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

Post by Blondie »

The following is applicable to all chapters of “The Felicity Chronicles: My Exploits as a Humiliator”

© December 2017 by Blondie.

This is a work of fiction and is pure fantasy. Names, characters, places and incidents are products of the author's imagination and are used fictitiously. Any resemblance to actual events or locales or persons, living or dead, is entirely coincidental.

For ages 18 and older only.

Chapter 1: Evolution of a Humiliator
Chapter 2: My First Experience in Humiliation, Part 1 of 4
Chapter 3: My First Experience in Humiliation, Part 2 of 4
Chapter 4: Johnny Boy: Procuring My Victim
Chapter 5: My First Experience in Humiliation, Part 3 of 4
Chapter 6: Johnny Boy: Homeroom Humiliation
Chapter 7: My First Experience in Humiliation, Part 4 of 4
Chapter 8: Johnny Boy: Stripped to Underpants
Chapter 9: Ruby: Spanked in the Bathroom (ENF)
Chapter 10: Tina: Forced to Pose Topless (ENF)
Chapter 11: Johnny Boy: Marching in Tighty-Whities
Chapter 12: Blondie: Naked in the Roosevelt Hallway
Chapter 13: Johnny Boy: A Gradual Stripping Throughout the Schoolyard
Chapter 14: Bobby: Clothes Cut Away
Chapter 15: Blondie: Driving in Tighty-Whities
Chapter 16: Blondie: Humiliated by the Catholic Girls
Chapter 17: Bobby: The Naked Doggie
Chapter 18: Blondie: Cafeteria Humiliation
Chapter 19: Ruby and Tina: A Spanking, and Small Breast Humiliation (ENF)
Chapter 20: Blondie: Forced to Strip Naked for his Sister
Chapter 21: Johnny Boy: An Unwelcome Erection Exposed
Chapter 22: Blondie and Johnny Boy, Part 1 of 4
Chapter 23: Blondie and Johnny Boy, Part 2 of 4
Chapter 24: Blondie and Johnny Boy, Part 3 of 4
Chapter 25: Blondie and Johnny Boy, Part 4 of 4
Chapter 26: Blondie, Johnny Boy, Bobby, Tina and Ruby, Part 1 of 3
Chapter 27: Blondie, Johnny Boy, Bobby, Tina and Ruby, Part 2 of 3
Chapter 28: Blondie, Johnny Boy, Bobby, Tina and Ruby, Part 3 of 3

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Felicity Chronicles, Chapter 1: Evolution of a Humiliator

Hi, my name is Felicity. I'm only seventeen years old, but in my not-so-humble opinion, I have had enough interesting experiences already to justify putting pen to paper. If you’ve ever found yourself intrigued—maybe even a little stimulated—by the fine art of humiliation, then I have a feeling these chronicles might be right up your alley.

To say I have a “fondness” for humiliation—specifically, me being the one to dish it out—would be like saying the sun is mildly warm. Nothing excites me more than having a blushing, squirming victim completely at my mercy.

Most often I like to have my victims remove some or all of their clothing. I do find that quite effective. I haven't met anyone yet who isn't embarrassed to the extreme by having to strip (or be stripped) against their will. And when they’re already red-faced and vulnerable, that’s when teasing becomes an art form.

I've also noticed—and I don't think this will surprise anyone—that when others are present, their level of embarrassment is more acute. And then, when they're naked and I make them do things... ohhh, don't get me started. I can tell already that I'm going to get excited just by writing about these tales.

You probably noticed that in my title I used the word "humiliator." Some might suggest "humiliatrix" is more fitting. My older sister Julie has told me more than once, after watching me in action, that I could make a ton of money as a professional humiliatrix. She tells me that there are many people out there—male and female alike—who enjoy having humiliation inflicted on them by a dominatrix, and that they pay a lot of cold, hard cash for the experience.

I'll assume my sister is right, but I can tell you that it would never be something for me. I mean, think about it—if they pay to have humiliation enforced on them, then that means they actually want it. The whole thrill for me is taking someone who absolutely, positively doesn’t want to be humiliated—and of course, most of us fall into that category—and making it happen anyway. And I can assure you that all my victims would rather be anywhere else than under my thumb.

So no, I’m not a humiliatrix. I’m a humiliator, through and through.

My first actual experience as a humiliator occurred on my thirteenth birthday, and my victim was a boy named Blondie. Yes, Blondie. I mean, seriously, how could I not pounce on a boy with a name like that? He was sixteen, cute, adorably shy, and already deeply entangled in a web of humiliation, thanks to his sister Becky and a few of her friends.

Anyway, it was an amazing experience, and I'll tell you a little about it later. I have to say he has always been my favorite, and I have taken advantage of my control over him on many occasions. I'm looking forward to telling you all about it.

But even before Blondie, I’d had inklings that I was... well, different. I knew I had this unusual inclination toward humiliation well before that. I think my sister Julie had a pretty good idea, too, because she is the one that helped set me up with Blondie as a birthday present. To this day, that by far has been the best birthday ever!

