New Arrangements for Josh

[dolly bo peep]

sissyboy1212,

I enjoyed reading your nicely detailed next steps in Josh's transformation.

Getting used to wearing dresses with petticoats, and modifying his posture will certainly take some effort, in addition to enduring having a feminine hairstyle, with hair clips, barrettes, and ribbons included.

I'm eager to read what happens next.

[Sissy Little Girl]

sissyboy1212, the detail that you use in your story is amazing.  Poor Josh is starting to look like a young girl.  I am sure that Kathy and his mom are enjoying this no end.  He is also learning deportment from his mom on how to sit like a young girl.  The box of hair bows, barrettes and other accessories are a fantastic addition.

I can't wait for the next chapter. :P

[sissyboy1212]

PART 16

With a sinking feeling, Josh sat motionless as Kathy worked a small dollop of styling mousse into his hair to make it “a little more poofy.”  Then she gathered his bangs and carefully twisted them together onto the right side of his head. Pulling his hair gently as she teased it into place, she took the prissy gingham bow from Gwendolyn and used its attached alligator clip to secure everything in place. She made a few last adjustments and stepped back to inspect her work. Josh immediately felt the alligator clip exerting a constant light tug on his hair as if to remind him it was there. Studying his reflection, Josh saw that the cutesy hairbow pulled his hair back in a way that framed his face adorably. “I’m such a fairy now,” he said softly to the mirror.

   â€œSissy, dear. You’re much more of a sissy than a fairy,” Gwendolyn gently interrupted him. This startled Josh as he hadn’t meant to speak out loud. “But you can ask to be a fairy for Halloween if your heart is set on it!” she chuckled lovingly.

This remark brought another fond memory back. “You’ve already sort of done that anyway. Remember when you were twelve you went as Peter Pan? You looked so cute in your little green leotard and that adorable Peter Pan hat!” Even though he had thought he was getting too old for trick or treating, he had agreed to go as Peter Pan because Kathy wanted to be Tinkerbell. She had begged him to go with her. He had to admit it was a great costume
 especially after he let his mother put some light makeup on him to add freckles and make his cheeks more rosy. The crowning touch had been a dusting of sparkly glitter makeup to match Kathy’s. It had wound up being more effeminate than he had expected, but it was a lovely time even if a few folks had snickered at his costume. His unguarded reference to a fairy had obviously met with Gwendolyn’s approval. “Don’t you just love your hair like this sweetheart?” she prompted him.

   Becoming more accustomed to this ritual, Josh replied, “Yes Mommy I feel so pretty. I just looove the way my hairbow goes with my brown hair. Kathy, thank you so much for doing it for me.” Josh gushed a little more than he truly intended, and for some reason he had stretched out the word “love” very girlishly. God he sounded so sissy-ish.

   â€œBrunette,” Gwendolyn corrected him. “We call girls and girly-boys with brown hair ‘brunettes.’” From the start of this, she had schemed for him to say and repeat girlish and childish words as much as possible. In time, she hoped that it would have a subduing effect and he would talk like a sweet little girl all the time without thinking.

“Thank you Mommy. Of course I meant ‘brunette.’ I really adore my cute gingham hairbow. It goes so well with my
 brunette hair,” Josh replied. Gwendolyn noted approvingly that her prodding was already generating the desired effects. Her son’s answers were growing longer and more flowery.  Josh had always possessed an excellent vocabulary, although over the last year he had hidden it behind faux-rebellious teenage boy posturing. She was so tired of hearing “yeah” and “uh-huh” from him. And every time she had asked him how his day was and received a sullen “OK” in reply had bothered her to no end. She intended to bring his vocabulary back and make him use it. Especially the sweeter and more refined parts of it.

Kathy bent down and kissed him sweetly on the cheek. “Oh Joshy we are going to have such fun together! It makes me so happy that you’ve decided to do this,” she told him excitedly.

   Gwendolyn smiled appreciatively for a moment at her two children. Turning to Kathy, “The other boxes have his new shoes. Would you get them please?” Then she addressed her girlified son, “I couldn’t decide which ones would look the best with that adorable dress, so I have a couple pairs for you to try and choose from. We need to start building your wardrobe anyway. Won’t that be fun, dear?”

   â€œOh yes Mommy. I’m sure they are all wonderful and I can’t wait to try them on,” he replied almost automatically if still flatly. His weak smile was still forced, but perhaps a little less so.

“Joshy these are both so precious. You’ll have a hard time choosing!” Kathy said gaily.

   â€œShoes
 great,” Josh thought dejectedly, “I’m a brunette, and now I get to try on girls’ shoes. At least I know what’s coming next.” He remained highly conscious of the hairbow’s foreign presence in his hair, and in the mirror he saw it bounced a bit every time he tilted his head. His fine facial features looked very girlish. And of course he continued to carefully press his mother’s cosmetic case between his knees. The throbbing under his skirt had subsided somewhat but it was still there. The little appliquĂ© butterfly on his gingham bib seemed to giggle at his predicament. He was reluctant to risk moving his hands, so they remained folded daintily on his lap. In exquisite agony, the jittery teenaged boy wriggled his bare toes on the plush rug and sighed.

