Roosevelt Humiliations

Stories about boys ending up in compromising situations, preferably naked and embarrassed, as the name suggests.
steam train
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Re: Roosevelt Humiliations

Post by steam train »

… and of course as an avid reader of your works, I know that much later Felicity is caught out …

“Felicity gets her due comeuppance in a different form. Later in life (in her twenties), she is at the mercy of an unscrupulous psychiatrist, who puts her through some very humiliating ordeals. Her humiliations are chronicled in a story called The Satanic Psychiatrist.”
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Roosevelt Humiliations, Chapter 23

Post by Blondie »

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Chapter 23: Shake That Ass!

Yet More Feminization

“I think it’s time we go join the party, Blondie,” declared Felicity with a gleam in her eye and a devilish smile. “Your adoring fans are anxiously waiting. I’m sure Mitch can’t wait to see you.”

She shot me a sly glance, clearly amused by my blushing face. As if to put an exclamation point on my humiliation, she lifted the hem of my babydoll for one last peek at my now-smooth genitals. “You’d better be careful out there, Blondie,” she warned. “Or someone might discover our new little secret.” She paused for effect. “And little is the operative word.”

Still giggling, Felicity took my hand and led me down the hallway. My sense of dread was extreme, and, as you will soon see, this dread would prove to be well founded.

The moment we crossed the threshold into the living room, the group erupted. I was welcomed with an exuberant outburst from the reveling group. Becky was the first to greet me. “Oh, look at you in your babydoll!” she teased. “You’re just adorable!” Before I could retreat, she seized my hand and led me toward the couch where Mitch sat waiting. As I walked, I kept tugging at the hem in a futile attempt to shield my thighs.

“Blondie, it’s a pleasure to see you,” Mitch said, eyes lighting up as they roamed unabashedly over my bare legs. Slowly, deliberately, he reached out and traced his fingers up my leg, starting at the ankle. When he reached my thigh, I jerked away reflexively, blushing furiously as the girls broke into a chorus of laughter.

“That Blondie,” Brenda quipped. “Always playing hard to get.” She beckoned from the other side of the L-shaped couch. “Come over here, sweetie—I’ve got a little surprise for you.” I shuffled toward her with dread in every step. She patted the cushion beside her. “Have a seat, Princess.”

I sat, rigid and wary, vigilantly tugging on the babydoll’s hem as I leaned back. No sooner had I settled in than Brenda reached into her purse and pulled out a tube of bright red lipstick.

“We need to pretty you up just a bit more, sweetheart,” she cooed. "I know you want to make a good impression for your new boyfriend, don’t you?” I turned away, looking at the floor in silence. But Brenda wasn't having it. She gently turned my face toward hers with a tilt of her fingers beneath my chin. “There’s my pretty little thing.”

She uncapped the lipstick and meticulously began painting my lips. As she worked, Julie scooted up next to me and started trailing her fingers up and down my bare left thigh. “Oh, Blondie, I just love your legs," she said playfully. “So smooth. So silky.”

The other girls joined her giggling, and somehow I managed to blush brighter, which was not lost on Brenda. “Well,” she said, “no need for blush—you’re doing that part all on your own.” She returned the lipstick to her purse and pulled out some more makeup. “Time to enhance your pretty eyes, girlie-boy.” As I sat there, resigned and thoroughly mortified, she applied light blue eyeshadow to my lids, followed by mascara to my lashes. Julie, meanwhile, was strumming her fingers up and down my hairless arm.

“I love your little girlie arms, Blondie. So dainty. So cute.” More giggles.

When Brenda finally stepped back and tilted her head to assess her work, she looked genuinely pleased. “Oh, my gosh, you look gorgeous,” she teased. “I’m so jealous—you look prettier than I do!”

I remember thinking that it was scary, but she was probably right. She was in old jeans and a sweatshirt, and here I was, smooth and silky, in a short, sexy nightie and becoming more feminized by the second.

Brenda wasn’t quite finished. “Just one last touch, sweetie pie,” she said, as if struck by a brilliant idea. She reached into her bag once more and pulled out a tiny spray bottle. “Tilt your pretty head back for me, Princess,” she said, gently lifting my chin. “There we go, good girl.” She sprayed some perfume to the base of my neck, then lifted my wrist and sprayed the inside. Then, leaning close, she gave my neck a gentle sniff. “Mm, mmm. You smell delicious, Princess.”

She gave the side of the babydoll a playful tug. “You better watch out, Blondie," she warned, eyes twinkling. "Mitch might just rip this thing off and ravage you right on the spot!”

The giggling escalated to boisterous laughter, sending me further into the depths of mortification.


Shake that Groove Thing

When the laughter finally began to die down, the ever-energetic Felicity bounced in front of me and seized both my hands. “Come on, Blondie, you have to see how pretty you look!” she declared with excitement.

Before I could protest, she was dragging me across the room to a tall, decorative mirror by the fireplace. As Felicity stood next to me, beaming, I caught my reflection and almost recoiled. The combination of the smooth, hairless skin, the pink ruffles of the babydoll, and the makeup created a vision so foreign—and so humiliating—that I could barely accept the person in the mirror was me. In the background of the reflection, I saw Mitch. He was staring at me, with a lecherous grin on his face that made my skin crawl.

Felicity wrapped her arms around me and kissed my burning cheek. “Ohhh, Blondie, you make such a pretty young lady! I feel like I’ve found a new girlfriend tonight.” She giggled, then reached down playfully toward the hem of the babydoll. “Of course, I could pull this up, and we’d all see that you’re really a pretty little boy.”

Panicked, I swatted her hand away as she burst into laughter, clearly pleased with herself.

“Can you show Mitch your fancy froufrou undies?” Marcia chimed in mischievously.

My stomach sank. Felicity and I both knew the truth: She hadn’t let me put anything on under the babydoll. I stood stiffly, hoping no one would press the issue.

No such luck. “Oh yes!” added Joanne, clapping her hands. “Show us your pretty panties again!”

“Hold on, I’ll be right back!” Felicity sang, skipping off down the hall. She returned instantly, dangling the panties in question high in the air, her grin wicked.

“Whoah!” came the outcries from the party guests, as they realized the significance of Felicity’s actions.

“Wait... does that mean...?” Cheryl asked, her eyes wide.

She was interrupted by the impish Felicity. “Let’s just say that if we took off Blondie’s babydoll, then he’d be wearing nothing but a bright blush on his face.”

“Oooooh!” Mitch and the girls chorused, delighting in my predicament.

It was at this point that Brenda had a lot to do with worsening my already pitiful plight. “Are we sure he’s not wearing a different pair of panties under there, girls?” was her simple, but provocative question. Of course, it was a question that they all pounced on.

“Come on, Blondie,” my sister Becky coaxed, “Let’s see whatcha got going on under there.”

The girls joined in noisily in agreement. I didn’t stand a chance. Felicity led me to the center of the room, just feet away from Mitch. She positioned me facing away from him, then leaned in close, her eyes dancing. “So, Blondie,” she teased, “shall we give everyone a peek and clear up the mystery?”

“Please, no!” I pleaded, the first words I’d spoken since she dragged me out there.

Naturally, my appeal fell on deaf ears. “Hands on my shoulders, Blondie,” she said. My arms trembled as I obeyed. She whispered in my ear. “Are you ready to show Mitch your cute little tushy?” she teased, and in my fear my breathing became faster.

She reached around me, taking hold of the back hem of the nightie. “Look at me, Blondie.” When I did, she raised the back of the babydoll halfway up my back—and just like that, my bare, hairless bottom was on full display to the entire room.

I squeezed my cheeks together instinctively as a wave of cheers, squeals, and laughter erupted. I glanced at Felicity, her face practically glowing with excitement over her latest stroke.

“Look in the mirror, Blondie,” she cooed.

I took a glimpse at the reflection. There they all were—grinning, pointing, and laughing at my exposure. A sick feeling came over me as I swear I saw Mitch make an adjustment to his crotch.

“Let's give ’em a little show, Blondie,” Felicity prompted. “Swivel those hips for us.” Before I could protest, she placed her hands on my waist and helped me rotate my hips in a slow, humiliating circle. I could only imagine the display I was putting on. It was humiliating enough in front of all the girls, but the knowledge that Mitch was almost certainly deriving a sexual thrill from my performance made it just about unbearable.

