Roosevelt Humiliations

Stories about boys ending up in compromising situations, preferably naked and embarrassed, as the name suggests.
Hammer
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Re: Roosevelt Humiliations

Post by Hammer »

Have to ask will there be a story where the character of Blondie gets payback on his tormentors like Tommy in Tommy’s retribution?
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Blondie
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Re: Roosevelt Humiliations

Post by Blondie »

Hammer wrote: Sun Jan 28, 2024 4:40 pm Have to ask will there be a story where the character of Blondie gets payback on his tormentors like Tommy in Tommy’s retribution?
As of right now I don't have a story written where Blondie gets his revenge, but that doesn't mean it couldn't happen someday. Originally, when I wrote the epilogue to this story, I set up a scenario where Blondie indeed would get back at his tormentors. The scene would happen the very next night when the gang watched the video of Blondie's humiliations from the night before. While they were enjoying the festivities they were victimized by a couple of sadistic intruders, who brandished guns and forced the girls to strip. Blondie managed to hide in a closet, but opened the door a crack and captured it all on video. He would use the video as a threat and force his previous tormentors into compromising situations during the rest of their time at Roosevelt.

But I never posted it and changed the epilogue to what you see now, for two reasons: 1) As you will see in a future story ("The Felicity Chronicles: My Exploits as a Humiliator"), I wasn't done with Blondie's travails at Roosevelt High, and 2) I knew I wouldn't have time to write it up in the foreseeable future, and I didn't want to promise something I couldn't deliver.

There is a scenario where Blondie might get a chance to obtain retribution on Felicity. Without giving anything away, that potentiality presents itself in another story involving a boy named Andy (not the "Felicity Chronicles").
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Re: Roosevelt Humiliations

Post by Gomez »

Please keep writing these kind of stories, your a brilliant writer!
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Re: Roosevelt Humiliations

Post by Gomez »

I also wanted to add, your style of writing is great because you dont go over the top like many other stories I have read. You concentrate on the humiliation, and dont go down the pathway of dungeons etc. Thanks again.
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Roosevelt Humiliations, Chapter 14

Post by Blondie »

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Chapter 14 : Victoria’s Secret

The Mall

I was bright red and burning with shame as Brenda slid into the front seat and Becky scooted over next to me. The two of them were giggling and chirping like little birds while I drove in silence toward the mall, wishing I could vanish into thin air.

I’d already endured a morning full of humiliation, and I had no doubt there was more to come. My sense of dread was acute, as there was no telling what the two fiends had in store for me. I held on to a fragile hope that maybe, just maybe, I could stay in the car while they shopped. That hope lasted all of ten seconds.

I parked and waited, praying they’d hop out and leave me behind.

“Let’s go, Blondie,” Becky chirped as she gave me a firm nudge and slid out of the car.

I looked around and as was usually the case, a fair number of people were bustling about. And I was about to go join them, wearing short shorts, frilly socks and Becky's white tennis shoes.

God, please don’t let me run into anybody I know.

I closed my eyes for a second, took a deep breath, and stepped out of the car. I tried to keep my head down and my eyes forward as we crossed the parking lot. I didn’t dare make eye contact, though I could feel it—people looking, whispering. I lagged a little behind Brenda and Becky, hoping to draw less attention, but that plan backfired immediately. They each took one of my hands and, with wickedly innocent smiles, began cheerfully parading me through the mall.

That drew more attention.

I started to hear soft giggles around us, and it wasn’t long before I noticed two young teenage girls trailing behind, laughing to themselves. I caught Brenda peeking back at them and giving them a wink. I wanted nothing more than to bolt and hide in the nearest restroom.

After leading me around like their prize show pony, they came to a sudden stop.

Becky slipped our mom’s credit card into my pocket while Brenda turned to face me. I noticed the two teenage girls had lingered nearby, clearly curious to see what would happen next.


Lingerie

“Okay, Blondie, here’s the scoop,” Brenda said, her voice sugary and sinister. “See that store right behind you?”

I turned and nearly gasped. Victoria’s Secret.

“Good,” Brenda said with a smirk, seeing the horror on my face. “Here’s what you’re going to do. You’re going to walk in, nice and casual, and start browsing the merchandise. Maybe start in the panty section. When the salesgirl asks you if you need any help, tell her you’re interested in buying some lingerie. I’m sure she’ll be glad to help you. Got that so far?”

I think I had a look on my face like I’d just been punched in the stomach.

“Yes, I think you do,” she grinned. “And if she asks who it’s for, you say it’s for you. Not for your girlfriend. Not for your sister. You. We’ll be close enough to hear everything, so don’t get any ideas. And whatever she says—treat it like it’s coming from us.”

At the time, I had no clue what that meant. I later found out the salesgirl was Brenda’s friend—and this whole scheme had been cooked up days in advance.

And what a devious scheme it was.

“Alright, Blondie, you’re on.” Brenda turned my shoulders and lightly pushed me toward Victoria’s Secret, coaxing me inside.

