Jack behaved himself surprisingly well once Jessie came down. He demurely followed his sister back to his nursery and they grabbed their dolls and brought them to the living room to sit on the floor and play with them.
“No, sit down like this.” Jessie instructed, sitting down gracefully. Jack tried, but it seemed as though he could not help but sit down in an unladylike fashion that flashed his diaper. “I swear, you just like showing off your diaper, don’t you?” She teased. “It’s mom’s fault for putting you in such pretty plastic panties.”
“Is that your way of telling us you need a change, Jack?”
“No.” Jack said, scandalized. He only just managed to keep his voice at a normal speaking volume, doing his best to remain cognizant of his mom’s instructions to him.
“Do you need to go?” His mom asked. “It’s been a while.”
“No, I’m good.” Jack muttered. His mom nodded.
“I don’t want you two getting dehydrated. I’m grabbing you both bottles of water and I expect them to be empty by dinnertime, which is in an hour.” She looked from Jessie to Jack and back again, the twins sharing near identical expressions. She grabbed three bottles of water, figuring she should follow her own advice and brought them into the living room. “Try not to spill on these beautiful floors.” She said.
“Thanks, mom.” Jessie said, taking hers. Jack, hearing his sister, realized what he would be expected to do. Trembling slightly as he rose to his feet, he dipped into a shallow curtsey, feeling quite foolish by doing so.
“Thank you for the water.” He wished he could disappear through the floor. Jessie looked as if it were Christmas and her birthday rolled into one.
“You could learn a thing or two about proper manners from your brother, Jessie.”
“Well, it’s how princesses act.” Jack stared at Jessie in confusion. “Do you mean you don’t feel like a princess in your pretty dress, Jackie?” He sat back down, taking care not to flash his diaper. He figured if he sat properly, Jessie would not press the point about his outfit. For once, he was right.
Jack was certain that he had never played with dolls, so he primarily followed Jessie’s example. She was more than happy to initiate her brother into the mysteries of dolls, telling him to hug his doll and pretend to listen to what his doll was telling him. He felt foolish, but after a while, he accepted the fact that no one would know about this other than his mom and his sister.
Jack could not say that he got used to the thick cotton between his legs and under him, nor was he used to the pink dress he noticed again every time he moved, but they stopped mattering for the moment. Once Jessie realized that Jack would not blush every time she mentioned his outfit, she stopped mentioning it quite so frequently, except to scold him every time he sat or moved in a fashion that exposed his diaper. Jack did not seem to realize, but both his mom and Jessie herself noticed that she had begun to talk to him more and more as if he was her little sister.
* * *
“I promise, Diane, it will work.” Denise said, pushing a lock of greying hair behind her ear. “It sounds crazy, but trust me. This is just what you’re looking for.” She knew that Diane saw her as a bit of a maternal figure, so she tried her best to always nudge her in the right direction. She knew this was what Diane, and Jack, needed. She just had to get Diane to see things her way. She could not tell her the full truth, not yet.
“I mean, doesn’t it seem a little drastic? A few of his friends have started pushing limits, but he still seems like a good boy.” She paused before adding “Well, other than the swearing.” In truth, she had only ever heard from other parents that he swore while over at his friends’ houses, but she was fairly certain he had only just barely avoided swearing in front of her on a few occasions. That was certainly a habit she wanted to nip in the bud.
“At the age your kids are at, they start forming identities outside the house.” Denise said, as if she knew just what Diane had been thinking. “Put simply, Jack is a different person with his friends than he is with you. You said his grades have been slipping, right?”
“They have.” She had grounded him for a weekend when she saw his report card.
“And he’s had some behavior issues with his teacher?”
“A few.” Denise nodded and sipped at her mug.
“You simply have to stop these things at the beginning. It’s hard to break habits once they form.” Diane fell silent for a moment. She just was not sure.
“It seems so drastic. He’s really a lot better than some of the boys his age.”
“I know. I raised a boy myself, you know. I know all too well that boys at that age are very sensitive to peer pressure. You told me he threw a fit about his friends teasing him about his underwear.” Denise chuckled good-naturedly. “They say girls care all about fashion, but boys are twice as worse, I swear.” Diane nodded and shrugged, but remained silent. “If they can get him to change his clothes, he’ll be putty in their hands when it comes to other things.”