“Becky, put on some music!” yelled Brenda excitedly.

Becky, not one to let an opportunity go by, sprang into action and popped a Jennifer Lopez CD into the stereo. The beat of “Let’s Get Loud” filled the room.

“Shake it, Blondie! Shake that ass!” Brenda shouted.

With the beat pulsing and the girls chanting my name, I reluctantly began to sway. It was clumsy, awkward, and absolutely mortifying.

“Faster, Blondie! Work it!” they chanted, voices full of amusement.

My hips moved in a frantic rhythm, every shake drawing another burst of whoops and laughter from my audience.

“Oh, I have to see this!” Felicity exclaimed. “Here, Blondie—hold this up for me."

Heat rushed to my face as I reluctantly reached back, gripping the hem to keep myself bared. The shame I was feeling slowed me down for a second.

“Keep shaking it, Blondie!” Felicity barked from behind me. “Faster, faster!”

Smack! Smack! Two sharp swats landed on my ass, forcing my hips into motion, while the cheers behind me reached a fever pitch.

“Go Blondie! Go Blondie! Go Blondie!” the girls chanted derisively, clapping to the beat. “Shake that ass!” “Make it bounce!” while I continued shaking my hips to the music, much to the delight and entertainment of my sadistic tormentors.

* * * * * *

I’ll have to stop here for now. I need some time to gather myself—to summon the courage to tell you about what else happened to me during the most humiliating night of my life.
Last edited by Blondie on Tue Mar 31, 2026 8:38 pm, edited 5 times in total.
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Re: Roosevelt Humiliations

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fantastic! thank you!
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Roosevelt Humiliations, Chapter 24

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Chapter 24: Hairlessness Revealed

High Heels

I continued shaking my hips back and forth to the music, holding the babydoll up my back. With my bare ass exposed, the delighted spectators goaded me on. “Go Blondie! Go Blondie! Shake that ass!” they yelled with glee.

When the music finally faded I let the babydoll fall, breathing hard and blushing furiously as the applause erupted.

“Bravo, Blondie, Bravo!” shouted Felicity. The laughing thirteen-year-old turned me around to confront the entertained audience. My eyes caught Mitch's leering grin, which made my cheeks burn even hotter. That’s when I noticed Julie fishing through her infamous bag of tricks. A wave of dread washed over me when she pulled out a pair of pink high-heeled shoes. I had a pretty good idea they weren’t for her.

“These’ll match your cute little nightie perfectly,” she said, beckoning me forward with a wicked grin. I reluctantly stepped up to her. Julie gently lifted my ankle and slid on one of the heels. “Ah, a perfect fit,” she said with delight. “These will set off those pretty legs quite nicely.”

Her hand lightly caressed my smooth calf, making me shiver. The second shoe followed, and as she set my foot down, I wobbled, lost my balance, and toppled forward—hands landing on Julie’s shoulders for support. Julie pounced on the situation by grabbing my wrists and leaning prone on the couch, pulling me down on top of her. I felt the babydoll riding up in the back, much to my chagrin. I tried to get up, or at least tried to cover my ass, but Brenda had taken a good hold on my wrists. Julie playfully tugged the babydoll all the way up to my shoulder blades. Her legs were wrapped around my thighs to keep me from sliding off. And just to make sure no one would forget the moment, a camera flash lit up the room.

Julie started pumping her pelvis back and forth, forcing my hips to bounce rhythmically against hers. “Help, I’m being attacked by a lesbian!” she screamed, which sent everyone into another fit of hysterical laughter. I frantically tried to escape from the compromised position, but Brenda held fast.

My exposed ass must have been a tempting target, for I started feeling the stings from the slaps of one of the girls. “Bad girl, Blondie, exposing yourself like this. Bad girl!” scolded Felicity as she spanked me at a hard and steady clip. My hips continued to be forced up and down while she continued with her relentless slaps. “Have you no shame?”

Oh, I had shame all right. Enough to last a lifetime.

“Ow! Ow! Ow!” I screamed when the stinging from the smacks hit home. “Please, let me up!" The pain was bad, but the humiliation was far worse. What a sight I must have been, with my legs kicking wildly, wearing pink high heels.

“Be careful, Blondie, you’ll smear your lipstick,” I heard Cheryl say through her laughter.

Felicity gave my backside one last swat for good measure. “Ooh, look how red his little fanny is getting,” she said approvingly.

“Whoa, check that out!” Joanna chimed in.

Becky ran a hand across one of my cheeks. “Oh, wow, feel how warm it is!” she exclaimed.

Of course, they all had to put their hands on my ass, all agreeing that indeed it was quite warm to the touch. The worst was when Mitch took his turn. Not content to just lay his hand on me, he rubbed his fingers all over, sliding along the crack, brushing across my butthole, and stroking my perineum, causing my whole body to flinch.

Julie, with whom I was still face-to-face, felt the flinch and noticed my look of open-mouthed surprise. “I think he just got goosed,” she laughed. “I think you’re getting Blondie excited, Mitch."

Mitch, playing the crowd to the hilt, jumped on top of me with his legs on either side of me, his midsection over my ass. He started pumping his hips back and forth, simulating a butt-fucking. Raucous laughter filled the room.

“Ew, gross!” cried Felicity, but her laughter betrayed her true feelings. She clearly was enjoying the scene, and my humiliation.


The Catwalk

“We’d better get you up before you get molested, Blondie,” Julie said, laughter in her voice.

The grinning Mitch backed off, and Julie and I sat up on the couch. I immediately adjusted the babydoll, pulling the hem down as far as it would go, which was only to the top of my thighs. My face felt like it was on fire.

Julie stood up and took both of my hands in hers. “Come, my blushing little girl. We need to teach you how to walk in your new heels,” she said cheerily. “Birthday girl—care to assist?”

Felicity needed no further prompting. “With pleasure!" she replied, grabbing my other hand. Together they led me across the room as the rest scooted to make space for the impromptu runway show. Mitch and the other five girls all sat on the couch, anxiously awaiting the demonstration, while Julie and Felicity began walking me away from the captivated audience.

“Okay, sweetheart,” instructed Julie. “When you walk, you should take very short steps. Put one foot in front of the other, as if you’re stepping on an imaginary line. Like this.” She demonstrated her womanly gait. I noticed that her hips naturally swayed seductively from side to side when she walked.

“Now you try it,” Julie directed. She took my hand again and the two of them put me through my paces. “That’s it, sweetie,” praised Julie. “Nice, short, mincing steps, just like that. Can you feel your hips swaying back and forth?” She was tilting her head back, watching my backside. “'Cuz I'm here to tell you—you’re sashaying like a lingerie model on a catwalk right now.”

Again, boisterous laughter filled the air. We walked across the room, turned, and headed back. My steps were clumsy at first, but slowly I found my rhythm. Sort of.

My face was glowing as I approached the grinning assembly on the couch. We stopped right in front of them. The devilish Felicity had another debasement up her sleeve for me. “Such a lovely little model,” she teased. “How about a curtsy for your adoring fans?”

The grins from the faces on the couch grew wider. Julie and Felicity let go of my hands, stepping to the side and watching expectantly. I wobbled momentarily, then I stood there awkwardly, staring at the ground. But I knew what I had to do. I reached for the hems of the babydoll and performed a shy, blushing curtsy.

“Not bad!” said Felicity. “But let’s try it with some eye contact. Again!”

Difficult as it was, I repeated the ignominious act, this time while looking into the eyes of my leering tormentors, face glowing crimson.

“Nice curtsy, Blondie,” approved Felicity. “Now it’s time to strut your stuff again.”

As we turned to walk back across the room, Julie leaned forward and whispered something to Felicity, who responded with a childish giggle. I knew this couldn’t bode well for me.

“I think our girl’s ready to walk on her own,” said Julie. “You’ve got this, Princess.”

I started walking—okay, mincing—across the room solo. But before long, I felt the back of my babydoll lifting up again.

“Look, his butt’s still all rosy,” laughed Marcia.

“And look at it wiggle!” added Joanna, laughing. “Oh, this is a riot!”

The teasing comments poured out as I walked to the other end of the room, where Julie and Felicity mercifully let go of the babydoll.

