Roosevelt Humiliations
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Re: Roosevelt Humiliations
Have to ask will there be a story where the character of Blondie gets payback on his tormentors like Tommy in Tommy’s retribution?
- Blondie
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Re: Roosevelt Humiliations
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.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?
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").
Re: Roosevelt Humiliations
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.
- Blondie
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Roosevelt Humiliations, Chapter 14

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."
- Blondie
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Roosevelt Humiliations, Chapter 15

Chapter 15: A Mortifying Measurement
The Measurement
I shook my head in disbelief, crouched low and shivering, still completely unclothed. My hands were wedged tightly between my thighs as I huddled on the cold floor, silently praying for a miracle—or a black hole.
After a bit there was at the door. “Knock-knock!” Julie chirped, far too cheerfully.
“Yes?” I answered the salesgirl anxiously.
But instead of a response, I heard the unmistakable click of a key sliding into the lock.
“What—hey!” I yelped, just as the door popped open and Julie waltzed in. “What’re you…I’m na....I'm not dressed!”
“Not a problem,” she said without batting an eyelash, as if it was standard procedure for her. In her hand was a measuring tape and a clipboard. On the clipboard was a sheet of paper with a drawing of the outline of a female human figure. “We just need to get you sized properly. Head to toe. Nothing to be embarrassed about.”
“Oh! Please, I don’t need…at least let me get dressed first?” I stammered, inching backward in vain.
Julie smiled sweetly. “No need for that, honeybun. Nothing I’ve never seen before, so there’s no need to be bashful. Besides, it’s much easier to get exact measurements this way. While you're naked. Now be a good boy and stand up straight for me, hmm?”
With a pitiful groan, I rose slowly, keeping both hands firmly clamped over my modesty. I stared straight ahead, face burning, as Julie casually left the door cracked open. Naturally, Becky, Brenda, and the young teens needed no further invitation. The door creaked wider as their wide-eyed faces peeked in, hungry for more spectacle. Of course, Julie made no effort to discourage them.
Trying (and failing) to suppress her smirk, Julie knelt behind me and gently lifted my right heel. “If you’ll hold down this end with your heel, I’ll go ahead and get your height.” She stood and extended the tape to the top of my head. “Stand tall now….aaand….five-nine and a half. Excellent!”
She looked around. “Shoot, I forgot the scale. Don’t go anywhere,” she said with a wink, already halfway out the door.
“It’s okay!” I called back anxiously. “Why do you need my.…I weigh one thirty-fi—”
“I’ll be right back! It’s best to weigh you while you’re naked!” she hollered from the sales floor, much louder than I thought necessary.
The giggling girls continued to hang about the doorway while I waited impatiently for the salesgirl. I turned my back to the girls and bent to a crouch. It was a full five minutes before Julie returned.
“Sorry for the delay,” she said brightly, stepping back in with the scale. “Had to help another customer. But don’t worry, I’m all yours now.”
Wonderful.
She laid the scale on the floor and motioned for me to step on. When I did, she announced what I already knew. “One thirty-five. Five-nine and a half, one-thirty-five,” she said, scribbling onto the clipboard.
She looked up at the girls. “Excuse me, but could I trouble one of you girls to write down this information for me as I call it out?”
Becky jumped at the opportunity. “No problem,” she beamed as she stepped into the room and took the clipboard.
“Thank you so much,” said Julie.
I stood helplessly, still covering myself as best I could, while Becky took her place beside Julie—both clearly reveling in the moment.
“Okay, let’s get your neck size, sweetie. Chin up,” Julie said, gently tilting my head with her fingertips. “Once we get all your measurements, you can go to our website and do your lingerie shopping online....looks like fourteen inches exactly. Lovely swan neck you’ve got.”
I groaned softly.
"Okay, I’ll need you to hold your arms straight out to your sides, sweetheart, so we can get your chest size.”
“Please,” I whispered, “just… let me put something on.”
Julie rolled her eyes like I was being dramatic. “Now, now, we’ve been over this. Your measurements are much more accurate when you’re nice and naked. Now be a good boy and make this easy for me. Arms out, soldier. Nice and straight, like you’re ready to take off.”
I glanced at Brenda and saw the unspoken command in her eyes. With a defeated sigh, I knew what I had to do. Slowly, painfully, I moved my hands from my crotch, exposing myself to the full view—and full judgment—of the room.
“Atta boy,” Julie said with a grin, her tone sugary sweet. I caught her eyes flicking down to where my hands had just been. Her smirk widened, unmistakably amused by the view.
“See how easy that was? Now let’s get these arms up," she said as she took hold of each of my arms and lifted them up. “There we go—flying position. Hold that pose....perfect!”
She slipped behind me for the chest measurement, most assuredly to give the girls an unobstructed view of my exposed genitals. Becky and Brenda had seen me naked before, but they were grinning brightly, as their enjoyment of my humiliation seemed to have no limits. The young teenyboppers were grabbing onto each other and giggling uncontrollably while staring at my genitals. It was all I could do to keep from running off.
“Thirty-two inches,” Julie announced. She walked around and gave my chest an appraising look. “That’s a double A cup, for sure.”
Cue another wave of laughter. Becky dutifully jotted it down like she was recording lab results.
“Okay,” she continued. “Let’s get your waist size now. I’ll need you to hold your arms up high in the air. It’s best to get the waist measurement while you’re all stretched out, in case you ever want to wear a corset.”
I grudgingly raised my arms slightly.
“All the way up, please,” Julie directed.
Reluctantly, I obeyed, raising my arms like a yoga student.
"Now interlock your fingers and face your palms to the sky……no, turn them up, so your body will be nice and taut….there you go, perfect….you’re all stretched out now….I must compliment you on your hygiene….lovely smooth underarms.”
The giggling turned up a notch. It was true—though I had sprouted some pubic hair, my armpits were still hairless.
She walked behind me to take the measurement, affording the other girls what for them was I’m sure a very entertaining view.
“Twenty-eight inches." After a pause, she said, “With a corset I think you’ll have a lovely hourglass figure.”
I dropped my arms again, my hands snapping back over my crotch like magnets.
Julie came back around and faced me. “Okay, we’re almost done. I just need to measure your hips so your panties will be properly sized.”
I groaned softly to myself as Julie knelt once more.
