack is showing, you naughty, naughty boy.”

The giggling turned to outright laughter. Tommy, beside himself, looked to Miss Richards, hoping she would put a stop to the sordid proceedings before they got completely out of hand. Instead, much to his consternation, she was grinning and giving Karen the “okay” sign by connecting her thumb and middle finger, forming a circle. Tommy looked at Karen, who grinned at their teacher while returning the sign.

“Oh, God,” muttered Tommy desolately to himself.

Oh, that Karen is such a little devil.…it’s just a matter of time now, my little pet.…the girls aren’t about to let you sit still....before you know it, you’ll be surrendering your underpants to them at my command….that is, if they can wait that long.


The Feathers

Then, unbelievably, somebody (nobody but the culprit knew where they originated) produced two large, red feathers. Starting from the front left of the stands, the feathers gradually made their way toward Tommy, passing from hand to hand. Tommy heard the giggling and slight commotion coming from his left and observed with uneasiness that the feathers were heading in his direction. When they were passed to Karen, he winced as he braced himself for the inevitable.

But Karen surprisingly relinquished the feathers to his delighted sister while saying, “I hope you’re not ticklish, Tammy.”

Sally had seen the feathers working their way up the stands, and wanted in the worst way to get her hands on them. When they were passed to Karen, it appeared to her that her hopes would be dashed. But Karen had assessed the situation, and took into account that Tommy’s anxiety would be increased if he were tickled from behind, in which case he would not know when nor where the feathers would be applied. The fact that his sister would be wielding one of the feathers would undoubtedly add to Tommy’s distress.

When Karen passed the feathers to her, they shared a devious grin and a giggle. Sally handed a feather to Cindy, and the two girls grinned cunningly to each other. They strategically let a couple of minutes go by before Sally launched the attack.

He first felt a little tickle on the cleft at the top of his exposed buttocks. The startled Tommy flinched and retracted his hips, sitting up rigidly, much to the merriment of all the onlookers. Sally continued twirling the feather in a circular motion just above the back of Tommy’s underpants. Tommy closed his eyes as he tried to remain still. Then he felt another tickling sensation low on his side, before it slowly crept upward, as Cindy moved the tip of her feather in a circular motion, upward from the right side of Tommy’s waist at an excruciatingly slow pace.

Tommy arched his back as Sally’s feather started rising up his torso. He gritted his teeth, still sitting up straight with his elbows pointing straight out, as he struggled mightily to maintain his position.

Sally and Cindy were having a glorious time, as they could sense Tommy weakening by the second. His movements were quite subtle, but the girls knew their teasing with the feather was having the desired effect. Sally especially knew that it would be a matter of moments before Tommy would lose the battle. While they were growing up, more than once she had pinned Tommy down and tickled him, and invariably it ended with her tickling his armpits and him losing control, being forced to yell “Uncle!”

Soon she would go in for the kill. She licked her smiling lips in anticipation as her feather crept its way up toward her goal. She could see that Cindy had the same objective, and again they exchanged mischievous glances. Each of the girls had leaned forward to have the best angle to tease their prey.

When Tommy felt the two feathers begin circling each of his nipples, he was on the verge of breaking. He squirmed and fidgeted under their unyielding torment. The girls squealed with giddiness at the scene they were creating. It was a most amusing sight for all, with, of course, the exception of the squirming, near-naked lad.

In a matter of moments they would go for the jugular.


Girls Win

It was about the time that Karen had grabbed hold of the front band of Tommy’s underpants that Sally and Cindy looked at each other, nodded, and mouthed the word, “Now!” Simultaneously the two feathers reached their target, and Sally and Cindy, grinning wickedly, feverishly stroked the feathers back and forth across Tommy’s vulnerable armpits.

As expected, Tommy was no match for the relentless, aggressive line of attack. He reached down and pulled Karen’s hand away from his underpants. He elbowed away the two hands controlling the feathers. He pulled up the back of his underpants.

He knew he was in serious trouble.

It’s time, my helpless little victim.…you held up longer than I expected….one does fight harder when desperate.…but it’s all for naught, because you’ll soon be bare nekkid….and I’m sure Karen will give you a most exquisite stripping.…oh, this is so exciting!

Miss Richards was in the midst of explaining a dance step when she stopped in mid-sentence. It was the moment she had been waiting for. “Tommy, would you stand up, please?” Tommy had a strong feeling of foreboding as he reluctantly stood up. “Tommy, what did I tell you would happen if you interrupted this class again?” Tommy mumbled something inaudible. “Speak up, Tommy. What punishment did I promise you if you misbehaved again?”

“You said I’d have to…to take off my underpants.” There was giggling all around.

“That’s right, Tommy. You’ve given me no choice but to take your punishment to the next level. It’s time to get you completely………..and totally…………..nude.” She emphasized the word “nude” with a longer than normal “ooh” sound, with pursed lips and gleaming eyes. Grinning wickedly, Miss Richards paused to take pleasure in her blushing, most apprehensive victim. “Only I thought it might be a little more interesting—and certainly more shameful for you—if I let one of your female admirers have the honor of pulling down your underpants—and removing them, of course.” The hapless lad cringed while the rest of Tommy’s giggling classmates, in eager anticipation, postured themselves for the best possible view of what promised to be a very entertaining spectacle.

“Class, do I have any volunteers?” Not surprisingly several hands shot up in the air, most of them from the group of girls in Tommy’s vicinity. “My, my,” teased Miss Richards. “You certainly have a lot of admirers, Tommy, and they all seem quite intent on relieving you of your underpants.” She paused for effect. “Let’s see.…Karen, you seem quite enthused, and I’ll bet you’d be quite adept at carrying out Tommy’s punishment. Would you like to divest Tommy of his underpants?”

Karen could not believe her stroke of good fortune. “Yes! Oh, thank you, Miss Richards! I would love to take off Tammy’s-er-Tommy’s underpants for him. That way, he'll be naked." She then looked straight at Tommy's midsection while saying, "And I’ll get a close-up view of his little wee-wee,” she grinned. The laughter from the students was effusive.

“Thank you, Karen. Tommy, would you please turn and face Karen?”

Oh my, I don’t think I’ve ever felt so.…so stimulated!….I think I’ve made the perfect choice….he’ll be so much more shamed to have young Karen do the.…the unveiling.…I don’t know how he’ll be able to stand it!….I wonder how she’ll go about it?.…will she do a slow, excruciating take-down of his undies, or will she just yank them down for the shock effect?.…either way, the humiliation should be out of this world….then, when she’s done with him.…I’ll give her a few minutes to make the most of his naked shame.…when she’s done I’ll have him come down here and prance around on the dance floor.…to force him to put on a show by dancing naked for us.…that might be the ultimate humiliation.…oh, just the image of that in my head.…his little penis bobbing about while I make him shake his hips.…he’ll have an all-time blush going.…oh, Betty.…I think I’ve died and gone to heaven!


Karen Takes Charge

Tommy slowly, grudgingly turned toward his nemesis. He was at the depths of his humiliation, and his anxiety was turning to outright fear. He was about to be stripped naked in front all of the seventh and eighth grade students. On top of that, a girl in the eighth grade class who was thrilled with the prospect would be doing the dirty deed. Plus, his sister and Cindy were barely an arm’s length away, relishing every moment.

He looked under the stands, wishing he could just slide down and disappear.

The titillated Karen was certainly going to make the most of her extraordinary opportunity. “Tammy, would you please come over here and stand in front of me?”

