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91
Active Sissy Stories
/ Re: The Mother-Daughter Easter Brunch
« Last post by BabyJay on March 29, 2026, 04:16:53 AM »
Delightful. I think the 'Princesses' are enjoying this more than they are letting on. Could this now be the start of a regular Dress up programme, i.e. Birthdays, Anniversaries, Thanksgiving, etc.? They could then each acc-umulate a lovely wardrobe of Pretty dresses, Frilly Knickers, Petticoats and shoes. Mmmm just a thought.
92
Active Sissy Stories
/ Re: The Mother-Daughter Easter Brunch
« Last post by sissyboy1212 on March 28, 2026, 10:26:02 PM »
SATURDAY MORNING – FINISHING TOUCHES

       Jack and Justin sat more quietly, almost docilely, as Stephanie and Caitlin set about transforming their blonde hair into passably girlish styles. Armed with combs, brushes and a curling iron, the older girls coaxed the twins’ natural curly hair into soft, gentle tresses that framed their faces cutely. Jack and Justin got glimpses of the work in progress in the mirror, and soon the sweet scent of hairspray filled the air.

       Strategically placed bobby pins and a dab of gel gave their hair polished finishes. The twins blushed as pastel bows fringed with lace—pink for Justin, yellow for Jack—were pinned into place for the crowning touch, making them feel even more girlish. Jack’s heart sped up a bit as Caitlin delicately adjusted his pretty bow. Justin silently watched his sister work on Jack even as he felt Stephanie’s gentle touch securing his own darling pink bow. He was fascinated as he stole a look in the mirror to see how delicate it looked perched in his hair.

       Knowing that they only had a little time left before Claire returned from her walk, the older girls worked with efficiency to do the boys’ makeup. With some amused looks and now almost whispered instructions, Caitlin and Stephanie were nearly done: “Close your eyes! Tilt your chin up!” The makeup was light and sweet—a gentle dusting of pink blush to make their cheeks glow, a touch of shimmery gloss for lips, and just enough mascara to make their eyes sparkle. The tickle of brushes on their cheeks and the slick feel of the lip gloss sent fresh tingles down their spines. The barest touches of mascara made their eyes adorably dewy. As the girls worked, they kept one eye on the time.

       Finished with the brothers’ makeup, the girls used cotton swabs, nail polish remover and a few more touches of polish to gently clean up the boys’ nails. Then, they stroked on a quick-drying topcoat for added shine. As the girls touched up their glossy pink nails, the boys were nearly mesmerized by the way their nail polish gleamed and flashed under the light. Noticing the boys’ more gentle demeanors, Stephanie caught Caitlin’s eye and shared a soft, knowing smile. They both thought it cute how Jack and Justin seemed to be lost in such quiet fascination. Both older girls found it utterly charming.

       Caitlin leaned a little closer to them and whispered gently, “You know… it’s perfectly fine to enjoy feeling pretty.”

       Stephanie nodded in quiet agreement, her face warm and encouraging. There was little joking in her tone now as she spoke softly, "Your big sister's right. It's pretty obvious that you two don't 'hate' this!" She said the last part with the gentlest of teases and a warm, loving smile. The boys reddened a bit more, but they almost seemed to be basking in the sweet, gentle attention now.

       The basement was very quiet and still for a few seconds.

       All too soon, however, the tender moment passed. They were still on the clock after all. “OK, up you go!” Stephanie urged as she had them stand with a wave of her hand. Jack and Justin stood up tentatively, skirts swishing, as the girls checked over their outfits. Standing side by side in their Easter best, they had butterflies in their tummies.  From their frilly boy shorts and bralettes to their preciously curled hair, every aspect of their outfits made them feel dainty and precious.

       â€œHold still,” Caitlin said as she straightened Justin’s hair ribbon. Meanwhile, Stephanie reached down and tugged delicately on one of Jack’s frilly white socks. The girls’ faces broke into affectionate smiles as they fussed over the last details. When the girls finally stepped back, the boys stood blinking and a little breathless at their relentless and fast-paced makeovers.

