Roosevelt Humiliations, Chapter 7
Posted: Fri Jan 12, 2024 2:54 am
Chapter 7: Brenda's Revenge
Payback
Well, unfortunately I have another humiliation to recount. It took place on the penultimate day of my sophomore year at the hands of Brenda, my new nemesis, with the help of some of her friends.
As you may recall, I left you with Brenda, who is in my homeroom, leaving on my desk my underwear that she had kept during my staggering humiliation in the auditorium. It is quite apparent that she has a wicked streak, as since then she has taken great pleasure in teasing me about my most mortifying experience in the auditorium. It had gotten to the point that all she had to do was run her eyes up and down my body, figuratively undressing me, followed by a knowing grin. Invariably I would turn bright red, furthering her enjoyment.
After suffering a few of those embarrassing encounters with Brenda, I decided to exact some revenge. The payback was sweet while it lasted, but I’m sorry to say that ultimately, I paid the price—dearly—for this decision.
There were three days left in the school year when I acted out my plan. You see, Brenda happens to have very small breasts, which I had hoped she would be very self-conscious about. I thought it would be an excellent idea to exploit this probable source of embarrassment.
I purposefully arrived at school early that day, and, as planned, I was the first one in my homeroom class. I went to the chalkboard and wrote in large letters, “BRENDA HOLLISTER HAS TINY LITTLE TITTIES.” Full of myself over this slight but effective (I hoped) little scheme, I smiled, brushed my palms together back and forth a few times, and left the room. To avoid suspicion, I waited outside in the hallway for Brenda to arrive, so we could walk in together.
“Hi, Blondie,” she said when she spotted me. In her playful way, she looked down at my crotch, then back at my face and grinned. Satisfied with my inevitable blush, she giggled to herself, turned and entered the room. I followed her in, anxiously anticipating the next few moments.
There were about twenty or so students already in their seats, and they all giggled when Brenda entered the room. I kept a close eye on her as she sat down with a quizzical look on her face. It was only a matter of seconds before her gaze steered to the blackboard.
It was a precious moment for me as I reveled in her reaction. At first there was a look of shock before she started blushing. Then she jumped out of her chair and quickly marched to the blackboard, where she erased the offensive text. When she turned around, to my delight her face was a bright cherry red.
Plus, she was wearing a tight white sweater, and one could just make out the little nubs protruding from her chest. Certainly, she had to know that at that moment everyone was staring at her small breasts. Now extremely self-conscious, she folded her arms across her chest as she made her way back to her seat.
I looked back one more time a couple of minutes later and was quite pleased to see that the blush on her face was still evident. At that moment, although her humiliation paled in comparison to what I went through in the auditorium, I felt a wonderful sense of vindication.
A Reversal of Fortune
That would have been a great way to finish off the year, but to my utter regret I made the mistake of getting greedy. I wanted to relive that experience, so on the last day I again arrived early to school. I had just written the words “BRENDA HOLLISTER HAS” on the board when I was startled to hear Brenda’s voice. “You little shit!” she exclaimed. “I had a hunch it might be you, but I didn’t think you had it in you. Well, you’re about to pay, Blondie. Big time. Shaken, I watched her reach into her purse and pull out a roll of bright orange yarn. “Drop your pants,” she ordered.
“I…I can’t do that here. Somebody might come in,” I responded anxiously.
Brenda was undeterred. “I don’t think you want me to get Mitch and Reggie involved here, now Blondie, do you?” Oh yes, the “stripped on Main Street” threat again. I swear, next time I might take my chances and call their bluff.
No, I know better.
I unbuckled my belt and unbuttoned and lowered my trousers slightly, exposing my underpants. Brenda smiled and took the tops of my jeans in each of her hands and swiftly hauled them down to my ankles. I watched as she took a pair of scissors and cut a length of about twenty feet from the yarn. “Get those undies down too,” she directed.
I stood transfixed, unwilling (or, more accurately, “unable”) to do her bidding. “Please, Brenda, don’t do this to me!” I pleaded.
“Ah, the hell with it,” she said. She simply used the scissors to cut my underpants off and let them fall to the floor, where I felt them graze me feet. While I instinctively covered my crotch with my hands Brenda, smiling with enjoyment, picked up my severed underpants and walked back to my seat, where she laid them on the desk.
Once again, thanks to Brenda, there was the unusual sight of a pair of underpants on my desk. I looked around nervously as Brenda came back to me, the length of yarn in her hand. “Hands on your head,” she commanded. Resignedly I raised my hands to my head, exposing myself to my tormentor. “Well, well, little boy, I see you’re still bald as a cucumber,” she teased. “And look how tiny you are! Such a cute wittle boy,” she taunted while taking my penis between her thumb and index finger and tweaking it back and forth. Startled, I flinched and retracted my hips involuntarily. Brenda giggled at my reaction. “What’s the matter, little boy? Are you embarrassed about your hairless little wee wee?”
Yes, it was oh, so true. I still was completely hairless down there, which was a condition that caused me considerable angst. And having my small, hairless penis on display at this girl’s whim caused me extreme embarrassment.