She looked up at me. “You’ll need to hold your arms up and out of the way, please.”
With a defeated sigh, I crossed my arms over my chest and tried to pretend I wasn’t standing there naked, being sized for panties.
Julie wrapped the tape around my hips. Her eyes were no more than two inches from my penis as she purposefully scrutinized her objective—and at that moment, I don’t think it was the tape.
As she stood up, she couldn’t suppress another smirk, only now it was more pronounced. “Definitely an extra small,” was her stinging remark. While everyone laughed, she gave my flushed face a sympathetic pat. “There, that wasn’t so bad, now, was it?”
I didn’t answer. I couldn’t.
As everyone trickled out, still laughing, Julie turned back and chirped, “Be right back with your bra and panties!”
The door clicked shut, and I locked it in a hurry. I leaned against it, face in my palms, and muttered into my hands.
“Oh….my.…fucking....God.”
Bra and Panties
My reprieve was short-lived. Barely two minutes had passed when Julie’s hand appeared over the dressing room door, holding a pair of lavender-colored panties. “Would you try these on for me, please?”
Shuddering, I took the panties and gingerly slipped them on. They hugged me a little too well. I winced as I glanced downward.
“Well?” Julie’s voice was expectant, chipper.
“They’re….fine,” I answered meekly.
Next came the matching bra, unceremoniously draped over the top of the door. I tried ignoring it, but—yeah, no chance.
“Don’t forget your bra,” came the cheery voice from the other side of the door.
I reluctantly slid the shameful garment off the door and stared at it like it might bite me. Which direction did this thing even go? Julie, sensing my struggle, piped up again.
“Slip your arms through the openings, sweetheart, then clasp it in the back. Would you like some help?”
“No!” I blurted far too fast. “I mean….I can do it."
After a full-on wrestling match, I finally managed to secure it. I felt ridiculous, and more than a little humiliated.
“How are we doing in there?” asked the all-too-helpful Julie.
“Fine. They fit fine. Really. I’ll take them….if that’s what you want.”
There was a brief pause.
Maybe she was done?
“Just to be sure, I think we should have a look in the mirror.”
Of course she does.
I closed my eyes for a moment to gather myself. Then I opened the door.
“Oh, you look adorable,” Julie gushed. “Do you feel as sexy as you look?”
I didn’t dignify that with a response. I power-walked toward the mirror, wishing I had a paper bag for my head.
As expected, I was met by a growing crowd of grinning faces. Becky and Brenda were beaming, their amusement clearly endless. The teenage girls were practically bouncing with glee. The blonde customer from before observed from a distance. She looked quite amused. And now, because this clearly wasn’t humiliating enough, another saleslady and a couple of other women in the store had taken notice of the show.
When I reached the mirror, the girls formed a cozy semicircle around me, looking on with great amusement. Julie sidled up to me.
“Oh yes, this is definitely you,” she said, adjusting the lace along the bra cups with professional ease. “Lavender is such a lovely color on you, don’t you think so?”
The two new customers had wandered closer, watching like they’d stumbled onto the best matinee in the mall. I needed to get out of sight immediately.
“Yes….I mean, no….I mean—I’ll take them, please!”
I spun on my heel and bolted toward the dressing room, desperate for cover. But to my horror, the door was closed—and locked. Someone was already inside. In a mini-panic, I looked around for another dressing room, but there was none to be found.
I knocked on the door. “Excuse me, but can I get in there?” I asked anxiously.
A woman’s voice replied smoothly, “I beg your pardon, young man, but I’m busy in here.”
The occupant paused and peeked at me over the door, looking me up and down with open amusement. Tall Blonde Lady from before. Grinning widely, she calmly said, “She’s right, you know. It is a lovely color on you.”
My nightmare continued. I stood stiffly by the dressing room door, one arm crossed over my chest, the other shielding the front of the panties. It wasn’t until later, replaying the scene in my mind with a shiver, that it struck me: I was striking the exact pose any modest girl in my situation probably would’ve assumed. And once that realization sank in, it only deepened my shame.
Becky, Brenda, and the two teenagers clustered around, savoring every second of my mortifying exposure.
Eventually, mercifully, the dressing room vacated. I scrambled inside and slammed the door shut, breathing a sigh of relief like never before.
But then I realized....my clothes were still missing.
I poked my head above the door and looked around, but they were nowhere to be seen. I spotted Julie a few yards away. She was still grinning.
“May I please have my clothes now?” I called out to her.
“Sure!” came Julie’s cheerful voice. “I’ll get them for you. First, though, hand me your new bra and panties, and I’ll wrap them up for you.”
Naked Again
I sighed and peeled off the offending garments. They were snatched from the door in a blink, and once again I was left naked and waiting....and waiting.…and waiting.…
“Excuse me?” I shouted, now with impertinence. “I’m still waiting for my clothes!”
“Sorry, I’m helping another customer. Your clothes are hanging on the rack with the babydolls. You’ll have to get them yourself.”
I groaned. I should have known it would come to that.
Peeking out, I scanned the store. I had no idea what a babydoll even was, but clearly I wasn’t going to find my outfit without parading through the store naked again. Desperate, I grabbed a tennis shoe. I held it over my genitals, which fit perfectly inside the opening of the shoe.
I made a break for it.
The store exploded in laughter. Out of the corner of my eye, I saw several people peering through the window—one of them actually pointing at me with glee.
I darted from rack to rack like a deranged shopper on Black Friday, searching for anything that resembled my clothes. No luck. Tall Blonde was headed toward the dressing room again, and I barely beat her to it.
I slammed the door behind me and yelled, “Please! Can somebody please bring me my fucking clothes?!”
The Teddy
There was silence. Then, slowly, ominously….a fuchsia teddy was draped over the door.
Becky’s voice followed. “That’s no way for a young lady to talk. Now put on your new teddy and let’s go home.”
“Oh, shit,” I muttered to myself. I pulled the teddy off the door and leaned against the wall, feeling hopeless. “Ohhh, shit.”
There was a knock. “Open the door!” Becky demanded.
In a rush, I pulled the teddy on—again—and turned the knob. Becky burst in, holding a shopping bag.
“If you’d just asked nicely,” she teased, “I would’ve given these to you.”