       â€œPerfect,” Caitlin declared. “You both look absolutely darling!” She continued almost giddily, “I never knew I had such cute little sisters!”

       â€œAunt Claire won’t believe her eyes!” Stephanie agreed excitedly. Clearly very satisfied, she added, “you two are all sugar and spice now… just like the nursery rhyme!”

       Jack and Justin cringed adorably as the girls gushed over their sweet looks. The boys’ cheeks were pink with embarrassment. Every playful tease seemed to affect them a bit more. Being fussed over like this and dolled up so thoroughly made them very self-conscious. It seemed increasingly evident, however, that they were both secretly at least a little bit pleased at the girls’ reactions.

       Still, as the reality of their transformation settled in, Jack and Justin were somewhat overwhelmed by just how sissyish they were dressed. Their pastel dresses, layered with billowing frills, made their previous Christmas outfits seem plain in comparison.

       Justin’s cheeks flushed as he admired Jack’s sunny yellow dress, his oversized satin bow and gleaming Mary Janes. "Wow, Jack… I can’t believe how we’re…” he murmured softly as his voice trailed off. 

       Jack let out a nervous laugh. “Yeah, I mean, we look like we belong in a dollhouse… Christmas was wild, but this is… just wow,” he stammered, unable to find more words. Their bashfulness was tinged with a hint of pleasure; the feeling of being so prettily dressed was clearly having an impact.

       Justin recovered a bit and shrugged helplessly, “I think it’s way too late to back out now.” Turning to Caitlin, he added nervously, “You really went all out on us.” Their hearts beat a little faster now as they thought about the spectacle they were bound to create at brunch, but they both managed shaky smiles. They seemed resigned to following through and tried to find humor in their predicament.

       â€œWell, at least I don’t have to wear pink!” Jack offered softly, finding his voice again and trying to joke. Justin cracked a reluctant grin.

       â€œI happen to look great in pink!” Justin teased with a little more energy, his nerves melting slowly into a hint of confidence.

       Caitlin smiled at her adorable brothers and said, “Don’t worry! Everyone will love you!” Then, she added insistently, “we still have a little time left. Let’s practice those curtsies one last time. Make them pretty!”

       Jack and Justin gulped in unison as their cheeks warmed again. Nothing was left to do now but go all in. They gamely grabbed their skirts and daintily dipped into a few curtsies. With each one, their rustling petticoats and swishy frills made the boys acutely aware of their utterly girlish outfits. Still, the twins managed shy smiles. Their embarrassment mingled with a sweet pluckiness as their natural exuberance flashed a little.

       As the girls admired their handiwork with satisfaction, they heard the door open in the kitchen upstairs. They’d finished just in time… Claire was home from her walk!

       Suddenly, Stephanie whispered urgently, “Wait! There’s one last thing!” She hastily rummaged through her pink tote bag and produced a small glass perfume bottle. “I almost forgot!” she admitted.

       Before the boys could react, she sprayed the air around their necks a few times. The delicate perfume quickly enveloped their noses in sweetness. The dainty fragrance was barely there. It was like a whisper of femininity mixed with subtle hints of floral blossoms and fresh body powder. The scent was subtle and sweet, perfectly suited for shy young teens, and it added the finishing touch to their transformations.

       â€œNow you’ll smell as sweet as you look!” Stephanie beamed.

       Jack wrinkled his nose adorably, exchanging a look with Justin as the girlishly dainty fragrance engulfed them. He sighed slightly, “we’re going to smell like this all day, aren’t we?”

       In response, Justin tried another weak joke, “I guess they’ll smell us before they see us now.” He shuffled his feet adorably, not quite sure whether to laugh or groan. 

       Caitlin laughed softly, “OK girls, let’s see those pretty smiles!” Gesturing to the stairs, she added excitedly, “it’s showtime!”
93
Active Sissy Stories
/ Re: The Mother-Daughter Easter Brunch
« Last post by sissyboy1212 on March 28, 2026, 10:11:30 PM »
Oh thank you babycakes. Your comment is exactly what I hope my stories to be. Sometimes I get it right, and many times I don't. But I agree that the best stories are those that let us really get inside the characters' emotions and sensations.

