Chapter 322.

The girls, accompanied by half the class, walked Tim home from Margaret Sanger that afternoon.  That evening, when Shirley got home, she was treated to a blow-by-blow account of the show-and-share, which had Tim blushing again.
“Well you’re a good boy for being such a sport.  I’m not surprised everyone was impressed.”
“’Specially Miss Taylor,” quipped Clara.
“Oh, I can imagine…  Anyway, I have some news too.  Tim, I’m sorry to say that you’ll be going back to ESDS in the morning.” 
“No….” cried the girls, in chorus, throwing their arms around him.
“Already?  Why so soon?” asked Maggie.
“Because he’s mastered the basics now, and my role is finished.  Besides, he has a wedding to attend on Saturday, and he needs to be prepared.”
“Prepared?”
“Yes, dear.  He needs to be pampered for a few days, have proper skin care, get his hair cut, all that stuff, so he looks nice.  He is the sole pageboy, after all.  He’s a very important person. Oh, and Nicola said you have a parcel from…Fantastex, is it…?”
Tim punched the air.  “Yess…  My special pageboy pants!”
“P-pageboy pants…?”  Clara queried, looking at him askance.
“Oh, er, yeah…  See, like, when you’re a pageboy, you, er, have to have a special outfit, and…”
“Just so long as we gets some piccies, Tim…” smiled Maggie.
“Oh, yeah…sure…course…  Wow, I can’t wait…”

Nicola collected him the following day.  He said his goodbyes, promised to visit – even, under pressure from Maggie, to undertake a return visit to Margaret Sanger – and departed.  They were back at ESDS by ten.  He was eager to see his pageboy outfit, and kept pestering Nicole until she fetched it for him to open.  She watched as he knelt down and opened the box and took his outfit out piece by piece.  First, his little pageboy cap, red vinyl.
“Cool!”
Then his crisp white short, snow-white socks, and red bow-tie.  He looked up at her.
“Miss Nicola?  I need to put these in my drawer as soon as possible.  They mustn’t get creased before Saturday.”
“Of course, Mitzy…”
He looked up.  “I won’t be Mitzy when I’m a pageboy.  I’ll be Tim.  Pageboy Tim.”  He gasped.  He had found his pageboy shorts.  He carefully unwrapped the tissue, unfolded them, and held them up reverentially by the waistband, eyes sparkling.  “Look at these, miss!”
She was looking.  Looking and trying to keep a straight face.  Purple latex pants with ink leg frills!  She bit her lip, and choked back her laughter.
“Oh, how smart you’re going to look!”
“And they have a matching belt…  See?  These are next year’s colours, you know, miss.  But I’ve got them now!  And look, here are my shoes…  Red, see, so they match my cap and my tie.  Brilliant!"
“And what’s that little package?”  She reached in and picked it up.  “Oh!  A little pair of red latex gloves.  How sweet.  Amazing!  Now I have something to attend to.  Why don’t you repack everything into the box, then we’ll go to your room and put it all away neatly, and I’ll come and discuss the programme for the next few days.  Yes?”
“Sure, miss.  I’m so happy now…”

She had to get out of there.  She closed the door and vented her amusement with a snort she hoped he didn’t hear.  In the corridor she ran into Cassandra.
“What’s the big joke?”
“Oh my god, Cassie.  That Tim.  You should see his outfit for the wedding.  He’s so excited.  I nearly burst out laughing.  I mean, little tiny pink and purple latex shorts!  And a bowtie!  What does he think he’s doing?  He’ll be a laughing-stock!”
Cassandra nodded slowly.  “First of all, Nicola, he won’t be a laughing-stock.  Everyone’s been thoroughly briefed.  He’ll be flattered and praised from all sides.”
“Really?  How so?”
“Miss Poole has put the word around.  This isn’t going to be his last wedding – or his last event.  She has big plans for her little pageboy – weddings, hen parties, dinners…  A cute little diversion for any occasion, our own little amusing wunderkind.”
“But how does he not realise…?”
“It’s sweet, isn’t it?  The thing about Tim is he’s really desperate to let everyone – but particularly the girls – know he’s a boy.”
“Well they won’t have any doubt about that when they see him in those little tiny latex pants!”
“What I mean is, he wants to show off and be admired.  It’s innocent vanity.  I think it’s his antidote to his maid training.  He does his best for one reason – to get our approval, and ultimately the approval and attention of his mistresses.  But at the same time it confuses him, being dressed as a girl.  It doesn’t feel natural for him.  But he desires female approval and proximity above all else, and it gets him that.”
“Is that all he wants?  Doesn’t he want a girlfriend?”
“The girls found out a lot during his interviews.  He has no duplicity.  He blurts out what he feels, what he likes.  He does have a sort of girlfriend at Pitt’s Wood.  But it seems she comes second to his friend Bobby, and second to his work.  However he might complain sometimes, in general he loves being a boot boy.  First of all he loves the feeling of latex pants.  It makes him horny, and when he got his little latex gloves on as well he sometimes finds it difficult to keep his hands off himself.  Second, he loves it because the uniform gets him loads of female attention.  It’s the same with the pageboy outfit.  But he’s essentially a very shy boy, so he rarely really gets further than flirting, or being flirted with.  When we pressed him he admitted he actually prefers to wear his pants and gloves and masturbate.”
“Gosh, really?”  She laughed.  “Well, well, how sweet.  I don’t know what to say – except that ESDS seems the perfect place for a boy with his exhibitionistic and fetishistic tendencies.  Don’t you think?”
“Absolutely, Nicola.  And I want him to be able to show off to his heart’s content.  So until the wedding we won’t worry about his maid training.  I want Carly to make him look as good as she can – facemasks, get his skin perfect, do his eyebrows, no makeup, mind, except for the tiniest touch of mascara.  Oh, and no device for the time being.  Saturday is his boy time – his last boy time for a week or two at least, I imagine.  Lucille wanted to see him in his finery before he goes, so on Friday we’ll have a dress rehearsal and she can interview him to make sure he’s presentable and he’s happy with everything.  Serena’s been invited to the wedding so she’ll drive him to the church Saturday morning, and bring him back in the evening. The following week he can go back into training and we’ll focus on his makeup, so he makes a good impression when we send him to Connie Brookshaw’s.”
“How many uniforms is he going to take to Connie's?”
“A couple, plus she’s ordered a special – sort of pink vinyl and crinoline creation – which should be in Wednesday or Thursday.”
“Isn’t she the one who likes…you know…?”
“Harnesses and masks?  Yes, that’s right.  But she knows he’s a novice.  She won’t be unkind.”
“In at the deep end…”
“Nonsense, dear.  He has to learn his trade.  And I predict he’s going to be one of our most popular maids.”

