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 22

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Chapter 22: Denuded by a Thirteen-Year-Old

Naked on the Bed

Felicity grinned wickedly at me for a few seconds. I stood there on the stool, still bent over at the waist. Without a word, she lifted one of my legs, then the other, freeing the panties from my feet. I was now completely naked and at her mercy. She dropped the panties on the floor and reached out for my hand. “Come, sweetie, let’s chitchat over on the bed for a while.” My torture at the hands of this cruel little girl was going to carry on. When I took her hand she pulled me from the stool. My other hand still covered my groin as she led me to the bed. “Up we go.” She climbed onto the bed, pulling me with her. She situated us so that my back was to the door, and she was facing me. I was sitting with my legs off to my side, my hands still covering my modesty. I wondered what the hell she was up to.

“Come on, Blondie, let’s get comfortable. Spread your legs out.” She leaned forward and grabbed both of my ankles, pulling them toward her. She spread them out, placing them on either side of her hips. Then she inched closer to me, placing her legs over my thighs. Her clothed torso was now no more than a foot or so from my naked one. She held out her hands. “Give me your hands,” she requested.

Of course, it wasn’t a request. I had to submit. I hesitated, then lifted my hands into hers. She spread out my hands and rested them on the bed, outside of my knees. I was now fully exposed, which, of course, was her intent. I involuntarily tried to squeeze my thighs together but was inhibited by her hips. She looked between my legs and smiled.

"Tell me, Blondie, what's it like to be naked against your will in front of a thirteen-year-old girl?" I didn't have a ready response. "I can only imagine how humiliating this must be for you," she continued. "I think if I were in your shoes—oh, silly me, you're not wearing any shoes," she said with a giggle. "If I was in your situation I think I'd just die of humiliation." She smiled at me with a twinkle in her eye while I turned my gaze downcast and fixated it on the flowery-designed bedspread. She continued with her verbal torment. “Tell me about Mitch.” I flinched, which did not go unnoticed. She pounced on the moment. “I hear he likes both girls and boys. Is that true?” I didn't respond. "Answer me, sweetie."

“Y-yes, I think that’s true.”

“I hear he likes you, Blondie.” I didn’t reply. “Is that true? Is he hot for you, Blondie? Do you think he wants to get inside your panties?”

“Please, stop....”

“You know it's true, don't you? That’s why he’s here tonight, isn’t it, just to see you?” I couldn’t answer. She pointed to the babydoll that was draped over a chair by the bed. “Mitch will be all excited to see you in that, won’t he, Blondie?”

“Please…”

“Or maybe you can go out just like you are. Would you like to do that?”

“No!” My head shot up and Felicity smiled at my quick exclamation.

“Okay, relax, sweetheart. I won't make you go out there all naked. You can wear the babydoll. Would you like to wear the babydoll?” The evil little thing was ruthless. I nodded. “Tell me, Blondie, what do you want to wear when we go out there.”

“The babydoll.”

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

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

“Why of course you can, my darling. Mitch will be very excited to see you in your sexy babydoll.” She grinned at me, then looked down at my legs. “It’ll really show off your pretty legs.” She let go of my left hand and stroked my leg. “He’s going to love your silky, slender legs. Don’t you think so, Blondie?”

“Oh, God, please, no…”

She continued stroking my leg and ventured up to the top of my thigh. Under the humiliating circumstances, I felt no sexual pleasure at all. “How did your legs get so smooth, Blondie? Did you shave them?”

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

She lifted my right arm and stoked it up and down with her other hand. “And you have such smooth, girlie arms. Pretty, pretty," she said, emphasizing the "t” sound. I fidgeted; I was becoming increasingly more uncomfortable, and she was reveling in my shame. She lifted my arm high in the air and zeroed in on my hairless armpit. “And your underarms are nice and smooth, too.” She lowered my arm and looked me right in the eye. “Tell me how you got so pretty, Blondie.”

“B-Becky and Brenda did it to me.”

“Oh, and a wonderful job they did!” She looked at my pubic hair, then reached down and gently tugged on a few strands, causing me to flinch. “Why did they leave your hair down here?” I didn’t answer. “Shall we get rid of it now?”

“NO!” I cried, my eyes widening in horror.

That was probably a critical mistake; I could tell by the smile on her face that she knew she had touched a nerve. She left it alone for the moment, but I had a haunting feeling it was something she would revisit. Again she looked at my exposed genitals. “Don’t you think you’re a little small down there for a sixteen-year-old?” I fidgeted some more, much to her delight. She knew which buttons to push. “I told you about Joey, my ten-year-old brother. I saw his little thing the other day, and yours is as small as his.” That was at least the third time she had reminded me of that unpleasant piece of information. “Aren’t you embarrassed when you have to shower after gym class? I’ll bet all the other boys make jokes about your little pee pee. Oh, you’re really blushing now, Blondie, it must be true.” I just sat there, unable to speak, my face feeling like it was on fire. “Talk to me, Blondie; I’m monopolizing the conversation again.” She took my hands again. She squeezed them and bounced them off the bed, pushing for an answer.

“I-I don’t know if they joke.”

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

“No…please.” I was looking off to my right, staring at the floor, unable to make eye contact with the little devil.

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

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

“Tell me the story about the auditorium.”

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

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

“Th-they made me take my clothes off. That’s it.”

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

I nodded gloomily. “But it was dark,” I said.

“I heard something about a flashlight. Didn’t Marcia make you shine the flashlight on your little pee pee?”

“Yes.” I was speaking softly and staring at the floor.

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

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

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

“I don’t remember,” I lied (it was true).

She pointed between my legs. “Shall we remove that unsightly hair before we go out there, sweetie?” My startled reaction played right into her hands. “Ah, I think we’ve struck a nerve, haven’t we, Blondie? Well, you know, I don’t have any hair on my privates, so it’s only fair that you don’t, either.” She paused, eyeing me for a reaction. There was none; I was still stunned by the latest turn in the conversation. “Doesn’t that surprise you, Blondie? After all, I’m thirteen now. Most girls have reached puberty before that. Not I. Physically, I have the body of an eleven-year-old. I'm probably emotionally immature, too, if I'm being honest. But I’ve been told that intellectually I’m as smart as a lot of college students.” I was in no mood to listen to her self-assessment. And the fact that she had the body of an eleven-year-old somehow only made my abject submission to her that much more humiliating. Which, now that I think about it, is probably the reason she was telling me. Like I said before, she was perceptive well beyond her years.

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

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

“Let’s see now, refresh my memory, sweetie. What was it you called me earlier?” At that moment I knew there would be no mercy. I lowered my head in gloom. “Something about a female dog…tell me, what exactly was it you called me?”

“A fucking bitch,” I replied softly.

“Yes, that was it. You really shouldn’t have said that, Blondie. Here I’ve been so nice to you, dressing you up and helping you find your feminine side, and this is the gratitude I get.” She shook her head for effect, as if she was really disappointed with me. Then she got up on her knees and pulled me from the bed.


♬Pretty Blondie Lost His Hair♬

“Now be a real sweetie and help me find a pair of scissors.” She started rummaging through the nightstand drawer. I stood there, stunned at what was about to take place. “Well don’t just stand there. Check the dresser.”

