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Author Topic: New Arrangements for Josh  (Read 119071 times)

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sissyboy1212

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Re: New Arrangements for Josh
« Reply #49 on: July 01, 2020, 07:23:14 PM »
Sissy Little Girl, thanks for the nice comment. I am grateful that it struck a chord with you. Although in my story, Josh's mother has done (and will do) manipulative things, I am trying to paint her as a loving (but slightly weird and dysfunctional) mother. As I'm sure people on this board fully get, the actions directed at Josh by his mother and everyone else are inspired by things I'd wish were done to me.

For me, Josh is the hero (and the lucky winner) in the story. He's just not quite figured it out yet LOL.  He probably won't anytime soon :)

Thanks again!


dolly bo peep

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Re: New Arrangements for Josh
« Reply #50 on: July 02, 2020, 08:44:51 AM »
sissyboy1212,

I'm catching up and like Sissy Little Girl, sarahpenguin, and nappy1 enjoying your story.

It looks to me like Joshy is going to be presented as Kathy's little sister and the little beach town where they aren't know seems like an excellent place for him to develop his feminine presentation, and with it more acceptable habits which would carry over if he is ever allowed to go back to being a boy.

If the feminization process hits major snags, the threat of diapers could certainly be used.



Sissy Little Girl

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Re: New Arrangements for Josh
« Reply #51 on: July 03, 2020, 12:19:51 AM »
 :D Thanks for compliment, sissyboy1212.

sweet baby katie

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Re: New Arrangements for Josh
« Reply #52 on: July 03, 2020, 07:57:13 AM »
“...inspired by things I wish had been done to me.”   Sigh.... Yes.  Let that Muse continue to inspire you.

sissyboy1212

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Re: New Arrangements for Josh
« Reply #53 on: July 04, 2020, 07:04:31 PM »
PART 14

As Kathy bounced in, she was generally prepared for the situation that awaited her. In truth, similar to her mother, she had actually started looking forward to the idea of having a girly brother. It had been very difficult for her not to let anything slip during the car ride. On the trip, she had even daydreamed about outfits that would look cute on him.

She remembered well that when she was a little girl of six or seven, she had occasionally been able to persuade him to play dress up with her. One particular time, she was very sad and upset after her best friend moved away to another city. To cheer her up, Josh agreed to play tea party with Kathy and her dolls if she promised not to tell anyone. After she pleaded with him, he had even put on her pink dance tutu and a sparkly princess tiara from her Halloween costume. With a pair of his mother’s white tights and a Hello Kitty tee shirt that was oversized for her, he had looked great! She had begged him to let her put some lipstick on him, but that was where he drew the line. Still, they’d had a wonderful bonding time, and she treasured the memory. It’s one of the reasons she truly adored her brother. If he would do all that just to make her feel better, she knew he was still good inside. Would she actually get to relive that memory?

 Even with all that time to prepare, however, she still gasped when she saw her brother in his dress. She couldn’t believe how cute he looked. He looked just like a girl… and she was thrilled. “Wow!” she exclaimed, “Josh, you look so pretty!” Looking at her mother and then back at her brother, she said innocently, “but why are you dressed like that?”

Gwendolyn spoke so Josh wouldn’t have to, “Kathy, Josh has decided that he wants to explore girl things for a while. He thinks it will help him be a more sensitive and loving brother and son.”

“Is all that true Josh?” Kathy asked incredulously. Even though she had expected something like this, it still felt unreal.

Blushing a deep red, Josh looked at his mother first. Gwendolyn nodded slightly and silently mouthed the words “Tell her!”

Turning nervously to his sister, Josh finally spoke again, “Yes Kathy, it’s true. I’ve asked Mommy to help me. I hope you’ll help me too.” The crazy words seemed to be coming easier to him now. It was almost like he was watching a bad movie.

His use of the word “Mommy” was not lost on his sister, and she remembered the part about her pretending to be the big sister for a while.

