First of all, let me just thank each and every one of you for the very kind and sweet comments. I can tell a lot of you are excited to see what comes next for Jack and his family, so I hope I can keep you all engrossed by this story even as the upcoming holidays fill our schedules with things outside of this story and website. A lot of you suggest/hope for things that are going to come over the course of this story, so I hope you indulge me even if those things don't come quite yet in part 4. So, without further ado, part 4 is right below! :)
* * *
As Jack approached the stairs, he had to pause for a moment. This cabin seemed remarkably up-to-date, but could he trust the stairs not to creak and give his sneaking away? He could hear Jessie and his mom had moved on to discussing other things, but time was against him. If he could simply get upstairs and change back into his clothes, surely everything would go back to normal. He cautiously took a step, his bare foot feeling every strand of the dark green carpet on the stairs. He carefully put his weight on it, breathing a sigh of relief. He quickly dashed up the stairs, silently resolving to make sure Jessie never went up them behind him. She would get quite the show. He quickly dismissed the thought. He would not be in a dress after today and definitely not in diapers.
Going down the stairs that morning had seemed difficult with the diaper, but ascending these stairs proved to be a challenge as well. The fact that he could not see his feet due to the dress made things even more difficult than he had expected. When he finally got to the top, he wondered just how long he had before his mom and sister discovered his absence. He looked to the left and the right, trying to determine which direction lay the room he was supposed to share with his sister. That was where Jessie had put his clothes, right? He waddled to the left, spying bunk beds through the slightly ajar door. He pushed it open, wincing as the door squeaked slightly. Had anyone heard downstairs? It did not matter. He saw his suitcase right there on the floor! He rushed toward it, having to grab one of the bedposts to steady himself.
“Jacob Anthony! Get your butt down here immediately!” His mom’s voice cut him to the core. What was he going to do? He morosely walked toward the stairs and descended. Try as he might to push the dress down, he knew that both his mom and Jessie got a very good view of his pink panties and diaper. To his horror, they both remained silent as he reached the ground floor. His mom lifted his dress and checked his diaper. He knew enough not to resist. “Diaper’s dry. What were you doing up there?” Before he could think up a lie, she added “and tell the truth or it’ll be even worse for you.” He gulped.
“I was going to put my clothes back on.” He said.
“These are your clothes, Jack. You’ve had trouble staying dry all day.” She looked at him and sighed. “I’m just disappointed, Jack. I have half a mind to keep you like this the whole time we’re here. Do you want that?”
“No!”
“Then you need to start listening to me, mister.” She said. “Jessie, quit giggling and go upstairs.” Jessie sighed and stomped upstairs. “And do not touch your brother’s clothes.” She looked at the boy in front of her. “Look, we need to figure out some way to get you to take this seriously.” She turned. “Come with me into the living room.” Jack did so, nervous about what his mom was thinking right now.
“Mom?”
“First things first, I think it’s time for that spanking.” She said, sitting and patting her lap. Jack knew enough to lie across it without arguing. “Might be a little tough, but let’s try this.” She pulled his pink plastic panties down to his ankles before unpinning the diaper and pulling back the part over his bottom. “Thank you for cooperating, Jack.” She gently rubbed his lower back. “How many spanks do you think you need to learn to always cooperate?” Jack was no stranger to this game. Jessie had no longer gotten spankings after they turned six, but Jack had kept getting them a few years beyond that, much to Jessie’s delight and his chagrin. He did not want to say too high a number because his mom would always give him at least as many as he said, but if he went too low, his mom could double it at her own discretion. It struck him as a situation that he would lose, no matter what.
He still remembered what might have been the last spanking he received. It had been at his and Jessie’s tenth birthday party. He had complained a bit too loudly about Jessie getting more presents than him and his mom had had enough. Before he knew it, he was over her lap with his jeans around his ankles, all of their guests watching as he received a spanking across the seat of his pristinely white briefs. As if the spanking was not bad enough, his friends had teased him about his ‘tighty whities’ for the next month.
“Well, how many?” His mom pulled him out of his thoughts. She gave his bottom a practice smack to help him decide.
“Ten?” His mom considered it for a moment and he wondered if he had gone too low. “Uh, maybe fifteen.”
“Fifteen sounds good.” She said. “Can you keep count for me? It’d be a good way to show me that you’re ready to be a good little boy.”
“Little boy?” He whispered in disbelief.
“Yep.” His mom said. He had not meant for her to hear him. “You’re lying across my lap for a spanking with your diaper tugged down. Seems like prime little boy to me, right?” He just nodded, keeping his thoughts to himself about how he did not look like any sort of boy at the moment. “Are you going to keep count for me?”
“Yes, I will.” He said, staring down at the hardwood floor. She raised her hand into the air and let it hang there. The anticipation was half of the point of the spanking, after all, and she could see him start to squirm as he wanted it to be over with. “We’ll have you back in your diapers soon, sweetie.” With that, she began to spank him.