“Okay, cute cheeks, you can turn around now,” instructed Julie. I rotated and started walking back toward the couch. At least they didn’t lift the front of the babydoll on my way back. The frontal exposure would have been mortifying enough, but since Felicity shaved off all my pubic hair (a fact which everyone was unaware of, save for Felicity and me), I absolutely didn’t want anyone to see me like that.

I reached the couch, and dutifully curtsied. My face flushed intensely. “I just love the way your brother blushes, Beck,” offered Brenda.

“Me too. Just like a little girl,” responded Becky with a giggle.

I was sent back for another lap, the nightie hiked up behind me once more. This time I was conscious of the sound of the high heels clicking on the hardwood floor, which was just another reminder (not that I needed one) of my forced feminine servitude.

I reached the far wall and turned, expecting the return trip, but Julie held up a hand to stop me. She had a new set of instructions.

“Okay, sweetie,” she smiled. “This time, as you walk back, I want a little more flair.” She demonstrated the pose: one hand behind her head, elbow jutting out, the other fist resting on her hip. “Go ahead, sweetheart, just like that. And swivel those little hips of yours while you mince.”

I followed her command, much to my mortification. As I approached the group on the couch, their enjoyment level was obvious.

“Look at him!” exclaimed Cheryl. “Oh, this is just precious! Go, girl! Sashay! Sashay!”

“Shake it, Blondie, shake it!” chimed in Brenda.

I reached the couch, performed the mandatory curtsy, and turned to start the loop again. This went on for quite a while, until my situation took a decided turn for the worse, impossible as that may seem.


“The Secret” Revealed

It happened at the end of one of my strolls to the other side of the living room. Julie and Felicity were waiting for me. Felicity had a mischievous grin on her face. “Blondie,” she said, “When you get about halfway back to the couch, I want you to stop and turn around. I’ve got a little surprise for everybody.”

Our eyes met. Hers had a twinkle in them. Mine did not. I wasn’t sure exactly what she had in mind, but I was pretty damn sure that I wouldn’t like it. With dread, I walked (or as Cheryl put it, I “sashayed”) toward the couch. I reached the halfway point, but I didn’t stop, fearful of what might transpire, and holding out a false hope that Felicity would forget. Fat chance.

“STOP!” she hollered. “That’s fine, right there. Now turn around.”

I was about six paces away from the spellbound group on the couch. I turned my back to them and faced the two impish sisters. I was perplexed to see that Felicity had a coat hanger in her hand.

She slowly ambled toward me. She had a flair for the dramatic—she knew that all eyes were on the scene, and that her deliberate actions would only raise the already-high level of anticipation. She stood before me and simply looked me over with a playful smirk on her face. Julie, with a look of keen interest, had moved closer to the action, and stood a few feet behind her sister, facing me.

Finally, after an interminable silence, Felicity spoke. “It’s time,” she said. She looked me squarely in the eyes and smiled at the distressed look on my face. “You know what I’m talking about, don’t you Blondie?”

“Please, no...”

“Ah, but it’s time we let everybody in on our little secret.”

I glanced up at Julie, whose brows were furrowed in a look of confusion. At the same time, her expression was one of delicious anticipation. I didn’t look back, but I suspect that the six people on the couch shared Julie's expression.

“Please, Felicity...” I whispered, my voice cracking.

“Well,” she mused, “maybe if you ask nicely. You’ll have to get on your knees and beg.”

I immediately dropped to my knees, holding out a ray of hope. I folded my hands together and held them out, looking up at the thirteen-year-old. “Please, Felicity, I’m begging you. Don’t make me do it.”

“Tell me, what is it you think I want you to do?”

“Please... please stop.”

“Answer me, Blondie. What don’t you want me to do to you?”

The room was silent, save for a few muffled giggles. I knew I had to answer.

“Please... don’t make me take this off.”

The group behind me gasped and giggled. Joanna chanted, “Take it off! Take it off!” I heard the giggling behind me, and I couldn’t help but notice the grin starting to break out on Julie’s face.

“Ah, and pray tell, what are you afraid of everyone seeing, Blondie?” asked Felicity.

I couldn’t answer, and my silence forced her hand. She reached for the hem of the nightie with both hands. “Arms up.”

“No, please don't—”

“Arms UP, I said!”

I slowly raised my arms high in the air. In one fluid motion, she stripped the babydoll off, leaving me naked but for a pair of pink high heels. I immediately hunched forward, my hands frantically flying down to cover my crotch. Felicity calmly slid the nightie onto the hanger and hooked it onto an empty plant rope dangling from the ceiling. It swayed back and forth momentarily, seemingly mocking my nakedness.

She sauntered back over to me. I stared at her feet without looking up.

“Stand up, Blondie.”

I rose slowly, my fingers pressed tight over my hairless genitals. I glanced up at Julie, was now grinning from ear to ear, her eyes fixed on my midsection. I quickly averted my eyes from her.

"Make him turn around!" someone shouted from the couch.

"In due time, girls," smiled Felicity. "In due time."

"Okay, Blondie,” she continued. She was relishing the absolute control. “Since my sister was kind enough to introduce me to you tonight, I’ll let her be the first to see. Hands on your hips, Blondie. And look Julie in the eye."

“Please, Felicity...”

“DO IT!”

I had to obey. I met Julie’s gaze and moved my hands to my hips. My face burned with humiliation as I watched Julie’s face shift from shock to pure laughter, crumbling into giggles as she nearly fell over. “Oh, shit, this is too much!” she gasped through spasms of laughter.

“Hey, we want to see!” Cheryl yelled, as she and a couple of the others jumped from the couch.

“Hang on, you’ll get your chance,” interrupted Felicity as she held out her palm, motioning for them to stop.

The eager girls sat down, and Felicity wasted no time in fulfilling her promise. “Okay, Blondie, you know the pose. One hand behind your head, one on your hip. Elbows out.”

I grudgingly followed her order. I looked down at Julie, who was holding her stomach. A few of her tears of laughter had dripped onto the hardwood floor.

Felicity continued. “Now... turn around, and mince back to the couch. You’d better do it right. When you get there, just stand there and keep your hands right where they are. And look everybody in the eyes. Now go!” she ordered while giving my rear end a playful slap.

I slowly turned around and started mincing toward the couch. It was an excruciating experience, as one can well imagine.

“Oh, my God!” my sister shrieked. “Felicity, what have you done to poor Blondie?” She, like the rest, was laughing hysterically.

I reached the highly entertained group and stood there, as I was told. My face pulsated with heat.

"He's completely hairless!" Brenda shouted.

“And—oh wow—look how teeny his little weenie and balls are,” Cheryl laughed, pointing.

“He does have a teeny weenie,” Joanna concurred, somewhat matter-of-factly.

“A cleany-teeny-peenie-weenie!” Brenda added.

That broke everybody up. They were rolling around on the couch, lost in their state of hilarity. To this day I don’t know how I stood there and endured the abuse. At one point I risked a glance at Mitch. He was quiet, but he was kneading his crotch with a slow, rhythmic intensity. I quickly turned away, sickened. I stood there for what seemed like an endless amount of time, blushing so hard I felt like my ears were on fire.

When the laughter finally subsided somewhat, Becky spoke up.

“So, Blondie," she gasped, wiping tears from her eyes. How did you get so... so bald?”

The laughter picked right up where it left off. I stood there without answering, my gaze fixed downward. After a couple of minutes, Felicity dived back in.

“It’s hard to believe he’s sixteen,” she pointed out. “He looks just like my brother Joey down there.”

I knew what was coming next, but the majority of the group did not. Felicity paused while everyone waited for her to continue. Like a good comedienne, she waited just the right amount of time before delivering the punch line:

“Joey’s ten.”

The room practically shook with the sound of their laughter. The group on the couch leaned into each other, laughing so hard that they had trouble catching their breath. The scene played out for a few agonizing minutes. Whenever the laughter seemed to subside, somebody would repeat Felicity’s words, “Joey’s ten,” and the laughter would start all over again. They alternated between closing their eyes in their fits of laughter, then looking up at my glowing face, down to my hairless little package, then laughing yet again. And all I could do was stand there in the pink heels, soaking up a lifetime of humiliation.
Last edited by Blondie on Thu Apr 02, 2026 6:04 am, edited 5 times in total.
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Re: Roosevelt Humiliations

Post by BABYRYAN2121 »

unbelievable to read it all again!! you are the best!
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Roosevelt Humiliations, Chapter 25

Post by Blondie »

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Chapter 25: Shrinkage

Naked on the Barstool

When the laughter had finally settled, Brenda returned from the kitchen dragging a tall barstool. She set it down right behind me. “Have a seat, Smoothie,” she grinned. “Rest those weary little legs. We girls know how exhausting it is walking around in heels all night.”