She showed me the contents—my shorts, t-shirt, underpants—and then she dropped in my shoes and the frilly socks.
“Let’s go,” she said with a sunny smile.
“Oh God, please, Beck! I can’t—not in the mall!”
Becky simply smiled and tugged at my elbow.
I pulled loose and tentatively ventured out of the dressing room. Once again, I was the center of attention. I briskly walked toward the exit.
But there was Julie, waving merrily from behind the counter.
“Yoo-hoo! Don’t forget to pay for your lingerie, sir!” she called, delighting in every syllable.
I gave Brenda a desperate look. She smiled and nodded toward the counter. Becky reached into the shopping bag, retrieved the credit card, and handed it to Julie. She took an unusually long time to complete the transaction while I stood there, basking in my degradation.
At last, the smiling Julie handed me the pink bag containing my new bra and panty set. The bag had giant “VS” logo emblazoned on both sides.
“Thank you so much,” she said. “You’re my new favorite customer. Please come back soon. I’ll be happy to help you any time.”
I turned away to leave and Becky jabbed me in the ribs.
"Thank you for your help,” I mumbled, trying not to cry.
“Oh, trust me,” Julie said, her smile wicked, “the pleasure was all mine.”
The walk through the mall was its own special kind of torment. Becky and Brenda each took one of my hands, parading me like a show pony. The young girls trailed behind, openly giggling. I tried to walk fast, but my sister and Brenda held me back.
I even had to wait while they ordered an ice cream.
By the time we reached the exit, I’d lost count of how many people had stared, whispered, pointed, laughed. I heard one wolf whistle, an “Oh, how darling!” and—just to truly cement my humiliation—a loud, “Look at the pretty boy in the lingerie!” I can’t tell you how many shades of red I turned throughout that walk.
When we exited the mall the two young teenage girls stopped at the door and watched us cross the street into the parking lot. As we got in the car the sound of their giggling voices still rang in my ears.
Last edited by Blondie on Wed Apr 23, 2025 10:15 pm, edited 1 time in total.
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Roosevelt Humiliations, Chapter 16

Chapter 16: Tormented by Becky and Brenda
Under Brenda and Becky’s Thumb
Well, again I must apologize for taking so long in between the accounts of my humiliating travails at the hands of Brenda, Becky and the others from Roosevelt High. You see, I’ve been trying to put it out of my mind, but of course, considering the magnitude of my shame, that’s impossible to do. So I may as well finish what I have started, for posterity’s sake, and for the sake of any readers still grimly amused by my suffering.
Here’s a refresher, just in case you’ve managed to forget what I can’t: My junior year is finished, but I still have a few incidences to relate that occurred during my junior year and in the summer. When we last communicated, Brenda and my sister Becky had thoroughly humiliated me at the mall, where I was put through my paces at Victoria’s Secret. I even had to buy a teddy, and my own bra and panties set.
After that incident, I understood my position clearly: I was completely under their control. Any time I so much as considered defying them, I had only to recall the beach episode—where I ended up stark naked in public and later forced into one of my sister’s swimsuits—to remind myself just how bad things could get. And I had no doubt things could, and would, get worse if I stepped out of line again.
Much to my detriment, Brenda and Becky have become very good friends. In fact, they have formed quite the bond, and when the two of them put their scheming, devilish heads together it never bodes well for me. Whenever Brenda came over, I felt a wave of dread washing over me. It was hard enough to deal with Becky on her own, but the two of them together? That was a recipe for disaster.
Disaster struck one Sunday evening. I wasn’t in a very good mood. I hadn’t had much sleep the night before, I had lost a bet on the football game, and Brenda was at the house visiting. That combination was enough to make me very irritable.
I was lying on my bed reading the sports section when Becky and Brenda barged into my room without knocking. Their purpose was to ease their boredom by teasing me. I was in no mood for their shenanigans.
“Hi, Blondie,” sung Becky as the two of them stood over me with smiles on their faces. “Whatcha doin’?”
“What does it look like I’m doing?” I grumbled. “And could you please knock next time? This is my room, you know.”
“Ooh, it must be that time of the month for Blondie,” teased Becky.
“Maybe Blondie’s afraid we’ll surprise him while he’s massaging his little weenie,” Brenda chimed in. They both laughed. “Or maybe he was just about to try on his pretty new outfits from Victoria’s Secret.”
They both laughed, while I seethed—and blushed—behind my paper.
“Hmm, what a great idea, Brenda,” Becky considered. “Blondie, we’re kind of bored right now. How would you like to model your lovely new lingerie for Brenda and me?”
My guard was down, and I spoke without thinking. “Eat shit, Becky, and get the fuck out of my room!” I shouted.
The moment those words left my mouth, I knew I’d messed up. Badly.
“Okay, that’s it, Blondie,” reprimanded Becky, her tone ice cold now. “I’ve had quite enough of your attitude lately. And to act like that in front of my guest….you’re going to pay for this.
She turned to Brenda. “Come on. We need to have a little strategy session.”
Before leaving, she shot me one last glare. “And don’t even think about leaving this room. Do you hear me?”
I didn’t answer.
“I said, DO YOU HEAR ME??”
I nodded meekly.
They exited. Brenda paused in the doorway and puckered her lips while giving me a fake kiss. “See you soon, Blondie.”
As I lay on my bed my mind was racing, and I was dreading what diabolical conspiracy they were devising. At least fifteen minutes had gone by before the grinning girls reentered my room, again without knocking.
To my dismay, Becky was dangling the bag that I recognized from Victoria’s Secret. She noticed me gazing at the bag with a look of apprehension.
“Does this look familiar, sweetie? How about this?” She reached into the bag and pulled out the lavender-colored bra and panty set. “Remember how precious you looked in these?”
“Please, Becky, I’m sorry, I don’t know what got into me earlier. I’m just….really tired. Honestly, I didn’t mean it.”
My pleas fell on deaf ears. “Well maybe next time you’ll think twice before giving me any of your dirty lip. In the meantime, you need to learn a lesson. Now, here’s what’s going to happen: You’re going to put on your new bra and panties and come out to the living room, wearing nothing else. Brenda and I are hungry, so maybe you can serve us dessert while you swish around in your cute little girly undies.”
I stared at her in disbelief, but she wasn’t done.