I shivered in trepidation as I stepped inside. It was my first time in a lingerie store, and under the current circumstances, it was sheer agony. I walked to the other side of the store, somehow hoping to hide as long as I could.

But the store wasn’t crowded. Inside was just one other customer (along with Becky, Brenda, and the two teenagers, the latter who seemed quite enthralled with the proceedings), so it was only a matter of moments before the salesgirl was upon me.

In no time, an attractive young woman—maybe seventeen—approached me with a smile, which grew wider when she noticed my attire.

“Hi there! I’m Julie. Can I help you find something?”

She was all smiles, but when her gaze dropped to my legs and socks, her smile curved just a little more.

“Uh… uh…” My face flushed, and I looked straight down. “I-I’d like to buy some lingerie.” I spit the words out laboriously and blushed a deeper shade of pink.

“Well, you came to the right place!” Julie chirped. “Shopping for your girlfriend?”

I glanced at Brenda, who was staring at me from the bra section. She had a stern look of warning on her face.

I took a deep breath and said, “W-well, it’s not....for my girlfriend. There was a long pause while I stared to the ground, my blush growing by the second.

Julie tilted her head. “Oh? Who’s it for, then?”

“It’s… itsforme.” I squeezed the words together, barely audible. I heard giggles directly behind me, where the two teen girls were still lurking. My face was now pulsating with embarrassment.

Julie’s eyebrows arched slightly. “Ohhh, I see,” she said, clearly savoring the moment. She gave me a once-over and smiled. “Well, how cute.”

I glanced up at her to see if she felt at all awkward, but to my dismay I got quite the opposite impression—that she was taking pleasure in my discomfiture.

“Well, let’s see what we can do for you,” she said, gliding over to a rack of pastel teddies. “I think you’d look lovely in one of these.” She ran her fingers through the hangers, then pulled out a fuchsia number. “Do you know your size?”

I shook my head miserably. I just wanted to get it over with. “That one will be fine. I’ll take it,” I said as I started walking toward the counter.

She would have none of it. “Whoa, hang on,” she said, holding the teddy up to my chest. “Hold this for me, would you?”

I held the teddy by the straps while she stepped back about three feet and appraised me like I was some mannequin on display. The teenagers were looking on, giggling like the young schoolgirls they were. Becky and Brenda were close by, most assuredly reveling in the moment.

The salesgirl took her sweet time, extending my excruciating torment, as I stood there red-faced until I couldn’t take it anymore. I lowered the teddy and again started walking to the counter. “I’ll take it,” I said.

“No, I don’t think so,” Julie answered. “I think it might be a little too big,” she said. “You have a nice, slender physique. Something more form-fitting would really show off your charms.”

I couldn’t believe the salesgirl wouldn’t just let me buy the damn thing and let me get the hell out of there. Plus, I was getting the uncomfortable impression that she was teasing me. I mean, my charms? Please.

Then, unbelievably, my plight worsened.

I lowered the teddy and tried to escape to the counter. “I’ll just take it,” I said.

Julie intercepted me. “Nope. You really need to try one on to make sure it fits you just right," she asserted.” Her voice was playful, but firm. “Go into the dressing room and get undressed while I find one just like this, only a little smaller. I’ll hand it over the top of the door.”

I froze, quite resistant to the turn of events. “Really, that won’t be nec—”

“I insist,” she said with a smile that didn’t invite argument. “It’ll save you from having to return it later. Now go get undressed and I’ll be right with you.”

Again, I caught Brenda’s eye and remembered her warning. My legs felt like jelly as I made my way into the small dressing room.

The top of the door reached the middle of my forehead. I locked it and stood on tiptoes, peeking warily out. Yep—Becky, Brenda, and the two teenage girls were all watching, grinning ear to ear. The salesgirl, Julie, had an impish grin on her face as she sifted through the rack of teddies. And as if that wasn’t enough, a tall, elegant blonde woman—maybe late thirties—was watching from between two racks of panties. She was clearly more interested in me than anything the store was selling.

I couldn’t believe what I was about to do.

I peeled off my shirt, looked around for a hook or bench—nothing—so I dropped it to the floor. I hesitated, heart pounding, then slowly unfastened the shorts, pushed them down, and stepped out of them. Now I stood in a Victoria’s Secret dressing room, wearing nothing but my underpants, frilly socks, and girl’s tennis shoes. I crossed my arms over my chest and waited. I shivered and looked down at the goosebumps on my arms.

At that point Julie must have seen my feet through the six-inch opening under the door. Her voice floated in, loud and chipper.

“You can take off your shoes and your pretty socks too, sweetheart! You’d look awfully silly wearing a teddy with shoes and socks, don’t you think?”

I winced. I could hear the laughter outside. But I bent down, peeled off the shoes and socks, and set them aside. I could see Julie’s feet pacing just outside the door. She wasn’t as tall as I am, so (fortunately for me!), she wouldn’t be able to peer in at me.

