I'm so overjoyed by the response to this story and I hope that the arrival of the neighbors is everything all of my wonderful readers hoped it would be. Enjoy!
It was strange for Jack to watch from the playpen as his mom and Jessie greeted the neighbors. There were three of them, and his mom had already struck up a conversation with the dad, Michael. Jack, however, only had eyes for Kyle, who was roughly about his age and dressed in a much more appropriate outfit, black knee-length shorts and a very familiar looking red t-shirt. Kyle was a fan of Flight of Dogs too! Jack knew it sounded silly, but he felt as though his mom had known that and had intentionally prolonged his punishment just for this.
Behind Kyle stood a girl of about six, Caitlyn. She peered around her older brother, stealing glances at Jack. In fact, she was the only one who seemed to have acknowledged his presence.
“This is my daughter, Jessie.” Diane said, patting Jessie on the shoulder. She smiled and murmured a greeting to the three neighbors. “And I see Caitlyn has already noticed my little girl.” Even with the warning, Jack winced. “That’s Jackie. She’ll be staying in her playpen.” Kyle barely even looked at Jack, which Jack was grateful for. It made sense to him that a boy his age would have little interest in something as frilly and feminine as Jack must appear.
“Hi! My name’s Caitlyn! I’m six!” Caitlyn said, staring at Jack with far more interest than her brother had. Her blonde hair was in braids and Jack could not help but feel like her Barbie t-shirt and white shorts were vastly preferable to his current outfit. He could almost feel her gaze as she looked at his diaper before spinning around. “Daddy? Miss Diane? Can I help change Jackie’s diaper?”
“Changing a real baby’s a little different than your dolls, Caitlyn.” Michael said. “Why don’t you go outside and play with Kyle and Jessie?”
“Okay!” Caitlyn skipped away, leaving Jack in peace. Michael smiled at Jack before sitting down at the kitchen table with Diane. They settled into grown-up talk and Jack wondered just what he was supposed to do, cooped up in a playpen all morning. Jessie had set the doll he had played with the night before in the playpen, so he picked her up but quickly put her back down. Maybe his mom could turn the TV on for him? He looked over at her sitting in the next room, but how would he get her attention?
Noticing the remote not that far from the playpen, he resolved to get it himself. After all, he was not actually a little kid, no matter how his mom was treating him. Slowly getting to his feet, he waddled across the playpen and, stretching out his arm, just barely brushed the remote, knocking it to the floor and out of his reach. His curse was too muffled by the pacifier for anyone to hear, thankfully.
“What are you up to?” His mom asked, hurrying over. “I leave you alone for five minutes and you get up to all sorts of mischief, don’t you?” Reaching over the wall of the playpen, she lifted Jack’s dress enough to check his diaper. Nodding to herself, she looked down at the remote on the floor. “Trying to turn on the TV, hmm?” Jack nodded, mumbling incoherently around the pacifier. “I think I know just the thing, but you need to sit down and have quiet time, okay?” Jack complied, looking away as he noticed Michael watching from the kitchen, clearly bemused. He groaned into the pacifier as his mom put on
Pretty Ponies of Periwinkle Park. His early bedtime the night before had allowed him to avoid it, but it seemed he would be watching it anyway. “It’s the sort of thing a little girl would watch.” His mom whispered to him. “Just deal with it and remember our arrangement, okay?” She smiled approvingly as Jack bashfully nodded. “Crisis averted, Michael.” She called, returning to the kitchen.
Jack turned his back to the TV, but he could not think of some other way to occupy his time. Would it have been so bad if either his mom or Jessie had put a book or two in the playpen? All he had was some blocks and the doll from last night.
With a shrug, he grabbed some of the blocks and began to stack them. He had enough, he figured, to build a sort of house for the doll, so that was what he resolved to do. It took him a few tries to get it to stay standing, but he eventually felt pretty confident about it.
“I love this movie!” Jack jumped, startled, the left wall of his block house falling down. He turned to see Caitlyn sitting on the couch behind him. Where had she come from? “Are you building a house for your dolly?” She seemed to be waiting for an answer, so Jack pointed to the pacifier in his mouth. “That’s ok, just nod yes or shake your head no, okay?” Jack nodded. “So you are?”
“Yes.” Jack mumbled around the pacifier, nodding as well for good measure.