"Then, if you’re really nice,” she added with a smirk, "we might even put on some music and let you entertain us with a little dance. On the coffee table. In your sexy underwear. Now strip off those boy clothes and make yourself pretty for us. We’ll be waiting for you in the living room. You’ve got five minutes.”
She dropped the lingerie on my bed, and Brenda came up behind her.
“Don’t worry, sweetheart,” she cooed, pinching my cheek. “You’re going to look adorable. And I have a feeling you’re going to be quite the dancer.”
They left me alone with my doom. I stared at the delicate lace for a long moment, the color draining from my face. Then, with a deep, resigned sigh, I slowly, deliberately started stripping off my clothes.
I couldn’t believe I would have to wear the bra and panties again. I tried to comfort myself with the fact that at least I wasn’t in a public place. But Brenda and Becky were enjoying my disgrace way too much, and the thought of serving them and then (oh, God) having to dance on the coffee table for their entertainment while wearing a pair of panties and a bra...that was a dreadful notion.
But I had no recourse—to disobey them would mean much worse repercussions down the road. Shuddering, I slipped the panties up my naked body. I pulled the bra on and managed to clasp it in the back. Then, while looking in the mirror, I pulled the straps over my shoulders and took in the very discomforting reflection. I actually turned around to see how I looked from the rear and then chastised myself for doing so. I remember thinking that from the rear, I could probably pass as a girl (which would only give the girls more ammunition to tease me with), what with my smooth skin and slim features. Fortunately, I had grown some hair on my legs. It was blond, and not that noticeable, but at least it was something.
I sat on the bed with my head in my hands. My moment for self-pity would be short-lived, though, as I heard Becky’s voice calling from the living room.
“Blondie, we’re waiting,” she sang. “Come on out and shake those hips for us.” Loud giggling from the two girls ensued.
My sweaty hand was on the doorknob when I heard what at the time was music to my ears: the front door opening, and the voices of my mom and dad. They had come home from a movie much earlier than expected.
I exhaled hard. No way would Becky want our parents to know of the depravity she was inflicting on me. I’ve even considered telling them about it but squelched that idea when I realized that once Mitch found out, then I’d be dog meat.
In any case, for the moment I thankfully had a reprieve, and I turned around to get dressed. Just as I did, Brenda barged in. My back was to her as I scrambled for my clothes.
“Oh, Blondie, how cute,” taunted Brenda as she squeezed my pantied ass before I managed to pull up my jeans.
I didn’t bother stripping off the underwear. I quickly pulled on my jeans and tee shirt right over them so Brenda wouldn’t see me naked.
I turned around and Brenda smiled at my blushing face. “Thanks for the sneak preview, Blondie. We’ll have to pick this up where we left off sometime.”
She exited the room with a giggle as I felt a pang of anxiety over the prospect of a repeat performance, but breathed a sigh of relief over escaping certain humiliation that night.
More Roosevelt Humiliations
My respite didn’t last long.
At school the next day, I had just finished eating lunch and was kicking back, taking in a few rays while leaning against the Roosevelt statue. I should have known better than to go near that damn thing—it seemed like every time I did, something awful happened.
Sure enough, my moment of tranquility was shattered by the ominous, too-cheerful voice of Brenda.
“Well, well, well… Blondie. How nice to see you.”
I wasn’t fooled by the cheerful tone. I opened my eyes to find Brenda, Becky, Marcia, and Cheryl standing over me, all wearing smiles far too sweet to be sincere. One look at their faces, and I knew—something awful was about to happen.
“I hear you look positively adorable in lingerie, Blondie,” teased Marcia. “It would be a treat if you could put on a fashion show for us sometime.” They all giggled.
“Oh, absolutely,” Becky added, taking the cue. “He makes a lovely little teenybopper.” More giggles. More dread.
Becky inched a little closer to me while reaching into her purse and pulling out a tube of lipstick. A sudden fear swept over me as I eyed the lipstick tube like it was a rattlesnake ready to attack.
“Can you believe,” she said to the group, “that he told me to ‘eat shit’ last night? Such language! I mean, is that any way for a proper young girl to talk?”
I jerked my head back as the lipstick inched toward my face, but Brenda was faster. Her hands gripped my shoulders, firm and unrelenting.
“Hold still, darling,” she whispered, just loud enough for me to hear the amusement in her voice.
“Maybe if you looked more like a girl,” Becky mused, “you’d learn not to talk to your fellow females so rudely.”
Before I could wriggle free, she was applying the lipstick. Thick, bright pink. Her movements were slow and deliberate, drawing laughs from the entire group as I sat there, frozen and mortified.
What is it about these girls that they got off on feminizing me?
Becky stepped back to admire her work, smirking. “That’s a good girl, Blondie. Now hold still while I add a little blush.”
She looked at me closely. “On second thought, your cheeks are blushing on their own, you don’t need this. She burst out laughing. “You look marvelous, sweetie.”
She opened her compact and held up the mirror. I was chagrined to see a youngish-looking boy with bright pink lipstick and very red cheeks. I glanced around, silently praying that no one else had seen me like this.
But Becky, as though reading my mind, took care of that in short order.
“Oh hey, look over there,” she said casually, pointing to two coeds chatting nearby. “Do me a favor, Blondie. Go ask them if they have any eye shadow you can borrow. If you succeed, I’ll let you wipe the lipstick off. If not….”
She let the silence hang for effect. Then: “…you have to wear your cute little bra and panty set to school tomorrow. Instead of your underwear.”
I tried to find a way out of the predicament. “Beck, please. I’m really sorry about last night. I swear, it won’t happen again.”
Becky smiled sweetly. “Go, girl, before I put you over my knee and give you a spanking. And rest assured, I’ll pull down your undies and give you a bare-assed slapping that you’ll never forget.”
The girls howled with laughter.
I needed no more prodding. I reluctantly made my way over to the two girls.
I decided to take the direct approach. “Excuse me,” I said, folding my lips inward as I approached. “Do either of you….um, have any eye shadow?”
“Why do you want eye shadow?” asked one of them, a petite brunette. Her eyebrows were furrowed in confusion.
“It’s for my sister,” I blurted, pointing toward Becky’s group and awkwardly folding my lips again.
That exchange served two purposes, both to my detriment. One, while I spoke, my newly painted lips were exposed to the two girls.
