Betty Pearl's Sissy Stories 20.1
Menu => Active Sissy Stories => Topic started by: sissyboy1212 on October 30, 2025, 06:40:20 PM
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This is the start of another story I've been toying with. It's the first one that I've made some use of AI, which I'm generally very suspicious of.
To be clear, AI is not writing the story, but I'm using it to flesh out some of the detail. Honestly, I find that the AI quickly becomes repetitive and boring, so a real human brain has to actually do the rewriting. Still, it can be a useful tool I think. This is an experiment as much as anything else.
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Introduction: The Cheaters
It was the kind of Monday morning that freshmen tend to dread. Midterms loomed, and the air in Hargrove Hall was thick with anxiety and the smell of energy drinks. Over a hundred freshmen hunched over their desks grinding away on their exams in the huge lecture hall. Four boys sat near each other fidgeting more than most. There was Nate, tall and lean with a perpetually worried brow; Milo, shorter and twitchy, always cracking jokes to mask his nerves; Julian, the quiet artist with a knack for improvisation; and Owen, the one with a stubborn streak and innate skepticism.
The eighteen year-old boys had hatched a scheme the night before—the kind of desperate plan born from too little studying and too much youthful bravado. With a few answers discreetly scribbled onto the inside covers of their battered notebooks and a subtle system of coughs and taps carefully rehearsed, they believed they could outwit the proctors. Perhaps it was the sort of thing that might have worked in high school, when teachers were more overloaded and distracted.
But this wasn’t high school, and the volunteer exam monitors—three sharp-eyed seniors—moved with seasoned vigilance, canvassing the rows with an intensity that left little room for error. Unbeknownst to the boys, all three were members of the Gamma Delta sorority. One of the sisters, perched at the aisle, had already noticed the suspicious glances and muted signals exchanged between the four friends but continued to watch, her gaze coolly appraising. The boys didn’t know it yet, but they were being observed with focused scrutiny.
An hour into the test, as some students were finishing and turning in their papers, Nate took advantage of the students moving around him and tried to signal to Milo. Instead, he met the intense gaze of Madison, Gamma Delta’s president, who raised an eyebrow and jotted down their names. The trap had been set. She and her sorority sisters had been tracking their antics for nearly half an hour, trading glances and silent nods as they pieced together the boys’ strategy.
Madison had watched them with a mixture of amusement and calculation. She found the four somewhat endearing in their futile mischief. Gamma Delta was known for promoting and developing very strong-willed and decisive women. Perhaps, she mused, these boys were ideal candidates for a very different kind of lesson—one that would leave a lasting impression and also provide some entertaining distraction for her sorority sisters as well. In her mind, the wheels were already turning. With a chuckle, she recalled some similar things Gamma Delta had done before.
As the exam wrapped up, the four boys slunk outside, their hearts pounding with dread. Their anxiety deepened when, instead of being summoned to the dean’s office, they received instructions to report to the Gamma Delta sorority house. The stately Victorian building, adorned with pastel curtains and gleaming trophies visible through the windows, stood in stark contrast to the sterile halls of the administration office. The boys exchanged nervous glances, their relief at dodging official discipline quickly giving way to an ominous curiosity about what awaited them.
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Wonderful start. Looking forward to continuation. Sounds like Gamma Delta will soon have 4 new girlyboy maids to look after them.
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The Deal
In the main parlor of Gamma Delta, surrounded by pastel throw pillows, trophies and photos of past sorority classes, the boys stood awkwardly before a semicircle of upperclassmen sorority sisters.
“We could report you for cheating,” Madison began, her voice crisp, “which probably means a disciplinary hearing, possible expulsion, and a permanent mark on your record. Or…” She paused, letting the suspense hang in the air, a mischievous grin spreading across her face. “You can spend a month or so as our ‘Little Sisters.’”
The boys stared in confusion, the words hanging over them like a puzzle. A couple of the boys giggled nervously, adding a surreal undertone to the moment. Nate, sensing how little control they seemed to have, uneasily broke the silence, “Little Sisters?” He didn’t like the sound of that at all. He managed to croak, “What does that mean, exactly?” His voice was tinged with uncertainty.
“It’s really pretty simple,” Madison replied deviously, “For the next month or so, you’ll follow our rules, do as we say, and be good little girls, er... boys.” She rapidly recovered from her verbal slip, “We’ll give you some fun projects to complete along the way and host a little competition every weekend to help you get in touch with your feminine, law-abiding sides!” She continued dismissively, “But we don’t need to worry about all those boring details yet.”
“Feminine sides…?” Julian stammered, the words trembling out, as if hoping the definition would soften with explanation.
“We'll...” Madison started vaguely, “let’s just say you’ll get a rare chance to gain a new perspective and walk in someone else’s shoes… or maybe heels.” Then she admitted, “But, yes… to be honest, we would insist on ‘softening’ your wardrobes a bit.” At this, several of the sorority sisters giggled noticeably. Madison shot them a mild glare, and then she continued, “I confess, as part of the deal you’ll definitely be dressing in a more feminine way, but it’s just clothing after all.” She did her best to minimize the importance of this disclosure, “After all, if you’re going to be our ‘Little Sisters,’ a little initial awkwardness and a few... wardrobe adjustments... shouldn't be a surprise as we try to help you mend your ways.”
Madison quickly tried to smooth this over, “But don’t get your panties in a twist over the specifics. Consider it a golden opportunity for an up-close taste of sorority life while you’re paying off your dues!” She went on, “We have a little scoring system to keep track of your progress as you turn your new page. You’ll keep at it until you collectively earn 1000 points as a group. I bet you’ll wind up having a ball! As long as you play by the rules, it ought to take you about a month.” She added with a grin, “It’s pretty simple. Play nice, get your 1000 points, and walk free with a new mindset on life. Or we could just call the dean right now.”
Her eyes narrowed, “As extra incentive, you’ll also be graded against each other. Whichever of you gets the lowest score each week will be rewarded with some nice additional attention and tasks to help out his peers—think of it as some extra tutoring for the slowest learner.”
Madison winked at Julian, then asked with mocking admiration, “Apropos of nothing whatsoever, sweetie, have you ever worn a dress?” she added with a wink, “I bet you’ll be gorgeous!” Julian could only gulp, wishing he could shrink into the nearest pillow.
Owen, shoulders hunched defensively, muttered, “Isn’t that kind of thing—against the rules?” His voice was barely audible, as if he already knew the answer wouldn’t matter.
Madison shrugged with theatrical indifference. “It’s not my first rodeo, boys. Cheating is against the rules too, and the dean loves us. Of course, it’s your call.” Her final words were confident and almost nonchalant, “This way you can learn a little more about women and keep the administration out of it. You’ll practically be getting a free pass!”
Milo, trying to appear confident, blurted out to the others, “How bad could it possibly be?”