I climbed up onto the stool, knees together, and leaned forward, folding my arms across my thighs in a feeble attempt at modesty. Naturally, Brenda wasn’t having any of that. She came up behind me and gently tugged me back by the shoulders until I was leaning stiffly against the backrest. “I want you to be comfy, Blondie. Just kick back, relax, and enjoy yourself.”

Right, like that’s even remotely possible.

She took my wrists and rested them lightly on the barstool’s arms. “That’s it... just rest your arms here.”

Next, she pulled my knees apart and hooked my ankles onto the leg rests on either side, leaving me exposed to the max. “We’re all friends here, sweetheart. What’ve you got to hide?” She glanced down, her smirk widening. “Very little, from the looks of things.” That quip earned a fresh round of animated laughter as Brenda settled smugly back onto the couch.

Once things quieted down again, Becky picked up the thread. “You’re awfully quiet, Blondie,” she said. “Say something. We never talk anymore."

Everyone perked up a little, leaning in to hear my voice. But I stayed silent—I wasn’t exactly eager to provide running commentary on my own humiliation. Naturally, they all knew that, too.

“We’d really like to hear about your alone time with Felicity a little earlier,” Becky prompted. “You two were gone a long time. Let’s hear all about it.”

The last thing I wanted to talk about was my one-on-one humiliation at the hands of Felicity. Of course, Becky knew as much. I remained reticent.

“Blondie, I don’t think you’re in any position to be obstinate right now. As you well know, Mitch will drop your naked ass downtown at the snap of my fingers. I don’t think you’d be interested in public nudity, especially now that you’ve got a bald little clitty.”

While I sat there blushing crimson, the room erupted in laughter again.

“Not only that,” she added when the noise simmered down, “we’ve got plenty of photos of you tottering around in those pink heels, plus a fantastic video that we’ll all be watching tomorrow night over popcorn. I do think that it’s in your best interests that these visuals don't accidentally get loose around Roosevelt High. Need I say more?” I shook my head disconsolately. “I didn’t hear you, little girl.”

I winced at the “little girl” reference. “No... I understand,” I finally relented, cheeks burning crimson.

“Good.” Becky leaned back and took a leisurely sip of her beer. “Now, when I came to tell you Mitch had arrived, you were in a very interesting position. Why don’t you tell us about that, Blondie.”

It was clear there was no escaping this. I spotted Marcia with the video camera trained squarely on me.

“Felicity made me take off my clothes,” I said, trying to keep it brief.

“I’m warning you, Blondie,” Becky said. “We want details. All the details.”

I took a deep breath. “When you walked in, I was standing on the stool. I only had the panties on at that point. Before that... she took off my shoes and socks, the dress, and the petticoat.” I paused, fidgeting, as their grins widened.

“Go on,” Becky prodded.

“Then she started pulling down the pan—”

“Hold up, Blondie,” Felicity interrupted. “Tell them about the song. And why you had to sing it.”

I paused momentarily to gather myself. “Since I would soon be in my birthday suit... I had to sing ‘Happy Birthday’ to her while she pulled down the panties.” Everyone giggled and looked over at the beaming Felicity. They seemed appreciative of her creativity, and Felicity had a proud look on her face. “That’s when you came in,” I finished weakly.

“Excellent!” said Becky. “See, that wasn’t so bad now, was it?”

Actually, it was excruciating.

“Now, I want to hear about how you lost your little pubies. And look at us while you tell us.”

Of course. I knew that was coming. I looked up at the row of amused, expectant faces and took another deep breath. “First she used scissors... please, don’t make me tell this.”

“Oh, pray tell, Smoothie, pray tell!” Brenda laughed. “You’re turning into quite the storyteller!”

I closed my eyes briefly and pressed on. “F-first she used scissors. And I had to sing. When most of it was cut off, we went into the bathroom—”

“Wait, wait, wait!” Becky interrupted, leaning forward eagerly. “Back up. You had to sing? Was it ‘Happy Birthday’ again?”

“No, she made up a different song. Please...”

“Oh, you have to sing it for us, Blondie.” Becky held up her hands and turned to the group. “Who wants to hear the song Blondie sang while the hairs on his little wee-wee were coming off?” Of course, the response was a gleeful chorus of affirmatives.

“Sing it for us, sweetheart.”

I hesitated, then my trembling voice broke the silence: ♬ “My little pee-pee has no hair. Ee-eye-ee-eye-oh.” ♬

They were already losing it.

♬ “With a snip-snip here, and a snip-snip there. Here a snip, there a snip, everywhere a snip-snip... my little pee-pee has no hair. Ee-eye-ee-eye-oh.” ♬

The room shook with laughter. Mitch was stomping his feet, clutching his sides.

“Tell them about the snips, Blondie,” Felicity prompted.

“When... whenever I sang the word ‘snip’..." I took a deep, shaky breath. "She snipped off some of my hair down there with the scissors.” Another wave of wild laughter followed.

“Ingenious, Felicity,” Becky said with admiration. “Positively ingenious.”

“Thank you,” Felicity replied, now quite full of herself.

“I have a question,” Brenda cut in. All eyes turned toward Brenda as it quieted down. She paused dramatically while everyone leaned in, waiting expectantly. “Is it true,” she asked, “that if a guy spends time in a cold pool... it shrivels up?”

Naturally, every pair of eyes immediately shifted to my penis. My self-consciousness, already through the roof, somehow managed to soar even higher. I instinctively tried to close my knees, but with the way my legs were positioned on the chair, I couldn’t move them. “Well, Blondie?” continued the unrelenting Brenda. “Is it true?” The gazes rose to my blushing face.

“I-I don’t know,” was my response, while staring at several pairs of feet on the floor in front of the couch. “I don’t think so,” I stated, hoping to shut down this conversation before it advanced any further. But that hope was crushed instantly.

“Oh, it’s true,” Mitch chimed in casually.

Felicity was ready with her next jab. She gestured to my lap with mock surprise. “Well, then it must be freezing in here already. Because it can’t get any smaller than that, can it?" Once again, the redoubtable Felicity had elicited laughter from the entertained group. My cheeks turned scarlet.

“Well, we could put it to the test,” Becky said, grinning devilishly. She sprang from the couch and grabbed my hands, yanking me off the stool. “Come on, sweetie pie. Let’s take you for a little dip.”

The whole group sprung from their seats enthusiastically—ready to turn Becky's wicked idea into reality.

Becky knelt to slip the high heels off my feet and tossed them aside. Taking my hand, she led me down the hall. “Let’s go in the bathroom and clean off your face. We wouldn’t want your makeup to dirty up the pool.”

“Becky, please,” I begged, panic setting in. “The pool’s not even heated.”

“Exactly,” responded my unmerciful sister with a twinkle in her eye. She ushered me toward the bathroom. As she did, she called out, “You all might want to grab a sweater or something. There’s a bit of a chill in the air tonight.”

“Good idea, Beck,” answered Joanna while she and the rest scampered for their wraps. “It's getting nippy out there, and the wind really adds a bite to it.”

The absurdity of my situation wasn’t lost on me—while everyone was bundling up, I was about to go out there without a stitch on, and then jump into a frigid swimming pool to boot.

Becky finished her task in short order and led me into the hallway. “Wait here, sweetie, while I go get my sweater.”

I stood in the hallway, momentarily alone, and shivered in anticipation. Suddenly: SLAP! Then I felt a slight stinging sensation on my backside. Julie giggled, having just delivered the playful swat. “Let’s go, cute cheeks,” she teased, her arm sliding around my bare waist. Then, glancing down, she added with a smirk, “Time to see if your little weenie can get even weenier.”


The “Before” Measurement

While giggling at her derisive remark, Julie led me to the large pantry, where a festive, eager group stood near the back door. They were properly attired for the chilly night air. I most certainly was not.