And for BabyJay thank you for your post as well. I agree, I think they are starting to enjoy this a bit... even though it's hard for them to admit it! :)

Here's the next part :)
94
Active Sissy Stories
/ Re: The Mother-Daughter Easter Brunch
« Last post by babycakes on March 28, 2026, 03:49:36 PM »
Once again an excellent passage with perfectly detailed clothing descriptions enhanced by noting the comprehensive emotional and tactile effects on the boys of such feminine dainties and delicates.  Really, an author can go to great lengths with clothing details and yet still miss the mark by omitting or limiting discussion of the clothing's effect on the wearer.  You, as usual, hit the nail on the head. Can't wait for the brunch.
95
Active Sissy Stories
/ Re: The Mother-Daughter Easter Brunch
« Last post by sissyboy1212 on March 28, 2026, 08:33:13 AM »
SATURDAY MORNING – ALL SUGAR AND SPICE

       Next, it was finally time for their Easter dresses.

       â€œReady ladies?” Caitlin teased, grinning broadly. In response, the boys sheepishly shrugged. It was now well too late to do anything but plow forward.

       First, Stephanie took Jack’s frilly confection of a frock off a padded hanger and cheerfully helped him into it again. Once more, he held his arms up as she smoothly dropped it over his head. As his arms slipped into its girlish sleeves, the skirt fluttered down over his ruffled bralette and petticoat. Jack’s precious pastel dress was a soft, sunny yellow with delicate embroidery along the bodice. He was conscious of the added weight of the skirt over his petticoat as the tulle tickled his legs. As Stephanie gently adjusted the puffed sleeves and smoothed out the bodice, she made sure it was fluffed just so. Its fabric felt cool and light, and Jack shivered as his cousin buttoned him snugly into it, enveloping him in its frills. As Stephanie finished by tying his wide satin yellow sash into a large bow, she made sure to leave the tails long to brush gaily against his skirt. 

       Meanwhile, Caitlin put Justin into his charmingly sweet baby pink dress and adjusted his puffed sleeves meticulously. He felt tingles as it floated down over his body like a delicate pink cloud. After buttoning him in, she took pains to fluff the full, bouncy skirt, patting it so the layers would sit just right. Then, she tied the wide pink sash around his waist, the bow at the back standing out in crisp perfection. His frock’s neckline featured a frilly rounded collar edged with lace, and the skirt flared beautifully. The frilly lace collar tickled his neck as did the elaborate lace edging the puffy short sleeves. Justin grinned sheepishly despite himself, his cheeks revealing a mix of embarrassment and delight.

       The boys realized once again how much more… elaborate… these were than their Christmas frocks. Their frothy petticoats ensured the skirts flared fetchingly, and the boys knew instantly their layers of tulle and lace would rustle adorably all day. The boys found the surreal sensations of being dressed up so thoroughly almost a bit magical. Despite themselves, they felt a bit of nervous anticipation for the next steps.

       With their Easter frocks adjusted just so, the girls had them sit and pull on their delicate white ankle socks with dainty lace ruffles. In short order, the boys’ feet were snugly buckled into darling pastel Mary Janes that matched their dresses… pink for Justin and yellow for Jack. As they stood back up, their girlish shoes felt so light and dainty, making them hyper-aware of every step.

       Surveying their progress, Stephanie grinned broadly, “you two look sweet enough to eat!” She added, Aunt Claire is going to be shocked… again!”

       Caitlin circled her brothers, her eyes twinkling with delight. “Honestly, you’re both so adorable I can hardly stand it!”

       â€œWow Jack, you’re even prettier than you were at Christmas,” Justin only half-teased. He tried to play it cool, but he realized how girlish they both looked now. Despite knowing ahead of time what had been coming, it still all felt surprising now. Despite himself, he let out a fluttery giggle.