But I digress. I mentioned that I had an inkling about my humiliation tendencies. I vividly remember reading a book at a young age—I want to say I was eight or nine—where a boy went skinny-dipping, only for his friends to run off with his clothes. They were laughing at him as he covered himself while begging them to give his clothes back. I remember getting a tingly feeling all over, and even at that young age I put my hand inside my underpants and fondled myself as I read it over and over. I don't think I had an orgasm, but I do know that it felt really, really good, and it was my first memory of being turned on sexually.

Then there was the time in the park with my mom—I think I was 10—and these high school guys were ganging up on someone, trying to depants him. They’d already yanked his pants down to his knees, and his shirt had ridden up, so I could see his underpants. Gosh, I remember it as if it happened yesterday. Anyway, he was screaming bloody murder and my mom yelled at them, but that didn't deter them at all. Finally, she gave up. Thinking she was protecting me, she grabbed my arm to whisk me away. I fought her tooth and nail because I really was hoping to see the kid get stripped, but my mom would have none of it. So when I got home I locked myself in my room and started playing with myself again, while imagining the kid getting stripped completely naked.

I fondly remember hearing many juicy stories over the course of a few months when I was twelve. Julie had observed how precocious I was, and she knew I had an appetite for this kind of thing. She started confiding in me more than ever.

I first heard about Blondie from her. She and her friends had somehow gained control over him. I didn't know how, and I really didn't care. Just knowing that he was at their mercy was good enough for me. Anyway, as the story goes, Becky and her friend Brenda had lured him into Victoria’s Secret, and Julie, who worked there, joined the fun. They somehow got him to hand over his clothes, piece by piece, until he was naked behind a dressing room door. She got to see him naked and even made him walk out into the store wearing a teddy, and later just a bra and panties. And at one point he had to run out there naked to grab something to wear. It was a humiliator's dream.

Now that was so much better than the skinny-dipping incident I had read about. Not only was it much more humiliating, but it was not a fictional character this time. Blondie was a real person, and my sister got to be involved in his whole humiliating ordeal!

As much as I was enjoying Julie's account of the incredible affair, I couldn't wait to get away to the privacy of my bedroom. When I did, I immediately tore off my clothes, jumped on my bed and feverishly masturbated while picturing everything Julie had just told me. I was a late bloomer and had not yet reached puberty, but I have no doubts that I had my first orgasm right then and there.

Subsequently I would often ask Julie to tell me more about this Blondie kid, and much to my delight there were several stories. I think my favorite was when Julie's friend Marcia, along with a guy named Mitch, made Blondie slowly get naked in the dark auditorium during a school play. They even made him shine a flashlight on his penis. Julie told me, with a wicked little grin, that it was rather small. That just made the story even better. And Julie said he didn't have any hair back then, even though he was fourteen years old. Can you imagine how embarrassed he must have been?

Anyway, I guess Marcia started playing with his balls, and this guy Mitch started fondling his penis. Then he made Blondie put his hand inside Mitch's pants and forced him to start stroking his penis. Word was that Blondie and Mitch (with a little help from Marcia) got each other off—simultaneously! Can you imagine? Gosh, I would have paid big bucks to be in Marcia's place. But listening to Julie, I was able to put myself there with my vivid imagination. And, thanks to Julie, I was able to entertain myself to the point of several more orgasms, all at the tender young age of twelve.

And eventually, I didn’t have to imagine anymore. Julie set me up with Blondie for my birthday, and I had my first real taste of being a humiliator.

I'll tell you all about it in the next chapter.
Last edited by Blondie on Sat May 09, 2026 6:18 pm, edited 20 times in total.
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Re: The Felicity Chronicles: My Exploits as a Humiliator

Post by Robert Brooks »

Excellent! Great to see Felicity make her debut here, another favourite character of mine :D
Looking forward to revisiting this one over the forthcoming chapters.
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Re: The Felicity Chronicles: My Exploits as a Humiliator

Post by TeenFan »

The Felicity character is probably the most devious and deviant in these humiliation stories.
However, I'm hoping that after she is finished with rehashing the events with Blondie, that her next victim cannot be ridiculed for
"underdevelopment". Looking forward to the time when Felicity or a similar character uses a variety of tactics for teasing and humiliating
guys and gals of all ranges of physical development.

Just some wishful thinking on my part. I enjoy how these stories are presented and they do give me ideas I want to steal.
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Re: The Felicity Chronicles: My Exploits as a Humiliator

Post by Blondie »

Sorry to disappoint, TeenFan, but the next character to be introduced is indeed underdeveloped. As you know, I find that feature to be more humiliating for the victim(s). I understand that tastes vary in this regard and is not for everyone. I do enjoy writing in that characteristic, and I feel that my writing "juices" (not in the literal sense) are flowing better when I employ it.

