Underpants Memoirs

Stories about boys ending up in compromising situations, preferably naked and embarrassed, as the name suggests.
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Underpants Memoirs, Chapter 7

Post by Blondie »

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Chapter 7: The Tighty-Whities Twins, Part 1

I would be remiss if I didn’t devote a chapter of these memoirs to the two boys who were humiliated on the bus—not just once, but on multiple occasions during my first year. I was lucky enough to witness their very first stripping.

Normally, I got a ride home from my mom, but one afternoon she had some kind of engagement, so I was stuck taking the bus—something I wasn’t exactly thrilled about. As it turned out, I owe my mother a ton of gratitude, because her timing was perfect. If not for her, I would have missed one of my all-time favorite strippings.

The boys in question weren’t related, but they became known as “the twins.” (And later, more famously, as the "tighty-whities" twins.) The nickname fit—not just because they were always together—they seemed almost inseparable—but because of their uncanny similarities. Even their names sounded alike: Eddie and Teddy. Both were fair-haired and youngish-looking—they could have easily passed as 12-year-olds—with slender physiques. Unfortunately for them, they fit the mold of a potential Roosevelt victim through and through.

I first had an inkling they were being targeted the day before the incident. I was sitting toward the front of the bus, just in front of a group of six older girls. They were all sophomores, and they were all taller and stronger than either of the boys. And luckily for me, they were loud enough that I could hear everything.

“See those two boys back there?” one of them said. She was clearly the ringleader. Her name was Melanie. “Those blond-haired kids that always sit together?”

“Yeah, you mean the twins?” replied another.

“Oh, are they twins?” Melanie asked. “They do look a lot alike.”

“Nah,” the girl said. “They’re not related. That’s just what everybody calls them.”

"Anyway," said Melanie, "What do you say we have a little fun with them?"

“Sure, Melanie,” giggled her friend. “They look like little lambs. Should be easy peasy japanesey.”

“I know,” Melanie giggled back. “We’ve never pantsed two at the same time. Think of it—we can double our pleasure.” That got a round of laughter from the whole group. My eyes widened. Two boys, stripped and humiliated by a pack of girls? I could hardly believe my luck.

“We’re almost home,” Melanie continued. “Let’s do it tomorrow. That way we’ll have more time to admire them in their undies. And more time for them to be embarrassed.”

“Sounds good,” another girl laughed.

“I hope they’re wearing tighty-whities,” one chimed in.

“We’ll find out soon enough,” Melanie said, just as the girls rose to get off at the next stop, still giggling.

I knew right then and there that I would tell my mother that I would be getting a ride home from someone else the next day. I had to be on that bus.

* * * * *

The new day dawned, and my enthusiasm was off the charts. The school day seemed to drag on forever. When it finally ended, I practically skipped to the bus. I grabbed a seat near the back, where I figured all the action would take place.

Within moments, the two boys—completely oblivious to the humiliation that awaited them—sat down together directly across from me. I licked my lips in anticipation.

Soon enough, the six girls from the day before came striding down the aisle, stalking their prey. Melanie was in front, leading the way. She stopped in front of the boys and looked down menacingly at the one in the aisle seat.

"You're in our seat," she said coolly.

He looked up and surveyed the six sophomore girls towering over him. He stood up at once, as did his friend. But Melanie quickly pointed at the boy by the window.

"You stay there," she said, and the little lamb immediately sat back down.

"Anna, maybe you can sit next to him and keep an eye on him," Melanie added.

"Will do," Anna replied cheerfully as she dropped into the seat, flashing a grin at her new seatmate.

The first boy made a motion to move to the front of the bus—he probably wanted to get as far away from the intimidating sixsome as possible—but Melanie wrapped her arm around his shoulder and led him toward the long bench seat in the very back.

"Let’s have a seat back here and get acquainted, shall we?" she said.

There were two kids already situated back there, but they sized up the situation and quickly dispersed. Melanie guided her victim to the center of the seat (which I very much appreciated, as they would be in plain view) and the remaining girls filled in around them, two on either side. Melanie still had her arm around the boy, who looked a bit frightened.

You have no idea, little lamb.

"I'm Melanie," she said sweetly. "You can call me Miss Melanie. What's your name?"

"Eddie," he said quietly.

"Nice to meet you, Eddie. And what's his name?" she asked while gesturing toward his friend.

"Teddy."

"Eddie and Teddy. That’s adorable. Is Teddy your twin?"

"No. Just a friend."

"You guys look so much alike, I thought you might be twins."

"Yeah, we get that a lot," said Eddie. "Please, I'd like to sit somewhere else."

"I mean, you're both cute little boys," said Melanie, ignoring Eddie's request. "Not very big, and you both look like you should be in elementary school. I'll bet neither of you have started puberty yet."

Eddie, of course, had no desire to continue the uncomfortable dialogue. But Melanie persisted.

"Have you? Started puberty, that is."

Eddie’s cheeks were just starting to flush, a faint pink creeping in. "Please, that's...that's personal."

"It is," Melanie agreed with a grin. "But I want to get to know you—inside and out. Have you started growing any hair on your privates? I'm guessing not, by the looks of you."

She looked him up and down, running her fingers along his arm. "No hair here," she murmured. She reached down and pulled his pant leg up to just above his knee and stroked his leg. "Nothing on these pretty legs either." She met his eyes. "I’ll bet you don’t have a single hair on your whole body, do you, Eddie?"

Eddie squirmed and yanked his pant leg back down. He was blushing deliciously.

Teddy, seated just ahead, was clearly listening—and just as clearly growing anxious. He tried to stand up, but Anna gently placed her arm across his lap and kept him in place.

"You can't go, sweetie," said Anna. "You're next."

Teddy didn’t know what next meant, but it had to sound ominous. He would find out in due time.

In the meantime, I'm sure it was agonizing for him to listen while his friend's sorry plight developed, knowing that he would more than likely face the same treatment.

When you think about it, it was ingenious on Melanie's part. The six girls could have easily overpowered the boys and stripped them both at once—but instead, they were drawing out the scene for their own enjoyment (and mine!). And Teddy would have to sit there in trepidation while Eddie is tormented, and then have to go through his own ordeal. Brilliant!

"Oh, you’re blushing, Eddie," Melanie cooed. "Does it embarrass you when I talk about your cute little body? Your smooth skin? How you have no hair?"

She stroked his arm again, and Eddie squirmed, his cheeks turning a deeper shade of red.

"Would it embarrass you if I took a look at your underpants?"

Eddie’s eyes widened in panic. "No! I mean yes...please, let me g..."

"Do you and Teddy wear the same kind of underpants?" interrupted Melanie.

"I...I don't know."

"It would be fun to find out, don't you think so?"

"No! Maybe just...just ask us," he stammered, sounding more than a little anxious.

"I could do that," Melanie said sweetly. "But it wouldn't be nearly as fun as exposing your little underpants for everyone, would it?"

(And by “everyone,” she meant practically the whole bus. Glancing forward, I saw heads turned, bodies kneeling on seats, most of them straining to watch. The Roosevelt bus driver? She could absolutely see it all in her mirror—and she was following the same M.O. as the teachers, by turning a blind eye. Chances are she was enjoying herself.)

Melanie gave a small nod, and one of her friends got up, knelt in front of Eddie, and reached for his shoelace. Eddie jerked his foot away.

"I wouldn’t do that if I were you, Eddie," warned Melanie. The warning was soft-spoken but carried a fair amount of impact, from Eddie's perspective. He sensed that Melanie was not someone to mess with.

He lowered his foot.

The girl untied one shoe, pulled it off, then slid his white sock off. She repeated the process on the other foot. Within seconds, Eddie was barefoot.

"Good boy, Eddie," Melanie said. "Now let’s get these pants down so we can have a nice, long look at your underpants."

She reached for his belt.

"What? No!" cried Eddie, grabbing Melanie’s wrists. "Are you crazy? We’re on the bus!"

He's so naive. And it's so delightful.

"I know," Melanie said, grinning. "Isn’t it great? I’m going to pull your pants down and show off your underpants to everyone here—and you can’t escape. I understand why that troubles you, Eddie. It’s going to be very embarrassing."

Again, Teddy tried to rise from his seat in front of Eddie, and again his efforts were easily thwarted by Anna.

Meanwhile, the now very anxious Eddie clung tightly to Melanie’s wrists. She didn’t seem fazed.

"Okay, here’s how it’s going to work, Eddie," she said coolly. "You’re going to let go of my wrists and let me have my way with you. When you do, I'm going to take your pants off. If you don't, I'm still going to take your pants off. Trust me, it’s happening either way—we’ve stripped boys bigger than you before, so it will be easy for us to strip you."

She leaned closer, lowering her voice just enough to chill him. "Now, if you cooperate, you’ll get your trousers back before you get off the bus. If not, after we forcibly remove them, we’ll toss them out the window and you will be finding your way home in your underpants."

Melanie let the frightened boy mull that over. After a few moments of silence, Eddie let go.

"That's a good boy," Melanie cooed. "You’re my obedient little lamb. And now you’re going to let me see your little underpants."

She went for his belt again. This time, there was no resistance.

"Can you just...just look without pulling them down?" Eddie fidgeted nervously. "I mean—can I keep my pants on? And you can look?"

