The moment that they walked into the house, Diane began to think about Jack’s new role in the family. He stood there in the kitchen, wishing more than anything that he could go upstairs and put his clothes back on.
“Jack, would you prefer to sleep in the nursery or upstairs with Jessie?” Jack shrugged. Neither option sounded any better than the other.
“Is Jack going back to nighties?” Jessie asked.
“I think so. We’ll save his jammies for the inevitable sleepover with Caitlyn.” Jack’s eyes widened. As soon as his mom said it, he knew that it was bound to happen. “Unless you’d prefer to wear a nightie?”
“I bet Caitlyn would want him to.” Jessie giggled. “I think she has a crush on you, Jack!”
“She does not!” Jack protested.
“It’s true, Jessie.” Diane said, trying to remain diplomatic before adding “she seems to think of Jack as a girl her age.”
“Well, it doesn’t help that you make me wear girl clothes!” Jack grumbled. His mom looked at him.
“You get yourself into them with your behavior.” She replied simply. “Now. Go take a quick shower and then meet me in the nursery so you can get your diaper and nightie on.”
“I thought little girls take baths.” Jessie teased. Jack glared at her, not wanting his mom to get any ideas.
“Keep that up, Jessie, and you’ll be joining Jack in a diaper and nightie.” Diane said sternly. “Quit dilly-dallying, Jack.”
Jack felt a great relief in removing the swimsuit at last, even though he figured he would have to wear it again tomorrow. He got into the shower and relaxed under the warmth. In here, even if nowhere else, he felt like himself. How long were they staying at the cabin again? Three weeks had seemed like such a short period of time before they had left, but the last couple days had had so much confusion in them that he shuddered to think how he would be dressed on the ride home.
“I’ll wear my normal clothes.” He said, but the words sounded hollow. He knew that there was a good chance that he would be diapered, if not more, on the ride home. His mom had said he would wear girl clothes for the rest of their vacation, hadn’t she? It had been something like that.
He contemplated staying in the shower for a long time, but knew that his mom or Jessie would have no qualms about walking in on him in the shower. He could not even count the number of times at home where Jessie had something to tell him and just followed him into his room after his shower, telling him all about whatever while he stood there in just a towel. They had seen each other naked quite a few times as kids, but now that they were growing up, he felt like he valued Jessie’s privacy a great deal more than she valued his. Why had they begged for their own rooms if Jessie thought she could barge into his room whenever?
He chuckled to himself as he dried off. Of all the things to be concerned with right now, that was what came to mind? He listened to make sure that no one was coming and then stood in front of the mirror for a moment, towel in one hand, inspecting his body. He looked the same, his face still as boyish as ever. He wished he looked more like Kyle, who looked like he was already well on the way to becoming a man while Jack still looked like a little boy. He did a spin in front of the mirror, vainly inspecting all angles of his body. Realizing he was pressing his luck, he wrapped the towel around his waist, determined to avoid another madcap dash through the cabin completely nude.
“Should probably pee first.” He reminded himself.
* * *
“Jacob Anthony Carter reporting for duty!” He said with a salute. His mom looked at him, bemused.
“Well, I guess that shower did you a world of good.” She said. “Climb on up. I’ve got your diaper all set for you.” He sighed, but obeyed. “It’s not so bad. I promise I’ll take it off you first thing tomorrow morning. It’s just a precaution.”
“I know.”
“And remember, you get to wear your normal underwear.”
“Under a dress.”
“I agree that it’ll look weird, but we’ll practice moving around so that you don’t flash anyone, okay?”
“Not really what I meant.” Jack mumbled as his mom pinned the diaper around his waist.
“And what plastic panties would you like over your diaper?” She could see him bristle. “Even if your diapers are just a precaution, I’m not putting Mommy’s little girl to bed without plastic panties over her diaper.” She emphasized the female pronoun. “Does Mommy’s little girl want Mommy to pick?”
“No” Jack stammered. “What are my options, uh, mommy?” He had mostly forgotten about the whole ‘mommy’s good little girl’ ordeal after his most recent spanking, but his mom clearly had not.
“I think pink like your swimsuit.” She said with a smile. “Let’s see what we have.” Before Jack knew it, she had found three different pink pairs of rhumba style plastic panties.
“So my options” he said, trying to regain control of his voice. “Are white lace, pink lace, or both.” He shrugged. “White.”
“Sounds good to me.”
“Hey, mommy?” He said as she slid them up his legs. “We both know I’m trying to be” he paused to summon up strength. “Trying to be your good little girl, but could we maybe not mention that in front of Jessie?” Diane pretended as if she had to think about it, but smiled.
“Of course, Jack. Your secret’s safe with me.” She gently patted his thigh. “Now, let’s get a nightie on you before Jessie comes to find out what’s taking so long.” Jack could not help but notice that she did not ask him which nightgown he wanted to wear, instead pulling out a yellow one and pulling it over his head as soon as he sat up. When he thought about it, it occurred to him that he could have ended up in a lot worse than a fairly plain yellow nightgown, so he did not complain, at least outwardly. “Alright, let’s go find Jessie.”
“Am I going to sleep in here?”
“You can sleep upstairs with Jessie. It’s up to you.” Jack looked at her hesitantly. Did she really mean it or was it just a joke of some sort?
“If I slept in here, would the bars of the” he gestured toward the crib. “The bed be up?”