There is one more male victim in this story (along with two that are female), who will be introduced down the road. His physical development is more normal, if not a little above average.
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Re: The Felicity Chronicles: My Exploits as a Humiliator

Post by TeenFan »

Blondie wrote: Wed Feb 14, 2024 10:25 pm There is one more male victim in this story (along with two that are female), who will be introduced down the road. His physical development is more normal, if not a little above average.
Nice, looking forward to it.
Of course I'm a big fan of taking the "Average" fella and feminizing him by either shaving or being made to wear girly clothes. I used that
in a story where during a game of Dares, my main character had to switch some clothing with another, leaving him wearing only panties.
Of course the guy was well endowed and could barely keep himself contained in the tight panties, so the character is very self-conscious of that
and very nervous for the rest of the game. As you said, different strokes for different folks.
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Re: The Felicity Chronicles: My Exploits as a Humiliator

Post by Hammer »

Are you going to be adding the Miss Joplin parts that used to be in the Felicity Chronicles?
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Re: The Felicity Chronicles: My Exploits as a Humiliator

Post by Blondie »

Hammer wrote: Thu Feb 15, 2024 12:09 am Are you going to be adding the Miss Joplin parts that used to be in the Felicity Chronicles?
Yes, as you probably know, the Miss Joplin chapters turned into a story of its own. It is ongoing; I think I have five or six chapters done. I will post that in the ENF section as time permits.

Sorry it is taking me awhile to get these stories posted. I have to reformat, then proofread them, so it's a tad cumbersome. But I will get them up!
Last edited by Blondie on Thu Feb 15, 2024 4:41 pm, edited 1 time in total.
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The Felicity Chronicles: My Exploits as a Humiliator, Chapter 2

Post by Blondie »

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Chapter 2: Blondie: My First Experience in Humiliation, Part 1

I'll never forget the moment. It was late afternoon on the day of my thirteenth birthday. As I told you in my introduction, Julie had told me that a few of her friends had taken control of a 16-year-old boy named Blondie. She told me several very stimulating stories of the different ways they had humiliated the poor guy. Each time I pictured myself in the scene, and each time I became sexually aroused. I yearned for the chance to be in the thick of it—watching him squirm, blush, and obey. The more I heard, the more I ached for a chance to join in.

And finally, that day had come. I was stretched out on my bed with a book when it happened. Julie knocked on my door, and I remember every second of what followed.

“Feel like going out tonight?” she asked, standing in the doorway with a devious smile on her face.

Even though it was my birthday, sadly I had no plans. Our parents were out of town at some business symposium related to their joint business. They put Julie in charge, and in retrospect, I'm so glad they did. “Sure,” I said, curious. “What’s up?”

Julie flopped onto my bed. "Brenda just called. She and a few others are at Becky’s place and invited me over. I thought you might want to tag along.” That didn't really interest me very much. Until she continued. “Apparently, they're having a little fun with Blondie. Sounds like they’ve got him dolled up in a girl’s nightgown right now, making him parade around.”

I shot up off my bed like a jackrabbit, my book tumbling to the floor. “Are you serious?! Tell me you’re not joking!”

Julie burst out laughing. “Okay, then. I’ll take that as a ‘yes.’”

“Oh my God, Julie, this is fantastic!” I grabbed her arm and practically dragged her toward the door. "Let's go!" I said excitedly.

“Whoa, whoa, slow down!” Julie laughed. She glanced at my bare feet. “You might want to put on some shoes first. And I need to grab a little something from my room.”

Julie disappeared and returned with a baby blue little girl's party dress in one hand, and an oversized nylon bag in the other. Later I’d learn there was a fluffy white petticoat tucked inside. She held the dress up and stretched it out. It was really short, with a flared skirt and short puffy sleeves. "I've been saving this for just the right occasion. Maybe we can get Blondie out of his nightgown and have him model this for us."

I actually clapped my hands and jumped up and down. “Oh, Julie, that would be amazing! Do you really think we can make him do that?” I was short of breath with excitement.

Julie chuckled. "I just might be able to pull that off for you, sweetie."

A wicked impulse popped up. “Can we get him naked too? Like, completely naked?” I asked eagerly.

Julie burst out laughing. “Listen to you! I didn’t know you had such a deliciously mean streak.”

I grinned. “I guess I do. Oh, I can’t wait!”

She stuffed the dress, petticoat, and a handful of mysterious items into her Victoria’s Secret bag. “All right, let’s go have a little birthday fun.”

My anticipation level in the car was so high I was afraid I might pee my panties. When we pulled in front of the house, my heart was racing a mile a minute. It was a feeling I've had many times over the last few years—pretty much every time I'm preparing to humiliate one of my victims—but I guess because this was my first real taste, none quite matched up to my eagerness to engage with Blondie.

And let me tell you—it did not disappoint. The moment we stepped inside, I was met with a vision so sweet it nearly stopped my heart. There he was—Blondie, a blushing sixteen-year-old boy who looked even younger. A long, pink, sleeveless nightgown fluttered around his ankles, and my gaze couldn’t help but linger on his arms: smooth, pale, and utterly bare of hair. The delicate skin looked freshly shaven, and I doubted very much it had been his decision—which only made the sight all the more thrilling.

The girls had him stationed in the middle of the room, clearly putting him through his paces. He looked so embarrassed, so helpless and—much to my delight—wickedly adorable in his misery.

I couldn't wait to be introduced, and even more eager to play a part in that incredible scene.

* * * * * *

Here’s where I’ll take a little detour. I could fill pages with every delicious detail, but there’s no need. Blondie himself chronicled the whole ordeal online—yes, really! Apparently, he thought putting it all down in words would help him process what we did to him. Poor boy. He poured out his soul in an embarrassingly raw account, never guessing his sister Becky would find the file and, gleefully, share it with the world on "Pantsing and Stripping Forums," a stimulating humiliation site with a lot of talented writers. It's right up my alley.