“I know, I know. Jessie’s been able to get him to do anything she wants all their lives. It took years before people actually believed they were twins. Everyone assumes Jessie’s older.” Diane took a deep breath. “It’s worth a shot, I guess. If I get nervous, I can just let him go back to his old clothes, I guess.” Denise smiled and sipped her coffee.
“Trust me. This vacation will be life-changing.”
* * *
As Diane put the finishing touches on dinner, she peeked into the living room to see that the game had changed. The dolls lay forgotten on the floor for the moment as Jessie began to tutor Jack in sitting down on every conceivable surface in the living room in a ladylike fashion. The only thing that brought an end to Jessie’s impromptu finishing school was her declaration that dinner was ready.
Jack allowed his sister to go first, still feeling self-conscious about his waddle. He sat down across from Jessie at the table, in a much more polished fashion than before, and Diane shortly joined them with their meal: spaghetti and meatballs, one of Jack’s absolute favorites. He eagerly dug in.
“Don’t get any sauce on your dress, Jack. I think that’s dry clean only.” His mom cautioned. He slowed down, not wanting to find out what would happen if he did get the dress messy.
“We could find him a bib.” Jessie said. Jack tried to kick her in the shin, but missed, which was probably for the better.
“Enough, young lady. We’re on vacation, and for me, that means a vacation from listening to my kids fight all the time.” They all ate quietly until Diane spoke up again. “I was thinking that, after this, we can get into our pajamas and watch a movie or something.” She smiled. “Maybe even play a board game, but I’m not sure if that’ll help you two not fight.” Many a childhood board game had ended in shouting matches and worse, to the point where she had quietly asked relatives to stop buying Jack and Jessie board games for the time being. “So, movie it is?”
Once they finished eating, Diane leaned back and smiled at them. She held up a finger and went back and forth between Jack and Jessie. She landed on Jessie and nodded.
“Alright, Jessie, you clear the table and wash the dishes quick. Jack and I will go into his nursery to get him ready for movie night.”
“Nursery.” Jessie said with a cackle as she gathered the dishes.
“Mom!” She simply rolled her eyes.
“Jack, she’s just saying what it is. She’ll stop laughing eventually.” She stood up and tapped his arm. “C’mon, get up. Lollygag any more and I’ll make you thank your sister for clearing the table.” Jack jumped up and hurried out of the room as quickly as his diaper allowed him to.
“Am I gonna have to wear a dress to bed?” Jack asked, trying to find somewhere in the nursery that did not immediately remind him just how girly the room was.
“Oh, no, sweetie. Your dress is much too fancy to wear to bed.” His mom said teasingly. “Let’s get your dress off first.” Jack reminded silently obedient while she stripped him to his diaper. He glumly looked down at the pink plastic panties, wishing that those could be removed too. He missed his boxer briefs. What color had he had on that morning? Black? Red? His heart fluttered anxiously as he realized he could not quite remember.
“What’s wrong, honey?” His mom asked. She slipped a finger into his diaper. “Another accident, Jack?”
“No!”
“You’re damp. It must’ve been a small one, but your diaper doesn’t lie.” His mind raced. When had it happened? He swore he had been dry a moment ago! He felt like he was dry, but he did not want to check himself.
“There’s no way! Mom, I swear! I didn’t!”
“Jack, you’re wet. How do you explain that?” He stammered, but he did not have an answer. She sighed and shook her head to hide her amazement. She had not done anything to make him have so many accidents. The stress and confusion must be to blame, or perhaps just the convenience. Jack had remained in diapers a good eight months after Jessie, after all. The diuretic was only supposed to work for the car trip. “Come with me, Jack.” She took him by the hand and led the blushing boy out of the nursery.
“Where are we going, mom?” Jack asked, which only caused Jessie to look over her shoulder and burst out into laughter seeing her brother being led along in just his sissy diaper.
“We’re going to the bathroom. I suppose I haven’t shown you where that is yet.” Diane said. “Not that you’ve asked.” Jack looked up at her in confusion. She did not sound mad. It was difficult to gauge her emotion.
Once they were in the bathroom, she closed the door behind them and gestured toward the toilet.
“Here’s the deal. You’re going to do potty time, just like when you were little. You’ll have that time to do whatever you need to, okay?” He nodded bashfully. “We’ll probably give you another chance before bed, but just in case, I want you to try really, really hard.” She gently tousled his hair. “Good little boys use the potty, remember?” His head bobbed up and down again. “Alright, let’s get your diaper off.”
