Roosevelt Humiliations

Stories about boys ending up in compromising situations, preferably naked and embarrassed, as the name suggests.
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Blondie
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Roosevelt Humiliations, Chapter 15

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Chapter 15: A Mortifying Measurement

The Measurement

I crouched low and shivering, still completely naked, shaking my head in disbelief. My hands were wedged tightly between my thighs as I huddled on the cold floor, silently praying for a miracle. After a bit there was a knock at the door.

“Knock-knock!” Julie chirped.

“Yes?” I answered the salesgirl anxiously.

But instead of a response, I heard the unmistakable sound of a key sliding into the lock.

“What—hey!” I yelped, just as the door popped open and Julie waltzed in. I scrambled backward, my back hitting the wall. “What’re you... I’m na—I'm not dressed!”

“Not a problem,” she said without batting an eyelash, as if it was standard procedure for her. In her hand was a measuring tape and a clipboard. On the clipboard was a sheet of paper with a drawing of the outline of a female figure. “We just need to get you sized properly. Head to toe. Nothing to be embarrassed about.”

“Oh! Please, I don’t need... at least let me get dressed first...” I stammered.

Julie smiled. “No need for that, honeybun. Nothing I’ve never seen before, so there’s no need to be bashful. Besides, it’s much easier to get exact measurements this way. While you're naked. Now be a good boy and stand up straight for me, hmm?”

With a pitiful groan, I rose slowly, keeping both hands firmly clamped over my modesty as if my life depended on it. I stared straight ahead, face burning, as Julie casually left the door cracked open. Naturally, Becky, Brenda, and the young teens needed no further invitation. The door creaked wider as their grinning faces peeking over each other’s shoulders. Of course, Julie made no effort to discourage them.

Trying (and failing) to suppress her smirk, Julie knelt behind me and gently lifted my right heel. “Hold the end of the tape with your heel, dear. Let’s see how tall we are.” She stood and extended the tape to the top of my head. “Stand tall now... aaand... five-nine and a half. Excellent!” She looked around. “Shoot, I forgot the scale. Don’t go anywhere,” she said with a wink, already halfway out the door.

“It’s okay!” I called back anxiously. “Why do you need my... I weigh one thirty-fi—”

“I’ll be right back! It’s best to weigh you while you’re naked!” she hollered from the sales floor, much louder than necessary.

The giggling girls continued to hang about the doorway while I waited impatiently for the salesgirl. I turned my back to them and bent to a crouch. It was a full five minutes before Julie returned.

“Sorry for the delay,” she said, stepping back in with the scale. “I had to help another customer. But don’t worry, I’m all yours now.”

Wonderful.

She set the scale on the floor and motioned for me to step up. When I did, she announced what I already knew. “One thirty-five. Five-nine and a half, one-thirty-five,” she said, scribbling onto the clipboard. She looked up at the girls. “Excuse me, but could I trouble one of you girls to write down this information for me as I call it out?”

Becky jumped at the opportunity, gleefully entering the room and taking the clipboard. I stood helplessly, still covering myself as best I could, while Becky took her place beside Julie—both clearly reveling in the moment.

“Okay, let’s get your neck size, sweetie. Chin up,” Julie said, gently tilting my head with her fingertips. “Once we get all your measurements, you can go to our website and do your lingerie shopping online... looks like fourteen inches exactly. You have a lovely, slender swan neck.” I groaned softly.

"Now, I’ll need you to hold your arms straight out to your sides, sweetheart, so we can get your chest size.”

“Please,” I whispered, “just... let me put something on.”

Julie rolled her eyes like I was being dramatic. “Now, now, we’ve been over this. Your measurements are much more accurate when you’re nice and naked. Now be a good boy and make this easy for me. Arms out. Nice and straight, like you’re ready to take off.”

I glanced at Brenda and saw the unspoken command in her eyes. With a defeated sigh, I knew what I had to do. Slowly, painfully, I moved my hands from my crotch, exposing myself to the full view—and full judgment—of the room.

“Atta boy,” Julie said with a grin. I caught her eyes flicking down to where my hands had just been. Her smirk widened, unmistakably amused by the view. “See how easy that was? Now let’s get these arms up," she said as she took hold of each of my arms and lifted them up. “There we go—flying position. Hold that pose... perfect!”

She slipped behind me for the chest measurement, most assuredly to give the girls an unobstructed view of my exposed genitals. Becky and Brenda had seen me naked before, but they were grinning brightly, as their enjoyment of my humiliation seemed to have no limits. The young teenyboppers were grabbing onto each other and giggling uncontrollably. It was all I could do to keep from running off.

“Thirty-two inches,” Julie announced. She walked around and gave my chest an appraising look. “That’s a double A cup, for sure.” Another wave of laughter, while Becky dutifully jotted it down.

“Okay,” she continued. “Let’s get your waist size now. I’ll need you to hold your arms up high in the air. It’s best to get the waist measurement while you’re all stretched out, in case you ever want to wear a corset.” I grudgingly raised my arms slightly. “All the way up, please,” Julie directed. Reluctantly, I obeyed. "Now interlock your fingers and face your palms to the sky... no, turn them up, so your body will be nice and taut... there you go, perfect... you’re all stretched out now... I must compliment you on your hygiene... you have such lovely, smooth underarms.”

The giggling intensified. It was true; while I’d started to grow hair elsewhere, my armpits were still as smooth as a child’s.

She walked behind me to take the measurement, affording the other girls what for them was I’m sure a very entertaining view. “Twenty-eight inches." After a pause, she said, “With a corset I think you’ll have a lovely hourglass figure.”

I dropped my arms again, my hands snapping back over my crotch like magnets. Julie came back around and faced me.

“Okay, we’re almost done. I just need to measure your hips so your panties will be properly sized.” I groaned softly to myself as Julie knelt once more. She looked up at me. “You’ll need to hold your arms up and out of the way, sweetie.”

With a defeated sigh, I crossed my arms over my chest and tried to pretend I wasn’t standing there naked, being sized for panties. I felt the tape wrap around my hips. Her eyes were no more than two inches from my penis as she purposefully scrutinized her objective—and at that moment, I don’t think it was the tape. As she stood up, she couldn’t suppress another smirk, only now it was more pronounced.

“Definitely an extra small,” was her stinging remark. While everyone laughed, she gave my flushed face a sympathetic pat. “There, that wasn’t so bad, now, was it?”

As everyone trickled out, still laughing, Julie turned back and chirped, “Be right back with your bra and panties!”

The door clicked shut, and I locked it in a hurry. I leaned against it, face in my palms, and muttered into my hands.

“Oh... my... fucking... God.”


Bra and Panties

My reprieve was short-lived. Barely two minutes had passed when Julie’s hand appeared over the dressing room door, holding a pair of lavender-colored lace panties.

“Would you try these on for me, please?”

Shuddering, I took the panties and gingerly slipped them on. They hugged me a little too well. I winced as I glanced downward.

“Well?” Julie’s voice was expectant.

“They’re... fine,” I answered meekly.

Next came the matching bra, casually tossed over the top of the door as if it were a common t-shirt. “Don’t forget your bra,” came the cheery voice from the other side of the door.

I reluctantly slid the shameful garment off the door and stared at it like it might bite me. I had no idea how the straps worked. Julie, sensing my struggle, piped up again.

“Slip your arms through the openings, sweetheart, then clasp it in the back. Would you like some help?”

“No!” I blurted out quickly. “I mean... I can do it." After a struggle, I finally managed to secure it. I felt ridiculous, and more than a little humiliated.

“How are we doing in there?” asked the all-too-helpful Julie.

“Fine. They fit fine. Really. I’ll take them... please. If that’s what you want.”

There was a brief pause.

Maybe she's done? Maybe this is the end of it?

“Just to be sure, I think we should have a look in the mirror.”

Of course she does.

I closed my eyes for a moment to gather myself. Then I opened the door.

“Oh, you look adorable,” Julie gushed. “Do you feel as sexy as you look?”

I didn’t dignify that with a response. I power-walked toward the mirror, wishing I had a paper bag for my head.

As expected, I was met by a growing crowd of grinning faces. Becky and Brenda were beaming, their amusement seemingly limitless. The teenage girls were practically bouncing with glee. The tall blonde customer observed from a distance, looking thoroughly entertained. And now, because this clearly wasn’t humiliating enough, another saleslady and two new customers had stopped their browsing to watch.

When I reached the mirror, the girls formed a semicircle around me, looking on with great amusement. Julie sidled up to me. “Oh yes, this is definitely you,” she said, adjusting the lace along the bra cups. “Lavender is such a lovely color on you, don’t you think so?”

“Yes... I mean, no... I mean—I’ll take them... please!”

The two new customers had wandered closer, whispering to each other with amused interest. I needed to get out of sight immediately. I spun and bolted toward the dressing room, desperate for cover. But to my horror, the door was closed—and locked. Someone was inside. In a mini-panic, I looked around for another dressing room, but there was none to be found. I knocked frantically on the door.

“Excuse me, but can I get in there?” I asked anxiously.

A woman’s voice replied, “I beg your pardon, young man, but I’m busy in here.” The occupant paused and peeked at me over the door, looking me up and down. Tall Blonde Lady from before. Grinning widely, she calmly said, “She’s right, you know. It is a lovely color on you.”

My nightmare was reaching a fever pitch. I stood stiffly by the door, one arm crossed over my chest, the other shielding the front of the panties. It wasn’t until later, replaying the scene in my mind, that it struck me: I was striking the exact pose any modest girl in my situation probably would’ve assumed. And once that realization sank in, it only deepened my shame.

Eventually, the lady emerged with a wink, and I scrambled inside, slamming the door. I breathed a sigh of relief like never before. But then I realized—my clothes were still missing. I poked my head above the door and looked around, but they were nowhere to be seen. I spotted Julie a few yards away. She was still grinning.

“May I please have my clothes now?” I called out to her.

“Sure!” came Julie’s cheerful voice. “I’ll get them for you. First, though, hand me your bra and panties, and I’ll wrap them up for you.”


Naked Again

I sighed and peeled off the offending garments. They were snatched from the door in a blink, and once again I was left naked and waiting... and waiting... and waiting... and waiting...

“Excuse me?” I shouted, now with impertinence. “I’m still waiting for my clothes!”

“Sorry, I’m helping another customer," Julie called back. "Your clothes are hanging on the rack with the babydolls. You’ll have to get them yourself.”

I groaned. I should have known it would come to that. Peeking out, I scanned the store. I had no idea what a babydoll even was, but clearly I wasn’t going to find my outfit without parading naked through the store. Desperate, I grabbed a tennis shoe. I held it over my genitals, which easily fit inside the opening of the shoe. Then I made a break for it.

The store exploded in laughter. Out of the corner of my eye I saw several people peering through the window—one of them pointing at me with glee. I darted from rack to rack, searching for anything that resembled my clothes. No luck. Tall Blonde Lady was headed toward the dressing room again, and I barely beat her to it, slamming the door and screaming: “Please! Someone just bring me my fucking clothes!”


The Teddy

There was silence. Then, ominously... the fuchsia teddy was slowly sliding over the top of the door. Becky’s voice followed. “That’s no way for a young lady to talk. Now put on your new teddy and let’s go home.”

“Oh, shit,” I muttered to myself. I pulled the teddy off the door and leaned against the wall, feeling hopeless. “Ohhh, shit.”

“Open the door!” Becky demanded.

In a rush, I pulled the teddy on—again—and turned the knob. Becky burst in, holding a shopping bag.

“If you’d just asked nicely,” she teased, “I would’ve given these to you.” She showed me the contents—my shorts, t-shirt, underpants—and then she dropped in my shoes and the frilly socks.

“Let’s go,” she said with a smile.

“Oh God, please, Beck! I can’t—not in the mall!”

Becky simply tugged at my elbow. I pulled loose and tentatively ventured out of the dressing room. Once again, I was the center of attention. I briskly walked toward the exit. But there was Julie, waving merrily from behind the counter.

“Yoo-hoo! Don’t forget to pay for your lingerie, sir!” she called, delighting in every word

I gave Brenda a desperate look. She smiled and nodded toward the counter. Becky reached into the shopping bag, retrieved the credit card, and handed it to Julie. She took an unusually long time to complete the transaction while I stood there, mortified to the max.

At last, the smiling Julie handed me the pink bag containing my new bra and panty set. The bag had giant “VS” logo emblazoned on both sides. “Thank you so much,” she said. “You’re my new favorite customer. Please come back soon. I’ll be happy to help you any time.”

I turned to leave, and Becky jabbed me in the ribs. “Thank her for her help.”

"Thank you for your help,” I mumbled, trying not to cry.

“Oh, trust me,” Julie said, her smile wicked, “the pleasure was all mine.”

The walk through the mall was its own special kind of torment. Becky and Brenda each gripped a hand, towing me along at their leisurely, agonizing pace while the two young girls trailed behind, giggling openly. I tried to hurry us along, desperate to escape the gawking eyes around us, but my sister and Brenda held me back—even pausing at one point to casually order ice cream.

By the time we finally reached the exit, I’d lost track of how many people had stared, whispered, pointed, or laughed. I heard one wolf whistle, an “Oh, how darling!” from a passing group of women, and—just to seal my humiliation—a booming female voice that echoed off the high ceilings: “Look at the pretty boy in the lingerie!” I must have turned every shade of red imaginable during that public display.

