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Author Topic: New Arrangements for Josh  (Read 119097 times)

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sweet baby katie

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Re: New Arrangements for Josh
« Reply #154 on: October 15, 2021, 09:23:48 AM »
Lucky Josh.  You are bringing out my envy.  Please continue.


Andlat

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Re: New Arrangements for Josh
« Reply #155 on: October 15, 2021, 02:33:57 PM »
Ooh, a cliffhanger! I can't remember what it is she has, but I can bet it's not good news for Josh!


sissyboy1212

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Re: New Arrangements for Josh
« Reply #156 on: October 15, 2021, 06:48:45 PM »
sweet baby katie, I am glad you enjoy the continuing story. Rest assured you are not the only one who is envious!

Andlat, yes a cliffhanger. I would politely disagree with you on one small point, however. I personally think it's WONDERFUL news for Josh! He might disagree if we asked him, however! :)

Thank you both for your kind comments.

sissyboy1212

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Re: New Arrangements for Josh
« Reply #157 on: October 18, 2021, 08:32:34 AM »
PART 42

“You’re very kind Dolores,” Gwendolyn spoke again to Mrs. Smyth. “When you mentioned seeing us yesterday at brunch, I remembered this flyer I picked up as we left the restaurant. Are you familiar with this ‘High Tea Tuesday’ event tomorrow?” Gwendolyn asked. “I wonder if they’d still have any tickets.”

“Oh yes of course,” Mrs. Smyth replied immediately, “It’s a festive time and you can buy tickets at the door. There should be plenty of room for all of you.” She explained, “Two or three times a year, the nice lady who owns the restaurant hosts a ‘High Tea.’ Everyone dresses up in fancy dress and we have an English-style tea with finicky little finger foods. They usually even have scones. Some people go all out with period costumes and everything. It’s a fundraiser for the Ladies Auxiliary. It’s mostly us girls in attendance of course but a few gentlemen show up now and then. You should all get dressed up and come!” she encouraged. As she said the last part about getting dressed up, Josh noticed that Mrs. Smyth deliberately turned her gaze back onto him. She was obviously already picturing him in her very particular idea of “fancy dress.” He shuddered slightly as he recalled the frilly, feminine outfits displayed prominently in her store windows.

“It sounds lovely, but I’m afraid we don’t have any clothes quite that dressy with us,” Gwendolyn said with a trace of disappointment. Hearing this, Kathy looked disappointed too. Josh had been listening to this conversation with growing dismay when it was obvious where it was headed. Consequently, he exhaled in thankful relief when he realized that he wouldn’t be subjected to that overstuffed tea party at least. Moments later, however, he knew he had celebrated too soon.

“Nonsense!” Mrs. Smyth said. “Did you forget who you’re talking to, Gwendolyn? You’ve already promised to visit my shop and this gives you a great reason! I happen to keep some extra vintage outfits in the storeroom at the shop and I’d be thrilled to find you some loaners. Over the years, some of the ladies have donated things they’ve used in the past so others can enjoy them, and I’ve wound up storing them since I have the space. Whenever we do the teas, many of the locals stop by to borrow items for free instead of buying costumes and things they will rarely wear. All I ask is that they cover the dry cleaning costs. I even have several outfits that Mrs. Meriweather gave me when her daughters outgrew them!” she added excitedly. “There are still plenty of nice things to choose from and I just know we can find something to suit you all.”

“You are too kind, Dolores. That’s very generous of you,” Gwendolyn said happily. She was delighted as she imagined her children in wonderfully fancy outfits for tea. Of course, the prospect of putting Josh in another gorgeously feminine outfit appealed to her immediately.

Mrs. Smyth spoke again, “Mrs. Meriweather might also have some things stored at her house that could work, especially items that might fit you Gwendolyn. You’re about her size. You should ask her. I know she’d be thrilled for someone to get some use out of those outfits,” Mrs. Smyth went on. “The tea is at three tomorrow afternoon. Why don’t you come to the shop around noon tomorrow and we will get you all sorted out for tea?”

“Of course we will. Thank you Dolores!” Gwendolyn said with anticipation. “I guess we’re going to high tea!” she said to her children happily.

“I can’t wait to get all dressed up in a fancy dress!” Kathy said eagerly. “Won’t that be fun Josh?” she asked her crestfallen brother.