Two, when I pointed out Becky, the two girls turned and saw my four tormentors in hysterics—pointing, laughing, clearly loving every second. The two coeds sized up the situation, and it didn’t take a rocket scientist to figure out that I was the victim of a Roosevelt High hazing.
The faces of both girls lit up. They pounced on the opportunity to join in the festivities. “Come on now, ‘fess up, the eye shadow is for you, isn’t it?” asked the brunette. Both girls were giggling.
“N-no, really,” I stammered, “It’s for my sister. Please, can I just get some?" I was blushing crimson, looking down at the ground.
The brunette, clearly enjoying herself, reached into her purse. “How cute,” she continued, “You're like a little schoolgirl, wearing lipstick and blushing like that. I’ll tell you what, you can have some eye shadow if you let me put it on you.”
I hesitated, weighing my options. Public humiliation now or bra and panties tomorrow?
“Okay,” I muttered.
She grinned and pulled out a compact with baby blue eye shadow. As she lifted the applicator, I instinctively closed my eyes. I could hear my sister and her gang laughing from the sidelines, the sound carrying across the courtyard.
“Oh my god,” the brunette’s friend squealed. “I can’t believe this!”
Indeed, neither could I.
When she finished, she stepped back with a satisfied nod. “Oh, yes, you look lovely, little schoolgirl.”
More giggles. I had quite enough and turned to walk back toward my tormentors.
“Thanks for coming by, cupcake!” the brunette called after me.
I walked from two giggling strangers to four cackling maniacs.
The bell rang just as I reached them.
“You can go clean up now, Blondie,” Becky said, handing me a Kleenex through tears of laughter. “But don’t get too comfy. I still owe you for last night.”
I didn’t stick around to hear more. Spitting out the awful taste, I bolted straight for the bathroom, which fortunately was empty. I wiped off the lipstick and scrubbed off the makeup as fast as I could.
I shivered, angst-ridden at the possibility that Becky still had a reprimand in mind.
Sure enough, it came just a few short days later—in spades.
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Roosevelt Humiliations, Chapter 17

Chapter 17: The Bubble Bath
Denuded
It was a lazy Saturday afternoon, and I came home after two grueling hours of basketball. My parents were out of town for the weekend, and Becky had gone off on some overnight adventure with Brenda. I had the place to myself, and I was looking forward to it.
I pulled off my clothes and went into the bathroom to take a shower. Just as I was about to turn the shower on I spotted my sister’s bubble bath leaning against the corner of the tub. I was a little sore from basketball, and I figured a good soaking would do me good, so I ran the water and poured in some bubble bath liquid. I don’t know what got into me—I hadn’t taken a bubble bath since I was a little kid, but in that moment, I didn’t care. The water was perfect. So perfect, in fact, I started nodding off.
Big mistake.
I don’t know how long I was out, but I was rudely awakened by a tickling sensation on my balls.
I opened my eyes and nearly died on the spot. Standing over me, grinning like cats who’d cornered a mouse, were Becky and Brenda.
I yelped and instinctively swatted Brenda’s hand away. The two girls were laughing uproariously as I flailed about for a while, at a loss for what to do.
Finally, I realized that I best not disturb the bubbles; they were the only protection I had for my modesty.
“Well, well, brother dearest,” Becky purred, clearly relishing every second. "Is this sweet revenge, or what?”
Of course, she was referring to the time many years before that a friend and I intentionally walked in on her while she was taking a bath. She’s never forgiven me for it and was surely in her element over the classic case of poetic justice.
“How cute, a bubble bath," teased Becky. "Let’s see, you bought a bra and panty set, you’ve been wearing lipstick and eye shadow, and now you’re soaking in a bubble bath like a little sissy. It seems to me you want to be a girl. Well, just sit back and relax. Auntie Brenda and I are about to make your day.”
The smiling Becky reached across the tub and grabbed a lady’s pink disposable razor. “Brenda, there’s another one of these in the medicine cabinet. I’ll start on his legs, maybe you can shave his underarms, if he has any hair under there.” Becky giggled, and Brenda, grinning mischievously, wasted no time producing another razor. “Hold up your leg,” demanded Becky.
“What? No! Becky, please—don’t do this!”
I was horrified. I was a late developer, something that had grated on me, and when I finally started growing bodily hair I was quite grateful. Now, with its removal imminent, especially at the hands of the devilish Becky and Brenda, I was quite shaken.
"Please, I’ll do anything, don’t do it!” I had bolted upright and was screaming.
“Anything?” Brenda said sweetly, already reaching into the cabinet. “Then lie back and hold still, sweetheart. Let your loving sister and Auntie Brenda make you niiice and smooth, like the little girly-girl you are.”
She tried to ease me back with her hand pushing on my chest, but I resisted.
“That does it, I’m getting the scissors,” interrupted Becky. "Let’s cut off all his pubic hair, then we’ll take some pictures.”
“Okay, okay!” I relented, lowering back down. My situation was dreadful enough, but I didn’t want to lose my precious pubes.
That got their grins back. Becky grabbed my foot and lifted my leg into the air. I couldn’t believe what was happening.
“There we go. Now hold still, sweetie. We don’t want any nicks on those pretty legs.” She squirted a puff of shaving cream into her palm and smeared it over my shin. She started at my ankle and made a few sweeping motions with the razor, all the way to my knee.
“It was a good idea to take a bath, Blondie," Becky teased. "The hot water has really softened up the hairs. Look how easily it’s coming off.”
I closed my eyes, wincing, as I couldn’t bear to watch.
Then Brenda grabbed my wrist. “Arm up, sugarplum. Let’s see what’s hiding under here. Oh, yes—definitely some fuzz. We can’t have that, now can we? A proper girl should have nice, smooth underarms. Hold your arm waaay up high, dear, so we can get rid of these unsightly things.”
Miserably, I complied, much to my dismay. I had finally started growing armpit hair just a few weeks before, and now it would be gone.
While Becky continued working her way up my leg, Brenda made short order of the small amount of hair on my right armpit. “Other side now, pumpkin. Turn toward me—good girl.” Hearing Brenda sweet-talking me and calling me a girl only added to my extreme mortification, and she knew it.