When we stepped outside, the two teenagers lingered at the entrance, watching as we crossed the parking lot. Even after I scrambled into the car and pulled the door shut, the sound of their giggling voices still rang in my ears.
Last edited by Blondie on Tue Mar 17, 2026 8:09 pm, edited 7 times in total.
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Roosevelt Humiliations, Chapter 16

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Chapter 16: Tormented by Becky and Brenda

Under Brenda and Becky’s Thumb

Well, again I must apologize for taking so long in between the accounts of my humiliating travails at the hands of Brenda, Becky and the others from Roosevelt High. You see, I’ve been trying to put it out of my mind—but of course, considering the magnitude of my shame, that’s impossible to do. So I may as well finish what I have started, for posterity’s sake, and for the sake of any readers still grimly amused by my suffering.

Here’s a refresher, just in case you’ve managed to forget what I can’t: My junior year is finished, but I still have a few incidences to relate that occurred during my junior year and in the summer. When we last communicated, Brenda and my sister Becky had thoroughly humiliated me at the mall, where I was put through my paces at Victoria’s Secret. I even had to buy a teddy, and my own bra and panties set.

After that incident, I understood my position clearly: I was completely under their control. Any time I so much as considered defying them, I had only to recall the beach episode—where I ended up stark naked in public and later forced into one of my sister’s swimsuits—to remind myself just how bad things could get. And I had no doubt things could, and would, get worse if I stepped out of line again.

Much to my detriment, Brenda and Becky have become very good friends. In fact, they have formed quite the bond, and when the two of them put their scheming, devilish heads together, it never bodes well for me. Whenever Brenda comes over, I feel a wave of dread washing over me. Dealing with Becky alone was hard enough, but the two of them together? That was a recipe for disaster.

Disaster struck one Sunday evening. I wasn’t in a good mood to begin with. I hadn’t had much sleep the night before, I had lost a bet on a football game, and Brenda was at the house visiting. That combination was enough to make me incredibly irritable.

I was lying on my bed reading the sports section when Becky and Brenda barged into my room without knocking.

“Hi, Blondie,” sung Becky as the two of them stood over me with predatory smiles. “Whatcha doin’?”

It was obvious their intent was to tease me, and I was in no mood for their shenanigans.

“What does it look like I’m doing?” I grumbled. “And could you please knock next time? This is my room, you know.”

“Ooh, it must be that time of the month for Blondie,” teased Becky.

“Maybe Blondie’s afraid we’ll surprise him while he’s massaging his little weenie,” Brenda chimed in. They both laughed. “Or maybe he was just about to try on his pretty new outfits from Victoria’s Secret.”

They both laughed again, while I seethed and blushed behind my paper.

“Hmm, what a great idea, Brenda,” Becky considered. “Blondie, we’re kind of bored right now. How would you like to model your lovely new lingerie for Brenda and me?”

My guard was down, and I spoke without thinking. “Eat shit, Becky, and get the fuck out of my room!” I shouted. The moment those words left my mouth, I knew I’d messed up.

“Okay, that’s it, Blondie,” reprimanded Becky, her tone ice cold. “I’ve had quite enough of your attitude lately. And to act like that in front of my guest... you’re going to pay for this.

She turned to Brenda. “Come on. We need to have a little strategy session.” Before leaving, she shot me one last glare. “And don’t even think about leaving this room. Do you hear me?” I didn’t answer. “I said, DO YOU HEAR ME??” I nodded meekly.

They left my room. Brenda paused in the doorway and puckered her lips while giving me a fake kiss. “See you soon, Blondie.”

As I lay on my bed my mind raced, and I was dreading what diabolical conspiracy they were devising. At least fifteen minutes passed before the grinning girls re-entered my room, again without knocking. To my dismay, Becky was dangling the bag that I recognized from Victoria’s Secret. She noticed me gazing at the bag with a look of pure apprehension.

“Does this look familiar, sweetie? How about this?” She reached into the bag and pulled out the lavender-colored bra and panty set. “Remember how precious you looked in these?”

“Please, Becky, I’m sorry, I don’t know what got into me earlier. I’m just... really tired. Honestly, I didn’t mean it.”

My pleas fell on deaf ears. “Well maybe next time you’ll think twice before giving me any of your dirty lip. In the meantime, you need to learn a lesson. Now, here’s what’s going to happen: You’re going to put on your new bra and panties and come out to the living room, wearing nothing else. Brenda and I are hungry, so maybe you can serve us dessert while you swish around in your cute little girly undies.”

I stared at her in disbelief, but she wasn’t done.

"Then, if you’re really nice,” she added with a smirk, "we might even put on some music and let you entertain us with a little dance. On the coffee table. In your sexy underwear. Now strip off those boy clothes and make yourself pretty for us. We’ll be waiting for you in the living room. You’ve got five minutes.”

She dropped the lingerie on my bed, and Brenda came up behind her. “Don’t worry, sweetheart,” she cooed, pinching my cheek. “You’re going to look adorable. And I have a feeling you’re going to be quite the dancer.”

They left me alone with my doom. I stared at the delicate lace for a long moment, the color draining from my face. Then, with a deep, resigned sigh, I slowly, deliberately started stripping off my clothes. I couldn’t believe I would have to wear the bra and panties again. I tried to comfort myself with the fact that at least I wasn’t in a public place. But Brenda and Becky were enjoying my disgrace way too much, and the thought of serving them and then (oh, God) having to dance on the coffee table for their entertainment while wearing a pair of panties and a bra... that was a dreadful notion.

But I had no recourse—to disobey them would mean much worse repercussions down the road. Shuddering, I slipped the panties up my legs. I pulled the bra on and managed to clasp it in the back. Then, while looking in the mirror, I pulled the straps over my shoulders and took in the very discomforting reflection. I actually turned around to see how I looked from the rear, then immediately chastised myself for doing so. I remember thinking that from the rear, I could probably pass as a girl (which would only give the girls more ammunition to tease me with), what with my smooth skin and slim features. Fortunately, I had grown some hair on my legs. It was blond, and not that noticeable, but at least it offered a hint of my masculinity.

I sat on the bed with my head in my hands. My moment of self-pity was short-lived.

“Blondie, we’re waiting,” Becky’s voice sang from the living room. “Come on out and shake those hips for us!” Loud giggling from the two girls ensued.

My sweaty hand was on the doorknob when I heard what was, at the time, music to my ears: the front door opening and the voices of my mom and dad. They had come home from the movie much earlier than expected.

I exhaled hard. No way would Becky want our parents to know of the depravity she was inflicting on me. I’d even considered telling them myself, but I always squelched the idea—once Mitch found out, I’d be dog meat.

In any case, for the moment I thankfully had a reprieve. I turned around to get dressed, but just as I did, Brenda barged in. My back was to her as I scrambled for my clothes.

“Oh, Blondie, how cute,” taunted Brenda as she squeezed my pantied ass before I managed to pull up my jeans. I didn’t bother stripping off the lingerie. I quickly pulled on my jeans and tee shirt right over them so Brenda wouldn’t see me naked. I turned around, my face burning

Brenda just smiled at my blushing face. “Thanks for the sneak preview, Blondie. We’ll have to pick this up where we left off sometime.”

She exited the room with a giggle as I felt a pang of anxiety over the prospect of a repeat performance, but breathed a sigh of relief over escaping certain humiliation that night.


More Roosevelt Humiliations

My reprieve didn’t last long. At school the next day, I had just finished eating lunch and was kicking back, taking in a few rays while leaning against the Roosevelt statue. I should have known better than to go near that damn thing—it seemed like every time I did, something awful happened. Sure enough, my moment of tranquility was shattered by the ominous, too-cheerful voice of Brenda.

“Well, well, well... Blondie. How nice to see you.”

I wasn’t fooled by the cheerful tone. I opened my eyes to find Brenda, Becky, Marcia, and Cheryl standing over me, all wearing smiles. One look at their faces, and I knew—something awful was about to happen.

“I hear you look positively adorable in lingerie, Blondie,” Marcia teased. “It would be such a treat if you could put on a fashion show for us sometime.” They all giggled.

“Oh, absolutely,” Becky added, taking the cue. “He makes a lovely little teenybopper.”

The giggles intensified. Becky inched a little closer to me while reaching into her purse and pulling out a tube of lipstick. A sudden fear swept over me as I eyed the lipstick tube like it was a rattlesnake ready to attack.

“Can you believe,” she said to the group, “that he told me to ‘eat shit’ last night? Such language! I mean, is that any way for a proper young lady to talk?”

I jerked my head back as the lipstick inched toward my face, but Brenda was faster. Her hands gripped my shoulders, firm and unrelenting.

“Hold still, darling,” she whispered, just loud enough for me to hear the amusement in her voice.

“Maybe if you looked more like a girl,” Becky mused, “you’d learn not to talk to your fellow females so rudely.”

Before I could wriggle free, she was applying the lipstick. It was bright pink, thick and greasy. Her movements were slow and deliberate, drawing laughs from the entire group as I sat there, mortified.

What is it about these girls that they get off on feminizing me?

Becky stepped back to admire her work, smirking. “That’s a good girl, Blondie. Now hold still while I add a little blush.” She paused, tilting her head as she scrutinized my face. “On second thought, your cheeks are blushing on their own, you don’t need this." She burst out laughing. “You look marvelous, sweetie.”

She opened her compact and held up the mirror. I was chagrined to see a youngish-looking boy with bright pink lipstick and very red cheeks. I glanced around, silently praying that no one else had seen me like this. But Becky, as though reading my mind, took care of that in short order.

“Oh hey, look over there,” she said casually, pointing toward two girls chatting nearby. “Do me a favor, Blondie. Go ask them if they have any eye shadow you can borrow. If you succeed, I’ll let you wipe the lipstick off. If not...” She let the silence hang for effect, then: “...you have to wear your cute little bra and panty set to school tomorrow. Instead of your underwear.”

I tried to find a way out of the predicament. “Beck, please. I’m really sorry about last night. I swear, it won’t happen again.”

Becky smiled. “Go, girl, before I put you over my knee and give you a spanking. And rest assured, I’ll pull down your undies and give you a bare-assed slapping that you’ll never forget.”

The girls howled, the sound of their laughter drawing eyes from across the way. I needed no more prodding.

I reluctantly stood up and made my way over to the two strangers. I decided to take the direct approach. “Excuse me,” I said, folding my lips inward as I approached. “Do either of you... um, have any eye shadow?”

“Why do you want eye shadow?” asked one of them, a petite brunette. Her eyebrows were furrowed in confusion.

“It’s for my sister,” I blurted, pointing toward Becky’s group, once again awkwardly tucking my lips.

That exchange served two purposes, both to my detriment. First, by speaking, my newly painted lips were exposed to the two girls. Second, when I pointed out Becky, the two girls turned and saw my four tormentors in hysterics—pointing, laughing, clearly enjoying the spectacle. It didn't take a genius to figure out that I was the victim of a Roosevelt High hazing. The faces of both girls lit up. They pounced on the opportunity to join in the festivities.

“Come on now, ‘fess up,” the brunette teased. “The eye shadow is for you, isn’t it?” Both girls were giggling.

“N-no, really,” I stammered, looking down at the pavement as my face turned a new shade of red. “It’s for my sister. Please, can I just get some?”

The brunette, clearly enjoying herself, reached into her purse. “How cute,” she continued, “You're like a little schoolgirl, wearing lipstick and blushing like that. I’ll tell you what: You can have some eye shadow if you let me put it on you.”

I hesitated, weighing my options. Public humiliation now, or bra and panties tomorrow?

“Okay,” I muttered.

She grinned, pulling out a compact of baby-blue shadow. As she lifted the applicator, I instinctively closed my eyes. I could hear my sister and her gang laughing from the sidelines, the sound carrying across the courtyard.

“Oh my god,” the brunette’s friend squealed. “I can’t believe this!”

Indeed, neither could I.

I felt the soft brush against my lids, a delicate, feminine sensation. When she finished, she stepped back with a satisfied nod.

“Oh, yes, you look lovely, little schoolgirl.”

More giggles. I had quite enough. I turned and walked back toward my tormentors, my head down.

“Thanks for coming by, cupcake!” the brunette called after me.

I walked from the laughter of two strangers back into the cackling of four maniacs. Just as I reached them, the bell rang—the only mercy I’d received all day.

“You can go clean up now, Blondie,” Becky said, handing me a Kleenex while wiping tears of laughter from her own eyes. “But don’t get too comfy. I still owe you for last night.”

I didn’t stick around to hear more. Spitting out the awful taste, I bolted straight for the bathroom, which fortunately was empty. I wiped off the lipstick and scrubbed off the makeup as fast as I could. I shivered, angst-ridden at the possibility that Becky still had a reprimand in mind.

Sure enough, it came just a few days later—in spades.
Last edited by Blondie on Mon Mar 23, 2026 6:14 pm, edited 5 times in total.
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Roosevelt Humiliations, Chapter 17

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Chapter 17: The Bubble Bath

Denuded

It was late Saturday afternoon, and I came home after two grueling hours of basketball. My parents were out of town for the weekend, and Becky had gone off on some overnight adventure with Brenda. I had the place to myself, and I was looking forward to it.

I peeled off my clothes and went into the bathroom to take a shower. Just as I was about to turn the shower on I spotted my sister’s bubble bath tucked in the corner of the tub. I was a little sore from basketball, and I figured a good soaking would do me good, so I ran the water and poured in some bubble bath liquid. I don’t know what got into me—I hadn’t taken a bubble bath since I was a little kid, but in that moment, I didn’t care. The water was perfect. So perfect, in fact, I started nodding off.

I don’t know how long I was out, but I was rudely awakened by a tickling sensation on my balls. I opened my eyes and nearly died on the spot. Standing over me were the grinning faces of Becky and Brenda.

