The Felicity Chronicles: My Exploits as a Humiliator, Chapter 14
Posted: Thu Feb 29, 2024 6:39 am

Chapter 14: Bobby: Clothes Cut Away
After amusingly watching the naked Johnny scamper away and disappear around the corner, I set my sights on Bobby. At the moment he was on the soccer field, dribbling away from a defender. His shock of longish blond hair bounced up and down as he skillfully performed his maneuvers.
Bobby's fun and games were about to be rudely interrupted.
He spotted the four of us walking purposefully toward him when we were about twenty yards away. He hesitated for a moment, then concluded that it probably wouldn't be in his best interest to hang around and wait for us. He took off running in the opposite direction, toward the nearby baseball field. Without my prompting Kayla, Natalie and Andrea took off in chase. I continued to walk briskly, my confidence in my cohorts resolute.
Bobby was pretty fast, but I could see that Kayla and Natalie were closing the gap. Andrea brought up the rear, but her determination was steadfast.
Bobby had reached shallow center field when he was tackled from behind by the speedy Kayla. Natalie was only a couple of steps behind, and by the time Andrea arrived on the scene they had him somewhat subdued. I say "somewhat" because Bobby was quite feisty—he wasn't going down easily. He was kicking and clawing like a caged animal, but it was apparent that he would be no match for the three girls.
"Get off of me, you bitches!" he screamed. "Get the fuck off me!"
When he saw me approaching he turned his escape attempts up a notch and managed to catch Kayla with an elbow to her chin. She did not take the blow good-naturedly. In an instant, she had his arm twisted behind his back, forcing it into a position that looked excruciating.
“Ow! Ow! Stop! Please, let go, goddammit!”
“Are you going to be a good boy?” Kayla asked, applying just a little more pressure.
“Ow! Oh shit! Yes! Let go!”
"Say please," she purred.
"Please! Oh, fuck! Stop!"
Kayla relaxed her hold, but she wasn’t letting go. Natalie had his other arm, just in case he decided to make a run for it again. I stood in front of him, calm and collected.
“Bobby, it’s so nice to finally catch up with you,” I said, my tone cheerful. He didn’t answer—he just glared. “We stopped by the tree earlier. You weren’t there. What do you have to say for yourself, Bobby?"
“My name is Robert,” he snapped. “And I wanted to play soccer. Is that a crime?”
"It's not a crime. But it's a choice you made that won't go unpunished," I answered. "When I ask you to do something, I fully expect that you'll do it. You got your friend Johnny in trouble with your indiscretion. Now it's your turn."
I crouched and began untying his shoes.
"Hey! What do you think you're doing!" he yelled while pulling his leg away from me.
Kayla twisted his arm behind his back again, this time even harder. He bent over and tried to break loose, but Kayla and Natalie held him in check.
"Owww! Son of a bitch! Stop!"
“Are you going to stand still like a good boy?” Kayla asked.
“Yes! Shit! Okay!”
Kayla eased up and I continued where I left off. After untying his shoe, I proceeded to unthread the shoelace from his tennis shoe and pull the lace completely off the shoe.
“Wh—what are you doing down there?” Bobby asked, clearly getting nervous.
“Helping you learn a little lesson,” I said casually.
I untied his other shoe and unthreaded the shoelace as before. I then reached into my backpack and pulled out a medium-sized pair of scissors. Holding the laces up together, I called on Andrea.
“Can you hold these ends taut for me?” I asked.
She stretched the shoelaces taut while I snipped them in half. Then again. And once more for good measure. Four shredded ends fluttered to the ground like confetti.
"What the...?" said the bewildered Bobby.
I wasn’t finished. I grabbed the tongue of his shoe and snipped it clean off.
"Hey! You've ruined my shoe, you bitch!" shouted the incredulous Bobby.
I cut off the other tongue and looked up at Bobby, who was fuming. I smiled sweetly.
“And now I’ve ruined the other one.”
I peeled off his shoes and tossed them aside. I focused on his socks. He was wearing a pair of cargo shorts, so they were quite accessible. Starting from the top I cut into his olive-colored sock until reaching his toes, then pulled it off before repeating the maneuver with his other sock.
“Goddammit, knock it off!” Bobby roared, his face flushed with rage.
I stood up and eyed his shirt. A quirky little Henley-style number with buttons all the way down. That wouldn’t last long.