I've read his account many times, and yes, often to the accompaniment of sexual gratification. It’s become a bit of a guilty pleasure.

So instead of recounting everything myself, I’ll include some of my favorite excerpts from his own writing, with a bit of commentary from yours truly. I hope you enjoy it.

Then came Julie—the salesgirl from Victoria’s Secret. I noticed the girl seated next to her and immediately felt a fresh wave of unease. She looked like she was about eleven or twelve years old. Being paraded like this was bad enough, but somehow being humiliated in front of a much younger girl made everything feel significantly worse.

He wasn’t wrong—I’ve always looked a couple years younger than I am. And I could tell it made him even more uncomfortable. I think the idea of being shamed in front of someone who looked like a kid made it all feel even more demeaning. Realizing that added to my level of enthusiasm.

Becky turned my attention to the salesgirl. “I know you remember Julie,” she said. How could I not? That infamous mall visit left an indelible impression on me.
“Good evening, Blondie,” Julie said with a smile, extending her hand. “So nice to see you again. I must say, you’ve taken to girls’ clothes quite nicely! I don’t recognize this piece, though—have you been shopping somewhere other than my store?”
I fumbled for an answer. “Uh, I think this is Becky’s,” I responded weakly.
Julie gave a playful shrug. “No worries. I brought some fresh samples for you to try on.” She motioned to a “VS” tote bag by her feet. “Maybe later you can model some of them for us.”


I remember the way he looked at that Victoria’s Secret bag earlier—his eyes widened, and his jaw dropped. He probably had a pretty good idea that it was for him. When Julie finally confirmed it, he looked a bit frightened. It was delightful.

“Blondie, meet my sister, Felicity. Felicity, this is the famous Blondie.”
“Nice to meet you,” I forced out as I shook her hand.


That was the first of many times I physically touched him. His handshake was weak—well, let's face it, he was under duress. No eye contact, either. It was adorable. His submissiveness was unmistakable, and honestly, it was kind of a turn-on.

“No, it really is my pleasure, Blondie,” she said. “My sister’s told me all about you, and I’ve just been dying to meet you.” I sensed a degree of precocity in the girl that put me on edge. I had a sinking feeling this girl would be trouble.

Oh, Blondie. (giggle) You had no idea. Well, you did. But I’d bet it still turned out far worse—and far more humiliating—than you imagined.

“Wish her a happy birthday,” Becky chirped.
“Happy birthday,” I said, not even trying to sound enthusiastic.
“Why thank you, Blondie. You’re such a sweetheart,” Felicity said. I remember thinking, once again, that this girl really was going to be trouble.


Yes, I guess he was getting to know me. Some people say "trouble" is my middle name.

Brenda interceded, and it was to my detriment. “Why don’t you tell us all what you’re wearing under your nightgown, sweetheart.”
I knew better than to challenge Brenda. There were a few moments of silence, as I had considerable trouble vocalizing the word. “P-panties,” I finally said, very softly.
“I’m sorry, what was that? Speak up, dear, so we can all hear you,” Brenda said.
“Panties!” I screamed out, almost defiantly. Laughter was abounding.
Joanna pounced on the moment. “What color are they, Princess?”
I fidgeted nervously. “Pink,” I mumbled.
“Ooh, how darling," teased Joanna. "Do you like wearing your pretty pink panties? Hm? Do they make you excited?” She tried to reach for my penis, but I pulled her hand away. Everyone was laughing, rollicking at Joanna’s taunting. “Well, do you, Princess? Do you get off on wearing your sissy panties?”


It was almost getting to be too much for me to handle. I wanted to rip that nightgown right off and see exactly how cute he looked in just his panties—and watch him turn redder than ever. But I kept my cool, hard as it was. I had a feeling if I just stayed patient, I’d be rewarded. As it turned out, my patience paid off—in spades.

As I got up from the couch I felt a pinch on my rear end. I brushed Joanna’s hand away, catching a glimpse of her devilish grin as I did.
“Felicity, would you like to join us?” Julie asked.


Oh my goodness, was that music to my ears, or what? I was going to be part of the main event! I was literally trembling with excitement.

The salesgirl and her precocious little sister giggled heartily as they led me to Becky's bedroom, where further humiliation undoubtedly loomed.

I'll never forget the feeling as we walked down that hallway. The wicked glee—the sheer, delicious anticipation—was off the charts.

* * * * * *

Whew. I’m getting a little worked up just reliving it all. I think I’ll stop here for now, but don’t worry—I’ll definitely be picking this story back up soon. I have so much more to tell.
Last edited by Blondie on Sat May 09, 2026 9:47 pm, edited 6 times in total.
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The Felicity Chronicles: My Exploits as a Humiliator, Chapter 3

Post by Blondie »

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Chapter 3: Blondie: My First Experience in Humiliation, Part 2 of 4

I last left you when Julie and I escorted Blondie into the bedroom. It was my first opportunity to play an active role in someone’s humiliation, and I was absolutely tingling with anticipation. I’ll continue with Blondie’s account.