“One, two, three” he counted through gritted teeth, trying to will the tears to stay down. His mom kept a deliberate pace, pausing just long enough between the strikes to hear him count and give him a chance to recover. “Six. Seven. Eight.” He tried his hardest to hold down the tears, but a few began to sneak down his cheeks. He was halfway through, he just had to make it through.
* * *
“You’re such a good little boy.” She praised, gently rubbing his lower back. Now that the spanking was over, she made it a point to soothe him as much as she could. His bottom seemed so red that she worried that she had overdone it, but even as she watched, it began to fade. “Look how calm and demure you are. I guess we should bring back bare bottom spankings even after this is over, hmm?” She brushed a tear from his cheek, but Jack remained silent and stared down at the carpet. If there was anything today had taught him, it was that his mom would do whatever she decided, regardless of what he said. “I’m sorry that I had to do that, Jack.” She said softly, pulling the diaper back up and repinning it. “I just need you to cooperate. I know this is a little weird, but it’s for your own good.”
“I don’t need diapers.” He mumbled.
“I know, but you’ve been wetting all day, right?”
“I guess.”
“How many pairs of underwear did you bring?”
“I dunno. Six?” She smiled, tugging his plastic panties back up and having him stand. She looked him in the eye, brushing away one last tear from his cheek.
“You’ve had three wet diapers today, so that’d knock you down to three pairs of underwear and it’s only day one. What would your plan have been?” He shrugged. As far as he could remember, it was only two wet diapers, but that did not sound much better. “So, maybe mom does know best, hmm?” He did not know what to say. “Maybe you should thank me for this?” Her tone made it sound like she was teasing, but she looked at him expectantly all the same.
“Thanks.”
“For what?”
“For” his voice seemed to vanish. He cleared his throat and tried again. “Thanks for this?”
“And what is this?”
“I don’t want to say.”
“Jack.” She said. “You just got a spanking for being a naughty little boy. Do you really want another one?”
“No.”
“Alright, then you’d better cooperate. I want you to say ‘thank you for putting me in diapers today’.”
“But”
“Keep arguing and you’ll get another spanking.” She said. “Just say it, Jack. It’s only” she counted on her fingers quickly. “Eight words. I know you can say eight words.” He stared down at the floor.
“Thank you for putting me in diapers today.” He whispered.
“Say it like you mean it, Jack.”
“Thank you for putting me in diapers today!” He proved unable to keep the annoyance out of his voice.
“I’ll just keep making you say it until I’m satisfied, you know.”
“Thank you for putting me in diapers today.” He said. She nodded.
“There. Was that so hard?” He did not answer. “Honestly, I think Jessie had a good idea earlier.”
“What’s that?” He asked apprehensively.
“Jessie thought you should curtsey.” His eyes widened.
“No way!”
“Yes, way. Think of it as more incentive to get out of your dresses.”
“They’re not my dresses!” He yelled. His mom shook her head disapprovingly. Grabbing his wrist, she pulled him back onto her lap.
“Listen very carefully. First of all, they are your dresses. I know you don’t understand why you’re wearing them, but the fact of the matter is, you are, so they are yours. Understand?”
“Yes.” He whimpered.
“Then repeat what I said.” She smacked his amply diapered bottom.
“They’re my dresses.”
“Why?”
“I’m wearing them, so they’re mine.” He said through gritted teeth.
“Secondly, I am sick and tired of you shouting. If you don’t stop yelling about every little thing, I will find a way to get you to stop. Do I make myself clear?”
“Yes. No shouting.” She stood him back up, but kept him close, looking her son over and adjusting his dress.
“Alright. Now, like your sister suggested, you’re going to curtsey whenever you thank her or me for something.”
“But I’ll” He quickly stopped himself from shouting. “I’ll look like some sissy.”
“Have you looked at yourself in the mirror, Jack?” She asked with a giggle a bit too similar to Jessie’s. “Honestly, you’ve been a sissy since you waddled out of your bedroom this morning.” She could tell that this upset him, so she hugged him. “But I know you’re not really a sissy. Once you’re out of these diapers, you’ll go back to being the little boy I know you actually are.” He hugged her back. Even if she insisted on calling him a little boy, at least that sounded better than being a sissy, didn’t it? “So, you understand that you’re expected to curtsey whenever you thank me or Jessie?” He nodded. She smiled and hugged him again. “Ready for your sister to come back down?”
“I guess.”
“She’ll be so surprised by your new curtseying habit. Go call her. Nicely.” She watched with a smile as her son waddled over to the stairs as if he were going to some terrible fate.
Betty Pearl's Sissy Stories 20.1
Topic: Secluded Cabin Sissy (Read 75222 times)