Melanie shook her head with a playful sigh. "Well, Eddie, that might have been an option (I don't think so), but you made the mistake of resisting. All I wanted was a peek at your undies, but now? That ship has sailed, and you need to be punished. And your punishment is that you are going to be depantsed."

I leaned forward eagerly as Melanie popped open Eddie’s belt and unfastened the button on his jeans. She tugged his zipper down and parted the flaps, revealing the white material of his underpants.

She pulled up his T-shirt to his chest. "Hold this up for me, cutie pie, so we can all get a nice, clear view of your underpants once I pull your pants down."

Eddie—shaking now—gripped the shirt with both hands and held it up.

"Lift your bum," ordered Melanie.

Eddie raised his hips. In one smooth motion, Melanie slid his pants to his knees.

"No, please don’t!" Eddie whimpered—but it was too late. She kept pulling until his pants were bunched around his ankles.

"Isabella, would you do the honors?" Melanie said casually. "Eddie, hold out those pretty legs so Isabella can take your pants off."

"And Jenny," she added, "maybe help Eddie out of his shirt. I want him in just his undies. It'll be much more entertaining that way, and he'll look adorable. Eddie, make sure you hold your arms up nice and high.

"Teddy, how are you doing up there? Are you getting jealous because I'm paying so much attention to Eddie? Don't worry, I haven't forgotten you."

There was no response from Teddy, who was probably too terrified to speak.

I giggled while I watched the panic-stricken Eddie stick his legs out and hold his arms up in the air.

It happened so fast. Isabella tugged his pants completely off, flipping them inside out as they came free. At the same time, Jenny peeled his shirt over his head and tossed it aside.

Just like that, Eddie had been stripped to his tighty-whities.

For me, it was a sight to behold. For Eddie...well, the poor thing was practically hyperventilating. He bent forward, both hands clutched over his crotch, breathing fast, face burning.

Laughter and giggles rang out across the bus as Melanie looked him up and down, sizing him up.

"Eddie, look at you! You look so cute in your tighty-whities!" she said.

Indeed, he did. His smooth, hairless, untanned skin blended in deliciously with his white underpants. The only noticeable color was his brilliantly red face.

"Eddie," said Melanie, "why don’t you stand up and model your tighty-whities for us?"

Eddie didn’t move. But Melanie found a way to motivate him.

"Are you interested in getting your clothes back before you reach your stop?" she asked. "If so, you'll need to model for us."

Eddie was between the proverbial rock and a hard place, and his situation was hopeless. Ultimately he must have decided that showing off his underpants in the bus was more favorable than showing them off in the great outdoors.

Personally, I was quite happy that he made that decision. :lol:

He stood. Shoulders hunched. Arms wrapped tightly over the front of his underpants.

"Stand up straight. And move your hands away from your privates," ordered Melanie. "In fact, put your hands behind your head so we can all get a nice look."

Eddie obeyed, reluctantly interlacing his fingers behind his head.

I immediately looked down and grinned. There it was: a barely-there little bump in the front of his briefs. I glanced at Melanie—she’d noticed too.

Then she came up with a doozy.

"Good boy, Eddie. Now be a good little model and take a nice, sexy walk down the runway for us."

Oh, my goodness!

Eddie froze, visibly panicked.

Melanie reached down, picked up his trousers, opened the bus window, and dangled them outside. The legs fluttered in the breeze.

"In five seconds, I'm letting go," threatened Melanie. "One...two...three...

That did it. Eddie began his walk, and it was such a delicious scene.

The whole bus erupted into cheers, laughter, and squeals. Well, not from Eddie. Or Teddy, for that matter. Eddie’s face was as red as can be as he shuffled down the aisle, clad only in his tighty-whities. He stopped just short of the driver—who, by the way, did nothing to hide her amusement—then turned around for the torturous walk back.

When he reached the back of the bus, he stopped in front of Melanie and began to lower his arms.

"Wait," she said. "Keep your hands on your head."

She looked him up and down...and then locked eyes with him.

"Before I let you sit down," Melanie purred, "I’d really like to take a peek inside your tighty-whities."

Eddie's eyes were like saucers. He looked ready to faint.

Melanie placed her hands lightly on his hips, making him flinch.

"No...please...please don't!" he pleaded, voice cracking.

“It’s okay, Eddie,” she said with mock sweetness. I'm not going to molest you or anything. I just want to have a look."

And with that, much to Eddie's chagrin, Melanie casually tugged open the front of his briefs, peered inside and immediately burst out giggling. She continued to grin and stare, then looked up at the shamefaced lad with a wicked grin.

“You poor little boy,” she said derisively.

A chorus of laughter erupted around them, which became even more boisterous when Melanie, playing to the audience, held up her thumb and index finger about an inch apart.

Eddie’s face was glowing.

She let the waistband snap back against his stomach, making him flinch again—but Melanie wasn’t finished.

Gripping the hems of his briefs with both hands, she began slowly pulling them downward. Eddie practically jumped.

"Don't worry, Eddie," she said, pausing after lowering them just a couple inches. “I just want to pull these down a little bit so I can get a better look inside your tighty-whities. I could see your little pee-pee, but this way I'll be able to see your little balls a lot better," she said merrily.

She tugged the waistband open again and leaned forward, eyes glinting with mischief as she looked inside.

“Oh yes,” she giggled. “That’s adorable. And I can see everything so clearly—especially since you don’t have a single hair down there.”

Her voice carried loud and clear through the bus, triggering another round of cackling.

Two girls on either side leaned in, sticking their heads over Melanie’s shoulders for a peek of their own. All three girls broke into squeals of laughter.

“I wanna see too!” another one called out eagerly.

“Okay,” said Melanie with a playful grin. “The rest of you can have a look too. Eddie, be a good little boy and hold your undies open so the rest of my friends can check out your cute little bits.”

Red-faced and shaking, Eddie, in the throes of the humiliation of a lifetime, reached down, hooked his thumbs under the waistband, and pulled his briefs forward, holding them wide open as the other girls crowded in to gawk at his most private parts.

I so wish I was part of this group!

After they’d all had their look, Eddie let go and started to pull up his tighty-whities.

"Wait!" said Melanie. "I need to do one more thing. Hold them open again." He did, and Melanie said, "I simply must have a picture of this."

Melanie held her phone above Eddie's underpants and snapped a picture. She then went behind him, held the camera up again, but was not satisfied.

"Hmm, I can't quite get the angle I want. Here, you take my phone, and I'll hold open your undies for you. Then you take the picture."

Melanie handed the camera to the bedeviled Eddie. She snuggled her body close to his, reached around him with both arms, and once again pulled out his underpants.

"Okay, little Eddie," she said softly into his ear. "Get a nice picture of your smooth little bits for me."

In what had to be a surreal moment for him—I mean, it was for me—Eddie tilted the camera down, aimed it straight into his own underpants, and snapped the photo. Melanie let go of the waistband, plucked the phone from his trembling hand, and studied the image. Then with a mischievous grin, she held it up for him to see.

“Well, Eddie?” she purred. "What do you think? Look familiar?"

Eddie glanced at the photo, then turned away, crimson-faced.

“Okay, I’m done with you for now,” Melanie giggled. “You can take your seat. If you’re a good little boy the rest of the way, you can have your clothes back at your stop.”

Eddie yanked his underpants back into place and collapsed onto the bench seat, hunching over with his arms wrapped tightly around himself. The near-naked boy was shaking from the harrowing ordeal. His skin was flushed, his body was quivering—he looked completely shellshocked.

Melanie took one last look at the photo, then turned her gaze to Eddie. She smiled sweetly—almost tenderly—before giving his trembling knee a patronizing little pat. Then she turned, eyes already fixed on her next victim, who was visibly cowering in his seat.

Her smile widened.

“Next!”

To be continued....
Last edited by Blondie on Thu Jul 17, 2025 6:41 am, edited 1 time in total.
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Underpants Memoirs, Chapter 8

Post by Blondie »

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Chapter 8: The Tighty-Whities Twins, Part 2

When Teddy heard the word, "Next!" coming from the mouth of the wicked Melanie, his face went ghost-white. After listening to—and watching—what had just happened to his good buddy Eddie, there was no reason to believe he’d be spared.

Anna, seated beside him as part of Melanie’s gang, turned and smiled. "I think she means you, Teddy," she said cheerily. She took his hand and stood up. “Come on. Let’s go see what Melanie wants with you.”

Teddy had a pretty good idea what Melanie wanted with him—Eddie was sitting behind him, stripped to nothing but his tighty-whities, while Melanie’s hand casually caressed his bare thigh. Teddy yanked his hand away.

“I can go without your help,” he snapped.

Anna didn’t protest. She stepped into the aisle, allowing Teddy to rise from his seat. I don't know if he ever intended on going back there, but he took one look at the grinning Melanie sitting next to his red-faced, near-naked friend, then made a beeline toward the front of the bus.

I'm not sure what he thought he was going to accomplish—I'm pretty sure he would have gotten no salvation from the bus driver—but ultimately his desperate, foolish scamper would do him more harm than good.

Much to my delight!

