Roosevelt Humiliations

Stories about boys ending up in compromising situations, preferably naked and embarrassed, as the name suggests.
User avatar
Blondie
Posts: 349
Joined: Tue May 16, 2023 7:09 pm
Has thanked: 186 times
Been thanked: 841 times
Contact:

Roosevelt Humiliations, Chapter 15

Post by Blondie »

Image

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 tile floor, silently praying for a miracle.

After a few moments a light tapping came from the door. “Knock-knock!” Julie chirped.

“Yes?” I answered the salesgirl anxiously, my voice cracking like a prepubescent boy’s.

But instead of a response, I heard the unmistakable sound of metal sliding into metal—a key turning in 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 witnessing a naked boy cowering in a dressing room was standard procedure for her. In her hand, she held a measuring tape and a clipboard. On the clipboard was a sheet of paper featuring a hand-drawn 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 from my crouched position, 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 behind her. Naturally, Becky, Brenda, and the young teens needed no further invitation. The door creaked wider, and soon their grinning faces were peeking over each other's shoulders, jockeying for position like spectators at a sporting event. Of course, Julie made absolutely no effort to discourage them. If anything, she seemed to be performing for her audience.

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 upward until it reached 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, my voice cracking with desperate anxiety. “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 loiter in 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 reappeared.

"Sorry for the delay," she said, stepping back into the room with a digital scale tucked under her arm. "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 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 from Julie's outstretched hand. 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 do your lingerie shopping on our website... looks like fourteen inches exactly. You have a lovely, slender swan neck.”

“Fourteen inches,” Becky repeated, writing it down. “Such a delicate little neck.”

I groaned softly.

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

“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.

The teen girls gasped in unison, then broke into high-pitched giggles. I felt so lightheaded from sheer humiliation that I thought I might actually faint.

“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 she'd captured. “See how easy that was? Now let’s get these arms up,” she said, lifting my arms into place. “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, walking around me and giving my chest an appraising look. “And on the flat side—definitely a double A cup.”

“Thirty-two, double A,” Becky said. “Do you even carry that size, Julie? You might have to special-order a little boy’s training bra.”

Another wave of laughter followed as Becky dutifully jotted it down, a pronounced smirk on her face.

"Okay," Julie continued, her tone businesslike. “Let’s get your waist size now. I’ll need you to hold your arms up high in the air—it’s best to take the measurement while you’re fully stretched out, in case you ever want to wear a corset."

I grudgingly raised my arms.

“All the way up, please,” Julie directed, her voice firm. Reluctantly, I obeyed, extending them toward the ceiling.

"Now interlock your fingers and turn your palms upward... that’s it, keep them facing the ceiling so your body is nice and taut. There you go, perfect. All stretched out." She paused, then added, "I must compliment you on your hygiene. You have such lovely, smooth underarms.”

The giggling intensified, becoming almost hysterical. It was true; while I'd started to grow hair elsewhere on my body, my armpits were still as smooth as a child's, a fact that was a source of embarrassment for me but apparently delighted my audience to no end.

She walked behind me to take the measurement, affording the other girls what for them was I’m sure a very entertaining view of my exposed form. “Twenty-eight inches." After a pause, she added, “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 only a few inches from my penis as she purposefully scrutinized her objective—and at that moment, I didn't think it was the tape measurement that held her attention. As she stood up, she couldn’t suppress another smirk, only now it was more pronounced.

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

"Say thank you," Becky commanded softly. "It was really nice of Julie to measure you and care enough to get you properly fitted lingerie."

"Thank you," I whispered.

"Louder," Becky prompted. "And ask nicely for your bra and panties."

"Please," I said, my voice breaking. "Please... may I have the... bra and panties?" That was pure torture.

Julie beamed. "Of course you may, honeybun. That's exactly what we'll get you. A complete set. Maybe two. After all, a girl can never have too much lingerie."

As everyone trickled out, still laughing and chattering about what they'd witnessed, Julie turned back and chirped, "Be right back with your bra and panties!"

The door clicked shut, and I locked it in a hurry, my fingers fumbling with the mechanism. Then I leaned against it, buried my face in my hands, and whispered to the empty room:

“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 lace panties that looked a bit on the small side.

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

Shuddering, I took the panties from her fingers and gingerly slipped them on. They hugged me a little too well. I winced as I glanced downward, taking in the sight of myself in women's underwear.

“Well?” Julie’s voice was expectant.

“They’re... fine,” I answered meekly.

Next came the matching bra, casually passed over the top of the door. “Don’t forget your bra,” came the cheery voice from the other side.

I reached up and took it, holding it at arm’s length and staring 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 fasten it in the back. Would you like some help?”

“No!” I blurted quickly. “I mean... I can do it. I've got it. Really."

After a struggle, I finally managed to secure it. I stood there in women’s underwear, feeling ridiculous—and more than a little humiliated by how thoroughly Julie had orchestrated the moment.

“How are we doing in there?” she asked, all too helpfully.

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

There was a brief, silent pause.

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

"I think we should have a look in the mirror. Make sure everything sits properly."

Of course she does.

I closed my eyes for a moment, trying to gather myself. Then, in resignation, I opened the dressing room door.

“Oh, you look adorable,” Julie gushed, clapping her hands together. She stepped closer. “Do you feel as sexy as you look? Because you look absolutely ravishing in that lavender."

I didn’t dignify that with a response. I couldn't have formed words if I'd wanted to. I simply power-walked toward the mirror, my eyes fixed on the floor, wishing I had a paper bag for my head.

As expected, I was met by a growing crowd of grinning faces. Becky and Brenda stood front and center, beaming at me with expressions of delight. 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 the spectacle.

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

“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 on my heel and bolted toward the dressing room, desperate for cover. But to my horror, when I reached for the door, I found it closed. And locked. Someone was inside.

In a panic, I looked around for another dressing room, but there was none to be found. There was nowhere to hide. I knocked frantically on the door.

"Excuse me?" I called out, my voice cracking with anxiety. "I'm sorry, but can I get in there? I really need—"

A woman’s voice replied, “I beg your pardon, young man, but I’m busy in here.” The occupant paused, and then a face appeared peeking at me over the door, looking me up and down with undisguised interest. Tall Blonde Lady from before. She took in my state of undress—lavender bra, matching panties, burning face—and her grin spread wide. "She's right, you know," she said calmly, "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 in a futile attempt at modesty, 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 have assumed—the arm across the chest, the protective hand, the hunched shoulders. 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 with enough force to rattle the walls. I leaned against it, breathing a sigh of relief like never before. But then I realized with fresh horror—my clothes were still missing.