Instantly, the sisters erupted in laughter, while Tara, eyes twinkling, leaned closer and inspected Milo’s hands. “It won’t be bad at all, sweetie! Actually, those paws look overdue for a nice manicure anyway,” she teased. Milo swallowed hard, already regretting his question as the laughter around him grew louder.
As the boys’ resistance seemed to crack, Madison stepped closer, her gaze playful but sly as she thrust one more verbal dagger. “Oh, and one more thing,” she said, her voice suddenly softer but no less commanding. “I’m willing to bet—” her smile widened, eyes twinkling with mischief, “—deep down, that at least one of you is going to get a little thrill out of this. You might even find the answer to a question you were afraid to ask.”
At that suggestion, the boys froze. Nate’s face turned scarlet from his neck to his ears, Milo’s mouth hung open in shock, Julian fumbled for words and stammered, “N-no, that’s not—” while Owen’s jaw clenched so hard it was a wonder he could speak at all. Their attempts to protest only made them stammer more and blush brighter, setting off another round of giggles from the sisters.
The boys felt the walls closing in. Their collective resistance seemed to wilt in the face of Madison’s confidence. One by one, desperation etched on their faces, the boys nodded. Owen, jaw clenched and eyes darting, hesitated the longest, but trapped and outnumbered, he relented. The deal was struck, and the sisters smiled mischievously.
"Excellent!" Madison said confidently, "You Darlings come back here tomorrow afternoon, and we'll get things started!"
At this, several of the other sisters started giggling again. Something about the way she said "Darlings" seemed to amuse them. This time, there was no reproving look from Madison.
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Meet the Big Sisters
The next afternoon, Madison gathered the boys in one of the smaller rooms of the house and introduced them to their new mentors—sorority “Big Sisters” charged with guiding their journeys. The power dynamics were established right off the bat, and it was clear the Big Sisters were in charge. Nate was paired with Cassidy, a fashionista with a dazzling smile and a penchant for pep talks. Milo met Tara, Gamma Delta’s resident prankster, who appeared to see through his false bravado immediately. She looked as though she’d take nothing at face value and would not hesitate to keep him in line. Julian was assigned to Elise, a patient artist with an eye for style. She looked him over with appraising eyes, already seeming to envision changes. Owen, still bristling, found himself under Brianna’s supervision. As he would soon learn, her no-nonsense attitude rivaled his own. Her piercing stare seemed to dare him to defy her.
The Big Sisters quickly set aside the vague euphemisms Madison had used the day before. They made it clear that dresses, panties and many feminine things would become their new reality. Embarrassment bloomed as the sisters began to explain some of the month’s schedule. Lessons in clothing, makeup and deportment loomed. The confident sorority girls began detailing a list of mandatory requirements and activities the new “Little Sisters” would complete. Any illusions the freshmen boys held about how easy this would be were instantly shattered. The boys shifted uncomfortably as reality sank in.
Madison, acting as though this was exactly what she’d described the day before, advised them condescendingly, “I think you’ll find the best thing to do is just follow instructions, but I’m sure some of you may have to learn the hard way.”
Tara explained further, “Now on weekdays, you’ll keep up with your classes and studies, but don’t think you’ll be slacking off. You’ll need to manage your time wisely, and you’ll be checking in with us all the time.” She went on, “Of course, as your Big Sisters, we are here to help, so on Tuesdays and Thursdays you’ll have mandatory study halls here with us at the house so we can keep you on track… starting tonight." She continued, “and that’s also when you’ll get to learn all about Gamma Delta… you know… our history, our founding members, dates, names and other important facts.” She chuckled, “We’ll have little impromptu quizzes all the time to give you chances to earn more points. You’ll be at 1000 before you know it!” Her cheerful delivery only made the boys feel more out of their element, like schoolchildren sent to the principal’s office.
Cassidy interjected, “Rest assured, we’ll keep close tabs on you even when you’re not at the house.” she continued, her voice tinged with humor and authority, “But be sure to clear your weekend calendars, boys, because Saturdays and Sundays are reserved for us—and trust me, you’re going to be busy!”
Elise chimed in, her words soft but firm, “Every Sunday, we’ll have an exciting contest to cap off the week. I promise it’ll be wonderful fun! You’ll get more details as we go along—but you’ll want to bring your A-games.” Her description of “wonderful fun” felt ominous. None of the boys thought they would enjoy her idea of “wonderful fun.”
Then Madison warned, “But slipups and lack of effort will cost you points. We’re strict, but fair. And we do want you to succeed.” Then she pointed out a whiteboard hanging in the parlor with all their names on it, “But you’ll need to catch on quickly, or the scoreboard won’t be kind.” The boys each stared at their own names posted in glittery pink letters, dread settling in their stomachs.
The implications were obvious—their progress and missteps would be on public display. An uneasy silence settled over the boys. Everything suddenly felt more real, and their nervous faces showed it. As the increasingly worried boys listened, their Big Sisters continued to lay out expectations that seemed to multiply by the minute.
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Delightful. Sounds like the 4 'Little Sisters' are going to be taught how to bring out their feminine sides with pretty dresses and cute frilly knickers or regulation school knickers as well as make up and manicures. Looking forward to continuation.
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This already is a wonderful story developing
Thank you so much for your great writing
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The intrepid quartet seems destined for the ultimate in humiliation and embarrassment since they have been portrayed as highly gullible. After all, Madison has not provided any hard proof (written codes [no mention of answers scratched in notebooks], answers written on clothing, body or paper, etc) of their cheating and any accusation would be one of he said/she said. Overall, the "cheating" seemed to be quite abstract at best. Too little evidence to warrant expulsion or notation on a transcript. They capitulated too quickly and will now pay the price for their lack of confidence, not for their cheating.
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LOL babycakes. As they say, my best advice is to "suspend your disbelief" :)
If you pull too hard on the threads of this story, it's going to quickly unravel! Thanks for the comment and I hope you enjoy the somewhat preposterous ride!
xoxo
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babycakes in top form! Nice response, sissyboy.
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Yeah... I already know this story is ridiculous, but I'm choosing to wallow in the absurdity.
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First Steps
Next, each boy was gifted a journal with a pink sparkly cover and his name written in fancy script across the front. “Every night,” Cassidy declared, handing out the journals with dramatic flourish, “you’ll write a page about your day, what you learned, and how you felt—no slacking, and don’t even think about skipping! We want real reflection, not just ‘I survived another day.’” They learned their journals would be reviewed every Friday, and points would be on the line.
Cassidy dropped another bombshell, “You’ll also be super involved in helping plan our Gamma Delta Alumnae Luncheon on homecoming weekend.” She produced a tabbed binder filled with guest lists, seating charts, theme and centerpiece ideas, menu options and all sorts of other planning details. “And of course, you’ll all get to help serve and host on the day of the event!” she added with an expectant smile, “It’s going to be fantastic!”
