Betty Pearl's Sissy Stories 20.1
Sissy Story Archives (older stories) => Recent Inactive Sissy Stories => Topic started by: Andlat on November 17, 2018, 09:07:14 PM
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“No way!” Jack exclaimed, just barely able to keep an expletive from peppering his protest. Judging from his mother’s expression, she knew all too well how close he had come to uttering an obscenity.
“I made my decision, mister.” She said. “We cannot make a dozen pit stops if we want to reach the cabin today. The sunsets are supposed to be magnificent.” Sensing that he was determined to be stubborn, she sighed wearily. “Jacob, please be reasonable.” Sure enough, Jack stood firm.
“But Jessie will”
“I’ve already explained it to your sister.” He gaped. His mom had already told his twin sister that she was going to put him in diapers for the car trip? How could she! “She promised not to tease you. Do you want me to call her in here?”
“No.” Jack said, his anger a bit deflated. It was too late.
“Jessie!” His twin sister appeared in the doorway a bit too quickly for his liking. “Could you please promise Jack to his face?”
“I promise” Jessie began, a cheeky grin slowly sneaking onto her face before she quickly restrained it again. “Not to tease you about your diapers.” She quickly covered her mouth to hide the giggle.
“There.” Their mother sighed. If this was how they were at twelve, she feared what true adolescence would bring. “Now, shorts and undies off.” His face turned scarlet. Somehow, he had not thought it would ever come to this. Why did he think that his mother would stand down? She always got her way and Jessie was little better. With the two women united against him, what chance did he really have?
Turning his back to his mom, he undressed until he wore nothing but his favorite band t-shirt. Covering himself the best he could by tugging it down, he turned back to her.
“Lie down on your bed.” She said, holding up what appeared to be a small stack of white towels. “This will be my first time using cloth, possibly ever, so I’m not sure how thick it should be.” His mom said thoughtfully. “We’ll use all three, just to be safe.”
“Where did you find these?”
“Butt up.” He complied, although it was difficult with his hands still cupping his privates. He lowered his hindquarters again, feeling the large, soft stack slip under him. “A coworker with a daughter who had a bedwetting problem. Apparently her skin was sensitive to the sort of plastic they use in diapers, so they used these cloth ones. Something like that, at least. Denise likes to ramble, so I can’t remember every detail. I do know they were her daughter’s though.” The idea of getting a girl’s handmedown diapers made him blush. He idly wondered for a moment just how many people his mom had told about her plan to diaper her practically teenage son. He did not know if he would like to know the answer.
Sprinkling some powder into the diaper, she lifted it up between his legs, swatting his hands out of the way.
“Hold still. These pins can hurt if you wiggle too much.” She said, pinning the diaper snugly around his waist. He could feel it pressing against his thighs. It vaguely resembled underwear in form, but it was dramatically thicker. He started to sit up, but his mom stopped him. “One last thing there, kiddo.” She said. “Those won’t hold much. You need something over them.” She looked around. “Must’ve left it in the other room. I’ll be back in just a moment.”
Jack stared down at the diaper, trying to not notice the pink diaper pins holding it around his waist. He got off his bed, having to take a moment to adjust his center of gravity to avoid losing his balance. He took a few steps, feeling the bulk of the diaper pushing his legs farther apart, forcing him into a sort of waddle. They were cotton just like his boxer briefs, but they felt so different. There was an unfamiliar slipperiness to them that seemed constant, and of course their soft bulk was something he wondered if he could ever get used to. It was only for a few hours. Once they reached the cabin, he knew he would be back in his normal clothes, ready to enjoy a few weeks at the lake.
“What do you think?” His mom asked suddenly, causing him to jump. He waddled back toward the bed, but she stopped him. “You can stay standing, Jack.” She kneeled down and held out something for him to step into. He looked down and balked.
“What is that?”
“They’re called plastic pants.” She said. “I know, they’re pink and they’ve got a little bit of lace around the legs, but Denise assured me that they’re the only ones she could find that weren’t ripped.”
“But”
“No buts, mister, unless you want yours red and sore under your” she stopped before she said ‘diaper’, knowing that it would throw him into another fit. He got the message all the same. He gently placed his hands on her shoulders as if he did this all the time and stepped into them. She pulled them up his slender legs and over his thickly diapered bottom. “They fit perfectly.” She remarked. “I need to take a picture, c’mon.” She grabbed his shoulder and led the waddling boy out of his bedroom, leaving his discarded shorts behind.
Peering out of her bedroom across the hall, Jessie giggled as she saw her brother waddling around in frosty pink plastic panties, bulging from the diapers underneath. She disappeared back inside when he shot her a look that could kill, it seemed, although it was somewhat undercut by his hilarious get-up. He always thought he looked so tough in his Flight of Dogs t-shirt, but he looked ridiculous right now.
“Mom, why do you have to take a picture?” He asked, trying without success to keep a childish whine from his voice.
“To show Denise how perfectly they fit you. I won’t show her your face or anything, if you want, but I did tell her that you’re my son, so she’ll know that much.” She retrieved her phone. “Lift your shirt out of the way please, Jack.” She said. The moment he complied, she took several photos in rapid succession. “Show me the back too please.” The bashful boy obeyed, glad to have his face turned away from her, at least until he realized he had turned right in the direction of the full-length mirror, giving him a view of his peculiar wardrobe. Seeing his discomfort, his mom put her phone away.
“Can I go put my shorts on now?” She eyed his diaper with those darling pink plastic panties stretched over its bulges and nodded, secretly curious to see if he would be able to fit his shorts over his big diaper. She stifled a giggle not unlike Jessie’s as he ran out of the room, waddling every step of the way. She knew that there was no chance of him fitting anything over those diapers. She had made sure of that.
Sure enough, when she walked into his bedroom, he was trying in vain to force his shorts over his fat diaper, grunting from the effort. She watched for a moment before finally deciding to intervene.
“Doesn’t look like it’s going to work, buddy.” She said gently.
“What am I going to do?”
“You can ride in the car in just your shirt and diaper.”
“What?” She had known he would react just like that, but she remained firm.
“The car’s in the garage. No one will see you.”
“But”
“But nothing. The cabin we’re going to is totally secluded. You can get dressed there.” Jack was about to continue arguing, but he saw his mom’s face and fell silent.
* * *
Out of necessity, Jack tightly gripped the bannister as he went down the stairs, feeling the fat diaper shift against him with every step. He sat on the couch in the living room, shifting a bit, trying to get used to the fat diaper under his bottom. He pulled a pair of black socks onto his feet, followed by his favorite pair of well-worn sneakers. He could not believe how strange it felt being fully dressed except for pants. Even wearing just his underwear would have covered more than this diaper did! He sighed, but reminded himself that it would only be a matter of hours before he had his boxer briefs back on. Everything would be back to normal then. He just knew it.
“Alright, kids! Everyone into the car!” Mom said, gesturing toward the door to the garage. Nervous about Jessie seeing him, Jack ran toward the door as quickly as the thick cotton between his legs allowed him to waddle. He practically dove into the backseat of the car. “Buckle up!” His mom said with a chuckle. He obeyed, which only served to remind him of his bare thighs and fat pink-pantied diaper. He had never appreciated how thin his normal clothes were until he had to sit there with all those layers of padding under him.
Jessie got into the front seat, looking back at her twin brother and smirking. She had clearly not been told about his lack of success in covering his humiliating undergarments. He stuck his tongue at her and would have done more, but their mom got in the car and both kids snapped into good behavior.
Jack sat in the back seat of the car, unable to stop himself from playing with the lace around the legs of the plastic panties he wore. His head still spun as he tried to make sense of just how he had ended up sitting in the back seat in a t-shirt and girly diaper.