All three of them—Gwendolyn, Kathy and Mrs. Smyth—turned expectantly to the sissified teenager. Once more the focus of overwhelming feminine attention, Josh was in disbelief. He felt the rug had rudely yanked from under his dainty, sandal-clad feet. “High tea and fancy dress?” he thought in horror. He tried to imagine what a girlish outfit he would have to wear tomorrow. His tummy fluttered and he felt lightheaded. Again, he remembered with dismay that all of this had been his choice. With a forced smile, he finally replied, “Th-that will be wonderful. I can’t wait… to get dressed up in pretty clothes for tea.”

“I must confess I am positively eager to put you in some lovely outfits!” Mrs. Smyth said gaily. “I’ve got a splendid dress in mind for you Kathy.” Then, fixing her attention fully on the feminized fifteen year old boy, she continued gleefully, “And of course Josh I have a few extra special ideas for such an extra special boy. Oh you’re in for such a treat!”

Gwendolyn, feeling slightly giddy, replied, “Feel free to go all out Dolores! It feels like a special occasion!” Then, unintentionally, she blurted the quiet part out loud, “No half measures!” Realizing what she had said, she held her breath and glanced anxiously at Mrs. Smyth.

Mrs. Smyth returned Gwendolyn’s look quizzically, but she did not reply. Instead, the two ladies silently locked eyes, and something unspoken passed between them. In that moment, Mrs. Smyth seemed to gain a deeper understanding of this unusual situation. Mrs. Smyth’s eyebrow arched slightly, and then Gwendolyn’s eyes softened a bit as she relaxed. Next, Mrs. Smyth nodded almost imperceptibly and her cheerful manner returned instantly. “See you tomorrow!” she called jauntily as she departed. “Hmm… no half measures,” she thought to herself.

Oblivious to this subtle exchange, Josh unconsciously brushed the delicately curly fringes from his forehead as he watched Mrs. Smyth march away purposefully. Undeterred, his springy new curls bounced back immediately to dangle adorably in place. He glimpsed his pink sparkly fingernails again as they flashed in the sun… his “Baby Pink Sparkle” fingernails. He realized his hand was trembling. He shivered slightly as his little man jumped, and he was suddenly acutely aware of his bra straps and lace-trimmed panties again. He grimaced slightly as he looked down only to see the baby blue floral romper hugging his slender body.

Permanent girly curls. Permanent nail polish. Hairbows, dresses, bras and panties. And soon, he would be delivered to Mrs. Smyth in her dress shop like a prettily wrapped present. He fretted powerlessly as he thought about her “extra special ideas” for him. His spirits sank even as his little man tingled more excitedly. Helplessly confused by his conflicting feelings, Josh sank inexorably deeper into his exquisitely sissy new world.

Andlat

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Re: New Arrangements for Josh
« Reply #158 on: October 18, 2021, 09:10:30 AM »
Goodness! Well, now I'm going to spend all day imagining just what outfit Josh has in store for him. A dress seems obvious, but with Josh being a thoroughly sissified boy, who knows what the extra special ideas could be!

CuddleBunns

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Re: New Arrangements for Josh
« Reply #159 on: October 18, 2021, 05:01:29 PM »
sissyboy1212, I am so glad you are continuing this story. There are so many stories here that dive deep into the world of humiliation, and while I love a good story where a sissy gets humiliated (and this one definitely has it's moments of embarrassment for Josh), there's an undeniable undercurrent of love and warmth to this one that makes it simply intoxicating to read. Gwendolyn clearly loves Josh and wants to make him the best little girly-boy he can possibly be. The idea that she loves feminizing him and it's beyond simply being a punishment at this point makes it all the more sweet. I can't tell you how envious I am that Josh has such a figure in his life to help guide his journey into sissyhood. I'm also very excited to see what kind of outfits Mrs. Smyth puts him in. You've definitley got a great thing going here. Keep it up!

sissyboy1212

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Re: New Arrangements for Josh
« Reply #160 on: October 18, 2021, 06:42:10 PM »
Thank you Andlat and CuddleBunns for your sweet comments.

CuddleBunns, you have hit precisely on the subset of these stories that truly appeals to me. Of course I love terribly embarrassing sissy situations, but I still want a heavy dose of sweetness mixed in. "Brute force" situations with nothing but extreme humiliation are just less interesting to me. To each their own. Thank you for hitting the nail on the head and I appreciate your kind feedback.

 

 

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