He didn't get very far. While Melanie sat coolly stroking Eddie's inner thigh, her five cohorts gave pursuit to the panic-stricken Teddy. He was barely halfway up the aisle before one of the girls grabbed his ankle, sending Teddy sprawling to the floor of the bus. Within a second or two, four giggling girls were on top of him, pinning him down.

“Get off of me! Let me go!” he screamed.

Anna, now straddling Teddy’s backside, glanced over her shoulder toward Melanie. “What do you want us to do with him?”

“Take his pants off and bring him back here,” Melanie said, without even looking up. “I’m busy with little Eddie right now.”

I looked back and giggled. Poor Eddie was sitting stiff as a board, squirming nervously as Melanie’s fingers had delved into the leg opening of his underpants, probably close enough to touch his balls.

Meanwhile, halfway up the aisle, the five girls seemed quite delighted that they had the go-ahead from Melanie to strip off Teddy's trousers.

“Come on, let’s roll him over!” one of them giggled.

Teddy fought them tooth and nail, flailing about, but the girls were determined.

“You’re a feisty little guy, aren’t you?” Anna teased.

“Here—lift his head up and put him between my legs,” said Jenny, her voice calm and confident.

“Ooh, good idea!” Anna replied.

Jenny was tall and strong, with thick, muscular legs. She was wearing her Roosevelt-issue P.E. shorts that exposed an appreciable portion of her powerfully-built thighs. She stood over Teddy, spread her legs wide, and with help from the others, pulled him upright by the armpits. In one motion, she clamped her thighs around his head like a vice.

Teddy thrashed and grunted, prying at her legs with both hands, but it was hopeless.

“That’s why we call her Thunder Thighs,” Anna quipped, and they all laughed.

While Teddy knelt there, red-faced and furiously trying to pry himself free from the human vice, another girl knelt behind him, reaching under his stomach to unbuckle his belt. Teddy was so fixated on escaping Jenny's crushing grip on his head, he was momentarily oblivious to her giddy friend's earnest efforts to relieve him of his trousers.

His shoes and socks had already been yanked off in the chaos. It wasn’t until he felt the cool air on his thighs that he realized—with growing horror—that his pants were down to his knees.

“No! Stop it!” he shrieked, panicked.

Abandoning his efforts to escape Jenny’s leg-lock, he reached back desperately, trying to claw his pants back into place. But three girls were tugging in the opposite direction, giggling wildly, and Teddy didn’t stand a chance. In a matter of moments, he had the ignominious sensation of his pants being pulled free from his body, with the knowledge that his tighty-whities were on full display.

“Oh shit! Oh shit!” he cried, voice cracking with panic and shame.

For good measure—and to give us the added pleasure of a viewing bit more skin—Jenny reached down and yanked Teddy’s shirt up over his shoulder blades, all while keeping his head firmly clamped between her powerful thighs.

Teddy struggled, reached back, and managed to tug his shirt down again. Jenny immediately pulled it right back up—but this time, she hiked it over his neck and jammed the fabric into the space between her thighs, pinning it in place alongside his head. Teddy fumbled uselessly, trying to pull it free.

“Please! Let me go!” he whimpered.

Instead, things only got worse for Teddy—and a lot more comical. To the delighted squeals of the audience, Jenny began shuffling her feet backward—toward the front of the bus—dragging Teddy along by the neck. With no other option, he followed on his knees, gripping Jenny’s legs to ease the pressure on his neck.

Teddy’s shrieks were barely audible over the chorus of giggles and delighted whoops. And then, just when we thought it couldn’t get better, Anna made her move: She reached down and yanked Teddy’s underpants down his thighs.

“AAGH!” yelped Teddy, scrambling to pull them back up.

But the moment they were in place, Anna tugged them down again—triggering fresh howls of laughter. The two of them fell into a comical rhythm: Teddy pulling them up, Anna pulling them back down, again and again. Jenny just kept walking backward, calm and collected, as if leading a dog on a leash.

By the time they reached the front of the bus and pivoted for the return trip, the whole thing had evolved into a full-on comedy routine. Anna must’ve pulled down Teddy’s undies at least a dozen times, and each time he frantically yanked them back up like his life depended on it. The whole bus was in stitches—I was laughing so hard I could barely breathe, and judging by the snorts and squeals around me, I wasn’t alone.

Eventually, they arrived at the back of the bus, where Melanie was waiting. She lowered herself to her knees, so she was face-to-face with Teddy, who was still locked into the stranglehold of Jenny's thighs.

Melanie smiled. “Are you going to be a good boy now, Teddy?”

Before he could answer, Anna struck again—down went the underpants. Teddy gasped and reached back, frantically yanking them up once more.

"Please!" begged Teddy. "Make her stop!"

"Do you promise to do everything I say?" Melanie pressed, her eyes gleaming.

Once more, Anna tugged down his underpants—but this time, she didn’t let go. She held them firmly at his knees, so when Teddy reached back to pull them back up, his fingers found only empty air. It afforded us a wonderful, lingering view of his smooth, bare bottom. But it put Teddy in a state of panic. He squirmed helplessly, still trapped between Jenny’s unyielding thighs. His exposed tush wiggled about deliciously, much to our amusement.

"Oh! Please stop!"

"Do you promise, Teddy? Because if you don't, I'll have Anna just pull your tighty-whities right off."

"No! I mean yes! I promise! Please!"

Melanie gave Jenny a nod, and at last she loosened her grip, releasing the embattled Teddy. Before he even had a chance to react, she yanked his shirt the rest of the way off. Simultaneously, Anna let go of his underpants, and of course he instantly pulled them back up, that being his number one priority.

Teddy slowly rose to his feet, his hands clutched tightly over his crotch. His face was beet red. His hair was a mess. I mean, he looked like he'd been through the wringer.

"Okay, Teddy," Melanie said. "Let’s put our little agreement to the test. I want you to model those adorable tighty-whities for us. You'll be a captivating model, just like little Eddie was. The aisle will be your catwalk. Hands on your head now. Show us what you’ve got."

We watched eagerly while Teddy stood motionless, visibly weighing his options—which were, of course, nonexistent. After some time, he slowly raised his hands to his head.

Of course, I immediately checked him out. Up until that point, every physical attribute between Eddie and Teddy was remarkably similar, which is why everyone referred to them as "the twins." But now, a very distinct difference presented itself. While Eddie’s tighty-whities suggested a certain...deficiency, Teddy’s were telling a different story altogether. Indeed, the bulge in Teddy's underpants was surprisingly substantial, especially given his youngish looks and slender frame.

Nevertheless, Teddy’s mortification was written all over him as he stepped into the aisle and began his reluctant walk. His exposed state, along with his shamefaced little strut was just delicious.

When he returned to the back, Melanie clapped her hands gleefully. “Good boy, Teddy!” she beamed. She patted the seat beside Eddie. “Have a seat.”

Teddy obeyed, and I couldn't help myself from giggling at the sight of the two red-faced boys side by side in their tighty-whities, simmering with shame. It was almost too good.

"My, would you look at the tighty-whities twins. You boys look so cute!" Melanie cooed, lifting her phone with a wicked grin.

She aimed the camera at them. "Put your arms around each other for me."

The boys exchanged a mortified glance but obeyed, stiffly wrapping their arms around one another.

"Aww, that's just adorable!" Melanie chirped, snapping the photo. "Okay, now let’s make it even cuter—touch your heads together. Yes, just like that. Perfect." Another click.

She turned the phone toward Anna. "What do you think? Aren’t they the sweetest little tighty-whities cutie pies you’ve ever seen?"

"Ooh, yes," cooed Anna. Total cutie pies." She paused, tilting her head as if struck by sudden inspiration. "I’ll bet they’d look even cuter if they were naked."

The boys' eyes opened wide, and their jaws dropped at the suggestion.

As did mine!

"Hmm," said Melanie. "What an interesting idea. That never occurred to me," she lied.

Melanie then settled beside Teddy on the edge of the seat, resting a hand lightly on the inside of his thigh. She turned toward the frightened lads.

"What do you boys think?" she asked. "You’re already quite the sight in your tighty-whities...but wouldn’t you be just darling without them?"

"No!" said Teddy. "Please!"

Melanie’s hand inched higher along Teddy’s thigh, very close to his balls.

"Oh, but Teddy," she purred, "I’m actually quite impressed—with what I can see so far." She gave him a smile, then turned toward Eddie. "Especially compared to little Eddie here."

Eddie blushed brighter, but neither boy said a word. Their silence only seemed to encourage her.

"Wouldn’t it be fun to compare your penises—side by side?"

Both boys squirmed in their seats.

"I mean, I’ve already seen little Eddie’s goodies," she added. "It wouldn’t be fair if I didn’t see yours, would it?"

Without waiting for an answer, she leaned in and reached for the waistband of Teddy’s underpants with both hands. "Here—just a little peeky-weeky."

Teddy reacted instantly, swatting her hands away.

"No!" said Teddy. "I can't let you....do that. Please...."

"Jenny, would you hand me my backpack, please?" Melanie asked, her voice casual.

Jenny leaned back, grabbed the bag from the end of the seat, and passed it forward. Melanie set it in her lap and rummaged through it until she produced a large pair of scissors.

She turned to Teddy, holding the pointed end just inches from his face. "Teddy boy," she said. "It would be in your very best interest not to touch me again. Trust me on that."