Grabbing his hands, Kathy replied instantly, “Of course, Joshy. You’re my brother and I will love helping you. We’re going to have so much fun!” She then hugged him tightly, and tears formed in the corners of Josh’s eyes. He had always loved his sister, and her embrace moved him. “I love your dress,” she told her sissy brother. “Did you pick it out yourself?”

Turning plaintively to his mother, Josh saw the same look that indicated an appropriate answer was required from him. He was beginning to understand this routine by now, and he knew the type of answer that was expected. “Mommy picked it out for me, and I asked her to let me wear it. It makes me feel soooo pretty!” Without thinking, Josh drew out the word “so” in a very childish way. Why did he do that? His throat tightened a bit and a cold bead of sweat ran down the small of his back. What was happening to him?

After allowing a moment for Josh’s statement to sink in, Gwendolyn piped up, “Kathy, I was just thinking that Joshy’s hair needs some attention. Would you like to help?” Almost ecstatic, Kathy nodded vigorously in response.

“Well Joshy, shall we do your hair?” his mother asked. “With that cute dress, your hair is still much too boyish to go with it right now.”

The butterflies in his tummy went crazy again, but he felt powerless. Hating the words, but with less hesitation than before, he replied “Yes please Mommy.” He gave her another forced smile as a single tear finally fell out of the corner of his eye.

Kathy and Gwendolyn exchanged an excited look.

“Kathy dear, there are some packages on the bed in my room. Would you please bring them in here?” Gwendolyn beamed.

As Kathy scampered away, Gwendolyn pointed her son toward the ultra-feminine vanity dresser.

Sissy Little Girl

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Re: New Arrangements for Josh
« Reply #54 on: July 05, 2020, 12:03:44 AM »
sissyboy1212, I can't wait for the next chapter.  Josh is well on his way to girlhood.  Kathy is only too happy to help her brother become the sister she has so missed.  Somehow, I bet Josh is going to get pigtails for his new hairdo.  That way, he will look much younger than Kathy.

Keep it up, sissyboy1212.  You've got a fantastic story going.

sissyboy1212

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Re: New Arrangements for Josh
« Reply #55 on: July 06, 2020, 08:51:05 AM »
PART 15

Josh’s mother motioned for him to sit on the pink-cushioned stool. As his petticoat rustled and flitted ceaselessly, she showed him how to properly gather his skirt as he sat down and then smooth it out. The lacy hem of his petticoat settled breezily on his bare thighs. Grasping his small hands in hers, Gwendolyn folded them girlishly onto his lap for him. “Just keep them loosely folded like that on your skirt, dear, and your petticoat won’t push up so much. Correcting his posture, she added, “And please sit up straight.” She made some additional adjustments to his hand placement and pushed his knees and feet close together as if he were one of her favorite dolls. “It’s good for you to practice keeping your skirt in place, and this will also help you stop fidgeting so,” she added.

She turned the stool so he faced the mirror and lightly ran her fingers through his longish light brown hair. Humming softly, she picked up a hair brush from the vanity table and began brushing his hair. She occasionally prodded him gently whenever he showed any sign of slouching or allowed his knees to drift apart. Josh could only sit demurely as his mother methodically stripped away another layer of his boyishness.

Returning with the packages, Kathy was again amazed at the vision of girlishness her brother was becoming. As she put the packages on the canopy bed, she noticed for the first time the Sterncourt uniform still lying there. “Mom, what’s this for?” she asked a bit puzzled. Josh perked up at this unpleasant reminder. It provided additional incentive for him to follow through on his decision and commit to this surreal descent into girlishness. He’d made his bed, and he was going to have to lie in it. Even if it was a frilly pink canopy bed.

“Never mind that. I’ll put it away shortly.” Arching her eyebrow pointedly at Josh, Gwendolyn responded, “I don’t think we’re going to need it after all.” This was followed almost immediately by a single word: “Knees,” she admonished Josh as she pushed his knees together again--a little more firmly than before, “you don’t want anyone to see your panties, dear.”