I poked my head above the door and looked around the store, but they were nowhere to be seen. I spotted Julie a few yards away, helping another customer, and even from here I could see 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 right away. First, though, hand me your bra and panties, and I'll wrap them up for you all nice."


Naked Again

I sighed in resignation, then peeled off the offending garments. I held them over the door, and they were snatched away in a blink. Once again I was left naked and waiting... and waiting... and waiting... and waiting... and waiting...

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

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

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 clothes without parading naked through the store, without giving everyone yet another show. 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 front window from the mall corridor—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! I'm begging you!"


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. "Right now."

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 ten minutes ago.” 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! Not like this!”

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, trying to pretend I was anywhere else, and not wearing skimpy, feminine lingerie. But there was Julie, waving merrily from behind the counter, her arm raised high.

“Yoo-hoo! Don’t forget to pay for your lingerie, sir!” she called, delighting in every word, her voice carrying across the entire store. "We can't let you leave without paying for your pretty things!"

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, who then took an unusually long time to complete the transaction while I stood there, utterly mortified, the teddy clinging to me like a constant reminder of my humiliation.

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, screaming the brand to anyone who cared to look. “Thank you so much,” she said. “You’re my new favorite customer. Really, you are. 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 from a group of young women, an “Oh, how darling!” from a passing group of older women, and—just to seal my humiliation completely—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 Wed Sep 02, 2026 9:31 pm, edited 9 times in total.
User avatar
Blondie
Posts: 349
Joined: Tue May 16, 2023 7:09 pm
Has thanked: 186 times
Been thanked: 841 times
Contact:

Roosevelt Humiliations, Chapter 16

Post by Blondie »

Image

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 have been trying to put these memories 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 who remain grimly amused by my suffering.

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

After that incident, I understood my position all too clearly: I was completely, utterly under their control. Any time I so much as considered defying them, I had only to remember what happened at the beach—ending up stark naked in public before being forced into one of my sister's swimsuits—to remind myself just how bad things could get. And I had no doubt they could, and would, get even 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 whenever those two put their scheming, devilish heads together, it never boded well for me. Whenever Brenda came over to the house, I felt an immediate wave of dread washing over me. Dealing with Becky alone had been 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 antics.

“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. "Someone's being awfully bitchy this evening."

“Maybe Blondie’s afraid we’ll surprise him while he’s massaging his little weenie,” Brenda chimed in. They both burst into laughter. "Or maybe he was just about to try on his pretty new outfits from Victoria's Secret. Is that it, Blondie? Were you getting ready for a private fashion show?"

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

"Hmm, you know what? That's actually a fantastic 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. The silence that followed was deafening.

“Okay, that’s it, Blondie,” reprimanded Becky, her tone ice cold. "I have had quite enough of your attitude lately. And to show disrespect like that in front of my guest? Oh, 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. "Don't go anywhere.”

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

“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 stammered. "I don’t know what got into me earlier. I’m just... really tired. Honestly, I didn't mean it, I swear. I was just frustrated about the game, and I took it out on you. I'm sorry."

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." She stepped closer, her eyes gleaming. "Now, here’s what’s going to happen: You're going to put on your new bra and panties, and you're going to 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, my mouth hanging open. But she wasn't finished.

"Then, if you’re really nice,” she added with a smirk, "if you're sweet and obedient and properly apologetic, we might even put on some music and let you entertain us with a little dance. On the coffee table. In your sexy underwear. Would you like that, Blondie? Would you like to dance for us?" She didn't wait for an answer. "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. Don't keep us waiting."

She dropped the lingerie on my bed, and Brenda came up behind her. "Don't worry, sweetheart," she cooed, stepping forward to pinch my cheek. "You're going to look absolutely adorable. And I have a feeling you're going to be quite the dancer. I can't wait!"

They left me alone with my doom, the door clicking shut behind them. 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 was not in a public place, that at least the humiliation would be contained within these walls. But Brenda and Becky were enjoying my disgrace far 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 that made my stomach churn.

But I had no recourse. To disobey them would mean much worse repercussions down the road. Shuddering, I slipped the panties up my legs, then pulled on the bra. After several fumbling attempts, I finally managed to fasten it in the back.

I turned to the mirror and pulled the straps over my shoulders, taking in the deeply uncomfortable reflection staring back at me. Against my better judgment, I even turned around to see how I looked from behind, then immediately chastised myself for doing so. I remember thinking that, from the rear, I could probably pass for a girl, which would only give the girls more ammunition to tease me with, given my smooth skin and slight build. Fortunately, I'd grown some hair on my legs. It was blond and not especially noticeable, but at least it offered some small hint of masculinity.

I sat on the bed with my head in my hands. My moment of self-pity was short-lived and interrupted by Becky's voice.

“Blondie, we’re waiting,” Becky’s voice sang from the living room. “Come on out and shake those hips for us! Don't be shy now!" 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 carrying through the hallway. 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 on several occasions, but I always squelched the idea at the last moment. 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, scrambling for my clothes with frantic haste, but just as I did, Brenda barged in.

“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 with shame.

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. Soon, I think. Very soon."

She exited the room with a giggle, leaving me alone with my pounding heart. 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. For now, at least, I was safe.


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 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. She leaned forward slightly. “It would be such a treat if you could put on a fashion show for us sometime. Maybe something lacy? Something with a little bow on the front?" They all giggled.

“Oh, absolutely,” Becky added, taking the cue. "He makes a lovely little teenybopper. Don't you think? All blushing and bashful. He looked so precious in his little bra."

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 coiled and ready to attack. My stomach tightened.

“Can you believe,” she said to the group, never taking her eyes off me, “that he told me to ‘eat shit’ last night? Such language! I mean, is that any way for a proper young lady to speak? Wherever did you learn such vulgarity, Blondie?”

I jerked my head back as the lipstick crept toward my face, but Brenda was quicker. Her hands closed firmly around my shoulders, holding me fast.

“Hold still, darling,” she whispered, just loud enough for me to hear the amusement in her voice. "We wouldn't want to smudge that pretty face, would we?"

“Maybe if you looked more like a girl,” Becky mused, “you'd learn not to speak to your fellow females so rudely.” The tube hovered at my lips. “Let's find out, shall we?”

Before I could wriggle free, she was applying the lipstick. It was bright pink, thick, and greasy. Every stroke drew fresh laughter from the group as I sat frozen with mortification, my face blazing and my hands clenched into fists at my sides.