“Do you like wearing pretty dresses?” Jack shook his head. “Well, what about diapers? Do you really need diapers?” Jack shook his head. “Then why are you in them?”
“My mom.” Jack had to say it a couple times for Caitlyn to figure out what he was saying. Couldn’t he take the pacifier out of his mouth to talk with her? No, she might figure out that he was not a girl then.
“Your mommy makes you wear them?” Jack nodded. “Why?”
“Accidents.” He blushed. Caitlyn nodded.
“Are you my age?” He shook his head.
“Oh, okay. You kinda look like you are, but it’s hard to tell in your bonnet and dress and stuff.” Caitlyn said. “Have you ever been a flower girl? I was the flower girl at my aunt Cassidy’s wedding last month!” Jack shook his head. “I’m gonna tell your mommy that you should be a flower girl! I bet you’d be really pretty!” She dashed away, braids bouncing.
Jack did not think there were any weddings coming up, which he was thankful for, because he could see his mom doing just what Caitlyn had suggested. He could almost see himself in a pink flower girl dress by the time that Caitlyn came skipping back.
“Is that your nursery over there, Jackie?” He sheepishly nodded. “Are you sure you don’t like wearing diapers?” Jack indignantly stared up at her. “Well, why don’t you ask your mommy for big girl panties? I wear big girl panties.” She said proudly. She gasped suddenly. “Can I be your big sister?” She asked excitedly. Jack shook his head. “Why not? Oh, Jessie’s already your big sister, isn’t she? I just have a big brother.” Caitlyn made a face like that was the worst thing in the world. “But if you don’t like diapers, you should ask your mommy for big girl panties.” Unsure of what to say, Jack just shook his head. “Why not?” Caitlyn leaned in and whispered. “Are you scared to ask?” Jack shook his head again, but the six year old came to her own conclusions. “How about I ask for you?”
“Ask what, Caitlyn?” Cursing his luck, Jack watched his mom step into the living room. Before he could even try to stop her, Caitlyn spun around.
“Miss Diane, Jackie wants to ask if she can wear big girl panties?”
“Oh? How do you know?”
“She told me.”
“She did?” Diane looked at Jack inquisitively. He was relieved to see that she did not look angry, just curious.
“Well, kinda. Since she can’t really talk around her pacifier, I ask her questions and she just nods and shakes her head. Isn’t that right, Jackie?” Jack nodded.
“And she really wants to wear big girl panties, does she?” Diane asked with a cheeky smirk.
“Mhm!”
“Jackie, is that true, sweetheart?” Jack sat there for a moment before shaking his head.
“She’s just scared.” Caitlyn said. “I think she thinks you want her to stay in diapers.”
“That’s not true, sweetie.” Diane said, playing along and watching her son squirm more and more. “If you want to wear big girl panties, you can tell me. Mommy won’t be mad.”
“Go on.” Caitlyn coaxed. Jack looked at his mom and tried to signal ‘no’ with his eyes while nodding, hoping that that would get them to leave him alone. Diane smiled.
“I guess you’re right, Caitlyn. Maybe I should keep you around to translate little Jackie’s thoughts for me.” Diane turned to return to Michael, but stopped. “What about being a flower girl, Jackie? Was that Caitlyn’s idea or do you really want to be one?” She just laughed as she walked away, delighting in the poor boy’s stricken look. She almost wanted to keep Jack dressed just the way he was if it meant letting Caitlyn continue to torment him without even realizing it.
* * *
It seemed that the universe had finally shifted in Jack’s favor because, just as he felt his bladder twinge, Michael announced to Caitlyn that it was time to go. He waved good-bye to her with more enthusiasm than he had shown at any point since his mom had woken him up to tell him that he would be wearing diapers on the trip to the cabin. His eyes widened as realization struck. If Michael and Caitlyn were leaving, that meant he would get to go back to his regular clothes!
The second that Jessie and Diane came back from saying their final good-byes, Jack jumped up, but he could not get out of the playpen without someone’s help. The latch had a trick to it that he did not know, no matter how he pawed at it. Spitting the pacifier out, he turned to his last resort.
“Hey, mom, can you let me out? I need to pee.”
“Ask nicely.” Diane said, eager to wring every last bit out of the final moments of Jack’s time in dresses and diapers.
“Mommy, please?”