The naked boy blushed and covered himself, trying not to look at the diaper and plastic panties that his mom held in her hands. It felt strange to be standing there without the fat diaper between his legs. Did he miss it? No, of course not. It just felt weird.
“Are you going to stand there?” He asked in a tiny voice.
“Yes, that’s how potty time works.”
“Mom, c’mon.” Jack protested. “I can use the toilet. I just keep having accidents.”
“Prove it then.” She said.
“Leave and I will.” He insisted.
“I’m not leaving you unattended for the rest of the evening.”
“Turn your back then.” He gestured turning around, but quickly returned his waving hand to its place with its twin over his privates.
“If you’re concerned about me seeing something, sit down. It’ll probably be easier anyway.” She stood there, silently staring him down. It took him a moment, but he relented and sat down on the toilet. “Ten minutes.” She looked at her watch. The time seemed to creak by, the bathroom dead silent. She considered saying the ten minutes were up, watching her son sit there as still as a Rodinesque statue. Just as she felt ready to speak, she heard the unmistakable sound of him going. She celebrated it by simply nodding to him and then watched the last two and a half minutes fly by.
“Alright, let’s go back to your nursery.” She said, her mellow voice seeming like a shout in the silent bathroom. Jack’s hands went back over his privates and she led him out of the room, leaving him no chance to dash back to the safety of the nursery. He followed meekly behind her.
To his horror, Jessie was still downstairs washing the dishes as his mom led him back through the kitchen. She snickered even more to see her brother now completely nude, his bottom still showing signs of his earlier spanking. He made sure his hands were covering everything down below.
“Jessie, how are you not done with those dishes yet?” Diane sighed and came over to the sink. “Jack, stay there for a minute while I help your sister finish these.”
“Can’t I go in my room?”
“It’ll be just a minute and I want to keep an eye on you. Quit your fidgeting.” With her mom right there, Jessie could do little more but steal quick glances at her humiliated brother. She had always thought of him as her little brother and it was hard to argue that he was anything else than that, standing there in the most vulnerable position possible. He retreated behind the cover of the table, but kept his hands right where they were, just to be safe.
With the two of them working together, they had the dishes washed and dried in just about a minute. With a glance giving him permission, Diane followed the scampering Jack into the nursery.
“Go get ready for movie night, Jessie.” She called over her shoulder. “Jack, hop on your changing table.” Jack complied and Diane came over to him, but she left the strap off of his chest.
“Do I have to?” He asked as she gathered diapers for him.
“Yes. But,” She smiled at him and rubbed his thigh reassuringly. “Since you’ve behaved this evening,” She paused and studied his excited expression before continuing. “I thought I’d give you a reward. You can wear your own pajamas tonight.” He tried to look thrilled, but he had not been looking forward to wearing the pajamas before this all began. He had last worn pajamas to bed when he had been seven or eight, foregoing them to sleep in just his underwear since. The pajamas that his mom had bought him for this vacation looked like they belonged to a seven or eight year old, light blue with smiling clown fish on them. All the same, however, they had to be better than whatever girly pajamas he would end up in if he complained. The very thought of that made him shudder. He had no way of knowing how long it would take before his mom let him get out of diapers, but he could at least avoid the dresses and stuff where he could, right?
Jack was so distracted by his thoughts that he did not notice his mom adding an extra two diapers to the stack before pinning them around his waist. “Let’s see, do any of your plastic panties seem like they’ll go with boy jammies?” His mom said, more to herself than to the blushing boy. “These will do.” She said, holding up a powder blue pair with only a few white bows around the waist. Jack could not help but wonder where she had hidden them, given the frilliness of the pairs he had worn throughout the day.
Once she had pulled the pajama pants over his slender legs, she had to fight to keep herself from giggling at how obvious his diaper was under the pants. She almost wished she had gotten him a set with shorts, but what was done was done. Due to the fat diaper underneath them, the legs of his pajama pants fell only to about mid-shin, resembling capris more than proper pants. She stifled a giggle.
“They’ll work.” She said, noticing the boy’s distraught expression. “Unless you’d prefer to see what your nursery has for nightwear?” He quickly shook his head, remembering the nightgowns that Jessie had worn when they were younger and figuring that what his mom would find in the nursery would be far more girly and embarrassing to wear.
Betty Pearl's Sissy Stories 20.1
Topic: Secluded Cabin Sissy (Read 75219 times)