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

Becky stepped back to admire her work, smirking with pleasure. "That's a good girl, Blondie. Very pretty. Now hold still while I add a little blush. Really complete the look." 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. Absolutely radiant.”

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 beneath a maple tree. They looked like sophomores, maybe juniors. At the moment they were oblivious to my predicament. That was about to change.

“Do me a favor, Blondie," Becky continued. "Go ask them if they have any eye shadow you can borrow." She turned back to me, her smile widening. "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. “Beck, please. I’m really sorry about last night. I swear, it won’t happen again. I'll... I'll do your homework. Just please, not this.”

Becky just 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. In front of everyone. Is that what you want?"

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

I reluctantly stood up, my legs unsteady, and made my way over to the two strangers. Each step felt like I was walking through water.

I decided to take a 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 with brown eyes. Her eyebrows were furrowed in confusion. "Are you in a play or something?"

“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 a victim of another Roosevelt hazing.

The faces of both girls lit up with delight. They pounced on the opportunity to join in the festivities.

“Come on now, ‘fess up,” the brunette teased, stepping closer. “The eye shadow is for you, isn’t it? You want to look pretty for your girlfriends over there?" Both girls were giggling now.

“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. All shy and nervous. I’ll tell you what: You can have some eye shadow if you let me put it on you.”

I hesitated, my mind racing, weighing my options, such as they were. Public humiliation now, or bra and panties tomorrow?

“Okay,” I muttered.

She grinned and produced a compact of baby-blue eye 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! I can't believe he's actually letting you do it!"

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, appraising her work.

"Oh, yes, you look lovely, little schoolgirl. So pretty. So sweet."

I turned and walked back toward my tormentors, my head bowed and my eyes fixed on the concrete.

“Thanks for coming by, cupcake!” the brunette called after me. "Come back anytime you need your face done!"

I walked away from the laughter of two strangers and straight 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. This was just the appetizer."

I didn't stick around to hear anything else. Spitting out the awful taste, I bolted for the bathroom, which, fortunately, was empty. I wiped away the lipstick and scrubbed off the eye shadow as fast as I could. I shivered at the thought that Becky still had another reprimand in store for me.

Sure enough, it came just a few days later—in spades.
Last edited by Blondie on Wed Sep 02, 2026 9:31 pm, edited 7 times in total.
User avatar
Blondie
Posts: 349
Joined: Tue May 16, 2023 7:09 pm
Has thanked: 186 times
Been thanked: 841 times
Contact:

Roosevelt Humiliations, Chapter 17

Post by Blondie »

Image

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 supposedly gone off on some overnight adventure with Brenda. I had the place to myself, and I was looking forward to the solitude more than I could say.

I peeled off my sweaty 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, that I started nodding off almost immediately.

I don't know how long I was out, but I was rudely awakened by a tickling sensation on my balls. My eyes snapped open, and I nearly died on the spot. Standing over me were the grinning faces of Becky and Brenda, their eyes gleaming with delight.

I yelped and instinctively swatted Brenda's hand away. The two girls were laughing uproariously as I flailed about for a moment, completely 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 when a friend and I intentionally barged in on her while she was taking a bath. She'd never forgiven me for it, and she was surely in her element now, savoring every second of this classic case of poetic justice.

“How precious," Becky teased. "A bubble bath. 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 some precious little sissy boy. It seems to me you want to be a girl. Doesn't it seem that way to you, Brenda?"

"One hundred percent," Brenda responded. "I think he wants to be sissified."

"Well, sweetheart," Becky said, "just sit back and relax. Auntie Brenda and I are about to make your dreams come true."

The grinning Becky reached across the tub and grabbed her pink disposable razor from the edge. “Brenda, there’s another one of these in the medicine cabinet. "I'll start on his legs. Maybe you could handle his underarms—if he even has any hair under there. Poor late bloomer that he is."

Becky giggled, and Brenda wasted no time producing another razor. She grinned wickedly. "Don't worry, Blondie. We'll have you presentable in no time. Boys like their girls nice and smooth."

“Hold up your leg,” demanded Becky.

“Wait! No! Becky, stop!” I was horrified. As Becky alluded to, 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. I bolted upright. "Please, I’ll do anything! Just don't!”

“Anything?” Brenda asked, popping the cap off a second razor. She moved closer. “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," Becky snapped, turning toward the door. "I'm getting the scissors. Let's cut off all his pubic hair first. Then we'll take some pictures."

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

Their grins returned, wider now. Becky grabbed my foot and lifted my leg into the air. I couldn’t believe what was happening.

"There we go," she cooed. "Now hold still, sweetie. We don't want any nicks on these pretty legs of yours."

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.” She held up the razor, showing me the collected hair. "Say goodbye to your fuzzy wuzzies."

I closed my eyes, wincing, as I couldn't bear to watch my masculinity being stripped away stroke by stroke.

Then Brenda pulled on my wrist. "Arm up, sugar plum," she sang. "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, sweetheart, 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 exactly what she was doing.

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, princess,” 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 instantly. “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, desperately 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 with fresh shaving cream. Almost seventeen long years to finally grow, I remember thinking, and it's all disappearing at the whims of the fiendish twosome.

As Becky began the first long stroke of the razor, she looked up at me with a sparkle in her eye. "I notice you've got some fuzz on your arms, too. Can't have that. You need to look pretty when you model your lingerie for us later." She paused, the razor hovering. "Actually, I think you could use the practice. Doing it yourself, I mean. So you'll be able to manage this on your own next time." She nodded toward 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. Your choice, darling."

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, dollface,” 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 couldn't take my eyes off my now-hairless arms. I suppose I'd grown so accustomed to that light layer of hair that the sudden change came as a shock. The skin looked unnaturally smooth—so bare, so strangely delicate. It really sank in, in that moment, what they had done to me. What they were still doing. I was mesmerized—until I was quickly pulled out of it by Brenda, who noticed my fascination.

“That’s right, cupcake,” she cooed. “Just like a girlie’s arms. Soft and smooth and absolutely precious." Her gaze drifted lower, to where my legs were still hidden beneath the bubbles. “I'm dying to see how pretty your legs are. I bet they're just darling.”

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

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

I flinched and removed my foot. The water resumed its downward spiral.

“Please, you guys,” I appealed. I was near tears. “You’ve done enough. Can't you just... can't you just go away and leave me alone?"

“And miss the big reveal?” Becky countered. “We have to see the fruits of our labor, little miss. All that careful, loving attention we gave you? We deserve to admire our handiwork."