Then Elise gave them all a little white bag with pink tissue paper sticking from the top and said, “These are starter kits for your new skincare routines.” They groaned inwardly as she gave them a short demonstration, lining up a little row of cleansers, toners, serums, and lotions in pastel bottles. “No more just splashing water on your faces,” she tutted, showing them how to pat, not rub. “Details matter, boys,” she declared.
Just as the boys were still processing their skincare kits, Brianna, with a knowing smile, gestured back toward the little white bags. “By the way, don’t forget to check your bags for your new diet guidelines,” she announced brightly, “From now on, you’ll be eating much healthier!” Brianna’s tone was cheerful but left no room for negotiation. “Gamma Deltas strive for glowing complexions and feminine figures, so you’ll be leaning into fresh salads, yogurt, herbal teas, and other nutritious food. You’ll kind booklets with menu suggestions and sample meal plans, and we expect you to follow them.”
She continued, circling the group with her hands clasped behind her back, “That means no more candy bars, sodas, chips, or fatty fried foods! And you can forget about those late-night pizza runs freshmen boys are notorious for!” Brianna gave them a wink, “Of course, points will be on the line if you’re caught backsliding.”
Their new Big Sisters had a final gift for them. Each boy was handed another daintily wrapped package. The packages were wrapped in delicate tissue paper tied with charming pink ribbons, and each of their names was written in glittery calligraphy on their package. Tara directed them, “All right, boys—open your presents!” Timidly, they each untied the pink ribbons and peeled away the tissue paper, revealing adorable matching bralette and panty sets. The undergarments were crafted from silky white satin, finished with delicate pink scalloped trim that added a lovely, feminine touch. Inside each package they also found another weird looking pair of underwear briefs with a lot of padding and stretchy material. All these briefs were in a subdued nude shade.
Cassidy explained, “In case you don’t know, those are dancer’s belts.” She continued, “They have extra padding and compressing spandex to uh… flatten you out in front.” The other Big Sisters all giggled as she spoke.
Tara added mischievously, “That’s right! We can’t have any unsightly bulges on our darling new Little Sisters!”
Brianna chimed in, “You can lose all your grimy boys’ underwear, because you won’t be needing it anytime soon! You’ll be in your pretty panties and bralettes along with your dancer’s belts from now on! Demure and delicate… that’s the Gamma Delta way!”
Madison smiled sweetly and went on, “That’s right. Of course, these are just to get you started. You’ll obviously need to make more room in your lingerie drawers since you’ll be wearing panties and bras every day.” She added, “But don’t worry, we’ll show you where the dance supply shop is downtown so you can go buy all you need,” Madison finished, “and your Big Sisters will advise you on the best places to find pretty unmentionables in your sizes. That way you can stay fresh as daisies all the time!”
Madison added with a knowing smile, “You’ll learn more tonight about wardrobe requirements.” Her tone was cheerful but hinted at more surprises to come, leaving the boys with a fresh wave of apprehension.
The boys exchanged uneasy glances as they realized they would have to shop for their own lingerie. The idea of browsing racks of delicate bras and panties made them feel embarrassed and out of place.
Finally, Brianna announced that on Saturday they could look forward to a makeover “field trip”—details to follow. The prospect unsettled all four boys even further, and the looks on their faces seemed to protest. Brianna preempted their silent objections with a firm wave of her hand. “Part of the experience,” she said in a tone that invited no discussion, “Presentation is everything!”
Nearly overwhelmed, the boys stood in silent disbelief, cheeks burning as the Big Sisters watched with bright, approving smiles.
Madison said with a teasing giggle, “Well that’s enough for now, but as you can see we’re going to have a blast!”
Then Tara grinned mischievously, “And there’s no time like the present to get started! Go ahead and put on your pretty new things, boys!” she announced. With teasing glances and playful winks, the sisters swept out of the room, leaving the boys alone to change reluctantly into their dancer’s belts, panties and bralettes.
As the boys left the sorority house, they were all blushing fiercely and walked almost gingerly. They all felt so vulnerable and self-conscious with their unfamiliar new lingerie under their normal clothes.
Watching them leave, Madison called out with a smirk, “You all look much more ladylike already!”
“See you tonight at study hall, fellas!” Tara added gaily, “Enjoy the rest of your afternoon!”
“What have we gotten ourselves into,” Nate asked aloud in a worried voice.
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Apologies, Sissyboy. Never meant to criticize the story. Writing is time consuming and challenging, especially to produce a quality piece such as this and your other work. Previously forgot to note all your effort is greatly appreciated and of course this story, as with others in the genre, requires a suspension of disbelief as it is a fantasy after all.
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No apologies necessary babycakes. Thank you for your comments, and I didn't take them poorly. They were very fair and not unkind. I enjoy getting comments as long as they are polite and fair, even if people may not like aspects of the work.
FYI I did decide on this story to skip an involved setup in favor of jumping right to the more interesting stuff, so the premise is admittedly flimsy :)
xoxo
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Wow!! the 4 little sisters are now fully trapped. I assume that they are all room mates otherwise it would be embarrassing trying to change wearing their new pretty lingerie. Looking forward to when they go shopping for new lingerie, frilly and french knickers?. I think the sales girls are going to have wonderful time humiliating and embarrassing them choosing the cutest and frilliest matching sets.
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Study Hall Dress Code
The last rays of the afternoon sun cast long beams on the Gamma Delta house as Nate, Milo, Julian, and Owen approached the house together. Their nerves fluttered in anticipation, and the feel of their lacy undergarments were a constant reminder of their predicament. The front door swung wide before they could knock.
Tara and Brianna greeted them, their eyes sparkling with anticipation. “Welcome, Little Sisters!” Tara announced, her voice ringing with good-natured mischief. “We’re so glad you’re here on time. That’s the Gamma Delta spirit!”
The Big Sisters wasted no time in ushering them to a second-floor room where Madison, Cassidy and Elise were already waiting. “Tonight,” Elise informed them, “you’ll be learning how Gamma Delta scholars present themselves. That means dressing appropriately—demure, tidy, and, of course, adorable!” Her wink was conspiratorial.
Madison announced, “We’ve put together some nice ‘study uniforms’ for you. We don’t allow slouches and slobs in the halls of Gamma Delta!” The boys stared, wide-eyed, at the four matching outfits hanging before them. Nate swallowed hard, and Milo’s mouth fell open. Julian nervously fiddled with the strap of his messenger bag, and Owen let out a tiny, incredulous snort. It was immediately obvious that things were getting real now.
“You mean… even for doing our homework, we have to wear—?” Milo began.
Madison cut him off with a teasing smile, “That’s right! Skirts, blouses, tights, the whole ensemble. Oh, I promise you’ll get used to it before you know it.”
“Don’t worry,” Cassidy soothed, “we’re going to help you get ready.” The girls each took charge of their new Little Sister and set to work. The boys were issued delicate white silk blouses with peter pan collars and pearl buttons. Knee-length, pleated navy skirts and creamy white tights came next. These were followed by cute ballet-style navy flats with modest heels.