I guess Teddy got the message, because he did not interfere when Melanie reached down and gathered the whole right portion of Teddy's tighty-whities in her fist and used the scissors to snip it free from Teddy's thigh.

"Oh! Oh no!" Teddy cried, clutching at what was left of his dignity. The ruined fabric still barely covered his privates—he made sure of that—but that would be a temporary situation.

Melanie, undeterred, reached across him and repeated the maneuver on the left side, snipping away. She then reached for the final piece—the strip of fabric nestled directly beneath his most sensitive parts. Her fingers brushed underneath, drawing a full-body flinch from him that was simply delicious to witness.

With a wicked little smile, Melanie took hold of the sagging cotton, now reduced to useless piece of cloth. She tugged it forward, then yanked it free. Teddy’s underpants—still technically intact, though clearly unwearable—were now dangling triumphantly from Melanie’s hand. She held them aloft for everyone to see, grinning widely. Then, with a casual flick of the wrist, she tossed them aside.

Much to my pleasure, Teddy was completely naked in the back of the bus!

Teddy, of course, was living a full-blown nightmare. He hunched forward as far as he could, knees pressed tightly together, hands clamped tightly over his genitals.

"Oh God! Oh! Please, give me my pants!" begged Teddy frantically.

Melanie remained unmoved. "You’ve been very difficult, Teddy," she said, as if scolding a disobedient child. "You’re not getting any of your clothes back until you start doing what you’re told without giving me any grief."

"Okay! I won't...I will! Please," he whimpered. "May I have my pants back? I promise to...to be good."

Melanie smiled, as though pleased by his submissiveness. "We’ll see how you behave. In the meantime, sit up straight—like little Eddie."

Teddy hesitated, then slowly lifted his shoulders and leaned back against the seat, still securing his modesty with his hands. His face was the color of a ripe tomato, his expression one of utter misery.

"Good boy, Teddy," said the smiling Melanie. "Now here's how it's going to work: Jenny is getting off at the stop before yours and little Eddie’s. She’ll be taking all of your clothes with her—including your shoes and socks."

Teddy looked horrified, and the rest of Melanie's explanation only slightly allayed his fears.

"She’ll leave your clothes on the bench at the stop. Hopefully they’ll still be there when you get off two blocks later and run back to fetch them."

She let that sink in, then continued. "Now, if you're a good boy the rest of the way—we should be there in just a few minutes—then I most likely won't make you get off the bus naked." She leaned in slightly. "I have something for you to wear."

She then turned to Eddie, her grin returning. "And this is where you come in, little Eddie."

Eddie, though clearly mortified to be sitting there in nothing but his tighty-whities, was probably at least a little grateful that he hadn't been the center of attention. That, however, was about to change.

"I’m going to give you the chance to go home wearing your pants, shirt, shoes, and socks," Melanie announced. "That option is entirely up to you. Would you like that, Eddie?"

Eddie nodded quickly, a flicker of hope flashing across his face.

"Good," said Melanie with a satisfied smile. "Now here’s your chance to show what a good friend you are to Teddy."

Both boys stared at her, visibly perplexed. Personally, I was quite intrigued.

"You see," she went on, "you’ve been a good boy, Eddie. And as long as that continues, you’ll be rewarded—with your clothing. But Teddy hasn't been such a good boy, so he's going to have to leave the bus either naked or in a pair of tighty-whities."

Their eyes dropped in unison to Teddy's tighty-whities, which had been shorn to the point of being unwearable. I could see where this was going, and I was tickled pink.

Maybe their minds were clouded by the humiliation they were undergoing, but both boys looked thoroughly bewildered.

"Okay, I guess I need to spell it out for you," Melanie said with a laugh. "Eddie, your friend is going to have to get off this bus completely naked—unless you're willing to let him wear your tighty-whities."

Eddie's jaw dropped. Eddie looked at Teddy. Teddy looked at Eddie. It was an exquisite moment.

"So," Melanie pressed, her grin widening, "what’s it gonna be, Eddie? How good of a friend are you? Are you going to help him out...or will he have to run naked in the street?" She leaned in, eyes gleaming. "His fate is in your hands."

"Eddie, please," Teddy begged, his voice trembling. "Don’t make me do that!"

It was the first time the two boys had spoken to each other since their ordeal began. It was entertaining, and probably exactly what Melanie had hoped for. She said nothing, choosing instead to watch, as the two unfortunates tried to negotiate their shared humiliation.

"I don't...I don't know," Eddie stammered. His arms were tight around his waist, his eyes fixed on the floor. "I don't want to....to be nak....I don't want to take these off."

This is awesome!

"Look at me, Eddie!" cried Teddy. "I'm already there!" responded Teddy. "I need to put...to put something on!"

"I know, I..." Eddie’s voice broke. "Oh God, I'm sorry, Teddy...I just...I don't know what to do!"

"Eddie, I’m begging you. Please! I’m naked! I can’t go out there like this!"

There was an extended standstill while Eddie sat paralyzed, and Teddy stared at him, desperate and exposed.

Then Melanie broke the silence. "Alright," she said. "It’s decision time, Eddie. Are you going to make your friend walk off the bus naked—or are you going to let him wear your tighty-whities?" She leaned forward, voice soft but commanding. "If you’re going to help him, you need to do it right now."

Eddie looked out the window for a few moments, took a deep breath and then—to everyone’s amazement—he slowly reached for the waistband of his underpants.

"He's gonna do it!" squealed one of the girls as Eddie began to slide them down.

Melanie’s eyes sparkled. "Oh, what a good friend you have, Teddy," she said. "You're such a lucky boy."

Eddie indeed stripped himself of his underpants to gallantly save his friend from furthering his humiliation. With one hand over his privates, he held out his tighty-whities for Teddy. But just as Teddy was about to accept the offering, the devious Melanie snatched them from Eddie's grasp.

"Teddy will get these when we reach his stop," she said with a sly smile.

Eddie blinked. "Can I have my clothes now, please?" he asked anxiously.

"Oh, sure, little Eddie," Melanie replied. "As soon as we get to your stop."

And just like that, there were two naked, red-faced, squirming boys sitting side by side in the back of the bus, and I couldn't have been more titillated.

We reached the boys' penultimate stop and Jenny, true to the plan, had Teddy's clothes gathered in her arms. She gave him a friendly little smile as she stepped off the bus.

Teddy twisted in his seat, craning to watch her through the window as she strolled to the bench and laid the clothes out, piece by piece, while the bus began to pull away.

"Don’t worry," Melanie cooed. "I know it will be awfully embarrassing, but you'll only have to run a couple of blocks in Eddie's tighty-whities."

At the time, I felt a twinge of disappointment. Just two blocks left? It had all been so perfect—I wasn’t ready for it to end.

But as luck would have it (terrible luck for the boys!), the bus had come to a standstill. I looked out the front window and could see that we were in a construction zone, and we were at the mercy of the guy directing traffic. We started creeping along, but ever so slowly.

"Oh goody!" chirped Melanie. "This gives us a little more time to get acquainted."

Judging by the looks on their faces, neither Eddie nor Teddy had the slightest interest in “getting better acquainted” with their grinning antagonist—or more accurately, letting her get more acquainted with them.

"How about a little show and tell?" Melanie offered. "I'm sure we'd all love to compare your bits." The boys squirmed ever more uneasily in their seats. "Come on, my naked little twins. Stand up."

Not surprisingly, the boys hesitated, and Melanie found a way to motivate them. "Anna, would you mind opening the window for me? I’d like to toss their clothes out onto the road."

I giggled as both boys stood up like a shot, their faces portraying sheer panic.

Melanie gave them an approving nod. "Much better." She looked down at their privates, which were concealed securely by their hands. Much to my pleasure, that would soon change.

"It's time, boys. You're going to show us your bits, and you're going to do it now. Teddy, you go first. Put your hands on your head and keep them there."

The agonized Teddy slowly, resignedly raised his hands above his head.

Of course, we all stared. And judging by the reactions of the other spectators, I wasn’t the only one surprised by what I saw. Teddy's penis was even larger than I expected, and his balls were a decent size, too. Plus, he had sprouted pubic hair, which was considerably darker than the golden-colored hair on his head.

"Wow, Teddy," remarked Melanie. "I'm impressed. Your cock is almost like a man's."

She smiled at the quivering boy beside him. “What do you think, Eddie?”

Eddie, though he wasn't blatantly staring at Teddy's dick like the rest of us were, probably copped a peek out of the corner of his eye. I mean, he must have—it's human nature. And when he did, it certainly couldn't have given him any comfort, knowing that he would soon have to expose his own very private parts—and now knowing that he didn’t come close to measuring up.

"I asked you a question, Eddie," persisted Melanie.

"I...I don't know," he answered nervously. He was shifting his weight from foot to foot like he needed to pee, clearly dreading his looming exposure.

"Well, take a good look, and tell me what you think," ordered Melanie.

Eddie turned his head reluctantly, stole a glance at Teddy’s privates, then quickly turned away.

“Well?” Melanie pressed.

"It's...I don't know...it's...fine."

The chorus of laughter that followed was explosive.

"Fine? It's fine?" cackled Melanie. “Oh, Eddie, you really are precious.” Then she nodded at his hands. “Okay, now it's your turn. Hands on your head—let’s see what you’ve got.”