I lay back in the tub, staring at the ceiling, listening to the water make its inexorable disappearance down the drain. When all the water had vanished, my body remained covered with a thin layer of bubbles, already beginning to dissolve.

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

I stood on shaking legs, my back turned toward them, my hands clamped over my crotch. Becky grabbed the handheld showerhead from its hook. 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 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 expressions of gloating pleasure, like proud artists admiring a masterpiece they’d just finished.

"Okay, the moment of truth, cute cheeks," Becky chirped, clapping her hands together. "God, this is even more fun than I imagined! Turn around, Blondie. Come on, snap to! Don't make us wait."

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

“Arms up high, girlie-boy,” Becky 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, the bubbles running down my legs to swirl in the drain. "Look at him! Just look!"

“Doesn’t she have the cutest little clitty?” Brenda mocked. "Like a little girl's."

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, little darling,” Becky ordered, beckoning me with a crooked finger. "Let's dry you off and get you properly prepared. There's still so much to do."

Whaaat? What else can they possibly do?

I stepped out of the tub on unsteady legs. It seemed like I'd been trapped in there for days. Brenda was waiting with a fluffy pink towel and a grin that stretched from ear to ear. She began gently patting me dry, treating me like a pampered little doll, like something delicate and something she owned.


Their Plans for Me Revealed

As Brenda dabbed at my shins with careful attention, Becky stood beside me with a particular glint in her eyes. Then she dropped the bomb.

“Guess what, Blondie? We’re having a little slumber party tonight, and you’re going to be the entertainment." She paused, letting the words sink in, watching my face carefully. "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. They're very particular about that." She leaned closer. "Oh, and if you’re really, really good, we might even invite Mitch.”

My eyes went wide. Becky smirked knowingly, reading my reaction with satisfaction. “Don’t you think he’d love to see how pretty you look? All smooth and silky? I bet he'd just devour you."

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, maintaining that one small patch of masculinity, was the only positive I could take from this god-awful experience in the bathtub.

Brenda hung the towel over the rack as Becky reached for a bottle of body lotion on the counter, dispensing a generous dollop into her palm. The scent hit me immediately—something floral, sweet, and unmistakably feminine. “This will make your skin sooo soft. And you’ll smell nice and pretty, too, like a proper girl should." She began massaging the lotion into my chest and stomach. Within moments, its soft floral fragrance had filled 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, that they'd engineered this transformation, only made the sensation worse. I wasn’t just humiliated by what they’d done to me... I was humiliated by how it felt.

Brenda leaned in close, her nose nearly touching my shoulder, and took an exaggerated sniff. “Oh, Blondie, I’m telling you, you’re going to drive Mitch absolutely wild!” “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 even feel like I was looking at myself. My skin was so smooth, so hairless. I looked... delicate. Soft. Feminine in a way that went beyond any clothing or makeup. I couldn't deny what was staring back at me, much as I wanted to.

Brenda pounced on my hesitation immediately. She stepped behind me, guiding my arms up to cross them over my head in a pose of submission, then placed her hands on my waist. We stood there, cheek to cheek, staring at the reflection of what I'd become. “See how lovely you look, princess?” she cooed. "See what a pretty thing you are?"

I couldn’t take it anymore. I let my arms drop to my sides 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.”

Even after everything I'd just endured, deep in the pit of my stomach, I knew... the worst was still to come.
Last edited by Blondie on Wed Sep 02, 2026 9:31 pm, edited 6 times in total.
User avatar
Blondie
Posts: 349
Joined: Tue May 16, 2023 7:09 pm
Has thanked: 186 times
Been thanked: 841 times
Contact:

Roosevelt Humiliations, Chapter 18

Post by Blondie »

Image

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, positively giddy with delight, while I sank deeper and deeper into 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. They seemed intent on humiliation through feminization, and they were succeeding spectacularly. And now I was facing the horror of a slumber party with their friends... with me as the "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 crossed to her dresser 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. “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, my voice cracking slightly. "Don't do this to me. Becky, I'm begging you. This has gone far enough. Please, just let me get dressed. Just please, don't make me—"

"Oh, hush now," Brenda interrupted. "Stop your whining, pumpkin. You need to be dressed like a proper girl."

Becky knelt down, holding the panties open at my foot with an expectant look. “Step in, sweetie. Time to get ready for your guests.”

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

“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.” She held up her phone, and I could see Mitch's contact photo grinning back at me.

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. "And don't make me ask twice, or I'll call Mitch right now and tell him you're being uncooperative."

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. The sound cracked through the room, followed immediately by the sting.

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. “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. "Unless you want Auntie Brenda to give you another spanking? I'm sure she'd be happy to. Wouldn't you, Brenda?"

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. "Just look at that blush. I think it's my favorite part. Well, that and her cute little clitty."

As they both burst into laughter, I instinctively reached to cover myself again.

“Uh, uh, uh,” Becky admonished, wagging a finger. “No touching your little clitty. Bad girls who touch themselves without permission get their bare little bottom spanked.”

The diabolical girls giggled freely as I slumped my shoulders over the latest disparagement, the word "clitty" echoing in my skull.

“Put 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, the sensation making me flinch.

“So smooth,” she cooed. I felt her warm breath against my ear. "So charming. You know, Becky, I think the shaving was a brilliant touch. He really does look like a preteen girl. All smooth and innocent."

Her caresses continued, and again I flinched, much to Brenda's enjoyment. 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 with her palm. “And feel how warm they are.” Now both girls had their hands on me, rubbing and stroking and making mocking commentary.

“And check out his legs,” Brenda added, running a hand up my thigh. “Feel 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 clearly reveling in the moment, and all I could do was stand there helplessly, catering to their whims as their little plaything.


The Guests Arrive

The doorbell rang, briefly interrupting their merriment. “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. Everyone's going to be so jealous of how pretty you look.”

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? I could give them a sneak preview.”

“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, clapping her hands together. “You remember Julie, Blondie. She was the salesgirl who was so helpful at Victoria’s Secret during our little trip to the mall. The one who said you had such delicate skin. She asked about you, you know. Said she hoped she'd see you again."”

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. She has such an eye for lingerie.”

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! I'll do your homework. 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. "And you'll do my homework too, if I ask. But right now? Right now we're going to have some fun with you. Now let's go. We've kept your guests waiting long enough." She took my hand and pulled me toward the door. I resisted, my feet dragging.