Once they were about fifteen minutes away from the house, the reality of the situation sunk in for Jack. Since he did not have anything over his diaper, even if they did stop, he would not be able to get out to use the bathroom. He would have no choice but to use the diaper! No, he would just hold it. How hard could it be? As if on cue, he felt the very twinge in his bladder that he had been dreading.
“Mom, how far is it to the cabin?” He tried his best to hide his anxiety about his bladder’s growing ache.
“Quite a while, Jack.” His mom said. “We’ll stop for some lunch in a couple hours. That’ll be roundabout the halfway point.”
“We’re going to stop for lunch?” Jack asked nervously.
“We’ll either go through a drive thru or Jessie and I will go inside and get something to go. You won’t even have to get out of the car until we reach the cabin.” He tried his best to look relieved, but he had his doubts about being able to hold it all that time.
“If you’re thirsty now, there are some bottles of water in that little cooler behind me.” His mom said.
“Could you hand me one, Jack?” Jessie asked. He handed it to her. “Not thirsty, bro?” She asked with a grin. He just shook his head and looked away.
By not thinking about it, Jack realized that his bladder ached less and he began to feel confident about being able to hold it for the entire car trip. The only time he even thought about his bladder was when his mom or Jessie asked him about the status of his diaper periodically. He still could not even believe he was in a diaper. Sure, he had had some close calls on long car trips, but the last one he could remember had to have been at least three or four years ago.
He mentioned that to his mom, but Jessie immediately jumped in to correct the record. Being his twin sister, they were in the same class at school, so there was very little chance of anything happening in his life without her knowing about it.
“Just last week, you were begging Mrs. Axworthy to let you go to the bathroom.” She said.
“Oh, and don’t forget that field trip where you nearly wet your pants.” His mom added.
“That field trip was in second grade!” Jack protested.
“It was fourth grade.” Jesse corrected again. In Jack’s opinion, she was a know-it-all all too often.
“Was not!” Jack retorted.
“Inside voice in the car, Jack. Both of you.” Their mom reminded them. They were so alike in so many ways they did not even acknowledge. “The fact of the matter is, mister, you’re in diapers for the drive to the cabin and, guess what? You’ll be in them for the drive back too.”
“But”
“No buts, Jacob Anthony.” She said firmly. “If you manage to stay dry, we’ll talk about doing a thinner diaper that you can wear your shorts over.”
“But I like seeing his plastic panties, mom!” Jessie said. “Can’t we put it up to a vote?”
“We’ll see.” Jack sulked in the back seat once again. Jessie was always so eager to demonstrate that she was the more mature of the twins and it was hard to argue that she was not while he was sitting in the back seat in a literal diaper.
“We’ll be stopping for lunch in about half an hour. How’s your diaper, Jack?”
“Dry.” Jack muttered.
“I couldn’t hear that.” His mom replied. He could not be sure if she had genuinely not heard him or not.
“I’m dry.” He repeated, crossing his arms.
“Alright. If you keep mumbling, I’ll have to start checking you myself.”
“I can do it!” Jessie said eagerly.
“No, only I’ll do it.” Jack was relieved that his mom had finally put the brakes on Jessie’s teasing, even if it was just for the moment.
* * *
They arrived at Bouncy Burgers, but the drive thru was out of order. Jack’s mom simply smiled and parked.
“We’ll run inside real quick and get food. You sit tight here, Jack.” He nodded, grateful that he could hide in the backseat from nearly every passerby, unless someone came right up to the car. He watched as they disappeared into the restaurant, leaving him alone with his thoughts and, unfortunately, his urgently aching bladder. He groaned and squirmed. What was he going to do? The bathroom was right inside, only a short walk away, but he could not go in there in a t-shirt and a diaper! He refused to, even if it meant squirming like this for the rest of the trip.
Jack tried to push his thighs together, but the fat diaper between them refused to allow it. He bit his lip, hoping that the pain would distract him from his dire need to pee. He had to think of something. Could he find something to use as a makeshift toilet? The car was clean of empty bottles, at least in the back. Looking toward the front, he spied Jessie’s bottle of water with only a small swallow of water left. Did he dare? He unbuckled his seatbelt and stood, stretching to try to grab it. It was down on the floor of the front seat, but he stretched as far as he could, his pink plastic pantie and diaper-clad butt sticking up high in the air.
“Almost, almost.” His fingertips were brushing the blue cap. He was so close. Just a tiny bit more. He stretched with all his might, focused on nothing more than grabbing the bottle. All at once, he felt his bladder release.
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8) Andlat what a great start more please Sissybaby Kevin???? :P
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Terrific start to the story! I love how matter of fact Mom and Sis are about the main character wearing a diaper. I can't wait to see how far his regression goes and how Mom justifies it.
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Terrific start to the story! I love how matter of fact Mom and Sis are about the main character wearing a diaper. I can't wait to see how far his regression goes and how Mom justifies it.
They're trying to show Jack that there's nothing to be embarrassed about with their matter-of-factness, but it does seem to embarrass him more, doesn't it? I'm so glad you're enjoying the journey so far and I hope that you continue to enjoy it as they continue on their roadtrip and vacation.
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Can't wait to read more! Really curious to see if/how Mom will talk Jack into a pacifier.
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Great start looking forward to the next chapter when you have time to do it. Love that you cut it off just as he peed his diapers
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By some strange stroke of luck, his mom came out of the restaurant without Jessie, making a beeline for the car, carrying two cups in her hands. She got in and looked back at her son, who was sitting there in disbelief, his soggy diaper pressing against his skin. He took his drink from her and took a sip, feeling tears well up in his eyes.
“I wondered if you might do that now that you're alone.” She said simply. “Let’s get you cleaned up before your sister gets back, hmm?” She came around to the door nearest him after grabbing a nondescript bag from the trunk. “Lie down across the seat.” She instructed. He complied bashfully, feeling the diaper squish under him as he shifted positions. “I’ll make this quick.” She slipped a towel under him and then pulled down his plastic panties.
Jack stared up at the ceiling of the car, trying to ignore the fact that his mom was currently cleaning his most delicate areas with baby wipes after he had wet himself. He felt as though he might die of humiliation, but at least Jessie was still inside. He raised his head enough to look to make sure she was not coming back.
“Almost done.” His mom said, genuinely working as quickly as she could to get him all set before Jessie returned. “I guess I didn’t diaper you too thickly last time, so we’ll stick with that.” She slipped the triple thick diaper under his raised bottom, powdered, and then pinned it around his waist. She took a moment to gather the sodden diapers and plastic panties into a waiting plastic bag. “Those plastic panties are soggy, so I hate to break your heart, but you can’t wear them again.” Jack almost felt relieved, but then he saw the new pair he would be wearing shortly.
If the second pair of plastic panties had been identical to the ones he had been wearing, Jack would have accepted it. Honestly, since they were yellow instead of pink, if they had been even a little more lacey than the first pair, he would have done his best to just grin and bear it. What his mother revealed, however, was something he could not have even imagined. She held a pair of yellow plastic panties with white lace around the legs and rows of white lace ruffles on the seat. On the front were two little yellow roses and an enormous white bow.
“Aren’t you glad I went with the pink ones first?” His mom asked, trying her hardest to lighten the mood. Jack remained silent, his feelings about them more than apparent by the mortified look on his face. “I promise, we’ll take these off the very minute we get to the cabin.” She said, slipping them up his legs. “There.” He got off of the car floor and sat back down. Even the still unfamiliar sensation of the padding under his bottom could not hide the sensation of the lace ruffles.