Tommy stayed put. Karen was not a figure of authority, and he did not feel compelled to obey her. To no one's surprise, Miss Richards intervened.

“Tommy, I’d like you to follow whatever instructions Karen gives you. I have the utmost confidence in her ability to discipline you properly, and I want you to consider anything she says to be coming straight from me. Is that clear?” Tommy nodded disconsolately. “Good. Now Karen, I’m giving you complete control. Be aware that I am a firm believer in shame and humiliation as an effective means of punishment. Take your time, and feel free to use any measures you wish if you feel it may enhance Tommy’s humiliation.”

“You can count on me,” replied the grinning Karen.

The beleaguered Tommy had no doubts about the veracity of the young fiend's words.

“Come here, Tammy,” said the newly charged Karen as she took Tommy’s wrist and pulled him in front of her. Tommy stood between Karen’s knees with his hands by his sides. His eyes were at the same level as his adversary. Cindy eagerly plopped into the seat to Karen’s left, while Sally leaned in directly over Karen’s shoulder to attain a better view. Linda slid into the space vacated by Tommy.

Everyone in the gymnasium gave the twosome their undivided attention. Many students were standing to get an unobstructed view. The gymnasium was completely silent, as no one wanted to miss any of the exchange between the tormentor and her victim.

Karen would not disappoint them. “Tammy, I’d like you to look me in the eyes as I speak to you.” Tommy nervously raised his eyes to meet hers, and he could see the expression of absolute merriment in her face. She took Tommy’s hands in each of hers. “I’d like you to ask me very politely if I would please take off your underpanties. And please use my name when you address me.”

Guffaws and giggles rang throughout the gymnasium. Miss Richards and Sister Ruth looked at each other and grinned in admiration. Karen was doing them proud.

Tommy hesitated; he wasn’t quite ready to partake in his new debasement.

“Don’t keep me waiting, Tammy," persisted Karen. "I’m already becoming impatient with you. Now ask me, and ask me very nicely. And everybody better be able to hear you.”

Tommy relented, much to his shame. “Karen, would you p-please take off…my underpants?”

“That’s not what I said, Tammy,” scolded Karen. "I asked you to say underpanties. Just for that, you can call them panties.” She paused, allowing the ignominious command to sink in. “Now that I think about it, with that pretty pink bow on your head, your silky-smooth legs, and your hairless underarms, ‘panties’ is more appropriate anyway. Now let’s try it again. What would you like me to do, Tammy?”

The students giggled, and then quieted. Tommy took a deep breath. He looked in Karen’s eyes. “Karen, would you please take off…take off…my p-panties?”

Karen grinned from ear to ear. “Why, yes, Tammy, I would love to take off your little panties for you. You know I’ve been waiting all day to see your little wee-wee that everyone is so amused about. But I think you should get permission from Cindy first.” Karen let go of Tommy’s hands and gently guided him towards Cindy by pushing on his hip. “Now stand in front of Cindy, look her in the eyes and ask her very nicely if I can take off your panties for you. And make sure you call her by her name.”


Teased and Tormented by Cindy

There was no turning back for Tommy now. He stood in front of the young girl with whom he was infatuated. He looked up woefully at her twinkling eyes. “Cindy, would it be okay…”

“Come sit on my lap, Tommy,” interrupted Cindy. She put her knees together and helped the tormented Tommy onto her lap, facing her. “That’s a good boy.” She reached down and took Tommy’s ankles, pulling him toward her. Sally, ever the helpful one, took Tommy’s ankles from Cindy’s grasp and pulled as far as she could. Tommy was forced to grab Cindy’s shoulders to keep from falling backward. His groin was now up against Cindy’s midsection.

Sally held onto Tommy’s ankles while the giggling Cindy rested her hands at the very tops of Tommy’s thighs. To Tommy’s chagrin, he felt her fingers delve just inside the leg opening of his underpants. Tommy, in quite an awkward position, maintained his balance by reaching around Cindy and holding on to her back, near her clavicles. Cindy, basking in her newfound position of power, grinned at her submissive subject. She opened with a bombshell. “I hear you have a crush on me, Tommy,” she said. Tommy’s eyes widened, and he blushed a deeper shade of red. He glanced furtively at his grinning sister, and rued the day he confided in her in a moment of weakness. “Yes, Sally told me,” continued Cindy. “Sally tells me everything. She told me how shy you are about your body….how you won’t even go swimming because you don’t want anybody to see you in a bathing suit. Is that true, Tommy? Are you bashful about showing your body to us?” Tommy didn’t respond. “Answer me, Tommy. Are you shy about your body?”

“No…I mean…I don’t know…maybe…please, I…”

“I understand if you are, Tommy. I mean, you’re thirteen years old, you’ve got these pretty little legs…” Cindy took her right hand and ran her fingers up and down Tommy’s leg before returning her hand to the top of his thigh. This time she ran her hand all the way up Tommy’s thigh and under the leg opening of his underpants. Her fingers protruded all the way through the waistband and came to rest at Tommy's tummy. The beleaguered lad flinched, and Cindy followed suit with her other hand. She inched her hands toward each other, resting them ever so close to Tommy’s genitals. She smiled at Tommy’s look of anxiety before continuing with her banter.

“You haven’t grown any hair at all on your body. I mean, your skin is silky smooth, like a young girl’s.” Cindy strummed her fingers playfully along Tommy’s midsection. “And I’ve seen your tiny little pee-pee.” As she said “tiny little pee-pee” she took hold of Tommy’s.…well, his tiny little pee-pee. She jiggled it back and forth with her thumb and her index finger. Tommy nearly jumped out of his underpants at the intrusion. “So it's perfectly.…gosh, it’s so tiny I could barely find it!……so it’s perfectly understandable that you’d be uncomfortable about anyone seeing your body.” She looked Tommy up and down, while grinning freely. “Now here you are, stripped to your underpants in front of all these people, sitting on the lap and at the mercy of a girl you probably want to make a good impression on. Can you appreciate the irony of that, Tommy?”

Tommy couldn’t respond. Cindy had moved her other hand over and now was gently cupping Tommy’s testicles. He fidgeted his hips nervously, unsuccessfully trying to extricate himself from her grasp. He fixated his gaze to a dark opening in the bleachers below. “Look at me, Tommy.” When he did, Cindy smiled at him and said, “Now, what was it you wanted to ask me?”

Tommy took a deep breath. After a long pause while he tried to gather himself, he blurted out the requisite question. “C-Cindy, would it be okay if Karen took off my und…my p-panties?”

Cindy feigned surprise. “What, you want Karen to strip you completely naked? Tommy, I’m shocked! You’re so self-conscious about your body that you won’t even wear a bathing suit in public, and now you want to put this little wee-wee of yours (she jiggles it again) on display in front of all these people? Well okay, Tommy, if that’s what you want, you have my permission. Let Karen take off your little undies, and let everyone laugh while they watch your hairless little pee-pee bobbing around. But first you’d better see if it’s okay with Sally.” Cindy, grinning derisively, planted a big, wet kiss on Tommy’s lips before placing her hands under his armpits and helping him off her lap.

The wretched Tommy stood transfixed before collecting himself. He looked up at his beaming sister and said, “Sally, is it…is it…is it okay for Karen to take off my p-panties?”

Sally, who was having fits of convulsive laughter throughout Cindy’s taunting, could barely speak, such was her state of hilarity. "Well, sure, my dear little brother, it’s okay with me, if that’s what you really want. But maybe you should check with Linda first.”