“Do you want your bare ass spanked in front of all those girls? Do you? Or maybe they'd all like to take turns? What do you think, Blondie? Would you prefer that?" Becky paused and stared at me, probably accepting my silence as resignation. "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, clearly satisfied with 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 the inevitable meeting with the voices waiting in the living room. The nylon of the nightgown swished against my freshly shaved legs, a constant reminder of what I'd become to them.

Not a brother. Not even a boy anymore.

Just Blondie.

Just their entertainment for the evening.
Last edited by Blondie on Wed Sep 02, 2026 9:31 pm, edited 6 times in total.
User avatar
Blondie
Posts: 349
Joined: Tue May 16, 2023 7:09 pm
Has thanked: 186 times
Been thanked: 841 times
Contact:

Roosevelt Humiliations, Chapter 19

Post by Blondie »

Image

Chapter 19: The Slumber Party Begins

A Reprimand from Becky

My anxiety crested 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. 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 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? Do you want everyone to see your little sissy bottom turning pink?"

There was an audible gasp from the living room, followed by a wave of giggles. Apparently, the peanut gallery was very tuned in, hanging on every word. 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 aptly, 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—eyes that seemed to delight in my humiliation.

“Come, come, Blondie dear,” Becky said, “Don’t be rude. Say hello to our guests. They've come just to see you, after all.”

I still hadn’t looked up, but I could feel the presence of someone unfamiliar at the far end of the couch—a new variable that would likely somehow add to my humiliation.

Becky started the introductions at the other side, her hand on my shoulder. “You remember Cheryl, don’t you, Blondie?”

Cheryl extended her hand, grinning, her eyes sweeping over my outfit. “It’s a pleasure to see you again, Blondie,” she said with a grin. “That’s a beautiful nightgown. It's such a lovely color on you. It really brings out your... femininity.”

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... for the compliment.. Cheryl,” I managed. 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. That only brought on more giggling from the amused guests. Somehow my face flushed brighter.

I felt Becky 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, her eyes roaming over my body. Becky’s elbow jabbed me again, harder this time. 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, while I squirmed under her gaze, feeling exposed despite the nightgown covering me. “How have you been?” I added, immediately feeling ridiculous.

That did it. Joanna burst into laughter, setting the others off all over again. My face burned, and I felt hot all over.

"Oh, Blondie," she managed between gasps of laughter, wiping tears from her eyes, “we are going to have so much fun with you tonight!” I cringed, knowing it was all too true.

Then came Julie, the salesgirl from Victoria’s Secret. The girl seated beside her immediately caught my attention, and I felt a fresh wave of unease. She looked to be about eleven or twelve years old. Being paraded around like this was bad enough, but somehow being humiliated in front of a much younger girl made it feel even 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'd love to see how they fit your... figure."

I didn’t answer right away, and again Becky’s elbow jabbed me. “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 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. Your reputation precedes you." I sensed a degree of precocity in her 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. She was practically bouncing off the walls. Doesn't that make you feel special, Blondie? To be someone's birthday entertainment?" 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 Felicity a happy birthday,” chirped Becky.

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

"Why thank you, Blondie. You're such a sweetheart," Felicity said, her smile widening. "I can tell we're going to get along famously. I have so many questions for you, so many things I've been wondering."

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, who would be the evening's main attraction.

“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. Like a baby's skin, practically."

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, but there was nowhere to go. Joanna's grin widened, and she raised her voice, ensuring everyone could hear.

“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, my hands trembling.

“Please, just leave me alone!” I begged, my voice cracking. I was on the verge of tears, but I 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. No secrets among friends. We're all girls here, after all."

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? Tell us—what color are your little sissy panties?"

I fidgeted nervously, my hands twisting in my lap. “Pink,” I mumbled.

“Ooh, how darling," teased Joanna. "Do you like wearing your pretty pink panties? Hm? Do they make you excited? Do they make your little clitty twitch?" She tried to reach for my penis, but I pulled her hand away desperately. 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, the room spinning around me.

Cheryl was nearly in tears from laughing. "Oh, Joanna, you're wicked! Absolutely wicked!"

I knew there would be no letup until I gave them what they wanted. 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 expression, 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? Felicity's been reading at a college level since she was twelve. She likes to to show off her vocabulary."

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 Sep 02, 2026 9:32 pm, edited 7 times in total.
User avatar
Blondie
Posts: 349
Joined: Tue May 16, 2023 7:09 pm
Has thanked: 186 times
Been thanked: 841 times
Contact:

Roosevelt Humiliations, Chapter 20

Post by Blondie »

Image

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, while a large Victoria's Secret tote swung from her other hand. Trailing close behind was Felicity, her spunky little sister, grinning from ear to ear.

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 was about to see. My fears were confirmed when she said, “Ah, here we go. She’ll look just divine in this,” and pulled out what could only be described as a little girl's party dress. She held it up with both hands. It was baby blue, with a short, flared skirt that would barely reach mid-thigh, short puffy sleeves, and a satin ribbon that tied in a bow at the waist. 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, already imagining walking into that living room dressed like a little girl—until Julie’s next words jolted me back to the present.

“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, her hands already reaching forward.

“You betcha!” Felicity squealed. 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." She paused, letting the image settle. "Then you’ll model your pretty new party dress for us anyway. So it’s your choice. “Either way”—she pointed at the dress hanging on the bedpost—“you’ll be wearing that by the time we’re done.” Now... which way would you like it? The easy way, with just us? Or the hard way, with an audience?"

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. What choice did I have, really?

“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, but now she was ready to join in. Kneeling before me, 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 pretty, so smooth—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. "Do they make you feel pretty?" 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, my eyes squeezed shut. Julie giggled. “Just as I thought—not a hair anywhere,” she said, inspecting my smooth underarms with obvious amusement. "Becky really did think of everything, didn't she?" 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. The smirk on her face told me I wasn't going to like whatever came next. 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 against my skin. She turned, chuckling to herself, 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 notion of the thirteen-year-old inspecting my most private parts against my will was just too much, too violating.

“Blondie?” she warned with an admonishing look.

I straightened up and reluctantly submitted to the mischievous sprite, my body rigid with tension. Eyes squeezed shut, I braced myself as the elastic stretched away again, the cool air rushing in. Her hair tickled my stomach as she leaned in, her breath warm against my skin. Though my eyes stayed closed, the image of her staring down the panties burned in my mind.

After what felt like an agonizing eternity, she let go and the elastic snapped against my belly.

“Well, little sister?” Julie asked, clearly enjoying the show from her perch on the bed. "What's the verdict?

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

Julie laughed boisterously and approached me, locking eyes with me 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? I mean, that's what my health class teacher says. But maybe some boys are just... smaller."