I slowly walked over to the dresser, unbelieving of what was transpiring. Here I was, naked, helping my tormentor find scissors so she could cut off my pubic hair. I went through the motions, opening the top drawer. As luck (or lack of it) would have it, the first thing I saw was a small pair of scissors. Desperately, I picked them up, hoping to hide them under the bed.

“Good boy, Blondie!” shrieked Felicity, sneaking up on me. I almost jumped out of my skin from the scare. Felicity took the scissors from my hand, held them a few inches from my crotch, then opened and closed the blades a couple of times for effect. The act had me backing up in apprehension. “Yes, these ought to do the trick just fine,” she said while looking at her target with a fiendish grin.

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

“Oh, for crying out loud, how pathetic." She grabbed a few strands from the hair on my head and acted as if she was about to cut them off. “Okay, then, we’ll just start right here and work our way down.”

“Okay! Okay!” I cried, while standing up.

She looked down at her objective, then paused, putting her fingers to her chin, as if deep in thought. This, I knew, could not bode well for me. “Let’s have some fun with this, Blondie,” she said, eyes widening as if a light had just turned on in her head. “You did so well singing ‘Happy Birthday.’ Maybe you can sing for me again. Are you familiar with ‘Old MacDonald Had a Farm?’ ” I nodded wretchedly. My stomach was in knots. “Great! We’ll use the same tune, but we’ll plug in our own lyrics. Let me think…” She paused for a few seconds while I stood there, wishing for death.

“I know! It goes like this: ♬‘Pretty Blondie lost his hair, ee-eye-ee-eye-oh. With a snip-snip here, and a snip-snip there, here a snip, there a snip, everywhere a snip-snip, pretty Blondie lost his hair, ee-eye-ee-eye-oh.’♬

Now the beauty of this is (I must tell the reader that she had a maniacal look in her eyes as she spoke) that every time you sing the word ‘snip,’ I snip off a little bit of your pubic hair. So essentially, you’ll control the tempo of the snipping with your singing. The more you sing, the balder you’ll get down there. Won’t that be a fun game, Blondie? Oh, I just marvel at my creativity sometimes." She paused while grinning and staring at me. “Okay, anytime you’re ready, sweetheart. Do you want to practice before we do the real thing?” I shook my head sullenly. She inched closer to me, her weapon at the ready. “Oh, do me a little favor, sweetie, and hold your little pee pee down and out of the way. I’d hate to miss and snip the little thing off, know what I mean?” She laughed aloud, obviously quite amused with herself. I pushed down my penis with my hand; I certainly didn’t need an “accident” to add to my suffering. There was silence for a few seconds. Felicity stood by anxiously. “Any time now, Blondie.”

♬“Blondie, Blondie, lost…”♬

“No, no, it’s pretty Blondie. Now start over.” She was really keyed up.

♬“Pretty Blondie lost his hair, ee-eye-ee-eye-oh. With a…”♬

I hesitated, momentarily unable to continue. Felicity gave me a look of admonition.

♬“With a snip-snip here…”♬

I winced as I watched a small amount of my precious pubes gravitate unfettered to the carpet.

♬“And a snip-snip there, here a snip, there a snip, everywhere a snip-snip…”♬

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

♬“Pretty Blondie lost his hair, ee-eye-ee-eye-oh.”♬

“Excellent, Blondie. Excellent!” Felicity was literally hopping up and down with joy.

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

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

Again I sang the sordid song, and again eight more snips were taken from my pubic hair.

“Let’s do it again!” The child in her was on display; she was captivated with her little game. After the third go-round, there was a noticeable degree of hair loss. My feeling of despair was momentarily overshadowing my embarrassment. Felicity handed me the scissors. “Now you do the snipping, Blondie. While I sing. You’ll see, it’s really fun!” She gave me no time to argue.

♬“Pretty Blondie lost his hair, ee-eye-ee-eye-oh. With a snip-snip here…”♬

She sang, and, with incredulity, I snipped. She put her head down close to the action and emphasized the word ‘snip’ each time she sang it, laughing as she watched the amount of my hair lessen ever so gradually. When she finished singing, she again jumped up and down excitedly, clapping her hands. I was starting to think that she was positively deranged.

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

And so we did. We passed the scissors back and forth seven or eight times, trading off singing the dreadful song until there was nothing left to cut.

Felicity was the last to have the scissors. She placed them on the dresser, then leaned over to scrutinize the fruits of our labors. There was still some stubble remaining, and she wrinkled her face. Becky had a small bathroom attached to her room, complete with a shower. Felicity grabbed my elbow and led me toward the bathroom. “We have to finish the job, Blondie, until you’re totally bare down there.” She proceeded to turn on the hot water in the sink, holding a facecloth underneath the faucet. “I’ve seen my daddy soften his beard with hot water. This will make it easier, and you’ll be really smooth.” She then found Becky’s pink razor and some shaving cream in the shower and handed it to me. “Here, you have to do it. I’m afraid I might cut you.” She paused. “Unless you want me to get Mitch in here to do it for you." She laughed to herself while she handed me the hot, wet facecloth. “Here, hold this over that stuff you have left for a couple of minutes.”

She reached down and without warning took hold of my balls and strummed her fingers across my scrotum. Startled, I jumped back, letting out a high-pitched squeal, much to Felicity’s amusement. “I think you’ve got a few hairs on your little balls, so wrap the cloth around those, too.” She was making sure that I would be totally denuded. Under her supervision and direction, I shaved off the last vestiges of my bodily hair. She handed me a towel, and I dried myself off. Self-consciously, I covered myself with my hands.

“Put your hands behind your back, let me see,” she ordered, all too eagerly. I did, and Felicity grinned brightly while staring at my smooth-shaven genitalia. “Now it looks just like Joey’s.” My face flushed brighter, and again the little girl laughed joyously. “Come, let’s have a look in the mirror.”
She took me by the hand and led me to the full-length mirror. She stood next to me, and we both looked at the reflection. “Go like this.” She put her arms above her head, holding her left elbow with her right hand, and her right elbow with her left hand. I followed suit and was taken aback by the sight of an apparently prepubescent sixteen-year-old boy. I wanted to cry, but I was beyond tears. “Ooh, wait ‘till everybody sees this! You look like a little boy, Blondie. And you're sixteen!" She looked at me and grinned, then began singing.

♬"Pretty Blondie has no hair, ee-eye-ee-eye-oh."♬

She looked me up and down, grinning broadly. "How does it feel to have no hair, Blondie?"

I didn’t answer. I just stood there, staring at the mirror in disbelief, drinking the full cup of degradation.


The Babydoll

Felicity brought me out of my stupor when she pulled the pink babydoll over my head. “See, I'm keeping my promise and letting you wear this.” It had short, fluffy sleeves, and the lacy hem dropped just below my balls in the front, and barely covered my ass in the back. I nervously tried to pull it down further, but there was no give.

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

“Nonsense, sweetheart, it’s perfect. I know it seems short, but you have such pretty legs, it would be a shame not to show them off. I’ll tell you what—I won’t make you put on panties. Your babydoll is so short, your panties would show. You wouldn’t want that, would you Blondie?”

