Blondie's Humiliation Stories

For Age 18+ Only.
Chapter 16: Bobby
Mon Apr 16, 2018 3:08pm

"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. She smoothly slid both of her hands inside Bobby's shorts. I could tell from his wide-eyed expression that Kayla had found pay dirt.

"Oh yeah," said Kayla. "There's definitely something here." While Kayla talked I smiled at Bobby while snipping off the last three buttons of what remained of his shirt. "It's a penis, alright," continued Kayla. "And a very active one at that. The more I play with it, the bigger it gets." I cut Bobby's shirt at 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 definitely has two testicles," said Kayla. "They fit perfectly in the palm of my hand. I'm stroking his scrotum now. It's pretty smooth, maybe a little bit of hair." I turned back to Bobby and toyed with one of his nipples. "He's definitely got a full-fledged hard-on now," declared Kayla.

"How long do you think it is?" I asked. I bent down on one knee and, beginning at Bobby's right knee I started cutting straight up the seam of his shorts on the outside of his leg. I stopped when there was only about a quarter of an inch left that held his shorts up at the waist. 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. 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 them. At this point both girls had their hands on Bobby's extended member. "I agree," said Andrea. "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 looked like he wanted to cry. "It could be a little more than five inches, it could be a little less. Does anybody have a ruler?"

While this was going on I had already began cutting up the other side of Bobby's shorts, again stopping just short of cutting them off. Obviously quite distracted, he suddenly realized what I had done.

"No! Please! Everyone, stop! Oh, please, let me at least keep my shorts!" he begged.

"What's the matter, Bobby?" I said. "You don't really think I'd cut these off and leave you naked in the middle of the schoolyard in front of all these people, do you?" He seemed somewhat mollified, evidently thinking that I wouldn't dare do something so outrageous. Clearly he missed his buddy Johnny's naked jaunt a few minutes before.

I grabbed one end of his shorts close to the waist and gestured to my three buddies. They knew exactly what to do. Each of them took hold of the three corresponding remaining areas of his newly cut shorts. They looked expectantly at me for a sign. I used my fingers to count 1, 2 and 3. We simultaneously yanked his shorts in four different directions, and in the bat of an eye Bobby was rendered completely naked.

He was so stunned that it took him at least two full seconds to react, which was plenty of time for us to take in his raging hard-on that we had created. When he did react, he ended up in the absolute classic "forced naked in public" pose. He was bent over with his hands desperately clenched over his genitals, with a helpless, terrified expression on his face. I have referenced the "Stripping and Humiliation" website before. If you go to that site you will see on the main page a wonderful picture of an attractive woman who is naked in the middle of a street, obviously against her will. Bobby had the same pose and expression as the woman in that picture. Fortunately Kayla was quick with her camera and captured a fantastic picture of the moment. To this day I still delight in revisiting the picture, which has remained on my phone all this time.

While thoroughly enjoying Bobby's predicament, Andrea and I made quick work of slicing up the rest of his shorts. I saved the square patch of his back pocket that contained his minimal possessions for him. Very considerate of me, wouldn't you say? <giggle>

Meanwhile, the near-hysterical Bobby was beside himself, not sure of what to do. He looked around in desperation, first at what used to be his clothes scattered across the grass. They were completely useless to him. He looked around at us, then at his entertained audience, and realized that no help was forthcoming.

"Oh! Please! Anybody! I need some clothes! Oh, shit!" he shouted. Given the amused expressions on the faces of the spectators, I doubted that any of them were interested in altering the state of dress of their source of merriment.

I reached into my backpack and produced Johnny Boy's tighty-whities that we had procured earlier in the lunch hour. I spread them out with two hands and held them up for Bobby to see.

"Would you like to have these?" I asked. Given the circumstances, the meager offer was very attractive to the would-be recipient. The age-old adage "beggars can't be choosers" certainly applied.

"Yes! Please! Anything!" replied the frantic Bobby.

"Okay," I laughed. "But starting tomorrow you're not to wear underpants ever again. And before you get these you have to do something for me. I want a nice naked photo of you, but no covering up. Now stand up straight and put your hands on your head while Kayla takes some pictures."

Judging from Bobby's expression, the terms of my offer horrified him. He seemed to clench his privates harder and said, "Oh God, please! Can I just have them?"

I pulled out the scissors again and said to Andrea, "Pull these tight for me, Andrea, so I can cut them up."

"No!" screamed Bobby. "Okay, I'll do it!"

While Kayla readied her camera phone, Bobby, much to everyone's delight, slowly raised his hands to his head. His erection had subsided, but only about halfway, which somehow added humor to the state of affairs. Kayla snapped a couple of shots and Bobby, thinking she was finished, immediately covered up again. It was during the next sequence that I realized that Kayla might be even more depraved than I am––if that's possible. <giggle>

"I'll tell you when I'm finished, Bobby. Let's see your goodies again." Bobby reluctantly moved his hands to his sides. "Hands on hips, please. And stand up straight." When he obeyed Kayla continued with her photography session. "Good. Now turn around for me. I want a picture of your cute little white ass." Bobby shuffled his feet and turned himself around, providing everyone with a view they had not yet seen. "That a boy," cooed Kayla. Click. "Now reach down and grab your ankles." There was a long hesitation from Bobby. I was becoming more stimulated by the second while witnessing Kayla's administrations.

Bobby turned his head back and said, "Please, can I just...."

"Do you want to stay naked?" interrupted Kayla.