"I was quite disappointed, and a bit surprised that you weren't with Johnny at the tree today," I said, snipping the bottom button clean off. We both watched the button pop slightly outward and fall harmlessly at his feet.
"What the fuck are you doing?!" screamed Bobby. "That's my shirt!" He made a feeble attempt to break free, but everyone—including Bobby—knew he wasn’t going anywhere.
"You really should have been there, Bobby," I said calmly while cutting away two more buttons.
"Goddammit, you're ruining my shirt!" he fumed, practically shaking with anger.
Unfazed, I gripped the fabric and cut a full circle around his torso.
“Andrea, could you pull this tight for me?” She did, and I sliced the strip in half. Then again. After slicing once more, I took the small, shredded pieces and tossed them up in the air, watching them flutter leisurely to the earth.
“How cute,” I grinned, running my hands around his bare tummy. "Now you're wearing a crop top."
“Okay, okay, you’ve had your fun,” Bobby said, clearly rattled. “Now let me the hell go!”
"I don't think so," I answered. "I don't think you've learned your lesson yet." I moved behind him and reached into his right front pocket.
"Hey!" he said as he squirmed in reaction to the intrusion. "Get your hand—what are you doing?!"
Out came three dollar bills, a quarter, and a dime. I stuffed the cash into his back pocket, then yanked the emptied pocket inside-out.
"You're not to wear front pockets in your shorts anymore," I said as I cut it off and tossed it aside.
"Son of a bitch! You're fucking crazy!" Bobby barked, eyes wide.
I reached into the other pocket and pulled out a key. Into the back pocket it went. "Crazy or not, I'm deadly serious. When you get home I'd like you to gather all your shorts and pants and cut the front pockets off, just like this," I instructed as I pulled out his left pocket and snipped it off.
"No fucking way!" was his response.
I calmly walked behind him, grabbed a handful of his hair that had reached his upper back—about an inch's worth, maybe a tad more—and snipped it off.
"What're you....hey, what the fuck!" he screamed incredulously.
I opened my palm, showing him the clump of hair before I let it flutter to the ground. "I'll keep going if I have to. It's entirely up to you, Bobby," I said.
"No! Okay I'll do it!" he conceded.
“Do what, Bobby?” I asked, raising an eyebrow.
"I'll cut the fucking pockets off my shorts!" he blurted, breathless and flustered.
“And your pants?”
"Yes! Goddammit, just let me go!" He pulled against the hold on his arms and Kayla gave another firm twist. "Ow! Fuck!" he said as he again gave up on his struggles.
"That's a good boy, Bobby," I said, my voice syrupy sweet. I reached into the gap where his right front pocket used to be and hooked a finger into the side of his underwear, tugging the dark blue boxer briefs out through the opening.
“Also—no more underpants. Ever.”
His eyes went wide as I cut away the material. I sliced up from the bottom, straight through the soft material and clean across the elastic waistband.
“Jesus Christ!” Bobby yelped. He turned a panicked look toward Andrea. “Is she insane?!”
"Oh, Bobby, you have no idea," replied the grinning Andrea. "I wouldn't test her if I were you."
"If I ever catch you wearing underpants, I'll simply do this again," I said calmly as I repeated the same maneuver on his left side. "But if I do, I'll be sure to give you a nice haircut while I'm at it," I said as I looked up at his lengthy locks. “And if you think I’m bluffing, then you haven’t been paying attention.”
I reached for his zipper and slid it down.
"Hey!" he shrieked. "Get your hands—what're you doing?!"
Without answering, I reached in and pulled on his boxer briefs through the fly, and with minimal effort they came through the hole and completely off.
"May I?" offered the grinning Andrea, right on cue.
She stretched out the material while I snipped through the middle. Two cuts later and the small bits of what used to be Bobby's underpants were scattered on the ground, unrecognizable.
Bobby, somewhat shocked by the proceedings, was speechless, at least temporarily.
I handed the scissors to Andrea and looked Bobby square in the eye.
"So this is what I expect from you from now on: no front pockets and no undies. That way I'll always be free to do this," I said as I moved behind him, sliding my right hand into the newly formed opening at his right hip until I found his penis.
"AGHHH!" said the startled Bobby, ever so eloquently. (giggle)
"Not bad, Bobby boy," I said as I felt around, sizing him up. Indeed, Bobby's penis seemed like at least a normal size—maybe even a little bigger than normal. It was definitely bigger than Johnny's or Blondie's. And I could tell that Bobby had started growing some pubic hair. I remember making a mental note to possibly have the three of them stripped together sometime so I could compare—and most assuredly make fun of Johnny's and Blondie's smaller penises.