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

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

“Oh, sweetie, what a good girl you’ve become. Turn around, let me show you something.” I turned around miserably, my back to the mirror. “Now turn your head and look in the mirror.” When I did, Felicity lifted the babydoll halfway up my back, exposing my bare ass. “If you wear panties, then Mitch won’t be able to see this. We don't want to deprive him of seeing your cute little tushy, do we?” I blushed yet deeper, and Felicity afforded herself yet another hearty laugh.

My feeling of humiliation was surpassed only by my sense of dread.
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Roosevelt Humiliations, Chapter 23

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Chapter 23: Shake That Ass!

Yet More Feminization

“I think it’s time we go join the party, Blondie,” declared the smiling Felicity. “Your guests are anxiously waiting for you. I’m sure Mitch can’t wait to see you.” Felicity looked at me and grinned wider, amused by my blushing face. She teased me by lifting the front of the babydoll for one last peak at my now-smooth genitals. “You’d better be careful out there, Blondie, or they’ll discover our new little secret.” She paused for effect. “And I do mean little.”

The 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.

When we reached the clearing of the entrance to the living room, 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, how adorable!” she teased. “Come, come, you must say hello to your new guest.” She took my hand and pulled, and I reluctantly followed her to where Mitch was sitting on the couch. I self-consciously pulled down on the hem of the babydoll, unsuccessful in my efforts to cover my naked thighs.

“Blondie, it’s a pleasure to see you,” said Mitch, his eyes lighting up as he focused his gaze on my smooth legs. He reached out and ran his fingers up my leg, starting at my ankle. When he reached my knee, I backed away before he reached my thigh. I blushed crimson as the girls giggled merrily.

“That Blondie, always playing hard to get, isn’t he?” said Brenda. “Come over here, sweetie, I’ve got a surprise for you.”

Brenda was on the other end of the L-shaped couch. I nervously walked over to her, not at all excited about any surprises that she had for me. She patted the vacant spot on her left. “Have a seat, princess.” I did so, vigilantly pulling down on the hem of the babydoll as I leaned back on the sofa. I winced noticeably when Brenda reached into her purse and pulled out a tube of lipstick. “We need to pretty you up a little more, sweetheart. I know you want to make a good impression for your new boyfriend, don’t you?” I turned away from Brenda without answering, looking down at the floor. “Turn toward me, let’s fix you up,” she said, while taking my chin between her thumb and forefinger and turning my head to face hers. I watched gloomily as Brenda opened the bright red lipstick and painstakingly applied it to my lips.

Meanwhile, Julie had inched her way close to me on my other side and was stroking her fingers up and down my left thigh. “Oh, Blondie, I just love your pretty legs. They’re soooo nice and smooth,” she giggled.

The other girls joined in her giggling, and somehow I managed to blush brighter, which was not lost on Brenda. “Well, we certainly don’t need to put any blush on you,” she said, grinning. “Your cheeks are bright red already. And I don't think that's going to go away any time soon.” Brenda returned the lipstick to her purse and pulled out some more makeup. “Time to enhance your pretty eyes, girlie-boy.”

While I sat there miserably, Brenda proceeded to carefully apply light blue eye shadow on me, followed by mascara on my eyelashes. During this time, Julie was strumming her fingers lightly up and down my hairless left arm. “I love your little girlie arms, Blondie; they’re so cute!” said Julie. Again, the sound of giggling girls resonated throughout the living room.

Brenda returned the eye makeup to her purse and sat up straight, tilting her head back slightly to inspect the results of her efforts. “Oh, how lovely you look, princess. I’m so jealous. You look prettier than I do,” she teased mercilessly. I remember thinking that it was scary, but she was probably right. Brenda was dressed in a pair of old jeans and a sweatshirt, and here I was, smooth-shaven in a short, sexy babydoll and becoming more feminized by the second. “Oh, just one last touch, sweetie pie,” she said, as if just remembering something. She reached into her bag of tricks, this time pulling out a small spray bottle. “Tilt your pretty head back a little bit, princess,” she directed, while gently helping me along by lifting my chin. “That’s a good girl.” Brenda then sprayed some perfume to the top of my neck and followed that up by lifting my right hand and spraying some more on the inside of my wrist. She leaned toward me and gently touched her nose to my neck, sniffing softly. “Mmmm, mmm, you smell delicious, princess.” She tugged lightly on the side of the babydoll. “You better be careful, or Mitch might just rip this thing right off and ravage you right on the spot!”

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


Shake that Groove Thing

When the laughter subsided, the energized Felicity sprung in front of me and took hold of both of my hands, pulling me up. “Come, Blondie, you must see how pretty you look.” She eagerly pulled me in front of a decorative, full-length mirror near the fireplace. I couldn’t help but notice in the reflection that Mitch was staring at me, grinning lecherously. As Felicity stood next to me, beaming, I looked at my reflection and couldn’t believe what I saw. With my youngish, soft features and my hairless arms and legs, if I didn’t know better, I could have mistaken myself for a twelve-year-old girl with a boyish haircut. Felicity wrapped her arms around me and kissed me on my blushing cheek. “Oh, Blondie, you make such a cute young lady. I feel like I’ve found a new girlfriend tonight.” She giggled to herself and made a motion to lift the front 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 quickly pulled her hand away. Again the little devil giggled freely.

“Can you show Mitch your froufrou undies, Blondie?” asked Marcia mischievously from her seat in the middle of the couch. Obviously, she (along with everyone but Felicity and me) was not aware that Felicity brought me out there without a stitch on underneath the babydoll. I flinched noticeably, fearful of where this was heading. I stood there transfixed, unable to move.

“Oh yes, Blondie,” chimed in Joanne, “Show us your pretty panties again.”

“Hold on, I’ll be right back,” said Felicity as she darted down the hallway toward the bedroom. She quickly returned, holding the panties in question high in the air with both hands. The grin on her face was pronounced.

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

“Does this mean…?” Cheryl was interrupted by the impish Felicity.

“Let’s just say that if we were to take off Blondie’s babydoll, then he’d be wearing nothing but a bright blush on his face.”

“Ooohh!” exclaimed Mitch and the girls.

Indeed, I was blushing ever so brightly. 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 other 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. It was Felicity, yet again, who took control of my next humiliation. Taking me by the hand, she led me to an area a few feet in front of Mitch, facing me away from him. She stood directly in front of me, looking me in the eyes with a devilish grin on her face. “What do you think, Blondie, shall we show Mitch and the girls whether you're wearing panties or not?"

“Please, don’t do this,” I pleaded. It was the first time that I had spoken since Felicity brought me back out there.

Naturally, my appeal fell on deaf ears. “Put your hands on my shoulders, Blondie.” Grudgingly, I complied. “Are you ready, Blondie? Are you ready to show Mitch your sweet cheeks?” She giggled, and in my fear my breathing became faster. Felicity inched closer to me, then reached around me with both hands, taking hold of the back hem of the babydoll. “Look at me, Blondie.” When I did, she raised the back of the babydoll halfway up my back, exposing my naked derriere. I flinched, involuntarily squeezing my ass cheeks together. A loud uproar arose from behind me. I looked at Felicity, who was obviously filled with excitement over her latest stroke.