“I’m sorry there aren’t any hooks,” she continued cheerfully. “We’re in the middle of a remodel. If you want, you can hand your clothes over to me and I’ll hang them up on one of the racks until you’re ready.”

“N-no, that’s okay,” I said, my voice trembling. “It’s just an old shirt and a pair of shorts…” The anxiety in my voice betrayed my desperation.

“Come on, sweetie, hand ’em over,” she coaxed. “It’s part of our service here. You wouldn’t want me to get in trouble with my manager, would you?”

A hand popped up over the door, open and waiting.

Reluctantly, I picked up my shirt and placed it in her hand. It vanished. A moment later, the hand returned—empty.

I groaned and reached for my shorts. Up they went, and again—gone. No sign of return.

The empty hand reappeared. Trying my luck, I handed over one of my shoes.

Julie laughed. “No, silly boy. Your underpants. You don’t want your panties sticking out from under your teddy, now, do you?”

I heard the snickers coming from inside the store. The only thing worse than hearing the word “panties” was the fact that I was about to relinquish my underpants.

I froze. The hand above the door opened and closed a few times impatiently.

“Come on,” Julie sang. “Undies, please.”

Resigned to my sorry plight, I lowered my underpants, stepped out of them, and placed them in the outstretched hand, which quickly vanished.

“Thank you, kind sir,” Julie called out sweetly. “I’ll be back in a moment, and we’ll try on your teddy.”

The sound of laughter followed her footsteps as she walked away. I stood there naked, oh so naked, holding my crotch with both hands.

Time slowed to a crawl.

After a minute or two, I looked up—and nearly jumped. Becky and Brenda’s heads were peeking over the top of the door, grinning down at me.

“Hi, Blondie,” Becky teased. “Enjoying your outing?”

I ducked down into a crouch, hands still covering myself as they giggled and walked away, clearly delighted.

A few moments later, Julie’s hand reappeared, holding the teddy aloft.

“Here you go, sir. I think this will fit you rather nicely.”

I took it from her and slipped it on as quickly as I could. The silky fabric clung to me like a second skin. I pulled the straps over my shoulders and stood there, humiliated beyond belief.

“I’m sorry we don’t have a mirror in there,” Julie said. “But there’s a full-length one out here, so when you’re ready, you can come out and we’ll check the fit.”

I should’ve seen that coming, but somehow it caught me off guard.

“N-no, really, that won’t be…you don’t need to do that,” I replied, voice cracking.

“Oh, but I insist!” she chirped. I thought I heard her stifle a giggle.

"Really," I tried again. "It....it fits fine. I'll take it."

"Oh, but we need to be sure, sweetie. And I do have a little more experience with lingerie than you do. At least….I think so.” Another giggle. "Now come out of there right now, and let's have a look at you.”

I knew I had to comply, and the sooner I did, the sooner the ordeal would be over.

I took a deep breath, slowly opened the door, and stepped out.

Six sets of eyes were fixed on me, all coupled with ear-to-ear grins.

“Oh, how darling,” Julie cooed. “Come, come, let’s have a look in the mirror.”

She draped her cool fingers around my elbow and guided me through the store—slowly. I tried to speed up, but the devilish salesgirl held me back, stretching out every mortifying second. The silky fabric swished against me with every step, reinforcing my humiliation, as did the giggling coming from the other girls.

Finally, we reached the mirror.

Julie smiled, then turned me toward the glass. I looked up and saw a boy wearing a teddy. His crimson face closely matched the fuchsia color of his garment. I don’t think I’ve ever seen anybody look more miserably embarrassed than the guy I saw in the mirror that day.

“I think this is perfect,” Julie said, fussing with the lace along the hem. “How does it feel?”

I was in no mood to discuss the nuances of the teddy. “It’ll be fine,” I said abruptly. “I’ll take it.”

I turned and hurried back to the dressing room, cheeks burning.

Once inside, I shut the door and called out, “Okay, may I please have my clothes now?”

“Of course! I’ll make a little trade—hand me the teddy, and I’ll go get your clothes for you."

I didn’t trust the fiend any further than I could throw her, but I was in no position to negotiate. I stripped off the teddy and draped it over the door. It disappeared instantly.

I stood there, naked (again), waiting impatiently for a few minutes, but (big surprise) nothing was forthcoming.

Then her voice, sweet and smug, came from right outside the door.

“Excuse me, sir, but I’d be remiss if I didn’t mention our sale today on our line of undergarments. All bras and panties are thirty percent off. Would you like to try on a new set?”

I shut my eyes and fought the urge to scream.

“No, thank you. Just bring me my clothes, please.”

“Oh, but you simply must try a sample from our new line! I think you’d look precious. Do you know your cup size?”

Laughter erupted from outside.

“No, please, I’m okay,” I pleaded desperately.

“Hang on, I’ll be right back."
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