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, stepping closer, staring me down until I gave in, hoping to speed the interaction to a conclusion.

“Sixteen,” I whispered, my eyes fixed on some point over her shoulder, anywhere but her face.

“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, my hands clenching and unclenching at my sides.


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 with a drawstring. 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. I couldn'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 white 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—what must have been pure horror on my face—she waltzed over to me and cupped my chin in her hand, forcing me to meet her eyes.

“Don’t worry, sweetie," she teased, her thumb brushing my cheek. "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, her hands already reaching for the petticoat. 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! You have to see how adorable you look!"

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, my mouth slightly open.

Julie appeared at my other side. "Oh, she looks precious," she purred, her hand resting on my shoulder. "What do you think, Blondie, are you getting in touch with your feminine side? Do you feel pretty?"

I shook my head, eyes wide with disbelief. They just giggled.

"Come, my petticoated one," Julie teased, leading me back to the bed with a gentle tug on my hand. "Let's finish your outfit. We can't have you going out there half-dressed, can we?" The petticoat made an audible swish-swish with every step, adding to my mortification. Julie patted the mattress. "Sit."

I sat, and instantly regretted it. The skirt flared up, prompting a delighted squeal from Felicity as she crouched down, peeking underneath shamelessly. Mortified, I clamped my knees together and pressed the petticoat down with both hands. And in that moment, in the very action of trying to preserve some scrap of dignity, I realized 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 on the bed and threw an arm around my shoulders. “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 shifted position, turning to face me fully. She 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 small buckles. Little girls' shoes. 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 are absolutely brand new, you know. Becky was so helpful. She told me your size, and would you look at that? They appear to be a perfect fit.

She slipped one onto my foot, fastening it snugly, then handed the other to Felicity, who eagerly accepted it. "Oh, this is so much fun," Felicity said, dropping to her knees to do the deed. "I can't wait to see these on you."

Once both shoes were secured, Felicity grabbed my hand and pulled me to my feet. “Let’s go see, Blondie!” she squealed merrily.

She dragged me back to the mirror, and I stumbled after her. Staring back at me was a distraught, red-faced boy in a flared white petticoat, now 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 mounting disbelief as the hem dropped past my waist, past my hips, settling just an inch above the petticoat.

"Hold still," Julie said, zipping me up from behind. "There we are. Perfect."

Meanwhile, Felicity fussed with the sleeves, adjusting them until the puffed shoulders sat exactly so, then moved to the hem, smoothing it out with obsessive care.

"Almost finished," Julie announced. "Just one final touch."

Then came the pièce de résistance. Julie produced a massive baby-blue bow and pinned it 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!”

"Turn around," Felicity commanded. "Let's see the full effect."

I rotated slowly, the petticoat rustling with every movement. Both girls busied themselves with final adjustments—Julie fluffing the skirt, Felicity straightening a ribbon—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 flinched again when she slipped her head beneath the petticoat. 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, obscenely frilly, with layers of ruffles cascading across the rear in shades of white and pale blue.

“Time for your frou-frous, little girl,” giggled Julie, kneeling before me. "Be a good girl and lift your feet for 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 good look, sweetie," she instructed. "I want you to see exactly what everyone else is going to see."

I did, and to my dismay, layers of ruffles peeked from beneath the petticoat's hem. I tried to tug the hem down, but it simply sprang 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. “There's nothing to cry about. They’re going to love your pretty dress. You're going to be a big hit, I promise.”

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

Julie just smiled, took my hand in hers, and said, “Now, now. The best thing for you is to go out and play with your friends. You'll feel so much better once you're out there having fun. 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, digging my heels into the carpet, 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 wooden hairbrush, and tapped it against her palm. “Pull up her petticoat, Felicity.”

“No, please!” I yelped in protest, backing away. But Felicity was already behind me, grinning as she flipped the fluffy white layers upward, gathering them in her arms and holding them bunched firmly against my back.

“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 of the ruffled panties and tugged them down to my knees.

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 sound cracking through the room like gunshots. 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.

"Look at her jump!" Felicity crowed.

"Like a little rabbit!" Julie agreed, wiping tears of laughter from her eyes. "Oh God, Blondie, that was too funny. I'm sorry the others missed it. They would have absolutely died."

When the pain finally began to fade, I pulled the panties back up with shaky fingers. Julie leaned in. “Now, are you ready to join the party like a good little girl, or do we need to discipline you some more? Because I can keep going." There was a pause. "Answer me, Blondie. Are you ready to behave?"

“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 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. “All your friends are waiting for you. Soon everyone will get to see just how precious you look.”

That did not help at all.

"Let's not keep them waiting any longer, sugar pie," she continued, taking my hand once more. "Up we go. Chin up. Shoulders back. Be a good girl now."

Julie took one hand, Felicity the other, and this time I did not 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. Look at her little face!”

I can’t really remember who said what, but the scornful comments went on for what felt like hours 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 single 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 whenever 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, the clapping and turning and elaborate hand gestures. Twice. She made me do it twice.

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

—Perform “I’m a Little Teapot," complete with the handle and the spout and the "tip me over" finale.

—Stand in the center of the room holding up the petticoat while the giggling girls made mocking comments on the panties, my pretty legs, how smooth I was, and how girly I looked.

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. So much more.

Next time around, when I can bring myself to relive it, I'll tell you how I was rendered naked by the precocious, demonic Felicity.

For now, I'll simply say this: I would have gladly taken another round with the petticoat over what came next.
Last edited by Blondie on Wed Sep 02, 2026 9:32 pm, edited 9 times in total.
User avatar
Blondie
Posts: 349
Joined: Tue May 16, 2023 7:09 pm
Has thanked: 186 times
Been thanked: 841 times
Contact:

Roosevelt Humiliations, Chapter 21

Post by Blondie »

Image

Chapter 21: Felicity

Alone with a Little Devil

While they put me through my paces in that mortifying party dress, I noticed with a bit of trepidation that Julie was reaching for the Victoria's Secrets 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, her curiosity piqued. “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." Felicity's eyes never left my face as she spoke. "You know... so we can get to know each other better."

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." She shook her head, still chuckling. "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," Julie continued. "Now toddle along, you two. And take your time, enjoy yourselves.” More giggles followed. “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 took mine with the other, leading me down the hallway. I remember noticing how small her fingers were. The realization that I was under the control of a young girl only deepened my humiliation.

“So,” she said conversationally as we walked, “what’s your favorite color? Mine’s pink. I’m a bit of a pink fanatic.” She looked me up and down, smiling to herself. “I have to say, seeing you in those pink panties earlier got me a little excited.”