Defeated, Bobby bent over at the waist and held his ankles. "Good boy," said Kayla. "Now I'm getting some nice pictures of your pretty little butt hole. Hold that pose, let me get a close-up. Natalie, could you do me a favor and spread his cheeks a little wider for me?"

My, oh my, Kayla was on a roll and couldn't be stopped. I wasn't planning on going this far, but I certainly had no desire to rein her in. <giggle>

"Thanks, Natalie," continued Kayla. "Yes, keep holding them apart while I zoom in. Ah, perfect." Click. "Got it. Okay, Bobby, I want you to do one more thing for me, then you can have the underpants and we'll let you go. I'd like you to get down on your hands and knees and crawl around on the grass like a doggie for me."

I remember starting to get a little damp from stimulation right then. I swear I was getting more pleasure out of watching Kayla do her thing than when I was putting Bobby through his paces myself.

Bobby stood up and, unsure if he could handle any more humiliation, he just stood there with his hands over his crotch, staring at the ground. I was wondering if Kayla would be able to get Bobby to continue any further. I shouldn't have doubted her.

"Come on, Bobby, I'm getting impatient. You're going to be my naked doggie," insisted Kayla. Bobby stood still, unwilling––or possibly unable to do Kayla's bidding. "Do you want Felicity to give you a haircut?" she asked. They both looked over at me and I held up the scissors, opening and closing them a few times for effect. Kayla had pressed the right button. Bobby took a deep breath and dropped down to his hands and knees.

"Good boy!" said Kayla while patting Bobby on the head. "Now roll over." After a moment's hesitation, Bobby rolled over one time before returning back to all fours. "That's a good boy!" exclaimed Kayla. She had a small piece of candy at the ready and held it up to Bobby's mouth. I almost choked on my saliva from laughing as I watched Bobby open his mouth and accept the treat.

"Can you bark for me?"

"Arf!" said Bobby after another hesitation.

"I prefer 'woof'," said Kayla.

"Woof!" obeyed the miserable, crimson-faced Bobby.

"Thatta boy," said Kayla. "Now let's go for a walk." Kayla began walking away from us. "Here, boy!" she commanded while tapping the back of her thigh a couple of times. To the utter hilarity of all the onlookers, Bobby followed his master Kayla and crawled at her heels as she walked around in circles. "Faster, doggie!" she said as she picked up the pace to a slow trot. The laughter escalated as Bobby furiously scampered in circles to keep up with the devilish Kayla. Andrea videoed the hilarious scene, and the four of us have had several laughs over the years while viewing it together.

Finally Kayla stopped and turned to face her mortified victim. "Sit," she commanded. Bobby, out of breath, obediently sat on his haunches. He immediately covered his privates. "Good boy!" she said and fed him another piece of candy. "Now stand up," she commanded. As Bobby started to rise Kayla held him down by the shoulders. "On your knees," she whispered to him. Bobby soon was straightened up on his knees, his hands diligently covering his genitals. "Good boy," she said while patting him on the head again. She held her hands out to the sides of her shoulders, bending them limply from her wrists. "Now hold your paws out like this," she demonstrated. Bobby grudgingly spread his hands, putting himself on full display. Of course, by this time his penis was completely flaccid. Kayla snapped a picture. "Good boy. Now ask me for a treat."

To our unwavering amusement, Bobby remained in character. "Woof!" he barked.

"Good doggie!" she exclaimed while doling out yet another piece of candy.

It had been a virtuoso performance by Kayla, and she was about to wrap it up. She whispered to me, asking if it was okay to give Bobby the underpants. I handed them to her, along with the patch of Bobby's shorts that contained his key and money.

"Okay, Bobby," she said. "You've been a good naked doggie for me. I'll let you go back to being naked Bobby now. Stay there on your knees and put your hands behind your head, please." Bobby, now in full servitude mode, complied. "Good, Bobby," she said while snapping another picture. "Would you like to put on these underpants and get out of here now?"

"Yes, please," he said softly.

"You need to ask for them nicely. Say, 'Kayla, would you be so kind as to let me wear Johnny Boy's underpants?"

There was a look of alarm on Bobby's face when he realized the tighty-whities belonged to Johnny. I think he actually contemplated whether to go naked rather than suffer the indignity of pulling his friend's well-worn underpants tight against his genitalia. He ultimately chose the latter.

"Kayla, may I please––would you be so kind as to let me wear Johnny's––Johnny Boy's underpants?"

"Of course, dear Bobby," she said above the laughter. "But like Felicity said, starting tomorrow you're not allowed to wear underpants ever again." She reached out with the underpants. "Here you go. And here's the stuff from your pockets."

Bobby quickly pulled on the underpants. They were a size too small, but they served their purpose. Bobby stood there and looked at Kayla expectantly.

"You can go now, Bobby," she said, smiling.

It was another humorous sight as we watched Bobby run off as fast as he could toward the main building. He was fortunate to get there before too many other students were inside.

We saw him later in the day wearing his P.E. shorts and a tee shirt, along with some flip-flops, so he must have had them stashed in his locker. When he saw us he flinched and blushed profusely. It was quite apparent that from that day forward Bobby would not give us any trouble. Our wishes would be his commands.

At the end of the school day Kayla caught up with me and we gleefully rehashed the day's events. As we parted ways, Kayla called out, "Oh, and thank you for letting me take over while we were doing Bobby."

"The pleasure was all mine," I answered truthfully.

  • Chapter 16: BobbyBlondie., Mon Apr 16 2:48pm
    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 ... more
    • Chapter 16: Bobby — Blondie., Mon Apr 16 3:08pm
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You won't be getting your clothes back until you dance naked for us.