Jessie returned to the car with the food and immediately noticed her brother’s new plastic panties. Her mom smiled, ready to restrain her daughter’s teasing, if need be. All the same, she knew that it would better to just let her get over it right away.
“Jack, show your sister the back.” She said. Jack shifted on the backseat into almost a crawling position, quickly returning to sitting after giving his sister the briefest glimpse of his prissy rump.
“Rhumba panties, mom?” She exclaimed in ecstatic disbelief. “Where did those come from?”
“My co-worker Denise, same place the rest of Jack’s diapers came from.”
“They’re not my diapers.” Jack muttered, but his mom and sister ignored him.
“Her daughter’s all grown up, so this was quite a while ago. Apparently she loathed having to wear plastic panties like those, that’s why they’re in such good shape.”
“I can relate.” Jack mumbled, staring out the window.
* * *
Once Jack had eaten, he felt a little better, but he kept catching glimpses of the humiliating plastic panties he now wore, the bright yellow a stark contrast to both the grey car seat and his faded dark red t-shirt.
“How’s it going back there?” His mom asked. “Diaper still dry?”
“Yes.” He replied through gritted teeth. He was sick and tired of being constantly reminded.
“We should reach the cabin in a few hours. If either of you wants to nap, I’ll be sure to wake you up when we get there.” Neither of them took her up on the offer. Jack tugged his t-shirt down over his diaper the best he could and stared out the window, trying to think of anything that would help him forget his predicament. In the rush to leave the house, he had forgotten to grab his music player out of his suitcase, which meant that it was stuck in the trunk.
“Mom?” He asked.
“Do you need a change?” His face turned red.
“No, I’m” He could not bring himself to finish the thought. “When we stop next, can I grab my music out of my suitcase?”
“I don’t think we’ll be stopping again, Jack. We’ll be to the cabin before you know it.” He sighed melodramatically.
“I wish I could have gone to camp this year.” He muttered. All of his friends had left the week before, but his mom had told him he can’t go because of their plan to go to this random cabin. He just knew he would not have anywhere near as much fun at a cabin with his mom and his goody-goody sister.
* * *
“Are we almost there?” Jack asked as he felt his bladder twinge again. He refused to wet his diaper again. It felt like it had been a month since they had stopped at Bouncy Burger.
“Soon.” His mom said simply.
“How’s your diaper?” Jessie asked.
“Don’t shout, Jessie. We’re all in the car.” Jack smirked, loving any time that Jessie got in trouble, but his mom then added “answer your sister, Jack.”
“It’s still dry.” Jack said, staring out the window. Why was Jessie being so annoying? It would have been funny if their roles were reversed, but there was nothing funny about him being stuck in a diaper and frilly yellow plastic panties. That much was for sure.
Jack tried a few more times to get updates on their estimated time of arrival, but his mom continued to answer him vaguely. Soon, we’re getting there, she never seemed to give a solid, clear answer. Regardless, his resolve grew stronger and stronger that he would not wet his diaper again. He could, and would, make it.
Once again, it seemed as though the universe had other plans. The car hit a bump just as Jack’s bladder twinged again, causing him to lose control. Quickly regaining composure, he hoped that neither his mom nor his sister would realize what had happened. He sat as still as a statue, waiting for a snide comment from Jessie or a concerned comment from his mom. None came. He had gotten away with it, it seemed. He settled back in. Surely they must be nearly there. With any luck, he could slip away and take the diaper off with no one being the wiser. He returned to staring out the window, the wet diaper sticking to his skin. He hated to admit it even to himself, but the diapers really were not that bad when they were dry. Wet, however? He did not enjoy that one bit.
* * *
“We’re here!” His mom announced as she took the final turn and the cabin came into view. Even though she had kept calling it a cabin, it was more accurately a full-fledged house on a hill, behind which stood the splendor of Lake Vermillion. Tall pine trees stood around the property, providing a sense of tranquility and privacy. “Alright, kids. There’s a lot of groceries in the trunk, so let’s be sure to carry those in first.” Jack got out of the car and headed toward the cabin. He tried to hurry, his soggy diaper causing him to waddle even more than he had that morning.
“Jack, where are you going?”
“To change!”
“Let’s get everything inside. Your clothes are in the trunk too anyway.” He could not argue with her logic and waddled back over, trying to ignore Jessie’s half-hearted attempt at hiding her snickers at his expense.
Rushing, Jack tried to get everything inside as quickly as he could, but neither his mom nor his sister shared his desire for haste. At long last, all of the groceries and their luggage was inside.
“Where’s my room?” Jack asked, holding his suitcase.
“That’s the thing, Jack. Your sister and you are going to share a room.”
“Why?”
“There’s only two bedrooms upstairs.” His mom explained. "One for me, one for you and your sister."
“I’ll sleep on the couch or something.” He said, looking out of the kitchen into the living room. He saw a television that looked small, but only a year or two out of date, and a shelf of board games and books by a couch that looked nicer than the one they had at home.
“I’m pretty sure there’s a bunk bed in the room upstairs.” His mom replied. “It’s not like you two are going to have to share a bed or anything.” She eyed his diaper and lost her train of thought. “Jacob, how long have you been wet?” He felt like all the blood drained out of his face. Jessie giggled, but her mom gave her a sobering look. “Jessie, take your suitcase and your brother’s upstairs.” Jessie could tell that her mom was in no mood for arguing, so she obeyed silently. “Do you really not want to share a room with your sister?” It was not the question that Jack had expected.
“Um” he said, caught completely off-guard. “I mean, if I can just sleep on the couch?” His mom shook her head.
“Nope. Come on.” She led him into the living room and then turned left toward a closed door. What was this room, he wondered? And why had his mom had Jessie take his suitcase upstairs? She opened the door and his jaw dropped.
The room they stepped into was a pink and white nursery with all the furniture and accoutrements one would expect to see. A crib stood against one wall, a changing table against the opposite next to a little pink and white dresser. White lacy curtains allowed light in from a window. In one corner was a small collection of dolls in dresses near a bookshelf and a rocking chair. A door between the window and the crib, Jack figured, led to a closet, but he did not want to know what was inside there.
“Since you’re so against sharing a room, this one will be yours.”
“I can’t.”
“Why not? It’s just a room.”
“Where will I sleep?”
“In the crib, of course. We’ll leave the side down and all that, don’t worry.” He stared at her. This was a joke, right?
“Fine.” He said. “I’ll share a room with Jessie.” To his surprise, his mom shook her head.
“Nope. You said you didn’t want to and, frankly, someone who’s wet himself twice today would probably be more comfortable in here.” Grabbing his wrist, she yanked the waddling boy over to the crib. “Now, I think you could use a quick nap, don’t you?”
“Mom. I can’t sleep in here.”
“Sure you can.” She said. “My mind’s made up, Jacob.” She lowered the side of the crib and pulled back the blanket, revealing the pink sheets with fluffy white lambs and bunnies happily bounding along. “Into bed.” He did not move. “Jack, get into bed.”
“This is crazy, mom.” She looked him up and down, almost as if she was sizing him up. Jack took a slight step back, not in an attempt to escape, but just from his mom’s unnerving expression.
“Here’s the deal.” She said. “You can either willingly get into this crib or I can call Jessie down here to help me get you into it.” Jack sighed and reluctantly complied. She smiled and pulled the covers over him. “Since you were so argumentative, perhaps we should do this.” She raised the side of the crib, trapping him inside.
“Mom!”
“Hush. I’ll come let you out in a little bit. If you need to go potty, just use your diaper.” With that, she left him in the nursery.
Jack glared up at the ceiling, seeing the pink and white nursery all around in his peripheral vision. He wiggled and squirmed until the blanket over him had loosened enough to let him sit up. The crib was built for someone of roughly his size, which was confusing for him at first, but it soon dawned on him just how planned all of this was. He had been manipulated into this situation, so now how would he be able to get out of it?