Someone opened the back door when Becky interrupted. “Hold it!” she barked. She held a roll of measuring tape above her head. A few inches of the tape dangled from the roll. “We need to get an official ‘before’ and ‘after’ measurement,” she said with a wicked smile. Everyone leered at me. “Who wants to measure Blondie’s little winkie?” she asked. Several hands shot up amid excited giggles. “Well,” Becky laughed, “you can’t all do it. Let’s let the birthday girl do the honors.”

The delighted Felicity sprang forward. “Oh, goodie!” she yelled while snatching the tape from Becky. I groaned as she knelt on the linoleum in front of me, tape measure in hand. She looked up at me and smiled. “Isn’t this fun, Blondie?” she teased, brushing her hair out of the way. I remained silent, unable to believe what was transpiring.

Felicity looked down at her objective. “Becky,” she requested, “Would you mind holding his little thingy up while I measure it?”

“Sure,” laughed Becky. She placed two fingers underneath my penis and held it up. The humiliation of my sister handling my penis under the extremely embarrassing circumstances was torturous.

Felicity stretched the tape across the length of my shaft. To obtain a reading, she lowered her head until I felt her hair brush against my bare stomach. She squinted at the numbers. “It looks like two and one-eighth inches,” she announced gleefully, eliciting giggles and guffaws from the entertained group.

“If this pool thing really is true, then we’ll need a magnifying glass to see how long—I mean how tiny it is,” Cheryl quipped.


The Pool

The pool lights were on, and the entire area was well lit. The chilly air—I’d guess the temperature was in the mid-forties, with a steady breeze—sent shivers through me and instantly raised goose bumps across my exposed skin. I folded my arms across my chest in a futile attempt to stay warm.

“Brrrr,” Joanna shivered. “It really is chilly out here.” She looked at me and said, “You must be freezing, Blondie.” She looked down at my penis, which may have dwindled in size already. I could tell that my scrotum had tightened and contracted.

“You may not even need to go in the pool, little boy," Becky taunted. "I think it’s already shrinking.”

The comment generated another chorus of laughter, and I self-consciously lowered my hands and covered my shriveling package as we approached the pool.

“Let’s see,” Becky mused. “What’s the best way to do this?” She snapped her fingers. “I know—you should go down the slide, Blondie. I know how much you love the slide.”

Groaning inwardly, I trudged toward the ladder. I’d climbed it hundreds of times before—but never like this. Never naked. Never with an audience ridiculing me through every step. As I began the slow, shameful ascent, the laughter behind me grew louder—partly mocking their naked victim, partly eager for what would come next.

At the top, I perched nervously, my legs trembling as I looked down. Thirty feet below, they were already chanting.

“Go Blondie! Go Blondie! Go Blondie!”

With no other choice, I gave myself a silent countdown and pushed off. No reason to delay the inevitable. I slid down to the accompaniment of cheers, clapping and laughter. I braced myself for the shock.

I had seriously underestimated its extent. Sure, anyone who’s jumped into a cold pool knows there is an initial jolt—but this was on a whole different level. It felt like a charge of electricity had surged throughout my body. When I surfaced, I was still overcome from the shock to my system.

“Ah! Ah! Oh shit! Shit! Oh God! It's freezing!” I screamed.

My tormentors were laughing and cheering. I swam toward the side of the pool, intent on escaping the biting cold.

“Uh, uh, uh!” Becky admonished as she used her foot to obstruct my effort to climb out of the pool. “You need to spend a few minutes in there, little brother, to get the full effect, if you know what I mean.” She paused and giggled to herself. “Now go out to the middle until we tell you to come out.”

I obeyed, and treaded water for what seemed an interminable amount of time, teeth chattering all the while.

“I think it’s getting smaller,” observed the squinting Marcia after a couple of minutes.

“I’ll say,” Julie chimed in as she bent from the waist and peered in my direction. “I can barely see it!” she exclaimed, eliciting more hearty laughter.

I reached down and surreptitiously checked myself out. Much to my dismay, there indeed had been a change. The cold water had done a number—there was nothing there but a tiny, shrunken nub! “Oh, God,” I said to myself in a semi panic. I turned my back to the group and pulled on it, desperately trying to coax some length back out of the depths. But the forces were against me, and in mere moments my humiliation would escalate.

“Okay, Blondie,” called Becky, right on cue. “Come on out. Let’s have a look.”

I swam toward the edge of the pool, where eight pairs of eyes were fixed on me, each face a mix of amusement and eager anticipation. Just before climbing out, I reached down in a final, futile attempt to restore what the cold had claimed. I pulled on my shrunken penis, almost pleadingly, in one last desperate effort to somehow resurrect it to its regular size. I don’t think it helped.

“Oh my God, check it out!” Brenda shrieked when I climbed out of the pool, causing me to instinctively cover myself with my hands. Immediately I heard three loud slapping sounds, which was followed by a sharp stinging on my wet backside.

“Put your hands on your head and keep them there!” Becky ordered.

Blushing furiously, I complied. And just like that, the floodgates opened—the teasing came fast and mercilessly.

Becky: “Oh my gosh... it really did shrink!”

Marcia: “Did it just... disappear? I swear it was there before!”

Julie: “Okay, that’s seriously the tiniest one I’ve ever seen.”

Cheryl: “I can barely see anything!”

Joanna: “Oh, this is too much!”

And, of course, Felicity: “Blondie, sweetie... you're officially smaller than Joey now.”


(Not) Measuring Up

“Come on,” Becky said, grabbing my hand. “Let’s go in the poolroom. We must get a measurement."

Of course, everyone eagerly followed. It was warmer there, but I was still dripping and shivering and mortified beyond belief.

For the first time, I looked down. I’ll never forget the sight and the feeling of disbelief I experienced at that moment. I could barely see the head of my penis peeking out from my midsection, and my ball sack had shriveled up to almost nothing. And of course, I was completely devoid of hair. I swear, it looked like I had the genitals of a two-year-old!

The grinning Felicity approached me with the measuring tape. “I don’t need you to hold anything this time, Becky,” she laughed. “There’s nothing left to hold.”

Indeed, she was right. My little penis was sticking straight out, it’s lack of size and weight keeping it from drooping down. Felicity bent over and once again stretched the tape across my now almost-absent penis. She came up beaming.

“One and three-quarters!” she announced gleefully, much to everyone’s utter delight and amazement.

“Aww, such a cute wittle baby boy,” Becky cooed, giving the underside of my chin a playful tickle with her fingers.

“Does wittle Bwondie need a diaper?” mocked Julie.

The hilarity was now at its highest point of the evening, as was my mortification. I stood there helpless—hands on my head, shivering, and soaking in the full weight of my humiliation.

Cheryl lowered a camera to the object of everyone’s amusement and snapped a couple of pictures. Mitch was gleefully capturing a video. I remember thinking that with this moment caught on camera and video that I may never live this godawful experience down. That no matter how hard I try to get over this, there will always be a picture, a video, or a knowing smile. That my humiliation will never completely subside.

* * * * *

I think I’ll stop here for a while. I do have one more episode in store for you, but chronicling these latest events has left me spent. I’ll try to muster up the nerve to relate to you the last shameful experience I had at the hands of the loathsome terrors from Roosevelt High.
Last edited by Blondie on Sun Apr 05, 2026 10:36 pm, edited 4 times in total.
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Roosevelt Humiliations, Chapter 26

Post by Blondie »

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Chapter 26: Forced Orgasm

The Lopsided Contest

Well, I’ve finally mustered up the courage to tell you about the rest of the degradations I suffered at the slumber party at the hands of the ruthless evildoers from Roosevelt High. What follows will be difficult to recount, as the level of humiliation reached heights I never thought possible. I doubt I’ll ever fully recover.

When I left off, we were in the poolroom and they had just finished measuring my penis, which had shrunken considerably after I was forced to tread water in our cold swimming pool. Spirits were high, drinks had been flowing, and the gang was in full-on party mode—giddy, loud, and, as you’re about to see, emboldened.

The poolroom was fairly spacious and nicely furnished. Besides the furniture, there was a full-sized pool table, a stereo system, and even a bar. Loud music and general merriment filled the room—except for one dissenter. That would be the naked sixteen-year-old boy, whose state of humiliation was already extreme, and who could sense that things were about to escalate.