The process of getting dressed was awkward, slow and embarrasing. Nate fumbled with the tiny buttons, his fingers clumsy at the unfamiliar task. Milo held up his skirt uncertainly, as if double-checking how it was supposed to fit. When he pulled his tights up, Julian took a moment to smooth them over his calves, his cheeks burning and his skin tingling with the new sensations.
Once Owen had his blouse on, he pouted at his reflection while Brianna briskly adjusted his collar. “You look darling,” she teased, “very scholarly chic.” Owen then quickly looked away from the mirror with his lips pressed tight. It was almost as if he saw something that frightened him.
Madison said playfully, “Now that you’re all dressed to impress, it’s time for hair!” Elise pulled out a large bin of hair accessories they had obviously gathered for the occasion: pearl and silver barrettes, tasteful hair clips, hairbands in velvet and satin. There were also plenty of combs, brushes and styling products.
Cassidy started with Nate, assessing his thick hair with a discerning eye. She worked in a modest amount of mousse, taming his flyaways with gentle brushstrokes. She swept his bangs to one side and pinned them with a pair of pearl barrettes, creating a cute, feminine fringe. She then brushed the sides back nicely away from his face.
Tara spritzed Milo’s curly hair then worked in a dab of smoothing cream. She used a comb to coax a few curls to sweetly frame his forehead. Parting his hair off-center, she pinned each side with subtle, silvery barrettes. Looking in the mirror, Milo cheeks tinged with surprise at how different he looked.
Elise took charge of Julian and brushed his blonde hair out thoroughly. After applying a touch of product, she parted his hair neatly down the middle. Then, she swept the sides back and tucked them under a slender navy headband. She used a few pins to hold things in place. Then, she tugged gently at the ends to soften them into gentle wisps. “That’s kind of cute,” she said sweetly.
Brianna took on Owen, whose dark hair was longish and straight. She used a dab of styling wax to smooth his hair into a gentle side part. With a little more product, she teased the front into a slight wave added two gleaming silver clips just above his left temple, anchoring the style in place. Owen grunted as he saw himself, but the result was undeniably presentable and feminine.
The boys were amazed at how quickly the sisters had conjured feminine hairstyles out of their unruly mops. “Not bad for the first try,” Madison declared. After a moment’s pause, “Now, for makeup!”
Tara produced a caddy of makeup brushes and shimmery compacts. “Just a touch—mascara, a hint of blush, and a little gloss,” she said, “At Gamma Delta, we always put our best face forward.”
By this point, the boys were no longer protesting. Still, the unsettled looks on their faces spoke volumes. Madison simply grinned and assured them, “It’s all about poise and presentation, and it’s part of our deal.”
“I hope you’re paying attention,” Brianna warned, “soon you’ll be doing all this yourselves!”
Nate’s lashes were brushed lightly, his green eyes framed with unexpected elegance. Milo wriggled nervously as a dab of pink blush brought out the color in his cheeks. Julian sat very still, eyes wide, while Elise traced a glossy tint over his lips. Owen sat quietly while Brianna gave him a quick flick of mascara and a dusting of powder.
In a short time, they blinked at their reflections in amazement and ogled each other. Despite themselves, they realized that they all sort of looked… pretty. Confusing emotions stirred in them all, ranging from nervousness to embarrassment and even to a bit of excitement.
“Well,” said Madison, stepping back to assess the Big Sisters’ efforts, “I do see some promise.”
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A Surprise Detour
The boys barely had time to adjust to their new looks before their Big Sisters gathered around them with an air of excitement. Madison clasped her hands together eagerly, drawing everyone’s attention. “Just one more small thing before study hall,” she announced, eyes sparkling. “Tonight, we need you to take a little pledge so we can make your new ‘Little Sister’ status official… to ‘seal the deal’ so to speak. I’m thrilled that you’ll get to be part of our Gamma Delta tradition!” The boys exchanged bewildered glances, their nerves already on edge after their rapid-fire makeovers. Nobody had mentioned anything about a pledge before.
“Don’t look so nervous, boys!” Madison addressed them again, “all we’re doing is formalizing the agreement you already made to be our honorary Little Sisters.” She went on casually as if this were a perfectly normal and routine thing, “This is just a fun way for you to meet all the other Sisters and let them understand the deal we have.” Her efforts to downplay it all did little to allay their concerns.
Before they could gather their wits to protest, Tara said gently but firmly, “Let’s make sure you’re ready.” In the next instant, they were practically swarmed as their Big Sisters swooped in on them to do final checks. The Big Sisters straightened blouses, smoothed skirts and adjusted barrettes to ensure their Little Sisters looked perfectly presentable—if a bit shell-shocked. Cassidy gave Nate another quick dusting of rosy blush, and Brianna warned Owen to be still while she applied another shiny coat of pink gloss to his lips. With the last touchups complete, Madison gave an approving nod, and the Big Sisters formed a loose, almost protective, circle around their charges.
Before they departed the room, Madison had a few final words, “Now, you’re going to hear some fancy language when we go downstairs. As you might suspect, like all Greek organizations, we have our own rituals and traditions. And like all the rest, we tend to lean into ‘Greek-speak’ now and then.” With a bit of a chuckle, she added “We sorority girls love our pageantry… just try and put on a good show!” She winked at them playfully. Then, the Big Sisters began ushering them out of the upstairs lounge and down the wide staircase.
The short journey downstairs felt surreal. As they descended, their Big Sisters walked beside them, offering encouraging smiles and subtle giggles that only heightened the boys’ sense of anticipation. Downstairs, their shoes clicked softly on the polished floor, and they reached a set of double doors.
Madison knocked on one door with two precise raps, and they silently swung open as if on their own. The flustered boys were led into the main hall of the sorority house. The room was softly lit, and several candles glimmered around the room. Their stomachs began to do backflips as they were marched into the center of the room before the entire Gamma Delta sorority! The rows of Sisters buzzed with excited whispers and a sense of anticipation.
The boys’ embarrassment was acute. They felt painfully exposed with their freshly made-up faces obvious under the soft light. Every dab of blush and touch of mascara made them feel more vulnerable. They were so self-conscious in their delicate blouses, pleated skirts, creamy tights and sparkling barrettes. Being suddenly thrust into the spotlight like this made them want to melt into the floor. Their cheeks flushed and their hearts raced, but there was nowhere to hide.
Holding up her hand, Madison stepped forward and motioned for the boys to stand in a line at the front of the room. Their Big Sisters flanked them, each with a hand resting on a shoulder or elbow to guide them. Their touch was kind but controlling, a subtle reminder of their new roles and who was calling the shots. A hush fell over the room.
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I really like the neatness of their study outfits. It shouldn't be too difficult for them to become accustomed to such nice formal clothes, and be seduced by their comfort and practicality. I hope so, anyway...
