The Felicity Chronicles: My Exploits as a Humiliator

Stories about boys ending up in compromising situations, preferably naked and embarrassed, as the name suggests.
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The Felicity Chronicles: My Exploits as a Humiliator, Chapter 5

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Chapter 5: Blondie: My First Experience in Humiliation, Part 3 of 4

I’ll get back to my escapades with Johnny Boy soon, but for now, let’s rewind to Blondie’s account of my thirteenth birthday. This is the part where I had him all to myself in Becky’s bedroom—an experience I’m quite sure neither of us will ever forget.

The next hour would prove to be nearly unbearable.

Ah, yes—that would be the hour when I had Blondie all to myself in the bedroom. I remember feeling very titillated in anticipation.

With extreme apprehension over what lay in store for me, I sat on the bed. My feet dangled above the carpet, making it easier for her to kneel and begin with my shoes.
“Isn’t this great, Blondie?” she said while fiddling with the buckles. “Just the two of us? It’ll really give us a chance to get to know each other, don’t you think?”


It amused me, speaking to him like we were just casually getting acquainted—like we were on a date, even—when we both knew he was about to be dragged deeper into the depths of his humiliation. I was dead set on engaging him, even though he clearly wanted no part of it.

I remained silent. The last thing I felt like doing during this godawful experience was engaging in conversation with this fiend. But she had other ideas. She stood up and pointed her index finger at my face. “Now listen, Blondie, when I speak to you I expect the courtesy of a response. In case you haven’t noticed, there are two of us in this room, and I don’t plan on carrying on a monologue.”
“Do you understand me?”


Similar to a mother talking to her child. Being three years his junior, I really delighted in playing the authority figure.

She kneeled back down and went to work on the shoes and socks. She picked up right where she left off. “So, tell me a little bit about yourself.” Both shoes were off now, and she deliberately began rolling one of the anklets down my foot.

He's right, I pulled his sock down very deliberately. I was having such a great time, and I wanted to draw out his stripping as long as I could. Great for me, miserable for him. A win/win.

She pulled the dress completely off and left me standing there in the petticoat, face burning. She stepped in front of me and gazed at me, grinning widely. “How delightful. You really do blush like a little girl.”

I really enjoyed looking him up and down right there, with him knowing I was ogling him. He saw me grinning at him and he squirmed under my gaze, while his cheeks flushed deliciously—it was just enchanting.

Putting both hands on my shoulders, she eased the straps of the petticoat down my biceps, starting its leisurely descent. “Tell me about your experience with my sister in her store at the mall. I heard such delicious things.”
“W-what do you want to know?” I was stalling. I really didn’t want to relive that humiliation, especially under those circumstances.
“Everything,” she answered fervently.


How cool is that? While getting methodically stripped—out of girl's clothes, no less—I made him recount one of the most humiliating experiences he's ever gone through. I delighted in his downcast eyes and his blushing cheeks as he forced himself to relive the experience.

The petticoat was now at my waist, leaving me bare-chested. Felicity kneeled to continue with matters at hand. I looked down to see the garment being pulled further down, exposing the frilly panties. Felicity had an impassioned look on her face. She looked like she was having the time of her young life.

He is so right. I was getting more and more charged up by the second.

As Felicity stood up, she prodded me on. “Go ahead, you tried on a bra and...?” She tossed the petticoat on the bed and stood back and grinned wickedly at me.

Grinned wickedly. I just love that. And I'm glad he noticed.

He had a lot of trouble saying the word "panties." It was adorable. When he did, I just loved it. The word sounded so delicious coming from him.


“Go like this.” She made two fists and put both hands on her hips, elbows pointing to the sides. I struck the pose. She walked around me slowly, drinking it all in. “Oh my. Look at you. Just adorable. But...” She trailed a finger down my tummy, stopping at the waistband. “...these are going to have to come off, so you can model your next outfit.”
She reached for the waistband of the panties, studying me intently. She got the reaction she wished for as I involuntarily retracted my hips, eliciting a knowing smile from her lips.


I wasn't sure how he would react when I went for the panties. I mean, he was certainly embarrassed to be wearing a pair of ruffled panties. But when he retracted his hips like that, he confirmed that it was better than the alternative. He really didn't want me to see him naked, which made the foreplay ever more exciting.

“Hmm, how shall we do this? Shall I take them down, or would you like to do it yourself?”

I was just messing around there. I really wanted to do the deed myself, and I wasn't going to let him deprive me of that pleasure, no matter what he answered. But I was pretty sure he didn't have the guts to take them down right then and there.

“What’s the big deal? I’ve already looked down your panties and saw your little thingy, remember? I told you it looked just like my little brother Joey’s, except you have hair.” I was blushing crimson now, and she went in for the kill. “And the more you blush, the more fun I have."

I was teasing him there, but it really was true. That's one of the reasons Blondie is my favorite victim. I know exactly which buttons to push, and I can make him blush at will. It's so precious, and it never gets old for me. Every time I make him blush I feel a twinge of excitement all over. I really feel so fortunate that I have someone like him at my beck and call.

Felicity grasped the hem on each side with her fingers, and held them there, teasing me. She looked up expectantly. “It’s time, Blondie. It’s the moment we’ve been waiting for. Isn’t this fun?” I had no answer. “I’m doing all the talking now, Blondie, and I don’t appreciate it. Now, be a good boy and ask me nicely to take down your panties.”

One of my favorite humiliation techniques is to force my victim to beg for something that is the last thing on earth he or she wants to happen. They know it's going to happen regardless—then to make them beg for it just rubs salt in the wound.

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

His voice cracked in such a delectable way as he forced himself to say that, especially when he uttered the word "panties." Precious.

“Why certainly, sweetheart,” she replied with pleasure in her voice. “Would you kindly put your hands behind your head so I can do that for you?”

The hands behind the head position is, of course, a classic pose that I relish using on my naked victims. Blondie wouldn't be able to cover himself when I pulled down his panties, knowing there would be repercussions if he dared try. For me, it’s the ultimate show of power. Their vulnerability is enhanced, and it strengthens my superiority and their submissiveness. The vision of them standing helplessly naked before me in that pose is awe-inspiring.

I hesitated, then interlocked my fingers and raised my arms, exposed and completely vulnerable. My sense of dread was extreme. Felicity took a long, slow look at me, then smiled. She was ready to do the dirty deed. “Okay, here we go, are you ready? On three: One... two...” Then she stopped and stepped back.

I stepped back because I had an inspiration—one I really look forward to telling you about.
Last edited by Blondie on Sun May 10, 2026 5:24 am, edited 5 times in total.
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The Felicity Chronicles: My Exploits as a Humiliator, Chapter 6

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Chapter 6: Johnny Boy: Homeroom Humiliation

After taking my seat directly behind Johnny in homeroom, I didn't wait long to have some fun with my newest plaything. The daily announcements had barely begun droning over the intercom when I scribbled a little note, folded it, and inched my desk forward until it nearly touched his. There was a gap between his seat and the back of his chair, making it convenient for me to reach down and wedge the note between his tucked in tee shirt and the waistband of his jeans.

Johnny flinched at the unexpected touch, then gingerly reached back and extricated the note. I could almost feel the heat from his blush when he opened the note, which read:

What color are your underpants?

The back of his neck flamed red. He just sat there, clearly at a loss for how to respond. So I dashed off another note and slid it into the back of his jeans:

Please answer my question. Write it down and put it where I did.

Again Johnny pulled the paper from the back of his jeans and opened it up. This time, after a few moments of contemplation, he scribbled something and inserted it behind his back. Grinning at his compliance, I reached down and pulled it out:

Black

My next note was short and bold:

I'd like to see.

No reply. So naturally, I took matters into my own hands—literally. I leaned forward and started tugging his T-shirt out of his jeans. He instinctively reached back and pushed my hand away, but I wasn’t about to let that fly. I furiously wrote another note and shoved it down the back of his jeans with authority:

If you EVER touch me again without my permission then those pictures my sister and her friends took will be all over the school. I’m afraid I’ll have to punish you now, Johnny.

I let him mull that one over for a minute before delivering another note:

I'd like you to lift your shirt up and keep it pinned to the back of your chair.

Much to my delight, after a long pause he reached back and lifted his shirt. It was only his back, but I was a bit titillated to watch him expose his smooth skin at my behest. There was a cute little dimple on the small of his back that I found enchanting. And the control I now felt over him was seductive.

I slipped another note into place, setting it squarely over that dimple:

That's a good boy, Johnny. Now undo your belt and your jeans. Unzip them all the way—I want them nice and loose so I can examine your undies properly.

I knew he would have a problem with that, so while he was reading I gave him a quick follow-up note:

NOW!

I could tell by his retracting elbows that he was reaching for his belt. I grinned triumphantly. I wished I could see his face, but my vivid imagination told me what it looked like, and the image was delicious.

He furtively looked to both sides before carrying on. When he finished, I reached forward with both hands, yanked his jeans down to the seat, and—surprise, surprise—he was wearing tighty-whities. I almost burst out laughing.

I glanced to my left. The girl beside me was openly watching, eyes wide with amused curiosity. When our gazes met I winked at her, and her grin widened. I made a mental note to have a conversation with her—she struck me as someone who might prove useful in my endeavors as a humiliator.

It was time for another note. I slid my fingers under the waistband of Johnny’s briefs, pulling them out just enough to peek at the top of his crack. He tensed, but didn’t dare resist. I held it there for a few extra seconds, which served dual purposes: 1) It was a delectable display for me—and the girl on my left, no doubt, and 2) It had to be excruciating for Johnny, who probably was cringing with embarrassment.

My favorite part of that moment was when he took a nervous glance over his shoulder and realized the girl to my left was watching every second—and loving it. Before he turned away, I caught a perfect view of his profusely blushing face. It was awesome!

I shoved the note in as deep as I could, letting the waistband snap back. He flinched, and I giggled as he reached in, fumbling awkwardly to fish it out. The note read:

Was little Johnny too embarrassed to admit that he still wears his tighty-whities? You lied to me, Johnny Boy, and I'm very disappointed in you. I'm afraid you’ll have to be punished.

I quickly wrote another note and stuffed it in his underpants. Johnny obediently extracted it, undoubtedly dreading whatever I had in store for him. The note read:

I want you to lift up your bum. Don’t sit down until I tap your shoulder.

As Johnny hovered, I rifled through my backpack for a banana. I was going to have it for a snack later, but I had an idea for its usage that far outweighed any desire to keep it for myself. Besides, it was turning brown and would be a little on the mushy side for my tastes.

I swiftly peeled the banana and broke it off at the bottom. Grinning, I leaned forward, pulled out the elastic of Johnny's underpants and inserted the banana lengthwise, making sure it was wedged between his cheeks. I let the elastic snap back, tapped him on the shoulder, and sat back, savoring the view.

The girl on my left was trembling with silent laughter. We watched as Johnny slowly, gingerly lowered himself back onto his seat. I'm sure it doesn't take keen insight on the reader's part to picture the rearrangement of the newly added contents inside Johnny's underpants, or to imagine what it felt like for the poor boy. Let me put it this way: After his up close and personal encounter with the squishy substance, Johnny probably never looked at a banana in quite the same way from that day forward. (giggle)

The bell rang sharply. Johnny jumped, then cast a nervous glance over his shoulder at me, his eyes glancing downward at his rumpled jeans. I grinned, utterly delighted by his obedience. Without a word, I picked up my pen and calmly wrote one final note. When I held it out to him, he snatched it from my hand like his life depended on it. It read:

You can tidy up now, Johnny Boy. I'll be in touch. Love, Felicity

He hastily yanked up his jeans and buckled up, then shot up like a jack-in-the-box and fled the room.

“I guess he didn’t want to stick around and chit-chat,” the girl beside me said, wiping a tear of laughter from her cheek.

I turned to her, grinning. “I’m Felicity.”

“Andrea,” she replied, shaking my hand. She was tall and pretty, of Latin descent. “That was hilarious. How in the world did you get him to let you do that?” I told her about the blackmail photos. As I explained, Andrea’s eyes lit up. “Oh my gosh, I’m jealous! You’re going to have so much fun with John.”

"You know his name. Are you guys friends?" I asked.

She shrugged. “We went to the same middle school, but we weren’t friends or anything. I always thought he was cute, but he’s really shy. Never gave me the time of day.” She smirked. “But he definitely noticed me today when you had part of his cute little butt exposed and he looked back at me, all embarrassed. He was paying attention to me then," said Andrea with a giggle.

"I noticed. When he realized you were aware of his... of his condition (giggle)... his face was glowing like a red neon sign."

We both laughed. We were becoming fast friends, seemingly with a common bond. It was at that point that I made an important decision in my quest to be a humiliator. I know I had told Julie that I wanted to go solo whenever I got the chance to strip and humiliate Johnny for the first time. But the more I thought about it, the more I realized that his humiliation would be intensified with another witness—especially a female witness. And Andrea was taking more than a little interest in the situation.

As we stepped into the hallway and were about to part ways, I called out, “Wait.” She turned back, head tilted, eyes hopeful. “I still have a few things in mind for our friend Johnny,” I said with a mischievous grin. “Would you be interested in—”

“YES!” she blurted excitedly before I could finish.

I laughed. “Alrighty then. I’ll be in touch.”

We exchanged numbers before heading to class. I smiled with satisfaction—it had been a wonderful little session with Johnny Boy, and I might have just gained a promising new partner in humiliation.
Last edited by Blondie on Sun May 10, 2026 6:23 am, edited 4 times in total.
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The Felicity Chronicles: My Exploits as a Humiliator, Chapter 7

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Chapter 7: Blondie: My First Experience in Humiliation, Part 4 of 4

When I last left you with the Blondie saga on my thirteenth birthday, he was perched nervously on a stool, hands behind his head, clad in nothing but a pair of panties—a delicious image forever etched in my brain—slightly trembling in anticipation of being stripped naked. My anticipation probably matched his, though from the opposite side of the spectrum.