I was in no mood for small talk—or any talk at all, for that matter—and said nothing.

"That's okay," she said. “We can work on your conversational skills once we're in Becky's room.”

The next hour would prove to be nearly unbearable.

* * * * * *

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

I obeyed with a heavy sense of apprehension. Perching on the edge of the mattress, 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, her little fingers 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 entirely. She stood up abruptly and pointed her index finger directly 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, staring downward.

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? What do you dream about? 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. Metaphorically speaking.” She giggled to herself, tossing a sock aside.

I was miserable. Utterly, completely miserable. I had to push 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 from the bed. “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!" she exclaimed. "See, we have something in common. Do you like to dance?” The zipper was all the way down, the dress loosening around me. “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, my face burning with shame. She stepped in front of me and looked me over, her grin widening as she took in the sight.

“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 now, 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, stripped away piece by piece.

“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 first. Was it a teddy? Julie said you looked absolutely precious in that."

“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 nothing but... 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, waiting.

“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? Your cheeks are positively glowing.” She was the devil in disguise.

"Yes," I answered, looking at the floor, shamefaced.

“Go like this.” She made two fists and put both hands on her hips, her elbows pointing to the sides. I struck the pose, feeling more exposed by the second. She circled me slowly, drinking it all in.

“Oh my. Look at you. Just adorable. But...” She slowly ran a single finger down my tummy, stopping at the waistband of the panties. The touch was light, almost delicate, but it made me flinch. “...these are going to have to come off, so you can model your next outfit.”

She reached for the waistband of the panties, her eyes 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." She let her hand fall away, and I felt a moment's relief. "Well, there’s no hurry. We’ll save it for later." She turned to the VS bag. "For now, we need to find you something cute to wear.” She opened the bag and casually rustled 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 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 your guests, now can we? They'd be so disappointed." 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. "Don't... don't do this."

“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, my eyes glued to the carpet. My silence only energized her more. “Why is that, Blondie? Are you shy? Are you modest? Or is it something else?"

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 terrible mistake. “You’ll be sorry you said that, Blondie." She spoke softly, almost thoughtfully. "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? Tell everyone how difficult you're being? How you won't cooperate with the birthday girl?"

“No,” I muttered.

Just then, the doorbell rang. I winced, my whole body tensing.

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." She glanced toward the door, then back at me, and her smile widened. "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 onto the stool. I faced her, my hands instinctively cupping the small bulge in the panties while she stood grinning, eye-level with my shame.

Felicity grasped the hem on each side with her fingers, and held them there, teasing me, stretching the moment. 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. What answer existed for that?

“I’m doing all the talking now, Blondie, and I don’t appreciate it. Now, be a good boy and ask me nicely to pull down your panties. And say please."

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

She beamed with genuine pleasure. “Why certainly, sweetheart,” she replied. “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?" She was poised, fingers lightly against my hips. "On three: One... two...” Then she stopped and stepped back, releasing the hem.

“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. “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 like a child. 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 at me like a kid on Christmas morning. “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, her voice breathy with excitement. 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, or not run.

"Louder, Blondie!"

♬“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.

Suddenly, the door flew open. Becky stood there, her jaw literally dropping at the unusual sight—the boy on the stool, hands behind his head, panties at his ankles, the younger girl applauding like she'd just seen the grand finale of a Broadway show.

“Oh my GOD! Blondie, what is Felicity doing to you?!” she exclaimed. Then, when the scene kicked in for her, her hands flew to her mouth, and she was overtaken by convulsive laughter.

I buckled forward, arms clamped over my crotch, my face burning hotter than ever. 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 started to turn away, then looked back over her shoulder. "But maybe... hurry a little? Blondie's fans are starting to get restless. Especially Mitch."

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, who seemed hell-bent on humiliating me by any means at her disposal, and who had just demonstrated that her imagination for my humiliation knew no bounds.

"Well," Felicity said, breaking the momentary silence. "Where were we?"
Last edited by Blondie on Wed Sep 02, 2026 9:32 pm, edited 6 times in total.
User avatar
Blondie
Posts: 349
Joined: Tue May 16, 2023 7:09 pm
Has thanked: 186 times
Been thanked: 841 times
Contact:

Roosevelt Humiliations, Chapter 22

Post by Blondie »

Image

Chapter 22: Denuded by a Thirteen-Year-Old

Naked on the Bed

Felicity grinned wickedly at me for several long seconds. I stood there on the stool, still bent over at the waist. Without a word, she gripped my ankle and lifted, first one leg and then the other, stripping the panties free from my feet. I was now completely, undeniably naked, and at her mercy.

She let the panties fall to the floor and reached out for my hand, palm up. “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 continue. 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 toward the bed. I followed her like a reluctant dance partner.

“Up we go,” she said cheerfully, climbing onto the mattress and pulling me with her. She arranged us with my back toward the door, and her body squarely toward me. I sat awkwardly with my legs tucked to one side, still clutching my modesty like my life depended on it. I had no idea what she planned next, and I was absolutely certain I didn't want to find out.

“Come on now, Blondie," she cooed. "Let's get comfortable. Spread out a little. You look so tense."

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 own legs over mine, effectively pinning me in place with the weight of her body. Her clothed torso was now merely inches from my naked one.

"There now," she said, her eyes drinking me in. "Isn't that better?" She held out her hands, palms up. “Give me your hands,” she requested.

Of course, it wasn’t a request. I hesitated, my fingers still clamped protectively over myself, but I knew better than to resist. Slowly, painfully slowly, I lifted my hands from my groin and placed them in hers. She gently guided them outward, pressing my palms flat on the bedspread just beyond my knees. I was fully exposed now, spread open for her inspection, which of course had been her intent all along. She could touch me anywhere now. She could see everything.

"Good boy," she praised. "Leave those hands right where they are. No more covering up your little wee-wee. I want it exposed so I can look at it while we talk."

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? Knowing I can see everything, and do anything I want with you. And just so you know, this is making me feel all tingly inside."

I had no answer. And the fact that my shame was a source of erotic pleasure for her only deepened my humiliation. 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. “I asked you a question. Answer me, sweetie.”

"Y-Yes," I stammered. "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 still. “You know it’s true, don’t you? That’s why he’s here tonight. Just to see you, right? To feast his eyes on our pretty little Blondie?” 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? That silky nightie hardly covers anything. You might have to fend him off."

“Please...” I begged, not even sure what I was begging for anymore. Mercy, I guess.

