Roosevelt Humiliations

Stories about boys ending up in compromising situations, preferably naked and embarrassed, as the name suggests.
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Blondie
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Roosevelt Humiliations, Chapter 20

Post by Blondie »

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Chapter 20: Petticoated

A Peek Inside the Panties

Julie led me through the hallway and into Becky’s bedroom with her right arm around my bare shoulders. In her other hand she carried a large Victoria’s Secret tote bag. Felicity, her spunky little sister, followed closely behind.

Julie let go of me in the middle of the room and continued walking, laying the bag on the double bed. I remained where I was, still feeling quite ashamed in the panties and long nightgown. Felicity stood facing me with a grin on her face, clearly enjoying my discomfort.

“Is this where we get to make Blondie get naked?” she asked, eyes glued to my mortified face.

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

Julie continued going through her bag. “Let’s see now, what have we got in here for our little girlfriend?” I turned my head slowly towards the bed, dreading what I was about to see. My dread was not unfounded.

"Ah, here we go. He’ll look just divine in this,” as she pulled out a little girl’s party dress and held it up for us to see. It was baby blue, with a short, wide skirt and short, puffy sleeves. I was aghast as my eyes widened and my mouth opened in horror.

“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 that you should wear a festive little girl’s party dress.”

She draped the dress on a hanger and hung it on the back bedpost, then started sifting through her bag again. I couldn’t take my eyes off the dress, as I was almost awestruck at its significance. The next words from Julie’s mouth diverted my attention.

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

Julie watched our reactions closely. One was of utter anguish and the other of extreme delight.

“You betcha!” squealed Felicity, her eyes twinkling with mischief as she reached for the spaghetti straps of the nightgown and pulled them off my shoulders.

I instinctively recoiled, with my arms firmly across my chest.

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

“I got this,” Felicity interrupted with confidence, wagging her finger in my face. “Okay, Blondie. Either you lower your arms and cooperate with me right this instant or I’ll call the girls in here and the seven of us will take off your nightgown, pull down your panties and take turns putting you over our knees and giving you an embarrassing spanking that you’ll never forget. Then you’ll model your pretty new party dress for us anyway. So it’s your choice: You can play nice and make this easy or you can be obstinate and earn yourself a humiliating spanking. Either way,” she said as she pointed at the dress, “You’re going to be wearing that dress when it’s all said and done. Now which way would you like it?”

The precocious little thing was a monster.

I glanced quickly over at Julie, who was beaming at her younger sister’s performance.

I bowed my head and lowered my arms in subjection.

“That’s more like it,” Felicity chirped, thoroughly satisfied with herself.

She gently tugged the straps from my shoulders and let go, stepping back to witness the natural descent of the nightgown as it pooled around my ankles. The tips of the fingers of both of her hands sprang to her lips as she let out a squeal of 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, absolutely tickled.

I could only cover myself with my hands, cheeks blazing.

“Well, well, what have we here?” asked Julie rhetorically as she approached me with a demonic grin on her face. Up until then she had been just a very interested spectator. That was about to change. She knelt and lifted my feet one at a time to separate me from the nightgown.

“My, my, look at these pretty legs,” she observed, brushing her fingers up my calf in a slow, appraising stroke. “Felicity, come feel how smooth Blondie’s legs are.”

Of course, the little fiend didn’t need any further prodding.

“Ooh, you’re right, Julie,” she cooed as she stroked my other leg. “They’re so smooth and pretty, like silk.”

I wanted to die on the spot.

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

I said nothing, staring miserably at the floor.

She raised her arms and interlaced her fingers behind her head, elbows wide. “Go like this, Blondie, I want to see something.”

I hesitated, but I knew there was no use resisting. I complied. Julie giggled.

“Just as I thought—not a hair anywhere,” she said as she looked at my smooth underarms.

I stood there, frozen, 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 with a devilish glint in her eye.

To my horror, she hooked her finger into the front of the panties and pulled the waistband outward, then peered in. Her smirk widened. “Well, at least you’ve got some hair,” she teased, before letting the elastic snap back. She turned, chuckling, and sauntered back toward the bed.

“I wanna see, I wanna see!” Felicity chimed in gleefully.

I drew back my hips as Felicity reached for the elastic. The notion of the thirteen-year-old looking at my private parts against my will was just too much.

“Blondie?” she warned with an admonishing look.