Felicity lingered in front of me, grinning broadly, drinking in every second of my discomfort.
“Is this where we get to make Blondie get naked?” she asked, eyes glued to my mortified face.


Notice how he mentioned that my eyes were glued to his face while talking about getting him naked.? I'm so glad he noticed, and I knew he would. Yes, I really did want to get him naked—and I eventually would—but I think I had just as much fun watching him squirm as I teased him with the idea.

“Ah, here we go—he’ll look just divine in this,” and pulled out a little girl’s party dress. She held it up. It was baby blue, with a short, flared skirt and short, puffy sleeves. My eyes widened, my mouth dropped open, and horror flooded through me.
“Oh please,” I pleaded. My body language spoke volumes as I folded my arms across my chest and slumped my shoulders. “I can’t wear that out there. Please...”


I really did love watching his body language as he imagined himself wearing that little girl's dress. There’s something magical about watching someone process their own humiliation in real time. As soon as he glimpsed that dress, he flushed from pink to crimson, and I caught myself grinning even wider.

“Felicity, would you like to help Blondie out of his nightie so we can get him ready?” She studied us closely—one of us in utter anguish, the other practically glowing with delight.
“You betcha!” squealed Felicity, her eyes twinkling with mischief as she grabbed the nightgown’s spaghetti straps and slid them off my shoulders.


At the time, I was thinking, "Did she really just ask me if I would like to get Blondie out of his nightie?" Would I like to personally strip a boy for the very first time? I might have been salivating.

“I got this,” Felicity cut in confidently, wagging her finger in my face. “Okay, Blondie—either you lower your arms and cooperate right now, or I’ll call the girls in here and the seven of us will strip off your nightgown, pull down your panties, and take turns putting you over our knees for a spanking you’ll never forget. Then you’ll model your pretty new party dress for us anyway. So it’s your choice: You can play nice and make it easy, or be difficult and earn yourself a humiliating spanking. Either way”—she pointed at the dress—“you’ll be wearing that by the time we’re done. Now... which way would you like it?”
The precocious little thing was a monster.


And the precocious monster was having the time of her life. I thought I laid the law down quite well there, and, in case there was any doubt, he knew who had the upper hand.

She gently slid the straps off my shoulders and stepped back to watch the natural descent of the nightgown as it pooled around my ankles. Her fingertips flew to her lips as she squealed with delighted disbelief at the sight of me—smooth legs and all, trembling, and wearing nothing but a pair of pink panties.

That was a vision that will be etched in my brain forever: the nightgown slipping down and exposing his pale, hairless legs, while he stood there in a pair of pink panties, his hands over his crotch in abject embarrassment. God, it was so delectable. I could’ve stared for hours.

“Well, well, what have we here?” Julie asked rhetorically, approaching with a devilish grin. Until then, she’d been just a very interested spectator—now she was ready to join in. Kneeling, she lifted my feet one at a time, freeing me from the nightgown. “My, my, look at these pretty legs,” she said, brushing her fingers up my calf in a slow, lingering stroke. “Felicity, come feel how smooth Blondie’s legs are.”
Of course, the little fiend needed no second invitation. “Ooh, you’re right, Julie,” she cooed, caressing my other leg. “So smooth and pretty—like silk.” I wanted to die on the spot.
Julie rose and ran her hands over the seat of my panties, eyes gleaming with mischief. “And such darling panties, too. Do you like your panties, Blondie?” she teased. I stayed silent, head down, staring miserably at the floor. Raising her arms, she interlaced her fingers behind her head, elbows wide. “Go like this, Blondie. I want to see something.” I hesitated, but I knew there was no use resisting. I complied. Julie giggled. “Just as I thought—not a hair anywhere,” she said, inspecting my smooth underarms.


Gosh, were we tormenting him so. Obviously it would be embarrassing enough to have two girls ogling him in a pair of panties that he was forced to wear. But teenage boys are really proud when they finally grow their body hair. For Blondie, having to stand there, displaying his total hairlessness to us, must’ve been torture. And I was eating it up.

Also—and I’m not entirely sure why—I found it rather titillating to run my hands over his bare, silky-smooth legs, especially with him standing there utterly mortified, fully aware that we were both amused by how smooth he was.


“I wanna see, I wanna see!” Felicity chimed in gleefully, sounding like an eight-year-old determined to get her way. I instinctively drew back my hips as she reached for the elastic—the idea the thirteen-year-old inspecting my most private parts against my will was just too much. “Blondie?” she warned with an admonishing look. I straightened up and reluctantly submitted to the mischievous sprite. Eyes squeezed shut, I braced myself as the elastic stretched away again. Her hair tickled my stomach as she leaned in. Though my eyes stayed closed, the image of her staring down my panties burned in my mind.
After what felt like an agonizing eternity, the elastic snapped back into place.
“Well, little sister?” Julie asked, clearly enjoying the show.
Felicity beamed. “It looks just like Joey’s, except Joey has no hair.”
Julie laughed boisterously and approached me, locking eyes as she spoke. “In case you’re wondering, Blondie, Joey’s our little brother. He’s ten.” Both girls burst into uproarious laughter while I blushed crimson.