“How about a game of 8-ball?” suggested Julie, casually picking up a cue stick.

“I wanna play!” chimed in Felicity, grabbing one for herself.

Julie smirked. “I’ve got an idea—let’s play girls versus boys. Felicity and I against Blondie and Mitch.” Everyone seemed quite pleased with the idea. Everyone, that is, except me. I groaned inwardly. Once again, I would be taking an active part in my humiliation.

“What are the stakes?” asked Brenda with a devilish glint in her eye. For a moment, there was silence while their mischievous minds worked actively.

“I know!" Julie’s eyes lit up. All heads turned toward her—most with anticipation, mine with dread. “The two that lose have to give each other a big wet kiss on the lips.” The room exploded with gasps and laughter. “And I don’t mean a little peck,” Julie added over the noise. “I mean serious tongue action, thirty seconds minimum.”

Once again there was a boisterous response. I glanced furtively at Mitch, who to my disgust was staring at me, grinning lecherously. “All right then, let the games begin,” he said. To my chagrin he gave my bare ass a friendly pat as he stepped toward the cue sticks. He returned with two sticks and handed me one of them, grinning freely.

“You break, Blondie,” Julie announced, racking the balls with a grin.

I stepped up to the table and closed my eyes tightly, pressing my fist to my forehead, trying to psych myself up. Under normal circumstances, I would regard myself as a halfway decent pool player. But let’s face it—naked, humiliated, and staring down the prospect of a forced lip-lock with Mitch, I was far from my comfort zone. Still, I knew I had to try. I certainly would much rather see the two sisters in a lip lock than have to face the same fate with Mitch.

I shuddered at the thought of the latter scenario and leaned over the cue ball in preparation to break. I heard the giggling and blushed ever so brightly in self-consciousness. Through it all, I managed to break the rack decisively, the balls spreading impressively across the table. I heard a ball drop in a side pocket. Felicity leaned over and peeked into the pocket, in such a way that I couldn’t help but be reminded of a similar motion she made earlier that night when she leaned over and peeked into the panties I was wearing.

God, that seems like ages ago.

“Solids,” she announced, waving the two-ball in the air before placing it back. I scanned the table—there were at least three decent shots available. The seven-ball in the corner pocket looked like the easiest, and the one that could easily set me up for my next two shots. I leaned over again, and just as I was going into my forward motion with the shot, Julie reached between my legs from behind and tickled my balls with her fingers.

“Aagh!” I yelped while lifting my upper body straight up. I had barely contacted the cue ball, moving it only a couple of inches. Everyone laughed heartily while I blushed crimson again.

Julie proceeded to surprise everyone by exhibiting her prowess as a pool shark. “Eleven, corner,” she called out before expertly knocking it in. She coolly chalked her cue stick while appraising her next shot. “Nine, side pocket, back this way,” she called. I looked on dejectedly as she banked in the nine-ball effortlessly. It became obvious why she was willing to commit to the stakes. “Fourteen, corner.” Boom, slam-dunk. “Twelve, other corner.” No problem. “Ten, side pocket.” Done. She chalked again. “Fifteen, corner.” Bam, she slammed it home. Only the thirteen, then the eight were left. But the thirteen was blocked by a couple of solid balls, so she really had no shot. She missed, leaving me with a faint glimmer of hope.

“Sorry, little sis,” she said to Felicity.

“No problem, you were amazing,” Felicity replied with a kiss on her sister’s cheek. “That’s the only kissing we’ll be doing tonight,” she added, flashing me a grin. The crowd roared again.

The smiling Mitch lined up his shot. The four-ball was leaning against the near corner, seemingly begging to get knocked in. But he chose a much more difficult shot. I should have known that I wouldn’t get any cooperation from him. “Seven, one bank, all the way back,” he called. And, of course, he didn’t come close. Not only that, but he also left a very simple shot at the thirteen-ball for Felicity, and the eight-ball was ominously close to the other corner pocket.

“Oh, this is just too easy,” said Felicity, grinning gleefully. “Thirteen, on my thirteenth birthday, in the corner.” She wasn’t as skilled as her sister, but she didn’t have to be. A novice could have made that shot, and she did so, easily. Felicity and the eight-ball were all that stood in the way of my destiny with Mitch. I lowered my head miserably, as the shot was even easier than her last one.

“Eight-ball, corner pocket.” She sang the words melodically.

The room was quiet in anticipation, and Felicity, with her now-recognized flair for drama, let the moment draw out. She calmly chalked her cue stick, then blew the excess chalk away in my direction with a light blow on the tip. She looked up at me, then at Mitch, and grinned broadly. She then broke the silence with an age-old schoolyard chant: “Mitch and Blondie, sitting in a tree,” she sung. “K-I-S-S-I-N-G.” She slowly circled the table, eyeing the shot from all angles. It was simply for effect, since it was obvious what she was going to do. “First comes love...then comes marriage... then comes Blondie in a baby carriage!”

While everyone laughed, she leaned over the shot, staring down the barrel of her cue stick. Then, to everyone’s approval (save mine, of course), she authoritatively slammed her stick into the cue ball and watched with satisfaction as the eight-ball thumped against the back of the pocket and dropped from sight.

The room erupted. Applause, laughter, whooping cheers. I stood in stunned silence, my eyes locked on the table—seven solid balls still sitting there, a clear indication of how I was bamboozled. Of course, the way the evening had gone, I should not have expected any other outcome.

“Come on, you two, pay off your bet,” prompted Felicity impatiently. “Winners eat dinners, losers are smoochers.” The silliness brought more laughter from the drunken group. Obviously at this point it didn’t take much to amuse the revelers.


The Kiss

Mitch was already stepping toward me, much too eagerly for my liking.

“Hang on a sec!” said Becky. She hurried over to the stereo and flipped through the CD collection. “Ah, here we go. The Final Jeopardy theme. This is perfect—it’s exactly thirty seconds long.” I groaned, bemoaning the day I whimsically purchased a CD comprised of several television theme songs.

“You’d better cooperate, Blondie,” warned Brenda, “if you know what’s good for you. Thirty seconds, and act like you mean it. Ready, go!”

The music began. ♬ Duh-duh, duh-duh, duh-duh-duh... ♬

“It’s just you and me, Blondie boy,” Mitch said, stepping in close and pressing his lips to mine.

“Ew, gross!” shrieked Felicity—but she didn't mean it.

Suffice it to say, the next thirty seconds were among the most unpleasant I’ve ever experienced. Right from the get-go Mitch’s enthusiasm was unfettered. To my disgust, his tongue met mine and darted around the confines of my mouth with reckless abandon. I was most repulsed when he placed his hands on my ass and started rhythmically grinding his midsection against mine. I felt the unmistakable evidence of his pleasure pressing against my lower abdomen. The girls were howling with laughter—hooting, gasping, egging him on. I squeezed my eyes shut, face burning, and endured. It felt like the music would never end.

At long last, the final note played. I recoiled instantly. The girls were cheering raucously. I opened my eyes and was met by Mitch’s flushing, grinning face. His hands were still clutching my ass, and I managed to squirm free—but not before suffering through one last pelvic thrust from the impassioned aggressor.

“Oh Blondie, you’re such a tease,” taunted Mitch. As I backed away, I couldn’t avoid noticing the engorged protrusion in Mitch’s khakis, which only added to my revulsion. The girls seemed to follow my gaze, and then, seemingly in concert with each other, turned their gazes to my penis, which had remained in its small, flaccid state. More giggling ensued.


The Dildo

“I’ve got an idea!” Becky suddenly shrieked, her eyes lighting up with mischief. Without another word, she darted out of the poolroom and took off running around the long, winding path that circled the swimming pool. “I’ll be right back!” she called over her shoulder as she disappeared into the house. Everyone turned to watch her go, curiosity and anticipation thick in the air. Whatever devious scheme my sister had just cooked up, we all knew it wasn’t going to be good for me. I bowed my head, already bracing myself for whatever fresh humiliation was headed my way.

It didn’t take long. The door swung open just minutes later, and Becky re-entered the poolroom, slightly winded but grinning devilishly. In her right hand, she clutched a mystery object wrapped tightly in a small pink hand towel. Without a word, she strode over to the pool table and laid the bundle down. The item remained hidden in the towel, but her impish grin spoke volumes.