I yelped and instinctively swatted Brenda’s hand away. The two girls were laughing uproariously as I flailed about for a while, at a loss for what to do. Finally, I realized that I best not disturb the bubbles—they were the only protection I had for my modesty.

“Well, well, brother dearest,” Becky purred, her eyes dancing with delight. "Is this sweet revenge, or what?”

Of course, she was referring to the time many years before that a friend and I intentionally walked in on her while she was taking a bath. She’s never forgiven me for it and was surely in her element over the classic case of poetic justice.

“How precious. A bubble bath," teased Becky. "Let’s see, you bought a bra and panty set, you’ve been wearing lipstick and eye shadow, and now you’re soaking in a bubble bath like a little sissy. It seems to me you want to be a girl. Well, just sit back and relax, sweetheart. Auntie Brenda and I are about to make your dreams come true.”

The smiling Becky reached across the tub and grabbed her pink disposable razor.

“Brenda, there’s another one of these in the medicine cabinet. I’ll start on his legs, maybe you can shave his underarms, if he has any hair under there.”

Becky giggled, and Brenda, grinning mischievously, wasted no time producing another razor.

“Hold up your leg,” demanded Becky.

“What? No! Becky, stop!” I was horrified. I was a late developer, something that had grated on me, and when I finally started growing body hair, I was quite grateful. Now, with its removal imminent, especially at the hands of the devilish Becky and Brenda, I was quite shaken. "Please, I’ll do anything! Just don't!” I had bolted upright and was screaming.

“Anything?” Brenda asked, popping the cap off a second razor. “Then lie back and hold still, sweetheart. Let your loving sister and Auntie Brenda make you niiice and smooth, like the little girly-girl you are.” She tried to ease me back with her hand pushing on my chest, but I resisted.

“That does it, I’m getting the scissors,” interrupted Becky. "Let’s cut off all his pubic hair, then we’ll take some pictures.”

“Okay, okay!” I relented, lowering back down. My situation was dreadful enough, but I didn’t want to lose my precious pubes.

That got their grins back. Becky grabbed my foot and lifted my leg into the air. I couldn’t believe what was happening.

“There we go. Now hold still, sweetie. We don’t want any nicks on those pretty legs.”

She squirted a puff of shaving cream into her palm and smeared it over my shin. She started at my ankle and made a few sweeping motions with the razor, all the way to my knee.

“It was a good idea to take a bath, Blondie," Becky teased. "The hot water softened everything up. Look at that—it’s coming right off.” I closed my eyes, wincing, as I couldn’t bear to watch.

Then Brenda grabbed my wrist. “Arm up, sugar plum. Let’s see what’s hiding under here. Oh, yes—definitely some fuzz. We can’t have that, now can we? A proper girl should have nice, smooth underarms. Hold your arm waaay up high, dear, so we can get rid of these unsightly things.”

Miserably, I complied, much to my dismay. I had finally started growing armpit hair just a few weeks before; now, it was vanishing in seconds.

While Becky continued working her way up my leg, Brenda made short order of the small amount of hair on my right armpit. “Other side now, pumpkin. Turn toward me—good girl.” Hearing Brenda sweet-talking me and calling me a girl only added to my extreme mortification, and she knew it.

She finished off my other armpit and ran her hand in a circular motion around my chest. “Oh yes, nice and smooth. We don’t need to spend any time here.”

Brenda noticed my flushed, miserable expression and gently stroked my cheek with the back of her hand. “Aww, don’t pout, sweetheart,” she cooed. “By the time we’re done with you, every boy in school will be lining up just for a chance to get into your pretty little panties.”

Becky, who was intent on her job of denuding my leg, broke her silence by breaking into convulsive laughter. “Oh, Brenda, you’re too much!” she laughed as she lowered her head onto Brenda’s chest until she exhausted her laughter.

“You’re quite the card yourself,” answered Brenda, joining in her frivolity.

Great, the mutual admiration society between a pair of dominant females.

I tried to let my leg slip back into the safety of the bubbles, but Becky’s grip tightened. “Hey, I’m not done yet!” Becky said, tugging it back up. "Hold your leg way up high. I need to finish off your thigh.”

I raised it again and dared a quick peek. My lower leg was already porcelain-smooth. I winced—and of course, Brenda noticed.

“Pretty, pretty,” she teased, drawing out the "t" sound as she traced her fingers lightly up and down my smooth calf.

I squeezed my eyes shut, hoping to wake up from the nightmare. But Becky quickly brought me back to reality by lightly patting the underside of my thigh. “All done, sweetheart. Now let’s have the other one.”

I resignedly lifted my other leg. Becky pulled it toward her and lathered it up. Almost seventeen long years to finally grow, I remember thinking, and it was all disappearing at the whims of the fiendish twosome.

As Becky began the first long stroke of the razor, looked up at me with a sparkle in her eye. “I notice you’ve got some fuzz on your arms, too. You need to look pretty when you model your lingerie for us later. That means no unsightly hair on the arms. I think you could use the practice, so you’ll be able to do this on your own next time. Brenda, give Blondie the razor—let him do the honors.”

“What a brilliant idea, Becky.” They were feeding off each other now. “But he has to ask nicely first.” I stared at them wide-eyed. “Go on,” Brenda encouraged. "If you ask us very nicely, we’ll let you shave your own arms. If you don’t ask nicely, I’ll take over—and I might get a little carried away and snip a few pubes while I'm at it."

It was a new rock bottom. Not only was I being systematically denuded, but I had to beg for the privilege of doing the dirty deed myself. It took some resolve, but I pleaded in the nicest voice I could muster up under the circumstances. “Brenda and Becky, could I please... please, may I shave my arms?”

I couldn’t believe the words I had just spoken. The bathroom rang with their delighted laughter at my debasement.

“Of course, darling,” Becky giggled, handing over the razor and shaving cream. “Make your arms silky smooth, just like a girl's.”

With trembling hands, I lathered my left arm. “That’s it, doll face,” said Brenda, leaning over my shoulder. “All the way up to the shoulder. We don’t want any stray 'boy' hairs ruining the look, do we? That’s a good girl, completely hairless,” she purred as I somehow turned a deeper shade of red.

By the time I finished both arms, Becky had cleared my other leg. Brenda plucked the razor from my hand. I couldn’t take my eyes off my now-hairless arms. I suppose I’d gotten so used to seeing that light layer of hair every day that the sudden change was a shock. The skin looked unnaturally smooth—so bare, so exposed. It really sank in, in that moment, what they had done to me. I was mesmerized—until I was quickly pulled out of it by Brenda, who noticed my fascination.

“That’s right, sweetheart,” she cooed. “Just like a girlie’s arms. I’m dying to see how your pretty your legs look.”

She reached into the tub and pulled out the drain plug. The water slowly drained, and the "glug-glug" sound was quite ominous. In desperation, I jammed my heel over the drain.

“Now, now, Blondie,” warned Becky. “Don’t make me go get the scissors.”

I flinched and moved my foot. The water again started draining. “Please, you guys,” I appealed. I was near tears. “You’ve done enough. Please go away and leave me alone.”

“And miss the big reveal?” Becky countered. “We have to see the fruits of our labor.”

I lay in the tub, staring at the ceiling, as the water made its inexorable disappearance down the drain. When all the water was gone, my body was covered with a layer of bubbles.

“Stand up, cutie pie,” Becky commanded. "Let’s spray you off so we can see how smooth you are.”

I stood, my back turned and my hands clamped over my crotch. Becky grabbed the handheld showerhead. I gasped as the cool spray hit my scalp and cascaded down my spine, washing away the last of the bubbles. Behind me, the girls were oohing and ahhing at the sight.

“Ooh, Becky, great job on the legs! They’re adorable!” said Brenda as I felt her hand running up and down the back of my left thigh. Then, to my distress, I felt her hand running in a circular motion across my butt cheeks. “And his little buns are baby-smooth, too.”

“I know,” Becky giggled. “And I didn’t even have to shave there.”

While the girls burst into laughter, I stood there, utterly mortified, water streaming down my bare, silky skin. My sister and her best friend looked me over with gloating pleasure, like proud artists admiring a masterpiece they’d just finished.

“Okay, the moment of truth, cute cheeks,” Becky chirped. “God, this is fun! Turn around, Blondie. Come on, snap to!"

I didn’t delay the inevitable. I turned around, my hands still covering myself.

“Arms up high, girlie-boy,” she instructed. I hesitated for a split second. “Come on, up, up, up!” she insisted.

With a deep sigh of surrender, I raised my arms over my head. The bubbles still clung to my skin, but we all knew that wouldn’t last.

Becky turned to Brenda with a wicked grin. “Would you like to do the honors, my dear?”

“With pleasure.” Brenda took the showerhead and aimed the spray directly at my face, letting the water run over my forehead, my cheeks, and then down over my now embarrassingly smooth underarms—which, of course, drew delighted giggles.

“Oh my god, this is too precious!” Becky squealed as the water stripped away the last of my cover.

“Doesn’t she have the cutest little clitty?” Brenda mocked.

Both girls busted out with laughter at the gibe. I couldn’t imagine feeling more humiliated than I was at that moment.

“Okay, out you come, cutie pie,” Becky ordered, beckoning me with a finger. “Let’s dry you off.”

I stepped out of the tub. It seemed like I’d been in there for days. Brenda was waiting with a fluffy towel and a grin that stretched from ear to ear. She began gently patting me dry, treating me like a pampered little doll.


Their Plans for Me Revealed

As Brenda dabbed at my shins, Becky stood beside me with a glint in her eyes—and then dropped the bomb. “Guess what, Blondie? We’re having a little slumber party tonight, and we’ve decided you’re going to be the entertainment. Won’t that be fun? Joanna will be here, and Marcia, and Cheryl, and maybe a couple of others. You’d better be careful—I know Joanna and Marcia don’t like pubic hair on their boys. Oh, and if you’re really, really good, we might even invite Mitch.” My eyes went wide. Becky smirked knowingly. “Don’t you think he’d love to see how pretty you look? All smooth and silky?”

I opened my mouth to protest, but no words came out. I didn’t want to even think of what type of entertainment my evil sister was referring to. And the reference to the pubic hair was disturbing. Keeping my pubic hair was the only positive I could take from the god-awful experience in the bathtub.

Brenda hung the towel as Becky reached for a bottle of body lotion, dispensing a generous dollop into her palm. “This will make your skin sooo soft. And you’ll smell nice and pretty, too," she said as she began massaging the lotion into my chest and stomach. Already the very feminine scent had taken over the room.

“Hold out your hands, sweet pea,” Becky said cheerfully. I obeyed. She dispensed another healthy glob into my palms. “Now rub it into those pretty arms and legs. Really massage it in.”

I did so, and the smoothness I felt by touching myself served as a stark reminder of my new condition. It wasn’t just my appearance that had changed—it was the feel of me. Every inch of my body was smooth, scented, and soft. It was impossible to ignore. As my hands glided over my bare skin, I cringed at how delicate and feminine it felt. The silky texture under my own touch was completely foreign—unnerving, even—and knowing that it was all their doing only made it worse. I wasn’t just humiliated by what they’d done to me... I was humiliated by how it felt.

Brenda leaned in, sniffing my shoulder. “Oh, Blondie, I’m telling you, you’re going to drive Mitch absolutely wild!”

Both girls laughed heartily and led me out of the bathroom. The moment I stepped into the hallway, I stopped dead in my tracks. Greeting me was a full-length mirror. I stared at my reflection, completely taken aback by what I saw. It didn't feel like I was looking at me. My skin was so smooth, so hairless. I looked... delicate.

Brenda pounced on my hesitation. She stepped behind me, guiding my arms up to cross them over my head, then placed hands on my waist. We stood there, cheek to cheek, staring at the reflection. “See how lovely you look, sweetie?” she cooed.

I couldn’t take it anymore. I let my arms drop and looked away. Becky took my right hand and started leading me toward her bedroom.

“Come on, girlfriend,” she said. “Just wait till you see what we’ve picked out for you to wear tonight.”

And somehow, I knew... the worst was still to come.
Last edited by Blondie on Mon Mar 23, 2026 10:12 pm, edited 4 times in total.
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Roosevelt Humiliations, Chapter 18

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Chapter 18: Spanked and Pantied

Disciplined

I shivered in my nudity as my sister Becky led me by the hand down the hall toward her bedroom. Brenda playfully gave my bare backside a playful squeeze as she walked behind us. I instinctively swatted her hand away, and she just giggled with glee.

The two devilish girls were in their full glory, practically buzzing with delight, while I was sinking deeper into the depths of misery. Every inch of my body—except one very critical area, thank goodness—had been shaved smooth at the hands of the two witches. A scented lotion had been rubbed all over my body, as they seemed intent on humiliation through feminization. And now I was facing the horror of a slumber party with their friends... with me as the night’s "entertainment." I didn’t even want to know what that meant.

Becky led me into her bedroom and released my hand, leaving me standing awkwardly in the center of the room. My hands immediately flew to cover my crotch. Becky opened one of her dresser drawers and casually started rummaging through it, like she was picking out socks—except, much to my horror, she was fishing through her panty drawer.

“Let’s see, Blondie,” she said in that syrupy sweet voice. “Since you’re so intent on covering up your little bits, maybe we can help you out... ah, here we go, I think you’ll look quite stunning in these.” She held up a bright pink pair of panties and stretched them between both hands. “What do you think? Is this your color or what?”

The girls burst into laughter. I just stood there with a distressed, somewhat frightened look on my blushing face. My hands tightened a little bit on my privates, and I bent over slightly from the waist—my body language practically broadcasting my shame.

