Jack sat in the hastily constructed playpen, arms crossed and glowering. He could hear Jessie and the neighbor boy Kyle running around outside, as well as the adults chatting in the kitchen, but he was stuck in the living room in a playpen. At least Caitlyn was leaving him alone for the moment.
His mom kept glancing over at him, but he wished that she would not. Every glance only seemed to remind him that he wore a bright yellow dress that did nothing to conceal his diaper underneath. Even when he had been standing, it had only come level with the bottom of his plastic panties. On his feet, he wore a pair of white socks with lace frills around the ankles to match the lace on both his plastic panties and his dress. Atop his head, the only thing that kept their guests from realizing his true gender, was a frilly bonnet like something out of an old cartoon. He sighed into the bulb of the increasingly ever-present pacifier, hoping against hope that this would all be worth it.
* * *
“Why can’t I wear my normal clothes?” Jack asked, irritated. “This is getting ridiculous!”
“Put that pacifier back in your mouth, young man, and I’ll explain.” Diane said, setting his nightgown aside. He groaned, but obeyed. “Given that you wet yourself already this morning, you’ll be in diapers for the duration of the neighbors’ visit.” His eyes seemed to shoot daggers, quite at odds with the brightly colored pacifier he was practically chewing on in his annoyance and frustration. “But, if you behave, and cooperate, I’ll reward you with your regular clothes again.” She could tell that he was interested. “But it does mean going along with diapers and what I have you wear for the entire time the neighbors are here. Understand?” He nodded a bit glumly.
“Can I at least go to the bathroom before you put another” he sighed. “Diaper on me?” She considered this request.
“Alright.” She said, silently grateful to delay the real bombshell, if only for a moment. She knew he would throw a fit, but she remained confident that she would be able to keep him in line with the promise of a reward. She stripped him down and gestured toward the door. “Jessie’s still upstairs, so hurry if you don’t want her to see you.” Jack did not need to be told twice, dashing out toward the bathroom.
While he was away, Diane busied herself gathering the outfit she would put him in. If it was all assembled, it saved time and gave him less of an opportunity to either protest or run away.
Looking over her handiwork laid out on the mattress of the crib, she realized she was missing just one thing: her son. What was taking Jack so long? Checking her watch, it had been at least ten minutes since she had allowed him to go to the bathroom. Sighing, she headed to find him.
“Jack? Everything okay in there?” She asked, knocking on the door.
“Yeah.” She tried the knob, but it was locked.
“Well, what’s taking so long?”
“Nothing.” He said nervously. “I’m just staying in here.”
“You’re what?”
“I’ll just hide in here. It’s better than wearing diapers!”
“Jack”
“Go away. I’m not coming out! Ever!” She could not help but roll her eyes at his
histrionics.
“You're being ridiculous, Jack. You can't stay in the bathroom all day.” She said. “What happens when you get hungry?”
“I” his voice trailed off. “I’ll come out once the neighbors leave.”
“You’re not getting your clothes back with this attitude, mister.” She said sternly, knocking on the door again. “Open this door before I count to five or else.”
“No! I’ll come out if you promise I won’t have to wear diapers! Why can’t I wear my regular clothes?”
“It’s your punishment, Jack.” She said. “It’ll all be over this afternoon, if you cooperate. I promise.”
“You do?”
“Yes, Jack. Now open this door.” Jack stood within the bathroom, debating. His mom had gone back on her word how many times? Could he risk the chance to finally get his normal clothes back? “Jack?”
“I’m thinking.”
“This is a limited time offer, Jack. The neighbors will be here in less than half an hour.”
“Just give me a minute.”
“You have one minute, Jack. Take any longer and I’ll call Jessie down to try and get you out of there. I doubt you want that.” He and she both knew that that was the case and she hoped that that would motivate him to give in.
The boy emerged from the bathroom with a sigh, walking back toward the nursery with the air of a death row inmate. She followed behind him, conscious that he might try to run again once he saw the outfit she had laid out for him.
“So dour.” She mused as he climbed onto the changing table. “Let’s start with your diaper.” He glowered up at the ceiling as she ran the strap across his chest. “We won’t make it as thick as the overnight one.” She reassured him, patting his arm as she stacked three diapers together. “Raise your bottom for me please.” He did not show it, but Jack did appreciate that she was at least somewhat granting him autonomy today, even if she was diapering him all the same. “Would you prefer yellow or pink?” She asked. The outfit she had set on the mattress of the crib made it clear which color she suspected that he would pick, but she still wanted to at least give him the semblance of a choice.