“Look in the mirror, Blondie,” she instructed. I looked up at the mirror on the wall and could see the grinning faces of Mitch and the other six girls as they stared at my naked condition. A sick feeling came over me as I swear I saw Mitch make an adjustment to his crotch. “Swivel your hips for them, Blondie,” ordered Felicity, as she held the material of the babydoll against my waist and helped me along by rotating my hips in a 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 downright unbearable.

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

Becky, not one to let an opportunity go by, hurriedly slipped a Jennifer Lopez CD into the stereo. The song was called “Let's Get Loud,” and it had a fast beat to it. Becky cranked up the volume. “Shake it, Blondie! Shake that ass!” screamed Brenda and a couple of the other girls.

With their screaming and Felicity’s not-so-subtle prodding with her hands, I reluctantly began swaying my hips from side to side. My movement didn’t quite keep up with the music.

“Faster, Blondie, faster!” they screamed. I shook my hips faster, much to the amusement (and stimulation) of my audience.

“Oh, I have to see this!” cried Felicity. “Here, Blondie, hold up your babydoll for me.” Now absolutely miserable, I reached back and held up the babydoll. I momentarily slowed down my hips. “Keep shaking it, Blondie!” ordered Felicity as she stepped behind me. “Faster, faster!” She swatted my ass a couple of times for good measure. I sped up my hip movement, while listening to Mitch and the girls whooping it up behind me.

“Go Blondie! Go Blondie! Go Blondie!” yelled a few of the girls in unison—with more than a little derision to their tone, I might add. They clapped their hands and screamed “Go Blondie!” and “Shake that ass!” 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 muster up the courage to relate to you what else happened to me during the next portion of the most humiliating night of my life.
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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 song finally came to an end, I dropped the babydoll back down while everyone clapped and cheered.

“Bravo, Blondie, Bravo!” shouted Felicity.

The laughing thirteen-year-old turned me around to confront the approving audience. I blushed brightly when I saw the leer on Mitch’s face. Then I looked in dismay as I spotted Julie reaching into her bag of tricks. My dismay proved to be justified when she pulled out a pair of pink high-heeled shoes. I had a suspicion that they weren’t for her.

“Come here, Blondie,” beckoned Julie, who was sitting on the couch. “I have something to match your pretty babydoll.” While everyone giggled with delight I slowly stepped over to Julie. She lifted my left foot by the ankle and placed one of the shoes on my foot. “Ah, a perfect fit,” noted Julie, with a tone of satisfaction. “These will set off your pretty legs quite nicely,” she teased, while running her hand up and down my smooth calf. She slid the other shoe on my other foot. When she put my foot back on the ground I lost my balance and fell forward, breaking my fall by landing my hands on Julie’s shoulders. 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 reached behind me and pulled the babydoll all the way up to my shoulder blades. Her legs were wrapped around my thighs to keep me from sliding off. To my consternation, I noticed the flash of a camera go off. She pumped her pelvis back and forth, which forced my hips to bounce up and down on top of hers.

“Help, I’m being attacked by a lesbian!” screamed Julie.

Uproarious laughter filled the room, as I frantically tried to escape from the compromised position. 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 slapping. “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 finally stopped spanking me. “Ooh, look how red his little fanny is getting,” she said.

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

The center of attention was now my bare ass, which I’m sure had to be turning an increasingly darker shade of red, considering how much it was throbbing. There was another flash from a camera, quite probably capturing a picture of my tanned hide.

At one point my sister Becky laid her hand on one of my butt 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 my ass, he rubbed his hand all over, and then slid a finger along the crack, brushing across my asshole and stroking my perineum. This caused my whole body to flinch, eliciting a chorus of laughter from my tormentors. 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. “You’d better be careful, Mitch. I think you’re getting Blondie excited.”

There was laughter all around. Then 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 now 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,” declared Julie, laughing away as she made a move to get up.

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 tops 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 high heels.” She pulled me up, and I wavered momentarily while I caught my balance. “Birthday girl, would you like to give me a hand showing Blondie how to prance around in his new shoes?”

Felicity needed no further prompting. “With pleasure, my dear sister,” she replied. She eagerly took my one hand, while Julie held on to the other. Marcia and Mitch jumped up and moved the table and a couple of chairs, clearing the way for the three of us to parade back and forth across the very large living room. Mitch and the other five girls all sat on the couch, anxiously awaiting the demonstration. Julie and Felicity began walking me away from the captivated audience.

“Okay, sweetheart,” instructed Julie. “When you walk, you should take very short steps, and put one foot in front of the other, as if you’re stepping on an imaginary line. Like this.” We stopped, and Julie let go of my hand and walked in front of me, demonstrating her womanly gait. I noticed that her hips naturally swayed seductively from side to side when she walked. “Okay, now you try it,” directed Julie. 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?” Julie was tilting her head back, watching my backside as she said this. “’'Cuz I want to tell you; you’re sashaying like a lingerie model on a catwalk right now.” Again, boisterous laughter abound.

We walked all the way across the room (about fifteen paces or so), then turned around and started back. At first my steps were very awkward, but gradually they became easier. 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. “As you can see by their smiling faces, Blondie, your audience is very supportive of your efforts. It would be a very nice gesture if you would curtsy for them every time we return here.” 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 genuflected. I was blushing profusely.

“That wasn’t bad, Blondie, but you need to look your audience in the eyes. Let’s try it again.” Difficult as it was, I repeated the ignominious act, this time while looking into the eyes of my leering tormentors. My face flushed yet brighter. To exacerbate my already hopeless plight, I noticed that Becky had the video camera pointed at me. “Nice curtsy, Blondie,” approved Felicity. “Now it’s time to strut your stuff again.”

Julie whispered something to Felicity, who responded with a childish giggle. I knew this couldn’t bode well for me.

“I think you’re ready to try it on your own, princess,” said Julie. “We’ll be right at your side in case you have any trouble. Remember, teensy, mincing steps, and put one foot in front of the other. Ready? Here we go.” I started walking (okay, “mincing”) away from the couch. This time, after a couple of steps, the two girls reached back and lifted the back of the babydoll, much to the delight of the onlookers.

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

“And look at it sway back and forth!” added Joanna. “Oh, this is a riot!”

Somehow my ass smarted a little more; I swear I could almost feel everyone’s stare on it. When we got to the other side of the room, Julie and Felicity 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 really 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. He blushes just like a little girl,” responded Becky with a giggle.

Once again I walked to the other side of the living room, and once again Julie and Felicity held up the back of the babydoll. 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. When I reached the other side, I turned around and prepared to walk back. But Julie stopped me and gave me further instructions. “Okay, sweetie,” she smiled. “This time, while you walk back to the couch, I want you to go like this.” Julie coached me by demonstrating what I had to do. She put one hand behind her head with her elbow sticking straight out to the side, and she made a fist with her other hand, resting it 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.

Once again, I reached the couch and curtseyed to the group, then turned around and walked 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 or seven 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 up and down 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, Blondie,” was all 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, don’t do this. Please, I’m begging you.”

“Well, maybe if you ask me very 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?” I knew I had to answer.

“Please don’t make me take this off.”

"Take it off!" yelled Joanna. 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. “Arms up, Blondie.”

“No, please…”

“Arms UP, I said!”

