Chapter 267.

The day proceeded satisfactorily.  All the women were so attentive to him, asking him about his work, his friends, and life at Pitt’s Wood generally, all promising to book a session as soon as they had time.  After lunch, which Tim helped to serve, Cassandra seated herself in an armchair with a glass of wine on a table by her side, and beckoned to Tim.  She patted her lap.
“Sit with me for a bit, Timothy…”
“I’m too ‘eavy, Mrs Egerton…”
“Not  at all.  Come on, sit down.”
He lowered himself gingerly onto her lap.
“See?  Comfy?  You’re as light as a feather.”
She was a biggish woman, and her legs did seem very robust…
“Now, tell me all about your boot-cleaning exploits, and your friend Bobby.  Is it true he too looks good in a dress?”
“Oh, er, yes, er miss…  ‘E looks fantastic.  There’s a pitcher on my phone…”
“It’s in the bedroom.  I’ll bring it,” said Doreen, jumping up.
“And you both wear little pageboy uniforms, I hear…”
“Er, yeah…”
“With little tight latex shorts…”
“…yeah…”
“Actually I’m teasing.  Serena showed me the photos.  Darling, you both look so cute.  The girls at the Centre must be falling over themselves…”
Tim gave a nervous laugh.  Doreen returned with the phone.  Tim scrolled to a picture of Tim in his dress.  He showed it to Cassandra.  The effect was quite startling.  He felt her stiffen.
“Oh my god!”  She stared at Tim’s phone.  “Is that actually…a boy?”
“Yeah…  That’s Bobby aw right…”
“Doreen.  Show the others.  We need him…”  She stopped suddenly.  “I mean, we should really invite both of you, sometime…  You’re such good friends, after all…  We could find lots of new dresses for you…”
“’E’d like that,” laughed Tim.  “’E loves ’is girlie fings…”
“Yes…” she said, apparently more to herself than to the company.  “Yes…  I should speak to Violet about it…”
“Miss Poole?” said Tim, innocently.
“Oh…”
“Miss Poole one of mum’s oldest friends,” put in Serena, by way of explanation.  “How do you think I got that session, and was able to book this weekend so quickly?”
“Oh, yeah, I see…”
Cassandra’s free hand rested itself on Tim’s thigh, rather too high up for comfort.  In response he instinctively placed his hands on his skirt, just as if he was a demure girl.  She appeared not to notice.
“Now Timothy, my friends and I are all going away for a little hol this evening, so unfortunately we won’t be here tomorrow.  But Serena and her friends will take good care of you.  Do you promise to be a good boy – or a good girl – and do everything they ask?”  Tim nodded.  “I know you will.  Because I would like to renew our acquaintance as soon as possible.  We all do.  Don’t be intimidated, will you?  I know it must feel odd being surrounded by women without your best friend at your side…”
“It’s okay, miss…really…”
“You’ll have a friend tomorrow, I’m hoping,” said Serena.  “Nicola’s coming, and she said she’ll bring Terry.”
“Oh, good!  Excellent!” cried Cassandra.  “He can show Timothy the ropes…”
“Yes, mum,” said Serena, with a slight frown.  “He can show him how to repel unwanted attention…”
Tim felt slightly puzzled.  But he was feeling slightly outnumbered, and the prospect of a male friend appealed.
“Can you curtsey?” asked Cassandra, suddenly.
Tim smiled uneasily.  “Never really tried…”
“Lucille, you’re the deportment expert.  Would you like to…?”
“Delighted, Cassandra.  Here, young man.  Stand up over by the bookcase.  That’s it.  Now…  First of all take the hem of your dress each side between finger and thumb, as delicately as you can.   Yes…just hold it lightly, no stress.  Smile and keep smiling.  Not that much, silly!  Yes, that’s better.  Now, I want you to bend your knees…slowly…just a little…while all the time holding you skirt at the same distance from the ground.  It’s not easy.  Your body will descend slightly, but your hands keep their level, so the skirt rises slightly relative to you.  Try it…”

The entire afternoon, until the early supper which predicated the ladies’ departure, was occupied with Tim’s education in things female.  There was curtseying, deportment – with a book on his head! – correct movement in walking, greeting, picking things up from the floor, correct speech – polite, measured, light in tone and substance, accompanied by “appropriate” facial expressions - and even some basic advice on dress and makeup, though Cassandra mentioned these topics were so important that other days would be set aside for their pursuit.  Tim was quite exhausted at the end of it, and puzzled as to the point of the whole exercise.  It was as if he was being trained for something!  But what that could be, he had no idea.

After Cassandra and her friends had left for their vacation, and he was alone with Serena, he plucked up the courage to ask.
“Serena…  Why did I ‘ave to do all that stuff for yer mum?
“Oh, I’ll explain everything tomorrow.  Now come and sit with me.  Let’s have a drink.  I want you to tell me all about what you and Bobby get up to in the boot parlour.  It’s been a while now.  Are you enjoying it?”
“Oh…  Well, yeah, I guess…  See, I ain’t never ‘ad my own place before…  I don’t wanna go ‘ome again…  It feels like we’ve suddenly grown up…”
“And you have such cool outfits…”
“Yeah…”
“But dresses aren’t so bad, are they?”
“No…  It feels so light…  An’ all the little fings girls can wear, earrings and bangles…and the makeup an’ stuff…  An’ perfume…”
“You like that?”
Serena seemed genuinely interested.  She was much nicer that he had thought originally.  She had her arm round his shoulders and was smiling at him.  He felt he could tell her anything, more than anyone else he knew.  He began to open up.
“Yeah…guess so.  Before I fought it was sissy.  But then I saw Bobby in ‘is dress…  He looks so pretty!  An’ now I can see why ‘e likes it.  It makes yer feel so sor’ of…perfec…  I was surprised ‘ow amazin’ I look…like I almost wanna go out and show it off to everyone…”
“That’s so cool!  Well, Tim, tomorrow you’ll have a new outfit.  I can’t wait to see you in it.  No, no…  It’s a secret.  But I know you’re going to love it…”

Serena helped him get ready for bed.  She had a pretty pale pink nightie for him.  He was a little embarrassed because his coc-k, rebelling against its confinement, had been leaking prec-um all the afternoon, making his pretty satin panties all slimy.  So to protect his nightie and the sheets, Serena put a condom over the whole lot.
As he lay in bed that night, in the fussy room, on perfumed sheets, wearing his frilly nightie, he wondered what Serena’s friends would be like.  He felt that they couldn’t be as demanding as her mother’s crowd.  And he was looking forward to meeting this Terry…

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!”

Oh dear!! Caught in the act. I dread to think what punishment is in store for them. something very unpleasant and humiliating I imagine. Looking forward to continuation.

 ( " 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!

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.