       Jack shyly swished his skirt a bit in response. He tried to reply with sarcasm, but it came out more genuinely than he intended, “Thank you dear ‘sister,’ but you know we’re twins right? You look like a little princess yourself!” He tried to laugh, but the sound was more nervous than amused. As he glanced down at his dress, he felt the reality of their transformation sinking in.

       Caitlin interrupted their banter with a chuckle, “You’re not finished yet girls, time for hair and makeup before Mom gets back!”

       There was a decent-sized mirror on the wall of the basement, and the girls sat them down on two folding chairs to finish their looks.

       â€œSit! And no wiggling!” Stephanie barked playfully.

       Stephanie and Caitlin both grinned as the two boys sat bashfully, struggling to arrange the unfamiliar layers of petticoats and skirts. Their rustling dresses billowed adorably over the edges of their chairs as the girls giggled. Stephanie stepped in to help Justin straighten his girlish frock, and Caitlin got Jack settled opposite him. The two boys exchanged shy, subdued smiles in the mirror.

96
Active Sissy Stories
/ Re: His Aunt Nicole
« Last post by Simonssister on March 26, 2026, 03:09:35 PM »
Chapter 325.

The vicar of St. Michael’s, a woman in her mid-thirties with large pale blue eyes and silvery-blonde hair in a bob, was standing in front of the altar chatting to a man in a dark suit, while two middle-aged women were arranging flowers around the church.  The women stared as Tim and Serena walked in, and one whispered something to the other, in which, in the silence of the church, the word “pageboy” was distinctly heard.  The vicar turned her head, smiled, and gave them a little inviting wave.  They walked up the aisle to where she was standing.
“Good morning!  Welcome to St. Michael’s!”  She smiled at Tim.  “Tim, I presume.  We’ve all been looking forward to meeting you.  This is Roger, the best man.  I’m Ashley.  We were just going over the order of ceremony.”  She looked at Serena.  Serena smiled.
“Nice to meet you, Ashley.  Yes, this is Tim, and I’m Serena Egerton.  Tim’s very excited about his part in proceedings.”
“I’m sure you are, Tim.  So am I, as a matter of fact.  I’ve never had a pageboy leading the procession before.  It’s a first for me as well.  And you’re a fine, handsome lad all right.  I was sort of expecting a younger boy, but…”
“I’m nearly eighteen, miss!”
“Goodness!  Well then, if you’re lucky, you might get offered a little glass or two of champagne at the reception, don’t you think?  You certainly deserve it, for volunteering to be Debbie’s page.  You’re going to steal the bridesmaids’ thunder, you realise, especially in that amazing outfit.”
Tim blushed with pleasure.
“Now, I should explain the procedure.  The guests with begin arriving around nine-twenty.  The ceremony begins at ten.  If you would like to take a seat in the very last line of pews, I will make the introduction, and when I give you the signal, you and one of the bridesmaids will open the double doors.  Debbie and her father will be waiting outside.  They will wait for you to position yourself ahead of them, the organ will start to play, and that’s your cue to walk slowly up the aisle leading them.  The bridesmaids will follow behind.  When you get here, you should stand there – see that piece of yellow paper I’ve stuck to the floor?  That’s your place.  Now, Debbie’s asked if you could be the ring bearer on this occasion.  Often it’s the best man, but you don’t mind, do you Sebastian?”
Sebastian grinned.  “Nope.  One less responsibility for me.”
“Wow!  Really?”
“Yes, Tim.  Seb, might as well hand them over now.”
Sebastian passed him a velvet bag.
“Thanks!”
“All you have to, Tim, is to walk forward when I call you.  You needn’t handle the rings at all.  Just open the bag and offer it to the bride, and then to the groom.  They’ll take them out.  Then move back to your place.  When the ceremonies over, I’ll signal you, and you’ll lead the procession out of the church for the photos.  Any questions?”
“No…  I don’t think so…”
“Nervous?”
“No!”  he said, quickly.  “Just excited.”
“Good boy.  Now, I have some final preparations to make.  Please feel free to look around the church, if you wish, Ms Egerton.”