Here is more of Blondie's account from the Pantsing and Stripping Forums site, along with my own commentary:

“Well then... it would be really special if you could sing ‘Happy Birthday’ to me while your panties are coming down. Will you do that for me, Blondie?” I groaned inwardly, but I nodded resignedly. What else could I do?
"Oh, goodie!" she squealed while clapping her hands with delight and giving an excited little bounce. I felt like I was submitting to a ten-year-old girl.
She poised her fingers on the hems of the panties again, looking up like a kid at Christmas. “Whenever you’re ready, Blondie...”
There was no sense in delaying the inevitable. I closed my eyes tightly and began to sing.


Just think about it: Blondie was about to be stripped naked by a 13-year-old girl, he had to beg for it to happen, and now he had to sing to me for my pleasure. I really must give myself a little pat on the back for that brilliant inspiration.

And oh, that moment when I put my fingers inside the band of his panties, he flinched—just a little—but enough to send a delicious thrill through me. I loved the feel of his smooth, vulnerable skin under my fingertips, knowing I was about to unveil all of it... slowly, deliberately, until he was standing there completely naked, trembling with embarrassment. Just delicious.


♬“Happy birthday to you.”♬ I felt the panties begin their inexorable descent.
“Sing it slower!” she urged. She was really getting caught up in the moment.


I have to say that my heart was beating a mile a minute at that point. I could barely contain myself.

♬“Happy birthday to you.”♬ The panties were now slipping past my penis. Felicity giggled with delight. It was all I could do to keep my hands on my head.

I absolutely was giggling with delight when I slipped his panties down and first exposed his little penis, knowing that he knew I was staring at his shortcoming that undoubtedly caused him anxiety. Oh, and did I tell you that he was singing?

♬“Happy birthday, dear Felicity...”♬ The panties were at my knees, beyond the point of return. I opened my eyes to a squint and looked down at a girl who was nearly beside herself in youthful, jubilant ecstasy.
♬“Happy birthday to you.”♬ The panties pooled at my ankles. Felicity stepped back and fervently clapped her hands with glee.
“Bravo, Blondie! Bravo!” she squealed with delight.


I was so excited! It really was a spontaneous, genuine cheer. I think I was actually jumping up and down. I mean, I was looking at my first naked boy (my little brother doesn't count) standing there red-faced and mortified against his will, and all because of me. He had his fingers interlaced behind his head, blushing up a storm while standing at attention like a good little plaything, because he knew he had to obey me. So yes—of course I was excited!

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 stomach sank. My torture at the hands of this cruel little girl was going to carry on.


Yes, I enjoyed reading how he called me wicked and cruel. I mean, those are traits of a good humiliator, right? And his phrase "completely naked and at her mercy" really struck a pleasant chord for me. I think I'm really in my element when I have someone completely naked and at my mercy.

When I have someone naked and at my mercy—can you tell I enjoy saying that?—I do enjoy carrying on dialogue with them. As embarrassed as they are, with me teasing them and forcing them to engage in conversation with me, it really can ratchet up the humiliation. For example:


“Tell me about Mitch.” I flinched, which did not go unnoticed. She pounced on the moment. “I hear he’s into both girls and boys. Is that true?”

Another one of Blondie’s most adorable traits is that he absolutely cannot hide his emotions from me—no matter how hard he tries. His body language always betrays him. A tiny twitch, a quick glance, the slightest little flinch—like when I casually mentioned Mitch—never escapes my notice.

And of course, there’s that telltale blush of his. It strips him bare in a way nothing else can, broadcasting every ounce of his embarrassment.


“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, I don't...”
She leaned in. “You know it’s true, don’t you? That’s why he’s here tonight—just to see you, right?” She pointed at the babydoll nightie draped over a nearby chair. “Mitch is going to be so excited to see you in that, isn’t he, Blondie?”


Talking about Mitch made Blondie considerably uncomfortable. Mitch is openly bisexual, on the aggressive side, and didn't hide his interest in Blondie. Blondie is straight and not at all interested. Under the circumstances of Blondie's current state of submission, the potential humiliating consequences loomed large. And, of course, I had no problem exploiting that possibility.

Mitch will be very excited to see you in your sexy little babydoll.” She grinned at me, then glanced down at my legs. “It’ll really show off those pretty legs of yours.” She released one of my hands and ran her fingers slowly down my thigh. “Mm, so smooth. He’s going to love your silky, slender legs. Don’t you think so, Blondie?”
“Oh God, please, no...”


I must say I really did enjoy caressing his smooth skin. And it was plain for me to see that he was quite self-conscious about his smooth, hairless legs. I found them quite fetching, and his self-consciousness only added to my stimulation.

She kept stroking, trailing her fingers up toward my hip. “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 arm and gave it the same treatment, sliding her fingers up and down. “And such smooth, girlie arms. Pretty, pretty,” she teased, dragging out the t sound with a musical taunt. I fidgeted under her touch, feeling increasingly more uncomfortable. Then she lifted my arm high, zeroing in on my hairless armpit. “And your underarms are nice and smooth, too. How lovely.” She lowered my arm and looked me straight in the eye. “Tell me how’d you got so pretty, Blondie.”
“B-Becky and Brenda did it to me,” I muttered.


Ah, I finally got the story of why he was so hairless. I only wished I could have been at the scene to lend a hand. Imagining that scene really excites me.

“Oh, and what a wonderful job they did!” she said.
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, just stared straight ahead, praying she’d move on. But of course, she didn’t. “Shall we get rid of it now?”
“NO!” I cried, my eyes widening in horror. That was probably a critical mistake. Her smile stretched slowly across her face. She’d struck a nerve, and she knew it. She left it alone for the moment, but I had a haunting feeling it was something she would revisit.


Very, perceptive, Blondie. (giggle)

Her gaze flicked back down, and her grin turned impish. “Don’t you think you’re a little small down there for a sixteen-year-old?” I fidgeted 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 wee-wee 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—and it was getting more humiliating each time.

That's an easy tactic for me, and one I always enjoy and utilize whenever I can. If the boy has an undersized penis like Blondie's, you know he is embarrassed about it. When I focused on it and teased him about it while trying to draw him into the conversation, he got all flustered and was blushing ever so adorably. Naked and blushing. It just doesn't get any better than that.

“Have you ever measured yourself down there? It can’t be more than a couple of inches.”
“No... please.” I was staring off to the side at the floor, unable to make eye contact with the little devil.
“Look at me, Blondie.” I hesitated, then forced myself to meet her gaze. Her eyes were dancing with delight. “Aren’t you embarrassed to show the other boys your little wee-wee?”
“I don’t know... please, can we talk about something else?”


I was ready to talk about something else. And he wasn't going to like it.

She smiled. “Okay. Tell me the story about the auditorium.”

The reader might remember the scene I'm referring to that Julie told me about, probably my favorite scene of something I wasn't involved in. It was when Blondie was fourteen, and Julie's friend Marcia (along with Mitch) made him do a slow strip in the dark auditorium during the school play. They got him completely nude, and he had to be in a panic, wondering if he would get his clothes back before the lights came on. He was essentially molested by Mitch and Marcia with the whole (unknowing) student body surrounding him. I have gotten myself off fantasizing about that scene on more than one occasion, so making Blondie talk about it was quite stimulating.

“You mean you were naked among all those people in the auditorium?”
I nodded, my eyes locked on the bedspread. “But... it was dark,” I offered weakly.
“I heard something about a flashlight. Did Marcia really make you shine a flashlight on your little pee-pee?”


What a creative idea that was on Marcia's part to use the flashlight. Then to make him hold it and focus it on his little weenie? That was a stroke of genius!

“Yes,” I whispered.
“Ooh, I wish I could have been there—it sounds delicious! Weren’t you just freaking out?”
“It w-wasn’t fun,” I muttered. "Please, you know the story.”
“The story goes that you didn’t have any hair down there back then. Is that true, Blondie, was the light shining on your hairless little wee-wee?”
I felt my face flush hotter. “I don’t remember,” I lied (it was true).


Once again, the mention of hairlessness embarrassed him to no end. I was ready to go in for the kill.

She pointed between my legs. “Shall we remove that unsightly hair before we go out there, sweetie?”
My eyes snapped wide again. “Please, no...” I begged.
“Ah,” she sang. “I touched a nerve again, didn’t I? Well, you know, I don’t have any hair on my privates, so it’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.


I thought it would intensify his humiliation if he knew that he was being controlled by someone who hadn't yet reached puberty. And his pubic hair, which was the only remaining evidence of his own emergence of adolescence—the size of his genitals certainly didn't qualify (giggle)—was being severely threatened. His apprehensiveness was increasing ever so deliciously.

“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 beyond her years.


Thanks for the compliment, Blondie. You were getting to know me quite well. :lol:

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.”

Of course, his pleas were to go unheeded. No way was I letting that opportunity pass me by.

* * * * *

I’ll try to get around to telling you about that wonderful experience, but I’m anxious to fill you in on how we humiliated Johnny Boy near his favorite tree. Please stay tuned—I’ll write that up for you as soon as I can.
Last edited by Blondie on Sun Oct 12, 2025 10:44 pm, edited 3 times in total.
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The Felicity Chronicles: My Exploits as a Humiliator, Chapter 8

Post by Blondie »

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Chapter 8: Johnny Boy: Stripped to Underpants

On the same morning that I humiliated Johnny Boy in homeroom, Andrea texted me between second and third periods. She wanted to meet up at lunch to talk about something. We settled on a table in the cafeteria near the windows.

Andrea jabbed at her salad with her fork and said, "I hope you don't mind, but I mentioned our little arrangement to a good friend of mine."

I shrugged, unbothered. "Oh, no worries."

She grinned, reassured. "Great, I didn’t think you’d care. Her name’s Natalie. She knows John—er, Johnny—from middle school. Anyway, I wanted to ask—would it be cool if she joined us when we, you know, do whatever it is we’re going to do to Johnny?"

I didn't have to think long about her request. Just like adding Andrea into the equation, another person involved would likely add to Johnny's humiliation. "Sure, I don't see why not," I answered.

Andrea’s eyes lit up. "Awesome. Natalie will be so excited. And she might be a great addition, because she thinks Johnny had a little crush on her. She says he used to stare at her sometimes in class. She actually tried talking to him a couple times, but he just locked up."

"Well, maybe we can loosen him up a bit. Or at least loosen up his pants," I replied, and we both cracked up.

As if on cue, Andrea’s gaze shot up and she waved someone over. "Hey, Natalie! Over here!"

I immediately understood Johnny’s fascination. She was a very attractive brunette—almost stunning in her beauty. She was tall—well, I guess almost everyone seemed tall next to me—with an athletic build and well-toned muscles. I remember thinking that if Johnny ever required physical restraint that she would be the one for the job.

"Natalie, this is Felicity," Andrea introduced.

Natalie took my hand with a firm, warm grip. "Nice to meet you, Natalie. Have a seat. We were just talking about you." Natalie looked at Andrea, then back at me hopefully. "Andrea tells me you want in on our little fun with Johnny," I continued.

Natalie smiled. "If it’s alright with you, absolutely. When Andrea told me what you did to him in homeroom... well, let's just say I was very sorry I missed that."

I grinned. "It was quite entertaining." I paused momentarily. "Sure, I'd love to have you aboard. All I ask is I get to call the shots. Feel free to jump in and help, but just follow my lead."

Andrea nodded eagerly. "Absolutely. I've seen you in action, and you certainly know how to embarrass a boy." The three of us laughed.

"No worries," chimed in Natalie. "From what Andrea described, we'll have a lot of fun following your lead."

"Great," I said. With our mischievous little trio now assembled, I glanced at the clock. "Hey, we still have a few minutes before the bell goes off. I know where Johnny usually hangs out. Should we go say hello?"

Andrea grinned. "Sounds like a plan!" and the three of us sprung from our seats and headed outside.

I was quite pleased—and somewhat surprised, considering what happened to him there recently—to see Johnny in his usual spot beneath the old elm tree, sitting with his back against the bark. He wasn’t alone. I took note of the friend, who was quite handsome.

"Hmm, I might have to keep this boy in mind for future use," I remember thinking.

Johnny saw us coming, and he jumped up as if to bolt.

"Stop, Johnny Boy!" I called. "I want to talk to you." Reluctantly, he stopped in his tracks. His friend, still seated, watched us with wary curiosity. We formed a loose half-circle around Johnny, boxing him in. "This is Andrea and Natalie," I said. He looked at them uneasily. "I understand you might be familiar with them."

"Hi, Johnny, I recognize you from middle school," said Andrea as she stuck out her hand. "And now we're in the same homeroom," she said, smiling.
Johnny’s handshake was limp, and he kept his gaze glued to the grass. I'm sure his eye contact with the grinning Andrea in the morning's humiliating homeroom scene was all too fresh on his mind.

Natalie chimed in. "Hey Johnny. Good to see you again." She shook his hand as well, and he flinched just slightly.

I turned to Johnny’s companion. "Are you going to introduce your blond-haired friend?" I asked.

"Please," Johnny finally spoke. "Leave him alone."

"My, aren't you the protective one," I said. "I have to say, that’s admirable." Then I fixed my eyes on the other boy and extended my hand.

"I'm Felicity."

He stood up, hesitating. "Robert," he said, shaking my hand warily.

"Hi, Robert. Mind if I call you Bobby?"

He shook his head firmly. "No, I like Robert." There was an edge in his voice, a subtle warning that he wouldn’t be as easy to push around.

"Okay, Bobby. I see you're a feisty one. I like that," I said. "More fun that way if I decide to play with you, too."