She finished off my other armpit and ran her hand in a circular motion around my chest. “Oh yes, nice and smooth. We don’t need to spend any time here.”
Brenda glanced at my flushed, miserable face and gently stroked my cheek with the back of her hand. “Aww, don’t pout, sweetheart,” she teased sweetly. “By the time we’re done with you, every boy in school will be lining up just for a chance to get into your pretty little panties.”
Becky, who was intent on her job of denuding my leg, broke her silence by breaking into convulsive laughter. “Oh, Brenda, you’re too much!” laughed Becky as she lowered her head onto Brenda’s chest until she exhausted her laughter.
“You’re quite the card yourself,” answered Brenda, joining in her frivolity.
Great, the mutual admiration society between a pair of dominant females.
I let my leg sink back into the bubbly water.
“Hey, I’m not done yet!” Becky said, tugging it back up. "Hold your leg way up high. I need to finish off your thigh.”
I raised it again and dared a quick peek. My lower leg was already hairless. I winced—and of course, Brenda noticed.
“Pretty, pretty,” she teased, drawing out the t sound as she traced her fingers lightly up and down my smooth calf.
I squeezed my eyes shut, hoping to wake up from the nightmare. But Becky quickly brought me back to reality by lightly patting the underside of my thigh. “All done, sweetheart. Now let’s have the other leg.”
I resignedly lifted my left leg. Becky pulled it toward her and lathered it up. Almost seventeen long years to finally grow, I remember thinking, and it was all disappearing at the whims of this fiendish twosome.
As Becky started shaving my lower leg, she addressed me again, with a sparkle in her eye.
“I notice you’ve got some hair on your arms. You need to look pretty when you model your lingerie for us. That means no unsightly hair on the arms. I think you could use the practice, so you’ll be able to do this on your own next time. Brenda, give Blondie the razor—let him do his arms himself.”
“What a wonderful idea, Becky.” They were feeding off each other now. “But he has to ask nicely.”
I stared at them wide-eyed.
“Go on,” Brenda encouraged. "If you ask us very nicely then we’ll let you shave your own arms. If you don’t ask nicely, I’ll take care of it and maybe I’ll snip a few pubic hairs while I’m at it.”
I had reached a new low. Not only was I being rendered hairless, but I also had to beg to do the dirty deed myself. It took some resolve, but I pleaded in the nicest voice I could muster up under the circumstances.
“Brenda and Becky, could I please.…please, may I shave my arms?”
I couldn’t believe the words I had just spoken. Both girls laughed heartily at my latest debasement.
“Of course, darling,” Becky giggled, handing over the razor and shaving cream. “Make your arms silky smooth, just like a good little girl.”
Defeated, I lathered up and began shaving my left arm.
“That’s it, doll face,” said Brenda. “All the way up to the shoulder. We don’t want any stray boy hairs, do we? That’s a good girl, completely hairless,” she purred as I somehow turned a deeper shade of red.
By the time I was finished with both arms, Becky was done with my other leg. Brenda plucked the razor from my hand.
I couldn’t take my eyes off my now-hairless arms. I suppose I’d gotten so used to seeing that light layer of hair every day that the sudden change was a shock to my system. The skin looked so bare, so strangely delicate. It really sank in, in that moment, what they had done to me. I was mesmerized—until I was quickly pulled out of it by Brenda, who noticed my fascination.
“That’s right, sweetheart,” she cooed. “Just like a girlie’s arms. I’m dying to see how your pretty your legs look.”
She reached into the tub and pulled out the plug. The water slowly drained, and the “blub, blub” sound was quite ominous. In desperation, I plugged it with my heel.
“Now, now, Blondie,” warned Becky. “Don’t make me go get the scissors.”
I moved my foot away, and the water again started draining. “Please, you guys,” I appealed. I was near tears. “You’ve done enough, please go away and leave me alone.”
“Why, we’ve got to see the fruits of all our hard labor, don’t you think?” countered Becky.
I lay in the tub, staring at the ceiling, as the water made its inexorable disappearance down the drain. When all the water was gone, my body was covered with a layer of bubbles.
“Stand up, cutie pie,” Becky commanded. "Let’s spray you off so we can see how smooth you are.”
I stood, back turned to them, hands over my crotch. Becky had the hand-held showerhead in her grasp, and I felt the stream run from the top of my head and all the way down to my feet. The girls were oohing and ahhing at the sight.
“Ooh, Becky, great job on the legs! They’re adorable!” said Brenda as I felt her hand running up and down the back of my left thigh. Then, to my distress, I felt her hand running in a circular motion across my butt cheeks. “And his little buns are baby smooth, too What a doll!.”
“I know,” giggled Becky, “And I didn’t even have to shave there.”
While the girls burst into laughter, I stood there, utterly mortified, water streaming down my bare, silky skin. My sister and her best friend looked me over with gloating pleasure, like proud artists admiring a masterpiece they’d just finished.
“Okay, the moment of truth, cute cheeks,” Becky chirped, practically bouncing on her heels. “God, this is fun! Turn around, Blondie. Come on, snap to!" Her voice was sugary sweet, but unmistakably commanding.
I didn’t delay the inevitable any longer. I turned around, my hands still covering myself.
“Arms up high, girlie-boy,” she instructed. I hesitated for a split second.
“Come on, up, up, up!” she insisted, her tone playful but merciless.
With a deep sigh of surrender, I raised my arms over my head. The bubbles still clung to my skin, but we all knew that wouldn’t last. Becky turned to Brenda with a wicked grin.
“Would you like to do the honors, my dear?” she said, offering Brenda the showerhead.
“With pleasure,” Brenda grinned, taking it with glee. She aimed the spray at my face first, letting it cascade down my forehead, across my cheeks, and then over my now embarrassingly smooth underarms—which, of course, drew delighted giggles.
“Oh my god, this is too precious!” Becky squealed, clapping like she’d just unwrapped the best birthday gift ever.
“Doesn’t she have the cutest little clitty?” mocked Brenda. Both girls busted out with laughter at the gibe. I couldn’t imagine feeling more humiliated than I was at that moment.
“Okay, come on out, cutie pie,” Becky ordered, beckoning me with a finger. “Let’s dry you off.”