“I don’t think so.” Diane replied with a smile. “Thinking about sleeping in here?”
“Just worried what Jessie’ll say.”
“She’s been teasing you a lot lately.” Jack nodded. “Maybe it’s time we rein her in a bit.” Jack felt a spring of hope grow inside him. Was his mom finally taking his side?
Jack followed her out of the nursery and they soon found Jessie sitting in the living room, channel surfing. She grinned as she saw Jack in a nightgown.
“Oh, how cute!”
“I’m glad you think so, Jessie.” Diane said with a grin, winking at Jack. “There’s a matching one in the nursery with your name on it.”
“What?”
“I’ve always wanted to be one of those moms who dresses her twins identically. I mean, I got to a little bit when you two were babies, but not once you two starting growing up.”
“It looks cute on Jack. I don’t think I could, uh, pull it off.” Much to Jessie’s relief, her mom seemed to accept that.
“Well, Jack, thank your sister.”
“Thanks.” Jack said, giving a shallow curtsey. “She does seem jealous of my outfit.” He said. “Um, mommy.” He quickly added, eager to remain on his mom’s good side now that she was starting to turn the tables on Jessie.
“Does she?” Diane asked. “Don’t you start tormenting your sister, Jack. Let’s try again to have a peaceful family evening.”
“You’re not waddling that much. Did mom not diaper you?” Jessie whispered to Jack, who immediately regretted sitting next to her.
“She did.” Jack said, feeling Jessie eyeing his midsection for any clues.
“Good.”
“You two better be behaving.” Diane said.
“We are.” They said in unison. She looked at them both.
“Well, should we watch a movie or play a game?”
“Movie.” Jack said at once.
“How about I pick?” Diane suggested. She chose
The Princess and the Frog, which she knew they both liked, and they all settled in to watch it.
By the end of the movie, both Jack and Jessie were stifling yawns, unable to fool their mom into thinking they were not ready for bed yet.
“Off to bed, you two.”
“Are you sleeping upstairs with me?” Jessie asked. Jack saw his mom looking at him with the same amount of curiosity that Jessie was. He knew he had to make a decision.
“I think I’ll sleep downstairs, but maybe tomorrow I’ll go upstairs.” Jessie giggled at his response, but then shrugged.
“Whatever. Good night.” Jack watched, perplexed, as she went upstairs without so much as a second glance.
“Alright then.” Diane said, for once every bit as puzzled as Jack was.
“Good night, mommy.” Jack said, realizing only afterward that he had not needed to remind himself to call her mommy. WAs he slipping into the habit that quickly?
* * *
The next morning, Jack lay in the crib. He had forgotten at first that he would be allowed to wear his normal underwear today. Now that he did remember, he stared up at the ceiling beyond the mobile overhead, wondering if he could get up and take off the diaper he wore himself or if he had to wait for his mom to come assist him.
He could not help but wonder what his friends were up to at summer camp. They were probably having a lot more fun with their summer than he was. How would he even explain this to them? He could just shrug and say that he did not do anything, but how could he ensure that Jessie did not tell her friends, thereby allowing word to spread about his sissy summer? Even if his mom swore her to secrecy, she would find some way for word to get out; that much he was positive about. Could he beat her to the punch somehow? His stomach twisted at the mere thought of it.
“Good morning!” His mom said, breaking him out of his thoughts. “How did you sleep?”
“Okay.” He mumbled.
“Is your diaper dry?” To his relief, she made no move to check him, taking him at his word.
“Yeah.”
“Bet you’re eager to put your undies on.”
“Yeah.” He could not help but smile as, as if to prove that she was genuinely intending to let him wear them, she held up a pair of black boxer briefs. Things seemed to be going better now, but then he remembered that he still had to wear a dress over his underwear.
“Something wrong?” Jack did not answer, knowing that she knew exactly what had occurred to him just then. “It’ll be okay, let’s get your diaper off, okay?” He meekly nodded. He helpfully lifted his nightgown to make it easier for his mom to remove his diaper. He then dropped it long enough to pull his underwear on before yanking the nightgown over his head.
“How’s this going to work?”
“Go pick out your dress.” His mom said. “I’ll leave you alone so it’s really your choice.” She smiled and gently hugged him. “But, if you haven’t made a decision by the time I get back, I’ll have to help you, won’t I?” He understood and walked over to the closet to start looking at the options.
He first looked over the blue dresses, figuring that they were the closest to “boy” clothes, even if they were still little girl dresses. The plainest dress was a yellow sundress and he took it off the hanger. Should he put it on? He glanced to the door. He did not see his mom, but he had no way to know how much time he still had before she came back, so he resolved to put the dress on.
He walked over to the mirror and looked at himself, shrugging. He did not mind the way the dress looked, but he did not really know what to look for or how it was supposed to look. He turned slightly, inspecting it. It fell to his knee, so he did not risk flashing anyone.
“Still look like a boy in a dress.” He mumbled to himself. He felt strange about that. Did he want to look like a girl? He did not think so, but maybe that would at least make him look less awkward.
Diane headed back toward the nursery, but stopped in the doorway, surprised by what she saw within. Not only was Jack wearing a dress, but he stood in front of the mirror, swaying slowly back and forth with a shy little smile on his face.
Betty Pearl's Sissy Stories 20.1
Topic: Secluded Cabin Sissy (Read 77022 times)