Melanie had a smirk on her face when she said that, because—as we know from the last chapter—she had already peeked inside Eddie’s tighty-whities. She knew exactly what he had. Or rather, what he didn’t.

A hush fell over the bus as everyone watched Eddie curl his toes and squeeze his eyes shut. For a few torturous seconds, he just stood there, motionless. Then he raised his hands above his head.

The laughter that erupted then was the loudest yet—sharp and relentless. Poor Eddie stood trembling and completely exposed, eyes still clenched shut.

The cause of the laughter, of course, had everything to do with Eddie's tiny penis, together with his diminutive balls and total hairlessness. It certainly didn't help his cause that he was standing next to his well-endowed friend. I'm sure we were all looking back and forth at them, and the contrast was quite striking.

“Oh, little Eddie,” Melanie said, giggling along with the rest of us. “You poor little boy!”

To this day, I don’t know how Eddie managed to keep his hands while standing there so exposed. I guess the metaphorical carrot at the end of the stick—the promised return of his clothes—outweighed the excruciating humiliation that he was going through at that moment.

Fortunately for the boys, the bus had been creeping forward, and just a couple minutes after Eddie (make that little Eddie, lol) revealed all, we finally reached their stop.

It also happened to be the stop for Melanie and the rest of her crew. “Time to go, boys,” she chirped.

Both boys dropped their hands to their crotches in perfect sync.

Melanie clutched Eddie’s bundle of clothes, including the tighty-whities that were earmarked for Teddy. They looked at her anxiously and hopefully, but she wasn't quite forthcoming with the goods.

“I said you can have these at the stop,” she said. “The stop is outside.”

Eddie and Teddy looked at each other miserably. There was a certain amount of commiseration perceptible with their expressions, which I thought was kind of cute.

The back door of the bus swung open. Melanie descended first, followed by her giggling friends—and then, hesitantly, the naked boys.

As soon as they exited, everyone on the left side of the bus collectively scrambled to the right, faces pressed to the windows for the best view. I watched with amusement and stimulation—the boys' backs were to us, but I did enjoy looking at their cute little tushies—as they waited expectantly next to Melanie. It was reminiscent of a couple of doggies waiting for their treats.

Melanie was in no rush to indulge them. First, she handed Eddie a shoe. Then a sock. Then another shoe. Then the other sock. None of those articles of clothing seemed to appease the anxious boy.

Eddie’s eyes were wild with impatience, and Teddy was looking around nervously while humorously (for us) jumping up and down.

Finally, Eddie received his pants and shirt. He slipped them on in record time, skipped the socks and shoes entirely, and darted away from the scene as quickly as he could.

He disappeared around the corner, and my focus immediately turned to the still-naked Teddy. Melanie teasingly dangled Eddie’s tighty-whities in front of him, just out of reach. Then, with a laugh, she turned and started walking away.

Teddy gasped, and frantically followed her for a few steps—and at last, she handed them over.

A moment later, much to my amusement, Teddy was scampering awkwardly down the street, a bit underdressed in little Eddie's tighty-whities.

For the rest of their high school life, they were known as "The Tighty-Whities Twins," and the story of their misadventures on the bus will live forever in Roosevelt lore.
Last edited by Blondie on Sun Jul 20, 2025 7:26 am, edited 1 time in total.
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Re: Underpants Memoirs

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My favourite two chapters of this story! :D
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Underpants Memoirs, Chapter 9

Post by Blondie »

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Chapter 9: The Misadventures of Blondie

At the school like no other, there was one particular student who was humiliated to a degree like no other. I promised in my intro that I would devote a chapter to Blondie's travails, and I must say that his misfortunes—calamities is probably a more appropriate word—certainly warrant its own chapter.

Blondie and I were in the same graduating class, which meant I had front-row seats to a fair number of his finest (read: most mortifying) moments. Now, most Roosevelt victims see their torment taper off after freshman year, but Blondie was the rare exception. The poor guy was still getting pantsed as a senior. A senior! I know, because I was lucky enough to be there for one of them.

All told, I witnessed Blondie getting stripped—one way or another—about half a dozen times. I know there were more; the stories made the rounds, and I definitely missed a few. In this chapter, I’ll stick mainly to the ones I saw firsthand.

Some of these moments have already been documented elsewhere—either by Blondie himself (on the Web, under Roosevelt Humiliations) or by his most relentless tormentor, a former student named Felicity (The Felicity Chronicles). I won’t rehash those in full, but I’ll briefly touch on them to offer an outsider’s perspective.

That said, there’s at least one unforgettable incident I’ve never seen described anywhere—and believe me, I’ll be giving that one the attention it so richly deserves.

Let’s begin, in chronological order, with a few of Blondie’s finest—and most humiliating—moments.

* * * * *

Freshman Year

As fate would have it, Blondie and I shared the same homeroom. And to make that lucky circumstance even sweeter, our homeroom teacher was none other than Miss Farnsworth—yes, the Miss Farnsworth—who, as readers of these memoirs already know, was quite fond of delving out the occasional humiliation to one of her unfortunate students when the opportunity arose.

It had started out as a perfectly ordinary October morning. That abruptly changed to extraordinary .

I was already settled at my desk in homeroom when a red-faced, youngish-looking boy entered the room—clad in nothing but a white tee shirt and a pair of tighty-whities. Apparently, a few seniors had taken it upon themselves to “welcome” him to Roosevelt by stripping him down to his down to his underwear. They made him show up to homeroom like that, probably with the threat of taking it even further if he didn't do so.

The atmosphere in the room suddenly changed from boredom to excitement. I remember grinning from ear to ear and feeling the titillation that I get when I witness a boy's humiliation.

And it was about to get better.

Miss Farnsworth walked in and immediately sensed the charged atmosphere among her students. It didn’t take her long to figure out why—Blondie was seated front and center in the first row.

A smile crossed her lips as she looked Blondie up and down. “Stand up,” she said.

Blondie hesitated, then obeyed.

"You have very pretty legs," she said, and we all laughed.

It was true. Blondie’s legs were slender, long, and almost elegant—sleek and smooth enough to belong on a swimsuit model, not a teenage boy. They barely had any hair, if any at all. “Pretty” was definitely the perfect word. Honestly, I wished I had legs like that. I’m pretty sure Blondie didn’t share that sentiment. :)

It was true. Blondie’s legs were slender, long, and a little on the elegant side—sleek and smooth like they belonged on a swimsuit model, not a boy. They didn’t seem to have much hair at all, if any. “Pretty” really was the perfect word. Honestly, I wished I had legs like that. I'm pretty sure Blondie didn't feel the same way.

Then Miss Farnsworth glanced out the window. We all followed her gaze, and there they were—Blondie’s corduroys, hoisted up the flagpole, comically flapping in the breeze.

"Those must belong to you," said Miss Farnsworth, stating the obvious.

Blondie muttered something under his breath—something that sounded an awful lot like “fucking genius.” He thought it was under his breath, but he was mistaken. And much to my delight, it gave the depraved teacher a reason to further Blondie's humiliation.

"Take off your shirt," she said, and it was music to my ears.

I don’t think Blondie realized she was serious—he didn’t yet know Miss Farnsworth’s reputation. Neither did I, at that point. But I can tell you this: I was dearly hoping she meant it.

Well, she did.

“Unless you’d prefer I take you over my knee and spank your bare bottom in front of the class,” she added.

A rush of pleasure shot through me when she said that, and the reasons were twofold. First, the image of her delivering a bare-assed spanking was outrageously delicious. And second, it became crystal clear she had no intention of stopping there. She was going to strip the terrified freshman even further—and I’m pretty sure Blondie realized it too.

Lo and behold, in a matter of moments she was tucking his tee shirt into her desk drawer, and Blondie was standing among us wearing nothing but his tighty-whities.

My juices were flowing as I watched the mortified student slink back toward his seat—only for Miss Farnsworth to stop him cold. “You’ll remain standing for the rest of roll call,” she said. He hesitated, then reluctantly rose. “And face the class, please.”

He turned slowly to face us. Of course, his face was tomato red, and the look on it was exactly what you'd expect in a moment like this: pure misery. His eyes were glued to the floor, and his hands moved instinctively to shield his groin.

“Hands at your sides,” Miss Farnsworth snapped.

At first he didn’t move, but he eventually obeyed. And when he did, of course I immediately checked him out. And what I saw made it all the better.

I giggled (along with many others), since there was not much to check out. There was a small bump from his penis, and his balls didn't fill out the material in any way whatsoever. This only added to my enjoyment, because I knew Blondie's humiliation had to be through the roof.

Eventually, Miss Farnsworth dismissed him to retrieve his pants. But when he asked—almost whimpered—for his shirt, a smirk formed on the corner of her lips. “You may have it when you return with your trousers,” she said.

And off he went, forced to traverse the hallway and venture outside in his tighty-whities. I could hear his bare feet slapping the floor as he made the mad dash down hallway. The mental pictures of Blondie in his tighty-whities that morning still bring a smile to my face.

* * * * *

Sophomore Year

Though I subsequently witnessed several strippings during my freshman year, none of them involved Blondie. I had heard of several instances involving him—one of them in which he was forced to strip naked in the darkened auditorium during the school play! But alas, I wasn’t lucky enough to be there for any of those legendary moments.