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( " at " ) Simonssister - Thanks. You might like to know that you inspired the AI image of the study outfits. I think the ones you have done in "His Aunt Nicole" are cute as well, and I decided to try one.
Glad that you approve!
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Delightful. Loved the photo of the 'Little Sisters' so cute and demure in their school uniforms. Now that they are being introduced to the rest of the Big girls I think their humiliation and embarrassment is just beginning. Wonder how they will be dressed when they go shopping for their pretty frilly and lacey lingerie?
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The Pledge
Madison began to speak in a dramatic tone, “Tonight, we are all privileged to witness a rare ceremony. The candidates before you will make their solemn promise to Gamma Delta... in the Alexionian Society.”
At the mention of the Alexionian Society, an audible wave of excitement and anticipation seemed to sweep through the gathered Sisters. The air was suddenly electric. Members exchanged excited, knowing glances. Several clasped their hands in eager energy, and they all appeared to be fully aware of something significant about to unfold.
Watching this reaction, the four emasculated boys stood frozen at the front of the room, their faces pale with apprehension. They were incredibly confused and mortified. Still wildly uncomfortable in their new feminine skins, each boy felt the weight of curious, excited eyes upon them. They felt incredibly self-conscious of their lacy undergarments and confining dancers’ belts. Their glossy pink lips shone so daintily in the candlelight and seemed to only highlight their embarrassment. The delicate fabrics of their clothing rustled sweetly. Their crisply pleated navy skirts contrasted demurely with the creamy sheen of the tights that clung snugly to their legs. Their patent Mary Janes gleamed brightly with every nervous fidget. Their hands fidgeted with the hems of their skirts or the edges of their silky cuffs, seeking some comfort in the unfamiliar attire, but finding none.
Their hearts continued to pound, and every whispered giggle from the crowd only intensified the boys’ sense of vulnerability.
Madison, sensing she had the room in the palm of her hand, savored the moment. She continued theatrically, “This pledge marks their formal commitment to our sorority and everything we stand for.” With added seriousness, she explained, “Although we refer to them informally as our ‘Little Sisters,’ they are in actuality joining the ‘Alexionian Society.’ The Society holds a beloved place in the traditions and history of Gamma Delta. Its name calls back to the ancient Greek ‘alexis,’ meaning ‘helper.’ The Alexiones play a gentle, supportive role in our Sisterhood as our devoted and faithful helpers. The Alexionian Society is incredibly exclusive. In our history, Gamma Delta has often had years where no new members of the Society were inducted. Even in our chapter here, it has been over three years since our last.”
She let that sink in. Then she announced, “Tonight, we welcome these four… yes, I said four… new members of our cherished Alexionian Society.”
The excitement in the crowd was electric.
With a commanding presence, Madison turned toward the four flustered college freshmen. Like deer caught in the headlights, they froze. The unspoken question was obvious in their panicky eyes, “The Alexionian Society…?”
“Raise your right hands and repeat after me,” Madison instructed, her tone serious and dramatic.
The boys hesitated under the scrutiny of the entire sorority, hopelessly searching one last time for an escape. Instead of a way out, however, they saw several Sisters with their phones out taking pictures and videos! The room was silent, and the tension for the four boys was excruciating. The psychological pressure on them to comply was intense, and they felt like an invisible net had suddenly tightened over them. This net had been crafted throughout the evening: Their rapid feminine transformations, the insistent guidance of their Big Sisters, the overwhelming attention to their appearance, the parade through the house, the suspenseful build-up. Each act of compliance whether it was meekly getting dressed, sitting still for makeup, or allowing themselves to be led like children had put them more off-balance. All of it had landed them here. Now, under the glare of the spotlight, there only seemed to be one path forward.
Then, each of them received a firm, purposeful squeeze of the shoulder from his new Big Sister. Once the first hand began to move, the rest followed. One by one, Nate, Milo, Julian and Owen slowly raised their nervous hands as directed.
Madison read the words aloud, clear and steady. She paused after every line for the boys to repeat:
“I solemnly swear to the Sisterhood of Gamma Delta my steadfast devotion as a member of the Alexionian Society. Grateful to be given the privilege of service, I vow to respect and follow Gamma Delta’s values. I will embrace chastity, modesty and grace in all things. I will ever seek to embody kindness, obedience and loyalty. These things I pledge with all my heart, and all my soul, to the Sisterhood of Gamma Delta.”
Each boy repeated the pledge, voices quiet and uncertain, as phone cameras flashed around them. Milo’s cheeks burned as he stumbled over the words, and Owen’s voice wavered. Nate spoke so softly he could barely be heard, and Julian’s eyes darted to the ceiling, wishing he could disappear. Their embarrassment was palpable. They’d never felt so exposed. In particular, they all seemed to choke a bit as they promised to “embrace chastity!” They felt so helpless as the walls closed in. It was only made worse knowing that every stammer and blush was being recorded for posterity. But as their last words faded, a wave of applause mixed with some laughter began sweeping through the room.
Some sisters cheered, clapping loudly and calling out praise. “Well done, Little Sisters!” someone shouted. There was teasing too. Elise winked, “Congratulations! Now you’re really in it!” Cassidy giggled, “That’s just the beginning, boys!”
Overwhelmed, the boys stood meekly as a cheerful wave of girlish affection swept over them. They received hugs, gentle pats on the back, and many ultra-feminine air kisses so as not to smudge their makeup. More than one gentle hand glided across the boys’ backs during a hug to intentionally trace the slender lines of their bra straps underneath as if doing an inspection. The air was thick with perfume and laughter. Their faces were still flushed with embarrassment, and they were disoriented by this sudden outpouring of congratulations. Their cheeks grew even rosier at each dainty “mwah!” of another sister’s air kiss wafting by their cheeks.
The boys began catching snippets of conversation that hinted of worrisome things to come. They heard more than one Sister refer to them as “Darlings,” and a couple of Sisters said they “couldn’t wait until Sunday!” The atmosphere turned almost playful, but with an edge.
It also unnerved them that more than one Sister commented on their feminized looks. Nate overheard a pair of Sisters whisper about, "those adorable cheekbones!" Milo caught a comment about "that gorgeous hair.” Julian tried not to react when one Sister said he was "too pretty to be a boy." Owen blushed to hear "His lashes are unreal. Jealous!" Each remark only amplified their discomfort, and they felt like ornaments on display. Surrounded by all these confident Sisters while dressed in their delicate skirts and blouses left them feeling outnumbered and exposed.
As the ceremony mercifully drew to a close and the room slowly emptied, their Big Sisters gathered them together and led them upstairs with gentle, guiding hands. “Now,” Tara announced with a sparkling smile, “It’s finally time for Study Hall!”
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Talk about "out of the frying pan, into the fire"! Wonder when they'll realize they pledged unending (?) servitude/slavery (with fur lined shackles) to their big sisters? Of course the sisters are excited. They haven't had male maids in four years.