Moving around the crib, he examined the bars. They were too high for him to climb over, but maybe he could find a latch or some other way to lower the side so that he could escape. If he was quiet enough, he could sneak out of the room and find his clothes. He felt butterflies in his stomach as he remembered that his mom had had Jessie take them upstairs. He could not be sure, but he had a sneaking suspicion that Jessie was in on the plan. His chances of finding his clothes seemed to be slimmer now, but he remained determined to at the very least find his way out of this crib.
He reached through the bars and felt around the outside. There had to be a way to get out of here, he just knew it, but how? He sat down with a resigned sigh, which only reminded him of how soggy his diaper was. He looked down at the frilly yellow plastic panties. How had he forgotten about those? He refused to accept that he was getting used to wearing these girly diapers.
“Could I take them off?” He muttered to himself. They felt pretty wet and he did not want to know what would happen if he got pee on the mattress of the crib. He shrugged. “Guess I’ll just stay in them.” He muttered, putting his head back down on the pillow. Since he knew that his mom had planned all of this, the question on his mind was why was she doing this? Had he done something that pushed her to go to these lengths to punish him? He could not think of anything. Sure, he got in trouble every now and again, but Mrs. Axworthy had only sent a note home about him once, and that had been last winter.
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Oooooohhh I think someone is gonna be a cute baby girl heheeh poor jack ou it’s Baby Janice hehe I think his mommy already planned this in advance hehe
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Congratulations on an outstanding story so far. I think the theme is fairly unique in the genre (my bad if it's not but then references appreciated) and has long been a fantasy of mine. So, thank you.
The introduction of the "surprise nursery" was perfect and you are now one of my story heroes. You did hint that more was to come at the car stop when Mom introduced the yellow rumba panties after saying the pink plastic panties were the only ones that weren't ripped but you did a wonderful job of introducing it. My only very, very minor criticism is the crib bars being too tall is a bit of a stretch (no pun intended). A 12 y.o. boy on average should have about 5.5' - 6' of reach, without jumping. So, for bars to be too tall they would have to be over 6' above the mattress (unlikely) or too close to ceiling to squeeze through. Sorry for the detour but I like to put myself in the situation and think it through.
Also agree with others that Mom had this well planned and a "new baby girl" is soon to appear. Not sure if Jessie was fully aware of plan since she seemed surprised at the rumbas but she'll clearly be an enthusiastic participant. Would love to know the backstory, otherwise Mom comes off as a bit sadistic in her treatment of Jack. Doesn't seem like this is about Jack's somewhat weak bladder. Also, why is Jack not fighting back if he doesn't feel he deserves the punishment? He seems to be too easily resigned to his mother's control. I tend to opposition myself unless convinced otherwise.
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Pierrylouys - You may be more right than you know! Thanks for reading!
Babycakes - One of the frustrations of my advanced knowledge is that I'm writing part 4 and you've only read the first 2 parts, so it makes it difficult for me to discuss things that you haven't yet experienced. Suffice to say, some of the things you've brought up may very well occur by the end of part 3.
As for the matter of the crib, let me refamiliarize myself with what information is in part 2... The bars are not even as tall as Jack himself is, but he's not the most athletic of boys and lacks the upper body strength to get out of the crib and I would imagine the diaper between his legs would complicate matters. For hand-wavy plot-centric reasons, he needs to remain in his crib. Once the initial shock of his treatment wears off, he'll begin to consider escape attempts. Don't you worry.
Thanks so much for reading and especially for sharing your thoughts! It warms my heart on these cold November days to know that I have readers enjoying my story. :)
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Loved the second installment, especially the reveal of the obviously pre-planned little girl's nursery. The main character (is his name Jacob? Or Jack? It's inconsistent) is convinced at the end of this installment that he's being punished. I think it'd be amazing if his Mom came in after his nap and with him still locked in his crib (just give it a closing/locking top, that solves the bar height problem) and had a long talk with him about how she thinks he's really a girl and is going to help him transition back to baby girlhood. I'd love it if Mom would acknowledge that this transition will be tough for him, but all the while she's also convinced it's for the best for him. It would be so hot to have her say, firmly but kindly, that he's now basically a toddler girl from now on.
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Loved the second installment, especially the reveal of the obviously pre-planned little girl's nursery. The main character (is his name Jacob? Or Jack? It's inconsistent) is convinced at the end of this installment that he's being punished. I think it'd be amazing if his Mom came in after his nap and with him still locked in his crib (just give it a closing/locking top, that solves the bar height problem) and had a long talk with him about how she thinks he's really a girl and is going to help him transition back to baby girlhood. I'd love it if Mom would acknowledge that this transition will be tough for him, but all the while she's also convinced it's for the best for him. It would be so hot to have her say, firmly but kindly, that he's now basically a toddler girl from now on.
He goes by Jack, but his full name is Jacob. It's a little different, but he'll mostly go by Jack except when he gets in trouble with mom. As an aside, Jessie will have some nicknames for him down the road too.
As will hopefully become increasingly apparent as the story progresses, Jack is mostly in the dark about what he'll be subjected to, so unfortunately, his mom won't be revealing her full plan for him quite yet. He's in a girly diaper, but still wearing his boy t-shirt, so it's still early days yet.
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I really want to see his downfall to babyhood hehehe he gonna be a cute baby girl
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More, More, More I just love the story so far. :D
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I hope you enjoy where it goes next! All these comments are making me so happy.
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Jack must have dozed off, because the next thing that he remembered was his mom standing over the crib, smiling down at him. He could hear the soft sound of rain hitting the window. It took a moment to remember where he was.
“Didn’t think you’d actually nap.” She said, lowering the side of the crib. He eagerly jumped out, noticing a strange dampness on his midriff. “You must have been fiddling with your diaper. You leaked, mister.” She lifted his slightly sodden shirt and pulled it off him, leaving him in just his frilly diaper. “Hop on the changing table.”
“Huh?”
“You’re staying in diapers. I haven’t seen you successfully make it to the bathroom all day.”
“That’s because you haven’t given me a chance!” He protested, which only earned him a smack on the thigh.
“No yelling, Jack. You’ve been testing my patience all day. Keep it up with the outbursts and I will spank you.”
“You” Jack paused to try to calm his voice down. “You haven’t spanked me in years.” She smirked.
“And you haven’t been in diapers for years. Move it, mister.” He begrudgingly trudged over to the changing table, muttering darkly under his breath. His mom came over, frowning. He lay down, arms on his side. She grabbed the strap on the changing table and secured it across his stomach and wrists.
“I’m going to go grab something. Stay here.” She said. Her tone made it abundantly clear that he would regret disobeying, so he would not have dared to, even if he could move his arms. Was this the spanking she had threatened? She had always just used her hand when he was little, but maybe now that he was older, she was going to use a wooden spoon or something? He did not like waiting. He tried the strap, but could not get it to loosen one bit. He was stuck on this changing table in a little girl’s nursery, wearing nothing but a little girl’s diaper. He silently prayed that Jessie would not find him like this.
His mom returned a moment later. When he saw what she held in her hand instead of his t-shirt, he almost wished he had tried to escape. It was not a wooden spoon, but it was not much better.
“Open your mouth.” With a groan, he complied and the bar of soap took up residence in his mouth. “Keep that there.” Her son unorthodoxically pacified, she tugged down his plastic panties and set to work.
He wished that he had some way to turn off his taste buds. It had been at least a year since he had last gotten his mouth washed out with soap, but the taste was not something he had forgotten. Worst of all was the fact that the feeling of cold wipes on his tender areas as his mom cleaned him up made it impossible to just ignore the soap in his mouth and the diaper change that his mom was subjecting him to.