Tommy was forced to continue his humiliating charade by asking Linda, then Nancy the same question.

It seemed that they were all in full agreement that Karen should take off Tommy’s underpants.
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Re: Tommy's Debasement

Post by lovaboitoy »

Amazing story love it!
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Tommy's Debasement, Chapter 17

Post by Blondie »

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Chapter 17: The Naughty Niece

Facing Karen

Tommy felt a tug on his elbow, and within moments found himself face-to-face once again with his nemesis Karen, who had been eagerly anticipating his return. “Well, here we are, Tammy,” said the grinning Karen. “Finally. It’s show time. Can you believe it, Tammy?” she asked gleefully. “It’s the moment of truth. I finally get to see your little wee-wee, in all its little glory.”

Tommy’s breaths became shorter and faster, and his trepidation was mounting. All eyes were on the couple as Karen had her hands on Tommy’s bare waist. Tommy could feel her fingertips of both hands protruding beneath the waistband of his underpants. Her face was flush with excitement as she looked Tommy in the eye.

“It’s the moment we’ve been waiting for, Tammy darling. Are you as excited as I am?” Tommy didn’t answer. “Isn’t it a thrill to know that everybody in here is watching just the two of us? And in just a few moments, all eyes will be entirely on you. And you’ll be naked! Don’t you feel special, Tammy?” She started to lower Tommy’s last piece of protective clothing, and Tommy instinctively grabbed her hands. “Uh, uh, uh….Tammy, you’re not being very cooperative. Please put your hands above your head.” Tommy obeyed, clasping his hands behind his head. “That’s my good little boy.”
Karen removed her fingers from inside the waistband and took hold of Tommy’s underpants from the bottom, one hand on each side. She slowly, teasingly, started pulling down.


Tommy Makes a Run For It

Tommy, meanwhile, was nearing a breaking point. Bowing to authority, bullying and intimidation, Tommy had so far submitted to the depraved whims of Sister Ruth, Miss Richards and the seventh and eighth grade girls. But as he felt his underpants slowly being lowered, his anxiety increased significantly. As he imagined the humiliation of standing naked before the devilish Karen and the entire seventh and eighth grade students, Tommy could endure no more. He had to make a run for it.

His first move was to lower his arms and slap Karen’s hands away from his underpants. So far, so good. As he pulled his underpants back up to his waist he quickly surveyed an escape route and made a beeline through the stands toward the exit.

The startled Karen had recovered from her victim’s surprisingly bold move and began pursuing her scantily-clad prey. Sally, Cindy, Nancy and Linda were close behind in pursuit. Tommy, transfixed on his objective, could barely hear the boisterous uproar generated by the highly entertained (albeit somewhat disappointed) students.

He had maneuvered his way through the stands to the gymnasium floor, and though he was being closely pursued by the equally determined girls, he saw a clear path to the exit. But to his consternation, in his haste he tripped slightly on a speaker wire, slowing him down just enough to allow the persistent Karen to reach out and grab onto the back band of his underpants. A comical scene ensued—though for Tommy it was quite unnerving—as Tommy reached back in an unsuccessful attempt to dislodge Karen’s tenacious grip. Karen, not one to let an opportunity go by, used both hands to yank Tommy’s underpants down to his ankles, much to the unbridled glee of the onlookers.

"No!" squealed the lad. Tommy, now frantic, stopped in his tracks for fear of stepping completely out of his underpants. He could only use one hand to try to pull them back up, because he needed his other arm and hand to feverishly hold back his antagonist’s head, as Karen, in her dogged determination to finally see Tommy’s little penis, tried mightily to peek around his back side.

Meanwhile, the other four girls, who had momentarily stopped to take in what for them was a most entertaining scene, collectively decided to join in the fray. Tommy had just managed to pull his underpants up to his knees when Sally intervened and jerked his hand away while Cindy worked on tugging them back down. Tommy, adding to the hilarity, began hopping on one foot while holding his other leg straight out in a desperate attempt to keep his underpants from coming down. Nancy and Linda became very interested spectators, standing in front of Tommy, both of them covering their grinning, wide open mouths with one hand and pointing at Tommy’s bobbing little penis with their other.

Tommy still managed to keep Karen at bay, but it seemed certain that it would be a matter of seconds before he would succumb to the onslaught.

Tommy’s salvation, though temporary, came from a very unlikely source.


A Reprieve From Miss Richards

Oh my, Karen is a natural at this.…taking her time, taunting him instead of going straight for the kill….just a wonderful buildup…."All eyes will be entirely on you….and you’ll be naked!”.…that was a nice touch.…I love it!.…the poor boy must be ready to faint from embarrassment.…and fright!.…imagine being in his shoes right now.…or more appropriately, his underpants.…no, I really can’t imagine.…I think I’d die on the spot.…ah, she’s had him put his hands on his head….I think we’re getting close.…here we go….oh, yes, she’s starting to draw them down, ever so teasingly.…oh, this is so much fun!.…there, I can see the top of the crack of his little fanny.…oh, it’ll be so cute to see him squirming around naked.…and the look on Karen’s face, what a delight…she is absolutely thriving in the moment.…if only I had that opportunity when I was her age.…lucky girl, she’ll be thanking me until her dying days.…oh! there he goes! I had a hunch he might try to make an escape.…can you blame him?.…ah, this is amusing.…look at him dashing through the stands in his little underpants.…can they catch him?.…Karen looks positively pissed, the little terror.…oh, he tripped on the cord….here she comes….yep, she’s got him by the waistband….he’s in trouble.…oh! down they go!….hee hee!.…how exciting, he’s almost naked….and the bow in his hair, it’s still firmly in place….oh, this is a riot!.…he won’t let her see the goods….she’s just dying to see his little penis, isn’t she?.…there's really not much there.….…oh, look at Linda and Nancy, pointing and laughing.…God, I wish I had this on video.…I’d watch it every time I needed a laugh….or some self-pleasuring.…oh, here come the reinforcements.…he’s in deep doo-doo now.…he’s hanging on for dear life.…the poor boy has no chance against these fiends.…he’ll be buck naked in a matter of seconds.…but I think I’ll put a stop to this.…as enjoyable as this is, I’ll stick to my original plan.…that way, we can prolong the suspense.…it’ll make the stripping scene that much sweeter.

“Let him go!” shouted the grinning Miss Richards over the laughter.

The girls, very much caught up in their endeavor, either didn’t hear or pretended not to hear their teacher’s command. Cindy had worked Tommy’s underpants off the leg he was hopping on and was hell-bent on finishing the task, which at that point seemed a foregone conclusion.

“I SAID, LET HIM GO!” screamed Miss Richards, with considerably more intensity.

Much to the disenchantment of Karen and her cohorts, the girls reluctantly obeyed their teacher and watched dejectedly as Tommy hurriedly stepped into his underpants, hauled them up while he sprinted the remaining twenty yards to the exit, pushed the door open and disappeared from sight.
Karen was visibly upset. She slumped her shoulders and was on the verge of tears, such was her state of anticipation and stimulation of being so close, then being thwarted in her endeavor to unveil and humiliate the seventh grade student.


Introducing Carlene

As the downcast girls trudged back to their seats, their teacher’s mood was quite the opposite. Realizing the strong potential of her victim possibly attempting escape—all things considered, she would have been surprised had he not—Miss Richards had a contingency plan. It so happened that her fifteen-year-old niece would be available (and more than willing, as the perceptive aunt had expected) to lend a hand, should the need arise. Carlene, a sophomore and star volleyball player of the nearby high school, would be using the gym later that afternoon for practice. She and her teammates were warming up outside, waiting for the dance class to finish.