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

“No!” I snapped, my head jerking up in sudden panic.

Felicity smiled, clearly pleased by my outburst. “Okay, relax, Blondie. I won't make you go out there all naked." She patted my knee with condescending gentleness. “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," I managed, my voice cracking. "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. Going to drive him absolutely wild. 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? Wax them? Did someone do it for you?”

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

"Would you rather talk about what Mitch might do when he sees you? Shall we go into detail?"

Instead she lifted my arm and gave it the same treatment, sliding her fingers up and down my bicep. “Such smooth, girlie arms. Pretty, pretty,” she teased, dragging out the t sound with a musical taunt. I fidgeted under her touch, feeling increasingly 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. "I'll have to thank them."

She looked lower, then reached down to gently tug on a few strands of my pubic hair. The sensation was shockingly intimate, and I flinched hard enough to shake the mattress. Felicity just smiled. “Why did they leave your hair down here?” she asked, her voice curious. I didn’t answer. I just stared straight ahead, desperately hoping 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. A smile slowly stretched across her face. She’d struck a nerve, and she knew it. She left the topic alone for the moment, but I had a haunting, sinking feeling that 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 again, much to her delight. She knew exactly 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 somehow 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. Do they point and laugh at you?" She leaned closer. "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," she said, grabbing my hands again and giving them a playful bounce on the mattress. "I'm monopolizing the conversation again. Tell me about the showers. Tell me about the jokes."

“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. Two and a half, tops.”

“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?” she pressed.

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

She smiled, and for a moment I thought she might actually show mercy. "Okay," she said agreeably. "Tell me the story about the auditorium."

I probably would have been more comfortable talking about my penis. "What story?" I asked, and I knew even as I spoke that my body language had already betrayed me.

“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?” she asked, her voice rising.

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

"Dark," she repeated. "How fortunate. How utterly terrifying all the same." She paused, seeming to picture the scene in her head. Judging by her smile, she was enjoying it. “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? Did they all see everything?"

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

She pointed between my legs again, her finger hovering a terrifying inch away from my privates. “Shall we remove that unsightly hair before we go out there, sweetie? Make you nice and smooth for everyone?"

My eyes snapped wide again. “Please, no... please don't...” I begged, before I could remember that begging only fed her appetite.

“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. Smarter, maybe.”

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 harbored 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? Something not very nice, I recall."

And just like that, I knew right then 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. Chop chop, Blondie.” 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, my hands flying to cover myself. “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—the naked boy on his knees, begging for mercy from the clothed woman with the scissors. "Please, Felicity, I'm begging you, one last time..."

“Oh, for heaven’s sake, how pathetic,” she said. She reached out and grabbed a few strands of hair from my head, feigning a cut with the scissors held close to my scalp. "Fine, we'll just start here and work our way down."

"Okay! Okay!" I cried, scrambling to my feet, my hands raised in surrender.

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 think that could work nicely." I nodded gloomily, my stomach twisting into knots. “Great! We’ll use the same tune, but we’ll plug in our own lyrics. Something more... appropriate for the occasion. 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... ♬

She paused, savoring my horror. "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! Get it right, Blondie. 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, my voice cracking. Felicity gave me a look of admonition, the scissors twitching in her hand. 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, struggled to keep singing while she systematically stripped me bare.

♬ “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. "Even better than I imagined!"

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, prolonging my shame—and likewise, her entertainment.

"Let's do it again!" she said excitedly, clapping her hands together.

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," she announced. "While you sing. You'll see, it's really fun!”

I stared at the scissors in my hand, then at her, my mouth working soundlessly for a moment. 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. "Just sing. And snip. The song makes everything better. Trust me."

I groaned, and after a long, tense silence and a deep, reluctant sigh, I surrendered. What choice did I have? I began to sing, while she crouched down and put her head close to the action, her eyes wide and fascinated. 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.

"Good boy, Blondie!" she encouraged, as if I were a toddler taking his first steps. "You're getting the hang of it! See? Isn't this fun?"

When I finally finished the song, she clapped her hands with genuine delight 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," she announced, snatching the scissors back. "Hold your little wee-wee out of the way, and start singing." She positioned herself, then paused, a new thought apparently occurring to her. “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 my voice grew hoarse and there was truly 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 nose in distaste.

"Not good enough," she declared, shaking her head. 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," she explained, her tone conversational, as if we were discussing the weather. "This will make it easier, and you'll be really smooth. Silky smooth. That's what we want, isn't it?"

Before I could even process whether that was a rhetorical question, she retrieved Becky's pink razor and some shaving cream from the shower and pressed them into my hands. “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. He'd probably love to help." She chuckled at the look on my face and handed me the hot, damp cloth. “Here, hold this over that stuff you have left for a couple of minutes.”

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

"Ticklish?" she giggled.

"I... please don't." I stammered

"I think you've got a few hairs on your little balls," she continued, undeterred, "so wrap the cloth around those, too. We're going for complete, total, absolute smoothness here, Blondie."

She was making sure that I would be totally denuded, stripped of every last vestige of adult masculinity. 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. I wanna see,” she ordered, all too eagerly. I reluctantly obeyed, and her grin widened instantly. “Now it looks just like Joey’s,” she teased, cackling as I turned what felt like crimson from head to toe, my entire body flushing with shame.

"Come, let's have a look in the mirror," she said, taking my hand in hers.

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, the smoothness below my waist making everything about me seem smaller, younger, and vulnerable. I wanted to cry, but I was beyond tears.

“Well, would you look at that,” she said, admiring me with her head tilted to one side. “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 a sweet lullaby.

♬“Blondie's pee-pee has no hair, ee-eye-ee-eye-oh...” ♬

Then she beamed. "How does it feel to have a hairless little pee-pee, 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. “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? Having everyone see your panties? That would be so embarrassing."

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

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

Felicity blinked, her expression going blank for just a moment, then she 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 to the cool air “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 growing sense of dread.
Last edited by Blondie on Wed Sep 02, 2026 9:33 pm, edited 7 times in total.
BABYRYAN2121
Posts: 57
Joined: Sun Aug 14, 2022 2:34 pm
Been thanked: 44 times
Contact:

Re: Roosevelt Humiliations

Post by BABYRYAN2121 »

as always... the best SPH!!!
steam train
Posts: 216
Joined: Sat Nov 18, 2023 11:32 pm
Has thanked: 860 times
Been thanked: 488 times
Contact:

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.
Post Reply

Who is online

Users browsing this forum: Ahrefs [Bot], Bing [Bot] and 17 guests