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Delightful. Now that the 4 'Little Sisters' have ben inducted into the newly resurrected Alexionian Society will they now be deemed to be the new 'Handmaidens' of the 'Big Sisters' of Gamma Delta and pander to their every wish and command? Will they also have a new dress code?
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Study Hall
As they entered the study lounge, they saw some of the Sisters were already there to begin work on their own studies. The air was still charged with excitement following the drama of the ceremony a few minutes before. Madison quietly announced to the room, “Our new Little Sisters will be joining us for their first study hall this evening.” The boys filed in, their movements careful and almost fragile as they clutched the unfamiliar folds of their navy skirts. Their nerves were still raw from the ordeal downstairs, and as they entered the boys were enveloped by a scene that practically sparkled with feminine energy.
There was another soft ripple of laughter and some delighted murmurs from the sisters scattered at nearby tables. One girl noted again, “They look so cute, and those skirts are just everything!” Another chimed in, “Absolutely precious! Just look at those fresh faces.” They were all clearly still amused by the spectacle of these new Little Sisters.
Unsettled and embarrassed, the boys blushed under the collective gaze. Their clingy tights and delicate blouses made them feel so feminine and exposed. They cringed in embarrassment. They had so many questions, but they were afraid to speak. They knew it was time to hit the books.
Soon, the Gamma Delta study lounge buzzed with gentle energy as all the sisters resumed their own work. The walls were hung with photographs—groups of sisters posing happily, celebrating victories and offering silent proof of the sorority’s spirit of camaraderie. The boys found their places at a large round table. With their notebooks and textbooks arranged before them, they tried to study. Their darling clothes and the subtle fragrances of powder and lip gloss kept their senses on edge.
Madison told them quietly, “Our study hall isn’t just about homework. It’s about supporting each other, asking questions, and learning together. Gamma Deltas always help their Little Sisters succeed.”
The boys shared a collective grimace but tried to tackle their homework. Dressed as they were and still unsettled by the shock of the ceremony, they found it nearly impossible to concentrate.
Nate found himself tugging discreetly at the edge of his navy skirt, hyper-aware of how his tights hugged his legs. Several times, Tara had to tell Milo to stop fidgeting with the collar of his airy blouse which earned him embarrassing glances from the assembled sisters. Julian restlessly shuffled his ballet flats against the carpet. Owen sat more rigidly. He was acutely aware of his delicate makeup and feminine clothes, and his discomfort was obvious.
As the Big Sisters tackled their own coursework, they occasionally floated from seat to seat and offered help with tricky math problems or essay outlines, perfume swirling in the air. Between whispered hints and sweet giggles, the Big Sisters found countless little excuses to dote on their new charges.
During the course of study hall, the Big Sisters made sure each boy got to experience a quick “lip gloss refresh.” Periodically, Madison would quietly tap a shoulder and gesture to a Big Sister, and the selected boy would be gently but insistently escorted to a pastel ottoman in the far corner. It was placed in a spot painstakingly chosen to ensure maximum visibility from across the lounge. Each boy was then instructed to sit with his knees pressed together and hands folded daintily in his lap. During these little moments, each boy blushed brightly as his Big Sister smoothed another shimmering layer of gloss onto his lips under the cringing gaze of his peers and all the other Sisters. Sometimes, the Big Sister would tease by pausing dramatically, holding the boy’s chin with gentle fingers and tilting his face so everyone could watch his transformation. The ritual left them squirming in embarrassment, their lips shiny and sweetly scented.
Despite it all, the boys began to relax slightly, and they were somewhat surprised to find that the Big Sisters seemed genuinely interested in their academic progress.
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Looks like the 'Little girls' are becoming more resigned to their new roles. At least the 'Big Girls' of Gamma delta have confined themselves to only mild teasing and seem happy to assist them in their studies. Wonder how long it will last?
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A Gamma Delta Primer
When the hour reached eight, Madison cheerfully announced that it was time for the boys to get their first lesson in the history and lore of Gamma Delta. Most of the other Sisters in the room turned their chairs to watch. Madison then produced a neat stack of study packets. The booklet covers were stamped with the sorority crest, and she distributed them with the flourish of someone unveiling treasure. Her voice took on an air of ceremony. “Tonight, you’ll begin to appreciate what it means to be part of the Gamma Delta fold. This isn’t just a sorority—it’s a tradition, a legacy, and a family. And as our Little Sisters, the newest members of the Alexionian Society, you are going to learn all about our history, values, and what makes Gamma Delta special.”
The boys exchanged pained looks as their Big Sisters gathered around, ready to guide where needed. Madison’s tone grew even more serious as she continued: “I want you to understand that starting now, you must apply yourselves with the utmost diligence. Mastering all the material in these packets is not optional. You will be expected to know by heart every aspect of Gamma Delta history, tradition, and lore.”
Madison let that sink in, and then she began the lesson, her tone serious. “Let’s start with our motto: ‘Sisterhood in Service and Strength.’ It’s more than words. It’s a promise that every member supports one another and works toward bettering themselves and the community.” She pointed to a banner overhead, where the Greek letters "Gamma" and "Delta" were displayed in elegant gold script. “Gamma Delta—those letters stand for ‘growth and change,’ the twin pillars upon which all our rituals and goals rest.”
Madison then instructed the boys to open their packets to the first section on Gamma Delta’s core values. She read aloud, “The five core values of Gamma Delta are Service, Integrity, Growth, Unity, and Leadership. Each value guides the actions, traditions and expectations for every Gamma Delta.”
The boys saw that each value was accompanied by a section on its importance and application. Every value also had a corresponding set of reflection questions, which, Madison explained seriously, they would answer in writing and turn in by next Monday. The feminized college boys seemed to deflate as their workload grew, and they looked adorably restless. Before moving on, Madison said firmly, “Take your responses seriously.” She warned. “You’ll need to put real thought into your answers, because points will be at stake.” The boys exchanged more uneasy glances.
Cassidy then spoke, “Our traditions are so very important.” She continued gaily, “In your study guides, you’ll learn all about the symbolism behind our colors—rose pink and silver. You’ll understand why our official flower, the cream-colored rose, embodies the Gamma Delta spirit. You’ll also find in your handouts the lyrics for our official hymn, ‘The Shining Eyes of Gamma Delta.’”
Fumbling in his booklet, Nate found the page detailing the sorority’s song, complete with annotated sheet music and suggested choreography.
“I highly suggest you begin memorizing the words right away,” Cassidy advised them. Then she added with a wink, “But don’t worry, you’ll be singing it by next Thursday.”
Nate practically winced as he scanned the extensive performance notes.
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Oops!!. Seems there is more than anticipated to becoming a 'Little Sister' of the Alexionian Society. Wonder what the punishment is for failing any of the courses. Humiliating I should think. Look forward to next episodes.