“Yellow.” He said, his voice monotone.
“Ask nicely.” She reminded him. He nodded before silently debating about how childishly to ask. He figured he should try to overdo it rather than under.
“May I please wear yellow, mommy?”
“I know you don’t mean to sound so sincere,” she said as she pulled a pair of yellow plastic panties up over his fat diaper. “But it’s so nice to hear you talking politely.” She smiled down at him. “Maybe I should make it a rule that you have to call me ‘mommy’ for the rest of the vacation, even once you’re back in your big boy clothes.” She could tell that her idea was not going over well with the boy, so she moved on. “Now, Jack. I spent a lot of time this morning trying to figure out how we can handle your punishment with the neighbors here. Before you argue, I did consider just allowing you to wear your normal clothes, but your little temper tantrum in the bathroom has convinced me that I was right to decide against that.” She looked at his crestfallen expression, nodding to herself. If nothing else, at least he would learn that his actions have consequences. “Of course, it’s possible that the neighbors might be a bit puzzled by a boy in a dress and diaper.” Jack bit back a snarky response and simply nodded. “So, and this is the tough part, I decided that we’ll just have to try and make you look as much like a little girl as possible.” His reaction was immediate.
“What? No way! No way, mom!” He yelled, trying to get off of the changing table. From his reclining position, he was unable to release the restraining strap. She waited for him to calm down, knowing that there was little he could actually do at the moment.
“Jack, I’m sorry, but it’s all I could think of.” She said as he finally settled.
“But mom”
“I know, Jack, I know. But the options are: we present you as a boy in a dress and diaper or as a little girl. You’re still small enough that we could, with the right outfit, pass you off as younger than you really are. You might be surprised.”
“But” She cut him off again.
“I’ve given it a lot of thought as to how we’ll hide the fact that you’re a boy. They’ll only be here for a few hours, so you won’t need your diaper changed. You’ll have a pacifier, so you won’t have to speak. We’ll use a bonnet to hide your short hair.” She smiled mischievously as she reached the last point. “And no one would ever think a boy would be caught dead in the dress you’ll be wearing, especially a teenage boy.”
“That’s not helping.” Jack muttered.
“C’mon, Jack. I promise you that if you go along with this, you can change into your regular clothes the moment they leave. Okay?”
“You absolutely promise?”
“Yes, Jack.” He sighed and nodded firmly.
“I’ll do it.”
* * *
Standing in front of the mirror, Jack tried in vain to tug the dress down even a millimeter farther, but it would not budge. He gnawed on the bulb of the pacifier in annoyance, the frills of the bonnet bouncing with the slightest motion of his head.
“It’s too late to turn back now.” Diane said, once again seeming to read his mind. She admired her handiwork, but then an ear-splitting squeal cut the air. They both turned around to see Jessie in the doorway.
“He’s so precious!” She gushed. Jack stood there, red in the face as his mom explained the plan to Jessie. He rolled his eyes every time she referred to it as ‘our plan’ as if Jack’s opinion had been asked at all as she made it.
“Enjoy it while it lasts, honey.” Diane said. “He’s only wearing this until around lunchtime.” Jessie looked disappointed, but Jack had become nearly inured to her teasing. “Can you go set up the playpen in the living room? I brought it in from the garage while you two were still lazing around in bed.” Jessie left to set it up as Diane busied herself putting the finishing touches on her son’s frilly outfit. “The worst of it’s behind you now, Jack.”
“Assuming Jessie keeps it secret.” He muttered.
“She will.” Diane reassured him. “I think she knows I’ve gotten creative with my punishments, hmm?” She smiled and kissed the pouting the boy’s cheek. “I love you, Jack. Don’t forget that.”
“Mom, we’re all set.” Jessie called from the living room.
“Alright, Jack. Let’s go get you set up.”
“What about breakfast?”
“I’ll bring you something once you’re situated, okay?” She said. “One of those breakfast bars you love so much.”
“Apple cinnamon?”
“Of course.” She nudged him toward the door. “Oh, and just so you’re not shocked, I’m going to have to introduce you to the neighbors as my daughter or little girl or something. We’ll just call you Jackie, okay?” He grunted a non-committal response. Only a few hours separated him from his own clothes and freedom from this bizarre nightmare.
Betty Pearl's Sissy Stories 20.1
Topic: Secluded Cabin Sissy (Read 77094 times)
