Due to Betty's recent illness, most of Betty's sites are limited to members only, and no new registrations for memberships will be accepted at this time.

Trans News ~ Headline News ~ Science News ~ Tech News ~ Paranormal & Aliens
Odd News ~ Betty's YouTube ~ My other channel


The more you give, the
more we can give back!
There has been,

Hits to Betty's
Pubs since
Sept. 30th, 2004

Author Topic: New Arrangements for Josh  (Read 119046 times)

0 Members and 18 Guests are viewing this topic.

sissyboy1212

  • Ultimate Sissy
  • *********
  • Posts: 193
  • Karma: +11473/-5
Re: New Arrangements for Josh
« Reply #35 on: June 23, 2020, 08:20:51 PM »
PART 10

Gwendolyn interrupted her confused son’s thoughts. With a start, Josh realized his mother had drawn close to his side. Lost in his own head, he hadn’t seen her move. Yet she now held a puffy pink clothes hanger. Of course the hanger itself wasn’t the problem… rather it was what the hanger itself held. Josh stared with dismay at the pink and white item he had especially tried to avoid thinking about. The sinking feeling in his tummy told him that the moment he had dreaded most was now at hand.

Inside the world of his mind, putting on this particular garment would effectively shred what little remained of his “bad boy” act. Somewhat irrationally since he was already wearing panties, the flustered teen felt he was standing on a threshold. Until that moment, he somehow thought his normal life could be clawed back. His eyes darted feverishly around the girlish room, but he saw no escape. Worst of all, he had willingly agreed to this. But maybe there was still a way out…

Sensing a rise in his agitation and perhaps a last shadow of resistance, Gwendolyn delivered another nudge. “Remember Joshy, this is your decision. A big part of this will be learning to follow through on your commitments.“ She continued, “Otherwise… “ she let her voice trail off and cast a studied glance at the Sterncourt uniform still beckoning from the bed.

Increasingly caught in a trap of his own design, and knowing where the other path led, Josh’s spirits plummeted. The brief flicker of rebellion vanished, and his eyes dropped back to the floor. He again took painful note of his sissyish bralette and panties.

With a perfectly manicured index finger, Gwendolyn pushed Josh’s chin up until he was forced to study himself in the mirror. With her other hand, she held the hanger under his chin so that the girly garment was draped across the self-conscious teen’s body. “If this is to really work, you must make an honest effort,” she coaxed. “Take a good look honey, and tell me what you want,” she directed. Her words hung in the air for yet another interminable moment.

Josh peered at his reflection and paused.  Then, in a downcast tone of surrender, he said simply, “Ok.” It was all he felt he could muster.

“OK what?” she asked, a tad too impatiently. She cautioned herself that this was a critical moment. She took an almost imperceptible breath.

“Josh, you must be clear about what you are asking,” she continued. “I need to make absolutely sure I know what you want to choose.” The possibility of Sterncourt still lingered like a weight on his chest.

During Gwendolyn’s conversations with Karen, they had concluded Josh needed to choose his new life as much as possible. She felt her role was to “help” him reach the correct choices. As Karen had put it, “Maybe it’s like a casino. It’s quite all right if he has a small victory now and then, but in the end the house always wins!” They had both laughed, but that was the plan. Gwendolyn intended to rig this game so the final outcome was never in doubt. A simple “Ok” just would not do.

“Mom…” he started uncertainly before she interrupted him.

“I think ‘Mommy’ is more appropriate now. It will help you break your old habits,” she continued. Although this was phrased as a suggestion, her firm tone made clear what was expected. “And certainly a ‘please’ is always nice too.”

The dejected teen had not called his mother “Mommy” since he was a small child. The moment overwhelmed him and he exhaled with a shudder. Josh’s next words came with little conscious thought, almost as though the girly boy in the mirror was speaking on his own. In a timid voice, Josh stammered,  “Mo… Mo… Mommy, will you help me?” he asked, adding “please” as a hasty afterthought.

With a sweet and confident smile, Gwendolyn prodded her unsettled teenage son, “Will I help you what sweetie?  Please tell me what it is you want.”

Josh winced. It wasn’t enough that he was doomed to be turned into a sissy. He had to ask for it? Swallowing hard and thoroughly chastened as his cheeks glowed their brightest red yet, he quietly mumbled his next words. “Mommy, will you please help me put on the dress?”