“Since you’re going to be in diapers for a while, you’re going to be getting diaper cream now with every change.” His mom said, rubbing it onto his bottom. “However! Just because you’re in diapers does not mean you’ll have to use them. If you need to go potty, just tell me. Or your sister.” She shook her head at his scandalized expression. “I just want to make it as easy as possible for you to get out of diapers, Jack.” She explained. “If you can go a whole day without any accidents, you’ll get your regular clothes back.” Never one to pass up such an opportunity, she gave his raised bottom a couple smacks. Jack almost bit down on the soap in surprise. “Just to remind you I mean business.” She said.
She pinned the thick cotton diaper around his waist. Jack hated that he was beginning to get used to the feeling of a fat cotton diaper between his thighs. He quickly reminded himself that the diapers were just temporary. He would be back in his old underwear in no time.
“By now, you may have figured out that this is my co-worker Denise’s cabin. Maybe you’ve even realized that her daughter was not really the bedwetter I told you she was. I won’t bore you with the details of her condition. Suffice to say, Denise and her wife thought it would be easiest to just have a nursery here for her, as well as the one at their house.” Jack looked up at her with confusion. “Why am I telling you this? Well, the only thing that matters for you is there will be lots of plastic panties for you to wear.” She began to slip a pair up his thighs that could have been the child of the two pairs he had already worn. It was bright pink and festooned with lace and bows. “Have you had enough soap?” He nodded and she removed the bar from his mouth.
“I promise not to swear anymore.” He said, wishing the taste would go away with the soap.
“I know you do.” She said, stroking his head. “Now, we’re getting to the part that I’m sure you won’t like.” He did not like the way she was alleging he did not mind being diapered and made to wear frilly plastic panties. She gently touched his thigh. “To help in our family goal to get you back to using the potty, I don’t think you should wear pants.”
“It’d be hard to fit them over this thing anyway.” He growled. She gave him a warning look before continuing.
“Yes, but I don’t want you wandering around in just a diaper this whole time.”
“I’ll be out of them in a day.” He asserted confidenty.
“I’m sure you want that, but just to be safe” she turned and opened the closet, revealing a fairly large assortment of dresses. His eyes widened.
“Uh, mom? Is this a joke?”
“Why would it be? Look around the nursery. What else would be in this closet?” She picked out a pink dress that had to be the frilliest, most feminine one in the closet, closing the door. It was a brilliant pink not unlike his plastic panties with lots of fluffy petticoats, white bows and lace, a sash to tie around the wearer’s waist, bubble sleeves with little bits of lace around the ends and a Peter Pan collar. Jack looked at it with revulsion. Gone was his promise not to try to escape as he squirmed, trying desperately to get away. There was no way he would be wearing that! “Squirming? You must be excited to wear it.” His mom teased.
“A dress? Mom, you’re joking. You have to be joking.” His voice quickly turned from anger to desperation. “You’re joking, right?”
“I’m not, Jack. Trust me, this will make it the easiest for you. You just have to lift your dress up and go potty. You’ll be out of diapers in no time.”
“Mom! No, no.” She shrugged.
“You can either wear this dress and keep our original deal or you can stay in diapers for the whole vacation with no potty privileges.” Would she really do that? That morning, he would have never believed it, but now? He had no way of knowing just what his mom would do, what extent she would go to to make a point. Thinking he was hesitant, she twisted the screw a bit more. “Oh, even better. Either wear the dress and take the original deal or I let Jessie see this closet and you spend the whole vacation as her doll.”
“Once she sees me in that” he could not even get the word out. “She’ll do it anyway.” His mom considered this.
“Fair enough. Alright, how about this? You wear this dress and, from now on, you’ll get to pick out the dress you wear every morning. Think of it as further incentive to get out of diapers or however you want. It’s a lot better than your sister getting to pick, isn’t it?”
“Fine.”
“Fine?” More than anything, she wanted her son to say it, to prove his willingness, however reluctant he might be.
“I’ll wear the” he could not bring himself to say it, so he simply just pointed at the dress. “I’ll wear that.”
Appeased, she released the strap on the changing table so he could sit up and watch as she took the dress off of the hanger. Jack watched his mom with growing anxiety. He soothed himself somewhat with the hope that it might not fit. Maybe it would be too small for him! It was even possibly too big, but he figured that his mom would devise some way to get him in it anyway, if that was the case.
“Arms up, kiddo.” His mom said cheerfully. He rolled his eyes. He knew she was trying to keep the mood light, but the fact remained that she was actually putting him in a little girl’s dream dress. “Arms up. Now.” He quickly threw his arms up into the air, making sure she knew it was under protest, and she slid the dress down. He shivered as the soft silky material flowed down his body. Even the slightest movement brought the material in contact with his skin again, so he tried to hold as still as possible. “Stand up.” His mom said and he jumped off of the changing table, the dress’s attached petticoats fluffing out a bit as he did so. The skirt fell to just above his knee, its ample petticoats pushing it out far enough so that he could not even see his feet. “Hold still while I button you up.” His mom said and he felt the bodice tighten around him as she did so, tying the sash around his waist in a big bow to completely enclose him in the dress. “It fits perfectly.” His mom said, fulfilling his worst fear. “Head over to the mirror.” She ordered. He waddled over, gazing with wide eyes at his reflection.
The boy in a punk band t-shirt and black shorts had become the world’s biggest sissy. He felt tears welling up in his eyes as his reflection overwhelmed him. No, crying would be what a sissy would do. He had to remain tough and fight his mom’s efforts to turn him into a sissy!
“I can’t believe this.” He muttered.
“Remember, you’ll get to pick your dress out every day as long as you behave and cooperate today.” His mom said. He simply grunted in response. Was that supposed to be an incentive? As far as he could tell, every dress in the closet was just as bad as the nightmare he had on.
His mom came over and fussed with his dress for a moment. She knelt down and gave extra attention to his petticoats. He gasped as she stroked his leg out of the blue.
“Hmm. You should be okay without tights.” She said as if he had asked if he needed them. “Your legs are still pretty hairless.”
“Mom!” He whined.
“Hush. You’ll get hair there soon enough.” She stood up and kissed his cheek. “C’mon, let’s go get you a snack.” She took his head and led the waddling, humiliated boy out of the nursery. “Jessie!” She called up the stairs. “We’re in the kitchen. Come downstairs.”
“Mom!” Jack whined. “She cannot see me like this!”
“You can’t hide from her the whole vacation. That’s impossible, Jack.” She said with a smile. “It’s like a band-aid, just rip it off.” He stood there with growing anxiety as he heard the sound of his sister approaching the stairs.
“I can’t believe you’re doing this to me.” Jack muttered, crossing his arms and staring at the floor as his sister came downstairs.
“Oh, my god!” Jessie exclaimed as she skidded to a halt on the linoleum floor. “He’s! He’s!” She was so excited, she could not even get the words out. “Oh, my god!” She squealed, which always made Jack shudder.
“Quit your fussing and pouting, Jack.” His mom said. “Look! Jessie’s in a dress too.” Jack begrudgingly looked, but his sister wore a sky blue sundress that seemed the complete opposite of the frilly pink monstrosity he felt so trapped in. His sister’s look of absolute rapture only darkened his mood further, but with the dress buttoned so securely up his back, how on earth was he going to get out of it? “What do you think of your brother’s dress, Jessie?”