There was still nearly an hour till the wedding, so they wandered out into the sunshine.  A few more guests had arrived, and Tim was immediately spotted and pounced on by two girls only a couple of years younger than himself.
“Are you the pageboy?  Of course you are.  We're bridesmaids.  We’ve been dying to see you!  Mum told me all about it.”
“She did…  About…?”
“You know, all about how…  you know, how lucky Debbie was to find you…and everything.  Wow, nice outfit!  Super cool!”  She grinned.  “I’m Melanie.  I’m Debbie’s niece.  This is my friend Delia.  What’s your name again?”
“Hi.  I’m Tim.”
“Yeah, Tim.  I remember.”
Melanie was looking at Tim’s shorts with a strange expression on her face.  She was seized with a sudden fit of coughing, but quickly recovered.
“They’re very smart shorts.  What are they…  What are they made of?  Vinyl…?”
“No, latex.  It’s very fashionable you know.  And these colours…”
“They’re going to be the “in” colours next year, right?”
“Yeah…matter of fact…”
“Melanie’s mum told us.  We couldn’t believe…er, you’d really managed to get such trendy stuff…”
“It weren’t easy…  I mean, I ‘ave connections in the trade, see…?”
“Ooh, really.  Could we have a selfie with you, Tim?”
“Course.  Serena?  Could you take a piccy for my friends?”
“Of course.”

The girls stayed commendably straight-faced while Serena took a photo with Melanie’s phone.  The girls checked it, giggled, and turned away.  Delia looked back and waved.
“See you later, Tim!”
Then they ran off back to a group of women in long dresses who had been watching from the lawn.
“Nice girls,” remarked Serena.  “I think that Melanie fancies you, Tim.”
“D’you reckon?”
“Are you going to wear your gloves for the ceremony?”
“No…”  He looked away.
“Okay.  Maybe later, then…”
 

97
Active Sissy Stories
/ Re: His Aunt Nicole
« Last post by Simonssister on March 26, 2026, 03:04:25 PM »
Chapter 324.

Serena was impressed.  When she opened his bedroom door at a quarter to eight Tim was up, dressed, and raring to go.
“Wow, boy, lookin’ good!  Cool duds!” she cried, with an ill-concealed smirk. 
But Tim didn’t notice.  “Yeah, I know, Miss Serena.  Fantastex are amazing, aren’t they?  They always keep their promises.”  He pointed at his shorts.  “See?  Pink and purple, next year’s trending colours.”
Serena approached and gave his new shorts the once-over.
“Cute hotpants, darling.  You’re gonna wow them at the wedding.  Pity they’re not a little shorter…”
“Oh, do you think so?”
“They’re fine, Tim.  I think everyone will be quite sufficiently impressed just as they are.”
“Oh, okay.  Cos I can ask Cynthia to alter the measurements a bit if you think…”
Serena suppressed a smile.  Let him dig his own grave.  “Well, maybe an inch or two…  Great quality, though.”
“Yes, she only uses the best latex…”
“Where’s your gloves?”
“Oh…  I don’t need them…”
“I’m bringing them anyway.  Just in case.  Where are they?”
“In the drawer.  But…”
“Okay, got them.”  Serena was in a mischievous mood.  But when wasn’t she?  “Here, put them on now.  No, no objections please.  I want to see how they look.”
He pulled them on reluctantly.
“Very smart!  Come on then, let’s go.”
“I can take them off…”
“Yes, as soon as we get to the church.  Don’t fuss.”

She drove with Tim in the passenger seat of her orange Porsche.  It was amusing to see him exercising self-discipline, gripping his knees hard with his red-gloved hands.
“Is my driving that bad?”
“Pardon, miss?”
“You’re gripping your legs for dear life.  Relax, Tim.”
“Oh…oh, yeah…”
He clasped his hands together.  He was definitely getting a little erection.  Serena revved the engine in the hope the vibration would exacerbate his condition.