I turned my attention back to Johnny. "You know, girls," I said while reaching for Johnny's belt. "Johnny lied to me this morning. He told me he was wearing black underpants, when in fact..." Johnny slapped my hand away in a panic. I locked eyes with him. "Johnny, Johnny, Johnny. Didn’t I tell you this morning not to touch me without permission? You just earned yourself a more severe punishment. Now be a good boy and keep your hands to yourself," I said, returning to his belt.

"Leave him alone!" Robert said, stepping forward. But Natalie was quicker than lightning. In an instant, she had Robert’s arms pinned behind his back.

"Ow! Okay, okay!" Robert yelped, struggling in vain.

Natalie didn’t loosen her grip. "I’ll let you go if you promise to stand there and keep your mouth shut," she said, twisting his arm just enough to make her point.

"Okay! Okay! I promise!" he gasped.

"Good boy," she said, finally letting him go.

I gave Natalie a nod. "Thank you, Natalie." I shot Robert a stern look. "Bobby, you really shouldn’t have done that—you’ll regret it, trust me." Then, turning back to Johnny, I said, "Now, where was I before that rude interruption? Oh right, Johnny’s underpants," I said, unfastening his belt this time without resistance. I was free to have my way with him, and I felt myself shuddering with anticipation.

"Andrea, could you do me a favor and take off Johnny's shoes while I deal with these jeans?" I asked.

Andrea, grinning, didn't have to be asked twice. "I'm on it," she said, kneeling to untie Johnny’s shoes.

"Might as well get his socks while you're down there," I instructed.

"I was thinking the same thing," Andrea giggled, making quick work of it. In mere seconds, Johnny stood barefoot, his toes curling nervously in the grass.

"Thank you, Andrea. Natalie, can you take off his shirt? We don't have much time, and I’ll need both hands for his jeans. Oh, and keep an eye on Bobby—I’ll want a word with him after."

Natalie smirked at Robert, then turned her attention to Johnny, ready to act. "Don’t worry, Felicity. Bobby’s not going anywhere unless he wants a broken arm."

I looked up at the beleaguered Johnny and smiled at his wretched expression. "Arms up high, Johnny Boy, so Natalie can get your shirt off."

Johnny hesitated, then slowly raised his hands over his head. His compliance was intoxicating. I took a step back and soaked up the delicious scene unfolding in front of me, as Natalie slowly but steadily lifted poor Johnny's shirt up and off, drawing out the moment. It was quite titillating to watch the gradual reveal of his smooth skin. Most enticing of all was the moment his underarms were exposed—perfectly bare (as I had hoped!), smooth as silk and completely free of hair.

"Perfect, thank you, Natalie." I noticed Johnny’s instinct to lower his arms and corrected him instantly.

"Hands behind your head, Johnny Boy. I really like looking at your smooth underarms." Johnny was blushing deeply now, much to my delight. He glanced around nervously, noticing the small audience gathering at a distance. I wasn't concerned about getting in trouble. Though I wouldn't call it common, Roosevelt High did have a reputation for this sort of thing—I know Blondie was a frequent victim before I got here—and intervention from the teachers was rare, if not non-existent. Lucky me!

I returned my focus to his jeans, popping the button and lowering his zipper. "Now, as I was saying," I continued, "Johnny claimed he was wearing black underwear." I looked up at him. "Would you like to try that again, Johnny? What color are your underpants?"

"They're... they're white. Please don’t—"

"They're tighty-whities, aren't they, Johnny?" I interrupted.

"Y-Yes. Please..."

"Say, 'I'm wearing my favorite little tighty-whities today.'" I just love forcing my victims to say embarrassing things.

"I-I'm wearing my... my favorite... little tighty-whities today," he said. His voice cracked, and he appeared to be doing all he could to keep from crying.

"Yes you are!" I said cheerfully, yanking his jeans down to his ankles. Oh, how exhilarating it was to lay eyes on the small protrusion in his little underpants and his pale, hairless legs. And it was so delectable to hear him yelp, which was barely discernible above the laughter from the girls.

There was no resistance as I lifted his legs one at a time and pulled off his jeans. I stepped back to admire the full display—Johnny, hands on his head, crimson-faced, shivering in his underpants. I had orchestrated the public stripping of a boy, and I found myself giggling with glee—not only because of the deliciously embarrassing display before me, but because I realized, in that instant, that my calling as a humiliator had come to fruition.

I stepped close, tracing my fingers along his sides, loving the feel of his soft, smooth skin. I let my hands rest at the waistband of his underpants. He trembled, breathing rapidly. My level of stimulation at that moment was intense. I slid my fingers inside, and he flinched deliciously. I looked him dead in the eye.

"You know I could strip you naked right now if I wanted to, don't you, Johnny Boy."

His eyes went wide. "No! Please don’t!"

"Don’t what, Johnny?"

"Don’t strip me naked!" His voice was high, frantic.

The desperation in his voice was exquisite. It was a rush to hear him plead, and to hear him utter the word "naked," especially since he was referring to his own potential nakedness.

"That would be really embarrassing, wouldn't it, Johnny Boy," I cooed. "To be totally naked out here in the middle of the schoolyard. Everyone staring at your pee-pee."

He whimpered, "No! Oh, please!"

I glanced down at the front of his underpants, then back up at him. "And judging from the looks of things, there wouldn’t be much to see, would there, Johnny Boy?"

He shook his head, barely whispering, "Please... stop..."

With one hand I stroked his backside, while the other caressed his inner thigh. His breathing became heavier, and his whole body tensed. His balls were right there, and I couldn't resist. I stroked his scrotum ever so delicately. The smoothness of his skin was just delectable. He squealed, a sound sharp with humiliation. I leaned in close. "You know what's really awesome, Johnny Boy?" I said while continuing to tickle his little balls. "I can play with you like this any time I want." He didn't answer, so I pressed. "Right, Johnny Boy?"

"Y-yes," he said softly in a high-pitched voice.

I smiled. "That’s my good Johnny Boy." I continued to torment him with my fingers for a few more seconds. After a final caress, I withdrew my hands and planted a kiss on his burning cheek. "Thank you, Johnny Boy. That was beautiful."

Of course, I could have stripped Johnny naked right then and there—honestly, the temptation was nearly overwhelming—but just like with Blondie that wonderful night, I decided it was more fun to tantalize him, and to save that pleasure for another time. And there was no question that there would be another time.

I turned to Robert. "You also need to be punished, Bobby, but we'll save that for another day. In the meantime, Johnny can tell you what my sister Julie and her friends did to him. That should help you understand what’s in store if you don’t behave." I started to walk away, then paused, turning back. "Oh—and I’d appreciate it if you two hung out here every lunch. We might want to drop by for a little playtime. We’ll be in touch. Let’s go, girls."

With that, the three of us walked away giggling, leaving Johnny to rescue his clothes and Bobby to contemplate his ominous future.
Last edited by Blondie on Mon May 11, 2026 12:21 am, edited 4 times in total.
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The Felicity Chronicles: My Exploits as a Humiliator, Chapter 9

Post by Blondie »

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Chapter 9: Ruby: Spanked in the Bathroom (ENF)

In the days following our debasement of Johnny under the tree, Andrea, Natalie and I would regularly congregate in the cafeteria during the lunch hour. Invariably our conversation would turn toward Johnny—sometimes Bobby—and we’d dissolve into laughter, reliving the details of his humiliation, or plotting what else we could do with either one of them.

But one day, Andrea’s tone changed. She picked at her salad and glanced at Natalie before fixing her eyes on me. “So, Felicity,” she began, her voice low, “we wanted to talk to you about another situation.”

“Sure,” I replied casually, sipping from my water bottle. “What’s up?”

"Well, there's this girl, Tina. We go back to middle school. Actually, there are two of them, Tina and her friend Ruby. But Tina's the worst. Anyway, they've both been bullying us on social media."

I straightened in my seat. “What are they actually saying?”

"Well, “Tina knows Natalie and I are close. I don't know if she's jealous or what, but she's gone on Facebook and said derogatory things about both of us, even making stuff up. And she's telling people that we're lesbians."

I rolled my eyes. "Really?"

Andrea’s cheeks flushed. "Yeah. And even though I have light skin, she knows I'm Latina and there have been some... racist overtones in her comments. And Ruby has teamed up with her lately, doing the same thing."

“They sound charming,” I said dryly.

“I know,” Andrea said. “We don’t want to just report them or confront them directly. That wouldn’t change anything. But we figured with your, uh, creativity,” she grinned, “maybe we could teach them a lesson they wouldn’t forget.”

My first thought was that I would love to help them out. My second thought was that it would be fun to have a chance to humiliate a girl or two, especially ones so deserving. "I absolutely think we should teach them a lesson."

Both girls grinned. “We were hoping you’d say that,” said Andrea.

Ideas started tumbling through my head. I thought about utilizing Julie and her friends like I did with Johnny, but wondered if we could handle it ourselves. "How big are these girls?" I asked. "Do you think the three of us could take them on? I mean one at a time, of course."

Andrea glanced at Natalie, who was the strongest of the three of us. Natalie spoke up. "Tina's a mouse. I could bench press her. Ruby might be another story. She could probably put up a pretty good fight." Natalie paused to mull over a solution. "But..." Again she paused, deep in thought.

I nudged her, wanting her to keep going. “But what?”

"Well, it would involve adding another person into the equation," said Natalie.

I nodded, encouraging her. “You have someone in mind?”

"Her name's Kayla. They've been bullying her also. She's about my size and she works out like crazy—she’s probably stronger than me."

"Do you think she'd be interested?" I asked.

"Oh, I know she would," answered Natalie. "Those two have crossed the line with her, too. Kayla's Black, and there has been a racist remark or two from them. Nothing harsh, but enough to show up on her radar. She’s mentioned wanting to get even, so I think we could count on her if we wanted to go that route." She paused, then smiled. "Knowing her, she would probably like to jump in on our dealings with the boys, too."

“I think I already like her,” I said with a sly grin.

"Okay then," piped in Andrea. "It's settled. Natalie and I will talk to Kayla to make sure she wants to be onboard. I'm sure she will. Then maybe the four of us could meet here tomorrow and come up with a plan?"

"Works for me," I concurred.

"Oh, Felicity, thank you!" said Andrea as she reached across the table and put her hand on mine. "I'm so glad we've hooked up."

"Me, too," I said as I visualized humiliating my first female.

* * * * * *

The next day, I walked into the cafeteria and saw Kayla already sitting with Andrea and Natalie. She was everything they’d promised—tall with an athletic build, not an ounce of fat on her. She looked like she could play basketball, volleyball, or run track. She had a friendly face, and was smiling at me as we shook hands.

"I'm glad you've decided to join us, Kayla," I said. "I'm sure Andrea and Natalie have filled you in."

"Yes, and I want to thank you so much for letting me join you," she said as she extended her handshake a moment longer.

"My pleasure," I responded. "It sounds like we might need your help."

"Hey, anything I can do. I think I'm going to have fun doing it, too," she said with a grin.

I had a feeling Kayla was going to work out just fine.

The four of us went over our plan. It really wasn't that complicated. We would overpower them and get some incriminating pictures, putting them in a position where they felt compelled to do anything we wanted them to do. Ah, just typing the words "do anything we wanted them to do" excites me. Sooo many possibilities, and most of them involve stripping and humiliation.

First on the agenda was learning the habits of the two girls, which pretty much entailed stalking them for a few days. I put Natalie in charge of this, because luckily she shared the same second period class with Ruby and third period with Tina. The third period class occurred right before lunch, so it would be easy for her to pick up Tina's trail.

* * * * * *

Natalie reported to the rest of us each day. After three days, she came back with solid intel. “Ruby always hits the bathroom after second period,” she reported. “Every single day. Like clockwork.”

I cracked a satisfied smile. “So we have our venue. Any reason we can’t... do what needs to be done in the bathroom?”

"Sounds perfect," said Andrea. "No teachers will be in there. Not that that seems to matter around here,” she added with a chuckle. “Anyway, we should have free reign to do whatever we want. And there's a full fifteen minutes between second and third period."

"That's it, then," I declared. “Tomorrow, right after second period, outside the bathroom. We wait for Ruby.”

We were all onboard. Now we were all hoping that Ruby's bladder would remain on schedule.

* * * * * *

The stage was set. The next day, Natalie linked up with us after the second period. We stood near the bathroom with high hopes.

“There she is,” Natalie whispered, nudging me. Sure enough, there was Ruby, weaving her way through the busy hallway and heading straight for the bathroom, completely oblivious of her pending destiny with humiliation. We let her slip inside, then surreptitiously followed her in, pausing as she entered a stall and latched the door. We exchanged glances. This was it.

Kayla wanted to run with it. She looked at me and said, "May I?"

I held out an open palm toward the stall. "By all means."

Kayla crouched down and peeked under the stall. “Hey, Ruby,” she said cheerily.

“What the—HEY!” came the startled response.

What happened next was a spectacle—impressive, effective, comical and arousing. I watched in awe as Kayla dropped to her knees and went to work. With Ruby’s pants and underwear already partway down, Kayla seized the tops of both and tugged them halfway inside out over her feet in one smooth motion.

"HEY! WHAT THE FUCK?! HEEEY!" screamed Ruby, whose dignity was about to be further dishonored.

Kayla seized her ankles and yanked her right off the potty, dragging her under the stall door. Ruby, in a desperate bid to resist, clung to the metal divider—but quickly realized it only left her more exposed. She let go, and Kayla kept pulling until Ruby lay in the center of the bathroom floor, screaming bloody murder, face red with panic. It was an ingenious move on Kayla's part to only pull her pants halfway off, as Ruby's frantic kicks were considerably restricted.

"Get your hands off me, you fucking ape!" she screamed.

Kayla did not take kindly to the slur. She forcefully turned Ruby's ankles until she was on her stomach. She sat on the back of her legs, while Andrea and Natalie jumped in and restrained her arms and upper body, while I began delightfully snapping pictures.