SATURDAY MORNING – GETTING STARTED

       As soon as Claire Dixon turned into the street for her walk, Caitlin texted her cousin Stephanie: “Get over here! It’s game time!” Almost an hour ago, she had rousted her still-drowsy little brothers and prodded them to start getting cleaned up and then get down to the basement. Both boys had groaned softly, rubbing their eyes and burying their faces deeper into their pillows in a futile attempt to ward off the morning that awaited them. Jack, still tangled in his bedsheets, had muttered something unintelligible about needing five more minutes. Justin had thrown his arm over his face, trying to block out the light streaming in from the hallway.

       Despite their initial protests, the boys had slowly shuffled out of bed, finally giving in to Caitlin’s gentle but persistent encouragement. Their teenage antics had just made her giggle. She found their tousled hair and dramatic, adolescent sighs hysterical but still somewhat endearing. After some playful coaxing, Caitlin got her way, and they had begun to come alive. With a shared look of nervous resignation, they felt the Mother-Daughter Easter Brunch rushing toward them.

       Now, Caitlin could hardly contain her excitement. She headed down to the basement herself to make sure they were doing as she had instructed to prepare for their day as her ‘little sisters.’ Meanwhile, Stephanie had briskly walked the two blocks to come over and join them, a pink tote bag swinging merrily from her shoulder. As Caitlin opened the basement door to let Stephanie in, she called out with mock sternness to her brothers, “Time for your makeovers, boys!” Her voice carried a teasing lilt that made Jack and Justin exchange shy, nervous smiles. Their cheeks began to flush with anticipation, a mix of nerves and excitement swirling inside them. They were fully awake now.

       As things kicked into motion, Stephanie’s voice rang out with playful authority, “First, let’s see those nails!”

       Dressed in their gym shorts and tee shirts again, the boys blushed but held out their hands. Once they had gotten to the basement, they had carefully painted each other’s fingernails with the cotton-candy pink polish Caitlin had given them, struggling to keep their hands steady and avoid smudges. It was a virtual repeat of their nail-painting escapade at Christmas, and this task had been the subject of the giggling and playful arguing their mother had overheard a little while earlier. The scent of nail polish lingered in the basement air now as a reminder that their return trip to girlhood had truly begun. As instructed, they obediently extended their fingertips to reveal darling, shimmering pink nails. Both boys’ cheeks flushed red as the girls leaned in for a closer inspection.

       Nervous but committed now, Jack wiggled his freshly painted fingers playfully, “Not bad, huh?” He nodded toward his twin, “I mean, his look better of course because I did them!”

       Justin rolled his eyes and replied gamely, “Oh please sweetheart, you know I’m the true artist here!” He held up his hand, “Look, you totally smudged my thumb!”

       There was indeed a little smudge there, but overall, the boys actually had done a nice job on their manicures. Their playful banter eased some of the tension.

       Caitlin rolled up her sleeves with delight flickering in her eyes. She gently took Jack’s hand, tilting it to the light, and examined the glossy pink finish. Stephanie took a seat next to Justin, and he compliantly turned his hand palm down with fingers splayed wide when she gestured. The twins silently hoped their efforts would pass muster. Caitlin and Stephanie murmured in amusement. The boys’ embarrassment was palpable. 