Hearing this, Kathy tried to stifle a giggle. “He’s wearing panties?”

Gwendolyn replied, “Of course, and a little something else.” Continuing to Josh, “tell your sister about your pretty underthings, honey.  I know she’s curious and it’s quite all right.” 

Seeing no choice, Josh said with little enthusiasm, ”Mommy is talking about my bralette. It’s a pretty pink just like my panties. They are a matching set.” Kathy couldn’t believe her ears to hear her brother talking like this.

Smiling as she returned to Kathy, Gwendolyn asked, “Would you like to finish brushing out his hair?” Kathy nodded eagerly. Gwendolyn handed her the hairbrush and then moved to tend to the packages. Earlier, when Josh had stormed in the door, he hadn’t seemed to notice a number of packages on the doorstep. Gwendolyn had come to appreciate the value of online ordering and express delivery in this modern world.

The sight of her daughter sweetly brushing out her sissified brother’s hair filled her with a warm happy feeling. But then, with a trace of annoyance, she noticed that Josh’s legs were once more hanging sloppily apart. It detracted from the overall girlish image she hoped to achieve. “Knees, Joshua!” she corrected him yet again. Rapidly clapping his knees back together, Josh noted her use of his full first name with unease.

Then Gwendolyn had a clever idea. Grabbing her purse, she retrieved from it a slim, mirrored compact case which contained her cheek cream blush. The circular metal case had a pewter finish and resembled an oversized coin. Bending down, she once again pressed her son’s knees together and slipped the makeup case between them. “Joshy, honey, this little trick will help you remember your modesty. Just keep my makeup case pressed between your knees, and make sure you don’t let it drop,” she directed. He wasn’t certain, but Josh thought he detected the hint of a threat in her closing words. Squeezing his legs together to hold his mother’s cosmetic case in place also caused him to squeeze… other things. With the nervous squeezing against his ever-rustling petticoat, he was chagrined as a predictable physical reaction happened. Reluctant to test his mother’s patience, however, he was careful to keep pressing his legs together. She noted with satisfaction that his legs were finally staying together properly. It really made him look much more feminine.

Throughout all this, Kathy had continued working meticulously but lovingly with Josh’s soft hair. After a few minutes, her gentle brushing, and his focus on holding his mother’s makeup case in place, had put him almost in a trance. The seconds dragged by at an excruciating pace for the aroused teenage boy. He felt so girlish… boys just don’t sit that way. He was so embarrassed, but at the same time he couldn’t deny how strangely pleasant it felt to have his hair so tenderly brushed. Kathy, having gotten out all his tangles, used a comb to experiment this way and that with hairstyles that might suit him best. She finally decided his bangs were long enough to sweep them over to the side of his head. “Joshy, I think if we pull your bangs over like this it will be super cute!” she told her self-conscious brother. “Mom, do you have a hair clip?”

“I’m already ahead of you dear,” Gwendolyn replied with a grin. Setting a pink cardboard box on the vanity dresser, she dramatically lifted its lid. Josh ogled the multicolored array of girls’ hair accessories in the box with dismay. “I saw this starter set online and had them delivered here just for your brother,” she explained helpfully. “Of course I’m sure he’ll be happy to share them with you if there’s one you’d like to try,” she said with a twinkle.

As Josh cringed, his mother read the paper that was packed with the set: “This cute 36-piece pack of hairbows, clips and barrettes has options to match all her outfits and dresses. Great for every day or special occasions! With all these colors she will be the center of attention!” Gwendolyn added, “I think this is the right choice for today.” She lifted a large floppy hairbow fashioned out of pale pink and white gingham. It was at least five inches long and about two inches wide.

“Ooohh pretty!” Kathy cooed. “It matches his dress and it’s going to look darling in his hair. It’s perfect!”

 

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