I slowly raised my arms high in the air. It took her about one second to strip the babydoll off my body, leaving me naked but for a pair of pink high heels. I immediately covered my bare crotch and leaned over. Felicity calmly put the babydoll on the coat hanger and hung it from an empty plant hook conveniently hanging from the ceiling from a short rope. It swayed back and forth momentarily before coming to rest. She walked back over to me. I stared at her feet without looking up. “Stand up, Blondie.” Slowly I rose, being careful to keep my hands over my hairless genitals. I glanced up at Julie, who was now grinning from ear to ear. I quickly averted my eyes from her.

"Make him turn around!" shouted one of the girls from behind me.

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

“Okay, Blondie,” she continued. She was relishing her feeling of control. “Since my sister was kind enough to introduce me to you tonight, I’m going to let her be the first to discover our little secret. I’d like you to look Julie in the eyes and put your hands on your hips.”

“Please, Felicity…”

“DO IT!”

I had to obey. While staring at the delighted Julie, I pulled my hands away from my crotch and placed them on my hips. My face pulsated with embarrassment as I watched Julie’s wide-eyed, amused expression turn to one of utter hilarity. She put one hand over her mouth and used her other to point at my hairless dick and balls, while collapsing to her knees into a fit of uncontrollable, convulsive laughter. “Oh, shit, this is too much!” she managed to spit out between laughing spasms.

“Hey, we want to see!” screamed Cheryl 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 hand on your hip. Elbows out.”

I grudgingly followed her order, and 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 like we taught you. 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 reached behind me and slapped me hard on my ass. I slowly turned around and started mincing toward the couch. It was an excruciating experience, as one can well imagine.

“Oh, my God!” shrieked my sister Becky. “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. I was absolutely miserable.

"He's completely hairless!" shouted the entertained Brenda.

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

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

“He’s got a cleanie teeny peenie weenie,” joined Brenda.

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 looked over at Mitch, who was being very quiet at the end of the L-shaped couch. To my revulsion, he was kneading his crotch with his right hand. I quickly turned away.

Felicity and Julie had joined the group on the couch. Felicity was positively beaming, quite proud that she was responsible for the present state of merriment.

I stood there for what seemed like an endless amount of time, while everyone soaked in my utter humiliation. When the laughter finally subsided somewhat, Becky spoke up. “So, Blondie, how did you get so…so bald?”

The laughter picked right up where it left off. I stood there without answering. After a couple of minutes, Felicity spoke up. “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.”

Wild, uproarious laughter echoed throughout the room. 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 would alternate between closing their eyes in their fits of laughter, then looking up at my glowing face, down to my hairless little package, then laughing some more. All I could do was stand and soak up the intense humiliation, wishing the floor would open up and swallow me whole.
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Blondie
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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 settled down somewhat, Brenda went into the kitchen and returned carrying a high barstool. She set it down right behind me. “Have a seat, smoothie. Rest your weary legs. We girls know how tiring it is to walk around in our heels.” I climbed onto the barstool, put my knees together, and leaned over, folding my arms on top of my thighs. Brenda would have none of it. She stood behind me and pulled me back by the shoulders, so I was leaning against the back of the barstool. “I want you to be comfortable, Blondie. Just kick back, relax, and enjoy yourself.”

Right, like that’s even remotely possible.

She took hold of my wrists and rested them on the arms of the chair. “That’s it. Just rest your arms here.” Brenda then pulled my knees apart, took hold of my ankles and placed them on the leg rests on opposite sides of the chair, leaving me exposed to the max. “We’re all friends here, sweetheart, what’ve you got to hide?” She looked down at my naked crotch. “Very little, from the looks of things.” She sat back down on the couch to the accompaniment of animated laughter.

After the laughter subsided, Becky broke the silence. “You’re awfully quiet, Blondie,” she said. “Say something. We never talk anymore.” Everyone seemed to sit up a little in their seats, in anticipation of my verbal involvement, which up until now had been virtually nonexistent. I was in no mood to talk; it would only add to my humiliation. Of course, the sadists sitting across from me were keenly aware of this. “We’d really like to hear about your time alone with Felicity a little earlier,” prompted Becky. “You were gone for almost an hour; 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, Becky waited for the inevitable laughter, and she wasn’t disappointed. “Not only that, but we also have several pictures of you mincing about in pink high heels, and a wonderful video that we’re all going to sit around and watch over popcorn tomorrow night. 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.

“Good.” Becky leaned back in her seat and took a sip of beer. “Let’s see, when I opened the door to tell you that Mitch was here, you were in quite the compromised position. Why don’t you tell us about that, Blondie.”

It was apparent that I would be forced to partake in revisiting my earlier debasement. Marcia now had the video camera focused on me. “Felicity made me take off the clothes I was wearing,” was all I said.

“I’m warning you one last time, Blondie,” admonished Becky. “We want details. All the details.”

I took a deep breath. “When you came in, I was standing on the stool. When I got on it I was only wearing the panties. Before that she took off my shoes and socks, the dress and the petticoat.” I stopped momentarily, fidgeting nervously. Everyone was smiling at me, enjoying my discomfort, and the story.

“Go on,” prodded Becky.

“Then she started pulling down the pan…”

“Hold it, Blondie,” interrupted Felicity. “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 continued.

“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 took another deep breath and looked up at eight expectant, smirking faces. “First she used scissors…please, don’t make me tell this.”

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

“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!” interrupted Becky. “Back up. You had to sing? Was it ‘Happy Birthday’ again?”

“No, she made up another song. Please…”

“Oh, do sing it for us, Blondie.” Becky held out both hands and asked her guests, “Would you like to hear the song Blondie sang while the little hairs on his little pee pee were coming off?” Of course, a unanimous chorus of affirmatives ensued. “Sing it for us, sweetheart.”

I had a very hard time with that one, but I managed to spit it out. Once again I sung the dreadful song, to the tune of “Old MacDonald.”

♬“Pretty Blondie lost his hair. Ee-eye-ee-eye-oh.”♬

They were laughing quite heartily now.

♬“With a snip-snip here, and a snip-snip there. Here a snip. There a snip. Everywhere a snip-snip. Pretty Blondie lost his hair. Ee-eye-ee-eye-oh.”♬

Everyone on the couch was clapping and laughing at that point. Mitch was stomping his feet up and down, seemingly near delirium.

“Tell them about the snips, Blondie.” The voice was Felicity’s. I think she was quite proud of herself of that particular part of my debasing experience at her hands.

“W-Whenever I sang the word ‘snip’ she snipped off some of my hair down there with the scissors.”

That information elicited quite the raucous reaction from the entertained group on the couch. When things settled down, Becky offered her praise. “Ingenious, Felicity. Positively ingenious.”

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

“I have a question,” interjected Brenda.


The “Before” Measurement

All eyes turned toward Brenda as it quieted down. She paused momentarily while everyone waited expectantly. “Is it true that if a guy spends time in the pool that his penis shrivels up?” Naturally, all eyes immediately focused on my smaller-than-average penis. My self-consciousness, already at a very high level, somehow became more exaggerated. I tried closing my knees, but the positioning of my legs on the chair restricted their movement.
“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 nip this conversation before it advanced any further. But my hope was soon shot down.

“It’s true,” stated Mitch matter-of-factly from the end of the sofa.