Peeking inside his panties was one of my all-time favorite moments. I knew how much he hated me staring at his little goodies for the very first time. Blondie didn't reference it in his account, but I made sure to giggle while I was staring, which I'm sure added to his shame. I know he heard it, and that made it all the sweeter.

Actually, the giggling was genuine. The vision of a 16-year-old's little penis that compared to my 10-year-old brother's was pretty amusing. And the fact that he knew that I found it amusing was stimulating for me. There were a couple of different times that I figured I had seen enough and was ready to pull away, but I purposely drew out the moment longer. Oh, how excruciating that must have been for him!


“I assume it’s supposed to get bigger as boys get older. Right, Blondie?” Felicity directed the question at me, but I didn’t answer. She knew she’d struck a nerve and milked it for all it was worth. “How old are you, Blondie?” she pressed, staring me down until I gave in, hoping to speed the interaction to a conclusion.
“Sixteen,” I whispered, averting my eyes.
“Well, except for the hair, you look like you’re ten, judging by what’s inside your panties.” Both girls laughed again as I turned yet another shade of red.


And he really did turn another shade of red when I teased him. It amazes me (and delights me!) to this day that I have the power to make Blondie blush brighter, no matter how red he might already be at the time. I really know how to push his buttons.

Little girls can’t expect to wear their party dress without their petticoat,” Julie cooed, pinching my cheek before handing the garment to her sister. “Felicity, darling, would you like to do the honors?”
“Oh, yes please!” Felicity replied gleefully. She lifted it over my head and tugged it down, adjusting the shoulder straps and fluffing out the skirt. She stepped back and looked me up and down. “Oh my gosh! You must come see, Blondie!” She grabbed my hand and led me to the full-length mirror.


In this case, it was almost as much fun dressing him as it was stripping him down. He knew he was going to have to go out there looking like that and face everyone eventually. The wretched expression on his face added to my enjoyment.

The petticoat made an audible swish-swish as I walked, adding to my mortification. Julie patted the mattress, gesturing for me to sit. I did, and instantly regretted it as the skirt shot up high, prompting another delighted squeal from Felicity. She ducked down, trying to peek underneath. Mortified, I clamped my knees together and pressed the petticoat down with both hands—realizing to my disgust I had just done exactly what a little girl would’ve done. Felicity noticed. “What’s the matter, Blondie?” she teased. “Don’t want me to see your panties?”

Yet another delightful moment among many, watching him flinch and squeeze his legs together when I tried to peek under his petticoat. It makes me grin just thinking about it.

Felicity was all too happy to comply. I felt a flush of embarrassment as she knelt and reached up my dress—oh my God, I just called it MY dress—I mean THE dress—and in one swift motion pulled the panties down to my ankles. I flinched at the invasion, and again when she slipped beneath the petticoat to peek. She looked up, grinning, while I burned red with shame.

Like I said, I love making him blush, and I'm very good at it. In this case, all I had to do was look at him and smile after seeing his little penis again.

“Alright, that does it—I’ve had just about enough of you, young lady!” Julie snapped, pretending to be truly upset. Looking back, I’m pretty sure she was just hunting for an excuse to spank me. She reached over to the dresser and grabbed a hairbrush. “Pull up her petticoat, Felicity.”
“No, please!” I yelped in protest, but Felicity was already behind me, grinning as she flipped the fluffy white layers upward.
“Pull down her panties,” Julie ordered.
“No! Nooo!” I pleaded, but my protests only seemed to egg them on. Felicity yanked the panties down to my knees and held the petticoat pressed against my back. I knew resisting any longer would only make things worse. Before I could even catch my breath—Whap! Whap! Whap! Whap! Whap! Whap! Six sharp blows from the back of the hairbrush smacked against my bare ass, three on each cheek. The pain took a moment to register, but when it did... man, I’m here to tell you that it throbbed furiously.
“Ow! Ow! Ow! Ow!” I squealed, hopping in place while cradling my butt cheeks with both hands. The girls burst into peals of laughter. I must have looked completely ridiculous—bouncing up and down with frilly panties hanging at my knees, and the petticoat and dress bobbing up and down.


It was fun pulling his panties down again, and it really was hilarious watching him jump up and down like that in the little girl's dress. And, though Julie got to administer the discipline, it was quite enjoyable to be involved in my first spanking. Fortunately, it wouldn't be my last, and the day would come when I would have the pleasure of handing out a spanking on my own.

Julie took one hand, Felicity the other, and this time I didn’t resist as they led me down the hallway in my wretchedness. When we entered the living room—well, I’m sure you can imagine the uproar. The shrieks of surprise and delight were almost deafening.

I really enjoyed the reaction from all of Julie's friends and felt very proud of myself for having a lot to do with it. I knew Blondie wanted to just dig a hole and climb in. Wonderful stuff, and the best was yet to come.

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

And this precocious, demonic girl can't wait to tell you all about it.
Last edited by Blondie on Sat May 09, 2026 10:39 pm, edited 6 times in total.
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The Felicity Chronicles: My Exploits as a Humiliator, Chapter 4

Post by Blondie »

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Chapter 4: Johnny Boy: Procuring My Victim

After my first taste as a humiliator, I knew I was hooked. I craved my next opportunity, like a junkie needing a fix. Blondie would always be there—the video footage from that night ensured his submission whenever I wanted. But as delicious as that was, I found myself hungry for fresh prey. Variety, after all, is the spice of life.