I stood straight and submitted to the mischievous sprite. Eyes squeezed shut, I braced myself as I felt the elastic pull away again. Her hair tickled my stomach as she peered down. I kept my eyes closed, but the vision of her staring down the panties was fixed in my head.

After an agonizingly long time, the elastic snapped back.

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

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

Julie laughed boisterously and walked over to me, addressing me while looking me in the eyes. “In case you’re wondering, Blondie, Joey’s our little brother. He’s ten.” Both girls laughed uproariously, while I blushed crimson.

“I assume it’s supposed to get bigger as boys get older. Right, Blondie?” Felicity directed the question at me, but I didn’t answer. She knew she had struck a nerve, and she milked it for all it was worth. “How old are you, Blondie?” she persisted. She stared at me, waiting for an answer. I answered, hoping to speed the interaction to a conclusion.

“Sixteen,” I said softly while averting my eyes from her.

“Well, except for the hair, you look like you’re ten, judging from what’s inside your panties.” Both girls laughed again as I turned yet another shade of red.


The Petticoat

“Okay,” Julie said, clapping her hands together. “Time to get 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 with a string at the top. I looked on with angst as she started untying the string. She continued teasing me as she reached into the bag.

“Do you know what it means to be ‘petticoated,’ Blondie?” she asked sweetly. I didn’t answer. I couldn’t.

“It’s an old-fashioned term for putting a boy in girls’ clothes, usually against his will,” she continued, pulling out something white, fluffy, and terrifying. “In this case, you’re about to be petticoated in the literal sense.”

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

“Don’t worry, sweetie," she teased. "You’ll look gorgeous in your new finery. Little girls can’t expect to wear their party dress without their petticoat,” 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, practically bouncing with excitement.

She lifted it over my head and tugged it down, adjusting the shoulder straps and fluffing out the skirt. She stepped back and looked me up and down.

“Oh my gosh! You must come see, Blondie!” She grabbed my hand and led me to the full-length mirror.

What stared back at me was a very red-faced sixteen-year-old boy adorned in a frilly, fluffy, short white petticoat that flared out like an umbrella, short and poofy and horrifically feminine. I stared at myself in disbelief.

Julie appeared at my other side. “Oh, he looks adorable,” she purred. “What do you think, Blondie, are you getting in touch with your feminine side?”

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

“Come, my petticoated one,” Julie teased, leading me back to the bed. “Let’s finish your outfit.”

The petticoat made an audible swish-swish as I walked, adding to my mortification. Julie patted the mattress, gesturing for me to sit. I did, and instantly regretted it as the skirt shot up high, prompting another delighted squeal from Felicity. She ducked down, trying to peek underneath. Mortified, I clamped my knees together and pressed the petticoat down with both hands—realizing to my disgust I had just done exactly what a little girl would’ve done. Felicity noticed.

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

“Let’s finish dressing our little sweetheart,” Julie laughed, plopping beside me.

My humiliation continued as I was being treated like a little girl, unable to dress herself. Julie picked up my foot and laid it on her thigh, slipping a frilly white anklet onto it. “Just like the ones Becky and Brenda had you wear at the mall, remember?” she said sweetly. “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 here while I put on her shoes. I grimaced at hearing Julie refer to me as a “her.”

While Felicity worked the other anklet on my right foot, Julie produced a shiny, black, patent leather pull-on shoe with a buckle. She must have noticed the look of despair on my face.

“What’s the matter, Princess, don’t you like your pretty new Mary Janes?" she asked, voice syrupy sweet. "They’re brand new. Becky told me your size, and it looks like they're a perfect fit.” She handed the other shoe to Felicity, who eagerly applied it on my other foot, and once I was buckled in, she took my hand again.

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

Back at the mirror, a distraught, red-faced boy in a petticoat stared back at me, only this time he was wearing frilly anklets and 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 down over my head. I watched with incredulity as the hem of the dress dropped down, coming to a halt about an inch above the petticoat. Julie zipped me up from the back while Felicity fussed with the sleeves and hem.

Then came the pièce de résistance—Julie pinning a giant baby-blue bow to the top of my head. She adjusted it with precision until it stuck out just right. I wanted to sink through the floor.

“Ohhh, Blondie,” Julie sang. “You look absolutely angelic!”

Both girls began fiddling with the dress, adjusting the sleeves and the hem of the dress to their liking. I was utterly miserable as I stood there and took in the latest humiliation. But it wasn’t over.