However, there was one Blondie episode in the latter half of sophomore year that I did witness firsthand. And it was a doozy.

(Note: Blondie devoted a whole chapter to this scene in his aforementioned Roosevelt Humiliations.)

Once again, the scene was our ever-eventful homeroom. And of course, Miss Farnsworth was involved.

But this particular incident wouldn’t have happened at all if not for a girl named Brenda. Over the course of our first two years, Brenda—and a few others, including Blondie’s own sister Becky—had gained control over Blondie, and sadistically used that control to humiliate him on several occasions. Blondie, in his foolishness, once attempted to strike back.

His grand plan? He showed up early to homeroom and wrote, in enormous chalk letters on the board: “BRENDA HAS TINY LITTLE TITTIES.”

It was true—Brenda was not well-endowed in the chest department—and when she walked in, everyone giggled at her. When she saw the reason why, she ran up and erased the offensive text. When she walked back to her seat, I could see that her face was bright red.

A few days later, Blondie got cocky. He tried the same maneuver—and this time, Brenda caught him in the act.

From what I heard later—delivered in detail by Brenda herself—she made him drop his pants on the spot. Then, using a pair of scissors, she cut off his underwear. All of it. Then she tied a bright orange piece of yarn around his his dick and balls. When he pulled his pants back up, she used another length of yarn to tie his wrists behind his back.

Then she reached through the fly of his pants, grabbed hold of the yarn, and began leading him down the hallway like a naughty pet. Right out into the courtyard.

She paraded him around the courtyard, in front of the now famous (infamous?) Roosevelt statue. And then, after abundant teasing in front of many delighted eyewitnesses, she yanked his pants down to his ankles, revealing his little bits to all.

God, I wish I’d been there. But what happened after—when they returned to homeroom—more than made up for my missed opportunity.

I was idly scrolling through my phone at my desk when a grinning Brenda walked in. She was pulling on the length of yarn, leading a bare-chested Blondie literally by the balls, as the yarn extended from inside the open fly of his pants. He followed behind her, face burning.

She proceeded to entertain us by parading her humiliated pet back and forth across the front of the room, much to our amusement. His face was beet red, his eyes glued to the floor.

Then she let him put on his shirt and tuck the yarn in his pants before zipping up. She whispered something into his ear and sat down.

The beleaguered Blondie cringed, then reluctantly trudged to the board, picked up the chalk and wrote in giant letters, "BLONDIE HAS A TEENSY WEENSY HAIRLESS LITTLE PEE-PEE."

When he turned and walked back to his seat, the laughter was deafening. His face was crimson, and my delight was off the charts.

And just when it seemed like Blondie couldn’t possibly sink any lower, the diabolical Miss Farnsworth walked in. She immediately saw what was written on her board. She looked at Blondie and smiled.

I knew there would be no stopping her. I think I licked my lips in anticipation.

"Mr. Haggerty," she said. "Would you care to explain who is responsible for this?"

After hesitating, Blondie admitted it was him.

"Are you familiar with the concept of shame clothing?" she asked him.

I sat up straighter in my chair, eager for events to unfold. Then I nearly choked on my own saliva when she reached into her desk and pulled out a black, lacy bra.

"Would you please remove your shirt and come up here?" she said.

Blondie was soon bare-chested again. Counting his topless entrance with Brenda earlier, this made the third time he’d been stripped from the waist up in homeroom—which, for the record, is exactly three more times than anyone else. Poor, poor Blondie. I loved it!

She turned the miserable boy to face us and went to work with her “shame clothing.” In moments, the bra was snugly fastened around his chest, and the result was absolutely comical. When she quipped that she kept the A-cup handy for her flat-chested girls, the room exploded with laughter—and Blondie’s face turned scarlet.

But Miss Farnsworth wasn’t done. She looked him up and down and appeared deep in thought. I couldn't wait to see what she had in mind.

“As I recall,” she said, “the last time I had to discipline you, you weren't wearing pants, and you were showing off some very pretty legs. I think, since you’re already standing here on display in such a pretty bra, it would be quite appropriate—and entertaining, I might add—for you to put your pretty legs on display, also.”

I was getting excited, thinking he'd have to expose his tighty-whities again. I was not aware at the time that Brenda had cut off his underpants earlier that morning.

He whispered something to Miss Farnsworth, who smiled devilishly and said, "Why aren't you wearing any underpants?"

I gasped, and remember being disappointed, because I thought for sure that under the circumstances she wouldn't make him drop his pants.

But I had badly underestimated Miss Farnsworth’s appetite for humiliation. She was intent on doing just that—probably even more so, since he was naked underneath. She reached for his belt (Blondie had turned around to face her, imploring her to let him keep his pants up). He instinctively grabbed her wrists. That earned him a sharp reprimand, and he quickly let go.

Without hesitation, Miss Farnsworth unbuckled his belt, yanked open the front of his pants, and tugged them down to his ankles. A collective gasp swept through the classroom, followed by gleeful laughter. I, for one, drank in the very pleasant sight of his cute little bare ass—and yes, his pretty legs.

To compound Blondie's ignominious plight, there was the matter of the bright orange yarn Brenda had so mischievously tied earlier—still dangling down from his privates. Miss Farnsworth shook her head, called him a pervert, and told him to put his hands (which were clasped over his genitals) on his hips. Again he begged, but she was not to be denied.

When he pulled his hands away she grinned and said, "You poor dear," which drew considerable laughter.

Then she made him read out loud what was on the board. "Blondie has a teensy weensy hairless little pee-pee," he said with a cracking voice.

"Indeed you do," she said, and we all laughed harder.

I dearly wanted to see for myself—I hadn't yet had the opportunity to see his little dick—but I doubted I’d be that lucky. Once again, I underestimated the wickedness of Miss Farnsworth.

She told him to turn around and face his classmates. After considerable hemming and hawing, he did so, and I have to say that I was basking in the sight, and in Blondie's humiliation. I savored every mortifying second.

Indeed, the writing on the board was accurate. He had a little pee-pee, and there was not a hair to be found. Now, even if he had a bigger dick with hair, his humiliation would still have been quite profound. But for a 15-year-old boy to stand there like that with his hairless little bits on full display? Oh, my goodness!

And as if that weren’t enough, Miss Farnsworth added the final flourish. Still wearing the bra, pants around his ankles, Blondie was made to sing I Feel Pretty from West Side Story.

Blondie's humiliation was complete, and I had another wonderful memory to add to my ever-growing collection of memories.

* * * * *

Senior Year

If Blondie had any luck at all, the progression into his senior year would have marked the end of his strippings and humiliations. His usual tormentors—though I heard they toyed with him a bit over the summer—had pretty much exhausted their ways of humiliating the boy, and truth be told—I got this from Brenda—after three years of tormenting Blondie, it just wasn't as exciting for them as it used to be.

But much to Blondie's misfortune, there was a new kid on the block. Her name was Felicity, and she was a force to be reckoned with. She was the younger sister of one of Blondie’s original tormentors, and she’d apparently been invited to one of his “episodes” the summer before. Apparently she enjoyed herself quite a bit. Her appetite for humiliation was whetted, and from that moment on, she was hooked.

Felicity arrived at Roosevelt as a freshman that fall, the same time Blondie was limping into his senior year. She became quite the terror (with the help of a few friends), and it wasn't long before she developed a circle of victims. All but one of them were freshmen—a poor kid she called Johnny Boy was a common patsy—and, you guessed it, the exception would be the one and only Blondie. Evidently she possessed some incriminating, very embarrassing video footage from her experience with Blondie that summer night. And much to Blondie's bad fortune, though Felicity had plenty of freshmen students under her thumb, Blondie seemed to be her favorite target.

I was sitting in homeroom before it started when Brenda started chatting me up. She informed me of Blondie's experience that occurred on the previous day. The longer she spoke, the more wide-eyed and agape I became. Evidently, just the day before, Felicity had cornered Blondie at his locker—and before all was said and done, he was stark naked.

And here's the kicker: Before she let him get dressed, she gave him a list of instructions. She told him that when he got home that day he was to shave his body completely hairless, and he was to keep it that way from that day forward. I guess he had finally grown pubic hair, and according to Brenda, Felicity took hold of a tuft of it and said, "This has to go, too. I like my boys to be smooth all over." I mean, couldn't you just die?

Anyway, legs, arms, underarms—everything! Plus, Blondie was now required to wear short shorts—very short, Felicity insisted, warning that if the hems got anywhere near mid-thigh, they were coming off. He also had to wear tight, short-sleeved tees to show off his new silky-smooth arms. No socks—“so people can admire those pretty legs.” And my personal favorite: He had to go back to wearing tighty-whities. Apparently he’d made the switch to boxers at some point, but Felicity decreed that since his body wasn’t “mature enough” to warrant such grown-up underwear, he’d need to stick with the kind little boys wear. She said that he'll look like a 10-year-old boy down there with his hairless little bits, so tighty-whities are much more appropriate.

Don't you just love it? Oh, I'm so sorry I missed that scene!

Blondie hadn’t arrived yet, and I was starting to watch the door with rising anticipation. "Do you think he will do it? Or did it?" I asked Brenda.

