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Author Topic: New Arrangements for Josh  (Read 119115 times)

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sweet baby katie

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Re: New Arrangements for Josh
« Reply #84 on: August 25, 2020, 08:30:04 AM »
I love the dress... it is totally dreamy.  Girls are so lucky.


babycakes

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Re: New Arrangements for Josh
« Reply #85 on: August 25, 2020, 10:24:01 AM »
Many thanks for the images sissyboy!  They really add to the story.  After all, a picture is worth a thousand words!  :D


Sissy Little Girl

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Re: New Arrangements for Josh
« Reply #86 on: August 25, 2020, 11:59:47 AM »
I love the dress... it is totally dreamy.  Girls are so lucky.

Yes, Sweet Baby Katie, we girls are lucky.  We get to wear dreamy outfits that make feel like we are princess'.  To take a phrase from the musical, "Bye, Bye, Birdie," I enjoy being a girl.

sissyboy1212

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Re: New Arrangements for Josh
« Reply #87 on: August 25, 2020, 06:45:28 PM »
PART 23

Josh made his bed like his mother wanted. (For the last 24 hours, he had been making his bed in more ways than one!) As he gazed around the girly room, it dawned on him that this was one of the few times he had been alone since this whole ordeal started aside from sleeping. He looked at the gauzy canopy bed and the little pink ribbons dancing down. Shifting his gaze to the dolls, he realized that’s almost what he felt like… a pretty and fragile doll. He examined the dolls more closely. There were three of them, and he saw small engraved nameplates on the bench. He hadn’t noticed those before. Their names were Penelope, Maddie, and Eliza. Penelope was wearing a pink gingham dress resembling the one he wore yesterday. She had blonde pigtails tied in pretty pink bows and wore pink patent Mary Jane shoes. His closet door was still ajar, and he saw his own gingham dress hanging there sweetly. Without really thinking, he picked up the doll and walked to the closet. Holding Penelope, he lightly brushed the lacy petticoat of his hanging dress and compared the dresses. Remembering he was supposed to go wait in the sitting room, he closed the closet door. Absentmindedly, he propped Penelope up on the bed instead of putting her back on her bench. He’d move her back later.

Sighing, he returned to the full-length mirror. The bashful little girl looking back was a picture of sugar and spice. Fifteen? He knew he looked ten or eleven at the very most. His thoughts drifted back to his dream. His little man perked up just remembering it. The way the tights felt constantly reminded him of being suc-ked down into the big pink cushion. His bedroom door was open, but he was all alone in the room. He took a deep breath and smelled his floral scent. Whatever this was, he knew down deep, was better than Sterncourt.

On a whim, he grabbed his skirt and playfully swished it around while he watched himself in the mirror. His breath got a little quicker. He started to feel the familiar taboo mixture of arousal and shame that had been teasing him throughout this entire process. He knew he should stop, but nonetheless he kept swishing his skirt back and forth. Swish, swish swish. It fascinated him to watch the chiffon dress dance and rustle over his tights. HIS chiffon dress and HIS ruffled tights. He paused for a moment as if in thought, and then he slowly lifted his skirt just enough in back to run his fingers across his ruffled bottom. It all felt strange and forbidden. Chiding himself silently, he pulled his hand back abruptly and let his skirt waft back down. His little man was fully awake now—but buried deep under his floral panties, ruffled tights and chiffon dress. Josh touched the front of his skirt to adjust himself through all the layers of girlishness, and it felt electric. He had to stop.

Yanking his hand back again, he shook his head sharply and stepped off the plush rug onto the hardwood. His polka dot sandals made a soft clacking noise on the polished wooden floor. Despite himself, he turned again to the mirror. The way Kathy had styled his hair with the pretty pink hairband really made him look younger. He touched the hairband and the fabric covering was surprisingly soft to the touch. He stopped to listen intently. He could hear the faint noises of his mother and Kathy getting ready elsewhere in the house, but they weren’t nearby. He wasn’t sure exactly why he did what he did next. Studying his reflection closely, he curtsied as gracefully as he could.

