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.