She parked.  There were already quite a lot of cars in the street so they were a couple of hundred yards from the church.  Tim pulled off his gloves and tucked them into the glove compartment.  He ceased to be tense, and became animated.
“We’re early, aren’t we, miss?”
“We’re in plenty of time.  Let’s go and see what the routine is.”
They walked the few hundred yards to the church, Tim striding ahead, and turned in through the gate.  There were a few people standing by the church door.  Tim hesitated for a second, and waited for Serena to join him.  She caught up.
“Come on, Tim.  Let’s find the vicar.”
They were about to enter the church when a woman in a yellow dress accompanied by a little boy approached them.  Tim had noticed the standing on the grass staring at them as they came up the path.
“Excuse me…  Sorry to trouble you…”  She smiled at Tim.  “Are you the pageboy Debbie told me about?  I’m Imogen, her sister-in-law.”
Tim nodded.
“Only my son seems to be quite taken by your outfit.  Right, Joshua?”
Joshua nodded shyly.
Serena smiled at him.  “Do you like it, Joshua?  Would you like a pageboy uniform like that too?”
“Yes…”
“He wants one just the same, don’t you darling?”
“Yes, mummy…but with blue shorts…”
“Blue?  Oh, of course.”  She turned to Serena and shrugged.  “His favourite colour.  Everything always has to be blue at the moment.  We call him Little Boy Blue.”
“Blue…with a yellow belt…” Joshua added, thoughtfully.
“Well, no problem, young man,” laughed Serena.  She turned back to Imogen.  “Looks as though Tim might have started a trend!  Why don’t we meet up at the reception and I’ll tell you everything you need to know?”
98
Active Sissy Stories
/ Re: His Aunt Nicole
« Last post by Simonssister on March 26, 2026, 02:46:22 PM »
Chapter 323.

After a few days of pampering, saunas and massages and facemasks and healthy food, interspersed by gym sessions and five-a-side football games with the other trainees, Tim was tingling with fitness and excitement.  On Friday morning Carly took him to one of the spare bedrooms, helped him on with uniform, brushed his hair, rubbed his cheeks gently to make them look fresh and rosy, and stood him in front of his bedroom mirror.
“Well, what do you think?”
“What do you think, Miss Carly?”
“I think you look amazing.  You’d better be careful you don’t steal Deborah’s thunder!  No, seriously, that’s a great outfit.  Love those cute shorts.  They look like they fit perfectly?”
“Yeah, they feel great!  Ain’t they smart?  I can’t wait to show everyone.  I bet most of ‘em won’t ever have seen a real pageboy before!”
“Aren’t you going to put on your nice red gloves?”
“Oh…not right now…”
“Okay.  You look cool enough as you are, I guess.  Right, let’s go see Lucille.  She’s dying to see your outfit.”