“Please,” I implored. “Don’t do this to me.”

Of course, my appeal fell on deaf ears. Becky knelt down, holding the panties open at my foot. “Step in, sweetie. Time to get ready for your guests.”

I started to comply—lifting my foot, just barely—before panic took over and I made a break for the door. I must have been delusional to think I could escape from my tormentors.

“I wouldn’t do that if I were you,” Brenda cautioned, not even bothering to give chase. “One phone call to my cousin and you’ll find yourself naked in public before you know what hit you.”

I stopped in my tracks. No need to remind the reader about Mitch and his threat. Suffice it to say, it was enough to have me completely under their control. I turned around, defeated. Brenda was perched on the edge of the bed now, patting her lap. “Get over here, little girly-boy,” she said.

I timidly walked over, covering myself the whole time, until she grabbed my wrist and yanked me down across her knees. She didn’t waste a second getting me into position—my bare ass cheeks propped up, as if they were begging to be slapped—and then came the first sharp smack. To exacerbate my humiliation, Brenda scolded me while she went about the spanking. Methodically, each word coincided with an authoritative slap on my naked behind.

“How dare you disobey your sister like that!” she scolded, each word punctuated by a firm slap. “You should be ashamed of yourself!” Oh, I was. I was beyond ashamed. And It was really starting to sting. “Now get your little ass up and put your pretty panties on like the girlie boy you are!”

Count ‘em, that’s thirty-two bare-hand spanks, and they came in rapid succession. My backside felt like it was on fire.

Brenda, who obviously derived considerable enjoyment from her spontaneous discipline session, pushed me to the floor, where I landed in a heap. I stumbled to my feet, wincing, clutching both my ass and my crotch like I didn’t know which to protect first. I hopped in place a few times, completely involuntarily, which just set the girls off in another fit of laughter.


Pantied

Becky was waiting with the panties, now looking even more jubilant. I approached her and lifted my foot again, resigned to my fate.

“That’s a good little girl, Blondie,” she said with a wink.

I winced, both at my submission to being dressed in my sister’s panties—by my sister—and at the use of the word “girl." She tapped my shin, and I lifted my other foot, allowing her to slip the other opening of the panties over my leg. She slowly, teasingly drew them up my legs, then she let go and just stood there, grinning at me while they drooped around my thighs.

“You’re going to have to move your hands, sweetheart, so we can pull your panties up,” she said.

I hesitated, then dropped my hands to my sides, mortified all over again. Even though they’d seen everything already, somehow standing there with pink panties dangling at my knees felt worse. Becky sensed my extreme discomfort and pounced on it. Instead of pulling the panties up, she stood up and put her arm around her fiendish friend. They both stood there grinning at me, their eyes darting from my profusely blushing face to my genitals, to the panties, and back up again.

“Doesn’t she look adorable?” Brenda chirped.

I instinctively reached to cover myself again.

“Uh, uh uh,” Becky admonished, wagging a finger. “No touching your little clitty.”

The diabolical girls giggled freely as I slumped my shoulders over the latest disparagement.

“Clasp your hands behind your head,” Brenda ordered. “That way you won’t be tempted to play with that little thing.”

I slowly obeyed, lacing my fingers behind my head. My smooth, bare underarms were now on full display—another humiliating detail the girls weren’t going to ignore. Brenda slinked up beside me and ran her fingers up my side, then softly strummed my hairless armpit. “So smooth,” she cooed. “So charming.” I flinched, bringing my elbow down, which made her laugh even harder. She circled me slowly, eyes roaming over every inch of me. “Hey Beck,” she called. “Come check out Blondie’s buns—they’re almost as red as his face.”

Becky eagerly joined in. “Oh, yes,” she agreed, rubbing my cheek gently. “And feel how warm they are.” Now both girls had their hands on me, rubbing and stroking and making smug commentary the whole time.

“And check out his legs,” Brenda added, running a hand up my thigh. “Just look how smooth his pretty legs are.”

Two sets of hands stroked my legs. I winced yet again as I continued to endure the mockery from the relentless twosome. They were having the time of their lives, and all I could do was stand there helplessly, catering to their whims as their little plaything.


The Guests Arrive

The sound of the doorbell momentarily interrupted their fun. “I’ll get it,” Brenda chirped, already halfway to the door. She turned back with a wicked grin. “Looks like your company’s starting to arrive, sweetheart. I think you’re going to make quite an impression tonight.” She giggled to herself and disappeared into the hallway, leaving me alone with my devilish sister.

“Isn’t this fun, Blondie?” Becky asked as she looked intently at me. Without waiting for an answer that wasn’t forthcoming anyway, she knelt and slid the panties up snugly before giving the waistband a playful snap against my belly. She adjusted the lace trim with care, then stood back, grinning. “Too precious,” she cooed. “Absolutely precious.” Taking my hand, she led me toward the mirror. “Come see, Blondie. You’ll just love it.”

I didn’t love it. I stared at the figure in the mirror in disbelief. With my youngish face, hairless body, flat chest, and lacy panties hugging my hips, I could have passed for a prepubescent twelve-year-old girl with a boyish haircut. Becky, naturally, was all smiles.

Brenda poked her head in. “Joanna and... oh my gosh, how adorable!” she gasped, her eyes widening as she took me in. "Joanna and Marcia are here. Want me to bring them in?”

“No,” Becky replied. “Just keep them company out in the living room. There’s beer and Prosecco in the fridge—help yourselves. We’re almost ready. And tell them we have a surprise for them.” Again they both giggled as Brenda left the bedroom.

Becky turned back to me. “Okay, my dear brother—or should I say ‘sister?’ We’ve got to find you something else to wear. You can’t meet your adoring admirers in just your panties, you little slut.”

She laughed, clearly amused with herself, as I stood transfixed at the mirror, dread creeping in as I wondered what fresh humiliation she was about to dream up.

The doorbell rang again. “Oh, that must be Cheryl and Julie,” Becky announced. “You remember Julie, Blondie. She was the salesgirl who was so helpful at Victoria’s Secret during our little trip to the mall.”

How could I possibly forget?

I remained silent and was now downright grim. Becky continued to tease me. “I know she’ll love to see you in your pretty panties.”

I closed my eyes in anguish. Now there would be six—count ‘em, six girls to harass me.


Dressed for a Slumber Party

Becky slid open another drawer and pulled out a long, pink nylon nightgown. “Here we go, pumpkin. You’re going to look just gorgeous in this,” she said, holding it up in front of me. She slipped it over my head, and we both watched in the mirror as the hem floated down my body, settling just above my ankles. She adjusted the delicate spaghetti straps on my shoulders and clasped her hands in delight. “Oh! A perfect fit! You look so pretty in pink!”

I looked desolately at my reflection. My cheeks matched the color of the nightgown. “Oh, God, Becky, please... don’t make me go out there like this!” I could feel the tears welling up in my eyes as I pleaded desperately. “I can’t do this—I promise I’ll do anything. I’ll clean your room for the rest of my life, anything! PLEASE don’t make me go out there!”

With her response it struck me right then that she might be the devil incarnate. “I can have you clean my room anytime I want, regardless,” was her icy reply. “Now let’s go. We’ve kept your guests waiting long enough.” She took my hand and pulled me toward the door. I resisted. “Do you want your bare ass spanked in front of all those girls? Do you?" I stopped resisting.

"You should be thankful that I was able to find such a pretty nightie for you," she added, smoothing my hair. "You’re the only one properly dressed for a slumber party. Now be a good girl, and let’s go greet your guests. And I expect your full cooperation for the rest of the night. Do I make myself clear?”

I stared at the carpet, my face burning with shame.

“I said, ‘Do I make myself clear?’”

“Yes,” I whispered.

Becky smiled in satisfaction at my submission. “Good,” she said, patting my cheek. “Now let’s go introduce everyone to my darling new girlfriend. Oh, this is going to be so much fun!"”

While Becky giggled with delight, I took a deep breath and let her lead me down the hallway, dreading every step toward the sound of the voices waiting in the living room..
Last edited by Blondie on Wed Mar 25, 2026 1:02 am, edited 4 times in total.
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Roosevelt Humiliations, Chapter 19

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Chapter 19: The Slumber Party Begins

A Reprimand from Becky

My anxiety was cresting as Becky led me by the hand down the hallway. With every step, the silky hem of the pink nightgown fluttered against my ankles—a reminder of just how far I'd fallen. The nylon material caressed my freshly shaven legs, sending a shiver up my spine that had nothing to do with the temperature. I glanced down at my smooth, hairless arms and winced. There was no denying it—Becky and Brenda's attempts to sissify me had made an impression.

The sound of girlish chatter and laughter grew louder as we approached the clearing to the living room. I stopped in my tracks, extremely reluctant to continue. The right strap of the nightgown slipped off my shoulder, and I reached up to fix it. Becky was not pleased with my dawdling.

“I’m starting to lose patience with you, Blondie,” she warned, her voice unmistakably firm. “Look at me.”

I lifted my eyes to meet hers. She was inches from my face. She wore a stern expression, but her eyes were dancing with amusement. She was reveling in her power over me, and in my humiliation.

Raising a finger and pointing it directly at my nose, she said, “This is your last warning, Blondie." Her voice had risen, and the banter in the living room died instantly. "Don’t make me put you over my knee and spank you in front of everyone. And trust me, I will lift your nightgown and yank your panties down if you make me go there. Is that what you want?”

There was an audible gasp from the living room, followed by a wave of giggles. Apparently, the peanut gallery was very tuned in. I shook my head quickly, my face burning. “No,” I mumbled.

She gave a satisfied nod. “Alright then. Let’s go entertain our guests.”


Greeting the Guests

As I was ushered into the living room—or, more accurately, the lion’s den—I was greeted by a chorus of squeals and delighted shrieks. Becky led me to the center of the room and released my hand, stepping away and leaving me standing alone, to be ogled by the entertained crowd. I stared at the floor, cheeks flaming, as the laughter built around me. I felt like an exhibit. The girls were giddy, feeding off my shame as I stood there, utterly humiliated.

Finally, Becky and Brenda flanked me, guiding me toward the large, L-shaped couch. There were scattered beer cans, an open bottle of Prosecco, and way too many eyes on me.

“Come, come, Blondie dear,” Becky said, “Don’t be rude. Say hello to our guests.”

I still hadn’t looked up, but I could feel the presence of someone unfamiliar at the far end of the couch. Becky started the introductions at the other side. “You remember Cheryl, don’t you, Blondie?”

Cheryl extended her hand, practically beaming. “It’s a pleasure to see you again, Blondie,” she said with a grin. “That’s a lovely nightgown.”

I stayed silent, which earned me a quick scolding. “I told you not to be rude,” Becky said, grabbing my chin between her fingers and turning my head toward hers. “Now thank Cheryl for her nice compliment.”

“Thank you, Cheryl,” I managed, voice barely audible. Cheryl smiled and a couple of the girls snickered.

Becky led me to the next girl, and it became apparent that part of my humiliation would be to formally greet each of the guests. “Say hello to your good friend Marcia,” she instructed.

“Hi, Marcia,” I said robotically.

Marcia stood and planted a loud, wet kiss on my warm cheek. “Hello, Blondie! I’m so glad you could join us.”

There was silence, so I felt compelled to respond, to avoid another reprimand.

“Thank you,” I squeaked. This only brought on more giggling from the amused guests. Somehow my face flushed brighter.

I felt Brenda tug on my right elbow, guiding me to the next guest. Joanna was waiting with a wide, wicked grin. Becky nudged me with her elbow, prompting me to speak.

“Hi, Joanna,” I mumbled. She just kept smiling, saying nothing. Becky’s elbow jabbed me again. I had no idea what I was supposed to say, but I knew silence wasn’t an option. “I’m... I'm glad you could make it,” I blurted. There was laughter all around. Joanna continued to torment me by eyeing me up and down with the same shit-eating grin on her face. I squirmed under her gaze. “How have you been?” I added, immediately feeling ridiculous.

That did it. Joanna burst into full-on laughter, triggering another round from the rest of the girls. My face burned.

“Oh, Blondie,” she managed between gasps of laughter, “we are going to have so much fun with you tonight!” I cringed, knowing this was all too true.

Then came Julie, the salesgirl from Victoria’s Secret. I noticed the girl seated next to her and immediately felt a fresh wave of unease. She looked like she was about eleven or twelve years old. Being paraded like this was bad enough, but somehow being humiliated in front of a much younger girl made everything feel significantly worse.

But I wasn’t given time to dwell. Becky turned my attention to the salesgirl. “I know you remember Julie,” she said.

How could I not? That infamous mall visit left an indelible impression on me.

“Good evening, Blondie,” Julie said with a smile, extending her hand. “So nice to see you again. I must say, you’ve taken to girls’ clothes quite nicely! I don’t recognize this piece, though—have you been shopping somewhere other than my store?”

I fumbled for an answer. “Uh, I think this is Becky’s,” I responded weakly.

Julie gave a playful shrug and patted a "VS" tote bag at her feet. "No worries. I brought some fresh samples for you to try on. Maybe you can model them for us later?"

I didn’t answer right away—and Becky’s elbow jabbed me harder this time. “Yes, uh... thanks,” I mumbled.

Before I could retreat, she turned to the unfamiliar girl beside her. “Blondie, meet my sister, Felicity. Felicity, this is the famous Blondie.”

“Nice to meet you,” I forced out as I shook her hand.

The little girl stood up and offered her hand, smiling just a little too brightly. “No, it really is my pleasure, Blondie,” she said. “My sister’s told me all about you, and I’ve just been dying to meet you.” I sensed a degree of precocity in the girl that put me on edge. I had a sinking feeling this girl would be trouble.