I'll circle back to my thirteenth birthday adventures with Blondie later, but for now, let me take a little detour and share how I secured a new victim—one who would provide me with endless entertainment throughout my high school years.

It was my freshman year at Roosevelt High, and I had just turned thirteen, making me the youngest student at the school. I had skipped the fourth grade, thanks to a mutual decision by my parents and third-grade teacher that I wasn't challenged enough at my grade level.

I found myself constantly checking out the other students, sizing up potential victims. I’d scan the halls and classrooms, imagining what it would be like to have control over this one or that one—and I would always imagine them naked and cowering before me.

I've always been the type to plan ahead, and I knew that finding a fellow freshman to humiliate would be perfect—I could have fun with him for the full four years. Blondie was a senior, so I only had the one year with him at Roosevelt. Of course, there would always be opportunities outside of school, both during and after that year, so there was that.

I was primarily focused on boys, though I wouldn’t turn down a girl if the right one came along. I wanted a boy who was behind schedule, so to speak, in the puberty department. One who looked young, innocent, and preferably late to develop. Maybe I had that proclivity because Blondie was my first—he was sixteen and had reached puberty, but his late bloomer status (confirmed by my sister) and tiny penis made him seem so much younger after I divested him of his pubic hair—I mean, he looked like a prepubescent boy. I'm making myself grin as I summon up the vision of his denuded body, and how mortified he was to have me see him that way.

Picking an underdeveloped boy had another advantage—their humiliation was greatly enhanced when I exposed their childlike privates. Boys that age are incredibly self-conscious about their bodies, especially if they are late developers. Watching them squirm and seeing their red cheeks as I teased them about it was deliciously satisfying.

So, I wanted a late bloomer. Most of those boys were already fourteen, so pickings were slim, but there were a few potential candidates. Out of a handful of possibilities, one in particular caught my eye. His name was John. He sat right in front of me in both homeroom and morning algebra class. He was taller than me, slender, with a youngish face, somewhat feminine features, and he had that innocent vibe I was looking for. Unlike Blondie, he had dark hair. Not much arm hair—probably not much anywhere else, either. I found myself frequently wondering about the rest of his body and was hoping to see it for myself someday.

The challenge, of course, was figuring out how to get him under my control. I was on the petite side, looking more like eleven than thirteen, so I didn't exactly present an intimidating figure. I needed help, and who better to turn to than my sister Julie? She'd always been there for me, and after the recent adventure with Blondie, she completely understood my humiliation tendencies. If needed, she could call in Becky, Brenda, and the others for backup. Plus, she was a student at Roosevelt, making it easier to pull off whatever plan she came up with.

"Julie," I said one evening after deciding to go for it, "could I talk to you for a minute?"

“Sure, sis, what’s up?”

“Well, there’s this boy at school...” I began.

"Ah, do tell!" Julie teased. “Is little Felicity crushing on someone?”

"No—well, maybe, but not in the way you think." I paused, searching for the right words. "More like Blondie," I said.

Julie immediately got it. "Oh, you little devil, you," she replied, laughing. "One night of stripping and humiliating a boy, and you're hungry for more."

I actually blushed. “I know, right? I just need help getting him to, you know... obey me.”

Julie smiled. "Hmm," she said. "Let me think. We need to get this boy into a compromising position."

"Oh, I knew you'd understand, Julie!" I said excitedly.

"No problem, sis. And I'm sure we'll have fun doing it," she said.

"So... here's the thing. I know this is going to sound very selfish, but..."

“But you want him all to yourself,” Julie finished for me.

"Yes!" I exclaimed. "You totally get it! If you can get him in that compromising position you're talking about, and make sure he knows he has to do whatever I say—oh, Julie, I’d owe you forever.”

"Say no more. I know how much fun you had with Blondie, especially when we left you alone with him. Let me work on a plan, and I'll let you know. Just tell me who he is and what we’re working with.”

“His name’s John. Or, actually, I want to call him Johnny. No, wait—I want him to answer to 'Johnny Boy'." That got us both giggling. “He’s almost your height, slim, dark hair, cute face—kind of a pretty boy. Maybe besides stripping him I'll dress him up someday. You know, like we did with Blondie.”

"Listen to you," laughed Julie. "You don't even have him yet, and here you are making all these big plans for him."

“I can’t help it!” I said, unable to stop smiling. “Anyway, he sits in front of me in both homeroom and algebra. He always hangs out by the football field during lunch, glued to his phone under this big old tree. I don’t know where he lives, but after school, he rides his bike south along the main street.”

"You've been quite the stalker, haven't you," laughed Julie.

"I guess," I laughed. "Hopefully someday I'll be a lot more than that."

She ruffled my hair. “Leave it to me, sis. I’ll come up with a plan.”

“One more thing,” I said. "Whatever you do, can you do it without me being there? I kind of want our first meeting to be, you know, just us.”

"I get it," Julie said. “An intimate moment. One you and your Johnny Boy will never forget.”

I squeezed her in a hug. “You’re the best, Julie. I can't wait!”