“Much better.” She unlatched the playpen and Jack ran toward the bathroom as quickly as he could waddle. “If you tear anything on your outfit, mister, you’ll be in big trouble!” She called.
Jack stood in the bathroom, trying to untie the bonnet on his head. Once it was off, he would feel more normal, even with the dress.
Diane opened the door and poked her head in. Seeing his struggle, she opened the door all the way.
“Just come to the nursery and we’ll get you undressed. Then you can go upstairs and get dressed in your clothes, okay?” Jack grinned from ear to ear, not even caring when Jessie insisted on watching as Diane undressed him. Jack only mellowed a bit when he realized that he had yet another naked dash across the cabin ahead of him, but the prize at the end of it made it all worthwhile.
“Can I go get dressed?” He asked as his mom put the dress back on the hanger after thoroughly inspecting it for stains or tears. She looked him up and down.
“Let’s see how well your punishment worked. Ask me nicely.” He blushed.
“How nicely?” Diane smiled and came over, whispering in his ear. Jack stood there, hands over his crotch. All things considered, this last request was not so bad.
“Mommy, may I pretty please go put my big boy clothes on?” Jessie tittered in the corner, but Diane silenced her with a look.
“You may, Jack.”
* * *
He had had no idea how accustomed he had become to the thick diapers between his legs and he had to do a couple laps around the room in just his underwear to readjust himself to walking with his thighs closer together. Once he was satisfied, he pulled on his shirt and shorts, standing triumphantly in front of the mirror. He had done it. He had once again assumed his role as a twelve year old boy without so much as a frill or bow in sight.
“And I’m going to keep it that way.” Jack said firmly.
“All set in there?” Diane asked, knocking on the door. Jack was surprised at the formality. Even at home, his mom and Jessie both came into his room whenever they wanted to, regardless of what he was doing or how he was dressed.
“Yeah, mom.” He called. Both she and Jessie entered.
“You look”
“Weird.” Jessie interjected.
“Handsome was what I was going to say.” Diane said with a frown toward her daughter. “Now that your brother’s out of punishment, I’d be careful if I were you, missy.”
“So we’re going to share a room?” Jack said.
“Yep. You’ll be on the bottom, Jessie will be up top.” Diane said, pointing to the bunk bed.
“How come he gets to be on the bottom?” Jessie asked indignantly.
“Think about it, Jessie. Do you really want Jack on the top bunk?” Jack looked from his mom to Jessie, puzzled. What did she mean?
“Oh. Ew, no.” Jessie said at once.
“You’ll be happy to hear, Jack, that we’ll try tonight without diapers, since you didn’t wet at all last night.” Diane said. “But remember, best behavior or you’ll be back in the nursery and you won’t be getting out again.” She looked him right in the eye. “What does that mean?”
“I’ll be good.”
“Go on.” He knew what she wanted to hear. Glancing over at Jessie, he sighed.
“I’ll be a good little boy.” He muttered.
* * *
It amazed Jack just how quickly life returned to normalcy. He and Jessie went swimming in the lake, they went on a hike through some woods, getting a glimpse of the neighbor’s cabin, but they turned back before either of them saw the neighbors, and that evening, they went into the nearby town for burgers. Jack was having such a good day that he did not even grumble about Jessie getting to sit in the front seat while he was once again stuck in the back.
“Maybe while we’re in town, we can buy you those big girl panties you were begging for.” Diane suggested. Jack glowered in the back seat, but Jessie was so curious, he had no choice but to explain the whole situation, hoping his mom did not comment on the fact that he left out the bits about being a flower girl. All the same, Jessie laughed and laughed.
“Sounds like you and Caitlyn became best friends, hmm?” but thankfully, they did not try to push it any further.
Before any of them knew it, it was dark and time to change into pajamas. Jack took a quick shower and stood in the bathroom for a moment, reveling in his boxer briefs. It had really not been that long, but it felt like an eternity. He was in such a good mood, even his childish pajamas with their smiling clown fish could not sour it. Glancing at the tag, he confirmed something he had suspected. They really were meant for a boy several years younger than him, which only made him sigh and grumble at how perfectly they fit now that he was not diapered.
“I’m not diapered.” He said to himself, loving just how wonderful that sounded. He felt as though he were floating as he left the bathroom and went to join his mom and sister on the couch.
Betty Pearl's Sissy Stories 20.1
Topic: Secluded Cabin Sissy (Read 75244 times)