“We can’t really call him my brother when he’s dressed like that!” Jessie grinned, looking her squirming brother up and down with an expression far too predatory for the boy’s liking. She seemed to be drawing herself up to her fullest height and he glanced down to see if she was on her tiptoes. She had always been a tiny bit taller than him and he realized that the diaper between his legs forced him into a bowlegged stance that gave him even more of a height advantage.
“Of course you can call him your brother. He’s still a boy! Is there some rule that says a boy can’t enjoy wearing such a pretty dress?” Jack once again felt scandalized
“I’m not enjoy”
“I guess not.” Jessie said, cutting her brother off with obvious relish. “You look very pretty in your dress, Jack.”
“Thank your sister, Jack.”
“Thanks.” Jack mumbled.
“No curtsey?” Jessie asked, her voice mockingly sweet. Jack glared at her.
“Don’t glare at your sister, Jack! I would think you’d feel like you’re on thin ice enough as it is, mister.” She brushed a wayward lock of hair out of his face, resolving to find some way to fix that. “Go on. Give your sister a curtsey. A dress like yours is made for it.” Jack bashfully curtsied sloppily, taking care not to flash his sister his latest pair of plastic panties.
“Make him do it again!” Jessie exclaimed, feeling cheated.
“There will be plenty of time for that later, Jessie. Your brother can’t curtsey all day!” Jessie’s face made it clear that she disagreed, but she remained silent. “Don’t forget, Jessie. You’re the same size as your brother. I wouldn’t think twice about putting you in one of his dresses. With a diaper.” Jessie blushed, but her face was nothing compared to Jack’s. Why was he getting ownership of the contents of that awful girly nursery? In order to recover her pride, somewhat, Jessie returned to teasing her now sissified twin.
“Remember when we were little, Jack? I used to get you into dresses all the time to play tea party and stuff! It’s just like that.” She said. “Although your dress is a bit more than what we wore back then, isn’t it?”
“Shut up!” Jack whined, but Jessie ignored him.
“We haven’t played that in years, Jackie!” His face looked as scarlet as it could possibly get.
“There are some dolls in Jack’s nursery. You could certainly play tea party.” Their mom said. “It’s going to keep raining until the morning anyway, I think. Guess we’ll see the magnificent sunset tomorrow.” Jack looked out the window and saw the grey-black clouds in the sky. Jessie grabbed his hand and pulled, forcing Jack to waddle after her into the nursery he had only just escaped, his petticoats rustling busily over his amply diapered bottom.
“Since it’s your room, you can pick your doll first.” Jessie said cheerfully. Jack looked over the half dozen dolls sitting there. They were all little girl dolls with a few of them showing diapers under their dresses, but none of their outfits came close to Jack’s. “Tough decision, hmm?”
“Uh… yeah.” Jack said. How was he supposed to pick a dumb doll? Even Jessie had not played with dolls in years.
“Want me to help you?” Jack shook his head.
“Can’t we do something else?”
“It’s pouring outside.”
“I know, but there’s gotta be something else we can do. Didn’t mom say there are some board games? Or we could watch a movie or something.” Jessie considered this.
“Tell you what, we’ll each pick out a doll and then we can play a board game or something.” She grinned wickedly. “It’s a compromise.” Jack sighed and bent down to grab the first doll he saw. A squeal from Jessie made him quickly turn around. Without hesitation, she lifted up his dress and drank in the sight of his third pair of plastic panties. “You’re still in diapers?” She asked. He was surprised that his mom had not already explained her plan to Jessie.
“Yeah. But only for today.” Jessie did not seem to hear it, staring down at his diaper until he indignantly pushed the skirt of his dress back down.
“I’m sorry.” Jessie said. “I got distracted. Anyway, what doll did you want?” Jack rolled his eyes and returned to grabbing the doll he had reached for before Jessie’s ridiculous reaction. “Oh! She’s blonde, just like her mommy!”
“Pick out your doll.” Jack demanded, feeling a little mollified by the fact that his sister would also have to carry around a juvenile doll.
“You’re my doll, Jack!”
“That doesn’t count.” She laughed a bit too much at her own joke and then grabbed a doll with the same abandon as Jack had. “Alright, let’s go find a board game.” An idea had occurred to Jack and this was the perfect opportunity to put it into motion.
“Actually, you go find us a board game. I’ll stay here and” he tried to think of some reason to remain in the girly nursery.
“Get your dolly into a prettier dress?” Jessie teased. Jack bashfully nodded. It was embarrassing, but it was not his real plan. Jessie grinned from ear to ear and left the room.
Jack waddled over to the door and listened for a moment. Sure enough, Jessie was engaged in explaining to their mom all about what had transpired in the nursery. He tiptoed toward the stairs, wishing he had a way to keep the dress’s rustling commentary quiet. All he needed to do was sneak upstairs and get to his clothes. It was so simple. What could go wrong?
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O ooo baby jack is gonna get in trouble hehehe I think a nice romper and onesie are in order heheh , and I really think his mommy gonna use a highchair and a stroller for him very soon heheh
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O ooo baby jack is gonna get in trouble hehehe I think a nice romper and onesie are in order heheh , and I really think his mommy gonna use a highchair and a stroller for him very soon heheh
I'm glad you're enjoying poor Jack's torment so much!
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oh yes nice story i to think a nice romper and onesie would be nice
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I can only imagine baby Jackie wearing a frilly romper with snaps riding a stroller , going to park hehehehe
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Thanks for this latest installment. Mom is really running circles around Jack. I love how she keeps pushing him deeper while also seemingly holding out an exit route (which of course he'll fail to get to). I am curious to see if/how pacifiers and female pronouns for Jack get worked into the mix.
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Loving this, Andlat. Looks like he's about to get caught trying to sneak out of his clothes and end up stuck in diapers and dresses for the foreseeable future.
Seems like the seclusion is going to be a focus here, but maybe throw in another cabin not too far away so there is a dash of public humiliation too?
Also want to say I somehow missed Spencer's Day Out when you first posted it. Read it recently and wow that was great too.
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Loving this story.can't wait to read more ..Thank you ..!
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It would be fun to have Denise and her daughter pay a visit. I could totally see something sinister having been forced on the daughter that would terrify our boy! Where else would his mother have come up with this plan and why, after all?
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Very nice story. Will Jack ever find out why his mother is being so, for lack of a better word, cruel?
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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! :)
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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.
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“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.
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I hope you will be to update soon. A very good story.
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I hope you will be to update soon. A very good story.
On a vacation quite unlike the one Jack's on, but once I return, I'll continue the story of his descent into sissyhood! :)
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8) Dear Andlat have a lovely vacation can't wait for you return Kevin??? ;D
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Hope you enjoy your vacation. This continues to be an excellent story and my favorite of all sites that I visit. Thank you for all your work.
I can't wait to see how Jack is further sissified and why this is being done. Mom alluded to the fact that he doesn't understand his treatment, so I hope it is revealed in future chapters. I wonder if Jack's treatment mirrors Denise's daughter? Will Denise and/or her daughter appear at the cabin? I also hope Jessie gets more involved.
The dress description sounds more like it was a little girl's party dress than a baby dress, which would have left part of his heavily diapered bottom in view below the hem. Hopefully, the closet also contains a few baby dresses.
Sorry for running on. I'm just invested in the story.
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Hope you enjoy your vacation...
...The dress description sounds more like it was a little girl's party dress than a baby dress, which would have left part of his heavily diapered bottom in view below the hem.
You're quite right that it's more of a little girl dress than a baby dress. They've only just begun their vacation, after all!
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romper with slaps or onesie under dress would be nice . You do wright great stories hope more soon wish i was him when little
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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.