It was not an act of desperation on Betty Richards’ part to involve her niece in the humiliation of a thirteen-year-old student. In fact, it was a calculated gamble on her part. As it happened, there was a conversation she had with Carlene a few weeks before that solidified in her mind that her niece shared in her proclivity towards humiliation.

The two of them were sitting on a park bench that day, savoring the tranquility of a pleasant afternoon while they scooped their ice cream sundaes from plastic containers. Their serenity was rudely interrupted by a nearby ten-year-old boy, who screamed bloody murder when his mother told him it was time to go home. She was unsuccessful in her attempts to quiet him down.

“If I were his mother,” offered Miss Richards, “I would take the boy over my knee right here in public and give him a bare-bottomed spanking.” She glanced at her niece and smiled as her face lit up.

“And you shouldn’t stop there, Aunt Betty,” she responded. “You need to really teach the little monster a lesson he wouldn’t soon forget.” Carlene stared at the young lad while her imagination took over.

“Please, go on,” prodded a surprised and very interested Betty Richards.

They had both left their plastic spoons impaled in their ice creams, as they were now consumed with their stimulating conversation.

“Well, there are several things you could do. And they all would be quite effective.”

Again there was a pause. Betty wondered if her niece was toying with her. “Well, are you going to tell me what you have in mind for this impertinent lad, or do I have to pry it out of you?”

Carlene laughed. “Sorry, Aunt Betty. I had so many thoughts running through my head that I didn’t know where to start. I do like the idea of forcing him over my knee and pulling down his pants—and his underpants—right here in broad daylight. The more spectators the better. But I would take it a step further. While I had him over my knee I would pull off his shoes and socks and then completely strip off his trousers. His underpants could hang at his ankles. Oh, and I would definitely pull his shirt off, just to make sure the shirttail doesn’t get in my way. Plus, that way he’d be almost nude, which would give him something to think about while I’m giving him his spanking and his underpants are precariously dangling at his feet, or maybe even his toes. In fact, I think I’d make sure that they came off one foot.” Carlene paused to catch her breath. Her aunt stared at her wide-eyed, and was more than a little titillated. She listened intently as Carlene continued. “He’ll be wondering, ‘Will I get my trousers back? Will my underpants fall completely off and I'll be naked?’ I mean, he’ll be beside himself with the trepidation and humiliation of it all! And while I’m spanking him I’ll be scolding him, and teasing him. ‘This is what happens to naughty little boys,’ I’d say. ‘How shamed you must feel. Everyone is looking at you, and they're staring at your naked little bottom. And I do say, it’s turning quite a pretty shade of pink!’

"And then when I’m finished spanking him, I’ll stand him up, facing me so I can scold him some more. He’ll immediately reach for his underpants, but I wouldn’t let him pull them up right away. I’d draw out his scolding for a spell while he stands there with his underpants at his feet. I’m sure he’d have his hands covering his little penis. I’d say, ‘Have you learned your lesson, young man?’ Of course he would be all red in the face and nod his head—he might be crying like a baby and be unable to speak—and I’d make him tell me out loud that he’s learned his lesson. He will, otherwise he can stand there like that until the sun goes down.

"When he eventually does I’ll say, ‘Good. You can pull up your underpants now, but you’re not getting the rest of your clothes back until we get home. You can think about how you’ve been behaving while you walk home with me in your underpants. And if you give me any more grief, those are coming off too, and you’ll walk home stark naked.’ I’d make him take my hand and we’d walk home at a nice, leisurely pace. Can’t you just picture it, Aunt Betty? Oh, how I’d love to be that brat’s mother for a day….”

“My, oh, my!” exclaimed the incredulous Betty Richards, as she looked at her niece in astonishment. “Where in the world did you get such a sadistic streak? That boy would have the humiliation of a lifetime. Don’t get me wrong, I love it!”

Both of them laughed heartily.


Carlene's Fantasies

“Maybe it runs in the family, Aunt Betty,” said Carlene with a gleam in her eye. “I’ll always remember a few years ago when you told me how you like to punish unruly boys by making them wear a pretty bow in their hair. I was only about eleven or twelve at the time, but I remember being fascinated by the idea. I went home and imagined being in your shoes….only I imagined more than just the bow treatment…." Carlene paused, and Betty sensed that she wanted to go on, but might have felt a bit uneasy doing so.

“It’s okay, Carlene, you can tell your Aunt Betty. If it’s any help, I think I felt the same way, even when I was as young as you were.”

Carlene smiled and continued. “Well, I had some….some naughty thoughts.”

“Please, go on,” prodded her aunt. “Tell me what you imagined.”

“Well, here's what I imagine. And I've done this quite often. Don’t get me wrong, it's not really bad. But after I put the bow on his head and see how red he is and how much power I have over him.…I tell him I am going to take his punishment a step further. I watch the look of terror in his face when I tell him that he is going to have to spend the day wearing only his underpants. I imagine a slow, excruciating strip as I take my time in doing the dirty deed myself as he stands there shamefaced and humiliated to the max while I peel his clothes off." Carlene paused and looked at her aunt for a reaction. She took in her wide-eyed, grinning face, which added fuel to her fire. She continued. "I start with his shirt. I want him bare-chested and feeling his nakedness right away. I pull his shirt tail out of his pants and slowly unbutton it. I see he is wearing an undershirt, which I like, since it gives me another article of clothing to strip him out of." Betty Richards giggled, which spurred her niece on. "I toss his shirt aside and pull his undershirt from his pants. I take the bow off so I can get his shirt off, and momentarily set it aside. 'Raise your arms,' I say. He does so halfheartedly. 'Nice and high,' I command. When he complies I say, 'Good boy,' and I slowly pull his undershirt past his outstretched hands. I replace the bow on his head. I look at his red face, pat him on the chest and kneel down, then meticulously remove his shoes and socks. I look up at him and smile, maintaining eye contact while I undo his belt buckle."

"Oh, Carlene!" exclaimed her aunt. "I'm loving the detail!" Indeed, Betty Richards' state of arousal was ever increasing as her niece wove her titillating tale.

"I unsnap his trousers and pull down his zipper," continued Carlene, unabated. "I slide down his trousers, exposing his underpants. His underpants are always the little white briefs when I do this—they call them tighty-whities. I think that makes it more embarrassing for him. There is more skin exposed, and I can imagine the outline of his penis in his briefs. And he always a little penis. Again, more embarrassing for him.

"Anyway, I have him lift his legs one at a time while I pull his trousers completely off. I stand back and grin while I look him up and down. Then I tell him to go back to his seat and that if he behaves, then he can have his clothes back at the end of the day. I picture him sitting at his desk, all red-faced, knowing that everyone in his class is staring at him."

"Oh, yes," admired the teacher. "That does paint a very interesting picture, indeed."

Probably encouraged by her aunt's interest, Carlene delved further into her fantasies. "Um...." she said. "I don't know if I'm going too far, but I....well, sometimes I....I don't stop there."

She looked at her aunt, and was heartened by her countenance, and then by her response. "Oh no, Carlene, you haven't gone too far at all. To the contrary. You have a vivid imagination, and you're just exploring your creativity. By all means, feel free to just let go. It's your Aunt Betty you're talking to."