Ruby was stunned, struggling to figure out what was happening. "Get off of me!" she screamed. “What the hell is wrong with you freaks?!”

"Time to get your white ass nice and rosy," declared Kayla. She pushed Ruby's shirt halfway up her back with one hand and began slapping her ass cheeks with reckless abandon with the other. She wasn't holding back, and sure enough, Ruby's backside turned a nice shade of pink in short order.

“NO! STOP! STOP IT! OW!” she howled, but Kayla was on a mission. She continued to smack the now flaming-red cheeks in front of her. Ruby was a beaten woman, and she started blubbering. "Please! No more! Please, it really hurts! Ohhhh!" she wailed.

A small, excited crowd had gathered near the entrance, peering in with wide eyes—some stunned, some laughing, all glued to the spectacle.

Kayla paused, her palm hovering over Ruby’s reddened skin. “Here’s how this is going to work. No more bullying. No more rumors. You even think about posting about us again, and I promise, this will feel like a warm-up.”

Ruby sobbed, voice cracking. “Okay, okay! I swear, I’ll stop! Please, let me go!”

Kayla shared a look with me, then delivered two more quick slaps on Ruby's very tender tushy. “You’ll do anything we say from now on. Say it.”

Through tears and gritted teeth, Ruby gasped, “Yes! Anything! Please, just stop!”

"Say, 'I'm your slave, Kayla.' " Another slap.

"Oh! I'm your slave, Kayla!"

"Say, 'I'm your slave, Felicity,' '" she prompted, slapping again.

Ruby probably didn't even know who I was, but she would get to know me better in due time. "Ow! Please! I'm your slave, Felicity!"

Kayla was on a roll, and I was enjoying it immensely. There was no need for me to do anything but keep snapping pictures.

Kayla barely paused for breath. "Say, 'You own me, Andrea.' " Slap!

"Aaahhh! You own me, Andrea!"

"Say, 'I'll submit to you forever, Natalie.' " Slap!

"Oh God! I'll submit to you forever, Natalie!"

"That's a good girl, Ruby," cooed Kayla as she caressed the toasty skin she had been violating. “But if you so much as whisper about us again, I’ll make this seem like a spa day. Got it?”

Kayla looked up to me, and I nodded. The three girls lifted themselves off the wretched Ruby, who then made a motion to get up.

"Hold it!" I said. "I need one more photo."

Ruby grudgingly but obediently remained prostrate on the cool bathroom tiles while I reached into my backpack, pulling out the two roses I’d snipped that morning from one of my dad's prized bushes. I still didn’t know what had prompted me to take them, but as pulled them out, inspiration struck.

I kneeled aside our sprawled-out victim. "Kayla, would you do me a favor and spread open Ruby's ass cheeks for me?" I asked.

"What? NOOO!" screamed Ruby.

Andrea pressed her foot into Ruby’s back, pinning her. Kayla, grinning, grabbed Ruby’s cheeks and spread them open. I slid the rose stem into the depths of Ruby's anal canal. I'm sure the thorns could not have felt good. Kayla let go and the red rose stood up on its own resplendently, eliciting a chorus of raucous laughter from the now twenty or so witnesses.

"Hey!" screamed Ruby at her latest indignity. "What are you doing back there?"

"Oh, I'm just gussying you up for your final photo. You can take your foot off her back, Andrea. Ruby, you stay put until I tell you otherwise."

I plucked the second rose from my backpack and crouched in front of Ruby, her flushed face inches from mine. She was still frozen in place, pants tangled below her knees, eyes darting between the four of us like a scared animal.

“Lift your head,” I ordered softly. Slowly, she did. “Open up.” She hesitated, but then her lips parted, and I set the thorny stem between her teeth. “Now, bite down—and don’t let go.”

She clamped her teeth down on the stem, and it was a sight to behold. She looked ridiculous, her teeth bared in a forced grin, a rose in her mouth and another projecting from her bum. I snapped the picture, savoring the moment.

"Very nice, Ruby," I said as I admired the result. It was... well, picture perfect. "Oh, you really must see this, Ruby," I said as I lowered my phone to her eye level. "Isn't that special?" I teased. The miserable, glassy-eyed expression on her face said it all. Our work was done.

"That's a wrap, girls," I said. "Thanks for modeling for me, Ruby. Oh, and you can keep the roses as a gift from me." Then I had an afterthought. I took the rose from her mouth. "Actually, I'll keep this one as a souvenir. I'd like you to wear the other one in your hair for the rest of the month," I said. "Call it a good faith gesture on your part. When it wilts I'll bring you a fresh one."

I leaned in just a bit to make my next point. "Every time one of us sees that rose perched up there—and for your sake, it better be there—we'll know that you belong to us." I smiled. "And you’ll know it, too. Don’t forget it.”

We filed out, high-fiving in the hallway, our laughter ringing off the lockers. It was cause for celebration—Ruby got her comeuppance, and I now had another plaything at my disposal.
Last edited by Blondie on Mon May 11, 2026 5:35 pm, edited 4 times in total.
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The Felicity Chronicles: My Exploits as a Humiliator, Chapter 10

Post by Blondie »

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Chapter 10: Tina: Forced to Pose Topless (ENF)

With Ruby now firmly under our control, our sights shifted to Tina. Natalie had been discreetly following her for days, and lunch hour seemed like our best bet. According to Natalie, Tina always brought her own lunch, avoiding the cafeteria altogether. The pleasant weather had her eating outside for the past three days, tucked away on a secluded bench behind the gym. Sometimes she was alone, other times with one or two friends. We decided that if we caught her alone or with just one companion, we’d make our move.

On the fourth day, Natalie reported to us about five minutes into the lunch period. It had been just over an hour since we’d left Ruby howling in the girls’ bathroom, and we had just taken our seats.

"She's there," Natalie said breathlessly. "And she's all by herself."

Lunch could wait. "Let's go!" I said, and we all stood up in unison, following Natalie outside.

Anticipation surged through me, a familiar thrill that always hit before a humiliation episode. The thought of taking down both targets in one day was exhilarating.

We rounded the corner of the gymnasium, and there she was—sitting on a bench against the brick wall, lunch in hand, nose buried in a book. Natalie nodded and stepped aside, letting me take the lead. I scanned the area, and there were a few scattered students milling about, over two hundred yards away. I could see this wasn't going to be a problem.

"Hi, I'm Felicity," I said, startling her. She looked up and saw the four of us standing over her. “I believe you know my friends,” I added, gesturing to the others.

“What do you want?” she asked, trying to sound nonchalant, though the faint tremor in her voice gave away her fear.

I held up my phone. "I'd like to take a picture of your tits. Would you mind taking off your blouse?"

She was wearing a loose-fitting, lavender blouse with buttons, paired with a black skirt that ended just above her knees. Easily one of the best-dressed students at Roosevelt.

"What? No!" she responded, her voice sharp with alarm. "Who are you?" She was definitely concerned now, and was looking around, either for help or for an escape route.

I smiled. "Well, I think in time you'll see I'm your worst nightmare. But right now I'm just someone who wants a nice picture of your tits," I said matter-of-factly. "But I can't accomplish that until you take off your blouse and bra. You are wearing a bra, right?"

She wasn't about to discuss her undergarments with me. She tried a conciliatory approach. "Look," she said, glancing from face to face among my three companions. "If this is about those Facebook posts, I'm really sorry. I was just messing around. I promise to never say anything bad about any of you again. I promise."

Kayla chimed in, her voice cool. "Oh, we're sure you won't. But Felicity still needs a picture of your tits." I smiled. Kayla was proving to be a wonderful addition to the group.

Tina's eyes widened. She had come to the realization that she would have to either fight or run to avoid whatever debasements we had in store for her.

She chose to run. But she was neither as quick nor as strong as Kayla, who pounced on her like a tiger fixed on her prey. She subdued her easily, wrapping her arms around her from behind. Tina's kicks and struggles went completely for naught.

"Let me go! Let go of me!" she screamed.

"Hold her legs," I commanded. Andrea and Natalie each grabbed a leg, lifting them off the ground. With Kayla's iron grip, Tina was helpless. I calmly removed her two-inch heels, tossing them aside.

"Stop it! Please! Stop!" Tina yelled, her voice raw with panic.

Without a word I casually unzipped her skirt and slid it down her thighs, revealing white nylon panties over beige stockings. She thrashed wildly, but it only heightened my excitement.

"No! Please! Stop! Stop it!" she screamed. Her frantic pleas were music to my ears. I pulled her skirt down to her ankles, where Andrea and Natalie slipped it off her feet.

"You can let go of her legs," I told them. They did so, and Tina's feet hit the ground. She had given up on her struggle, resigned to the fact that she would not be able to extricate herself from Kayla's vice-like grip.

I stepped in close, savoring the tremor that ran through her. "Tina, Tina, Tina," I said. "You could have made this easy. All you had to do was take off your blouse and let me take a picture of your little titties. But you had to resist. Now look at you—you've lost your skirt. Do you want to end up completely naked?”

Her eyes went huge. "No!" she screamed.

"No, what, Tina?" I wanted to hear her say the word "naked" while I pictured that delightful image.

Her cheeks burned as she whispered, “No, I don’t want to be naked.”

"Here's the deal, then, Tina. I'm going to give you one more chance. All I want is a nice little picture of your tits. So you’re going to take off your blouse and your bra. You are wearing a bra, right?” I asked, glancing down at her chest. She nodded, lower lip quivering, tears in her eyes. "Good. Take off your blouse and bra, and I'll take some pictures. After that, you get your clothes back. Fair enough?”

She didn't respond. I'd venture to say that the humiliating act of stripping herself and posing for pictures didn't appeal to her. (giggle) Of course, we could have had her blouse off in seconds flat. But making her play an active role in her own humiliation was much more fun—and twice the shame.

"You do have a choice, Tina," I said. “I can’t make you take off your top. But if you don’t, well..." I turned to Andrea. " Andrea, what do you think happens if Tina won't take her top off for us?"

Andrea didn’t hesitate. "Easy. She ends up naked."

"Exactly," I said. "And Tina already told us that she doesn't want to be naked." I addressed Tina. "You still don't want to be naked, do you, Tina?" She shook her head slowly and dejectedly. I could see the defeat in her posture, and I knew she would submit to me. It was a delicious moment.

“So that leaves only one option.” I lifted my phone, readying the camera. "You can let go, Kayla. I think Tina's ready to take her top off."

Kayla loosened her arms, stepping back with a knowing smirk. Tina stood frozen, eyes glued to the ground, arms crossed tightly over her chest.

“Natalie, would you help Tina get her heels back on?” I asked. "I think it would make for a much more provocative picture. I'm so glad Tina got dressed up for us today."

Natalie giggled, kneeling to retrieve Tina’s shoes and slip them gently onto her feet. I thought the heels accentuated Tina's slender legs, and really added to the scene. I couldn’t help but grin as I snapped a quick picture of her—half-dressed, shaking, and utterly at our mercy.

"It's time, Tina," I said. She stared at the ground, motionless. "We don't have all day, Tina." She made a hesitant move to lower her arms, then clamped them even tighter. Her reluctance only added to my enjoyment, as we both knew she was only prolonging the inevitable. I've often likened the buildup before a stripping to foreplay before intercourse, and that is exactly what it felt like for me.

"Okay, girls, strip her naked," I commanded.

The three of them advanced, and Tina’s composure shattered. “No! Wait, please—okay! I’ll do it! I’ll do it!” she sobbed.

I knew she'd see it my way.

I raised a hand, motioning the girls to back off. “Let’s give Tina some space,” I said, relishing the control. The four of us stood and watched intently as she slowly, tentatively reached for her top button. She was sobbing quietly, and her hands were shaking. She forced herself to continue, unbuttoning, exposing a glimpse of her pale belly and a trace of her white bra beneath. She hesitated, seemingly unable to move.

"You can just let your blouse fall to the ground, Tina," I coaxed.

At that moment I really wanted to put my hand inside my panties, such was my state of stimulation. It was a wonderful vision for me as Tina, her cheeks now glowing crimson, shrugged the blouse off her shoulders and let it slide to the concrete. She instinctively crossed her slender arms over her chest, which I found delectable. The sight of her shivering in her bra, panties, stockings, and heels was really a turn-on. I quickly snapped a photo, knowing I would later use it for my own pleasure.

"Let's have those arms down, sweetie. I want a nice shot of you in your underwear."

Tina ever so slowly lowered her arms to her waist. When she did, I could see why she was so reluctant to do so. Let’s just say I’ve seen pancakes with more contour than what Tina was hiding under her arms.

The moment her secret was out, my three friends burst into giggles, and I joined in. Oh, I was going to have so much fun with this girl.

"My, my, Tina," I teased. "Now I see why you were so reluctant to take your blouse off. You have a little boy chest. Why do you even bother with a bra?"

My friends laughed, and Tina flushed brighter while crossing her arms over her chest again. She glanced over my shoulder, her eyes widening. I turned just enough to see the cause: About a dozen curious students, boys and girls alike, had gravitated closer to us and were observing the scene with eager interest.

“Well, would you look at that,” I grinned, turning back to Tina. “You’ve attracted an audience, sweetheart. And I think they all want to see your little titties." I turned, giving the onlookers a little wave before refocusing on my quivering victim. "Let's get those arms down again, Tina. I don't want to have to tell you again." Her eyes darted over my shoulder at the gawkers, but she obeyed, letting her arms fall once more.

I decided to twist the knife. “What size is your bra, Tina?”

She stared at the ground, silent.

"I asked you a question, Tina."

"It's a... thirty-four,” she choked out.

"And the cup size?"

There was a long pause before she said, very softly, "Double A."

"Double A!" I crowed. "How old are you, Tina? Eleven?"

“F-fourteen,” she whispered. “Please, just let me go.”

I shook my head. “We will, but not until I get some pictures of your little titties. Take off the bra, Tina.”