Rather than reveal it right away, she turned her attention to me. “You’ve been putting on such a nice little show for us tonight, sweetie,” she said. “It’d be a real shame to let the fun end now—you’re on such a roll.” With maddening slowness, she began to unroll the towel on the table. She continued speaking to me as she did so, knowing just how to draw out the suspense for her expectant cohorts. “You’ve already shown us how much you care about Mitch,” she teased, “and we can see that you know how to kiss.” The towel was nearly open now. “But do you know how to suck? That’s the question.”

Her sordid plan gradually hit home, as a cream-colored dildo emerged from the confines of the towel. It was approximately seven inches long and of moderate thickness. It resembled a real penis disturbingly well. She held it high in the air for the benefit of her thrilled audience.

“Oh, Becky, you little devil, you!” roared her best friend Brenda. The ebullient response from everyone filled the room, bolstering Becky’s enthusiasm. She held the dildo up to my face and laid out her very unpleasant instructions.

“Let’s play a little pretend game, dear Blondie. Here, take this.” I reluctantly took the loathsome object in my hands, looking at it like it was a lethal snake. “Now I’d like you to pretend that it's your partner Mitch.” Guffaws rang through the room. I glanced cautiously at Mitch and was chagrined to see him grinning lewdly at me. My eyes shot back at his “pretend” penis. I was in the throes of wretchedness.

Becky continued. “Pretend you’re horny, Blondie, and you just love licking and sucking Mitch’s big dick. You want to bring him to an orgasm, but you want to draw it out, because you love it so much.” The laughter and my mortification increased. “So start out nice and slowly, then build up the momentum and bring him to a raging climax.” She stopped, which was my cue to begin the degrading act. But I couldn’t quite compel myself to do her bidding, so she coerced me by taking my hand and lifting the dildo to my mouth. “Come on, sweetie, Mitch is waiting. Stick out your tongue and start licking it.”

I took a deep breath and started licking the dildo, much to the delight of my cheering, laughing tormentors. “That’s it, sweetheart,” prompted Becky, “Lick it all the way up and down. And kiss it, Princess. Give it some nice tender kisses. Mitch will love it.” With extreme reluctance I followed Becky’s directions, alternately licking and kissing the dreaded dildo while my audience cheered me on.

Brenda was the culprit who advanced my present state of mortification. “Blondie, you’re not getting very excited, are you? Look at this little thing,” she said while taking my penis in her thumb and first two fingers. The surprise intrusion caused me to retract my hips and let out a high-pitched yelp, much to everyone's hilarity.

I had lowered the dildo from my mouth, which would be corrected forthwith. “Did I tell you to stop, Blondie?” asked the giggling Brenda. “Keep licking, Mitch is getting very hot.” I went back to licking the dildo under everyone's watchful eyes.

“Put it in your pretty little mouth and start sucking on the head, Blondie,” instructed Becky. I did. “That’s it, suck on it. Now lick it some more. Good, now suck. Oh yes, you’ve got the hang of it, Princess. Lick and suck, lick and suck. You're really good at giving head. Oh, Mitch is loving it.” The laughter was relentless as I carried out the shameful charade.

Then, just when I foolishly believed my humiliation had peaked, the wickedly imaginative Felicity managed to take it to another level. “I wonder how big Blondie’s little pee-pee gets when he gets excited?” she mused. Leave it to the young fiend from hell to open a new can of worms.

“Well,” responded Brenda, “The average is about five and a half inches, I read somewhere. I seriously doubt that our little friend here can approach that.”

“Um,” said Felicity with her hand on her chin as if in deep thought. “Maybe we should find out,” she said with a twinkle in her eye. An energetic reaction resulted when everyone grasped what Felicity was suggesting.

“Oh yes,” agreed Brenda, “We really need to find out. I’ll bet it’s not much more than five inches—if that.”

“Okay, here’s the deal,” said the keyed-up Felicity effusively. Her fertile mind seemed to always be working, and it never failed to work to my detriment. “If Blondie’s little penis in his excited state is five inches or more, then he wins, and we’ll let him get dressed and go on his... not so merry way. But... if it’s less than five inches he... let me think about this for a second... I’ve got it! If it’s less than five inches he has to perform for us by playing with his little toy until he spurts.” Explosive cheers of amusement and agreement followed.

“Please, no...” I pleaded, lowering the dildo from my mouth.

“Lick and suck, lick and suck!” reminded Becky. I obeyed her unrelenting order. She then picked up the pink hand towel and wrapped it around my eyes while tying it behind my head, creating an effective blindfold. I momentarily stopped activity with the dildo, which brought on another admonition from Becky. “I’m not going to tell you again, Blondie—you keep sucking on Mitch’s love muscle until he comes.” Everyone laughed and I flushed brighter.

There was a minute of two of total silence, save for the small slurping sounds I was making with the dildo. I thought I might have heard some whispering.

Then it started.


Sexual Arousal

I felt some fingers caressing my hair and lightly massaging my scalp. I had no idea who it was. Within moments two other sets of fingers began stroking my nipples and another began caressing my sides and tummy. It was stimulating, and it was all I could do to keep from becoming erect. I was really hoping I could fight it off and avoid further humiliation.

But then I felt someone else—though to this day I can’t say who was doing what—slide up behind me, licking my right ear and probing my ear canal with their tongue. At the same time, two more hands began stroking the insides of both my thighs. Then another tongue started exploring my other ear. The sensation was exquisite, and much to my chagrin, I felt myself growing aroused. I caught the sound of a couple of stifled giggles, followed by a whispered “shh.” I remember thinking what a sight I must have been, dutifully sucking on a dildo (Mitch’s “pretend” penis) while trying unsuccessfully to stave off the inevitable hard-on. To make matters worse, I was pretty sure someone was filming a video of the extraordinary scene.

My situation was growing bleaker by the second. I felt a tongue tracing slow circles around my nipples before gradually working its way down my torso. Meanwhile, someone—please, not Mitch!—was gently caressing my balls with their fingers. There was no turning back now—I had a full-fledged hard-on. Once again, I heard stifled giggles nearby.

The tongue had found its way to my genitals and began licking my balls. I felt my penis standing straight up. The tongue (God, please don’t be Mitch!) slowly, teasingly slid up and down the shaft of my penis. Whoever it was, she (I'm sticking with "she") knew what she was doing. When the tip of her tongue expertly explored my frenulum I involuntarily began rotating my hips and moaning softly, while still sucking on the dildo. I heard more giggling. Then I felt a mouth (I tried to imagine it belonging to Cheryl) engulfing my whole penis. For the first time in my life, I was getting a blow job. Never did I imaging that my first experience receiving oral sex would be tremendously humiliating, but that was exactly my sorry situation.

Then a voice—I recognized as Becky’s—whispered loudly in my ear, even as someone else continued licking it. “Suck faster, Blondie. Mitch wants to cum. Faster! Faster!” To the sounds of more muffled giggles, I attacked the dildo with more fervor. The slurping sounds were louder, coinciding with the slurping sounds coming from my own penis. Both my head and hips were moving back and forth at a furious pace. Two tongues still explored my ears, another mouth was caressing my chest and stomach, and someone—maybe the same person who was giving me head—maybe not—was teasing my balls with their fingers. The sensation was overwhelming, and I was on the verge of exploding. My sister somehow sensed as much.

“STOP!” yelled Becky.

And they did. So did I, pulling the dildo from my mouth and holding it at my side. I was left on the edge of climax, caught in a strange contradiction. Physically, it was pure frustration—but psychologically and emotionally, giving in to orgasm at their hands (and mouths) would have only deepened my humiliation.


Another Measurement

“Time for a measurement!” Felicity declared, grabbing the measuring tape from the top of the bar.

“Yes!” Cheryl chimed in. “Let’s see if Blondie has to finish the job right here—or if he can save it for the privacy of his bedroom.” That set off another round of giggles.

Everyone gathered around me in excited anticipation, while I prayed silently that I would “measure up.” I honestly wasn’t sure if I would or not. It had been a few months since I had last measured myself—then, I was only four and a half inches. I remember thinking that surely I must be larger now. My penis was still fully erect, so at least I had a chance, I felt.