Spying the swivel stool, he listened carefully again. Still no one nearby. He pulled the stool out where he could see it in the mirror and then sat down. He tried to sit demurely and keep his legs together. “Knees, Joshua, Knees!” he reprimanded himself. He watched himself in the mirror as he folded his hands various ways. Sitting like this, his hands were folded on top of his chiffon skirt right above his little man. He squeezed his legs together tighter and shuddered slightly. It felt very nice, but he was wary of making another “little squirtie” right now. He was playing with fire.

He pushed off with his feet to spin around on the stool and straightened out his legs as he twirled. The white tights were such a contrast with his colorful skirt and shoes. He stopped spinning and breathed deeply. Surrendering hesitantly to temptation, he pulled his skirt up again with one hand. With the other, he tickled the front of his tights and closed his eyes. His pulse accelerated. In his mind’s eye, he was tumbling through the air again high above the satiny pink cushion. He hooked his thumb in the top of his tights and slowly began to pull them dow—

“Josh! where are you, honey? We’re ready to go!” he heard his mother call abruptly. Snapped rudely from his trance, his face grew hot. He heard her footsteps in the hallway now. “Josh, I don’t want to be late!” she called again.

Josh smoothed his skirt frantically. His frustrated little man was practically screaming at him. “I’m coming Mommy, I’m coming!” he squeaked nervously. He could tell she was near the open door.

A second later, Gwendolyn appeared in the doorway. She saw that the canopy bed had been neatly made as she asked… but why was there a doll on the bed? Josh was blushing furiously. And why was the vanity stool in the middle of the room?

Gwendolyn turned a probing gaze on her son. Josh was crimson. She didn’t know precisely what was going on here, but her intuition was whispering to her, and she had suspicions. Whatever Josh had been up to, however, she sensed that it was not necessarily disrupting her plans right now. She felt sure she would ferret it out in time.

Her gaze lingered a bit longer on her fidgeting sissified son. Then, with a sly grin, she delivered another little nudge. “Oh I see you’ve been playing with the pretty dolls. How sweet! But, come along, honey. It’s time for brunch! You can have more time with your dollies later.”

Humiliated even more, Josh silently chastised himself for leaving the doll on the bed. Still, he was eager to escape this moment and quickly blurted out using his best sing-song voice, “Yes Mommy of course! I can’t wait for our lovely brunch!” His little man was still angry, but it was starting to calm down. Now his mother thought he was playing with dolls—which was basically true—but at least she didn’t know the rest.

Sissy Little Girl

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Re: New Arrangements for Josh
« Reply #88 on: August 25, 2020, 09:23:49 PM »
sissyboy1212, Josh is getting deeper into his girlish way of life.  Unfortunately, he can't catch a break and his mommy or Kathy always see to show up at the wrong time.  He even made a mistake of leaving Penelope on his bed and had his mom see it there.  Now, she thinks he likes to play with dolls.  Better buck up, Joshy because you are in this for the long haul.
 :P

bobbie99

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Re: New Arrangements for Josh
« Reply #89 on: September 10, 2020, 11:58:40 AM »
Please continue the story.  Excellent story line so far.  Like Josh I would not have chosen military school and the excessive discipline.  After all this girl thing is for only a few weeks while we are on vacation right?  Sure it is Josh.  Keep thinking that.

Again please continue.

sissyboy1212

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Re: New Arrangements for Josh
« Reply #90 on: September 12, 2020, 12:48:44 PM »
PART 24

Josh saw Kathy had changed into a sleeveless navy dress. She looked every bit a maturing teenage girl. Tastefully dressed but still casual. In her modest heels, she practically towered over him now. Anyone would think he was her little sister.

They all piled into the car. Normally, Josh would have barged his way into the front seat, but he was moving more carefully now and was relegated to the back. He had a bit of trouble gathering all his dress as he got in the back seat, and Kathy had to buckle his seat belt when he couldn’t find the connector under his frothy skirt. Even in the car, his mother had him keep his knees together. “Practice makes perfect, honey” she admonished.