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being let off easy with the little boy jammies at the end. A girls nighty would be alot better...giggles
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awwwww so cute !! Him wearing his little boy with a thick diapie underneath! I think until the ends of the night someone gonna need a change and a bottle of milk to sleep better heheh
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Krystalasbaby2017 - I don't know that he's getting off easy. Just consider what his twin sister will be wearing compared to his outfit. Besides, it's the first night of a long vacation. Still plenty of time for Jack to find himself in all manner of the girly outfits your dreams are made of.
Pierrylouys - Diane put him in a rather thick diaper. I don't know that he'll be getting a change tonight, but who can say?
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Another great chapter, Andlat. And so soon after your vacation; much appreciated.
Thanks for the background reveal. Denise seems like a very dominant woman, even to Diane. Diane doesn't seem to feel Jack is all that bad but, rather, is being encouraged/manipulated by Denise. The reveal furthers my suspicions that Denise's daughter is really her sissified son. Can't wait to meet her/him.
At the conclusion Diane had just put Jack in 5 diapers, if my count is correct. There was no mention of him leaving the nursery yet so wonder if he'll need to crawl as a result? Also, surprised the plastic panties would fit such a bundle. They must have been designed for a "special" diapering. Finally, I like the cliffhanger in your reply to Krystalasbaby2017, "Just consider what his twin sister will be wearing compared to his outfit." Could Jessie be getting some regression therapy? Can't wait to find out.
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Very much looking forward to more of Jack’s regression and how his twin sister handles it. As someone with a twin sister it is intriguing.
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Jack sat on the couch, conflicted. On the one hand, he felt very grateful to be back in pants, but on the other, his fat diaper and the snugness of the pajama pants only made the entire affair embarrassing for him, especially since Jessie’s pajamas looked like those of a teenager. She wore a simple white t-shirt and shorts with starfish on them. He could not help but feel that she looked several years older than him, even without the diaper pressing against his fleece pants. At least Jessie had not come down in time to see his pronounced waddle as he had slowly made his way from the nursery to the living room, clinging to his mom’s hand the whole way. He had suspected she had made his diaper thicker and that had proved it.
“Who’s going to pick the movie?” Diane asked. “How about Jack?”
“Cute jammies.” Jessie said as he waddled past her to look at the available movies.
“Jack, thank your sister.”
“Thanks.”
“Aren’t you forgetting something?” He looked back at his mom in confusion. She mouthed a reminder to him.
“How am I supposed to curtsey in this?” Jack asked irritably.
“Like this.” Jessie demonstrated with the hem of her t-shirt. “Your turn, Jackie.” He sighed and mirrored her.
“Thanks for complimenting my pajamas.”
“Do it again without the attitude.” Diane said.
“But mom!”
“Do it again or we’ll go into your nursery and find you something that’s easier to curtsey in.”
“This is ridiculous.” He muttered. “Thank you for complimenting my pajamas.” He said, curtseying about as well as he could with his thick diaper and boyish clothes.
“Much better.” Diane said as Jessie squealed with laughter. “Now pick out a movie for us to watch please.” Jessie’s laughter only grew as she watched her brother slowly make his way over to the bookshelf of movies, leaning heavily on furniture to keep his balance as his legs swung out wide to compensate the ridiculous bulk between his legs. He almost fell over when Jessie asked his mom a question.
“Is his diaper thicker than normal?” Jack’s ears burned. Why did she sound so blasé about it?
“I figured we’re close enough to bed that I should put him in a diaper that’ll last all night.” Noticing Jack’s outraged expression, Diane added “just in case.” Jack just tried his best to ignore them, making his way over to the movies. He felt a bit of relief about being able to just sit down to look at them, although he wondered if he might have some trouble standing back up. Now that his mom had fully confirmed that she had made it thicker, he felt like he could feel every single diaper pressing against him, mocking him with its constant presence.
“I’ll be out of them tomorrow.” He mumbled to himself. He just wished he could convince himself that that was true.
“Oh!” Diane exclaimed, overhearing her son’s mumbles. “That reminds me! Jack used the potty earlier!”
“Congratulations!” Jessie exclaimed. Jack looked over his shoulder at them sitting side by side on the couch while he sat on the floor in his diaper and childish pajamas. How had this happened? It was just a coincidence though. He would just pick out a movie and then stand up and be back on equal footing with his sister.
“Thanks.” He said, pulling on the hem of his shirt in a sort-of curtsey. He hoped that he would not be expected to stand and properly curtsey. His effort seemed to please them, so he returned to finding a movie. When he picked, he crawled the short distance to the television and got it all set up.
“Ravagers?” Jessie moaned. “You’ve seen this movie a million times.”
“It was your brother’s choice, Jessie. Quit whining.”
“It’s so dumb.”
“Shush.” Diane said. “Come join us on the couch, Jack.” Jack used the TV stand to get back onto his feet, but the distance from it to the coffee table proved to be too much and he fell down on his bottom. “Good thing you have that padding!” Diane said as Jessie almost fell over from laughter. “Do you want my help?”
“No.” Jack said, his bruised ego on full display.
“Then just crawl over here. It got you to the television, so just swallow your pride.” It seemed sensible, but Jack was too stubborn to admit it. He pulled himself up with the TV stand again and gave it another shot. He thought that running would help, but he just ended up on the floor again.
“You look ridiculous.” Jessie teased. Jack glared at her.
“Don’t glare at your sister, Jack. Stop laughing at him, Jessie. He needs his diapers.”
“No, I don’t!” Jack yelled. This was all too much for him and his anger broke free. “I don’t need diapers!” The way his mom glared at him made him immediately grateful he had kept from swearing.
“Jacob Anthony! What have I told you about yelling?” Both Jack and Jessie froze as they always did when their mom took this tone. “I have half a mind to keep you in diapers until school starts again this fall! Is that what you want?”
“No.” He said in the smallest voice he had. It seemed to mollify her somewhat.
“I know you’re upset about them, but you’ve made it very clear to me that you need those diapers. It’s tough to get around in them and that’s frustrating, I get that, but you don’t need to take it out on me or your sister.”
“But”
“No buts, Jack. Now, are you going to watch the movie with us or is it bedtime for you?”
“I’ll watch the movie.”
“Then you need to behave. Your diapers are supposed to help you contain your accidents. They are not a free pass to behave like a baby. Understand?”
“Yes.”
“You may watch the movie with us, but I want you to promise to be a good little boy. Can you do that?”
“Yes.” He said with a bit more of an edge to it than he meant to. “I” he tried not to look at his sister. “I promise to be a good little boy.” Diane nodded.
“Thank you. Now crawl over to the couch or the chair or wherever.”
“I don’t want to crawl.”
“I can help you walk.” Jessie was clearly trying to appear helpful, but she had her usual predatory grin.
“No.” Taking his mother’s advice, Jack just swallowed his pride and crawled over to the chair, pulling himself up and into it.
“There. I’ve been saying it all day, Jack, but you better consider yourself on very thin ice by this point.” His mom said, giving him one of her trademark serious looks.
“Why isn’t the movie working?” Jessie asked.
“Oh.” Diane said. None of them had noticed, but the television was showing some strange error. “Incorrect Input?” Diane said. “I’m not sure what that means.” Jack was in no rush to get up and try to fix it himself, diapered as he was, so he remained still while his mom and Jessie tried to remedy the situation. Try as they might, they just could not seem to make the movie play.
“Did you try taking the disc out and putting it in again?” Jack asked from his chair. He wanted to be helpful, to earn back some goodwill.
“Duh!” Jessie said.
“Tone, young lady.” Diane scolded. She smiled gently at her son. “Yes, Jack. We did try that. I don’t think your movie’s going to work though. Jessie, how about you pick out a movie for us to try?” Jack groaned softly, but tried to keep a happy face. His face fell, however, when he saw her grab a bright pink case and put a familiar-looking disc in the player.