[Sissy Little Girl]

sissyboy1212, Oh, poor Josh.  Inside, he is hating his girlified appearance and when he answers, there is no joy there.  I wish I could have had this done to me; but, that didn't happen.  I had to wait till I was 44 to become my true self.

Keep up the good work. 8)

[bobbie99]

In everyday life there are choices,  Josh was at the cross road and given two choices by his mother.  Going forward or back was not an option.  A great opening to your story.  Now the decision is on shoes.  In this decision it can be either one or the other, or perhaps both.
Then there is the authors decision.  To Continue the story or not.   Sissyboy, I hope you decide to continue the story.  Please

[sissyboy1212]

Thank you for the kind words and encouragement.  I definitely intend to continue this adventure. Life gets in the way of writing sometimes though. There is more to Josh's story, but it will come in time.

[sissyboy1212]

PART 17

As Kathy eagerly brought over the first pair of shoes, their mother retrieved her cosmetic case and then swiveled the feminized boy slightly on the stool to face Kathy. “I’ll take this back while you try on your shoes, but remember your modesty sweetheart,” she cautioned him. Josh was relieved to relax his knees but then he groaned softly as he saw the shoes. 

They were a very girlish pair of cute open toe white patent sandals with a low block heel. The sandals had buckle ankle straps with narrow straps that looped gaily across the top of the foot.  As Kathy knelt down to strap them on his feet, Josh couldn’t take his eyes off the little white flower applique on top which practically screamed “Girly Girl!” Kathy expertly slid them over his feet and then buckled the shiny white straps snugly around his ankles.

“Well stand up honey and let’s see them on you,” Gwendolyn beamed.

Josh stood up a little unsteadily and took some tentative steps.

“Those are adorable!” Kathy exclaimed.  “I just love how strappy and cute they are on your feet.  And those flowers on top are just to die for!”

Looking at Josh, Gwendolyn asked “What do you think darling?”

“Oh Mommy,” the sissified boy began almost without thinking, “they are so pretty.”  Cringing, he continued, “I just love the little flowers on top.” He hoped that was sufficiently gushy.

“Give us a twirl Josh,” Kathy prodded.  Reluctantly and carefully, Josh turned slowly around causing his petticoat and skirt to rustle and swish.
 
“I agree that those really do complete the outfit,” Gwendolyn agreed. She also noted with satisfaction that the summery sandals fit his small feet perfectly. She had done her homework on sizes before ordering them online. They made his feet look even more delicate and deliciously feminine.

“Should we try the other pair, Mom?”  Kathy asked. 

“Those really are perfect, but we'll let Josh pick since he's the one who will be wearing them." She then added with a knowing look, "After all this is all his choice." 

As the embarrassed boy stood there, Kathy retrieved another pair of sandals. “Those are just as girly as these,” Josh thought glumly. This low-heeled pair was a soft pink with even narrower straps to encircle the foot and ankle very delicately. The straps were dotted with small black polka dots, and Josh counted two, no three, shiny little silver buckles on each. They looked like a nightmare to get into. At least the ones he had on his feet now were white and not pink. Maybe that was something.

“Mommy, if it’s all right I think I will stick with my cute flower sandals,” Josh decided. “I think they go better with my pretty dress,” he added just to be safe.

Gwendolyn eyed her son for a moment, and then smiled warmly. “I agree sugarplum, those white sandals look so precious. You've made a great choice! You will have lots of chances to wear the other ones. Besides, I think it’s getting time for something to eat.”

His mother guided him back again to the full length mirror, so he could take in his completed look. Looking at himself, Josh saw nothing but a pretty little girl staring back. His floppy gingham hairbow was pinned stiffly in his long hair.  The bow sash on his pink gingham dress made the petticoat poof out and tickle his legs. His fussy little girl collar was snug around his neck, his strappy flower sandals just completed the sissyish look. Josh couldn’t believe how quickly this had happened to him.

Gwendolyn was overjoyed with her son’s transformation. There was hardly a trace of that rambunctious fifteen year old boy that had barreled through the door a couple of hours ago. “I’ve got some sandwiches in the kitchen. After that, I think it would be nice to stretch our legs and walk into the village.”

Kathy giggled and headed for the kitchen. For a moment, Josh froze. Somehow, up to this point, he had thought that maybe he would just stay in the house. The idea that now he would have to go out in public dressed this way brought a whole new wave of anxiety over him. “Into the village?” he croaked the question.

“Of course, silly,” his mother responded. “You didn’t get all dressed up to stay in the house, did you? It will be a marvelous chance to show off your new dress.”

“No half-measures,” Gwendolyn repeated the mantra happily to herself. 

Lightheaded, Josh started taking small mincing steps toward the bedroom door to maintain his balance as he started to get used to his flowery, unfamiliar shoes.