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Becoming Delta Darlings… and a Warning
The boys then learned more about the Alexionian Society they had just joined. They were told it was also occasionally referred to as “The Society of the Alexiones.” They soon realized they were far from the first college boys to become reluctant Little Sisters. Almost all the “Alexiones” before them had been “drafted” in one way or another. In addition to being knowledge experts on Gamma Delta, their new role was to be “helpers” for the Sisterhood in a variety of ways. It seemed their central role was to provide cheerful, diligent service supporting the ideals of Gamma Delta.
Madison explained that their service could encompass a wide range of activities—academic work, errands, charity work, occasional chores and even… entertainment. When she mentioned that last one, her lips curled in an almost devious way. The boys squirmed, worried about what was to come and acutely aware of their feminine skirts and blouses.
Madison continued, “You’ll be expected to embody service with grace, and of course, you won’t be joining any of the fraternities.” The boys were somewhat dismayed to learn that. Madison added succinctly, “You’re on a different path now, and anyway you won’t have the time.” Although Julian had no plans to join a fraternity, the other three had harbored various levels of interest. They felt a small pang of loss to have those aspirations squashed so dismissively and decisively.
As Madison outlined their new roles, the boys shifted uncomfortably in their seats, feeling the soft fabrics slide against their skin as constant reminders of how their world had changed. They discovered that the oath they took was formally called the “The Alexion’s Pledge.” Apparently each of them was now officially an “Alexion,” together they were “Alexiones,” and they had joined the “Alexionian Society” It was a lot to keep straight. They also learned about other informal nicknames used to describe boys in their current situation.
“‘Alexiones,’ and ‘the Alexionian Society’ are such mouthfuls though, and the ‘Society of the Alexiones’ is almost a meal by itself,” Tara said with a wry smile. She explained, “We don’t use those terms much in everyday conversation… mostly just for ceremonies.” She told them the Sisters also needed a simple way to differentiate them from the “real” Little Sisters who were pledging Gamma Delta and would eventually become full Sisters. With a playful twinkle in her eye, Tara continued, “So you four are our newest ‘Delta Darlings!’”
“‘Delta Darlings’…?” Nate asked hesitantly as the cutesy term seemed to almost stick in his throat. It even felt embarrassing to say it as he tentatively tried out the overly sissyish term.
Tara smiled and said with a wink, “That’s right. You’re a ‘Delta Darling’ now… Darling!” Several stifled giggles were audible at Tara’s teasing wordplay. The boys shifted uncomfortably, their faces growing even redder. It was clear that Tara and the other Sisters were genuinely delighted to see the boys put in their new, distinctly subordinate roles.
Tara went on, “There’s some interesting history to it. Back in the early days, they initially used the term ‘Little Darlings’ for boys like you. Over time, that kind of morphed into ‘Delta Darlings,’ and ‘Little Darlings’ was used less. I think the idea was to put more of a ‘Delta’ stamp on you,” she added brightly. A few more nicknames came and went over the years like ‘Delta Dolls’ and ‘Little Gammas.’ There was a time in the 70s they used ‘Petal Boys’ occasionally, but that was just a short fad. We mostly use ‘Delta Darlings’ today, but you’ll still hear ‘Darlings’ for short.”
Wearing a nervous frown, Owen began to speak with a trace of whiny protest in his voice, “But, do we really have to—?”
“Yes,” Brianna interrupted and cut him off, “Yes, you do.” Then she added, “It’s OK to ask questions, sweetheart, but you lose a point for that tone.” It was an obvious warning shot… for all of them.
The boys’ cheeks all flushed, clearly unsettled by the swift response to this very mild hint of resistance. The lesson was clear. They also collectively cringed at the girlish nickname now attached to them. It was troubling to realize there seemed to be a whole structure and plan reserved for boys in their predicament. It became obvious this was more than some random sorority lark. The recognition made them worry even more.
Tara then continued as if nothing had happened and directed their attention back to their booklets. She pointed out a timeline of key events. “We cherish our rich history,” she started, “Gamma Delta was founded in 1928 by six independent women who wanted to create a supportive space for female students at this university. You’ll need to know each founder’s full name and explain her contributions to our legacy. You can find all their portraits in the hallway, and I highly encourage you to study their biographies thoroughly.”
Turning the page in his handout, Milo noticed a chart listing all the chapter presidents since the founding.
Tara continued, “You’ll also need to memorize all the chapter presidents in order and the years they served, and of course you’ll be responsible for knowing all our current officers.” She gestured at a photo collage on the lounge wall showing the current board members, encouraging each boy to match faces to names. Their hearts began to sink as they realized just how many names and dates they’d be expected to rattle off on demand.
“The alumna section is also very important,” Elise added, flipping to a list of notable graduates and their accomplishments, “Details matter! During our Thursday study halls we’ll be doing ‘Alumna Spotlights,’ so each week, you will one choose one distinguished graduate you admire and make a short presentation describing her contributions, achievements and why you chose her.” She grinned, “You have so many to choose from!”
Madison added, “And don’t overlook the appendix. That’s where you’ll find important things like our code of conduct, tips on dressing for success and a list of our recent philanthropic projects. There’s also a helpful section on etiquette tips at chapter events such as how to greet visiting alumnae, the correct way to introduce yourself and how to write thank-you notes.”
Then, it got worse. With an almost nonchalant air, she said, “The study guides are obviously just to get you started.” She gestured to a large bookcase in the corner filled with thick, leather-bound volumes, “Over there are our annual histories… one volume for every year. Of course, you’ll need to become familiar with how it’s all organized so you can quickly find anything you need, but you should start with the basics in the handouts.”
As the Big Sisters made their expectations crystal clear, the boys’ discomfort grew. The sheer volume of information—names, dates, songs, symbols—loomed like an avalanche. Sitting there meekly in their adorable matching skirts and blouses, they realized how hopelessly screwed they were.
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Sounds like the little 'Delta Darlings' are in for a tough time. I think there is going to be a lot of punishment meted out. Interesting to see what form this will take.
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The Evening's Close
Later, when their first study hall finally ended, the boys packed up their things and made sure to take their new Gamma Delta study guides with them. The newly minted Delta Darlings dejectedly went back to change into their regular clothes. They were each acutely aware of the soft swish of their skirts and the gentle cling of lace against their skin. Nate gave a small sigh of relief as he tugged on his familiar jeans and hoodie. The coarse denim and loose cotton felt reassuringly ordinary, but the ritual of changing back into his regular clothes suddenly felt far from routine. The delicate lace beneath his clothes reminded him that he was still in uncharted territory, and it not for the first time of the evening he found himself having an unwelcome physical reaction to his frilly panties. Although they didn’t discuss it, he was not the only one. Milo, always one to maintain a brave facade, moved with more composure. On the surface, he appeared somewhat less self-conscious as he neatly hung up his Gamma Delta study clothes.