"Thank you, Aunt Betty. I feel like I can open up to you, and I knew you'd get it. What I was going to say, was....well, sometimes when I have these....I guess you can call them fantasies....when I have these fantasies, I....like I say, I want to take it a step further, and....well, I get the boy totally naked." Again Carlene looked over to her aunt, hoping for her approval. When Carlene took in the knowing grin on her aunt's face, it was all the motivation she needed to carry on. "I have two different ways I use to getting him naked. Do you want to hear both of them?" asked Carlene.

Is the Pope Catholic?

"Please," urged the teacher. "Pray tell."

"Okay, well the first one happens a few minutes after he takes his seat in his underpants. His seat is somewhere in the middle of the room, so everyone has the best chance to see him. I let him sit there for a few minutes, all red-faced and humiliated. I'm giving a lesson, then I pause and casually say, 'Stevie'—there is a boy named Steve that I went to elementary school with. I think he's cute, and he has kind of a baby face. I would love to see this happen to him, so sometimes I use him when I do this.

"Anyway, I say, 'Stevie, I'd like you to put your underpants on top of your desk.' He looks at me all horrified. He doesn't think I really mean it. So I continue to pause the lesson and just stare at him. 'I'm waiting,' I say. So everyone watches as he reaches down, slips off his underpants and puts them on his desk. If he felt a bit humiliated before, well, now he is totally nude, and mortified to the max.

"I let his underpants sit on his desk for a few minutes, so he can look at them right in front of him. Also I think it's a good visual for everybody. Except Stevie, of course. <giggle> He is just praying that I tell him it's okay to put them back on. But instead, I casually walk down his aisle while reading aloud from a text book. I stop for a few moments when I reach his desk, just to savor the scene. Then I start walking again until I reach the back wall. I turn around and slowly walk back up the aisle. I'm still reading aloud, and as I walk by his desk I nonchalantly gather his underpants from his desk and continue walking. I hear the students giggle and picture the tormented look on Stevie's face. I turn around and smile at naked Stevie. He does not smile back. <giggle> His face is so red, he's fidgeting around, and....well, he's all naked in front of me and all his classmates! I have to say, I get a bit....a bit excited down there...."

The teenager broke off and blushed, prompting her aunt to try to put her at ease.

"It's okay, Carlene," said Miss Richards while putting a hand on her niece's shoulder. "It's quite a normal reaction, and nothing to be ashamed of. I know exactly how you feel. Don't worry, just enjoy yourself while you use your imagination and explore your fantasies. It's quite harmless, and it will bring you a lot of pleasure."

"Thanks, Aunt Betty," said Carlene. "You're so easy to talk to about things like this."

"It's my pleasure, Carlene," answered Betty Richards, quite truthfully.

Carlene paused while regathering her train of thought. "Do you want to hear the second way I get him naked?"

I do believe the Pope is still Catholic.

"Of course, sweetie," answered the teacher. "Don't hold back on my account."

"Okay, well the other one is pretty simple. I strip him while he is still standing there. Even though I told him that I would make him spend the day in his underpants, after I take his pants off, I take him totally by surprise and swiftly pull down his undies. Of course, then I pull them completely off. The shock effect of suddenly being totally naked really adds to it, I think.

"Oh, I forgot to mention....like I said before, he always has a little penis. You might even say a tiny penis. But I forgot to say that he hasn't grown any hair down there yet. I think that adds to his embarrassment, don't you?"

"Yes, absolutely," said Miss Richards. "Of course, it depends on his age. How old is the poor boy in your....your fantasies?"

"I always picture a boy in early high school. About fourteen," answered Carlene.

"Oh, in that case if he's still prepubescent, then he absolutely will feel extra humiliation. Quite a bit, actually," she said with a smile.

"I think so, too. So of course the first thing he does is cover up his hairless little penis with his hands. I say, 'Put your hands on your hips, and keep them there until I say otherwise.' He does so, and then I look down at his little pee-pee, then back up to his face.

"I usually don't get any further than that. It’s hard to explain, Aunt Betty….but the feeling of power to totally humiliate him, and the picture in my mind of him standing there wearing nothing but a pink bow and blushing crimson….I get a tingly feeling all over."

Betty Richards smiled. Though rather surprised with her niece's revelations, she quite enjoyed them and also felt a new kinship with her. "I totally understand, Carlene. As much as I enjoy the bow treatment, I've always wondered what it would be like to take matters a little further. And after listening to you I might just have to do that someday."

"Maybe you should, Aunt Betty," laughed Carlene. "And if you do, please don't be shy about telling me all about it."

"It's a deal," answered her aunt.

Little did Betty Richards know that in a few short weeks her opportunity would be handed to her on a silver platter.


A Call For Help From Aunt Betty

Considering her previous conversation with Carlene, one can readily see how Betty Richards would have no reservations about asking her niece to participate in Tommy’s humiliation. So after she and Sister Ruth came up with their scheme, Betty called Carlene on her cell phone.

“I’m going to be disciplining a thirteen-year-old student of mine this afternoon,” she began coyly. “It will probably involve the removal of some of his clothing—well, eventually, all of his clothing—and I was wondering if you might be interested in standing by in case he decides to make a run for it.”

Of course, the fifteen-year-old was quite interested. The teacher had to hold the phone away from her ear during Carlene’s boisterous response, as she pleaded with her aunt to let her be involved from the beginning.

“Have patience, my dear child,” answered Miss Richards. “I’ll make sure you are around for the grand finale, no matter what. In the meantime, I need you as a backup. I’m guessing you’d have to overpower him with your size. I think it is possible that you will get your chance for a little one-on-one discipline before we have him stripped completely naked.”

So when Tommy turned away from Karen to make his ill-advised but understandable escape attempt, Betty Richards wasted no time. She reached for her cell phone, and while giving Sister Ruth a knowing wink, she called her anxiously awaiting niece. Carlene, who was outside the building doing deep knee bends, managed to answer before the first ring tone was completed.

“Aunt Betty?” she said breathlessly.

“Yes, dear, it looks like the little culprit indeed is making a run for it,” said Miss Richards. “If you could intercept him and return him to the gymnasium, we would all be grateful.” Betty Richards smiled to herself, knowing that the recipient of her phone call was quite grateful herself.

“I’m on it!” shouted Carlene excitedly.

“Excellent. The girls just caught up with him, but I’m going to release him to you. Call it an early birthday present, and a reward for waiting so patiently. Now if you hurry, you might catch him as he’s coming out the door. If he gives you any trouble, feel free to use any means necessary to control him. Oh, and by the way, he's already stripped to his underpants.”

“YES!” screamed Carlene while ending the call excitedly.

Laughing with pleasure, she made a beeline for the building while her teammates watched her in bewilderment. Carlene pointed at an exit door as she ran by it. “Watch that door!” she yelled back to her teammates. “If a boy comes out, don’t let him get away!” She ran a few more steps, and yelled back once more. “He's only wearing underpants!”

Carlene heard the animated reaction and laughed heartily to herself as she breathlessly sped toward the school entrance.
TeenFan
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Re: Tommy's Debasement

Post by TeenFan »

No matter where Tommy runs he's going to be surrounded.
I wonder if the school has a basement. Tommy could run there to try to hide, but eventually the debasement would
continue in the basement.
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Re: Tommy's Debasement

Post by imanewb »

TeenFan wrote: Mon Dec 18, 2023 10:33 am No matter where Tommy runs he's going to be surrounded.
I wonder if the school has a basement. Tommy could run there to try to hide, but eventually the debasement would
continue in the basement.
I wonder how much more trouble he'll be in at home / the next day when his sister turns up with a black eye after all setting things into motion (from T's perspective)
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Tommy's Debasement, Chapter 18

Post by Blondie »

Image

Chapter 18: Submission to a Volleyball Player

A Short-Lived Escape

Meanwhile, Tommy had mixed emotions as he shoved open the door to exit the gymnasium. On the one hand he felt a strong sense of relief, having narrowly escaped the forfeiture of his underpants at the hands of the devilish Karen and her impassioned coeds.