Brenda smirked. “Oh, I’m thinking yes. If you’d seen him with Felicity yesterday, you’d know how terrified he is of her. As he should be.” She giggled.

"I can't wait to see. And I so wish I had been there yesterday."

“Oh, you would’ve loved it,” Brenda said. "After telling him what he had to do, she made him repeat everything back to her before she’d let him get dressed.”

“Oh my goodness!”

“Yup. She goes, ‘Tell me why you’re not allowed to wear boxer shorts.’ And he says, ‘Because I haven’t earned it?’ It was so funny! So she said, 'Yes, and tell me why you haven't earned it. He stammered like crazy and finally said, ‘Because I haven’t matured enough?’”

I gasped, grinning. "Oh, my goodness!" I said again.

“I know, right? And then she goes, ‘In what way have you not matured?’ And he couldn’t even answer, so she goes, ‘Is it because you have little boy bits?’ And the poor thing just mumbled, ‘Yes.’ So of course, she made him say it.”

“He said it? Out loud?”

“Oh, yeah. He goes, ‘I have little boy bits.’ And then Felicity asks, ‘After tonight, what embarrassing feature will your little boy bits have?’ He whispers, ‘They’ll have no hair.’”

I covered my mouth, laughing. "Oh my God, this is too much!"

“And Felicity goes, ‘That’s right! You’ll have bald little boy bits!’”

"Oh, that's hilarious!" I said.

"And then..."

Right then, the star of our conversation entered the room. He was moving fast, clearly hoping to get to his seat unnoticed—but I was able to take in his attire: very short shorts, a short, tight tee shirt—there was skin exposed above his shorts—and an extremely red face, which turned even redder when he heard a wolf whistle coming from the back of the room.

I scrutinized his legs and arms, and sure enough, there was not a hair to be found. I was pretty sure there was also no hair anywhere inside his shorts, and that he was almost certainly wearing his tighty-whities.

A few days later I would have the distinct pleasure of seeing for myself.

* * * * *

After that morning, I’ll admit—I became a bit of a stalker. Any chance I had to follow Blondie around, I took it. I was hoping to catch another of Felicity’s delicious little encounters with him. And one afternoon, just as the lunch period began, I got my wish.

By the way—this is the event I mentioned earlier, the one I’ve never seen described anywhere else. I was so lucky to witness it firsthand—and as you'll see, actually play a part in it!

Blondie was walking alone down the hallway when she appeared—seemingly out of nowhere. She greeted him cheerfully, and I could tell she was enjoying the frightened look on his face every bit as much as I was.

She took his arm. He resisted. But of course, Felicity would get her way. She steered him straight into the girls’ bathroom.

Naturally, I had to follow. I wasn’t about to miss out on whatever Felicity had in mind for him. And I had a feeling there would at least be a tighty-whities sighting.

The bathroom was fairly spacious, and there were already about a dozen girls inside—more trickling in behind me. At first, a few gasped at the sight of a boy entering, but that quickly gave way to amusement when they saw his smooth legs, his sheepish expression, and the freshman girl leading him like she owned him.

Felicity stopped near the sinks, still holding his arm, then turned him to face the crowd. “You shouldn’t have resisted, Blondie,” she said matter-of-factly. "You'll have to be punished now."

“Please,” he stammered, “I...I didn't want to go in the...it's the girls’ bathroom."

“Yes it is,” Felicity agreed. "And you have such pretty, girly legs," she continued, playing to the growing crowd. "So you should feel right at home." She glanced at his shorts. “All I wanted to do was check and make sure you were wearing the tighty-whities like I told you to.”

The sound of giggling girls echoed throughout the room, and the sense of anticipation was palpable. I, for one, could feel my pulse quickening, as I eagerly took in the unfolding scene.

“I am wearing them!” he blurted. “Here—look.”

He hooked his fingers into the waistband of his shorts and yanked upward, revealing what definitely looked like the waist band of a pair of tighty-whities. But I had a feeling that wouldn’t be enough for her. And, thankfully, I was right.

"Oh, we need to have a better look than that," Felicity said as she reached for the snap at the top of his shorts.

"Please, Fel...please, not here...please, can I...can I show you in private?" begged Blondie. His eyes darted around nervously—and for a moment, they locked on mine, which I really enjoyed. I gave him my best coquettish smile.

Felicity wasn’t moved. "I don't think so. You lost your chance at privacy when you tried to defy me,” she said calmly as she pulled down his zipper.

Blondie didn’t dare resist when Felicity stepped behind him—positioning herself, no doubt, to give us all a perfect view (much to my delight!)—and took hold of both sides of his shorts.

“Are you ready to show everyone your tighty-whities?” she teased, pausing for dramatic effect.

"Please...no..." he whispered.

I loved how he pleaded for mercy. I mean, he had to know that Felicity was going to expose his tighty-whities to us. But that didn't stop him from begging, which demonstrated how desperate he was. That's why, for me, his begging only added to my enjoyment of his ongoing humiliation.

Felicity drew things out even longer, letting go of his shorts and lifting his shirt instead, baring his stomach. She held it up to his chest and smiled.

"Now we'll get a nice, unobstructed view of your little tighty-whities when your shorts come down," she said.

I was really enjoying her commentary. She had a gift for staging the moment—setting up the scene just right for maximum humiliation. And the way she exposed his belly? That was a nice touch. The newly bared skin was not only tantalizing—it served as the perfect bit of foreshadowing for what we all knew was coming.

Again she put her hands on the tops of his shorts...and again she let go. This time she turned to the rest of us.

"Would anyone like to do the honors?" she asked.

My hand shot up before I even realized I’d moved it. “I’ll do it!”

Felicity turned, smiling, and gestured with an open palm. “He’s all yours.”

I was very excited about my good fortune, and I wanted to make the most of it. I stepped in front of Blondie, made eye contact, smiled, and stuck out my hand. Though we had been in the same homeroom all three years, we'd never really spoken, mainly because Blondie was a bit on the shy side.

“Hi Blondie,” I said. “I’m Michelle.”

“Hi, Blondie,” I said. “I’m Michelle.”

Blondie miserably reciprocated with a half-hearted handshake. Just for the hell of it, I leaned in and kissed his profusely blushing cheek. I still remember how warm his skin felt against my lips.

I crouched down, took one last look at his anxious expression, and said, “Showtime.” Then, without hesitation, I grasped his waistband and tugged his shorts down to his ankles in one smooth, leisurely motion.

Cheers erupted around me, but I barely heard them. My attention was fixed on the sight before me: pale upper thighs, smooth and hairless...and, of course, the pristine white cotton of his tighty-whities, clinging to him snugly. I suppose I got a small taste of what Felicity must feel—the humiliation that I had generated for the poor boy was intoxicating. It was an exquisite moment for me, and I still savor it to this day.

I stepped back to survey the wonderful scene, and to let the expert take over.

“Thank you, Michelle,” said Felicity. “That was well done.”

She turned to Blondie, now bent slightly forward, hands desperately clasped over his front. I was enjoying his body language, and his shame.

Felicity crouched at his feet and tapped his leg. “Step out, please.” He did, and she removed his shorts, then his shoes. “I want you barefoot while I strip you to your tighty-whities,” she said.

She then stood behind him and took hold of his shirt tail. "Arms up, please. Tighty-whities only for you." Blondie hesitated, was about to say something, but then he just submitted. “Higher. Hold them up nice and high.” Blondie complied.

Naturally, our eyes all dropped to his crotch. There wasn’t much to see. Giggle.

Felicity took her time pulling off his shirt, especially once she revealed his smooth underarms, which I found very intriguing. I remember thinking how humiliating it must have been for him, a 17-year-old boy forced to keep his legs and underarms all smooth at a 13-year-old girl's behest. Then to have to expose that to us, all stretched out like that—in the girls’ bathroom, no less—gosh, I can only try to imagine how mortified he was. Even with that in mind, I was dearly hoping for more. :D

"I wonder if he has any hair inside those underpants?" giggled one of the onlookers.

"I doubt it," said another, and everyone laughed.

The shirt finally came off, and Blondie’s hands flew back to his groin. That wouldn’t last.

“Blondie,” Felicity said, “we can’t get the full effect of your tighty-whities presentation when you’re covering your little bits.” He stayed frozen. “Let’s keep your hands on your head from now on and away from your little boy bits. I think everyone would find that very pleasing.”

Blondie slowly, miserably, raised his hands to his head. Felicity was right: I found that very pleasing. :lol:

“That’s my good boy,” Felicity purred, walking a slow circle around him. She trailed her fingers up and down his sides as she passed, clearly enjoying herself. "You look so delectable." When she reached the front again, she placed her hands on his hips. "Do you know how you can become even more delectable?" she asked.

Oh, be still my heart! Tell me this is going where I hope it is going!

Blondie must have been thinking what I was thinking also, because his eyes grew as big as saucers.

"Oh, I think you do," said Felicity. "Can you tell me, Blondie?" She put her hands on his hips. "Can you tell me how we can make you even more delectable?"

"Please, I...I don't know," he stammered.

"But I think you do, sweetie.” She slid her hands into the back of his underwear and gently felt up his bum. "And I want you to tell me."