Tina was in no rush to do my bidding. "It's okay, Tina, I do understand. If I were you, I would be extremely self-conscious about exposing my thirty-four double-A's in front of all these people. But we're not leaving here without some pictures of your bare titties. So the sooner you get that bra off, the sooner this will be over for you."

Tina knew what she had to do. And to my absolute delight, she reached behind with one trembling hand and unhooked her bra. The straps slid off her shoulders and dangled uselessly at her sides as she clutched the cups to her chest in one final act of protecting her modesty. Honestly, the drawn-out nature of her own stripping only made it all the more delicious. It was much more stimulating than it would have been had she just taken off her blouse and bra without all the dithering.

I think Tina finally decided that her best course of action would be to get her ordeal over with as quickly as possible. She seemed to steel herself and then, in one swift motion, let the bra fall to the ground. The crowd responded with laughter and applause. Of course, she immediately covered her chest with her arms, her face now scarlet. It was a beautiful sight—one I would relive often while enjoying the pictures I was about to take.

"Let's get those arms down now, Tina. I need pictures, and everyone wants to see your little titties."

With agonizing reluctance, she lowered her arms, much to the excitement and amusement of her audience. What an excruciating moment that must have been for her! She truly had very small breasts—really just a couple of nubs. To have to expose them to all these laughing people under those conditions... golly, if I wasn't having so much fun, I might have felt sorry for her.

“Oh my, Tina,” I taunted, snapping a photo. “Your titties are even tinier than I expected. Tiny Tina, that’s what we’ll call you from now on.” Everyone around us laughed, and poor Tina just kept falling deeper into the depths of her mortification.

"Okay," I continued. "I'll need to get a few more shots before you go. Let's see, fists on hips. Good. Stand up straight. Head up. Excellent," I said as I took a photo of a girl with probably the most miserable facial expression I've ever seen.

"Nice, Tina. Now one hand on your hip, the other behind your head. Pretend you're a model doing a photo shoot. Yes, oh, that's sensual. Can you smile for me? No? Okay, I'll take what I can get."

Click

"Now both hands on your head. Elbows out. Head back, tummy in. Perfect! My God, that pose makes your chest look flat as a board."

Click

"Just one more pose, sweetheart. One hand behind your head, and point at the camera with the other. Yes! Just like that! Now straighten your arm while you point. Good, Tina! Can you look sexy for me? We're not going anywhere until you look sexy for me. Come on, open those pretty eyes, purse your lips for me... yes! Hold that look!"

Click, Click

“Excellent!” I said, lowering my phone, thoroughly pleased. “We’re done. Girls, let’s give Tiny Tina a round of applause.”

The four of us—and a few of the onlookers—clapped heartily. Tina, thoroughly shamed, gathered her clothes, desperate to cover up. When she reached for her bra, I stopped her.

"Hold on! I'll be taking that," I said, gently plucking it from her grasp and tucking it in my pocket. "I'll be keeping this as a souvenir. Honestly, you really don't need it." That gave me an idea. "In fact, from now on you're not to wear a bra until you grow some big girl tits. Girls, feel free to ask Tiny Tina to show you her little chest any time, just to make sure she's going braless."

Tina whimpered as she dressed, sniffling audibly. I picked up her phone, sent a quick “hi” to myself, and handed it back. “Don’t worry, I’ll send you the pictures later—something to remember today by. And now I’ve got your number if I want to set up another playdate.” She didn’t answer, so I leaned in a little closer.

"So tell me, Tiny Tina. What did I say you're not allowed to do, starting now?" I asked. It's so much fun to make them vocalize what I've asked them to do for me—especially when it's something humiliating like this.

"I... I can't wear... that." She pointed to the bra strap that was dangling from my pocket. I smiled to myself, then persisted.

"Can’t wear what, Tina?"

Her voice was a whisper. “A bra.”

“That’s right. Not until you grow...?” She stared blankly, so I gestured at her chest.

"Some... some..." She really had trouble with that one. "Some big girl tits," she finally managed, inducing hearty laughter all around, causing her face to go redder still.

"Gooood, Tina," I said. "Oh, and one more thing. Unless it’s pouring rain, you’ll be eating lunch right here from now on. Tell your friend Ruby I said she should join you. Tell her I said that would be rosy. You two can swap humiliation stories while you wait for us to come play with you."

We turned and walked away, feeling quite pleased with ourselves. From a personal standpoint, I had added a second female victim. My passion to humiliate was being fulfilled, and I felt like there was no stopping me. Four years at Roosevelt High suddenly felt far too short.
Last edited by Blondie on Mon May 11, 2026 10:07 pm, edited 4 times in total.
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Re: The Felicity Chronicles: My Exploits as a Humiliator

Post by TeenFan »

When it comes to teenage girls in these types of stories I often prefer the girls have smaller breasts.
I guess I like smaller most of the time, knowing that large ones will often be looking like half filled hot water bottles, saggy and
droopy by the time they reach their twenties. Big boobs (when they are natural) tend to come with being big all over and I want them to
go on a diet.

I like SBH more than SPH. Weird huh...
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The Felicity Chronicles: My Exploits as a Humiliator, Chapter 11

Post by Blondie »

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Chapter 11: Johnny Boy: Marching in Tighty-Whities

One afternoon, Natalie, Andrea, Kayla, and I were finishing up lunch when the conversation lulled for a moment. I was in a particularly mischievous mood, and I thought it might be fun to pay a visit to a couple of our recent playmates.

As you probably remember, Johnny Boy’s latest claim to fame involved him standing around in nothing but his underpants, shivering under a tree by the football field while his friend Robert—I call him Bobby, which he apparently doesn't like—tried to step in and defend his friend. A gallant gesture to be sure, but foolhardy. I warned him then that there would be consequences for his interference.

My parting instruction had been very clear: Both boys were to spend every lunch under that very tree, no excuses, no exceptions. It’d been about a week and a half since then, and it felt like the perfect day to remind them who was in charge.

A sly grin crept across my face. “Should we go check in on the boys?”

Immediately, the girls perked up. Kayla, in particular, seemed extra enthusiastic—probably because she hadn’t been around for our moment with Johnny Boy. She seemed to really enjoy humiliating Ruby and Tina, of course, but I got the impression that she was even more interested in humiliating the boys. Nothing I could put my finger on—but I’d picked up an extra bounce in her tone whenever the boys were mentioned.

As we drew closer to the tree, I spotted Johnny sitting beneath it. Alone. That simply wouldn’t do.

“Johnny Boy!” I called out. He jolted, his whole body tensing. I could practically taste his fear as we descended on him. “Nice to see you, Johnny,” I said, leading the girls right up to him. “Stand up, would you? There’s someone I want you to meet.” He hesitated, then got to his feet, shoulders slumping. “Johnny, this is Kayla. Kayla, Johnny Boy.”

Kayla flashed a delighted smile. “Hi, Johnny Boy,” she chimed, extending her hand, which Johnny accepted halfheartedly without meeting her gaze. Kayla's smile turned devilish. "I'm really sorry I missed you the other day."

The pleasantries ended there. “So,” I said, folding my arms, “why isn’t Bobby here?”

“I... I don’t know,” he muttered feebly.

"I told both of you that I wanted you here every day. And yet here you are, alone. This is not good. Does Bobby not understand how important it is to follow my rules?”

Johnny squirmed, shifting his weight, his hands fidgeting at his sides. “I—I’m not sure.

“Do you understand how important it is to follow my rules?" I pressed.

“Yes... y-yes, I do.”

I gave him a slow, measured look. “I’m not so sure, Johnny. If you truly did, your friend would be here. And he's not here, is he, Johnny?"

"No, but..."

"No buts, Johnny," I interrupted. "I told both of you what I wanted, and one of you has disobeyed me. I'm holding both of you accountable. And both of you are going to have to be punished."

His face went pale, and I could see the nervous sweat forming at his hairline. “I’m s-sorry,” Johnny managed, voice trembling. “I didn’t think—”

"That's exactly the problem, Johnny. You didn't think. If you had thought this out you would have made sure Bobby was here. You've been a bad boy, Johnny. You know what I do to bad boys?" I stepped in close, tugging the hem of his T-shirt free from his jeans. He flinched, his breath quickening. I put my hands gently on his shoulders and leaned in, my voice low. "I punish them. And do you know how I punish bad boys, Johnny?" The obviously frightened Johnny didn't answer, so I helped him out. "I'll tell you what I do. I get them very, very embarrassed. So embarrassed that they can barely breathe." Johnny's breathing indeed became heavier, and the look of panic in his eyes was delightful.

“Remember how hot your face felt when you ended up in your underpants last time?” It was a rhetorical question, and I didn't expect an answer. "Trust me, I can make you even more embarrassed than that." He stared at me, wide-eyed. “How do you think I might do that, Johnny?”

He was trembling now, on the verge of tears. “P-Please,” he whispered. “I’ll make sure he’s here next time. I promise. Just—”

“Oh, I’m sure you will, Johnny. But as we've established, he is not here right now. And we wanted to see both of you. And you need to be punished, in a way that leaves you even more embarrassed than last time.” The panic in his eyes said it all. “So, Johnny Boy,” I said with a slow smile. “How do you think we should make that happen?”

“I... I don’t know,” he managed, voice barely there.

"Well, let's think this through," I said. "Last time we stripped you down to your tighty-whities. That was very embarrassing, wasn’t it? I mean, your face was as red as a tomato." Johnny looked like he wanted the earth to swallow him whole. "And now we're looking for a way to make you even more embarrassed. So, unless you have a better idea, I was thinking that maybe we could take your underpants off this time. Would you like to be naked, Johnny?"

I love asking that question. It always elicits a wonderful reaction, either audible or physical—usually both. To this day no one has ever answered in the affirmative. (giggle)

“No! Please—don’t!” Johnny blurted, eyes wide.

I grinned and reached for his shirt, lifting it slowly. Kayla and Andrea, clearly catching on, crouched to remove his shoes and socks like a pit crew. "Let's have those arms up, Johnny," I directed. As Johnny raised his arms he let out a barely audible whimper, which I found adorable. Subtleties like that truly add to the experience for me.

I whisked his shirt away, tossing it to the ground. Johnny crossed his arms over his chest, looking miserable. He was now barefoot and shirtless, a helpless victim in fear of my next move. It was awesome.

“Hands behind your head, sweetie,” I said. He flinched, but obeyed. “Good boy. Elbows out to the sides. Show us your armpits.” I looked under his arms and smiled. "You look so cute with your hairless underarms on display like that." The girls giggled and Johnny blushed brighter, while I beamed with pleasure. He really did look adorable, with his soft, youngish features. So innocent looking, and blushing beautifully.

I moved behind him and slowly, teasingly ran my fingertips down his chest, across his nipples and down his sides. He shivered deliciously. I rested my hands on his belt buckle, then glanced around. We’d drawn a small audience, which I'm sure wasn't lost on Johnny.

“Look at that, Johnny. You’ve got fans again," I noted cheerfully as I unbuckled his belt. "You're becoming quite the celebrity aren't you?" His breathing became more rapid as I unbuttoned his jeans and fingered his zipper. He jerked his body slightly because of my proximity to his privates, which brought a smile to my face. "Don't worry, Johnny Boy, I'll be gentle with you," I teased.

"Please," he begged, his voice barely audible. "Please let me go."

I ignored him. "Are you wearing your tighty-whities again, Johnny Boy?" He didn’t answer, so I pressed. “Answer me, Johnny.”

He nodded reluctantly. “Yes... please, don’t...”

“I'm so glad. You look adorable in them. I want you to wear your tighty-whities every day for me. Will you do that for me, Johnny?"

"Okay," he yelped softly.

As I tugged his zipper down, I said, "Look at Kayla." Kayla was grinning widely in anticipation, her perfectly white teeth contrasting nicely with her dark complexion. "Kayla hasn't seen you in your tighty-whities yet. I think she's really looking forward to it."

"Please don't... don't do this!" he shrieked.

I was about to pull down his jeans, then paused as inspiration struck. I love it when I have an inspiration amid a humiliation episode. I pulled his zipper partway up, then I let go. They hung precariously at his hips.

"Andrea," I said as I walked around Johnny to face him, "Could you find a marching song on your phone for me?" I'm not sure if Johnny knew where this was going, but a few people giggled while Andrea did her search, so some of them had a pretty good idea.

"Got one!" called out Andrea.

“Excellent. Cue it up, full volume. Natalie, record this, please. I have a hunch this will be good."

“Already recording,” Natalie replied.

I turned back to Johnny, smiling. "Since you said please, I'm not going to pull your jeans down. Okay, Johnny?"

He wasn't quite sure what to make of that concession, but he responded, somewhat hopefully. "Okay. Thank you." It was really cute.

“But,” I said, leaning in, “in return, you’re going to do a teeny, tiny little thing for me, okay Johnny?"

He nodded, looking like he might faint.

“In a moment, Andrea’s going to play some music for us. When it starts, I'd like you to march."

I studied Johnny's face and waited. I think being under such duress must have affected his cognitive thinking, because it was a good five seconds before he realized what the ramifications would be from lifting his legs up in the air. His wide-eyed expression when it kicked in was priceless.

"You can just march in place, Johnny," I instructed. "But I want you to get those knees up high, just like you're in a marching band. And make sure your hands stay behind your head."

I nodded to the grinning Andrea. Right on cue, the cheerful beat of marching music filled the air. I found out later the piece is called Radetzky March, by Johann Strauss, Sr. It was perfect.

Here is a little snippet of it. As you listen, try to imagine poor Johnny Boy marching to it in his tighty-whities for our entertainment.

Radetzky March

Initially Johnny remained motionless, unable to do my bidding. Of course, this was a temporary condition, as was the status of his jeans. "March, Johnny Boy!" I shouted, clapping my hands. "I want to see you march! Lift those knees up!"

