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Author Topic: New Arrangements for Josh  (Read 119099 times)

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sissyboy1212

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Re: New Arrangements for Josh
« Reply #77 on: August 22, 2020, 08:38:00 PM »
Thank you both Sissy Little Girl and babycakes for the nice comments. I appreciate your taking the time to read and react.

Hugs!


Sissy Little Girl

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Re: New Arrangements for Josh
« Reply #78 on: August 23, 2020, 09:46:31 PM »
sissyboy1212, No problem.  You have provided a riveting story and you deserve all of the accolades that receive.  Keep up the good work and get that next chapter out.
 :P


jenniesissy

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Re: New Arrangements for Josh
« Reply #79 on: August 23, 2020, 10:23:59 PM »
Very much enjoying this delightful tale.  Thank you so much!

sissyboy1212

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Re: New Arrangements for Josh
« Reply #80 on: August 24, 2020, 04:37:49 PM »
PART 22

Seeing the dress, Josh knew at once he would be strapping on his polka dot sandals today. They were a perfect match for this girly-girl frock. He glumly examined it more closely. It was a delicate, baby pink sundress dotted all over with small black polka dots. Sleeveless with dainty spaghetti straps, it had generous off-the-shoulder ruffling across the top and around the hemline. The pink frock was made of a gauzy translucent material that looked incredibly feminine and wispy. An elasticized waist caused the skirt to flare out prominently. He detected multiple layers of the thin fabric rustling under the skirt which accentuated the flare even more.

“I just love this dress,” Kathy told her brother. “It’s made of chiffon. It’s a perfect summer dress. It’s just so light and breezy. It’s like something a fairy would wear. I can’t wait to get you in it, but there’s something else you need first!” Grinning, Kathy produced a thin plastic package and proceeded to open it up. “These white tights will be adorable with your dress, she added. Josh was horrified to see several rows of white ruffles on the seat of the opaque white tights as Kathy carefully removed them from the package.

Gwendolyn added helpfully, “Those are girls sandal toe tights, so there won’t be any unsightly seams on your toes. They are made to wear with sandals, and they’ll be lovely on you. Would you like to try on your tights now dear?”

Josh gulped softly and cleared his throat, “Ye.. Yes Mommy. Please let me put on my nice white tights now. The ruffles are sooo pretty.”

Kathy had him sit on the stool. She showed him how to gather his dainty tights at the toe and carefully slide them up his legs. Standing, he shivered involuntarily as he pulled them up over his panties and around his waist. His mother adjusted the frilly ruffles properly so they were nice and even on his bottom. Looking down, Josh saw the tights just made him look even more lithe and girlish. He felt new sensations of pressure and friction on his groin, and he was already having a physical reaction. He began to feel warm.

“Absolutely precious,” his mother said approvingly. “I was a little worried the Girls Size Large might be too small for a teenager, but they fit you perfectly.”

“Time for the dress!” Kathy announced. “Lift your arms, Joshy”

Josh smiled weakly and did as he was told, and Kathy slipped the gossamer-like dress over his head. It floated gracefully down into place and settled mid-thigh against his tights-encased legs. Kathy fastened a few buttons in back and then smoothed out her brother’s feathery skirt. She pulled the thin spaghetti straps into place and adjusted the ruffling off his shoulders just so. Stepping back to admire her handiwork, she was very pleased.

“Look in the mirror Joshy,” she said as she pointed him back toward the ornate full length mirror, “you’re adorable!” Josh saw his reflection and, just like yesterday, saw a waifish young girl staring back. This dress conspicuously highlighted his narrow, undeveloped shoulders unlike the boy clothes he normally picked to hide them. He looked and felt so… delicate in it. For the moment he was grateful, however, that at least it covered him up a bit down below. “And your other sandals will look fabulous with it too!” Kathy helpfully added, confirming his initial thoughts about the shoes.

“How does your dress feel, honey?” Gwendolyn asked pointedly.

“My dress feels nice and light, Mommy. The chiffon is so airy,” her son replied. The word “chiffon” just screamed sissy to him. He realized now that his bandeau bra paired wonderfully with this dress as well with no extra straps spoiling the look. He was chagrined at how slender and feminine he looked.

Kathy guided him back to the puffy stool and in no time at all had his matching polka dot sandals buckled snugly on his feet over the beautiful white tights. One, two, three, four, five, six tiny silver buckles in all.

“Those sandal toe tights really make all the difference. All nice and smooth with no sloppy seams,” Gwendolyn observed. “Don’t you love them Josh honey?” she prompted.

Josh studied his tighted feet strapped securely in his dainty pink polka dot sandals and wiggled his toes. It all looked so foreign to him. Then he answered his mother, “Oh mommy I love my tights. They feel so nice.” He felt a little shame as that second part was completely true. His little man could attest to that.