“Nearly there,” his mother thought with glee. She pressed her agonized son again, “Whose dress is it, honey?”

It was finally clear to Josh what she wanted to hear, and he was ready to say nearly anything to get out of this moment. The teenage boy’s next words were music to Gwendolyn’s ears. She would treasure them for years to come:

“Mommy, will you please help me put on my dress?”

Smiling broadly, Gwendolyn replied “Of course, sweetie! You only had to ask!”

The red-faced teen’s knees weakened as blood rushed to his head. Butterflies flew wildly in his stomach and his little man perked up yet again. His emotions swirled.


Sissy Little Girl

  • Winner of the Golden Panties Award
  • **********
  • Posts: 338
  • Karma: +448/-9
Re: New Arrangements for Josh
« Reply #36 on: June 23, 2020, 08:53:42 PM »
sissyboy1212, I love it.  Josh will now become a girl and right now, he hates thinking about it.  Of course, he hates the thought of Sterncourt even more.  I have a feeling that mommy is going to really enjoy Josh's new life.  And now, he has to put on the dress.  Great job as usual.  Keep up the good work.


dolly bo peep

  • Ultimate Sissy
  • *********
  • Posts: 196
  • Karma: +559/-7
Re: New Arrangements for Josh
« Reply #37 on: June 24, 2020, 09:10:19 AM »
Sissyboy1212,

I'm enjoying your story's measured, methodical progression with your description of Josh's thoughts as each step happens.

I'm looking forward to the next steps.

sissyboy1212

  • Ultimate Sissy
  • *********
  • Posts: 193
  • Karma: +11473/-5
Re: New Arrangements for Josh
« Reply #38 on: June 25, 2020, 10:38:15 PM »
PART 11

The pink gingham dress stole Josh’s breath. Incredibly sissyish, it was something a little girl would be thrilled to wear. Removing the pink creation from the hanger, his mother went on, “This is a fun little spring/summer dress I just thought would be perfect for your first!” Josh noticed how happy she seemed. He wished desperately that the floor would open a hole for him to fall through, but it was not to be. “It’s perhaps a tad fancier than the average casual dress, but I wanted your first one to be extra special. It will still be fine for everyday wear,” she encouraged. Smiling broadly at him, she added, “Well let’s not waste any more time. Let’s put you in it!”

“This can’t be happening,” Josh fretted to himself. “I’m a fifteen-year old boy, and I’m letting myself get put into a dress!” Standing awkwardly in his bralette and panties, he waited gloomily as his mother carefully removed the gingham dress from the hanger. She excitedly held it open for him. Despondent, he tried to come to grips with the unreal course of events. With a sinking feeling he thought, “I’m going to be turned into a sissy… it’s actually going to happen.” Not only was he going to be sissified, but he had asked for this himself. Specifically and clearly. Although the other option had been awful, nothing could change the reality that he had made his own choice. That was the truth. He stared with dread at the dress which beckoned him.

Although fascinated by her son’s expressions, Gwendolyn was eager to proceed. Her thinking had rapidly come a long way. The hesitation and uncertainty she felt in that first conversation with Karen just days earlier had been replaced with a sense of purpose. She felt elation at the prospect of sissifying her son in order to save him. She nodded expectantly as she gestured for him to step into the garment. Resigned to his fate, the teenage boy took a slow, shaky breath. Then, Josh skittishly stepped into his dress.

Standing there red as a beet, he obeyed his mother’s instructions and slipped his arms into the short puffy sleeves while she pulled them up. The openings were elasticated, and they drew closely around even his slender arms. Josh normally wore old loose fitting tee shirts which hid his skinny build. With chagrin, he saw that the way these sleeves billowed up toward his shoulders would accentuate how delicate and girlish his arms were below.

With a buoyant smile, his mother dramatically whooshed the dress up over his chest and fitted it into place. She couldn’t help but giggle joyfully. Josh, on the other hand, felt his skin crawl. The breezy cotton material floated over his body before settling airily into place. He could feel his dress gliding smoothly against his bralette and panties as intense new sensations assailed him. The dress tickled as it seemed to dance across his legs and groin. He shivered as she began buttoning him up in back. While she methodically fastened the seemingly endless line of buttons, he unhappily realized it would be hard to remove his dress without help. With each button she closed, the dress hugged his slim torso closer and closer. When she finished the last one at the back of his neck, the crisp white collar brushed lightly against his throat just enough to remind him it was there.