I slid my left hand through the other side and took hold of his balls. Bobby squirmed, but Kayla's firm grip kept him in place. I continued to play with his penis while fondling his balls. I grinned as his penis began to respond.
"Oh, Bobby, I'm so happy to see that you like me," I teased.
"Please...please stop," he pleaded softly.
But I continued my manipulation until I determined that he was completely erect. I guessed it was at least five inches long, with decent width—pretty good for a young fourteen-year-old whose onset of puberty was probably fairly recent.
I pulled my hands out and moved over to face him, savoring the blush on his cheeks as our eyes met. We both knew that I had just had my way with his genitals, something I was pretty sure no one other than himself had done before. That glazed look in his eyes told me everything—he was mine. Subdued through humiliation, completely under my control. And it felt incredible.
"I'm going to let Kayla and Natalie let go of your arms now, Bobby," I said. "You'd better not try to run away. If you do, when we catch you—and I think you know that we will catch you—I'll have the girls hold you down while I give you a free haircut. I don't think you would want that, because I'm really not a very good hair stylist."
I nodded to Kayla and Natalie, who then released their grips. Bobby winced and stretched his sore arms. At least two dozen people had gathered, captivated by the unfolding spectacle. He scanned their faces, clearly panicked, but he made no motion to try to run away.
I looked down at his crotch and noticed that the tent that had formed from his erection was beginning to diminish. I thought it would be fun to have Kayla rectify that.
"Kayla, could you do me a favor and reach into Bobby's front pockets and describe what you find?" I asked while retaking possession of the scissors from Andrea.
The grinning Kayla wasted no time. From behind, she smoothly slid both of her hands inside Bobby's shorts. I could tell from his wide-eyed expression that she had found pay dirt.
"Oh yeah," said Kayla. "There's definitely a penis here. And it's a pretty good size."
While Kayla talked, I smiled at Bobby while snipping off the last three buttons of what remained of his shirt.
"And it's a very active one at that," continued Kayla. "The more I play with it, the bigger it gets."
I cut Bobby's shirt on both sleeves up to his neck and pulled it the rest of the way off. Andrea and I quickly cut the material into small pieces.
"And he has nice balls,” said Kayla. "They fit perfectly my hand. I'm stroking them now. They're pretty smooth, maybe a little bit of hair. Oh, and he's definitely got a full-fledged hard-on now," declared Kayla.
"How long do you think it is?" I asked.
I crouched beside him, scissors in hand, and began cutting up the outside seam of his right shorts leg—slow, deliberate, inch by inch. I stopped just shy of the waistband, leaving a slim sliver of fabric still connecting the pieces. All the exposed skin was becoming a turn-on for me as I anticipated the end result.
"Oh, let's see," said Kayla. "I'd guess somewhere around five inches. Possibly more. And there's some girth. Pretty good for a young white boy," said Kayla, laughing at her intentional stereotyping.
"I think we need a second opinion," said an anxious Andrea, who proceeded to step up and put her hand through the zipper hole. The startled Bobby tried to draw backwards but was inhibited by the exploring Kayla. He probably would have jumped out of his shoes if he was wearing any. At this point both girls had their hands on Bobby's extended member.
"I agree," said Andrea. "Probably at least five inches. Hard to be sure, though. What do you think, Natalie?"
Andrea pulled her hand out and the grinning Natalie eagerly shoved her hand inside Bobby's shorts. "Hmm," said Natalie as she felt around while the beleaguered Bobby squirmed deliciously. "It could be more than five inches. Does anybody have a ruler?"
While all that was happening, I’d already started slicing up the other side of Bobby’s shorts—once again stopping just shy of cutting them clean off.
That’s when Bobby realized what I was doing.
“No! Please! Everyone, stop! Oh, please, let me at least keep my shorts!” he begged, voice cracking.
Aww. Sweet desperation.
* * * * * *
I've gone on a little long, so I think I’ll pause the story here. But don’t worry—there’s plenty more to come. Next I have a fun story to tell you about an impromptu outing I had with Blondie. I’ll post that as soon as I get it written up.
But rest assured, we’ll return to Bobby. Since you probably know me pretty well by now, I don't think it's a spoiler to say that we indeed got him naked. That's where Kayla got her moment to shine. She really put him through his paces.
I can’t wait to tell you all about it.