My embarrassment and apprehension increased as Brenda took the yarn and wrapped one end around my penis and balls, tying a snug knot at the base of my penis. “Okay, you can get dressed now, my little hairless one,” she declared.
Red-faced, I hastily donned my jeans and buttoned them back up. But they didn’t stay buttoned for long as the devilish Brenda immediately started unbuttoning my fly. I retracted my hips, but she reached into the opening and felt around for the yarn (her prying fingers causing me to flinch noticeably) and pulled the yarn through the opening before slowly buttoning my fly back up. She had a smile on her face while she performed the task. I must say it was quite humiliating having her fumbling around so close to my penis like she owned it.
She then took the roll of yarn and cut another short length and used it to tie my hands behind my back. It was soon apparent to me what wicked mischief she had up her sleeve.
The Obedient Puppy
“Let’s go for a walk, Blondie,” she said as she pulled on the length of yarn dangling from my fly and walked toward the door.
“Oh God, no, Brenda, please!” I implored.
But it was no use, as the grinning Brenda, without a word, continued on her way, tugging me behind her. She pulled me out the door and marched me through the hallway, much to the amusement of the bystanders. As word of my plight spread, the interest and noise level in the hallway escalated significantly. My face felt like it was on fire as I followed Brenda like an obedient puppy through the full length of the hallway while the students cheered and laughed at the bizarre spectacle.
Courtyard Humiliation
She then led me out to the main courtyard, where I was greeted with a similar response. There Brenda caught up with three of her friends, Joanna, Marcia, and Cheryl, who were standing and chatting next to the Roosevelt statue when their mundane morning suddenly became quite stimulating. As you know, I’ve had at least one humiliating experience with each of these girls, so they were predictably gleeful as they appraised my condition.
“Brenda, Brenda, what have we here?” asked Joanna, with relish in her voice.
“Oh, I’m just teaching Blondie here a little lesson,” answered Brenda. “Can you believe this little shit was the one who wrote on the blackboard about my tits?”
Brenda’s three friends laughed as she jerked on the yarn, forcing me to awkwardly jump forward a couple of steps. Marcia, giggling freely, took the yarn from Brenda’s hand and merrily started trotting around the courtyard. Powerless, I was forced to follow her. There were at least two dozen other people in the area, and their laughter resonated throughout the courtyard as they enjoyed the comical sight.
Marcia stopped next to her friends and draped her end of the yarn over the outstretched arm of the Roosevelt statue. She then pulled on the end of the yarn, drawing me forward and upwards, to a point where I was forced to stand on my tiptoes, as I felt the upward tug on my genitals. By now the four girls were really enjoying themselves, along with the rest of the spectators. Marcia held me in that position while the girls chatted among themselves.
I was physically and emotionally quite distressed. My distress level intensified when their topic of conversation turned to back to me.
Teased and Tormented
“So, Brenda,” asked Marcia while fingering the yarn and looking at my crotch, “What exactly is this tied to? Is it tied around his balls or his little dick? From what I saw in the auditorium a few months ago you didn’t have much to work with.” I blushed brighter while the four girls giggled.
“Actually,” answered Brenda, “I managed to involve both his balls and his little dick. Would you like to see for yourselves?” Brenda moved in my direction. My eyes widened in shock at this latest turn of events.
“Oh yes, let’s see!” Of course, all three of them were in full agreement.
“No!” I yelped.
Brenda, smiling, pulled my tee shirt from my jeans. She lifted it all the way up my chest and pulled it off my head. With two hands she tugged it downwards behind my back and scrunched it up at the small of my back, just above my tied wrists. I shivered involuntarily at the exposure. “Excellent, my little hairless one,” she smiled while rubbing the palm of her hand back and forth across my bare chest. She reached to my midsection and unbuckled my belt. She talked to me as she went about her task. “What do you say we pull your pants down so they all can see what a little boy you look like down there,” she teased mercilessly.
“No, Brenda! No! Please!” I begged frantically. I looked around the courtyard and everyone was looking at the two of us in fascination. She ignored me and addressed the girls while she slowly, deliberately went about her task of unbuttoning the four buttons.
“This will be pretty easy, because he’s not wearing any underpants,” she announced to the crowd while undoing the first button. A couple of gleeful shouts rang out. The grins broadened. She could sense that she had everyone’s attention and she spoke a little louder. “You see, I took some scissors and snipped off his little tighty-whities when he refused to take them down for me like I asked him to,” she stated rather matter-of-factly. The second button was undone now. She was playing the crowd, much to my wretchedness. “Can you believe his impertinence?” The third button was undone. My breathing quickened. “Now his little wee wee will be put on display for all of us.”
Laughter and cheering reverberated throughout the courtyard. She unbuttoned the final button. I clenched my eyes shut, bracing myself for the next humiliation. Brenda held onto the tops of my trousers, holding the fly closed. Of course, this would be a temporary situation. She looked up at me. She was grinning sadistically. “Are you ready, big boy?” she teased.
“Please…Brenda, I’m begging you…don’t do it!” I pleaded anxiously.