Felicity was ready with her next jab. “Well,” she said with a tone of mocked disbelief as she pointed at my penis. “It can’t get any smaller than that, can it?” Once again, the redoubtable Felicity had elicited laughter from the entertained group.

“There’s one way to find out,” stated Becky when the laughter started dying down. All eyes momentarily moved from my crotch over to Becky. She stood up, and I looked at her, horrified, quite aware of what she had in mind. She took both of my hands in hers and pulled me from the chair. “Come, sweetie pie, let’s take you for a dip.”

The rest of the group sprung from their seats, enthusiastic about the new devilish plan. Becky reached down and pulled the high heels from my feet, tossing them aside. She took me by the hand and led me toward the hallway. “Let’s go in the bathroom and clean off your face. We wouldn’t want your makeup to dirty up the pool.”

“Please, Becky, the pool’s not even heated,” I pleaded.

“Precisely, my dear,” responded my unmerciful sister with an unmistakable twinkle in her eye. She pulled me into the bathroom and quickly went to work on removing the makeup from my face. She yelled out to her cohorts. “You all might want to put on a sweater or something,” advised Becky. “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 really is 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 cold 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. I was snapped out of it by what sounded like a loud pop, like the crackling of a fire. A split second later I felt a stinging sensation, and it registered that I had been slapped on my ass. A giggling Julie put her arm around my bare waist. “Let’s go, cute cheeks,” she teased, while patting me gently on my ass. She looked down at my crotch. “It’s time to see if your little weenie can get any weenier.”

While giggling at her derisive remark, she 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 above her head a roll of measuring tape. A few inches of the tape dangled from the roll. “We need to get a ‘before’ and ‘after’ measurement,” she said with a wicked smirk. Everyone leered at me. “Who would like to measure Blondie’s little winkie?” asked Becky. Several of the girls excitedly expressed interest. “Well,” laughed Becky, “You can’t all do it. Let’s let the birthday girl do the honors.”

The delighted Felicity sprung forward. “Oh, goodie!” she yelled while snatching the tape from the grinning Becky. I watched dejectedly as Felicity approached me. She looked up at me and smiled. “Isn’t this fun, Blondie?” she teased. I remained silent, unbelieving of what was transpiring. Felicity looked down at her objective. “Becky,” she requested, “Would you mind holding his little thingy straight out while I measure it?”

“Sure,” laughed Becky. She placed her index and middle fingers underneath my penis and held it out. The humiliation of my sister handling my penis under the extremely embarrassing circumstances was torturing.

Felicity stretched the tape across the length of my penis. To obtain a reading, she lowered her head very close to my midsection and squinted at the numbers. I felt her hair brush against my bare stomach. “It looks like two and one-eighth inches,” she announced gleefully. This declaration elicited 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,” declared Cheryl.


The Pool

The door swung open, and the jubilant group led me outside. The pool light was on, and the entire area was well lit. The chilly air—I’d say the temperature was in the mid-forties, and there was a steady breeze to boot—sent shivers throughout my body, and immediately produced goose bumps all over. I folded my arms across my chest in a futile attempt to stay warm.

“B-r-r-r,” said Joanna. “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 need to go in the pool, little boy," taunted Becky. "I think it’s already shrinking.” The comment elicited another chorus of laughter, and I self-consciously lowered my hands and covered my shriveling package as we approached the pool.

“Let’s see,” mused Becky. “How do we want to do this?” She paused momentarily before continuing. “Why don’t you use the slide, Blondie? I know how much you like the slide.”

I lowered my head and made my way to the ladder to climb to the top of the slide. It was a fair distance to the top. I had made the climb hundreds of times in the past, but never naked, and never with such a sense of dread. As I made the fateful climb I heard more laughter, both at the comical sight of their naked victim, and in gleeful anticipation of what was to come. I reached the peak and sat on the top perch. I heard the chanting from thirty feet below.

“Go Blondie! Go Blondie! Go Blondie!”

I hesitated a few more seconds and then 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 underestimated its extent. Anyone who has jumped into a swimming pool knows there is an initial jolt, but I’m here to tell you that I’d never experienced anything like that one. 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!” I screamed. My tormentors were laughing and cheering. I swam toward the side of the pool, intent on getting out.

“Uh, uh, uh!” admonished Becky as she used her foot to obstruct my effort to climb out of the pool. “You need to spend a few minutes in there, Blondie boy, to get the full effect, if you know what I mean.” She paused and giggled to herself. “Now go out to the middle of the deep end and stay there until we tell you to come out.” I obeyed, and treaded water for what seemed an interminable amount of time, shivering all the while.

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

“I’ll say,” chimed in Julie as she bent from the waist and peered in my direction. “I can hardly see it!” she exclaimed, eliciting more hearty laughter.
I reached down and surreptitiously checked it out myself. Much to my dismay, there indeed had been a change. The cold water had done a number on my penis. There was nothing there but a little nub! “Oh, God,” I said to myself in a semi panic. I turned my back to the group and pulled on it, hoping against hope to pull it from its depths. But the forces were against me. My humiliation would be exacerbated in a few short minutes.

“Okay, Blondie,” called Becky a few minutes later. “Come on out, let’s have a look.”

Reluctantly, I swam toward the side of the pool, where eight people waited for me, all with amused faces, anxious in expectation. Before I climbed out, I pulled on my diminutive penis in one last effort to somehow resurrect it to its regular size.

I don’t think it helped.

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

“Put your hands on your head and keep them there!” ordered Becky. I raised my hands to my head. Between the stinging on my ass, my shivering from the cold, and my excruciating humiliation, I was in the throes of wretchedness.

“Oh, this is too much!” exclaimed Joanna.

Everyone’s gaze was fixed on my crotch. I think everyone was momentarily overcome with astonishment, and there were a few seconds of silence.


(Not) Measuring Up

“Come, let’s go in the poolroom and get a measurement,” said Becky. She took me by the hand and hurried me into the poolroom. Of course, everyone eagerly followed. It was warmer in there, but I was dripping wet and continued to shiver. A camera flashed, and I could also see that Mitch was taking a video, focusing between my legs. For the first time, I afforded myself a look at my shrunken state. 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 sticking 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 your help this time, Becky,” she stated gleefully to yet more laughter. “There’s nothing to hold up anymore.” 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 one-eighth inches!” she proclaimed, much to everyone’s utter delight and amazement.

“Such a cute wittle baby boy,” taunted Becky as she took a chunk of my profusely blushing cheek between her thumb and forefinger and tweaked it lightly.

“Does wittle Bwondie need to put on his diaper?” mocked Julie.

The hilarity was now at its highest point of the evening, as was my mortification. I stood there helplessly, hands on my head, still shivering, and taking in the extreme humiliation. Cheryl lowered the camera to the object of everyone’s amusement and snapped a couple of pictures. Mitch zeroed in, capturing his 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.
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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. This will be hard for me to detail, as the humiliation I suffered was extreme, and I don’t think that I’ll ever fully get over it.

When I left off with you 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. The girls and Mitch were having a marvelous time at my expense and were feeling the effects of the alcohol, which was making them rowdier, and, as you’re about to see, bolder.

