New Arrangements for Josh

[dolly bo peep]

sissyboy1212,

I really enjoyed the last chapter.

You are doing an excellent job in building the tension while we do have a good idea of where this is leading. I liked the detailed description of what would await at the military boarding school.

A lot of us are anticipating the delicious details of the alternate choice.

[sissyboy1212]

PART 8

“But of course, there is the alternative,” she continued. Looking him in the eye she added, “To be absolutely clear, this is all your choice.”

Josh looked forlornly at the second set of clothes. They had to belong to his sister, but as he looked at them more closely, he was crestfallen to realize they would almost certainly fit him. Between his late development and his sister’s accelerated maturity, he had been dismayed for a while now that she was taller than him despite being three years younger. (Every time this was pointed out, he inevitably turned bright red and sulked.) 

“I’ll admit this choice is a little less… pre-determined… than going off to Sterncourt. It would truly be a bit of an adventure we would take together as a family without knowing exactly where we wind up. But the world as you know it will be turned a little on its side,” she added with the barest hint of a mischievous grin.

“The basic idea would be to help you rediscover your inner goodness. Kathy is younger than you, but she is more mature. The idea would be for some of her maturity to rub off on you. But to get there, we have to give you a behavior re-boot, so to speak. I thought this was pretty out there, but after talking to your Aunt Karen, I found out there are more families who’ve tried this type of thing then you might imagine.”

“To be blunt, you would basically turn to a more feminine way of life for a while to bring out the softer and kinder parts of you. A key part of that will be dressing the part. It doesn’t matter to me if you want to truly be a girl or just be a boy who likes girly things. The clothes and dress are an important part of making a clean break with your ruinous ways.”

“I’ll admit, the thought of having two daughters, or even one daughter and one sweet son who loves girly things appeals to me. It will be a little harder for all of us, but I’m willing to do it for your sake,” she said to the petrified teen.

His mother’s statement hung in the air for an uncomfortably long time. Josh felt lightheaded as if he were in a bad dream. 

His thoughts ran wild and were completely scattered. “This can’t be happening… does she mean to make me a girl? I’m a teenage boy! I’ll be miserable if I have to go to that military school… but I’m a BOY! I’m not some sissy girl.” In a final fit of resistance, the panicked boy blurted out, “This is stupid!  I won’t do it!  Where are my normal clothes!?!”

With sudden speed, Gwendolyn Hartley stepped forward and grabbed her son by the arm. “Joshua Cassidy Hartley! I’m trying to save you from yourself and you will do this!” she said sternly. He had barely registered the fact that she used his full name (which she only did when she was really upset) when, shocking her son completely, she sat on the side of the bed, yanked him over her knee and began swatting his behind. 

As he received the first spanking he could remember since he was a toddler, the teenaged boy was distraught. Truthfully, the spanking was not delivered with much force at all, but the emotional impact of the unexpected turn of events pushed the boy over the edge. Embarrassed and confused, he suddenly burst into tears surprising them both. After only 5 or 6 swats, his mother stood the red-faced teen back up.

“I know this is a lot to take in, Joshua, but I am determined to see this through.” She returned immediately to the decision confronting him. “Your old clothes are not here. Either way, you won’t be needing them anymore. These are your options. What will it be?”

Defeated and still sniffling, Josh brushed his hand across the Sterncourt tee shirt. It felt rough and starchy. Hesitating again, his heart sank as he realized how rapidly and unexpectedly this moment of decision had arrived. Noting his reluctance, his mother said, “I was afraid the other option was just too far out there. I’ll make this easier for you. Let's get you ready to drive to Sterncourt.” She exhaled slowly, almost wearily,  with an obvious air of disappointment.

“No,” Josh said in a very soft, wavering voice. He could not yet meet his mother’s eyes. Gwendolyn paused, arched her eyebrow and watched him expectantly. After another excruciating silence, he finally looked up at her with a quivering lip. His face still red, Josh couldn’t believe the words that came out of his mouth next. In the same small and childish voice, he said “No… you said I could choose.”

With dread, Josh fixed his gaze on the pair of pink nylon panties lying on the bed. They were an ultra-girly, baby pink color with a hint of satiny sheen. Dainty ruffled white lace frills circled the waistband and elasticized leg openings. The lace was accented with tiny pink satin bows atop the delicate frills.

“What is your choice Joshua?” his mother asked more gently. She softened as she caught a fleeting glimpse of the sweet little boy her son used to be. 

Josh opened his mouth slightly but couldn’t speak in reply. He just couldn’t find the words. Instead, with a trembling hand, the chastened teenage boy reached reluctantly for his new panties… and his new life.

[PervScenes11]

Part 8 is beautifully written and Josh's choice is well-dramatized.

[Sissy Little Girl]

sissyboy1212, WTG!!!!  Josh had a big decision to make.  Go to Sterncourt and learn military discipline or dress like a girl and develop his softer, more feminine side.  I think Josh is going to love being a girl.  Can't wait to read more. 8) 8) 8) 8) 8)

[sissyboy1212]

Thank you both for the lovely comments. Things are heating up for poor Joshy now.  I've written a bit ahead and am trying to chart out a lovely little journey for him. Installment writing means you can't go back and change the beginning, so I'm trying to keep in mind where he is headed.  Glad you enjoy!