Blondie was between the proverbial rock and a hard place. He knew exactly what Felicity wanted him to say, and he didn't want to even say it, much less do it. But if he didn't answer—or, to take it a step further, answer correctly—then somehow she would make matters even worse for him.

Is that even possible?

"I…by...by pulling down my underpants?" Blondie finally squeaked out, his voice barely above a whisper.

A chorus of delighted giggles erupted around the room.

"Good, Blondie!" exclaimed Felicity as she took her hands out of his tighty-whities and clapped her hands together with glee. “You’re definitely on the right track. But see, there are degrees of delectability.”

She paced slowly in front of him as she spoke, adding to the drama. “For instance,” she continued, “right now, standing here in front of all these girls—so embarrassed, so exposed in your tighty-whities, with those pretty, hairless legs on display—I’d say your delectability level is a solid eight on a scale from one to ten.”

Blondie looked like he might become ill.

“Now...if we were to do what you just suggested—and thank you so much for that—if your little underpants were pulled down to your knees? Mmm, I'd put your delectability level at a solid nine. And it would answer a burning question one of your admirers asked earlier—namely, if you have any hair on your little bits."

The girls giggled again, and I felt my cheeks flush with anticipation.

But!” Felicity held up a finger, theatrically. “Let’s say we took it even further. We don’t stop at your knees—we pull your tighty-whities aaaall the way down those silky-smooth legs, and right off your feet.” She paused, locking eyes with Blondie. He looked absolutely miserable, and I don't think I could have been more excited. “If we did that, Blondie...what would you be?”

"Um...um..."

“Come on,” she coaxed. “Say it. What would you be?”

“A...a ten?” he offered, timidly.

She laughed. “Well, yes. Your delectability level would be a ten. But you wouldn’t be wearing any clothes. So you’d be...?”

“N-naked?” he whispered.

Oh, I loved it!

“Yes!” Felicity beamed. "You'd be naked! And yes, your level of delectability would be a perfect ten!"

She paused to let that sink in, then continued. “Tell you what,” she said, spinning to face the audience. “Let’s take a vote.”

She held up her hand. “Simple show of hands. Who here would like Blondie to keep his tighty-whities on?”

Predictably, no hands went up.

“Anyone? No? Okay, then. Who would like to see his tighty-whities pulled down to his knees?”

One hand shot up quickly, but she then withdrew it when she realized there was another, more enticing option.

“And finally…” Felicity’s voice rose with dramatic flair. “Who would like to see Blondie’s tighty-whities removed completely—in which case he’d be...?” She extended her palm toward us.

“NAKED!” we shouted in unison, hands thrust high into the air.

The atmosphere was electric. Felicity was putting on an amazing performance, and it was a stimulating buildup to what was becoming a foregone conclusion. I can tell you, she really had me worked up.

“Well, I guess the people have spoken,” Felicity said, turning back to Blondie. “And apparently, they want you to be naked.” She paused and smiled at the hapless Blondie. "Are you ready to be naked?"

“No!” he cried out. Please, I'm begging you! Don't...don't do this! Not here!"

I was amazed—and more than a little turned on—that he was still begging. Surely he knew it was hopeless. But the pleading only made it better.

“Oh, Blondie,” Felicity purred, “don’t be such a tease. Look how excited your audience is. And they all want you to be naked. You wouldn’t want to disappoint all these lovely girls, would you?”

There was no response from Blondie this time, as he finally seemed to be resigned to his ignominious fate.

“No, I didn’t think so,” said Felicity.

Then she turned away from him and spoke casually, as if discussing the weather. “Now then, let’s see. How shall we go about relieving you of your undies?” She tapped a finger on her lips. “I'll let you take a moment to mentally prepare yourself for your soon-to-be nakedness while I think this over. Oh, and no matter what, you're not to cover up. If you dare move your hands from your head, there will be consequences."

Blondie said nothing. He looked like he might faint.

Felicity turned back to us with a twinkle in her eye. “So...there are a few options. Option one: We could pull down his tighty-whities very slowly—bit by bit—for a nice, tantalizing unveiling. I’m sure it would be delightful for us, and no doubt rather agonizing for him."

Giggles rippled across the bathroom. I could barely contain my own excitement.

"Another option," Felicity mused, "would be to just grab his tighty-whities like this..." She casually stepped behind Blondie. "And yank them down really fast...like this."

Before anyone could blink, she hooked her fingers into the waistband, and to the surprise of all (especially Blondie!), she zealously yanked downward. One second they were snug around his hips; the next, they were pooled around his feet.

Blondie was blindsided. For a heartbeat he stood there in stunned silence, not yet processing what had just happened. Only when Felicity crouched down and tugged the undies free from around his ankles did reality snap into place: He was standing completely, utterly naked in the middle of the girls’ bathroom, on display for a gleeful, all-female audience.

Amazingly—and much to my appreciation—Blondie didn’t move his hands from atop his head, just as Felicity had ordered.

The reaction from the rest of us was instantaneous. Shrieks, howls, and gleeful laughter echoed through the room as we gawked at the mortified, red-faced boy on display. I had last seen his bared goodies back in our sophomore year in Miss Farnsworth's homeroom class. As my eyes scanned his flushed, naked frame, I couldn’t help but smirk. Not much had changed. His dick was still on the small side—maybe just a tad bigger than it was then—but, amusingly, still hairless. Totally smooth.

Of course, thanks to Brenda, I knew he’d started growing body hair—and that, as of a few days ago (at Felicity’s behest), he was required to stay completely hairless. Judging by the comments, not everybody in the room was aware of that tidbit.

"A little wee-wee with no hair!" laughed one girl.

"Poor little freshman baby," chimed another.

"No, he's a senior," someone shouted out (okay, it was me; I couldn't resist). "He's in my homeroom."

A stunned gasp swept through the room. "Oh, my God, are you serious? No way! How old is he?" asked a girl.

“He’s seventeen,” Felicity announced with a wicked grin, setting off another round of howls.

"Oh my God, he's seventeen with a hairless little weenie like that?" a girl behind me shrieked. "Oh, you poor little boy—how embarrassing!”

Embarrassing didn’t even begin to cover it. He looked like he might pass out from shame. It had to be absolutely excruciating for him to be standing there in the girls’ bathroom, stripped naked with his undersized, hairless genitals on full display for an all-female audience that was delighting in his humiliation. His face was positively glowing, and seemed to flush brighter with every biting comment from the energized girls.

Once the laughter died down, Felicity turned the screws a little tighter. "Are they right, Blondie?" she asked. "Is it embarrassing to be 17-years-old and have hairless little bits?" Blondie stared straight down at the floor, and did not respond. “Answer me,” she repeated, her voice firmer now.

"Yes," said Blondie softly.

“Yes what?” she pressed, enjoying every moment.

"It's...it's embarrassing to have...to be seventeen and have lit...hairless little bits," he admitted, his voice breaking slightly.

Laughter rang throughout, and Blondie was about as miserable as one could imagine.

But Felicity had one last debasement for the most unfortunate teen. Still smiling, she bent down, gathered up all his clothes—notably leaving his tighty-whities draped over one of the stall doors—and strolled toward the exit.

She paused at the doorway. “You can put your tighty-whities back on in, oh, three minutes,” she said. "I'll leave the rest of your clothes at your locker. And don't you ever try to resist me again." She wasn't done. "During those three minutes, you are to keep repeating these words: 'I'm completely naked, and I'm so embarrassed, because everyone is staring at my bald little boy bits."

I almost choked on my own saliva.

“Let me hear you say it,” she added.

"I'm na...completely naked, and I'm embarrassed because..."

“Wait!” Felicity interrupted. “You’re so embarrassed. Try again.”

"I'm so...I'm completely naked, and I'm so embarrassed because...because everyone is staring at my...my bald little boy bits."

“Excellent!” Felicity crowed, loud enough to rise above our cackling. “Now keep saying it. For three full minutes.”

"Maybe he can walk around for us while he says it?" I called out. I couldn't help myself. I really wanted to see him walk around naked.

“What a fun idea!” Felicity replied, clearly delighted. “Blondie, walk back and forth across the bathroom for everybody while you say it. For three minutes. Keep your hands on your head. Can someone set a timer?”

The girl next to me paused her recording long enough to set one up.

“Okay,” said Felicity, checking the time. “Three minutes. Starting...now. Start walking.”

And walk he did. For the next three minutes, we were thoroughly entertained by the extraordinary spectacle of the naked teen parading back and forth, hands on his head, reciting his humiliating mantra over and over again: “I’m completely naked, and I’m so embarrassed because everyone is staring at my bald little boy bits...”

His voice was soft and miserable, but loud enough for everyone to hear—and we made sure he knew we were paying attention. His humiliation was off the charts. I genuinely don’t know if it’s humanly possible for a face to be redder than Blondie’s was right then.

When the timer finally went off, Blondie made a beeline for his tighty-whities and yanked them on in nothing flat. The rest of his clothes were gone, of course—Felicity had vanished with them.

I followed him out of the bathroom and watched gleefully as Blondie scampered the length of the hallway in his tighty-whities to rescue his clothes.

That fabulous vision, along with everything that transpired in the bathroom that day, played a major role in inspiring me to write these memoirs.
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