I stepped out of the tub. It seemed like I’d been in there for days. Brenda was waiting with a fluffy towel and a grin that stretched from ear to ear. She began gently patting me dry, treating me less like a person and more like a pampered little doll.
Their Plans for Me Revealed
While Brenda dabbed at my legs, Becky stood beside me with a glint in her eyes—and then dropped the bomb.
“Guess what, Blondie? We’re having a little slumber party tonight, and I think we might let you provide a little entertainment for us. Won’t that be fun? Joanna will be here, and Marcia, and Cheryl, and maybe a couple of others. You’d better be careful—I know Joanna and Marcia don’t like pubic hair on their young boys.
I froze.
"And if you’re really, really good, we might even invite Mitch.”
My eyes went wide. Becky smirked knowingly.
“Oh, come on. Don’t you think he’d love to see how pretty you look, all smooth and silky?”
I opened my mouth to protest, but no words came out. I didn’t want to even think of what type of entertainment my evil sister was referring to. And the reference to the pubic hair was disturbing. Keeping my pubic hair was the only positive I could take from the god-awful experience in the bathtub.
Brenda hung up the towel as Becky reached for a bottle of body lotion, dispensing a generous dollop into her palm.
“This will make your skin sooo soft. And you’ll smell nice and pretty, too.”
She began rubbing the lotion into my chest and stomach. Already the very feminine scent had taken over the room.
“Hold out your hands, sweet pea,” she said cheerfully.
I obeyed. Becky dispensed another healthy glob into my palms.
“Now rub it into your pretty arms and legs. Really massage it in, okay?”
I did so, and the smoothness I felt by touching myself served as a stark reminder of my new condition. It wasn’t just my appearance that had changed—it was the feel of me. Every inch of my body was smooth, scented, and soft. It was impossible to ignore. As my hands glided over my bare skin, I cringed at how delicate and feminine it felt. The silky texture under my own touch was completely foreign—unnerving, even—and knowing that it was all their doing only made it worse. I wasn’t just humiliated by what they’d done to me….I was humiliated by how it felt.
Brenda leaned in close and sniffed near my chest.
“Oh, Blondie, I’m telling you, you’re going to just drive Mitch wild!”
Both girls laughed heartily and led me out of the bathroom.
The moment I stepped into the hallway, I stopped dead in my tracks.
A full-length mirror.
I stared at my reflection, completely taken aback by what I saw. My skin shimmered slightly from the lotion, utterly bare of hair. I looked....delicate.
Brenda pounced on the moment. She guided me gently toward the mirror, lifting my arms and crossing them above my head. She slid her arms around my waist, cheek to cheek with me as we both stared at my reflection.
“See how lovely you look, sweetie?” she cooed, like she was admiring a piece of artwork.
I couldn’t take it anymore. I let my arms drop and looked away.
Becky took my right hand and started leading me toward her bedroom. “Come on, girlfriend,” she said, almost singing the words. “Just wait till you see what we’ve got picked out for you to wear tonight.”
And somehow, impossibly, I knew....
The worst was still to come.
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Roosevelt Humiliations, Chapter 18

Chapter 18: Spanked and Pantied
Disciplined
I shivered in my nudity as my sister Becky led me by the hand down the hall toward her bedroom. Brenda playfully gave my bare backside a playful squeeze as she walked behind us. I instinctively swatted her hand away, and she just giggled with glee.
The two devilish girls were in their full glory, practically buzzing with delight, while I was sinking deeper into the depths of misery. Every inch of my body—except one very critical area, thank goodness—had been shaved smooth at the hands of the two witches. A scented lotion had been rubbed all over my body, as they seemed intent on humiliation through feminization.
And now I was facing the horror of a slumber party with their friends….with me as the night’s "entertainment." I didn’t even want to know what that meant.
Becky led me into her bedroom and released my hand, leaving me standing awkwardly in the center of the room. My hands immediately flew to cover my crotch.
Becky opened one of her dresser drawers and casually started rummaging through it, like she was picking out socks—except, much to my horror, she was fishing through her panty drawer.
“Let’s see, Blondie,” she said in that syrupy sweet voice. “Since you’re so intent on covering up your little bits, maybe we can help you out….ah, here we go, I think you’ll look quite stunning in these.” She held up a blindingly bright pink pair of panties and stretched them between both hands. “What do you think? Is this your color or what?”
The girls burst into laughter. I just stood there with a distressed, somewhat frightened look on my blushing face. My hands tightened a little bit on my privates, and I bent over slightly from the waist—my body practically broadcasting my shame.
“Please,” I implored. “Don’t do this to me.”
Of course, my appeal fell on deaf ears.
Becky knelt down, holding the panties open at my foot. “Step in, sweetie. Time to get ready for your guests.”
I started to comply—lifting my foot, just barely—before panic took over and I made a break for the door. I must have been delusional to think I could escape from my tormentors.
“I wouldn’t do that if I were you,” Brenda cautioned. “One phone call to my cousin and you’ll find yourself naked in public before you know what hits you.”
I stopped in my tracks. No need to remind the reader about Mitch and his threat. Suffice it to say, it was enough to have me completely under their control.
I turned back around, defeated. Brenda was perched on the bed now, patting her lap. “Get over here, little girly-boy,” she said, like a strict mom calling a naughty child.
I timidly walked over, covering myself the whole time, until she grabbed my wrist and pulled me down over her knees. She didn’t waste a second getting me into position—my bare ass cheeks propped up, as if they were begging to be slapped—and then came the first sharp smack.
To exacerbate my humiliation, Brenda scolded me while she went about the spanking. Methodically, each word coincided with an authoritative slap on my naked behind.
“How dare you disobey your sister like that!” she scolded, each word punctuated by a firm slap. “You should be ashamed of yourself!”
Oh, I was. I was beyond ashamed. And It was really starting to sting.
“Now get your little ass up and put your pretty panties on like the girlie boy you are!”
Count ‘em, that’s thirty-two bare-hand spanks, and they came in rapid succession. My backside felt like it was on fire.
Brenda, who obviously derived considerable enjoyment from her spontaneous discipline session, pushed me to the floor, where I landed in a heap.
I stumbled to my feet, wincing, clutching both ends like I didn’t know which to protect first. I hopped in place a few times, completely involuntarily, which just set the girls off in another fit of laughter.