On the other hand, he wasn’t out of the woods yet. After all, he was in his underpants, and his clothes were inside the gymnasium, a place he had no intention of revisiting any time soon.

Also gnawing at him was the question of why Miss Richards ordered the girls to let him go. Was it a moment of compassion? It seemed unlikely to Tommy, as he observed firsthand how much enjoyment his sadistic teacher was deriving from his humiliation.

But Tommy had more immediate concerns. Foremost on his mind was finding something—anything to cover his near-nakedness. He flashed on an old pair of overalls he spotted on the shelf in the cloakroom in the back of his classroom. He saw them earlier that day during that excruciating experience when he had to strip down and get into the nightgown at Sister Ruth’s behest. Yes, the overalls would be just fine, thought Tommy.

The gymnasium door clicked shut behind him, leaving him alone (or so he thought) in the long, L-shaped hallway. There were only two directions Tommy could go: to the left, which led to an outside door, or to the right, which led to the classrooms.

Tommy pulled the pink bow from his head, uprooting at least a couple of hairs. As he threw the bow against the gymnasium door, he made a beeline to the right.

Yes! Home free! I did it!

Feeling liberated, he increased the pace of his barefoot gallop. The splat-splat sound of his feet hitting the hard floor resonated throughout the otherwise quiet hallway. His classroom was right around the corner.

But when he reached the corner and turned left, he ran smack dab into a wall of flesh.


An Amazonian Antagonist

“Going somewhere, little boy?” came the voice about half a foot above his head.

The stunned Tommy looked up to see a derisively grinning fifteen-year-old girl. The auburn-haired Carlene was nearly six feet tall and athletically built, and to Tommy she looked positively Amazonian. Her volleyball uniform consisted of extremely short, tight, spandex shorts, and a matching crop top that was more like a sports bra.

Tommy backed off and stared at her, as he was momentarily mesmerized by her size, her beauty, and mostly by the expanse of exposed skin.

Carlene broke the silence. “Want to take a picture?” she joked. She started walking toward Tommy, holding out her hand. The leery Tommy, still staring at her bare midriff, backed up, matching her step for step. He instinctively covered the small protrusion in his underpants with both hands. Carlene grinned, both at the ineffective attempt at modesty, and at the improbable, somewhat surrealistic scene. “Here, take my hand,” she said. “We need to go see Miss Richards. She is not happy with you for ditching her class.”

It was all Tommy needed to hear. With a terrified look on his face, he turned and ran as fast as he could. It was just the reaction Carlene expected—and hoped for.

“I wouldn’t do that if I were you!” she yelled after him while slowly, confidently walking in his direction. Tommy passed by the gymnasium door and raced towards the exit. “I’m warning you!” cautioned Carlene. “You’ll be sorry.”

But Tommy was ready to take his chances with his only logical alternative. He pushed open the door leading outside…...and stopped in his tracks. There, standing and facing him not more than ten feet away, were a dozen grinning high school girls, all dressed exactly like the girl he was running from.

“Let’s get him!” shouted one, and they collectively made a move toward the door.

The beleaguered Tommy turned back inside and pulled the door closed. It automatically locked from the inside, so he had at least temporarily dodged a bullet. But he turned around to face the fleshy Carlene, who was twenty yards or so away, walking toward him and smiling menacingly.

Tommy turned back toward the exit. He put his ear to the door, and could hear the girls right outside, still giggling at what they had just witnessed. He turned back to Carlene, who was slowly but surely closing in on him.

Unsurprisingly, reacting like a trapped animal, he charged towards his pursuer. Hoping to somehow squeak by her, he faked to her left and veered to her right. It was child’s play for the athletic Carlene. She grabbed Tommy by the right ankle, and he went sprawling, hands first to the floor. Tommy jumped up, and Carlene, toying with him like a cat with a captured mouse, grabbed his ankle just as Tommy started running. Again he fell to the floor. Tommy tried crawling away, and the giggling Carlene grabbed the back waistband of his underpants. For Tommy, it was the second time in less than five minutes that a girl controlled him by grabbing onto his underpants. His movement forward naturally caused his underpants to be pulled halfway down his buttocks.

Tommy, now desperate, was ready to fight tooth and nail. He stood up and started flailing madly at his antagonist. “Oh, you’re quite the feisty one,” laughed Carlene as she effortlessly fended off Tommy’s wild swings. While she had a hold on his wrists, Tommy kneed her in the thigh, temporarily jarring her, allowing Tommy to break free. “Fuck! That’s gonna bruise!” screamed Carlene, while Tommy reached back to pull up his underpants and started running in the direction of the classrooms. “Alright, you’ve pissed me off now, you little shit.”

Within a matter of seconds Carlene closed the gap, wrapped her arms around Tommy’s chest from behind, and pulled him to the ground. Tommy continued kicking and struggling, but he was no match for the powerful girl. In short order Tommy found himself on his knees in a scissors lock, his head securely fixed between Carlene’s muscular thighs. Carlene was standing up, facing Tommy’s back, with a firm grip on both of his wrists.

“Are you ready to go back to the gym now?” she asked.

“No! Please, let me go!” came the muffled response.

She squeezed her thighs together a little tighter. “Last chance, little boy. Are you ready?”

“No! Let me go!”

It was music to her ears. “Okay, time to teach you a lesson.”


Spanked Into Submission

Carlene lowered her knees to the ground, maintaining her hold on Tommy’s head. She then inched her way towards Tommy’s backside, keeping his torso clinched between her thighs. When she reached his mid back, she lowered her weight to a sitting position. Tommy braced himself with his elbows to the ground to keep his face from mashing into the floor, while his backside jutted out prominently. He tried using one hand to push her away, but his efforts were fruitless. Carlene grinned, knowing that she was free to do whatever she wanted to her captive, and that he was totally helpless to prevent it. She licked her lips in anticipation, and without a word she hooked her thumbs under the back of Tommy’s waistband and ever so slowly started lowering his underpants.

“No! Please!” cried the embattled Tommy as he was introduced to yet another humiliation. Even though the experience was becoming all too familiar, for Tommy the humiliation effect was no less severe than before, especially with a new person involved. Tommy struggled mightily, but with Carlene’s weight and leverage advantage, there was no stopping her. She continued with the slow but steady descent of his underpants, until she reached an impasse with his knees on the floor.

“Lift up your right knee.” Tommy sat motionless, and Carlene simply reached around Tommy’s back with her dominant left hand and squeezed his nipple as hard as she could. Tommy cried out in pain and lifted his knee. When he did so, Carlene shoved the right portion of his underpants under his knee. “Now the left one,” she commanded. Tommy needed no further prodding, and he lifted his knee while Carlene slid the other side of his underpants to his shin. “That’s a good boy,” she teased. She silently, slowly slid his underpants down his leg, then over his heels. She left them scrunched up near his toes, precariously close to coming completely off. She heard a muffled yelp from her victim.