Julie grinned. “It’s Felicity’s thirteenth birthday today. Brenda called me earlier and told me that you would be entertaining us tonight, and when I told Felicity, she... well, let's just say it might be the most excited I've ever seen her. Doesn’t that make you feel special, Blondie?” Everyone giggled with delight and waited for my answer.

“Very special,” I muttered sarcastically through gritted teeth. The girls again laughed, taking pleasure in my misery.

“Wish her a happy birthday,” chirped Becky.

“Happy birthday,” I said, not even trying to sound enthusiastic.

“Why thank you, Blondie. You’re such a sweetheart,” Felicity said.

I remember thinking, once again, that this girl really was going to be trouble.


Staving Off Exposure

Becky clapped her hands. “Who needs a beer?” That effectively ended the formal greetings. As she disappeared into the kitchen, I was left standing awkwardly—until Joanna tugged me down between her and Marcia. There was no question as to who the center of attention would be.

“Oooh, Blondie,” Marcia purred, running her fingers along my bare arm. “Your arms are so nice and smooth. Joanna, feel this. It’s so smooth and silky.”

Joanna leaned in eagerly. “You’re right, Marcia, soft as velvet. Are you like this everywhere?” She reached for the hem of the nightgown, but I managed to fend her off. “Oh, you’re such the bashful one, Princess,” she giggled. “Maybe later we can see if you’re this smooth all over.” I cringed, both at the usage of “Princess” and the thought of what may lay in store for me.

Again she stroked my arm while planting a playful kiss on my cheek. “Whatcha sportin’ down below?” Joanna was on a roll now, and there was no stopping her. She began feeling around my waist, her fingers searching for the waistband of my underwear. “Let me guess—you’re wearing a pretty pair of panties, aren’t you?” Indeed, she was fiddling with the elastic of the panties (notice how I can’t even bring myself to call them my panties?) through the nightgown. I squirmed, trying to wriggle out of reach. Joanna’s grin widened, and she raised her voice.

“I think he’s wearing panties, girls! Are you, Princess? Are you wearing panties? Come on, little sissy-boy, you can tell Auntie Joanna—are you wearing your pretty little panties under there?” Again she made a move to lift the nightgown, and again I fought her off.

“Please, just leave me alone!” I begged. I was on the verge of tears but managed to hold them back. I certainly didn’t need to give them more ammunition to tease me with.

Brenda interceded, and it was to my detriment. “Why don’t you tell us all what you’re wearing under your nightgown, sweetheart.”

I knew better than to challenge Brenda. There were a few moments of silence, as I had considerable trouble vocalizing the word. “P-panties,” I finally said, very softly.

“I’m sorry, what was that? Speak up, dear, so we can all hear you,” Brenda said.

“Panties!” I screamed out, almost defiantly. Laughter was abounding.

Joanna pounced on the moment. “What color are they, Princess?”

I fidgeted nervously. “Pink,” I mumbled.

“Ooh, how darling," teased Joanna. "Do you like wearing your pretty pink panties? Hm? Do they make you excited?” She tried to reach for my penis, but I pulled her hand away. Everyone was laughing, rollicking at Joanna’s taunting. “Well, do you, Princess? Do you get off on wearing your sissy panties?”

“Please, no...”

“Oh, you say no, but you mean yes, don’t you? Say it. Say, ‘I love wearing my pretty pink panties. It makes my little clitty all excited.’ Say it, Princess.” The giggling was building toward a crescendo.

Cheryl was nearly in tears from laughing. “Oh, Joanna, you’re wicked!”

I knew there would be no letup until I relented. I took a deep breath and uttered the painful words. “I love wearing my pink panties.” That was all I could muster, and it didn’t satisfy my tormentor.

“They’re ‘pretty’ pink panties, Princess," persisted Joanna. "Say it—and tell us why you love wearing them.”

I really wanted to cry now. I closed my eyes tightly and said in a quivering voice, “I love wearing my pretty... my pretty pink panties... because it makes my c-clitty... my little clitty... all excited.”

The laughter was more boisterous than ever, and my cheeks couldn’t have been any hotter.


Led Away by Julie and Felicity

Once the laughter died down, Julie stood and grabbed her bag. "Come with me, Blondie. Let’s get you into something a little more comfortable."

I looked up at Becky with a pleading look on my face, somehow hoping she would intervene.

“What are you looking at me for, girlfriend?” she teased. “You heard Julie. Scoot!”

As I stood up, I felt a pinch on my rear end. I brushed Joanna’s hand away, catching a glimpse of her devilish grin as I did.

“Felicity, would you like to join us?” Julie asked.

“Indubitably,” Felicity chirped, springing to her feet—all too enthusiastically, from my perspective.

Julie laughed. “I assume that means ‘yes.’ ”

Julie looped an arm around my shoulder, guiding me toward the bedroom, the eager Felicity close behind. “Isn’t she just too smart for her own good, Blondie?” I didn’t answer. I was hardly in the mood to engage in dialogue.

When we reached the hallway, Julie squeezed me closer to her and put her mouth to my left ear, tickling it as she spoke. “Don’t worry, sweetie, we’ll be gentle,” she said in a soft, throaty voice.

The salesgirl and her precocious little sister giggled heartily as they led me to Becky's bedroom, where further humiliation undoubtedly loomed.
Last edited by Blondie on Wed Mar 25, 2026 6:10 am, edited 5 times in total.
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Roosevelt Humiliations, Chapter 20

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Chapter 20: Petticoated

A Peek Inside the Panties

Julie led me down the hallway into Becky’s bedroom, her right arm draped casually over my bare shoulders and a large Victoria’s Secret tote swinging from her other hand. Trailing close behind was Felicity, her spunky little sister, eyes alight with mischief.

Once inside, Julie released me and crossed to the bed, dropping the bag onto the quilt. I remained where I was, rooted to the spot, Felicity lingered in front of me, grinning unabashedly, drinking in every second of my discomfort.

“Is this where we get to make Blondie get naked?” she asked eagerly, her gaze fixed on my flushed face.

Julie let out a delighted laugh as she rummaged through her bag. “You really are something, aren’t you, little sister? You turn thirteen, have your first beer, and now you want to see your first naked boy.” She paused, enjoying the moment. “Hang in there, birthday girl—you’ll get your chance.”

She continued digging through the tote. “Let’s see now... what do we have in here for our little girlfriend?”

I turned my head slowly toward the bed, already dreading what I might see. My fears were confirmed when she said, “Ah, here we go—he’ll look just divine in this,” and pulled out a little girl’s party dress. She held it up. It was baby blue, with a short, flared skirt and puffy sleeves. My eyes widened, my mouth dropped open, and horror flooded through me.

“Oh please,” I pleaded. My body language spoke volumes as I folded my arms across my chest and slumped my shoulders. “I can’t wear that out there. Please...”

“Nonsense, sweetie,” Julie answered cheerfully. “Think about it—you’re at a girl’s party, you’re the center of attention, you look like a little girl... it’s only fitting you should wear a festive little girl’s party dress.”

She draped it on a hanger and hooked it over the bedpost before turning back to the bag. I couldn’t tear my gaze from it, awestruck by the sheer humiliation it represented—until Julie’s next words jolted me back.

“Felicity, would you like to help Blondie out of his nightie so we can get him ready?”

She studied us closely. One of us was a picture of utter anguish, while the other was practically glowing with delight.

“You betcha!” Felicity squealed, stepping forward. She took hold of the nightgown’s spaghetti straps, sliding them down my shoulders. I recoiled instinctively, crossing my arms tightly over my chest.

“Don’t make me come over there, Blondie,” Julie warned, “if you know what’s good for you...”

“I've got this,” Felicity cut in confidently, wagging her finger in my face. “Okay, Blondie—either you lower your arms and cooperate right now, or I call the girls in here and we'll strip off your nightgown, pull down your panties, and take turns putting you over our knees for a spanking you’ll never forget. Then you’ll model your pretty new party dress for us anyway. So it’s your choice. Either way”—she pointed at the dress—“you’ll be wearing that by the time we’re done. Now... which way would you like it?”

The precocious little thing was a monster. I glanced quickly at Julie, who was beaming at her sister’s performance, then I bowed my head and lowered my arms in surrender.

“That’s more like it,” Felicity chirped, clearly pleased with herself. She gently slid the straps free of my arms and stepped back to watch the natural descent of the nightgown as it pooled around my ankles. Her fingertips flew to her lips as she squealed with delighted disbelief at the sight of me—smooth legs and all, trembling, and wearing nothing but a pair of pink panties.

“Oh, my goodness!” she gasped, utterly tickled.

I could do nothing but cover myself as best I could, cheeks burning with shame.

“Well, well, what have we here?” Julie asked rhetorically, approaching with a devilish grin.

Until then, she’d been just a very interested spectator—now she was ready to join in. Kneeling, she lifted my feet one at a time, freeing me from the nightgown.

“My, my, look at these pretty legs,” she said, brushing her fingers lightly along my calf. “Felicity, come feel how smooth his legs are.”

Of course, the little fiend needed no second invitation. “Ooh, you’re right, Julie,” she cooed, caressing my other leg. “So smooth and pretty—like silk.”

I wished I could simply evaporate on the spot.

Julie rose and ran her hands over the seat of my panties. “And such darling panties, too. Do you like your panties, Blondie?” she teased.

I stayed silent, head down, staring miserably at the floor. Raising her arms, she interlaced her fingers behind her head, elbows wide.

“Go like this, Blondie. I want to see something.”

I hesitated, but I knew there was no use resisting. I complied. Julie giggled. “Just as I thought—not a hair anywhere,” she said, inspecting my smooth underarms. I stood there, helpless, and exposed—just the way they liked me.

“Stand up straight, and don’t you dare move your hands—I want to see one more thing,” Julie warned, a devilish glint in her eye. To my horror, she hooked her finger into the front of the panties and pulled outward, peering inside. Her smirk grew wider. “Well, at least you’ve got some hair,” she teased, before letting the elastic snap back. She turned, chuckling, and sauntered back toward the bed.

“I wanna see, I wanna see!” Felicity chimed in gleefully, sounding like an eight-year-old determined to get her way.

I instinctively drew back my hips as she reached for the elastic. The idea the thirteen-year-old inspecting my most private parts against my will was just too much.

“Blondie?” she warned with an admonishing look.

I straightened up and reluctantly submitted to the mischievous sprite. Eyes squeezed shut, I braced myself as the elastic stretched away again. Her hair tickled my stomach as she leaned in. Though my eyes stayed closed, the image of her staring down my panties burned in my mind.

After what felt like an agonizing eternity, the elastic snapped back into place.

“Well, little sister?” Julie asked, clearly enjoying the show.

Felicity beamed. “It looks just like Joey’s, except Joey has no hair.”

Julie laughed boisterously and approached me, locking eyes as she spoke. “In case you’re wondering, Blondie, Joey’s our little brother. He’s ten.” Both girls burst into uproarious laughter while I blushed crimson.

“I assume it’s supposed to get bigger as boys get older. Right, Blondie?”

Felicity directed the question at me, but I didn’t answer. She knew she’d struck a nerve and milked it for all it was worth.

“How old are you, Blondie?” she pressed, staring me down until I gave in, hoping to speed the interaction to a conclusion.

“Sixteen,” I whispered, averting my eyes.

“Well, except for the hair, you look like you’re ten, judging by what’s inside your panties.”

Both girls laughed again as I turned yet another shade of red.


The Petticoat

“Okay,” Julie said, clapping her hands together. “Time to finish getting you dressed.” She again started sorting through her bag of tricks. “Ah, here we are,” she said with a look of satisfaction.

She pulled out a medium-sized, bluish nylon bag, tied at the top. My stomach twisted as she loosened the string. She continued teasing me as she reached into the bag.

“Do you know what it means to be ‘petticoated,’ Blondie?” she asked. I didn’t answer. “It’s an old-fashioned term for putting a boy in girls’ clothes—usually not by his own choice." She pulled out something white, fluffy, and terrifying. “In this case, you’re about to be petticoated in the literal sense.”

Much to my chagrin, the grinning Julie pulled the garment free from the nylon bag, and a very frilly petticoat came into view, its skirt having expanded considerably after being removed from its confinement. She held it up, and upon noticing my look of consternation, she waltzed over to me and cupped my chin in her hand.

“Don’t worry, sweetie," she teased. "You’ll look adorable,” Julie cooed, pinching my cheek before handing the garment to her sister. “Felicity, darling, would you like to do the honors?”

“Oh, yes please!” Felicity replied gleefully. She lifted it over my head and tugged it down, adjusting the shoulder straps and fluffing out the skirt. She stepped back and looked me up and down. “Oh my gosh! You must come see, Blondie!”

She grabbed my hand and led me to the full-length mirror. What stared back at me was a very red-faced sixteen-year-old boy adorned in a frilly, fluffy, short white petticoat that flared out like an umbrella, short and poofy and feminine. I stared at myself in disbelief.

Julie appeared at my other side. “Oh, he looks adorable,” she purred. “What do you think, Blondie, are you getting in touch with your feminine side?” I shook my head, eyes wide with disbelief. They just giggled.

“Come, my petticoated one,” Julie teased, leading me back to the bed. “Let’s finish your outfit.” The petticoat made an audible swish-swish with every step, adding to my mortification. Julie patted the mattress. "Sit."

I did—and instantly regretted it. The skirt flared up as I sat, prompting a delighted squeal from Felicity as she crouched down, trying to peek underneath. Mortified, I clamped my knees together and pressed the petticoat down with both hands—realizing to my disgust I had just done exactly what a little girl would’ve done.