Lucille was in her office.  Carly knocked, opened the door, and ushered him in. 
“Your delivery is here, Lucille.  Full dress rehearsal.  He has gloves as well, but he didn’t want to put them on right now.  Call me when you’ve finished with him.”
“Thanks Carly!  Come in Tim – I can call you Tim now.  Stand there…  Let me look at you…”
She regarded him with obvious approval.
“Well, well…  You look absolutely gorgeous!  That’s such a smart ensemble.  Simple but so eye-catching.  You’ll be the beau of the wedding.  And you’re positively glowing!”
Tim blushed a little.  “Everyone’s been so helpful…  And Cynthia did such a great job.  I can’t wait till tomorrow.”
“She really did.  Aren’t you even a teeny bit nervous?”
“Maybe a little bit.  But I’m more excited.  Do you think Deborah will like me?”
“Are you joking?  I’m sure she will.  She’ll be ecstatic.  There aren’t many brides these days lucky enough to have a real pageboy.  In fact, I wouldn’t be surprised if this isn’t the last wedding you’ll be attending.”
“Really?”
“It’s a big do.  It would be remarkable if no-one else spotted your talent.”
“Oh…  I hadn’t even thought of that…”
“Come and stand over here so I can get a piccy.  That’s right, there.  Smile…  Great.  Now come here and let me have a closer look at you.”  She felt his shirt and ruffled the frills on his shorts.  “You should have put on your gloves too.  Well, make sure you wear them tomorrow.”
“Oh…  Well, I’ll probably take them...just in case…”
“You should wear them.  They complete the outfit.”
He blushed slightly. 
“Oh well, no problem, I suppose.  I’ll tell Serena to bring them anyway, in case you change your mind.  Whether you wear them or not, I’m certain you’re going to turn heads tomorrow.  It definitely won’t be your last pageboy assignment.  Actually I’ve asked Cynthia to send a couple more outfits like this, but with slight style and colour variations.  I’d like to put you in the brochure alongside your maid persona.  So I’ll need you to do some modelling next week after we get our Fantastex delivery – probably Thursday.  I’ll pencil it in.”
“Oh…”
“We’re just getting the Christmas issue ready.  I’m considering whether to give you two pages, one for your maid role and one for the pageboy.  You could wear two different outfits for each.  We display the boys alphabetically, so you’d be near the middle.  It would be nice if you could be the centrefold – then we could have two piccies on one page and another two opposite, and you’d need to turn the brochure through ninety degrees – just like those centrefolds in girlie magazines, - which I’m sure you’re familiar with - which you can use as posters.”
There was a knock at the door.
“Come in!”
It was Cassandra.
“I had to come to have a peek at out pageboy.  Well!  Tim, you look fabulous!”
“I’ve been telling him…”
“Did you tell him about the brochure?”
“I just did.”
“What do you think of that, Tim?  A nice big spread all to yourself.”
“Thank you, Miss Cassandra.  Would I be the only one to have a pageboy outfit?”
“The only one.  The only trainee to have an alternative identity.  You are multi-talented, after all.  What do you think?”
“Wow, it would be really great.  Actually I think I like my pageboy outfit the best…”
“Yes, I sort of thought you did.  And you like showing it off, right?  It’s fine, don’t blush.  I’m happy you’re so proud of yourself.  You have every right to be.  So just enjoy the photo shoot.  We’ll do it next week.  You can show off to your heart’s content.  We’ll make an album for you, then choose the best snaps for the brochure, okay?”
Tim nodded enthusiastically.
“Good boy.  Now off you go and get changed.  And get a good night’s sleep tonight, won’t you?  Carly will help you dress, and Serena will collect you at nine.”
“I will, miss.  Thank you miss!”

After he had left, Cassandra and Louise had a good giggle.
“He’s going to be a sensation, Cassie.  Should spice up the wedding nicely.”
“He’s so damn cute he’s irresistible.  I hope he never loses that delightful innocence.  He’s a changed boy since he came here.  I heard from Violet he could be quite surly at times when he started at Pitt’s Wood.  Now he’s the sweetest boy you could hope to meet.  I’ve scheduled the photoshoot for Thursday.  We should have the variant outfits from Cynthia by then, and we’ll aim for two pageboy and two maid piccies.”
“Super.  Oh, by the way, for some reason he’s reluctant to wear his gloves tomorrow.  Is that a problem?”
Cassandra laughed.  “Oh, yes – he has a little thing about latex gloves.  I was just telling Nicola.  He likes to pleasure himself in his latex shorts and he likes to do it wearing his latex gloves.  So wearing both at the same time can be rather dangerous - if you see what I mean.”
Lucille raised her eyebrows.  “Really?”
“Probably better he doesn’t wear them tomorrow.”  She grinned.  “He understands that.  Serena can take them if she wants.  He can put them on when they leave.”
99
Active Sissy Stories
/ Re: His Aunt Nicole
« Last post by Simonssister on March 26, 2026, 02:38:55 PM »
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.”
100
Active Sissy Stories
/ Re: The Mother-Daughter Easter Brunch
« Last post by BabyJay on March 25, 2026, 01:29:58 PM »
I think the Boys are really enjoying the dressing up. Looking forward to hearing what their dresses are going to look like. Short and Lacey?. Whatever they are I am sure the 'Daughters' will look absolutely adorable.
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