[Sissy Little Girl]

sissyboy1212,  I can't wait for the next chapter.  You have me on pins and needles waiting for your next chapter.  Thank you for the compliments because we REALLY do love this story. 8) 8) 8) 8) 8) 8) 8)

[sissyboy1212]

PART 9

Incredibly unsettled, Josh turned from his mother, dropped his towel and stepped nervously into the panties. He shivered as he tugged them up his smooth legs. Unlike some of his peers who were proudly sporting new body hair, he had just the barest beginnings of nearly invisible peach fuzz. He shuddered when he pulled his panties slowly into place. They fit snugly against his skin and boy parts. The panties were so silky and smooth… unlike his normal underwear. He was suddenly horrified as his little man reawakened. Reluctantly turning, the sheepish teenaged boy now stood before his mother with his frilly new panties on full display.

Gwendolyn appraised her wayward son with satisfaction as he took those first tentative steps. If this worked as planned, Josh would soon lose his balance and slide irreversibly into a new girly world. She had some extra “pushes” planned to make it certain, of course. To avoid spoiling the moment, she forced herself to remain silent. She discreetly noted, however, the physical reaction that added to her child’s discomfort. She reassured herself that a plan was already in motion to address THAT little problem.

She stole a glance at her watch. Incredibly, they had only been in this house about two hours. My how quickly this had progressed! Her original plan had been to start either in the evening or tomorrow morning. But the opportunity had presented itself when Josh rushed so selfishly into the house to shower, and she took it. Karen’s admonition to avoid “half-measures” was lodged firmly in her brain. “Rip the Band-Aid off cleanly indeed,” she thought with a smile.

In truth, this notion had taken root in Gwendolyn’s mind. Over the course of the last week, this had grown from a half-baked idea to correct her son’s behavior into… something else. The idea of Josh becoming more girlish filled her with happiness. Josh had always been, if not feminine, then at least sensitive. He was never a rough and tumble boy. She felt certain this recent “bad boy” act was not his true nature. She wanted to help him uncover whatever was there. And, she had to admit, she secretly loved the idea of him being feminine and girly, or even sissy. She had always hated the macho crap anyway. With a full heart, she snapped back to the present.

“Oh Joshy don’t you look sweet!” she said softly when she couldn’t hold it any longer. Gwendolyn beamed and spoke, “How do you like your panties sweetheart?” 

Josh’s response could not properly be categorized as words. A little squeaky croak was all Gwendolyn could detect. She smiled at him and said gently, “Joshy, we will have to work on your communication skills as we go forward.”

His head spinning, Josh felt he had stepped into an alternate reality. He had just agreed to… what exactly? To be a girl? Or just dress like one? Or be a sissy boy? Or something else in between? But, unbelievably, he had actually chosen this! Maybe military school was a better way? “No,” he finally decided, “whatever this is will be better than Sterncourt.” It seemed to be the least bad choice, but still he had made the choice to pick up those panties… now his panties.

Josh grimaced as he deduced what was supposed to come next. Still reeling, he held his breath and hesitantly reached for the next dainty item. It looked like a bra, but it was much more childish than the ones he knew Kathy wore. He guessed it was some kind of training bra. It matched his girly pink panties and was adorned with the same delicate elasticized frilly lace and tiny bows. They were obviously a matching set. Skinny pink spaghetti straps went over the shoulders and he assumed, correctly, it must go on over his head like a cropped tank top as there was no clasp in the back.

He held it gingerly for a moment as if it might bite him. Gwendolyn spoke carefully, “It’s called a bralette. It’s a sort of first training bra for little girls who haven’t started developing but want to get used to wearing one.  You don’t really have a chest at all yet, so I thought this would be perfect for you. Let me help you with your new bralette.”

“My bralette?” he cringed silently. Even the word “bralette” was such a sissy word that it seemed to cause him physical discomfort at just the sound of it. “What a weird word,” he pondered aimlessly. The word “bralette” conveyed a level of girlishness that “bra” alone didn’t approach. With Gwendolyn’s coaxing, he returned to the moment and hesitantly lifted his thin arms up. She deftly slid his new “bralette” over his shoulders and adjusted it onto his bosom. “Chest, dammit,” he thought. “I have a chest not a bosom!” What was happening? Second thoughts crept in. Was this really better than going to a military school?

Gwendolyn fussily adjusted the willowy shoulder straps until they lightly caressed his slender shoulders in just the right way to gain her approval. Further chagrined, Josh gloomily eyed the large pink bow centered on his slim chest. He suspected the material in his bralette must contain some spandex as the silky fabric hugged his skin snugly. He briefly focused on the ruffled lacy trim that now encircled his torso. An electric tingle ran through the cringing 15-year old boy as he stood in his new bra (bralette?) and panty set.

Abruptly, he gasped. For the first time, Josh glimpsed himself in the full-length mirror. He awkwardly stepped toward it. With his long, just-washed hair, smooth skin and delicate build, he was horrified to see that he looked like a tween girl in her (his?) new frilly undergarments. (Pronouns were becoming confusing.) He inhaled another whiff of the strawberry scented shampoo. How had this roller coaster of events come so far and so fast?  What had he agreed to? He stood transfixed by his reflection. His heart raced and his feet were glued to the floor. He lost track of time, mesmerized by the red-faced girly-boy staring back at him.