Felicity noticed. “What’s the matter, Blondie?” she teased. “Don’t want me to see your panties?”

Julie laughed and plopped beside me. “Let’s finish dressing our little girlfriend.”

My humiliation deepened as they continued treating me like a helpless little girl who couldn’t even dress herself. Julie lifted my foot and rested it on her thigh, carefully slipping a frilly white anklet into place.

“Just like the ones Becky and Brenda had you wear at the mall, remember?” she said. “You should feel right at home in these, sweetheart."

"Here, Felicity,” she said as she handed the other sock to her sister. “Do me a favor and put this on our little friend while I get her shoes."

As Felicity worked the second anklet onto my foot, Julie produced a pair of shiny black patent leather shoes with little buckles. She glanced up, catching the look of despair on my face.

“What’s the matter, Princess?” she teased. “Don’t you like your Mary Janes? They’re brand new. Becky told me your size, and it looks like they're a perfect fit.”

She slipped one onto my foot, fastening it snugly, then handed the other to Felicity, who eagerly followed suit. Once both shoes were secured, Felicity grabbed my hand again.

“Let’s go see, Blondie!” she squealed merrily.

Back at the mirror, a distraught, red-faced boy in a flared white petticoat stared back at me, only this time he was wearing frilly anklets and glossy little girls' shoes.

“Stay right here while I go get your dress,” ordered Felicity.


The Little Girls’ Party Dress

Before I could recover, she was already sliding the baby-blue party dress over my head. I watched in disbelief as the hem dropped, settling just an inch above the petticoat. Julie zipped me up from behind while Felicity fussed with the sleeves and hem.

Then came the pièce de résistance—Julie pinned a massive baby-blue bow atop my head, adjusting it with meticulous care, tilting it this way and that until it stood just right. I wanted to sink through the floor.

“Ohhh, Blondie,” Julie sang, stepping back to admire her work. “You look absolutely angelic!”

Both girls busied themselves adjusting the dress to their liking, while I stood utterly miserable, taking in my latest humiliation. But they weren’t finished.

“Oh! Wait—I almost forgot!” Julie exclaimed, spinning toward her bag. “Felicity, would you be a dear and help Blondie out of her grown-up panties? I’ve got something much more appropriate for a little girl.”


Ruffled Panties

Felicity was all too happy to comply. I felt a flush of embarrassment as she knelt and reached up my dress (Oh my God, I just called it my dress—I mean the dress) and in one swift motion, she tugged the panties down to my ankles. I flinched at the invasion, then again when she slipped beneath the petticoat to peek. She looked up, grinning, while I burned red with shame.

A new pair of panties dangled above me, held aloft by Julie. They were absurdly frilly, with ruffles across the rear. “Time for your frou-frous, little girl,” giggled Julie, kneeling before me. I lifted my feet obediently, complicit in my own humiliation—what choice did I have?—and watched as she slid the girlish lace up my legs with excruciating slowness until they were snug in place. When she finished, she gave a cheeky squeeze between my legs, making me jump and let out a high-pitched, humiliating squeal that had both girls howling with delight.

Julie spun me around so my back faced the mirror. “Turn your head and take a look, sweetie,” she said. I did, and to my dismay, layers of ruffles peeked from beneath the petticoat. I tried to tug the hem down, but it sprang just right back into place.

“They’re going to love your pretty frou-frous, Princess,” Julie grinned.

I winced, imagining the view every time I walked—or worse, if I dared to bend over. A tear slipped down my cheek despite my best effort to hold it back. Julie stepped close, feigning compassion, and gently wiped it away with her thumb.

“I think she’s shy about showing off her pretty new outfit, Felicity. Don’t cry, little girl,” she said. “They’re going to love your pretty dress. You're going to be a big hit, I promise.”

I embarrassed myself even more, as the harder I fought the tears, the more they came. “Please... don’t make me go out there like this,” I begged, my voice cracking.

Julie just smiled, took my hand, and said, “Now, now. The best thing for you is to go out and play with your friends. Felicity, take her other hand.”

“No, please!” I whimpered. But the door opened, and they pulled me forward, petticoat swishing, guiding their reluctant little doll toward the party. “Please, no!” I begged again, resisting, desperate not to cross the threshold.


A Spanking

“Alright, that does it—I’ve had just about enough of you, young lady!” Julie snapped, pretending to be truly upset. Looking back, I’m pretty sure she was just hunting for an excuse to spank me. She turned to the dresser, picked up a hairbrush, and tapped it once against her palm. “Pull up her petticoat, Felicity.”

“No, please!” I yelped in protest—but Felicity was already behind me, grinning as she flipped the fluffy white layers upward.

“Pull down her panties,” Julie ordered.

“No! Nooo!” I pleaded, but my protests only seemed to egg them on. Felicity hooked her fingers into the waistband and tugged them down to my knees, then held the petticoat bunched firmly against my back.

I knew resisting any longer would only make things worse. Before I could even catch my breath—Whap! Whap! Whap! Whap! Whap! Whap! Six sharp blows from the back of the hairbrush smacked against my bare ass, three on each cheek. The pain took a moment to register, but when it did—man, I'm here to tell you... it radiated right down to the bone.

“Ow! Ow! Ow! Ow!” I squealed, hopping in place while cradling my butt cheeks with both hands. The girls burst into peals of laughter. I must have looked completely ridiculous—bouncing up and down with frilly panties hanging at my knees while the petticoat and dress bobbed up and down.

When the pain finally began to fade, I pulled the panties back up with shaky fingers. Julie wiped tears of laughter from her eyes.

“Oh God, Blondie, that was too funny. I’m sorry the others missed it.” She leaned in. “Now, are you ready to join the party, or do we need to discipline you some more?” There was a pause. “Answer me, Blondie.”

“I... I’m ready,” I replied subserviently.

“That’s a good girl. Now let’s get you fixed up—your bow’s gone crooked, and you’ve wrinkled your pretty dress.”

Like a doting big sister, Julie gently fluffed the skirt, straightened the anklets, and adjusted the baby-blue bow in my hair. She used the hairbrush to smooth my fairly short hair, and when she spotted a stray tear, she brushed it from my cheek with her fingertip.

“There, there, sweetheart, everything will be okay,” she teased. “Soon everyone will get to see just how precious you look.”

That didn’t help.

“Let’s not keep them waiting any longer, sugar pie.”

Julie took one hand, Felicity the other, and this time I didn’t resist as they led me down the hallway. When we entered the living room—well, I’m sure you can imagine the uproar. The shrieks of surprise and delight were almost deafening.

“Oh my God!”

“Look at him!”

“He’s such a sissy!”

“Oh, shit, this is too much!”

“Look at that pretty little dress!”

“And that petticoat!”

"And those legs! Oh, my goodness!"

"Yes! So smooth!

"And girly!"

“How adorable!”

“Aw, she’s been crying.”

I can’t really remember who said what, but the scornful comments went on for a while as I stood alone in the middle of the living room, so humiliated that I just stood transfixed, face throbbing with embarrassment, unable to move a muscle.

After the noise finally died down somewhat, the girls really started having their fun...

* * * * * *

I’ve gone on far longer than I intended—and reliving it is unpleasant enough—so I'm not going to go into every detail of what happened over the next hour or so. But here’s a quick rundown of what I was made to do while dolled up in that ridiculous party dress—and yes, threats of a bare-assed spanking got me moving when I hesitated. I was made to:

—Curtsy to each girl, lifting the dress and petticoat high enough to flash my panties each time.

—Play “Patty-Cake” with Marcia, who insisted on the full routine. Twice.

—Do the entire “Hokey Pokey,” with my skirt bouncing and swaying with every turn.

—Perform “I’m a Little Teapot.”

—Stand in the center of the room holding up the petticoat while the giggling girls made mocking comments on the panties and my “pretty” legs.

I think you get the picture. It was total, unrelenting humiliation—and they enjoyed every second of it.

Unfortunately, the night was still young, and the sadistic seven had more degradations in store for me.

Next time around, when I gather up the courage to give another account, I’ll tell you how I was rendered naked by the precocious, demonic Felicity.

I’ll tell you this much right now: I would have gladly taken another round with the petticoat over what came next.
Last edited by Blondie on Sun Mar 29, 2026 11:14 pm, edited 7 times in total.
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Roosevelt Humiliations, Chapter 21

Post by Blondie »

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Chapter 21: Felicity

Alone with a Little Devil

While I was being put through my paces in the wretched party dress, I noticed with a bit of trepidation that Julie was reaching for the dreaded bag again.

“Come with me, Blondie,” Julie said, casually heading for the hallway that led to Becky’s bedroom. Her voice was cheerful, almost singsong. “Care to join us again, Felicity?”

I winced. My humiliation was bad enough, but somehow this precocious thirteen-year-old’s involvement added an extra edge to it.

“Yes, I’d love to,” the little menace chirped. But then, she tilted her head with an expression that had “trouble” written all over it. “Actually, Julie... could I ask for a little favor?”

Julie paused, looking curious. “What’s that?”

“Um... if you could offer me this boon for my birthday... I’d really, really like to take Blondie back there by myself. You know... so we can get to know each other better,” she teased while staring at me with a predatory grin.

Julie threw her head back and laughed. “Why, you little devil, you! Well, sure, you can have your little birthday ‘boon,’ as you called it. I don’t know where you come up with these words," she said, shaking her head. "And I think Blondie would love to have you all to himself. Wouldn’t you, Blondie?”

I just stood there, a picture of wretchedness, while the room erupted in giggles.

“Oh yes, Blondie is just delighted. Now toddle along, you two. And take your time, enjoy yourselves.” More giggles. “And Blondie, I’m warning you: We’d better not hear a word about you being uncooperative. It’s Felicity’s special night, and you’re going to do anything she asks. Got it?” I gulped and gave a small, miserable nod. “Look at that face,” Julie grinned. “He’s thrilled. Off you go!”

“Come with me, Blondie,” Felicity said eagerly. She snatched the bag from Julie with one hand and gripped mine with the other, leading me down the hallway.

The next hour would prove to be nearly unbearable.

* * * * * *

Felicity wasted no time once we entered the bedroom. “Sit,” she commanded, patting the bed next to the dreaded bag. “Let’s get you undressed.”

I obeyed with a heavy sense of extreme apprehension. My feet dangled above the carpet, making it easy for her to kneel and start on my shoes.

“Isn’t this great, Blondie?” she chirped, fiddling with the buckles. “Just the two of us? It’ll really give us a chance to get to know each other, don’t you think?”

I remained silent. The last thing I felt like doing during this godawful experience was engaging in conversation with this fiend. But she had other ideas. She stood up and pointed her index finger at my face.

“Now listen, Blondie. When I speak to you, I expect the courtesy of a response. In case you haven’t noticed, there are two of us in this room, and I don’t plan on carrying on a monologue.”

Oh, this is really going to be hell.

“Do you understand me?”

“Yes, I understand,” I said sullenly without looking at her.

She knelt again, moving from my shoes to my socks. She picked up right where she left off. “So, tell me a little bit about yourself.” Both shoes were off now, and she deliberately began rolling one of the lacy anklets down my foot.

“Uh... uh... what do you want to know?” I couldn’t believe I had to carry on the dialogue while being methodically stripped by a girl three years my junior.

“Oh, you know, what are your likes? Your dislikes? Pretty soon I’m going to be quite familiar with what you’ve got on the outside. I’d like to get to know you on the inside.” She giggled to herself, tossing a sock aside.

I was miserable. I pushed myself to do her bidding. “Um, I like sports. I like to play basket... please, I can’t do this.”

She persisted. “What kind of music do you like?” I was barefoot now, and she took my hand to pull me up. “Stand up, let’s get this dress off.” I stood up and felt her hand working the zipper down from the back of my neck. “Answer me, Blondie.”

“I like... rock and roll.”

“Oh, me, too! See, we have something in common. Do you like to dance?” The zipper was all the way down. “Arms up.” I raised my arms above my head, and she slowly started pulling the dress up. “Keep talking to me, Blondie. Do you like to dance?”

“No, not really,” I replied despondently. I really didn't like where she was going with this.

“Aww, that’s too bad. I’d love to see you dance for us in one of Julie’s outfits. It’s my birthday—do you think you can dance for me tonight?” The prospect horrified me, but I had to be cooperative.

“We’ll see,” I said.

“Oh, that will be a treat," she said while clapping her hands together. "I’ll bet you’re a good dancer.” She paused and took in the wretched expression on my face, which only egged her on. "Maybe we can take all your clothes off and you can perform a naked dance for me," she said excitedly.

I couldn't think of anything more humiliating. "No, please..." I said, my voice trailing off.

"Oh, Blondie, I'm going to have so much fun with you," she said. "This is the best birthday present ever!"

She pulled the dress completely off and left me standing there in just the petticoat, face burning. She stepped in front of me and gazed at me, grinning widely. “How delightful. You really do blush like a little girl.” Putting both hands on my shoulders, she eased the straps of the petticoat down my biceps, starting its leisurely descent. “Tell me about your experience with my sister in her store at the mall. I heard such delicious things.”

“What... what do you want to know?” I was stalling. I really didn’t want to relive that humiliation, especially under those circumstances.

“Everything,” she answered fervently. “I’ve heard the story from Julie, but it would mean so much more coming from you.”

The petticoat fell to my waist, leaving me bare-chested. Felicity knelt again, her eyes sparkling as she pulled the garment lower, exposing the frilly ruffles of the panties. She looked like she was having the time of her young life.

"Tell me!" she pressed.