Julian moved deliberately and seemed to linger a bit, hanging his skirt and blouse on their hangers with gentle care. His fingers traced the soft fabric almost wistfully. He blushed as he realized what he was doing. Owen changed rapidly, his face set. His motions were almost mechanical. He tried to ignore the persistent tickling of his lacy bra beneath his shirt, and his heart beat rapidly as the events of the evening crashed down on him.
As they left the Gamma Delta house, the boys walked in near silence as they became lost in their own thoughts. By going through tonight’s “initiations,” they had each been awarded 10 points. They should have had 40 points, but their group total stood at 39 toward the goal of 1000 after Owen’s lost point. It seemed hollow, however, as they realized all the potential ways in their future to rapidly lose ground. The boys had the distinct impression that the Sisters had taken it easy on them since it was the first night.
Still trying to make sense of what they had gone through, Owen broke the quiet with a pointed question, “Does anybody still think this is going to be over in a month?”
The silence that followed provided a clear answer.
Nate finally sighed quietly, “Don’t forget to do your journals tonight, guys.”
Their first study hall evening had left them all feeling exhausted and spent. They seemed to heave a collective sigh to be reminded of yet another task ahead. They drifted slowly apart and trudged to their own rooms, trying not to be noticed in their still made-up faces. Each boy was acutely aware of the unfamiliar feel of mascara on their lashes and the faint shimmer of gloss on their lips. The fear of being recognized or called out by the other guys in the dorm sent their hearts racing. Every distant laugh, every creak of a door, made them tense, worrying that someone would catch sight of their prettily made-up faces. Once back in their own rooms, they all soon discovered that removing their makeup was a chore in itself. Even after some wiping, they found their cheeks still tinged with stubborn color and felt all the more exposed for it. Their makeup seemed to determinedly hang on despite their efforts. Then, they all reluctantly sat down to process their emotions and begin writing in their journals about being transfomed into “Delta Darlings.”
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Lace and Grace
On Wednesday afternoon, the boys assembled in the quad. They quickly had realized they couldn’t really postpone shopping for new lingerie, since they only had the one set each. Their Big Sisters had dropped strong hints about a particular boutique in the quaint college town with knowing smiles and cryptic encouragement. The task ahead felt daunting, and they exchanged uneasy glances as they set off together. Lingerie shopping was uncharted territory, and the prospect of selecting such intimate things made their cheeks burn with embarrassment and nerves.
The disquieted Little Sisters slowly made their way to “Lace and Grace.” As they approached the cozy shop, the boutique’s window display sparkled in the afternoon sun. In the display window, delicate pastel bras hung alongside embroidered silk robes and a multitude of other dainty and feminine apparel.
Nate paused, uncertain. “Are we really doing this?” Nate muttered, his voice wavering.
Milo tried a brave smile, “Let’s just… get in and out, quick as possible.” Then Milo nudged Nate through the door first.
Every head seemed to turn at the soft tinkle of the bell above the door. Although there were only a couple of other customers, they were all surprised to see the four cringing college boys enter. The incredibly feminine space glowed with soft pinks and lavenders, and the air was thick with the scents of sachets and soft new fabrics. Velvet chairs and gilded mirrors enhanced the overall sense of feminine elegance.
Two of the store clerks, Anna and Becca, recognized the boys immediately from the moment they stepped in. They smiled mischievously at each other. They knew precisely why the boys were there. Anna, feigning ignorance, approached first and said, “Welcome to Lace & Grace.” She then asked with playful curiosity, “Are we shopping for our girlfriends today?”
“Or maybe your sisters?” Becca chimed in, her voice teasingly sweet. “We have some beautiful sets for gifts, if you’re not sure what to pick.”
None of the boys knew how to say the words, so they just stood there in cringy silence.
Becca let the pained silence linger for a moment. Then, she exchanged a glance with Anna before adopting a mock-serious tone. “So, if it’s not for sisters or girlfriends, what brings you in today?” she asked, eyes twinkling.
Milo fidgeted, shifting his weight from foot to foot, and Julian stared at his shoes. The boys exchanged desperate glances, each silently willing the others to speak up first. Finally, Owen cleared his throat and stammered, “Actually… uh… it’s not for anyone else. We’re… shopping for ourselves.”
Anna’s brows shot up in mock surprise, and Becca’s lips curled into a knowing grin. “Oh really?” Anna replied, feigning innocence. “That’s so fun! You want some pretty things for yourselves?” Grinning, she pointed to a delicate pair of lavender panties on the nearest rack. She asked innocently, “What did you have in mind? Perhaps something soft and lacy like these here? Or maybe something a bit more sheer?” Her eyes sparkled as Owen’s cheeks turned a deeper shade of red.
Nate attempted to explain, his face nearly as pink as the pastel bras on display. “Well, umm… we already have some… but we need more.” He added weakly, “It’s, uh, a sorority thing.” His feeble words hung awkwardly in the air. His explanation didn’t seem to explain much at all.
“A sorority thing?” Becca asked teasingly, “I didn’t know boys could join sororities, but more power to you!” Anna couldn’t hold back a laugh, and Becca giggled with her, their amusement genuine but not unkind. With a wink, Becca said softly, “Relax boys, we’re Gamma Deltas—Madison told us you might stop by.”
Anna added somewhat conspiratorially, “Just so you know, we have a surprisingly large clientele of trans women… and also quite a few adventurous and open-minded men… more than you might expect. So we are well ‘equipped’ in all kinds of frilly things that might match your anatomy!” She chuckled a bit more as she finished.
The boys didn’t know whether to feel relieved or even more uneasy.
A moment later, Anna said, “Well let’s get started then! This is going to be such fun!” Her tone was warm, but her eyes danced with playful mischief.
Then, Anna and Becca led them over to some of the racks of frilly, lacy lingerie sets. “Alright, boys, drop your jackets,” Anna instructed, “we need to check your sizes—bust, waist, hips, and all that.”
The boys reluctantly placed their jackets on one of the velvet chairs, and Anna and Becca set to work collecting their measurements. Anna started with Owen, wrapping the measuring tape around his torso. She smiled, “Let’s get your bust first—stand up nice and tall, sweetie.”
Meanwhile Becca sized up Julian and remarked on his graceful build. The two clerks quickly got what they needed and began holding up delicate bra and panty sets on the cringing boys. They began a running commentary on which ones suited them best. The two sisters then began interrogating the boys on their preferences for colors, fabrics and styles. They insistently coaxed the Little Sisters to be more specific about the lingerie they wanted.
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Delightful. Now the Delta Darlings are finally shopping for their frilly lingerie I hope the girls tempt them into buying the girliest and frilliest sets available in lovely pastel colours. Look forward to next episode.
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Appreciate the nice comments BabyJay! I have a lot of raw material for this story. Keep trying to organize it to make it more manageable and entertaining ;) More soon...
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So glad your writing. I have missed the little sisters. Your writing is so descriptive it's almost like i am their watching the story unfold. Keep up the good work. Thank you.