But his response was a tad too perfunctory for his mother. “Oh darling, you don’t really sound that excited. Use your words to express yourself, sweetie,” Gwendolyn continued. “I know you have an excellent vocabulary. Are they adorable? Or charming? Or perhaps delightful?”

Wrinkling his nose, Josh realized that his mother had upped the ante. What was good enough yesterday was obviously not enough today. He had to try harder. In a more bubbly tone, Josh exclaimed. “Oooh Mommy, you’re right! I do love my pretty ruffled tights with my chiffon dress. The whole outfit is simply… precious!” He tried to sell the enthusiasm, but he inwardly groaned as he heard the word “precious” escape his lips. Disturbingly, the whole exchange seemed to make his little man more active.

“Wonderful, darling!  Much better!” his mother said approvingly as more boyishness was scraped away.

Kathy grabbed the hairbrush and said, “I have a different idea for your hair today.” She brushed his hair straight back and pulled out a pretty pink hairband. The U-shaped accessory was covered in soft pink fabric, and she pushed it onto her brother’s head so that it held his hair back.

Josh was mesmerized as he watched her work in the mirror. At one point, he was startled when he heard his mother’s voice, “Knees Joshy. Remember your posture.” Josh immediately straightened up on the stool into a much more girlish position. Gwendolyn was gratified to see him clap his knees tightly together and fold his hands carefully into his lap as he had been taught.

“Yes Mommy, I remember,” he answered. He really didn’t want to hold the makeup case again. Forcing his knees and legs together this way already increased the maddening tingling caused by the tights. He didn’t need any added pressure. Kathy continued to work on his hair. She tugged and combed a few strands of hair forward to give him wispy bangs and soften his look. She teased it some more and then spritzed hairspray to hold the bangs where she wanted them. Josh felt the pink headband clinging gently to his scalp, and he figured there must be little grippers or teeth keeping it in place. Gwendolyn couldn’t resist snapping a few photos of her children in this sweet moment—Josh sitting so prettily in his dress and tights while Kathy lovingly styled his hair.

“Stand up honey, and let’s have a look,” Gwendolyn insisted as Kathy finished.

Josh stood and was once again a vision of sissy glory. Kathy and his mother fawned over how pretty and girlish he looked. “Give us a curtsy, Joshy” Kathy encouraged him, “Pleeease!” Smiling weakly, Josh demurely bowed his head and dipped into a dainty curtsy. Clapping, Kathy said, “I think that was your best one yet!”

“Thank you Kathy,” Josh bashfully replied, not entirely sure how to receive this compliment. Gwendolyn insisted on a few more pictures of him on the plush sitting chair by the window. Josh dutifully gathered his skirt and sat down as carefully as he could. Gwendolyn noted appreciatively that he smoothed out his skirt without being prodded. He looked momentarily unsure about what to do with his hands, but then he sighed and folded them prettily on his lap.

“Don’t forget to smile, sweetheart,” his mother directed. Silently cringing, Josh smiled feebly and posed girlishly while his mother took several more photos.

Satisfied, Gwendolyn put down her phone and said, “Kathy you should also go put on something nice. I’ll freshen up too. I’ve made us Sunday brunch reservations for later this morning, and we’ll leave in a bit.” Kathy squealed with delight and headed to change. Josh paled at the thought of going out again in public so soon, once again dressed like the perfect little girl. “Josh you can make up your canopy bed and then wait in the sitting room while we get ready, OK honey?”

“Yes Mommy,” the sissyish boy replied. Subconsciously, he swished his fluttery skirt as he stood and felt it tickle his tights-covered legs. Then he stepped carefully to the bed to make it up. He was very aware of his bra as he reached for the fluffy pillows, and felt a little air on his backside as he bent over to straighten the sheets.

Sissy Little Girl

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Re: New Arrangements for Josh
« Reply #81 on: August 24, 2020, 06:05:04 PM »
sissyboy1212, Joshy is really getting the full girly treatment from Kathy and Gwendolyn.  He is definitely having a hard (no pun intended) time with the tights.  And now, he gets to go to a Sunday brunch.  Sounds like fun!!!!
 ;)

sissyboy1212

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Re: New Arrangements for Josh
« Reply #82 on: August 24, 2020, 07:19:43 PM »
This is the inspiration for the lovely chiffon dress. Imagine it with smaller, black polka dots, a little more ruffling and several more layers under the skirt to make it very full.

And this is the inspiration for the polka dot sandals. I added the little silver buckles in my imagination.

Sissy Little Girl

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Re: New Arrangements for Josh
« Reply #83 on: August 24, 2020, 08:32:16 PM »
sissyboy1212, I love the images that you posted.  Your making me jealous and I want that outfit.  Keep going with this story and keep adding those visual post, too.

 

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