Johnny, who (quite deliciously, I might add) was struggling to prevent the result that was certainly a foregone conclusion, lifted one leg... then the other... very gingerly. Even that small effort caused the tops of his jeans to loosen slightly from his hips, thus exposing the top two or three inches of his underpants, much to the delight of the onlookers.

“HIGHER, Johnny! Like this!” I demonstrated, knees to my waistline.

Johnny's fate was sealed. The moment he complied, his jeans dropped to his thighs, where they ever-so-briefly stalled at his knees before his next steps brought them down to his ankles unabated. The crowd burst into laughter, and Johnny turned scarlet.

“Don’t stop, Johnny!” I whooped. “Keep marching! You’re not done yet!”

Much to everyone's merriment, Johnny continued his awkward march—knees high, his jeans tangled at his feet. Andrea and Kayla zealously jumped in and with adept teamwork they tugged and yanked until they'd wrestled the jeans clean off. All the while, Johnnie obediently continued to march to the rhythm, arms still locked behind his head. It was almost like the music was a driving force, and he couldn't stop—like he was possessed!

I seized the moment, nudging him from behind, guiding him forward. “March in a circle around the tree, Johnny. Let everyone get a good look.” And bless him, he did. Three times. Red-faced, arms up, while our audience shrieked with laughter.

He looked so funny, all red-faced, nearly naked, parading in circles like a wind-up toy on put on display for everyone's amusement. It remains one of the funniest things I’ve ever witnessed, and judging by the howls from the crowd, I wasn’t the only one. I still can’t think about it without laughing.

* * * * * *

That was as far as we took things that day. I had fully intended to strip Johnny Boy naked—believe me, the temptation was certainly there—but all things considered, I decided that we had already reached such a spectacular level of humiliation that taking it further risked becoming almost anticlimactic. Best to save his first naked humiliation for another occasion—though in retrospect it would have been awfully stimulating to watch him parade naked around that tree.

I must admit I'm getting turned on just fantasizing about that. So, if you'll excuse me, I need to go take care of something. :P
Last edited by Blondie on Tue May 12, 2026 6:33 am, edited 5 times in total.
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The Felicity Chronicles: My Exploits as a Humiliator, Chapter 12

Post by Blondie »

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Chapter 12: Blondie: Naked in the Roosevelt Hallway

I'll get back to my ongoing account of Blondie's epic humiliation during my thirteenth birthday again someday, but right now feels like a perfect time to tell you about my very first encounter with him after I started at Roosevelt High. Blondie has always been my favorite—he’s just so adorable when he blushes, and he squirms so cutely when I tease him. And the fact that he was my virgin experience in this delicious little world of humiliation probably has a lot to do with him being my fave.

It happened during my second month at Roosevelt. The memory of that unforgettable night with Blondie—my birthday gift—was still fresh in my mind. I was at lunch with my usual crew. We’d been reminiscing about how much fun we’d had tormenting Johnny Boy, Ruby, and Tina, when the conversation drifted to Blondie. I started launching into a play-by-play of how I’d teased him that night on Becky’s bed. Blondie was naked. I was not. (giggle) They were enthralled, hanging on every word.

Then the five-minute warning bell rang. “We’ll have to pick this up tomorrow,” I said as we gathered our trays.

“Wait—where does this Blondie boy go to school?” Andrea asked.

I tried to seem casual, but I couldn’t help but smile. "Oh, he's right here in the hallowed halls of Roosevelt High."

Andrea’s face lit up. “Seriously? Is there any way we could, you know, meet this guy?”

"I think that can be arranged," I replied with a twinkle in my eye.

"Oh, that would be awesome," Natalie chimed in.

Kayla grinned, nudging Natalie. "Count me in! Maybe we can have some fun with him, if you know what I mean—and I think you do."

The four of us laughed exuberantly as we parted ways, and I was already plotting on my walk to the next class. Oh, it was going to be fun to “catch up” with Blondie. My new victims had kept me busy, but Blondie had never really left my thoughts. I felt a rush of anticipation now that an encounter with him was on the horizon.

That evening, I called Blondie's sister, Becky. Becky wasn’t sure about his full schedule, but she did give me a useful tidbit: His second period class was in Room 213. She knew because hers was in 212, right next door, and she’d seen him come out a few times. That was all we needed.

The next day at lunch, I laid out what I’d learned for the girls. Andrea grinned devilishly. “That's perfect. We’ve got fifteen minutes between second and third periods. Just enough time to get properly acquainted."

The plan was set. Well, actually there wasn't much of a plan. I think the girls had seen me in action enough and trusted me to wing it. I was more than confident I could justify their trust.

* * * * * *

The following morning, we met up just after second period at the foot of the main staircase. At Roosevelt the juniors and the seniors had their classes on the second floor, while the freshmen and sophomores were on the first. The lockers were divided the same way.

We hustled up the stairs, weaving through the hordes of students, and just as we neared Room 213 I spotted the blond-haired (well, duh) Blondie stepping into the hallway. I felt a tingle of pleasure, as the memories of my thirteenth birthday gave me a delicious rush. “There he is,” I whispered to the girls, my heart skipping a beat.

Natalie eyed him and said, “He’s a senior? He looks like he should barely be out of middle school.”

“I know,” I grinned. “Isn’t that adorable?”

Blondie, oblivious, led us a short way to his locker. He’d just turned the key and swung the door open when I stepped up beside him and gave his shoulder a gentle tap. “Hi, Blondie,” I said, all smiles. “So nice to see you again.” He jumped, startled, and for a split second I caught the recognition behind his eyes—followed instantly by dread.

“I brought some friends who’ve been dying to meet you,” I said, gesturing to the three beaming girls behind me. “Girls, this is the one and only Blondie.”

“Hi, Blondie!” they sang in unison, grinning broadly. Blondie just stared, speechless. I'm pretty sure he had already figured out that we probably weren't there for a friendly meet and greet.

“Felicity’s told us so much about you,” Andrea said, eyes sparkling.

“And yesterday,” I continued, savoring every word, “I was telling them about how we sat on Becky’s bed that night...” His cheeks flushed instantly, much to my delight. “And how pretty your legs are,” I added, winking at the girls.

I turned to them. “Would you like to see how pretty Blondie’s legs are?”

"Ooh, yes, could we?" Kayla asked, peering down at his legs, which at the moment were shrouded by a pair of jeans.

I put on my sweetest voice. “Could you show us your lovely legs, Blondie? Pretty please?”

He finally spoke, his voice cracking. "P-Please, Felicity. Just... just leave me alone."

“Oh, we will, Blondie. Just as soon as we see your legs.”

Even though no words had been spoken between us for about three months, it was pretty much a tacit understanding that he would have to submit to whatever demand I had. The pictures and videos I have from that night are far too incriminating. Amusingly, he bent down and pulled up one pant leg, showing off a few inches of pale calf. It was cute how hopeful he looked, like maybe that would be enough.

“Oh, that’s very nice, Blondie,” I cooed, stepping in closer. "But we need to see more than that." I reached for his belt and began unbuckling it. Ever the compliant one, he barely flinched. He knew me well enough to know that regardless of whatever attempt he would make to resist, that I would eventually get my way.

“Please, Felicity,” he whispered, glancing around nervously. “Not out here...”

“You’ll be fine,” I whispered reassuringly. "The four of us are blocking the view. Hardly anyone will see.” The lecherous grins from my three friends didn’t seem to help his nerves much.

I unfastened his jeans and started to unzip. I guess he couldn't help himself, and he grabbed my wrists. It was more a reflex than real resistance.

“Blondie,” I said, letting him hold me for a moment, “do you remember when we were in Becky’s room, and you were standing on the stool in your cute little panties?” The blush that instantly crossed his face was a shade of red I hadn’t seen in months. The girls giggled. “Do you remember where your hands were?” I asked. He gave a reluctant nod. “Good. That’s where I want them now.”

He slowly raised his arms and interlocked his hands behind his head. The tittering from the girls grew. To add to his anxiety, I'm sure he noticed that a few other students had become aware of the situation and were looking on in fascination.

"That's a good boy, Blondie," I purred, easing his zipper down. “Now let’s have a real look at those pretty legs of yours.” I turned to my eager assistants. "Girls, would you mind getting Blondie's shoes and socks? We want the full view." Andrea and Natalie had Blondie barefoot so quickly it was as if a magician had made his shoes and socks disappear.

"Kayla, would you mind pulling Blondie's shirt out of the way a little bit so there's nothing obstructing our view?"

“Absolutely,” she chirped. The ever-devious Kayla didn’t stop there—slipping behind him, she peeled his long-sleeved black tee inside out over his head, then yanked it completely off. She held it up exuberantly.

“Thank you, Kayla,” I giggled, patting Blondie’s now-bare chest. "I guess it's out of the way now.”

I knelt, savoring the moment, and slowly eased his jeans down, letting them bunch at his ankles. Not wasting any time, I lifted his feet free, whisking the jeans away.

And there he was—my beloved Blondie—blushing crimson, clad only in bright red boxers that perfectly matched his glowing face. A light trace of hair had returned to his legs since the Becky/Brenda makeover, but they still looked delightfully smooth and quite adorable. I ran my fingers up one of his calves, relishing the tiny twitch it provoked.

“Oh, Blondie,” I sighed, standing and cupping his hot face in my hand. “Your legs are still so pretty. Not quite as silky as before, but still quite lovely.” I paused, slipping my fingers around the waistband of his boxers. “Shall we take these down and have a look?”

“No! Please!” he yelped, panic in his voice. By now, a small crowd had gathered, drawn by the spectacle, and Blondie clearly noticed.

“Do it!” a girl’s voice shouted from behind us. I knew instantly it was Becky, Blondie’s sister. Blondie's eyes went wide as he realized both Becky and Brenda were in the crowd. I shot them a little wave. Becky grinned and gave me a thumbs-up. Seeing Blondie's own sister and his old nemesis watching only stoked my wicked side. He was rattled, and I was eager to put on an even better show for them.

I actually wasn't planning on exposing Blondie's little penis during that encounter. The idea had been to introduce him to my friends, and embarrass him by displaying his underpants—simple, public, just a touch mean. But once I saw that look in his eyes, the way he quivered with each new humiliation, I just couldn’t help myself. I was caught up in the moment, he was ripe for the taking—and, well, it was Blondie, after all. He brought out the most delightfully wicked side of me. And how fitting that Blondie would be the first of my victims at Roosevelt to endure the humiliation of having his privates bared before a giggling audience.

So I knelt down and began to tug his boxers down, slowly, relishing every shocked gasp from the crowd as Blondie’s penis came into view. I continued pulling down until his shorts rested at his knees. Blondie trembled like a leaf, his hands still obediently locked behind his head.

I was a little disappointed to see his pubic hair had grown back some, but I was happy to see that his penis was still as small as I remembered. I found it kind of cute, really, and it was perfect fodder for teasing—plus so embarrassing for him!

It was absolutely exhilarating to exercise my control over Blondie again and humiliate him like that. As I've said, he was my favorite plaything. It was like playing with my favorite childhood doll—only this time the doll was alive, humiliated, and capable of reacting, which made the excitement a thousand times sharper. And let's face it, I never got sexually aroused playing with my dolls. (giggle)

“His weenie’s kinda weenie!” a girl in the crowd giggled, setting off a whole new wave of laughter. Poor Blondie. He was absolutely crimson. How excruciating it must have been to stand there—hands behind his head, shorts at his knees—knowing exactly what everyone was staring at.

“Strip him naked!” someone else called out. I glanced over my shoulder, gave the crowd a sly, knowing smile, then turned back to Blondie—looking forward to doing exactly that.

With a gentle tug, I slid his boxers all the way off, letting them drop to the growing pile at his feet. Now, completely naked, Blondie stood before us—totally exposed, utterly mortified. Vulnerable as anyone could be. I could practically hear his heart pounding—and honestly, mine was racing just as fast.

I rose, hands on my hips, and took a moment to survey the scene I’d created—to really soak it all in. It felt almost surreal. Here I had this boy, completely naked and adorably mortified. And this wasn’t just any boy trembling in the hallway. This was Blondie... my first, my favorite... and he was completely, exquisitely at my mercy.

I watched him fidget and flush and felt a delicious mix of giddiness and satisfaction washing over me—not to mention a certain amount of erotic stimulation. I’d fantasized about moments like this before, but now it was real. I had made it happen. I couldn’t believe my good fortune. Somehow, I'd been handed this golden opportunity—and I wasn’t about to waste it.

"Look at you, Blondie. You're naked!," I declared. I looked him up and down, grinning. "Say it."

Blondie knew what he had to do. "I'm naked," he said softly. Everyone laughed, and he somehow turned a deeper shade of red.

"Yes you are! everyone’s getting a good look at your little pee-pee,” I said while gently taking hold of his little pee-pee with my thumb and two fingers and jiggling it back and forth. Blondie gave a strangled gasp and almost leaped out of his skin. Laughter exploded around us, echoing off the lockers, and his miserable expression said it all.

I was almost done with him, but I had a few parting instructions that would help secure his embarrassment for weeks to come. I flashed him a sweet smile. “I’ll let you get dressed in a minute, Blondie, but first I’ve got some things I want you to do when you get home. You will do everything I ask you to do, right Blondie?" He nodded meekly. I wasn’t letting him off that easily. "I need to hear you say it."

“Y-yes,” he eked out, voice trembling.

“Yes, what?” I pressed, relishing his discomfort.

"Yes, I'll do what you ask me to," he whispered desperately, glancing nervously at Becky, Brenda and the steadily growing crowd. "Please, can I just get dressed while you tell me?"

I shook my head. "Soon. But I think you’ll pay better attention if I keep you naked while I give you your instructions." It was really entertaining watching him. I knew he so wanted to at least cover himself with his hands, but he knew I wouldn't allow it. He was fidgeting restlessly, shifting his weight from foot to foot, and twitching his hips. It was so cute!