       â€œLovely, little sisters… not bad,” Caitlin teased. “Guess there’s no turning back now!”

       Stephanie used her own fingernail to daintily test the polish on the very edge of Justin’s pinky fingernail, and she was pleased to see it was no longer tacky. “Great!” she nodded approvingly, “looks like they are dry… and we can clean that little smudge up in no time.”

       â€œI see you are becoming manicure experts… second time’s the charm I guess” Caitlin observed drolly. Then she added expectantly, “It’s time to get girly!”

       The brothers looked at each other sheepishly as Stephanie agreed, “Let’s get to work then!” She reached into her tote bag and cheerfully handed each twin a small package wrapped in tissue paper and tied with a bow. “Happy Easter, darlings!” she giggled.

       Jack and Justin looked at other with pained looks, as it was already obvious what these were. They opened the tissue paper tentatively.

       â€œC’mon, do we really have to?” Justin asked with chagrin.

       â€œYeah, can’t we just wear our shorts like yesterday? Please?” Jack added hopefully.

       Caitlin waved off their protests somewhat impatiently, “Oh, don’t be chicken! It will keep you in the right frame of mind, and as I recall you both survived Christmas just fine!” She insisted, “Now scoot and change! The clock’s ticking!” Her teasing left the twins no room to argue. With pink faces, they shuffled off to the bathroom with their dainty parcels in hand.

       A couple of minutes later, the boys bashfully tiptoed from the bathroom as if they were walking on eggshells. Gone were their gym shorts and tee shirts; now they both wore utterly adorable matching bralette and bloomer short sets! The tastefully modest underthings were satiny white, edged with sugary pink accents and nearly overflowing with bouncy ruffles. Their charming bralettes featured slender spaghetti straps that were trimmed in soft frills and tiny bowknots in front. The matching bloomer-style panties were made of the same soft white satin with layers of frilly ruffles and adorable pink trim. Generous lacy fringes made the ultra-girly garments all the more precious.

       Caitlin's laughter practically bubbled out the moment she spotted them. “Oh, would you just look at you two!” she squealed, “you’re so cute I can hardly stand it!”

       Stephanie added with a wide grin, “You look like little princesses!” She continued cheerfully, “maybe you should just go like that!”

       Jack and Justin shifted awkwardly, cheeks deepening in color as they twisted their hands awkwardly. Caitlin teased them gently, “Oh, don’t be so shy!” She mischievously reminded them, “I used to help Mom change your diapers all the time when you were babies… I’ve already seen it all!” She then asked them slyly, “besides, did you know those are actually called ‘boy shorts?’”

       â€œBoy shorts?” Jack repeated in disbelief. He wasn’t sure if Caitlin was pulling his leg or not.

       Stephanie explained that they really were called “boy shorts.” She said, “They’re just like your boxer briefs, only, well… a smidge daintier.” She chuckled as she said the last part.

       Justin groaned and Jack sighed. Nothing about these… panties… was remotely boyish. The twins were already feeling less boisterous and much more… girly. The tickle of lace along their waists and shoulders sent shivers up their spines, leaving them squirming and a little breathless. The lacy frills tickled their skin in a way that was vaguely familiar but still unsettling. They felt more subdued. Anticipation mixed with nervousness as they braced themselves for what came next.

       Before they could really catch their breath, the girls rapidly bustled around them again.

       â€œPetticoat time!” Stephanie announced.

       Caitlin opened Justin’s frothy white petticoat for him as the layers of tulle rustled noisily. A few feet away, Stephanie held out Jack’s, pulling it open so he could step through the elastic waistband. As the boys slipped their feet inside and the girls guided the petticoats up their legs and over their ruffled bloomers, the process felt familiar but much more electric. In contrast to the gym shorts they had on yesterday, their elaborately frilled “boy shorts” amplified the sensations as each brush of ruffles and tulle against their skin created a little tingle of energy. As the frothy petticoats were tugged into place around their slender waists, the wispy layers rustled with every slight movement.

       â€œJust like little angels,” Stephanie observed gently as they stood barefooted in their precious petticoats and charming ruffled bralettes. There was significantly less teasing in her voice now, and the twins couldn’t help but blush even more.

Thank you BabyJay. As one of this site's more consistent supporters/cheerleaders, it always makes me smile to see a post from you.

Hugs and kisses! The rest of the story is already completely drafted, but I'm still polishing each part. I plan to have it all published in time for Easter :)

Thank you for the explanation!  Please don’t worry about this. I understand things happen and I actually really like your take on this story. You have my blessing please continue and I will happily read as you update!

This is a great story! I know because I wrote it 6 years ago and am still actively working on iron several different sites. I’m all for imitation or writing your own interpretation but you stole my work word for word    https://www.dailydiapers.com/board/index.php?/topic/74864-the-teacher/&