The poolroom was fairly good-sized and comfortably furnished. Besides the furniture there was a pool table, a full-sized bar and a stereo. The room was well lit, the stereo was playing, and the atmosphere was one of merriment, save for one dissenter. That would be the naked sixteen-year-old, whose state of humiliation was already extreme, and who could sense that it somehow was about to degenerate even more for him.

“How about a game of eight ball?” suggested Julie.

“I wanna play!” chimed in Felicity as she plucked a cue stick from its receptacle.

“Okay then,” said Julie, who did likewise. “I’ve got it: Let’s play the girls against the boys. Blondie and Mitch can play against Felicity and me.”

Everyone seemed quite pleased with the idea. I winced noticeably. Once again I would be taking an active part in my humiliation.

“What kind of stakes are you playing for?” asked Brenda devilishly. There was a few seconds of silence while their mischievous minds worked actively.

“I know!” exclaimed Julie. We all looked at her—everyone else in anticipation, and me with dread. “The two that lose have to give each other a big wet kiss on the lips.” There was a raucous reaction to Julie’s devious suggestion. She waited for the noise to subside, then continued. “And I’m not talking about a little peck, either. It must be at least thirty seconds long, and there must be some serious tongue action.”

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,” said Mitch. 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. He was still grinning.

“You break, Blondie,” directed Julie while she arranged the balls with the triangle-shaped rack. I paused, closing my eyes tightly while pressing a fist against my forehead, trying desperately to psyche myself up. Now, normally I would regard myself as a halfway decent pool player, but under the circumstances, considering the stakes and me being naked and all, I think you can readily see that I wouldn’t exactly be in my comfort zone. But with the stakes being what they were, I knew that I couldn’t just go through the motions. I obviously 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 looked into the panties I was wearing to steal a peek at my privates.

God, that seems like ages ago.

“Solids,” she proclaimed as she momentarily lifted the two-ball into the air above her head before placing it back in the pocket. I surveyed the table and was pleased to see that I had at least three easy shots set up. The seven-ball in the corner pocket looked like the easiest, and the ball 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 gave my nuts a gentle squeeze.

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

“That’s a scratch,” laughed Julie as she reached into the side pocket to remove the two-ball. Everyone laughed heartily while I blushed crimson yet 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 hope. “Sorry, little sister,” she said to her partner.

“No problem, you were awesome,” answered Felicity, who then kissed her elder sister with a peck on the cheek. She paused for effect. “That’s the only kissing you and I will be doing tonight,” she said while looking at me for a reaction. She was answered by my blushing face and animated laughter from everyone else.

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 good 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 sung 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, and 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. Holding it there, 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.

Cheering and clapping broke out. I could sense all gazes on me, and I could only stand there, my eyes transfixed on the table, where seven solid balls remained, 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, much too eagerly for my liking, advanced toward me.

“Hang on a sec,” interjected Becky. She walked swiftly to the stereo and rummaged through the sizable CD collection. “Ah, here we go—the ‘Final Jeopardy Countdown.’ This is perfect; it’s exactly thirty seconds long.” I bemoaned 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!”

To the tune of “Final Jeopardy” my ordeal began. “It’s just you and me, Blondie boy,” said Mitch as he pressed his lips to mine.

“Ew, gross!” shouted Felicity, without really meaning 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 entertained girls laughed boisterously (interspersed with several “whoas” and “oohs” at Mitch’s aggressive advances). The song seemed to me like it would go on indefinitely. I clenched my eyes shut tightly throughout, ever so reluctantly enduring the passionate assault from my antagonist.

The tune finished at long last, and I immediately retracted my face from his. 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!” shrieked Becky suddenly. She darted out of the poolroom and ran the circuitous route around the swimming pool. “I’ll be right back!” she yelled before entering the house. Everyone turned and looked out into the night, wondering in delicious anticipation what devious scheme my sister had up her sleeve. I bowed my head, all too aware that my torment was going to continue.

In a matter of moments, the back door of the house swung open and Becky, short of breath, re-entered the poolroom. In her right hand she carried an unknown object rolled up in a small pink hand towel. She laid her possession on the pool table. The mysterious item remained obscured by the towel. She chose to temporarily ignore the object in question and directed her attention to me. “You’re putting on such a nice show for us, sweetie; I’d hate to see you stop now while you’re on such a roll.” She turned around and slowly, deliberately started unrolling the towel. She continued speaking to me as she did so, knowing just how to draw out the suspense for her expectant cohorts. “You’ve demonstrated quite well your strong feelings for Mitch, and we can see that you know how to kiss.” She had turned toward me, still slowly unrolling the towel. “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 quite closely. 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 gave me my 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 belongs to 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 penis. 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. I didn’t think my humiliation could get any worse, but I would soon find out otherwise. 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 advancement caused me to retract my hips and let out a high-pitched yelp. I lowered the dildo from my mouth. “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. “Put it in your pretty little mouth and start sucking on the tip a little bit, 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 abounding as I carried out the shameful charade.

“I wonder how big Blondie’s little pee pee gets when he gets excited?” mused Felicity when it quieted down a bit. 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 believe. 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.” There was an unmistakable gleam in her eyes. An energetic reaction ensued when it hit home to everyone 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 productive mind seemed to always be working, and it unfailingly was 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 tiny 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!” commanded 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 cums.” Everyone laughed and I flushed brighter. The reference to sucking on Mitch’s penis was hard to swallow (please excuse the pun). 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 (again I don’t know who—to this day I can’t tell you who was doing what) come behind me and she (he? Oh, how I hoped not!) started licking my right ear and probing the canal with his or her tongue. At the same time two more sets of fingers began stroking the insides of both of my thighs. Then another tongue started exploring my other ear.

The feeling was exquisite, and to my chagrin I felt myself starting to become aroused. I heard a couple of stifled giggles, followed by a “shh” sound. 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 an inevitable hard-on. To make matters worse, I was pretty sure someone was taking a video of the extraordinary scene for posterity.

My situation was becoming bleaker by the second. I felt somebody’s tongue circling my nipples, and ever so slowly the tongue started working its way down my torso.

Meanwhile, somebody (please, not Mitch!) was using their fingers to gently caress my balls. There was no turning back for me now; I had a full-fledged hard-on. Again more stifled giggles. 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. Whomever 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 it as Becky’s) whispered loudly in my ear (someone else was still licking it, but I heard my sister’s demand), “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 people were still delving into my ears with their tongues, another mouth was kissing my chest and stomach, and someone (maybe the same person who was giving me head—maybe not) was tickling my balls with their fingers. The sensation was overpowering, and I was just about to explode.

My sister somehow sensed as much. “STOP!” yelled Becky. And they did. So did I, and I removed the dildo from my mouth, holding it at my side. I was left in a state of near-climax, which created a dichotomy. From a physical standpoint, it was sheer frustration. But on the other hand, to achieve reluctant orgasm at their hands (and mouths) would have certainly exacerbated my already humiliating state.


Another Measurement

“Time for a measurement!” stated Felicity while she retrieved the measuring tape from the top of the bar.

“Yes!” chimed in Cheryl, “Let’s see if Blondie has to finish the job in front of us or if he can do it in the privacy of his bedroom.” This elicited yet another chorus of laughter.