* * * * *

A week later, Julie already had a plan. She’d met with Becky, Brenda, Marcia, Joanna, and Cheryl. All of them were still at Roosevelt, and they were more than happy to have a little fun with a fresh target—even if he was a couple years younger. I was sprawled on my bed, flipping through a homework assignment, when Julie knocked on my open door and walked in.

“It’s all set,” she said with a twinkle in her eye.

I knew exactly what she was referring to. The Johnny Boy matter had dominated my thoughts ever since we talked. I leapt off my bed and faced her with wide eyes, practically bouncing. “Tell me!” I said eagerly, almost nose to nose with her.

"Easy, girl, easy," Julie laughed, placing her hands on my shoulders and guiding me back a step. “So, we had a lunch meeting. We put our heads together—I have to say they were pretty enthusiastic when I told them what you wanted—and we came up with a plan."

"Go on," I urged impatiently when she hesitated.

She grinned devilishly. "It's pretty simple, really. The six of us, all at once, ambush him. I thought about asking Mitch to help, but once I got a good look at Johnny, I realized we didn’t need him. Heck, Brenda alone could put him in a headlock if necessary. So, we wait for him at lunch near that tree you mentioned. We surprise him, wrestle him down, and, well... let’s just say he ends up very embarrassed.”

My heart raced. “So you're going to—”

She nodded, eyes twinkling. “Pull down his pants, yes. Underwear too, obviously. Then we snap a few pictures. Becky’s on camera duty. Once we have what we need, we tell him who sent us—that would be you, of course—and make him agree to do anything you ask him to do. We'll tell him if he doesn't, then we'll post the pictures all over the school."

A thrill shot through me. “That’s—oh my god, Julie, I love it! I think it will work!"

Julie grinned. “Oh, it’ll work. And knowing you, after you’re through with him, he might actually wish we’d just posted the photos instead." Our laughter filled the room.

“So when?” I asked, barely able to contain myself.

"Tomorrow's as good a day as any," Julie said with a smile. "We were thinking lunch time, under the tree.”

"Perfect! Tomorrow it is, then," I answered with high anticipation.

* * * * * *

It took a significant amount of self-restraint, but I managed to avoid the event. I wanted my first glimpse of Johnny Boy’s humiliation to be face-to-face. Still, when I met up with Julie after lunch, I could hardly wait for the report.

"Well?" I yelled hopefully as I saw Julie approaching in the distance. Her response was a grin and a thumbs-up sign. I was elated. “Yes!” I cheered. “Tell me everything!”

Julie flashed a wicked smile. “He was exactly where you said—leaning against the tree, lost in his phone. We used the element of surprise. Brenda grabbed his arms, Marcia sat on his chest, and Joanna and Cheryl had his legs pinned. Becky was ready with the camera, so I went for his waistband. It was a piece of cake for me to get his pants down to his knees."”

My eyes widened. "His underpants, too, right?" I asked hopefully.

Julie smirked. “Both at once. He was fighting like crazy, but he didn’t stand a chance. Cheryl yanked his shirt up for good measure, exposing more skin. Becky got some great shots—face and all. If we need to use them—highly unlikely—we can crop the girls out.”

I was practically buzzing with excitement. "Oh my gosh, this is so awesome!"

Julie continued, savoring each detail. “While his pants were still down, I asked if he knew Felicity from class. He nodded, red as a beet. I told him you’d be reaching out, and that if he wanted to keep the photos between us, he'd better do anything you tell him to do. He didn’t say anything, so I added a little more to the equation. I told him that we could come back, and next time we'd strip him completely naked and run away with his clothes. That really got his attention," said Julie with a chuckle.

"Oh, I'll bet!" I laughed.

"Just to be sure, I said, 'Do you understand?' He said, 'Yes, I understand.' He also said something along the lines of, 'Can I please pull my pants up?' He was quite desperate to cover up—and there wasn't much to see, if you know what I mean," she said with a giggle. My eyes lit up at that juicy tidbit, a wicked grin spreading across my face. "You're really going to have a lot of fun with this one, sis," Julie said with a sly smile.

Just then, her phone buzzed. Julie looked at it and chuckled. “Becky just sent me one of the photos. Want a preview?”

As much as I did, again I showed self-restraint. "I'll get my chance," I said with a grin. "Just make sure he sees it."

“Oh, he will.” She tapped away on her phone. “Done.”

I hugged her, giddy. “Oh, Julie, thank you so much! I can’t wait!”

The bell interrupted us, and we parted ways. I'm not sure my feet hit the ground as I headed to my fifth period class.

* * * * * *

That evening, I couldn't concentrate on anything but Johnny. I imagined his face, his body, his humiliation. I even picked out my outfit for the next day, something cute but authoritative. I wanted to look innocent but dominant. I practiced my smile, and my commands. I was ready. I was going to own him completely.

* * * * *

The next morning, I slipped into homeroom at the last minute to ensure Johnny would be in his seat. As I strolled past his desk, I caught his eye and flashed him my sweetest, most dangerous smile. He flushed a delicious shade of red—and I knew this was the beginning of something special.

I took my seat behind him, unable to stop grinning as I looked forward to a very promising future with my Johnny Boy.
Last edited by Blondie on Sun May 10, 2026 1:27 am, edited 4 times in total.
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