I ran my fingertips slowly along his waist. “I’ll let you have your clothes back soon, but in return, you’re going to do a few little things for me.”

"O-Okay," said Blondie timidly.

"First of all, I don't like looking at this unsightly hair. It ruins the effect. When I caress your legs, I want them to feel smooth. And soft. So, starting tonight, you’re going to shave your legs and keep them silky smooth for me.” He flinched at that, and I couldn’t help but smile. He was already dreading it, and we were only getting started.

“And I want you to wear shorts to school from now on,” I added. “That way, I won’t have to pull your pants down every time I want to enjoy your pretty legs.” Blondie’s eyes widened at the thought of parading his smooth, bare legs for everyone to see, day after day. "Though I have to admit, I do like undressing you." I smiled, savoring his blushing face.

“Now, say it back to me. What are you going to do when you get home—and what will you wear to school?”

"I... I'm going to shave my legs and wear shorts to school," he mumbled.

“All the time,” I reminded him, brushing my fingers lightly along his thigh. “Say it: ‘I’m going to keep my legs nice and pretty for you all the time.’”

He hesitated, but knew resistance was useless. “I’m g-going to keep my legs... nice and pretty for you all the time,” he repeated in a strained little voice. That earned some fresh laughter from the onlookers.

I wasn’t done. I reached down and took a pinch of the hair around his penis, giving it a little tug. “This has to go, too. I want you smooth all over.” I let my hand explore further down, my fingers tickling his scrotum. Blondie stiffened and scrunched up his toes. I've mentioned before how quite often the subtleties that occur during a humiliation session can be so enjoyable. Every reaction—the twitch, the shiver, the way the eyes squeeze shut—adds deliciously to the scene. I tickled him a little longer, just to prolong the moment.

"Your little balls need to be smooth too, okay Blondie?"

"Okay," he squeaked out in a high-pitched, defeated voice.

“Let me see your arm,” I said, gently lowering his right wrist from behind his head. I traced my fingers along his forearm, noting the fine blond hairs there. “You’re starting to get a little fuzz here, too. You’ll keep your arms nice and hairless for me—soft and girly. And you’ll wear short-sleeved shirts so we can admire them properly.” I tucked his arm back and peeked beneath it. “Mmm, underarm hair’s coming back. That’ll have to go, too. Keep your underarms smooth and bare, like a little boy." I walked behind him and stroked his buttocks, giving him a couple of playful taps. "Still smooth as a babe back here," I teased, and the crowd giggled along.

"Okay, let’s recap," I said, turning to face him again, hands on my hips. "No unsightly hair from the neck down. As for your underpants—you're going back to tighty-whities. No more boxer shorts. You haven’t earned that privilege. You’ve got little boy bits, and starting tonight they'll be smooth and completely hairless, just like the rest of you. You'll look like a prepubescent 10-year-old boy down there, with your bald little bits, so those childish undies will suit you perfectly."

“I... I don't have them anymore," Blondie said, his voice rising in pitch. "I threw them all away."

Oh, sweet naïve Blondie. Like that was going to deter me.

"Well, you'll just have to go buy a new supply after school, won't you?"

His mouth opened and closed helplessly. I fixed him with a look. "Let's see if you were paying attention. Why are you no longer allowed to wear boxer shorts?" I just love doing that to my victims. I know they hate it, and their humiliation intensifies with every word.

He stared at his feet, his face a shade of red only Blondie can produce. I was highly aroused, watching him standing there all naked and fidgeting. I would have had my hand inside my panties if I wasn't in public.

“Because... because I haven’t earned it,” he finally managed.

“Exactly!” I beamed. “Such a smart boy. And why haven't you earned it?”

He winced. "Because I... because... I haven't matured enough?" I loved how he put it in the form of a question.

“Very good! And in what way, exactly, haven’t you matured?” He just stared, so I helped him along, letting my gaze drop deliberately to his exposed crotch. "Is it because you have little boy bits?" The laughter from behind me continued mercilessly. Oh, the humiliation was intense, and I was having so much fun!

“Yes,” he whispered.

"Say it."

“I have little boy bits,” he said, his voice trembling, earning yet more laughter.

“Yes, you do! Now, after tonight, what will be a distinct—and very embarrassing—feature of those little boy bits?”

“They... I’ll... they’ll have no hair.”

"Right! You'll have bald little boy bits!" I paused dramatically, letting the crowd eat it up. “Let me hear you say it.”

"I'll have bald little... bald little bits."

"You'll have bald little boy bits." I looked him in the eyes, waiting.

He swallowed and obeyed. “I’ll have bald little boy bits.”

"And what will that look like down there? Do you remember?"

He closed his eyes, surrendering. “A 10-year-old boy.”

“Close. You forgot a word.” He looked at me, somewhat puzzled. "Prepu...?" I encouraged. I held out an open palm, gesturing for him to finish.

"Prepubescent."

"Good boy! Now say the whole sentence."

He drew a shaky breath. "I'll look like a... like a prepubescent 10-year-old boy... down there."

"With your bald little boy bits," I pushed.

"With my bald little boy bits."

"The whole sentence now."

He winced, then pushed it out: "I'll look like a... like a pre... a prepubescent 10-year-old boy down there with my little... with my bald little boy bits."

I gave him a delighted grin. "Yes you will, Blondie, and I can't wait for you to show off your new look for me!"

"Okay now, let’s see, what else?" I stepped close, letting my fingers brush the top of his thigh. "As for your shorts, I don’t care what kind, but the hem needs to be above mid-thigh." I tapped a spot just below where his boxers had been. “Gym shorts might work, but if they’re too long, I’ll just take them away and you’ll be prancing around in your new tighty-whities instead. Understood?” He nodded miserably, biting his lip. “Good boy. Legs like yours deserve to be on display—the more of your silky-smooth skin showing, the better. Oh, and lose the socks. I want those pretty legs flaunted from top to bottom, every inch of them."

I ran a line up his arm, marking a spot three-quarters up his bicep. “Shirtsleeves can’t go lower than this. I’d put you in a tank top if I could—but sadly, Roosevelt won't allow it.” I gave his arm an affectionate little stroke. “Honestly, you’d look adorable in short shorts and a tank top. Maybe for the weekend,” I added, winking.

Suddenly, Becky stepped forward, eyes twinkling. “I can help with the clothes, Felicity, if you want,” she offered. “Blondie’s about my size.” She traced a line embarrassingly high on his thigh, and he recoiled instinctively from his sister's touch. “I’ve got some cute shorts that hit right about here. I’ll leave them on his bed tonight. I’ll have him try them on after he shaves his legs,” she added, shooting Blondie a wicked grin. Blondie looked like he wanted to vomit.

Becky wasn’t finished. She pressed her finger to a spot on his upper arm, just under the shoulder. “And I’ve got a few tees that hit here. Should I dig those out too?”

“Yes, that would be perfect! Thanks, Beck!” I clapped my hands with glee. Turning to Blondie, I gave him a dazzling smile. "Now you can just wear whatever Becky picks out for you. Aren't you glad you have such a generous, caring sister? Not many boys get to share their sister’s wardrobe. What a lucky boy you are, Blondie!" Blondie didn’t respond—he just stared miserably at the ground in front of him.

I was already picturing him: legs silky smooth, arms bare, swishing through the halls in Becky’s snug shorts and feminine tees, blushing at every giggle, every lingering glance. The anticipation was positively intoxicating.

It was just about time to wrap things up, but I had one last surprise. I wanted to throw something Brenda’s way.

“Okay, sweetie, you can put your arms down now,” I told him. He dropped them instantly, hands flying to cover himself as he stared at me with wide, worried eyes—widening further when he saw I’d scooped up all his clothes. Without a word, I strode to his locker, stuffed everything in, and snapped the door shut with a satisfying click. The lock hung there, key still in place.

Oh, Blondie. Leaving your key like that? That was just careless.

I snapped the lock shut, slipped the key free, and sauntered over to Brenda. With a wink, I dropped the key into her waiting palm. Blondie's fate was now in her hands. Brenda's face broke into a wide, delighted grin as she strutted off down the hallway, holding the key high for all to see.

"No! Brenda!" Blondie cried, his voice breaking into sheer panic.

“If you want your clothes back,” I singsonged, “you'd better not lose her.”

I didn't have to tell him twice. The hall erupted as Blondie—naked and frantic—bolted after Brenda, hands cupped desperately over himself, weaving through the crowd as laughter, shrieks, and cell phones chased after him.

Brenda glanced back, grinned, and slipped into the girls’ bathroom. Blondie skidded to a stop. He hesitated for the barest moment—then, to the crowd’s giddy delight, he shoved the door open and vanished into forbidden territory. I heard shrieks of astonishment, followed by a wave of raucous laughter. I grinned, savoring the mental image of what had to be a riotous scene inside those walls.

* * * * * *

The last I saw of Blondie that day was a flash of his cute little butt disappearing into the girls’ bathroom—a fitting finale if ever there was one.

That evening, my phone buzzed with a call from Brenda. She was still giggling so hard it took her a minute to speak. “Felicity, I owe you big time for today.”

Between fits of laughter, she gave me the play-by-play: Blondie did get his key back, but he had to earn it. Brenda had perched herself on the sink, key dangling in the air, goading him into joining her. And Blondie—naked and desperate—indeed climbed up with her. But the instant he reached for the key, she let it drop. It ricocheted off the tiles, took a wild little bounce, and, as luck would have it, landed inside one of the bathroom stalls. Of course, it was occupied.

Brenda was nearly breathless from laughter. “He actually dropped to all fours to grab it, and the girl inside completely lost her mind—screaming and kicking at him like she thought some crazed pervert had crawled into her stall. Felicity, I was dying. I swear, I thought I was going to pee my panties. I haven’t laughed that hard in forever.”

I laughed along with her, wiping tears from my eyes. “Thanks for the update, Brenda. That really made my night.”

After we hung up, I lay back on my bed with a dreamy sigh. What a wondrous day—reuniting with Blondie, reasserting my control over him, and thoroughly humiliating him. So many delicious possibilities ahead, and I couldn’t, for the life of me, wait to explore them all. I was going to have sooo much fun with my Blondie.
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The Felicity Chronicles: My Exploits as a Humiliator, Chapter 13

Post by Blondie »

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Chapter 13: Johnny Boy: A Gradual Stripping Throughout the Schoolyard

A few days had passed since our last delightful little encounter with Johnny Boy. As much fun as it had been, something had been gnawing at me ever since. I’d given his friend Bobby explicit instructions to be under the tree at lunch, every single day. Yet the last time we showed up, Bobby was nowhere in sight. One thing I simply do not tolerate is disobedience. Bobby needed to learn that, and I was determined to teach him exactly how non-negotiable my rules were.

Andrea, Kayla, Natalie and I had just finished our lunch in the cafeteria. I was feeling frisky, and Bobby’s little act of rebellion gave me the perfect excuse to go on the hunt for a new humiliation victim. Not that I ever needed an excuse. :D

"What say we visit our favorite tree?" I asked with a playful grin.

My girls perked right up; they knew exactly what I meant. "Let's do it!" said Andrea as the four of us rose in unison.

"I'm sure," I mused as we stepped into the warm afternoon air, "that Johnny Boy reminded Bobby what's expected of him. The question is whether Bobby actually listened."

"He'd better have, for his sake," giggled Kayla.

As we approached the tree, I felt a flicker of disappointment—Johnny was there, but there was no Bobby in sight. But my spirits lifted the moment I saw the look of terror on Johnny's face. My mood lifted further when he scrambled upright, hands flying instinctively to his belt buckle.

"Johnny Boy," I said, sounding annoyed, "I'm quite disappointed you don't have Bobby with you."

“I—I...” he stammered, his cheeks already pink.

“Did you remind Bobby he’s supposed to be here during lunch? Every day?”

“Y-Yes, I did. But...”

"Did you tell him that because he wasn't here last time, we made you march around this very tree in your tighty-whities?"

He blushed a nice shade of red at the recollection. "I told him," said Johnny bashfully.

"And what did he say?"

"Well..." Johnny didn't want to go on, clearly reluctant to tattle.

"Tell me," I pressed, stepping closer. "I want his exact words."

Johnny's shoulders sagged. "Okay. He—he said he wasn't afraid of you. That you couldn't tell us what to do."

"Did he, now," I said with raised eyebrows. "Tell me, Johnny Boy—where can we find Bobby right now?"

Johnny remained silent. Admirably, he didn't want to give up his friend, especially after I coaxed him into telling me what he had said.

“Okay, here’s the deal, Johnny Boy,” I continued. “You’re going to tell me where you think Bobby is right now. Meanwhile, we'll hold your pants as collateral. If Bobby is where you say, you’ll get them back. If not...?" I paused for effect. "Well, you’ll have to forfeit something else. We’ll keep going until either we find Bobby, or you’re entirely out of clothes.” I watched his wide-eyed, open-mouthed expression with delight.

I turned to my eager companions. "Girls, help Johnny Boy out of those pants, please."

They descended like wolves on a wounded deer. Without prompting, they yanked off his shoes and socks first and had Johnny barefoot and trouserless in half a minute flat. Already blushing furiously, he yanked downward on his tee shirt—enough, I noticed, to cover nearly all of his tighty-whities. Clever boy. Maybe he was thinking ahead when he got dressed that morning. (giggle)

"Now, Johnny Boy," I said, savoring his discomfort, "I'm going to ask you again, and for your sake you'd better think very carefully before you answer. Where do you think we can find Bobby?"

Um... he likes sports. You could try the basketball courts," he offered, eyes darting everywhere nervously, fingers still clutching his shirt hem.

"You mean we could try the basketball courts,” I corrected. “You’re coming with us.”

"Oh, gosh! Can't—can't I just stay here? I promise I won't... I won't put my pants on until you find Robert—er, Bobby," he pleaded.