Pantied
Becky was waiting with the panties, now looking even more triumphant. I approached her and lifted my foot again, resigned to my fate.
“That’s a good little girl, Blondie,” she said with a wink. I winced, both at my submission to being dressed in my sister’s panties, and at the use of the word “girl." Brenda smirked knowingly.
Becky tapped my shin and I lifted my other foot, allowing her to slip the other opening of the panties over my leg. She slowly, teasingly drew them up my legs. Then she let go and just stood there, grinning at me while they drooped around my thighs.
“You’re going to have to move your hands, sweetie, so we can pull your panties up,” she said.
I hesitated, then dropped my hands to my sides, mortified all over again. Even though they’d seen everything already, somehow standing there with pink panties dangling at my knees felt worse. Both girls were loving every second of my torment.
Becky sensed my extreme discomfort and pounced on it. Instead of pulling the panties up, she stood up and put her arm around her fiendish friend. They both stood there grinning at me, their eyes darting from my profusely blushing face to my genitals, to the panties, and back up again.
“Doesn’t she look adorable?” Brenda chirped.
I instinctively reached to cover myself again.
“Uh, uh uh,” admonished Becky, “No touching your little clitty.”
The diabolical girls giggled freely as I slumped my shoulders over the latest disparagement.
“Clasp your hands behind your head,” Brenda ordered. “That way you won’t be tempted to play with that little thing.”
I slowly obeyed, lacing my fingers behind my head. My smooth, bare underarms were now on full display—another humiliating detail the girls weren’t going to ignore.
Brenda slinked up beside me and ran her fingers up my side, then softly strummed my hairless armpit.
“So smooth,” she cooed. “So charming.”
I flinched, bringing my elbow down, which made her laugh even harder. She circled me slowly, eyes roaming over every inch of me.
“Hey Beck,” she called. “Come check out Blondie’s buns—they’re almost as red as his face.”
Becky eagerly joined in. “Oh, yes,” she agreed, rubbing my cheek gently. “And feel how warm they are.”
Now both girls had their hands on me, rubbing and stroking and making smug commentary the whole time.
“And check out his legs,” Brenda added, running a hand up my thigh. “Just look how smooth his pretty legs are.”
Two sets of hands stroked my legs. I winced yet again as I continued to endure the mockery from the relentless twosome. They were having the time of their lives, and all I could do was stand there helplessly, catering to their whims as their little plaything.
The sound of the doorbell momentarily interrupted their fun.
The Guests Arrive
“I’ll get it,” Brenda chirped, already halfway to the door. She turned back with a wicked grin. “Looks like your company’s starting to arrive, sweetheart. I think you’re going to make quite an impression tonight.”
She giggled to herself as she made her way to the front door, leaving me alone with my devilish sister.
“Isn’t this fun, Blondie?” Becky asked as she looked intently at me.
Without waiting for an answer that wasn’t forthcoming anyway, she knelt and pulled the panties the rest of the way up. She gave the waistband a playful snap against my belly, then stepped back to admire her work.
“Oh, too precious,” she murmured, adjusting the lace at the leg openings. “Precious.”
She took my hand and led me toward the mirror. “Come see, Blondie. You’ll just love it.”
I didn’t love it. I looked on in dejection at the sight in the mirror. With my youngish face, hairless body and flat chest, I could probably have passed for a prepubescent twelve-year-old girl if it wasn’t for my boyish haircut.
Becky, meanwhile, was beaming like she’d just won a prize.
Brenda poked her head in. “Joanna and….oh my gosh, how adorable,” she gasped when she saw me. "Joanna and Marcia are here. Want me to bring them in?”
“No,” answered Becky. “Just keep them company out in the living room. There’s beer and Prosecco in the refrigerator, so help yourselves. We’re almost ready. And tell them we have a surprise for them.”
Again they both giggled as Brenda exited the bedroom.
Becky turned to me. “Okay, my dear brother—or should I say ‘sister?’ We’ve got to find you something else to wear. You can’t meet your adoring fans in just your panties, you little slut.” Becky laughed at her own attempt at humor, as I stood transfixed at the mirror, extremely apprehensive about what was to come.
The doorbell rang again. “Oh, that must be Cheryl and Julie,” announced Becky. “You remember Julie, Blondie. She was the salesgirl that was so helpful to you at Victoria’s Secret on our little excursion to the mall.”
How could I possibly forget?
I remained silent and was now downright grim. Becky continued to tease me.
“I know she’ll love to see you in your pretty panties.”
I closed my eyes in anguish. Now there would be six—count ‘em, six girls to harass me.
Dressed for a Slumber Party
Becky opened another drawer and pulled out a long pink nylon nightgown.
“Here we go, pumpkin. You’re going to look just gorgeous in this,” she proclaimed as she held it up in front of me.
She slipped it over my head, and we watched in the the mirror as the hem floated down my body and dropped to the tops of my ankles. She adjusted the spaghetti straps on the shoulders.
“Oh! A perfect fit! You look so pretty in pink!”
I looked desolately at my reflection. My cheeks matched the color of the nightgown.
“Oh, God, Becky, please don’t make me go out there like this!” I could feel the tears welling up in my eyes as I pleaded desperately. “I can’t do this—I promise I’ll do anything. I’ll clean your room for the rest of my life, anything! PLEASE don’t make me go out there!”
With her response it struck me right then that she might be the devil incarnate. “I can have you clean my room anytime I want regardless,” was her icy reply. “Now let’s go, sweetie, we’ve kept your guests waiting long enough.”
She took my hand and pulled me toward the door. I resisted.
“Do you want your bare ass spanked in front of all those girls? Do you?"
I stopped resisting.
"You should be thankful that I was able to find such a pretty nightie for you. You’re the only one properly dressed for a slumber party. Now be a good girl, and let’s go greet your guests. And I expect your full cooperation for the rest of the night. Do I make myself clear?”
I said nothing as I was led out into the hallway. Becky stopped and turned toward me.
“I said, ‘Do I make myself clear?’”
“Yes,” I whispered, staring downward in shame.
Becky smiled in satisfaction at my submission. “Good,” she said. “Now let’s go introduce everyone to my darling new girlfriend. Oh, this is going to be so much fun!"”
While Becky giggled with glee I took a deep breath as we made the fateful walk down the hallway.
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