Arriving at the cute little restaurant by the water, they were seated at a lovely little table by the window. It seemed to have a bit of an old English theme. The restaurant was busy with the brunch crowd, and Josh was keenly aware of people looking at him. Other boys and girls with their families seemed to be wearing mostly shorts. He didn’t see many skirts or dresses, so he stood out somewhat. He felt sure they all thought he was just a pretty little girl, and he tried very hard to look the part. He just concentrated on maintaining his posture and keeping his skirt under control. He especially focused on keeping his legs clamped together, wary of his mother’s cosmetics case. Sitting in this crowded restaurant on his chiffon skirt in his panties and tights made him feel constantly uneasy.

They enjoyed a nice meal, though, and Gwendolyn again noticed how Josh ate more delicately. He was definitely preoccupied with the way he was dressed. As they finished, Josh was chagrined to see a familiar face approach their table. It was Mrs. Smyth from the dress shop!

“Well hello, Gwendolyn, how lovely to see you all again today,” Mrs. Smyth greeted them. Josh was nervous. She knew his secret.

“Thank you,” Gwendolyn replied, “we look forward to visiting the shop.”

“As do I,” she smiled. There was another nicely dressed lady with her. “This is my good friend Andrea. She runs the salon across the street from my shop, and we’ve been friends for years.” Turning to Andrea, she added, “these are the Hartleys. They are visiting and staying at the Meriweather place.”

“I’m Andrea Lewis. It’s a pleasure to meet you. Don’t you all look lovely!”

Gwendolyn thanked her and Kathy introduced herself. To Josh’s horror, Mrs. Smyth gestured to him next and spoke softly, “Andrea, this is the one I told you about.” And then she whispered loudly, “Can you believe he’s actually fifteen?”

Mrs. Smyth spoke to Josh with a knowing smile, “that is an adorable dress, dear, and I know my frocks! I love the spaghetti straps. They accentuate your petite shoulders so nicely. You’re lucky to have a marvelously narrow frame. Those sandal toe tights emphasize your slender legs and contrast well with that skirt color. Would you indulge me and stand up so I could appreciate it all better?” 

Josh was blushing furiously and seemed unable to speak. With her years of experience in fashion, Mrs. Smyth easily recognized and noted every girlish detail of his appearance. Already sensitive about his slight build, Josh winced as she immediately made it the focus of her trained eye. Gwendolyn prodded him, ”well what do you say, honey?”

“Thank you for saying all those sweet things, Mrs. Smyth,” the embarrassed boy finally replied, “Of course I’d be thrilled to show you my dress.” Josh got up carefully and stood awkwardly by the table. Other diners were starting to notice this exchange. In such a small town, it was obvious that most of them knew each other anyway. His mother had him turn around so the ladies could see the back, and he unconsciously twirled his skirt as he did so.

A small girl with her family two tables over called out, “Oooh so pretty! Mrs. Smyth did that dress come from your shop?” She stood up to get a better look. An adolescent boy sitting next to Samantha, obviously her brother, rolled his eyes and turned back to his plate. Now more people were watching.

“No Samantha,” Mrs. Smyth called back, “but I have some lovely ones that are very similar.”

Then she whispered to Gwendolyn, “she is a lovely child, but her brother Justin is a terror—nothing at all like your sweet Josh here. They practically let him run wild!”

Gwendolyn watched all this play out with amazement and delight. How had she been so fortunate to literally stumble upon such a wonderful ally? She’d really had no more elaborate plans for the morning than just getting Josh out in public in another pretty outfit. Dolores Smyth, however, was reinforcing everything that she was trying to do with her wayward son. This was an unexpected godsend. “If she only knew…,” Gwendolyn mused to herself, thinking of how different the reaction might have been to the naughty Josh of last week. Elated, she exchanged a knowing look with Kathy and squeezed her daughter’s hand.

 

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