Next, his mother first pulled and then cinched something around his waist. As she tied it taut, it belatedly dawned on him that there was a sash tie in back which made the bottom flare out. He deduced from the way she fussed meticulously with the knot that she was tying a bow at the small of his back. “Great,” he thought glumly. He peered down at his poofy skirt. The lacy edge of an attached white tulle petticoat peeked out prissily from under the pink gingham and rustled airily against his skin.

At last, Josh’s back bow was adjusted to Gwendolyn’s liking. Truth be told, she enjoyed this more than she cared to admit. The sight of her helpless son buttoned tightly and securely into his new frock enthralled her. “He won’t be getting out of that easily,” she thought with satisfaction. Observing his facial expressions, she realized he knew it too. She involuntarily licked her lips. To her, his worries and consternation were almost... delicious. She finally spoke again, intentionally compounding his discomfort. With a veneer of helpfulness, she explained, “This dress doesn’t really need the petticoat, but it does add some fun to the look.”

“Fun?” the miserable boy thought, “this is the exact opposite of fun!” But he was growing more docile now. Acceptance was already taking root in the corners of his mind. Although Josh’s conscious brain still loathed every aspect of his transformation, his subconscious was busily at work. Any lingering traces of resistance seemed to be disintegrating quickly. Each tiny movement he made caused his dress to crinkle and tingle across his skin with a cascading effect. His heart fluttered and his cheeks burned as feelings collided inside him:  Shame, anxiety, worry, excitement... arousal. What was happening to him?

In a daze, he blinked sheepishly. Meanwhile, Gwendolyn admired her handiwork with undisguised delight.

Sissy Little Girl

  • Winner of the Golden Panties Award
  • **********
  • Posts: 338
  • Karma: +448/-9
Re: New Arrangements for Josh
« Reply #39 on: June 25, 2020, 10:42:58 PM »
sissyboy1212, Josh has now been confronted and dressed in his very first dress.  The emotions running thru his head right now are totally opposite of his mom, Gwendolyn.  It looks like he is going to become a nice little girl.

Keep up the good work and hurry with the next chapter.  PLEASE......
 8) 8) 8) 8) 8) 8) 8) 8)

dolly bo peep

  • Ultimate Sissy
  • *********
  • Posts: 196
  • Karma: +559/-7
Re: New Arrangements for Josh
« Reply #40 on: June 26, 2020, 08:36:24 AM »
sissyboy1212,

Like Sissy Little Girl, I enjoyed your last chapter.

I like the pace of your writing, including the delicious details.

Will your next chapter continue with the transformation? What are the best hosiery and shoes to go with that cute gingham dress? Are pigtails and ribbons the obvious choice for his hair? What jewelry/accessories will mommy find appropriate? What input will sister Kathy have?

We are waiting eagerly for your next chapter.

sissyboy1212

  • Ultimate Sissy
  • *********
  • Posts: 193
  • Karma: +11473/-5
Re: New Arrangements for Josh
« Reply #41 on: June 26, 2020, 12:30:50 PM »
Thank you both for the sweet comments.  The next chapter is mostly written and you will definitely learn more about poor Josh’s transformation.  The details are my favorite parts of these stories, so I try to add them in. 

The trade off is that the plot moves slowly. Of course it’s a shame that this means Joshy’s discomfort just keeps getting dragged out, but it really can’t be helped. Tsk, Tsk. 

Besides, he’s not going anywhere!

And Kathy will make her reappearance soon. Some of her next part is already drafted too.

Hugs!


 

The more you give, the more I can give back.

The dots in the map below represent every person who visited Betty's since May 17, 2020. Blinking dots show people currently here. However if you haven't clicked on anything in a couple minutes your dot won't blink until you click on something again.

























Web
Analytics

Hits to Betty's Pubs since Sept. 30th, 2004

eXTReMe Tracker

Website, forum design, software, & security on this site is copyrighted. It was made personally by Betty Pearl, of Betty Pearl's Pubs, Sissy Stories, buffalobetties, pearlcorona. Betty's Pub is a non-profit organization & support group for the transgendered, & Fetware community. We don't sell anything, & we don't data mine your personal information & habits to sell like MOST other sites do. We respect your privacy & won't sell it out for a few bucks.

Site for: Sissy Stories, ABDL Stories, Sissy Art, Crossdressing, Transgender