“Oh, come on, sweetie, you don’t mean that. Look how much fun everybody is having. They can’t wait to see what you've got down there.” She paused, looked me in the eyes and smiled. “Boy, they’re in for a good laugh, aren’t they, Blondie boy?” She stepped behind me. Her arms were around my waist, holding my pants up. She put her mouth directly to my right ear. “Prepare yourself, my little hairless one,” she taunted, tickling my ear in the process. “In a few moments, I’m not just going to give everyone a quick little peek. I’m going to pull your pants aaaaaall the way down. And if the mood strikes me, I might just take them completely off!”
“Oh, God!” I squealed. My anxiety was mounting, and I swear I could hear my heart pounding on my sternum.
Brenda was relentless with her psychological torture. “Just think, your tiny little hairless bits are about to be exposed for all these people out here.” She paused for effect. “They’ll all be staring and laughing at you, and you’ll be squirming around, totally helpless to do a thing about it.”
“No! Brenda! No! Please!”
“Oh, yes, Blondie boy. This is going to be a moment you’ll remember for the rest of your life.” She paused. “And so will all these people out here. Every time any of them sees you, they’re going to think, ‘There’s the guy who was stripped and humiliated by a girl in the courtyard.’ ” Brenda giggled and continued. “And they’ll always have the picture in their head of your teensy, hairless weenie bobbing about while you wiggle around helplessly.”
I was frantic now, as it sunk in that she was absolutely right in that assessment. She took notice of my look of horror. “Ah, you know it’s true, don’t you, Blondie? Can’t you just picture the look on everybody’s face in just a few seconds when I pull your pants down? For all intents and purposes, you’ll be naked. And ohhhh, so naked you will look, with no hair on your body. I mean, think about it. You’re out here in broad daylight, and your tiny, hairless, little-boy penis will be on display for all these girls that you’ll have to face for the rest of your days at Roosevelt High. Every time they see you, either in the hallway or maybe in the same class, they'll picture you naked. It'll almost be like you're reliving this all over again.
"When I take these down, it should be quite comical, because you’ll be squirming around in your absolute embarrassment, and your little pee pee will be jiggling around…oh, my, it will be quite the spectacle, don’t you think so?”
The Unveiling
She pulled her mouth away from my ear. “Here we go, folks,” she called out. “Is everybody ready?” A resounding affirmative emanated from the entertained students. Brenda stepped back slightly. I sensed my doom but cried out anyway in desperation.
“No! No!”
“Wheeeeee!” she yelled gleefully while sliding my pants all the way down to my ankles in one steady motion. The roar of laughter in the courtyard was riotous. I writhed and twisted my body frantically, but there was nowhere to hide.
“Look at that teeny little thing!” laughed one of the girls. “It’s like a little clitty!” she exclaimed, drawing uproarious laughter from the crowd.
“And he has no hair!” squealed another.
“Oh, this is too much!”
Mortified to the max, I tried lifting each leg up one at a time in a frenzied attempt at covering up. I soon abandoned that effort when I realized I was succeeding only in the process of possibly displacing my pants altogether. I was forced to just stand there and squirm helplessly, just as Brenda predicted, enduring the laughter and ridicule of the thoroughly entertained audience.
Paraded to Homeroom
Mercifully, the warning bell went off, and the crowd began to disperse. Marcia let go of the yarn, and Brenda buttoned and buckled me up, making sure the yarn stuck out from my fly. I was relieved that she didn’t make good on her threat to take my pants completely off. But, to my dismay, she chose to leave me naked from the waste up.
“Okay girls, it’s time to take my little doggy to back homeroom,” laughed Brenda as she took the yarn and started leading me towards the building.
“Thanks for the entertainment, Blondie dearest. Let’s do it again soon!” chortled Marcia, amongst laughter from her friends.
The giggling continued as I was forced to experience the same degradation as before while Brenda tugged me the length of the hallway. My humiliation was exacerbated somewhat since I wasn't wearing my shirt.
We entered the confines of my homeroom, which by now was nearly full of students. Miss Farnsworth hadn’t yet arrived, so Brenda, thriving on the attention and delight of the other students, paraded me back and forth a couple of times in the front of the room, much to everyone’s amusement. When we reached my desk, she untied my hands. “Okay, you can put your shirt back on and tuck your leash in your pants now, my little pet. Oh, and one more thing, before you sit down…” Brenda then whispered her instructions in my ear. I winced as she turned and strutted to her seat.
As I donned my shirt and tucked the yarn back in my fly, I made my way to the chalkboard. I hesitated, closed my eyes, then very reluctantly picked up the chalk and wrote on the board in very large letters, “BLONDIE HAS A TEENSY WEENSY HAIRLESS LITTLE PEE-PEE.”
Hysterical laughter filled the room. I’m sure it was poetic justice for Brenda as I turned and walked briskly back to my seat, staring at the floor while blushing crimson. My sheared underpants were still on the desk, and I quickly wadded them up and tucked them away, an experience I was becoming all too familiar with.
I couldn’t bear to look back, but I’m sure Brenda was basking in the moment, grinning from ear to ear.