Felicity eagerly stretched the tape along the length of my shaft. I glanced down at the “tale of the tape,” and my heart sank. “It’s only four and a half inches!” squealed Felicity, to everyone’s glee.

“You lose, Blondie,” Becky sang cheerily. “Now we get to see your grand performance. Do you think you can spurt some juice out of that little thing?” The room erupted in laughter. Their excitement was through the roof. Felicity rubbed her palms together and bounced up and down, grinning from ear to ear.


My Naked Performance

“Let’s see,” Becky said. “You’re going to need a stage for this performance.” She grabbed a large beach towel from a shelf and spread it over the felt of the pool table. Patting the surface, she added, “Hop up here, sweetie pie, so we can all get a better look.” I briefly buried my face in my hands before lifting a knee to climb onto the table. I tried to hand Becky the dildo, but she wasn’t having it. “No-no-no, you need that. You've got poor Mitch all worked up, and he really needs you to make him cum.” Dismally, I climbed up onto the pool table.

“Blondie promised he’d dance for me on my birthday,” Felicity declared. “I think we should make Blondie dance for us while he makes himself spurt.” I winced, and Becky let out a delighted laugh.

“Oh, what a brilliant idea! A naked dance on the pool table while sucking on Mitch and getting himself off—now that will be a spectacle!” She spun toward the stereo, rifling through CDs. “Marcia, make sure you get this on video. It’ll be priceless footage.” She popped in a CD. “Alright, big boy, it’s showtime. This is your grand finale, so you’d better make it good.” She hit the play button and I’m So Excited by the Pointer Sisters began playing on the stereo. Becky jacked up the volume. I started dancing, albeit slowly and half-heartedly. My dignity had long since vanished, but this... this was a new low.

“Faster, Blondie! Come on, shake it!” Julie shouted over the music. I tried to pick up the pace, though it was painfully clear my heart wasn’t in it. The room was echoing with laughter and hoots of delight.

“Come on, Blondie, move it! Show us what you’ve got!” Becky jeered.

“Suck Mitch’s cock, Blondie, suck it!” yelled Brenda. I had forgotten about the dildo in my left hand. I raised it to my mouth and again simulated oral sex on the fake penis. “Suck faster, Blondie!” continued the relentless Brenda. “Mitch is ready to explode! Suck that dick!” I increased the tempo of the sucking, much to everyone’s continued entertainment.

“Spank that little monkey, Blondie!” ordered Becky.

My penis had shrunk to about half its size since the group stimulation ended just minutes before. I knew it would be tough to get that excited again under the circumstances, but I had the grim feeling this wouldn’t end until I managed to climax. I took my penis in my right hand and started playing with myself.

Becky reached behind her, grabbed a small brown bottle of suntan oil from the shelf, and sauntered over to the pool table. “Hold out your right hand!” she yelled over the music. When I obeyed, she tipped the bottle and squeezed a generous puddle into my palm. The sweet scent of coconut spread through the room. “Stroke that little weenie, Blondie!" commanded my sister. I did so, and my penis became harder, with the help of the lubricant. “Keep dancing, Blondie! And suck that dick! Go Blondie! Go Blondie!” I stroked, I danced, and I sucked. The cheering and laughing swelled. “You’re not dancing fast enough, Blondie—faster!” Becky screamed.

“Dance, Blondie! Faster!” Julie echoed. I forced my hips to move just a little quicker, but my heart wasn’t in it—words can’t do justice to the humiliation I felt that moment. While seven gleeful young women were cheering me on, completely lost in the hilarity, Mitch stood behind the bar, which was conveniently shielding his activity. It was obvious he was pleasuring himself. He looked at me lustfully, and I quickly turned my head away in disgust.

Then Becky’s tone shifted. Evidently I wasn't dancing fast enough for her. “All right, that does it,” she said, marching to the wall and pulling a canoe oar off its hook. My eyes went wide. It didn’t take a brain surgeon to comprehend its purpose for this situation. I braced myself for the blow, but no amount of mental preparation on my part could have mitigated the pain I was about to experience.

“I said FASTER!” The loud smacking sound of wood meeting flesh and the word “faster” were simultaneous. I yelped, the pain flashing through me like a bolt of lightning. Becky looked up at me and held the oar up menacingly. “Do I need to tell you again?” she yelled.

I needed no further encouragement. I started dancing like a maniac—hell, I was practically jumping up and down from the pain. I moved at a frenetic pace, and the rhythm of the sucking and stroking motions naturally increased likewise. The group was now laughing hysterically, caught up in a wild frenzy.

I couldn’t help but glance at Mitch and could see he was picking up speed, his activity growing more urgent. I couldn’t let that get to me—I had to cum, so I could end my misery. I was getting very close, and I was pumping away frantically.

Becky turned the volume up full blast. The Pointers were at a fever pitch, as was the cheering and laughter.

I'm so excited! I just can't hide it! I'm about to lose control, and I think I like it—yeah!

And it was right at that point that I lost control, but I don’t think I liked it. I stopped dancing, and my body stiffened. Without thinking, I dropped my left hand but left the dildo in my mouth—to their added hilarity, I’m sure. I pumped furiously with my right hand, and the juices flowed.

“WOO-HOO!” they shrieked, some stomping and clapping. I continued to pump away, at that point completely absorbed in my fulfillment.

“YEAH, BABY! YOU GO, BLONDIE! WOOOOO!”

By the time the song hit its final note, the last drops of my fluid dribbled out, and I dropped to my hands and knees, utterly spent from my orgasm and the hideous humiliation I had endured. Beads of sweat dripped from my forehead. My arms were shaking. The music had quieted, and momentarily the girls had, too.

Then a moan slipped out from behind the bar. The girls turned back, and it was clear what had just happened. “Congratulations, Blondie, you did it—you got Mitch off!” my sister blurted, setting off another wave of laughter.

Becky tossed me a robe, and as the cheerful group filed out, she delivered one last parting shot. “Oh—don’t make any plans for tomorrow night, sweetie. We’ll all be back to watch the video, and we’ll need someone to serve cocktails and hors d’ oeuvres." She grinned mischievously. “Nothing fancy—you can come as you are.”

Their laughter faded into the night. I wrapped the robe around my shoulders and stared down blankly at my drying semen. The sense of desolation was overwhelming, and the tears I’d been holding back began to flow. My quiet whimpers quickly turned into loud, uncontrollable sobs. The hopelessness hit me full force, and I couldn't stop it.

I rued the day I enrolled in Roosevelt High—the very ground where my humiliations began.


Epilogue

Two weeks later, I was finally starting to come out of my doldrums. And yes, I had to submit to them again the following night. I won’t go into details, but they had their way with me once more. They made me strip naked and serve drinks while we watched the video. They laughed and reveled in my torment—and for me, it was pure torture, reliving that horrible night all over again.

I don’t know what the future holds, but one thing is certain: I will not forget. I don’t yet know how I’ll do it, but I’m determined to exact revenge on every single one of my tormentors. One day, they’ll get what’s coming to them—and they’ll regret everything they did to me. And when that day comes, I’ll be sure to tell you all about it.

What a great feeling that will be!

End
Last edited by Blondie on Wed Oct 15, 2025 10:54 pm, edited 3 times in total.
Tenacious
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Re: Roosevelt Humiliations

Post by Tenacious »

I've always imagined a secret unpublished chapter of this story (as amazing as it already is), where the one of girls (maybe Marcia?) wakes Blondie up in the middle of the night and makes him come visit Mitch. In my mind she wants some extra humiliation and thinks Blondie should have to give Mitch a more personal apology for being such a tease all night.
Last edited by Tenacious on Thu May 22, 2025 6:56 am, edited 1 time in total.
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Re: Roosevelt Humiliations

Post by Blondie »

Tenacious wrote: Thu May 22, 2025 6:51 am I've always imagined a secret unpublished chapter of this story (as amazing as it already is), where the one of girls (maybe Marcia?) wakes Blondie up in the middle of the night and makes him come visit Mitch. In my mind she wants some extra humiliation and thinks Blondie should have to give Mitch a more personal apology for being such a tease all night.
Interesting idea. I was going to respond with "Well, Blondie has probably suffered enough," but of course he was subsequently put through his paces by Felicity during his senior year at Roosevelt High. No such thing as too much humiliation in these parts, I guess. :)
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