"I don't think so. You're our insurance policy, Johnny Boy. Someone is going to be naked today, and if we don't find Bobby, then that someone will be you. Now let's go. You lead the way."

The now petrified Johnny bent to retrieve his trousers. "Uh, uh, uh!" I clucked. "Those stay here. When we find Bobby I'll let you come back for your pants. Let’s go, Johnny. Time’s wasting.” I reached down, fingers brushing his perineum through the thin cotton of his underpants, delighting in the high-pitched yelp that escaped him, the way he lurched forward.

He cast one last mournful glance at his abandoned trousers, then set off toward the basketball courts while we trailed behind him. He walked briskly, stretching that tee shirt downward with every step, desperate for coverage. Heads turned as we passed by—some giggled, some just stared—but every reaction added to the delicious spectacle.

The courts came into view. Empty. No Bobby.

“I don’t see Bobby,” I said innocently. “Do you see Bobby, Johnny?”

“No... he’s not here,” he said, trying not to panic. “Maybe he’s playing tetherball?” He started toward the tetherball courts until my voice stopped him cold.

"Hold it!" I called out. "Not so fast, Johnny Boy. What did I say would happen if Bobby wasn't where you claimed?"

He froze. A few nearby students had noticed the scene unfolding and were watching closely.

“Answer me, Johnny Boy.”

"But—but I wasn't sure. Can we just see if he's playing tetherball?

"Yes we can, Johnny. But first you need to do something for me. What are you going to do for me, Johnny?"

His voice barely rose above a whisper. "You said... I'd have to take something off."

“Indeed I did.” I folded my arms, watching him stand transfixed, paralyzed by indecision. "Well?"

After another hesitation—I swear he was actually considering taking off his underpants instead of the shirt—Johnny finally, reluctantly reached behind his head, dragged the tee upward, and slipped it off. I loved how he stood there all embarrassed, clutching the shirt to his chest like a shield.

"Leave your shirt here, Johnny Boy," I said. "If we find Bobby you can come back for it." He scanned the area helplessly, searching for rescue that wouldn't come. "Just drop it on the ground. Nobody's going to steal your shirt." Still he hesitated, eyes sweeping for any sign of Bobby. It wasn't to be. “Just drop it,” I encouraged. “It'll still be here if you earn the right to come back for it."

Finally, he let it slide from his fingers and flutter to the ground at his bare feet. Once again I had Johnny Boy stripped to his underpants. Deliciously, he stood there all red-faced with his shoulders all scrunched up, with one hand over his chest (like a girl!) and the other over the tiny bulge in his underpants. If I wasn't out in public I would have started diddling myself right on the spot.

“You look so cute in your tighty-whities,” I cooed, giving one of his bright red cheeks a friendly little tweak. "Now-off to the tetherball courts in pursuit of our elusive Bobby." I gave his butt a playful squeeze. “After you, kind sir.”

There was giggling all around as Johnny’s ever-growing fan club followed along behind us. I was secretly hoping Bobby wouldn’t show up at all, such was the fun I was having with Johnny Boy. Watching him traipse in front of us in his underpants was just delectable.

We rounded the corner, and the tetherball courts came into view. But more importantly, Bobby did not. Johnny stopped in his tracks. He turned and looked at me pleadingly. It was really cute. “I think he’s at the soccer field,” he said quickly. “He really loves soccer!”

“That’s great, Johnny. I really hope you’re right,” I said.

He turned toward the soccer field, but I caught his waistband, halting him mid-step. "Aren't you forgetting something, Johnny Boy?" Of course he was aware of what I was referring to. I'm sure the prospect of stripping naked absolutely horrified him.

He pretended not to hear. His desperation was so palpable I could taste it. "Really," he said anxiously. "I think he's there. Let's go see."

I stepped closer, snuggling up to him. I took hold of his wrists and gently pulled them to his sides. I placed my hands on his shoulders, meeting his frightened gaze, then deliberately pressed my pubis into his. "We'll go see, Johnny Boy," I said to him in a soft, soothing voice. "But before we do there's something else I want to see." I dropped my hands and slowly, tantalizingly strummed his sides with my fingers on the way down, and he shivered deliciously.

"But—I think he's there!" Johnny tried again, desperation mounting.

"There, there, Johnny Boy," I cooed, slipping my fingers beneath his waistband. I put my hands fully inside and caressed his baby-smooth bum all over. "Don't worry, everything's going to be okay. We'll just get these undies off, and then we'll go find Bobby." My hand delved further into his underpants, and I stroked his perineum. Johnny flinched and wanted to pull away, but I held him in place.

"Oh! No! Please stop!"

I withdrew my hands and lightly tickled his belly with my fingertips, watching his stomach muscles tense reflexively. "I'm really looking forward to seeing you naked, Johnny Boy."

He flinched again. “Please, no! Don’t make me—”

"Shh, it's alright," I whispered. “No one’s going to laugh at you... well, perhaps a little. But that’s part of the fun, isn’t it?”

"No! Please! I can't!" His breathing grew rapid, shallow. I found myself hoping he wouldn't hyperventilate.

"Can't what, Johnny?" I asked, stroking the insides of his thighs, stopping just short of his underpants. His knees bowed outward in response. "Why are you so afraid to be naked?"

He swallowed hard, voice trembling. "I-I don't want everyone to see."

"What don't you want them to see, Johnny Boy?"

"Please..."

"Tell me, Johnny."

"It's... not very big, and there's no..." His voice trailed off.

"No hair? Are you bald down there, Johnny Boy?"

Johnny, whose face couldn't be any redder, nodded.

"Well, perhaps everyone doesn't have to see. But I'd like to see. Would it be okay if I have a peek inside?"

"No! Please don't!"

"You're not defying me, are you, Johnny? Because if you are then you'll have to be punished."

"No! No, I'm not—I'm not defying you!"

"Okay, good, then no punishment. Now ask me politely to peek inside your underpants."

"Oh! Um... will you... will you peek inside... inside my underpants?"

"Say please."

"Please." I looked at him sternly. He tried again, voice cracking. "Please will you peek inside my underpants?"

"Of course, Johnny Boy. Thank you for asking. I'd love to see."

I really love doing this. I remember peeking into Blondie's underpants—actually, they were panties—that night on my thirteenth birthday. He wrote about it, and I could tell how humiliating it was for him. In his account he even commented on how my hair tickled his stomach. The memory made me smile.

I leaned forward, making sure my hair brushed Johnny's belly, teasing him with the sensation. I pulled his underpants outward, peered inside, and started giggling. I mean, I couldn't help it! Maybe it was because he was so frightened, but he was even smaller than I'd anticipated—smaller than Blondie, even. And as expected, he was bald as an egg down there. I looked up to him, grinning. He looked ready to faint from embarrassment.

"I understand now why you don't want everyone seeing this, Johnny Boy," I said, my voice warm with mock sympathy. "That would be awfully embarrassing for you."

I wanted to throw a bone to my cohorts, who had been so helpful. "Everyone doesn't have to see, Johnny. But my friends might want to." I glanced back at Andrea, Natalie, and Kayla, who hovered close by. "Girls, do you want take a peek inside Johnny's underpants?"

"Yes!" they said, almost in unison.

At the same moment, Johnny wailed, "No!"

"They want to see too, Johnny. I know it will be hard for you, but they will really enjoy this. Thank you, Johnny," I said as I patted his tummy. "Girls, you really need to see this," I invited, stepping aside.

Andrea surged forward eagerly. Without hesitation, she tugged open Johnny's waistband and peered inside, and like me she immediately started giggling. "How cute!" she said, while ceding to Natalie.

When Natalie finished her inspection, she cupped his flushed cheek in her palm and said, "Poor thing."

Kayla performed the final examination, smirked, then turned to the gathered crowd and called out, "Move along, folks. Nothing to see here." Uproarious laughter erupted.

I sidled back up to the utterly humiliated Johnny and slipped my fingers beneath his waistband. "These need to come off, Johnny Boy. You know that, don't you?"

He was trembling now, eyes darting toward the two dozen or so spectators hanging on every moment. I was afraid he might have a panic attack, so I felt I needed to ease his anxiety, if ever so slightly. I was going to take his underpants off, because that was part of the deal we made—and truth be told, I really wanted to. Besides, relenting now would undermine my authority entirely, and that simply wasn't an option.

I did make one concession, though. "Here's what I'll do for you, Johnny Boy. Since you've been so obedient, I won't expose your hairless baby boy bits to everyone out there. But you must keep your hands by your side and not resist when I take down your undies. Andrea, Natalie, and Kayla will form a semi-circle around you for privacy. Some of the kids will probably go behind you to check out your bare bottom, but they won't be able to see how tiny your baby boy bits are, or how bald you are down there."

"But... but the four of you will see?" God, he was so innocent, so helpless, and I was absolutely savoring every second.

"Yes, Johnny, the four of us will see. We want to see you naked—completely exposed. We looked inside your underpants, but it's not the same as seeing you naked. But if you're a good boy, no one else will see your wee bits. It'll be our little secret. Kayla will photograph everything for later enjoyment, but as long as you obey, only the four of us will see. Okay, Johnny?"

"Oh, gosh. Oh gosh. Oh gosh. Oh!... okay." His breathing remained rapid and shallow.

I gestured for the girls to form a wall around the soon-to-be-naked Johnny. "Good boy, Johnny. Everything will be fine, you'll see. Soon you'll be nice and naked, and only the four of us will see your bald baby boy bits." I paused, momentarily enjoying the recollection of the last time I had a blushing victim standing naked before me.

"You know, I have another boy I enjoy playing with, much like you. I'd love for you to meet him someday. His name is Blondie. I've stripped him naked before, just as I'll be stripping you naked momentarily. His bits are on the small side, and I call them 'little boy bits.' But—and lucky you—yours are even smaller. So, since yours are smaller, I think it's only fitting to call yours 'baby boy bits.' Or, better still, 'Johnny Boy's bald baby boy bits.' Can I hear you say it?"

He blinked, caught completely off guard. "Oh! Um... J-Johnny Boy's b-bald baby boy bits."

"Gooood!" I giggled. "Now let's get you out of these underpants so you can be nice and naked for us. I haven't seen you naked yet, and I'm genuinely looking forward to it. Are you ready Johnny?"

“Oh gosh!” was all he could manage. His chest heaved with rapid, shallow breaths, his stomach doing the same with each anxious exhale.

"It'll be okay, Johnny Boy," I said, in as soothing a voice as I could muster. "I promise I'll be gentle. Take a nice, deep breath. Just keep your hands at your sides, no sudden movements, and I'll simply pull these down, juuuuuust like this," I said, slowly drawing his underpants to his ankles. The tiny whimper escaping him as I did the deed was absolutely precious.

"See, that wasn't so terrible, was it?" I said, knowing full well it was excruciating. "Step out of these, Johnny Boy," I instructed, holding them at his feet. "Then you'll be completely naked, just like we said."

Johnny let out a few soft, high-pitched yelps as he stepped free, one trembling foot then the other. I tossed the underpants aside, and there he stood—utterly nude in the middle of the schoolyard, red as a tomato, shaking, looking like he might collapse.

The four of us broke into uncontrollable giggles, staring down at his exposed genitals. I couldn't have made a better choice when I picked Johnny out. Oh, the poor boy! Again, the fear and humiliation likely contributed, but his penis was so tiny that, lacking weight, it jutted straight outward like a turtle's head poking from its shell. His little balls remained tightly wrapped in their sack, tucked beneath his penis. And he was as hairless as the day he was born. Gawd, the humiliation he must have been feeling is mind-boggling!

"Can we see?" shouted a female student from several yards away.

I turned, smiling. "Sorry," I called back. "Johnny Boy is very shy and needs his privacy right now." Grinning, I held up my hand, separating thumb and forefinger by about an inch. "He's a little sensitive," I added, much to everyone's hilarity.

"I simply must touch these," Kayla announced, reaching down to fondle his balls. "Ooh, check it out, girls," she crowed. "They're adorable, and so smooth."

Much to Johnny's torment, we each took turns exploring his testicles. Kayla was right—their smoothness was exquisite. I went last, finishing by grasping his penis. I looked up at Johnny, whose misery was profound, as one would expect. "I'll bet this looks even cuter when you get a little hard-on. How much bigger does it get when you're excited, Johnny Boy?"

Johnny could barely speak. "I—I don't know," he squeaked.

"Well, that'll be something we can explore another day. Right now, we need to go find Bobby," I said. "I'll keep my promise—you can cover up now, Johnny." Johnny eyed his discarded underpants. "No, silly," I laughed. "With your hands. You can retrieve your underpants if we find Bobby."

Johnny clenched both hands tightly over his crotch and led us toward the soccer field. Most of his audience followed, with newcomers joining along the way. The four of us laughed heartily, thoroughly enjoying our fabulous humiliation session. It was genuinely amusing watching naked Johnny stride briskly ahead, his little buttocks jiggling with each step.

As we neared the soccer field, lo and behold, Bobby appeared in the distance. Johnny, despite himself, lifted one hand from his genitals and pointed excitedly.

"There he is!" he exclaimed, turning to me with wide, hopeful eyes.

"Okay, Johnny Boy," I laughed. "I guess it's your lucky day. You may go. Thank you for your help—and the entertainment."

Johnny bolted like a bat from hell, racing for his clothes. Rather than detour for his underpants, he made a beeline straight for the tree and his trousers. I gathered the underpants and stuffed them into my backpack, suspecting they might prove useful later.

My attention shifted fully to Bobby. Bobby was on my shit list. He disobeyed me, and I was eager to make him pay. He had absolutely no idea what virtual tsunami was about to crash over him. We'd given Johnny Boy a rough time, but at least he got his clothes back.
Last edited by Blondie on Fri May 15, 2026 5:31 am, edited 4 times in total.
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