Yes! I’ve got him right where I want him….now let’s get these underpants down.…oh, yes, this is just awesome!.…look at him struggle while I pull them down.…he’s just hating this..…so cute, he’s so smooth and white….his little cheeks won’t be white for long.….oh, Aunt Betty, I owe you, BIG time!….talk about a fantasy come true.…I’m getting that tingly feeling again, only it’s better than ever.…this is the real deal, not a fantasy....I'm looking at his naked flesh....I’m think I’m actually getting damp down there, I can’t believe it….okay, let’s get your knee up….oh, he won’t do it willingly.…he’s hanging on to his little undies for dear life..…a pinch on the nipple should do the trick.…yes, there we go.…now the other knee.…excellent…just slide these aaall the way down.…I’ll leave them just over his toes.…give him something else to worry about while he’s getting spanked..…oh, listen to him, he’s positively frightened.…I would be too, if I were you, my little friend.

“Are you ready to find out what happens to naughty boys?” she said, smiling with pleasure.

“No…please…” was pretty much all Tommy could muster at the present stage of his wretched predicament.

“Straighten your legs out.…go on, lay down, completely flat.…all the way down.…that’s it, perfect….now, push your knees into the ground and lift your hips up a little bit.…come on, you can do it….there.…a little more.…excellent, your bottom is sticking up juuuuust right,” she cooed while gently caressing Tommy’s derriere. Carlene continued stroking the bare behind in front of her. “Such cute little white buns.…and so nice and smooth.…since you’ve been so naughty, we’ll warm them up reeeal good for you….we’ll turn your little cheeks nice and rosy, yes we will.” Carlene rested her hand on her thigh and then sat still and quietly, mainly to savor the moment, but also to add to the anguish of her victim. Tommy’s rapid, heavy breathing betrayed his extreme anxiety.

A full forty-five seconds went by before Carlene leaned over, gently pulled his buttocks slightly apart, then delicately blew into the crevice of her intended target for a few seconds. She leaned back and smiled as Tommy clenched his cheeks together. She waited a few more seconds before deciding the time was right.

Let’s see, I need to reposition him….like he is, his little ass might be a bit too bony.…a good spanking should be on some nice, fleshy skin….let’s lay him down flat, see what that looks like….ah, he’s putty in my hands, doing everything I say now.…that’s better, but let’s stick his butt up just a little bit.…yes, perfect….it’s ready for me now.…my, what a beautiful sight….oh, feel how smooth it is.…it’s so fun to tease him….what must he be thinking right now…can you imagine how nervous, and how humiliated he must feel?.…I can’t wait to tell Aunt Betty all about this wonderful experience….she’ll want to hear all the details, I’m sure.…okay, I think I’ll sit back and take this in for awhile.…enjoy it….and make him sweat a little bit.…listen to him breathing so fast.…what a treat….I’ll wait a little longer….it’s so quiet now, except for his breathing.…pretty soon, all hell is going to break loose.…I think I’ll blow into his little butthole.…pull these cheeks apart a bit....and a gentle, loving sensation for him to feel before he gets spanked silly.…oh, look at him tighten up.…this is just delicious!.…okay, I’m ready.…I’ll wait juuust a few more seconds.…the calm before the storm.

The sound of the sudden strike reverberated through the hallway, as Carlene counted ten steady, hard smacks to the left cheek of Tommy’s backside.

Slap! Slap! Slap! Slap! Slap! Slap! Slap! Slap! Slap! Slap!

“That was for not taking my hand when I asked you to.” She paused and smiled with satisfaction as Tommy squirmed underneath her. “Keep those hips up!” Tommy lifted his hips, and Carlene continued. “And this is for running away from me.”

Slap! Slap! Slap! Slap! Slap! Slap! Slap! Slap! Slap! Slap!

Ten more smacks, this time to the right cheek. Tommy bent his knees and kicked his legs throughout, and somehow managed to finagle his underpants safely to his shins. “Ow! Ow!” he screamed.

Tommy struggled with more intensity, much to Carlene’s amusement and stimulation. She giggled as the traumatized skin reddened before her eyes. But she wasn’t done. “Hips up!” Tommy complied, and braced himself for another onslaught. “This is for fighting with me after I caught you.”

Slap! Slap! Slap! Slap! Slap! Slap! Slap! Slap! Slap! Slap!

Again, ten more swats, this time alternating from cheek to cheek. There was only a moment’s hesitation before the next barrage came, in the same fashion, only with more relish. “And this… this is for the bruise!”

Slap! Slap! Slap! Slap! Slap! Slap! Slap! Slap! Slap! Slap!

It felt to Tommy like his backside was on fire. “Ow! Oh God! Ow! Ow! Oh! Oh! No more! Please!” Tommy gyrated his hips and kicked his legs wildly.

Carlene was flush in the face, partially from exertion, but more from stimulation.

Oh, I’m loving this!….look at him squirm while I’m spanking him.…and we’re just getting started.…I love the feeling of power….listen to the slapping sounds….it echoes in the hallway….okay, a second dose of ten, this time on the other cheek.…get those hips up, little boy.…that’s it….ah, his cheeks are turning pink.…he’s making noise now, that didn’t take long….he managed to get his underpants to his legs.…I see where his priorities are.…here comes another ten.…I’ll alternate cheeks this time.…oh, they’re getting redder by the second….this is great!.…my hand stings—imagine how HE feels.…okay, these last ten are coming, as hard as I can.…whew!.…that had to hurt….he’s really thrashing about now.…and listen to him....I think I got my point across.…oh, God, that was awesome!

Carlene took a few breaths and, quite satisfied with herself, addressed the whimpering lad as she rose. “Stand up, little boy, I want to talk to you,” she ordered. Tommy, keeping his back to Carlene, quickly got to his feet and, while jumping up and down from the pain, he immediately reached down for his underpants. “Uh-uh-uh!” warned Carlene. She grinned at the amusing scene, and his colorful derriere. “You can leave those right where they are while I’m talking to you. And turn around and face me.”

Forced into subservience, Tommy complied. He wiped a few tears from his eyes and turned around, clutching his privates. Still throbbing from the spanking, and apprehensive about his nudity, Tommy shifted his weight back and forth from foot to foot.

Carlene delighted in the scene and smiled, as Tommy’s blush increased by the second. It was just like her imagined scene that she had related to her Aunt Betty a few weeks before, only exponentially better, since her victim was in the flesh.

She bent at the waist, put her hands on her knees and her face close to his. “Now here’s what we’re going to do, little boy. You and I are going to march into that gymnasium and report to Miss Richards,” she said while pointing to the door. “You can walk in willingly, or I’ll carry you in there myself. If you choose to do it the hard way, then your underpants are coming off and you’ll be carried in there buck naked.” Carlene stood up and continued addressing the miserable lad. “Maybe before that I’ll let my teammates in here so they can have some fun with you first.” Tommy’s eyes widened at the suggestion, bringing a smile to Carlene’s lips. “Well, what’s it gonna be, little boy?” Tommy nodded his head sullenly. Carlene would not let him off easily. “I didn’t hear you. Do we need to remove your underpants?”

“No! I mean…I mean, yes…I’ll…I’ll go…”

“Okay then. Now pull up your tighty whities and let’s go inside.”

Oh, how funny!.…look at him hopping around.…this is hilarious, I’m just loving it!….my hand still stings, but it was sure worth it..…those underpants are staying down….I want to see him squirm some more.…now I’ll have him turn around….oh yes, this is choice.…he’s still bouncing around, and he’s covering his little penis, just like I told Aunt Betty the little boy would do when we talked in the park.…and he’s blushing so much.…well of course he is.…I think I’d just DIE if I were him right now.…I can’t even imagine!