“Um... well... um... they made me...”

Who made you?” she interrupted.

“B-Becky and Brenda... they made me go to Victoria’s Sec... please, you know the story.” The petticoat was bundled at my feet, its expanse of lace rising halfway up my shins. I folded both hands over the crotch of the panties, feeling my modesty being severely threatened.

“Continue!”

“Th-they made me try on... different stuff.” I had trouble continuing the charade.

She lifted one of my legs up and out of the petticoat. “Tell me more, sweetie. Tell me what they made you try on.”

“A t-teddy... then a bra and p-p...” I couldn’t say the word. At that moment, the petticoat was being pulled off my other leg, leaving me standing there in... yes, a pair of panties.

As Felicity stood up, she prodded me on. “Go ahead, you tried on a bra and...?” She tossed the petticoat aside and stood back, grinning wickedly at me.

“Panties,” I said, very quietly.

She clapped her hands. “Yes! Julie told me you looked quite darling. Just like you do now. She said your face was fire-engine red. Does your face feel as hot now as it did then, Blondie?” She was the devil in disguise.

“Yes,” I answered as I looked at the floor, shamefaced.

“Go like this.” She made two fists and put both hands on her hips, elbows pointing to the sides. I struck the pose. She circled me slowly, drinking it all in. “Oh my. Look at you. Just adorable. But...” She trailed a finger down my tummy, stopping at the waistband. “...these are going to have to come off, so you can model your next outfit.”

She reached for the waistband of the panties, studying me intently. She got the reaction she wished for as I instinctively retracted my hips, eliciting a knowing smile from her lips.

“Oh, I’m sorry, sweetheart. I forgot how much you love your pretty panties. Well, there’s no hurry. We’ll save it for later. For now, we need to find you something cute to wear.” She opened the bag and sorted through it. “You know, this is a slumber party, and you really should be dressed accordingly. Maybe a pair of pajamas is appropriate. We’ll call it a pajama party.” She held up a very feminine peach-colored pajama set. “Would you like to wear these, sweetie?”

I didn’t show much reaction—though, all things considered, it wouldn’t have been so bad. At least they offered a lot of coverage.

“They’re okay,” I replied.

“Or how about this?” She pulled out a scanty pink nylon babydoll and held it up to me. I observed uneasily that it would barely cover my genitals. Felicity sensed my apprehension; she was perceptive beyond her years. “I’ll let you decide, Blondie. The pajamas... or the babydoll? You pick.”

I didn’t hesitate. “The pajamas.”

I should have known better than to expect any compassion from the little demon. “Oh, you silly boy,” she laughed as she tossed the pajamas aside and lifted the babydoll high. “You’re quite the shy one, aren’t you? But we can’t have you hiding those pretty legs from the guests, now can we?” She clutched the babydoll to her chest and gave me a wink. “Now come here, sweetie. It’s time to take off your panties."


Taking Down the Panties

“Hmm, how shall we do this? Felicity mused, her eyes scanning me lasciviously. "Shall I take them down, or would you like to do it yourself?”

In retrospect, I should have just ripped the damn things off right on the spot, thus avoiding further anguish. But the idea of being naked in front of the young girl was more than I could stomach. Some desperate part of me still held out hope for mercy. “Please...” I begged, my voice barely audible.

“I get the distinct impression that you don’t want me to see you naked, Blondie.” Felicity glared at me with a menacing smile. I didn’t respond, eyes glued to the carpet. My silence only energized her more. “Why is that, Blondie?”

Again, I didn’t answer. That didn’t slow her down. She was thriving now, thoroughly enjoying my anguish.

“What’s the big deal? I’ve already looked down your panties and saw your little thingy, remember? I told you it looked just like my little brother Joey’s, except you have hair.” I was blushing crimson now, and she went in for the kill. “And the more you blush, the more fun I have. Why is that, Blondie?”

I snapped. “Because you’re a fucking bitch!” I screamed, the words out before I could stop them.

Her face remained impassive, but I knew I’d made a big mistake. “You’ll be sorry you said that, Blondie. I’ll deal with your punishment before we go back out there—but for now, I can tell you that if there are any more outbursts, then I’ll tell the girls you’re being uncooperative. Would you like me to do that, Blondie?”

“No,” I muttered.

Just then, the doorbell rang. I winced.

Oh, no. Not another guest!

Felicity didn’t miss the look of dismay on my face. “Oh boy, Blondie, it looks like you might have another visitor. We’d best get these panties off now and get you ready." She dragged a stool from the dresser to the center of the room. “Step up here, sweetie, so I won’t have to bend over when I pull your panties down.”

Feeling utterly defeated, I stepped up, facing her. My hands instinctively cupped the small bulge in the panties as she stood grinning, eye-level with my shame. Felicity grasped the hem on each side with her fingers, and held them there, teasing me. She looked up expectantly. “It’s time, Blondie. It’s the moment we’ve been waiting for. Isn’t this fun?” I had no answer. “I’m doing all the talking now, Blondie, and I don’t appreciate it. Now, be a good boy and ask me nicely to take down your panties.”

I nearly choked on the words, but somehow I got them out. “Would you... please take down the... my panties?”

She beamed. “Why certainly, sweetheart,” she replied with pleasure in her voice. “Would you kindly put your hands behind your head so I can do that for you?” I hesitated, then interlocked my fingers and raised my arms, leaving my torso exposed and utterly vulnerable.

My sense of dread was extreme. Felicity took a long, slow look at me, then smiled. She was ready to do the dirty deed. “Okay, here we go, are you ready? On three: One... two...” Then she stopped and stepped back.

“I just had a wonderful idea, Blondie. It’s my birthday, right?” I nodded warily. “And you’re about to be in your birthday suit, right?” Again I nodded, apprehensively preparing for whatever might be coming out of her mouth next. Her eyes gleamed. “Well then... it would be really special if you could sing ‘Happy Birthday’ to me while your panties are coming down. Will you do that for me, Blondie?” I groaned inwardly, but I nodded resignedly. I was past the point of resistance.

"Oh, goodie!" she squealed while clapping her hands with delight and giving an excited little bounce. I felt like I was submitting to a ten-year-old girl.

She poised her fingers on the hems of the panties again, looking up like a kid at Christmas. “Whenever you’re ready, Blondie...”

There was no sense in delaying the inevitable. I closed my eyes tight and began to sing.

♬“Happy birthday to you.”♬ I felt the panties begin their inexorable descent.

“Sing it slower!” she urged. She was really getting caught up in the moment.

♬“Happy birthday to you.”♬ The panties were now slipping past my penis. Felicity giggled with delight. It was all I could do to keep my hands on my head.

♬“Happy birthday, dear Felicity...”♬ The panties were at my knees, the point of no return. I opened my eyes to a squint and looked down at a girl who was nearly beside herself in youthful, jubilant ecstasy.

♬“Happy birthday to you.”♬

The panties pooled at my ankles. Felicity stepped back and fervently clapped her hands with glee. “Bravo, Blondie! Bravo!” she squealed with delight.

The door flew open. Becky stood there, her jaw literally dropping at the unusual sight. “Oh my GOD! Blondie, what is Felicity doing to you?!” she exclaimed. Then, when the scene kicked in for her, her hands were at her mouth, and she was overtaken by convulsive laughter.

I buckled forward, arms clamped over my crotch, my face burning hotter than a bonfire. Becky leaned against the doorframe for support, tears streaming down her face. Felicity, for her part, had a triumphant grin on her face, quite proud of herself for creating such a spectacle.

I couldn’t imagine being more embarrassed than I was at that moment.

When Becky finally caught her breath, she wiped her eyes and announced, “I just thought I’d let you know, Mitch is here, and he can’t wait to see you, Blondie." She paused to take in the horrified look on my face, then smiled and shot a grin at Felicity. “Take your time, birthday girl. Don’t let us spoil your fun."

She closed the door behind her, her laughter echoing down the hallway. Undoubtedly she was quite anxious to relay to her friends the scene she had just witnessed.

But I had much bigger concerns. I was, for all intents and purposes, naked and at the mercy of a girl who was cunning beyond her years—and seemed hell-bent on humiliating me by any means at her disposal.
Last edited by Blondie on Mon Mar 30, 2026 9:40 pm, edited 4 times in total.
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Roosevelt Humiliations, Chapter 22

Post by Blondie »

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Chapter 22: Denuded by a Thirteen-Year-Old

Naked on the Bed

Felicity grinned wickedly at me for a few seconds. I stood there on the stool, still bent over at the waist. Without a word, she lifted one of my legs, then the other, freeing the panties from my feet. I was now completely, undeniably naked, and at her mercy.

She dropped the panties on the floor and reached out for my hand. “Come, sweetie. Let’s chitchat over on the bed for a while.”

My stomach sank. My torture at the hands of this cruel little girl was going to carry on. I took her hand reluctantly, and she helped me down from the stool. My free hand remained firmly clutched over my groin as she led me to the bed. “Up we go,” she said cheerfully, climbing onto the mattress and pulling me with her. She positioned us with my back facing the door, and her front squarely toward me. I sat awkwardly with my legs tucked to the side, still guarding my modesty like my life depended on it. I had no idea what she had in store next—and I was pretty sure I didn't want to find out.

“Come on now, Blondie, let’s get comfortable.”

With a grin, she reached for my ankles and tugged. My legs were pulled forward, splaying apart on either side of her hips. She scooted closer, draping her legs over mine, effectively pinning me in place. Her clothed torso was now merely inches from my naked one.

She held out her hands. “Give me your hands,” she requested. Of course, it wasn’t a request. I hesitated, but I knew better than to resist. Slowly, I lifted my hands into hers. She gently guided them outward, placing my palms flat on the bedspread just beyond my knees. I was now fully exposed, which, of course, was her intent. I tried to pull my knees together, but her body was immovable. She looked between my legs and smiled, clearly pleased with the result.

"Tell me, Blondie, what's it like to be naked against your will in front of a thirteen-year-old girl?"

I had no answer. I turned my gaze downcast and fixed it on the floral pattern of the bedspread.

“I can only imagine how humiliating this must be for you,” she cooed. "I think if I were in your shoes—oh, silly me, you aren't wearing any shoes," she said with a giggle. "If I were in your situation I think I'd just die of humiliation." She watched me squirm, savoring the twitch of every muscle. “Tell me about Mitch.” I flinched, which did not go unnoticed, and she pounced instantly. “I hear he’s into both girls and boys. Is that true?” I didn't answer. “Answer me, sweetie.”

“Y-Yes, I think that’s true.”

“I hear he likes you, Blondie. Is that true? Is he hot for you? Do you think he wants to get inside your panties?”

“Please, I don't...”

She leaned closer, her breath warm against my face. “You know it’s true, don’t you? That’s why he’s here tonight—just to see you, right?” She pointed at the babydoll nightie draped over a nearby chair. “Mitch is going to be so excited to see you in that, isn’t he, Blondie?”

“Please...”

“Or maybe you should just go out there like this. Would you like that?”

“No!” I snapped, my head jerking up.

Felicity smiled, clearly pleased by my outburst. “Okay, relax, Blondie. I won't make you go out there all naked." She patted my knee. “You can wear the babydoll. Would you like that?” I nodded faintly. The evil little thing was ruthless. “Say it, Blondie. Tell me what you want to wear.”

“The babydoll,” I choked out.

“Say, ‘Please, Felicity, may I wear the babydoll for Mitch?’”

It was becoming excruciating. “P-Please, Felicity, may I wear the babydoll for Mitch?”

“Why of course you may, sweetheart. Mitch will be very excited to see you in your sexy little babydoll.” She grinned at me, then glanced down at my legs. “It’ll really show off those pretty legs.” She released one of my hands and ran her fingers slowly down my thigh. “Mm, so smooth. He’s going to love your silky, slender legs. Don’t you think so, Blondie?”

“Oh God, please, no...”

Her touch traveled higher, toward my hip. “How did your legs get so smooth, Blondie ? Did you shave them?”

“No... I... please, I’d rather not talk about it.”

She lifted my arm and gave it the same treatment, sliding her fingers up and down my bicep. “And such smooth, girlie arms. Pretty, pretty,” she teased, dragging out the t sound with a musical taunt. I fidgeted under her touch, feeling increasingly more uncomfortable. Then she lifted my arm high, zeroing in on my hairless armpit. “And your underarms are nice and smooth, too. How lovely.” She lowered my arm and looked me straight in the eye. “Tell me, Blondie... how did you get so pretty?”

“B-Becky and Brenda,” I muttered. “They did it to me.”

“Oh, and what a wonderful job they did!” she said.

She looked lower, then reached down and gently tugged on a few strands of my pubic hair, causing me to flinch. “Why did they leave your hair down here?” I didn’t answer, just stared straight ahead, praying she’d move on. But of course, she didn’t. “Shall we get rid of it now?”

“NO!” I cried, my eyes widening in horror. That was a critical mistake. Her smile stretched slowly across her face. She’d struck a nerve, and she knew it. She left it alone for the moment, but I had a haunting feeling it was something she would revisit.

Her gaze flicked back down, and her grin turned impish. “Don’t you think you’re a little small down there for a sixteen-year-old?” I fidgeted some more, much to her delight. She knew which buttons to push. “I told you about Joey, my ten-year-old brother. I saw his little wee-wee the other day, and yours is as small as his.” It was at least the third time she had reminded me of that unpleasant piece of information—and it was getting more humiliating each time. “Aren’t you embarrassed when you have to shower after gym class? I’ll bet all the other boys make jokes about your little pee-pee. Oh, you’re really blushing now, Blondie. It must be true.”