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


Ruffled Panties

Felicity was all too happy to comply. I felt violated as she kneeled, reached up my dress (oh my God, I just called it my dress—I mean the dress), and in one swift motion pulled the panties down to my ankles. I involuntarily flinched at the invasion.

I flinched again when she reached under the petticoat to peek. She looked up at me and grinned, while I blushed redder again.

Just then I saw the reflection of a new pair of panties being stretched out by Julie above my head. They were very frilly, with ruffles across the rear.

“Time for your frou-frous, little girl,” giggled Julie as she kneeled at my feet. I complied subserviently by lifting my feet (hey, what else could I do at this point?), and she pulled the little girlish panties up my legs.

When she was done, she gave me a gentle, cheeky squeeze between the legs, causing me to jump and let out a high-pitched squeal. It was like a little girl’s squeal. Both girls howled with laughter.

Julie then turned me around, so my back was facing the mirror. “Turn your head and take a look, sweetie,” Julie directed.

I did so, and to my dismay I noticed that a couple of layers of ruffles from the panties showed below the petticoat and dress. When I tried to tug the dress down, it popped right back up.

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

I winced, realizing that even more of the panties would show as I walked around, not to mention how many layers would be exposed if I bent over. I tried to repel it, but a tiny tear started rolling down my cheek. Julie, feigning compassion, stepped in close and gently wiped it away.

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

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

But Julie just smiled. “Now, now,” she said, as she took my hand. “I think the best medicine for you is to go out to the party and play with your friends. Felicity, take her other hand."

“No, please!” I whimpered.

But the door was opening, and I was being led forward—petticoat swishing—as they pulled their reluctant little doll toward the party.

“Please, no!” I begged. The two of them tried to lead me through the doorway. I just couldn’t go through with it, and I held back, resisting the tug on my hands.


A Spanking

“All right, that does it, I’ve had just about enough of you, young lady!” Julie yelled at me, as if she was really upset. In retrospect, I think she was looking for an excuse to spank me. She reached over to the dresser and grabbed a hairbrush.

“Pull up her petticoat, Felicity.”

“No, please!” I yelped in protest, but Felicity was already behind me, happily flipping up the fluffy white layers.

“Pull down her panties,” Julie said.

“No! Nooo!”

My pleas just added fuel to their fire as Felicity yanked the panties down to my knees and held the petticoat up my back. I knew that to resist any more would only make matters worse.

I barely had time to breathe before—Whap! Whap! Whap! Whap! Whap! Whap! Six sharp blows in quick succession from the back of the hairbrush smacked against my ass, three on each cheek. It took a few short seconds for the pain to register, but when it did.…man, I’m here to tell you that it throbbed furiously.

“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’ve looked completely ridiculous—jumping up and down like that, with frilly panties dangling at my knees, and the petticoat and dress raising up and down with each jump.

When the pain finally began to subside, I pulled the panties back up with shaky hands. Julie wiped a tear from her eye—from laughing too hard.

“Oh, God, Blondie, that was too funny. I’m sorry the girls missed that one." She leaned in with a mischievous glint in her eye. "Now, are you ready to come join the party or do we have to discipline you further?” There was silence. “Answer me, Blondie.”

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

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

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 straighten my hair, though it was fairly short. When she spotted a stray tear, she brushed it from my cheek with the front of her index finger.

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

That didn’t help.

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

Julie took one hand, and Felicity the other. This time I didn’t resist, and I was led through the hallway in my wretchedness. When we entered the living room—well, I’m sure you can well 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 smooth, girly legs!”

“How adorable!”

“Poor little baby, she’s been crying!”

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

After the noise subsided somewhat, the girls really started having their fun….

* * * * * *

I’ve really gone on much longer than I intended to, and it’s been painful enough, so I’m not going to go into detail of what went on for the next hour or so. But here’s a quick rundown of what I was made to do while dolled up in that wretched party dress—and yes, two separate threats of a bare-assed spanking did get me moving when I hesitated:

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

—Play “Patty-Cake” with Marcia (who insisted we do the full routine—twice).

—Perform the entire “Hokey Pokey,” frilly skirt bouncing with every twist.

—Perform “I’m a Little Teapot.”

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

I think you get the picture. It was total, unrelenting humiliation.

Unfortunately, the night was still young, and the sadistic seven, who were in their glory, had plenty more degradations in store for me.

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

I will tell you this much right now: I’d gladly take the petticoat treatment again over what came next.
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