The Dreaded Bow, and a Peek From Carlene

Tommy turned away from Carlene before reaching down and hurriedly yanking up his underpants. The smiling Carlene took Tommy by the hand and led him back down the hallway toward the gymnasium door. The defeated Tommy walked along grudgingly. He gloomily stared at the door as they walked, knowing that once he entered, a most miserable fate awaited him.

“I have a feeling we’re going to make a lot of people very happy, don’t you think so?” asked Carlene. No answer was forthcoming from Tommy, but that didn’t stop Carlene from continuing her banter as she merrily escorted her captive. “I wonder what kind of punishment Miss Richards has in store for you for cutting out of her dance class? Hmm, let me take a guess.…do you think it might involve the removal of a certain article of clothing?” She smiled as she turned and watched Tommy’s face redden. “Do you think she’ll make you dance around naked in front of the whole class?” Again she looked down at Tommy, and again she delighted in his increasingly flushing face. “I’d really like to see that," said the smiling Carlene as she treated herself to the mental image.

They reached the door, and Carlene reached down to pick up the pink bow that Tommy had tossed aside just a few minutes before. She looked at it curiously. “What have we here?” mused Carlene. “I see my Aunt Betty is up to her old tricks.”

Tommy flinched at the revelation, but wasn’t the least bit surprised to learn that the two demons were related.

"Let's get this pretty bow on your pretty little head," she said. Carlene meticulously fastened the bow to Tommy’s head, then leaned back to admire the effect. “Oh, how darling!” she exclaimed while tweaking Tommy’s now crimson cheek with her thumb and index finger. “Aren’t you just pretty in pink?”

Chuckling to herself, she started to open the door, then hesitated when she was hit by an impulse. She kneeled down to the floor in front of Tommy. “Before we go in, I simply must see what you’ve been so desperately hiding from me.” She reached for Tommy’s waistband, and he immediately tried to push her hands away. Carlene grabbed Tommy’s wrists and pulled them toward her. “Put your hands on my shoulders,” she directed. When he did so, she said, “If you dare interfere with me again, I’ll blister your little buns like never before, and I can guarantee you’ll be walking through that door showing off all four of your rosy cheeks.” She smiled at Tommy’s now submissive demeanor, and was confident that she could continue unimpeded.

"Please....please don't do this," begged Tommy as Carlene reached for his waistband.

"Oh, it'll be okay. I'll just have a little peeky weeky here," she said as she pulled open Tommy’s waistband, leaned forward and peeked inside.

The anguished Tommy felt her hair brushing against his stomach and could even feel her breaths on his most private parts. He listened to her giggle as she continued staring into his underpants for what Tommy thought was an inordinate amount of time.

While still holding his underpants open, she put her face close to his. “Now I know your little secret.…your tiny, little hairless secret,” she teased.
She grinned as Tommy looked downward and somehow blushed even brighter. Carlene followed Tommy’s gaze and they shared one last look before she gently replaced the waistband to his midsection. She gave him a couple of love taps on his bare tummy, then stood up and looked at him with a wicked grin. “You’ll just die of embarrassment if they all see that, won’t you, little boy?” With that, she took Tommy’s hand and started to open the door to the gymnasium.

Yes, I’ll take him by the hand and walk him back to my aunt and all of his classmates.…I’m sure they’ll be happy to see him.…oh, look at him blush while I tease him.…especially when I brought up dancing naked.…wouldn’t THAT be fun to watch….I hope Aunt Betty has that in her plans.…ah, look at the pink bow….he must have taken it off….one of my aunt’s favorite punishments….now I get the pleasure of pinning it on his pretty little head.…wow, I see what she means….he’s blushing even more while I do this.…oh, this is rich!.…look at him squirming around….the boys must really hate this.…I must say, it looks kinda cute on him.…he has such soft features.…I could make him look like a pretty girl….if I only had some lipstick….and some little panties..…maybe Aunt Betty will let me borrow him for an evening.…I’d really have fun disciplining him….I’d have him prancing around in my little sister’s panties….and her training bra.…what do they call that?.…oh yeah, “petticoat punishment,” I think….I love the idea….he would hate it and he’d look adorable.…and I’d let my little sister join in the fun….she’d be all over it….we’d really have him blushing crimson.…oh, here I go again….I’m letting my dirty little imagination run wild….and I’m getting myself all hot and bothered.…okay, Carlene, back to matters at hand...let's get you inside....wait....one last humiliation for you before we go in....let's check out the merchandise.…he’s been so careful to make sure I don’t see it…sorry, pretty boy, but I’m going to make it happen.…oh, he’s pushing my hands away.…I’ll give him one warning.…touch me again and that last spanking will seem like love taps compared to what you’ll get……not only that, I’ll strip these off and haul you in there butt naked.…yes, I thought you’d see it my way.….get your hands on my shoulders.…that’s it….clear sailing now….oh, he's begging me....he SO doesn't want me to do this....sorry, my little playmate, it's going to happen....here we go….just pull open this elastic band and peek inside….this should be inter….oh!.…it’s so tiny!….look at that little thing!.…and it’s totally hairless!.…it’s like an eight-year-old’s….oh, this is too much!.…poor boy, no wonder he didn’t want me to see it.…and such cute little balls.…like little cherries….he’ll absolutely die of embarrassment if they all see this….oh, Aunt Betty, strip him naked, in front of everybody.…totally naked!....make him dance, and we can all watch his tiny bits jiggle around.…I’m sure he’s just hating this.…I think I’ll keep holding these open and keep staring, just to make him squirm.…it IS a cute little thing….cute as a button.…and not much bigger.…I saw my boyfriend’s once when he was peeing, and his is at least twice as big….look how it’s so small that it’s pointing straight out, not even hanging down….poor little boy.…okay, just a few more seconds.…look, he’s moving his hips around.…he’s really getting antsy….I’m sure he’s thoroughly humiliated by now.…I’ll look up at his face….oh, yes, he’s red as a beet.…that’s right, my humiliated little friend, I’ve been staring at your hairless little pee pee.…oh, he’s looking down there, too….we’ll share one last look.…together.…oh, that was special….he knows I caught him peeking at his own little bits….and his face got even redder.…what a treat this is!....okay, my smooth little friend, let’s go show you off to all your admirers.


Invasion of the Volleyball Players

Just as Carlene was about to push the door to the gymnasium open, she had an inspiration, one that brought a huge grin to her face. "How would you like to make some more friends before we go inside, pretty boy?" asked Carlene as she eyed the exit door.

Tommy followed her gaze and immediately comprehended what she had in mind. He shook his head vigorously. "No! Please!"

"That was a rhetorical question, my dear. I'm pretty sure you'll find that my teammates will be quite friendly, and very excited to meet you."

She punched a couple of buttons on her cell phone. In a matter of moments the recipient picked up. "Hey Carlene!"

"Paula, are you all still out there?"

"Oh yeah, we've been listening at the door. What the hell has been going on in there? I heard a lot of slapping sounds. Was that what we think it was?" asked Paula excitedly.

"It was," responded Carlene with a chuckle. "My little friend here required a little attitude adjustment. But he's completely under my control now."
She pulled the phone away and addressed Tommy, who state of misery was quite apparent in his expression. "Aren't you, little boy?" Tommy looked downward, and Carlene smiled while putting the phone back to her ear.

"Anyways, how would you all like to join us?"

"YES!" came the boisterous response from the other end.

The laughing Carlene disconnected the call and looked down at Tommy. "The girls are very anxious to make your acquaintance."
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