I just sat there, silent and mortified, my face feeling like it was on fire. “Talk to me, Blondie; I’m monopolizing the conversation again,” she said, grabbing my hands again and giving them a playful bounce on the mattress.

“I... I don’t know if they joke,” I mumbled weakly.

“Have you ever measured yourself down there? It can’t be more than a couple of inches.”

“No... please.” I stared at the carpet, unable to meet the eyes of the little devil sitting between my knees.

“Look at me, Blondie.” I hesitated, then forced myself to meet her gaze. Her eyes were dancing with delight. “Aren’t you embarrassed to show the other boys your little wee-wee?”

“I don’t know... please, can we talk about something else?”

She smiled. “Okay. Tell me the story about the auditorium.”

I probably would have been more comfortable talking about my penis. “What story?” I’m sure that my body language betrayed my feigned ignorance.

“You know," she said, her grin widening. “When Mitch and Marcia made you strip during the play. Julie told me, and she heard it second hand. I’d like to hear it from you.”

I shifted uncomfortably. “They... they made me take my clothes off. That’s it.”

“You mean you were naked among all those people in the auditorium?”

I nodded, my eyes locked on the bedspread. “But... it was dark,” I offered weakly.

“I heard there was a flashlight. Did Marcia really make you shine a flashlight on your little pee-pee?”

“Yes,” I whispered.

“Ooh, I wish I could have been there—it sounds delicious! Weren’t you just freaking out?”

“It w-wasn’t fun,” I muttered. "Please, you know the story.”

“The story goes that you didn’t have any hair down there back then. Is that true, Blondie, was the light shining on your hairless little wee-wee?”

I felt my face flush hotter. “I don’t remember,” I lied. (It was true.)

She pointed between my legs again, her finger a terrifying inch away. “Shall we remove that unsightly hair before we go out there, sweetie?”

My eyes snapped wide again. “Please, no...” I begged.

“Ah,” she sang. “I touched a nerve again, didn’t I? Well, you know, I don’t have any hair on my privates, so it would only be fair if you didn't, either.” She paused, eyeing me for a reaction. There was none. I was still stunned by the latest turn in the conversation. “Doesn’t that surprise you, Blondie? After all, I’m thirteen now. Most girls have reached puberty before that. Not I. Physically, I have the body of an eleven-year-old. I'm probably emotionally immature, too, if I'm being honest. But I’ve been told that intellectually I’m as smart as a lot of college students.”

I was in no mood to listen to her self-assessment. And the fact that she had the body of an eleven-year-old somehow only made my abject submission to her that much more humiliating. Which, now that I think about it, is probably the reason she was telling me. Like I said before, she was perceptive well beyond her years.

In any case, I had to try to appeal to her, hoping she had at least one ounce of compassion. “Felicity, I’m begging you, please, please let me keep my pubic hair. I’ll do anything, but please don’t do that to me.”

She smiled, both at my anxiety and the “I’ll do anything” remark. Certainly, there was a tacit understanding that this was the case regardless of whether she spared my pubic hair or not.

She tapped her chin thoughtfully. “Now refresh my memory, sweetie. What was it you called me earlier?” And just like that, I knew there was no mercy coming. I lowered my head in gloom. “Something about a female dog... tell me, what exactly was it you called me?”

“A bitch,” I said softly.

"Yes, that was it. A fucking bitch, to be more precise. You really shouldn’t have said that, Blondie. Here I’ve been so nice to you, dressing you up and helping you find your feminine side, and this is the gratitude I get?”

She shook her head dramatically, as if she were truly heartbroken. Then she got up on her knees, reached for my hands, and gently tugged me off the bed.


My Little Pee-Pee Has No Hair

“I think we need to finish what Becky and Brenda started,” Felicity said, drifting toward the nightstand. “Now be a real sweetie and help me find a pair of scissors.” I stood there frozen, stunned at what was about to take place. “Well, don’t just stand there. Check the dresser,” she added with a nudge.

I slowly walked over to the dresser, unbelieving of what was transpiring. There I was, naked, helping my own tormentor in her search for the tools to denude me. I went through the motions, opening the top drawer. As luck (or lack of it) would have it, the first thing I saw was a small pair of scissors. I grabbed them quickly, hoping to hide them under the bed before Felicity could see.

“Good boy, Blondie!” Felicity squealed gleefully, suddenly right behind me. I nearly jumped out of my skin. She plucked the scissors from my hand and snipped them in the air inches from my crotch. I instinctively backed away. “Yes, these should do just fine,” she said, eyeing her target with a mischievous grin.

I dropped to my knees and clasped my hands together in a classic pose of desperate entreaty. I’m sure it looked quite dramatic, and for her a bit comical. “Please, Felicity, I’m begging you, one last time...”

“Oh, for heaven’s sake, how pathetic,” she said, grabbing a few strands of hair from my head and feigning a cut. “Fine, we’ll just start here and work our way down.”

“Okay! Okay!” I cried, scrambling to my feet.

She looked down at her objective, then paused, putting her fingers to her chin as if deep in thought. This, I knew, could not bode well for me.

“Let’s make this fun, Blondie,” eyes widening as if a light had just turned on in her head. “You did so well with ‘Happy Birthday.’ Maybe you can sing for me again. Are you familiar with ‘Old MacDonald Had a Farm?’ ” I nodded gloomily, my stomach twisting into knots. “Great! We’ll use the same tune, but we’ll plug in our own lyrics. Let me think...” She paused for a few seconds while I stood there, wishing for death.

“I’ve got it!” she chirped, eyes gleaming. "It goes like this: ♬ My little pee-pee has no hair, ee-eye-ee-eye-oh... with a snip-snip here, and a snip-snip there, here a snip, there a snip, everywhere a snip-snip... ♬

"Now, here's the really fun part (I must tell the reader that she had a maniacal look in her eyes as she spoke): Every time you sing the word ‘snip,’ I snip off a little bit of your pubic hair. So essentially, you’ll control the snipping with your singing. The more you sing, the balder you’ll get down there. Won’t that be a fun game, Blondie? Oh, this is so exciting!"

She inched closer, weapon at the ready. “Okay, anytime you’re ready, sweetheart. Do you want to practice before we do the real thing?” I shook my head sullenly. “Oh, do me a little favor, and hold your little pee-pee down and out of the way. I’d hate to miss and snip the little thing off, know what I mean?” She laughed aloud, clearly quite amused with herself. I pushed down my penis with my hand. I certainly didn’t need an “accident” to add to my suffering.

There was silence for a few seconds. Felicity stood by anxiously. “Anytime now, Blondie.”

There was no escape. I swallowed the lump in my throat, then began. ♬ "My pee-pee has no ha..." ♬

“No, no, it’s little pee-pee! Now start over.” She was really keyed up.

♬ "My little pee-pee has no hair, ee-eye-ee-eye-oh... with a..." ♬ I hesitated, momentarily unable to continue. Felicity gave me a look of admonition. I carried on. ♬ "...with a snip-snip here..." ♬

Snip. Snip.

I winced as I watched a small amount of my precious pubes gravitate unfettered to the carpet. ♬ “And a snip-snip there...” ♬

Snip. Snip.

♬ “Here a snip, there a snip, everywhere a snip-snip...” ♬

Snip. Snip. Snip. Snip.

A total of eight snips of the scissors coincided with my less than mellifluous intonations. My voice cracked during the last part, as I struggled to maintain my composure.

♬ “My little pee-pee has no hair, ee-eye-ee-eye-oh.” ♬

Felicity squealed with laughter, literally hopping up and down with joy. “Oh my god, that was perfect!” she gasped.

I looked down to assess the damage. I could see the difference, but it wasn’t huge. The little devil was cutting off oh, so little at a time, to prolong my shame—and likewise, her entertainment.

“Let’s do it again!” she said excitedly.

I had no choice. Again I sang the sordid song. The second verse went just like the first. My voice cracked, and every snip brought a fresh wave of mortification.

♬ “My little pee-pee has no hair...” ♬

Eight more snips trimmed away yet more of my pubic hair.

“Let’s do it again!” Her inner child was on full display, and she was completely enthralled by her wicked little game.

After the third round, the loss was undeniable. My feeling of despair was momentarily overshadowing my embarrassment. But that feeling would prove to be short-lived. Felicity handed me the scissors with a bright, cheerful smile.

“Now you do the snipping, Blondie, while you sing. You’ll see, it’s really fun!”

I was incredulous that I would have to participate in my own emasculation while simultaneously singing the stupid song—all for a thirteen-year-old girl's amusement.

"Felicity, please," I tried.

“Oh, come on now, don’t be shy! It’s just you and me... and your little pee-pee.” She chuckled, watching my face glow brighter. I groaned, and after a long, tense silence and a deep, reluctant sigh, I surrendered. I began to sing, while she crouched down and put her head close to the action. My hands quivered as I tentatively started snipping.

♬ “My little pee-pee has no hair...” ♬

My voice cracked with every line, while occasionally Felicity mockingly sang along in harmony. She laughed aloud as she watched my hair disappear bit by bit, savoring every snip. When I finally finished the song, she clapped her hands and bounced on her toes like an overexcited kid at a birthday party. I was starting to think that she was positively deranged.

“Okay, my turn again. Hold your little wee-wee out of the way, and start singing,” she said as she took the scissors in her hand again. “Tell you what let’s do, Blondie. Let’s keep taking turns snipping until there’s nothing left, shall we? Oh, this is just so fun!”

And so we did. We passed the scissors back and forth seven or eight times, while I sang the dreadful song until there was nothing left to cut. Felicity made the final snip, then placed the scissors on the dresser and leaned in to scrutinize the fruits of our labor. There was still some stubble remaining, and she wrinkled her face. She grabbed my elbow and guided me toward Becky’s bathroom.

“We have to finish the job, Blondie, until you’re totally bald down there.” She ran hot water in the sink and soaked a facecloth. “I’ve seen my daddy soften his beard with hot water before shaving. This will make it easier, and you’ll be really smooth,” she explained, then retrieved Becky’s pink razor and some shaving cream from the shower and handed it to me. “Here, you better do it. I’m afraid I might cut you.” She paused. “Unless you want me to get Mitch in here to do it for you." She chuckled at the look on my face and handed me the cloth. “Here, hold this over that stuff you have left for a couple of minutes.”

She reached down and without warning took hold of my balls and strummed her fingers across my scrotum. Startled, I jumped back, letting out a high-pitched squeal, much to Felicity’s amusement.

“I think you’ve got a few hairs on your little balls, so wrap the cloth around those, too.”

She was making sure that I would be totally denuded. Under her watchful eye, I did as instructed, removing the final traces of stubble, bit by bit. When I was done, she handed me a towel, and I dried off quickly, covering myself as best I could.

“Hands behind your back, Blondie. Let me see,” she ordered, all too eagerly. I obeyed with visible reluctance. Her grin widened instantly. “Now it looks just like Joey’s,” she teased, cackling as I turned crimson from head to toe. “Come, let’s have a look in the mirror,” she said, taking my hand. We stood side by side before the full-length mirror. “Go like this.” She put her arms above her head, holding her elbows with her hands. I followed suit and was taken aback by the sight of an apparently prepubescent sixteen-year-old boy. I wanted to cry, but I was beyond tears.

“Well, would you look at that,” she said, admiring me like an artist surveying her sculpture. “You are completely hairless down there. Wait ‘till everybody sees this! You look like a little boy, Blondie. And you're sixteen! Isn’t that precious?" She looked at me and grinned, then began singing. She sang softly, like it was the sweetest lullaby.

♬“Blondie's pee-pee has no hair, ee-eye-ee-eye-oh...” ♬ Then she beamed. "How does it feel to have no hair, Blondie?" I just stared at my reflection in stunned silence, fully aware that I’d reached a new low in humiliation—and knowing full well that we weren’t even finished.


The Babydoll

Felicity brought me out of my stupor when she pulled the pink babydoll nightie over my head. “See, I'm keeping my promise and letting you wear this,” she said cheerfully.

The babydoll was a nightmare. It had short, fluffy sleeves, and the lacy hem dropped just below my balls in the front and barely covered my ass in the back. I nervously tried to pull it down further, but there was no give.

“It’s too short... please, can I just wear the pajamas?” I pleaded.

“Nonsense, sweetheart—it’s perfect. I know it seems short, but you’ve got such pretty legs, it’d be a shame not to show them off.” She paused, tapping her chin again. “Tell you what—I won’t make you wear panties. The babydoll’s so short, they’d show. You wouldn’t want that, would you, Blondie?”

Then it hit me. The girls—and, equally disturbing, Mitch—could easily get an eyeful if I wasn’t careful. I couldn’t believe what I was about to say.

“C-can I... please wear some p-panties?” I cringed at how that sounded.

Felicity blinked, then burst out laughing. “Oh, sweetie, what a good girl you’re becoming. Turn around, let me show you something.” I turned around miserably, my back to the mirror. When I did, Felicity lifted the nightie halfway up my back, exposing my bare ass. “If you wear panties, then Mitch won’t get to see this. We wouldn't want to deprive him of seeing your cute little naked tushy, would we?"

My blush deepened, and Felicity laughed harder. And in that moment, my humiliation was surpassed only by a paralyzing sense of dread.
Last edited by Blondie on Tue Mar 31, 2026 12:51 am, edited 5 times in total.
BABYRYAN2121
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Re: Roosevelt Humiliations

Post by BABYRYAN2121 »

as always... the best SPH!!!
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Re: Roosevelt Humiliations

Post by steam train »

Has to be one of the best written and emotive descriptions of shaving I have had the pleasure of reading. So good to read again.
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