Everyone gathered around me in excited anticipation. 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 it 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 across the length of my shaft. I looked down for the tale of the tape, and my heart sank appreciably. “It’s only four and a half inches!” squealed Felicity, to everyone’s glee and amazement.

“You lose, Blondie,” sang Becky cheerily. “Now we get to see your grand performance. Do you think you can spurt some juice out of that little thing?”
Everyone laughed heartily. They were at an elevated level of excitement and enjoyment. Felicity rubbed her palms together and jumped up and down, grinning from ear to ear.


My Naked Performance

“Let’s see,” said Becky. “We should put you up on a platform.” She snatched a large beach towel from a shelf and draped it across the felt of the pool table. She patted the table and said, “Hop up here, sweetie pie, so we can all see you better.” I momentarily put my face in my hands, and then lifted my knee to climb onto the table. I tried handing Becky the dildo, but she would have none of it. “No-no-no, you need that. You've got poor Mitch all worked up. He must be in a state of sexual frenzy, waiting for you to make him cum.” Dismally, I climbed up onto the pool table.

“Blondie promised he would dance for me on my birthday,” proclaimed Felicity. “I think we should make Blondie dance for us while he makes himself spurt.” I winced noticeably.

“Oh, what a brilliant idea!” laughed Becky. “A naked dance on the pool table while sucking on Mitch and getting himself off. That should be quite the spectacle!” She walked briskly to the stereo to select the music. “Marcia, do get this on video. It will be some priceless footage.” She pulled a CD and queued it on the player. “Okay, big boy, it’s show time. This is your grand finale, so you’d better make it good.” She hit the start button and “I’m So Excited” by the Pointer Sisters began playing on the stereo. Becky jacked up the volume. I began to dance, though rather lethargically. My level of humiliation had never been higher.

“Faster, Blondie, faster!” screamed Julie. I picked up the pace somewhat, difficult as it was.

“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 simulated oral sex on the fake penis. “Suck faster, Blondie!” continued the relentless Brenda. “Mitch wants you, suck his dick!” I increased the tempo of the sucking motion, to everyone’s amusement.

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

My penis had shrunken about halfway since the group stimulation ended a few minutes earlier. It would be problematical for me to regain that level of excitement under the circumstances, but I had a pretty good feeling that my ordeal would not end until I managed to climax. I took my penis in my right hand and started playing with myself. Becky reached behind her and pulled a small brown container of suntan oil from a shelf and walked up to the pool table. “Hold out your right hand, Blondie!” she yelled over the music. When I did, she poured a fair amount of the oil into my palm. The fragrance of coconut permeated 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 increased. “You’re not dancing fast enough, Blondie. Faster!” screamed Becky.

I tried moving a little faster, but (naturally) my heart wasn’t in it. Words can’t do justice to the humiliation I felt at that time. I looked out at my tormentors and saw seven young ladies in a state of utter bliss. Mitch was standing behind the bar, which was shielding his activity. It was plain for me to see that he was in the midst of self-gratification. He looked at me lustfully. I quickly turned my head away in disgust.

“Dance, Blondie! Faster!” Julie pushed.

“All right, that does it,” I heard Becky say. She marched over to the far wall and pulled a canoe oar from its hook. 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 and the word “faster” were simultaneous. In two short seconds the searing pain reverberated throughout my body. 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 jumping up and down from the pain. The cheering and laughter were at its loudest point of the night. I moved at a frenetic pace, and the rhythm of the sucking and stroking motions naturally increased likewise. They were laughing hysterically now, seemingly in a frenzy.

I couldn’t help but glance at Mitch and could see that behind the bar he was pumping away in earnest. I couldn’t let that get to me; I had to cum. I was getting very close, and I was pumping away frantically. Becky turned the music up full blast. The Pointers were at a fever pitch.

“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 were screaming and laughing. I continued to pump away, at that point completely absorbed in my fulfillment.

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

The last drops of my fluid dribbled out, and I dropped to my hands and knees, totally spent from my orgasm and the hideous humiliation I had endured. Beads of sweat dripped from my forehead. The music quieted, and momentarily the girls did, too. Then a moan emanated from behind the bar. The girls turned back, and it was obvious that Mitch had just achieved sexual climax.

“Congratulations, Blondie, you did it—you got Mitch off!” blurted out my sister. To the sounds of laughter, she threw me a robe. As the merry group filed out, my sister had a parting shot. “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. Nothing fancy, you can come as you are.”

They disappeared into the night, their sounds of laughter gradually diminishing. I wrapped the robe around my shoulders and stared down blankly at my drying semen. The feeling of desolation was overpowering, and the suppressed tears began to flow. As my whimpers escalated to loud, uncontrollable sobs, my sense of hopelessness hit home, seemingly registering in my brain with a loud thud. I rued the day I enrolled in Roosevelt High, my personal house of horrors.


Epilogue

It's two weeks later, and I'm just now starting to come out of my doldrums. I did have to submit to them the next night. I'm not going to go into detail, but they forced me to watch the video with them. They made me strip naked again and I had to serve them cocktails and hors d’ oeuvres. They were having a high old time, and it was excruciating for me to relive the horrible affair all over again.

I don't know what the future holds, but one thing that keeps me going is hope. I don't know how I will go about it, but I'm working on coming up with a plan to exact revenge on each and every one of my tormentors. If I do, I will be sure to add to this story. What a great feeling that would be!

End
Hammer
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Re: Roosevelt Humiliations

Post by Hammer »

Have to ask will there be a story where the character of Blondie gets payback on his tormentors like Tommy in Tommy’s retribution?
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Re: Roosevelt Humiliations

Post by Blondie »

Hammer wrote: Sun Jan 28, 2024 4:40 pm Have to ask will there be a story where the character of Blondie gets payback on his tormentors like Tommy in Tommy’s retribution?
As of right now I don't have a story written where Blondie gets his revenge, but that doesn't mean it couldn't happen someday. Originally, when I wrote the epilogue to this story, I set up a scenario where Blondie indeed would get back at his tormentors. The scene would happen the very next night when the gang watched the video of Blondie's humiliations from the night before. While they were enjoying the festivities they were victimized by a couple of sadistic intruders, who brandished guns and forced the girls to strip. Blondie managed to hide in a closet, but opened the door a crack and captured it all on video. He would use the video as a threat and force his previous tormentors into compromising situations during the rest of their time at Roosevelt.

But I never posted it and changed the epilogue to what you see now, for two reasons: 1) As you will see in a future story ("The Felicity Chronicles: My Exploits as a Humiliator"), I wasn't done with Blondie's travails at Roosevelt High, and 2) I knew I wouldn't have time to write it up in the foreseeable future, and I didn't want to promise something I couldn't deliver.

There is a scenario where Blondie might get a chance to obtain retribution on Felicity. Without giving anything away, that potentiality presents itself in another story involving a boy named Andy (not the "Felicity Chronicles").
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Re: Roosevelt Humiliations

Post by Gomez »

Please keep writing these kind of stories, your a brilliant writer!
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Re: Roosevelt Humiliations

Post by Gomez »

I also wanted to add, your style of writing is great because you dont go over the top like many other stories I have read. You concentrate on the humiliation, and dont go down the pathway of dungeons etc. Thanks again.
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