“Ponies of Periwinkle Park?” He moaned.
“Pretty Ponies of Periwinkle Park.” Jessie corrected. “Your panties put me in the mood.” She stuck her tongue out at Jack, whose face was now quite red.
“I don’t want to watch this!”
“Jack, get over it. It’s just a movie.” Diane said. “And Jessie, get that smug look off your face.”
“But mom!” The twins said in unison.
“I’m not watching this, mom.”
“Then you can go to bed.” Diane replied.
“I don’t want to do that either.”
“Then watch the movie.”
“This is f****** ridiculous.” Jack muttered darkly.
“What was that?” Diane said, coming right over to his chair and standing over him.
“It slipped out.” Jack said.
“That’s it, mister. Bedroom. Now.” Jack could feel the rage radiating off of her. She did not even give him a chance to stand up. She lifted him off of the chair and set him against her shoulder. He did not even realize she could still carry him! He tried to get free, but she smacked his thigh just below his diaper. “Stop.” She said. “Jessie, I’ll be right back. I’m putting your brother to bed.”
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(Little addendum to make an even better cliffhanger, en mon avis!)
“I have had it with your attitude, mister.” Diane said as she set Jack down on the changing table. He remained silent, terrified. How long had it been since he had seen his mom this angry? “I hoped that you finally got it into your head to behave, but apparently not.” He sat there as still as a statue, watching her. She was looking for something, but what? “I would’ve thought that soap would be enough for you to figure out that I don’t want you swearing.” She said as she looked.
“It was just one time, mom!”
“To say nothing of your spanking.” She continued as if he was not speaking.
“Mom, seriously. Why are you doing this?” He glanced to the open door to see if Jessie was sneaking a peek. She was not, but she could probably hear him from the living room anyway. He looked around the pink and white nursery as if he had never seen it before. “This is crazy!”
“What’s crazy is that I hardly even know you anymore. Those friends of yours are turning you into someone else.”
“What are you talking about? I like my friends. We just play video games and stuff.”
“You misbehave in school, you swear. It’s frankly shocking!”
“C’mon, mom. We’re just having fun.”
“Well, it stops now.” She found what she was looking for and came over to him. “Open your mouth.” He complied and she pushed the fat bulb of a pacifier into his mouth. He stared up at her inquisitively and she held her hand over the pacifier to keep him from spitting it out. “Since you can’t seem to keep yourself from swearing,” she slowly pulled her hand away, tentatively testing him. “And you’ve been behaving like a petulant little child all night, you’re going to keep this pacifier in your mouth as a reminder to be a what?” Jack could see in the mirror that the pacifier in his mouth was bright pink with a sparkly silver tiara on the front. “What do I want you to be, Jack?” He stared up at her. How was he supposed to answer with the pacifier in his mouth?
“A good little boy.” He mumbled around the bulb that filled too much of his mouth for his liking. She nodded and smiled. She could not believe how adorable he sounded. She almost wanted to keep coming up with things for him to say.
“Don’t you think you fell short of that?” He simply nodded. “Don’t you think you should apologize?”
“I’m sorry?” He said as best he could. She smiled and kissed his forehead. Was that all it took to appease her? He cautiously studied her. She did not seem mad anymore, but how could he be so sure?
“That’s better.” She said after a moment. “But I don’t think you deserve these jammies any more.”
“What?” Jack exclaimed. “I mean, what will I wear instead?” It was so difficult to speak with the pacifier in his mouth.
“Jammies off.” She said. He pulled his shirt off, but then had to lie back so she could remove his pants, leaving him in nothing but his absurdly thick diaper. He shivered as he looked over his body. He had fallen so far over the course of the day. “Now then, I know you prefer these plastic panties to the other ones you’ve worn. I’ll allow you to keep them on for the night, if you ask nicely.” She held up a finger to silence him. “But I am only giving you one chance, so make it count.” She pulled the pacifier from his mouth. “This goes back in right after.” She gently stroked his head. “Make it count.”
He looked down at the powder blue plastic panties. They only had a few small white bows around the waist, so they honestly were not that bad. He hated that he thought that, but it was what it was. How could he convince her to let him stay in them? His eyes widened as she wordlessly held up a pair of pink plastic panties festooned with lace and bows. He had better lay it on thick! Swallowing his nascent adolescent pride, he took a deep breath.
“Mommy, may I please keep wearing these plastic panties? I promise to be a good little boy!” The pacifier immediately returned to his mouth. He had no way to know if he had succeeded or not.
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Hi Andlat, I am glad Diane has explained why she is treating Jack this way. I was wondering how long it would be before the pacifier came out. Thanks go a great chapter.
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Hi Andlat, I am glad Diane has explained why she is treating Jack this way. I was wondering how long it would be before the pacifier came out. Thanks go a great chapter.
Glad you're enjoying it! I figured that poor Jack has been in the dark for long enough. It's not like he can really do anything to dissuade his mom now that she's taken him this far.
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Yeah, now that she is making him her little boy again I imagine he will have a very hard time growing up again.
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Thanks for this latest installment. I found the power-play with the pacifier to be excruciatingly hot, and I loved learning more about Mom's motivation. One question: she tells Jack she wants him to be a good boy. But ultimately she wants him to be her little girl, yes? I sure hope so.
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I am intrigued with the idea that Diane is using the little girl theme to convince Jack that he really would rather be a little boy.
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Plateguy & PervScenes11 - I totally get your confusion over whether Diane is trying to make Jack be a good little boy or a good little girl. A lot of that arises from the fact that I'm trying to keep the reader in Jack's shoes, since I suspect that's probably where a lot of us would want to be in this sort of scenario. :) Personally, I like stories where a bad boy gets turned into a good little boy and stories where he's a good little girl, so there will be some tug back and forth in my story, even as the story moves forward. Of course, you also shouldn't discount the fact that, while I have the big picture in mind, the way the story unfolds does change as it goes from my mental image to what's actually on the page.
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You've got me hooked on many aspects of the story. Whether you believe Diane is trying to make him a good little boy or girl, I expect that the suitcase with "his" clothes does not contain any garments Jack is familiar with. Also, I realize that the story to this point only encompasses one day but wetting may be the least of Jack's problems before long. "wink, wink". That should be the icing on the cake to accelerating his regression. I don't remember Betty's story rules in this regard so I may be overstepping the bounds here and if I am, my apologies.
Overall, given the nature of the nursery I would expect we will end up with a good little girl but that is at the author's discretion. Like the others I can't wait for the next chapter. That being said, I realize that writing is work and you produce excellent work. Please stick to your own pace and we will be waiting here for the fruits of your efforts.
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Agreed. This is an excellent story. Happy to get more of it whenever we do, and no matter which way the regression goes (though I'm hoping for little girl!). Thank you!
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Looking forward to more of this great story and to see how Jessie’s role changes as her twin regresses.
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I want to thank everyone for their patience as you eagerly await the next chapter. In truth, I've hit a tiny snag that's delaying the latest installment. I have the ending of the chapter firmly in place, but I'm running into a wall when it comes to how to fill the rest of the chapter so that it's not just an abrupt leap forward that leaves heads spinning. My hope is to have it all sorted out by the end of 2018, but that's drawing awfully close.
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Still a few hours before I enter 2019, so I made my self-imposed deadline!
Jack eyed his discarded pajamas just out of reach as his mom dug in the pink and white dresser nearby. He felt what had to be a hundred butterflies in his stomach. What was she going to pull out? He had a sneaking suspicion that she would return with a nightgown and probably one more feminine than any Jessie had worn.
“Mom?” Jessie asked, stepping into the room. She smiled at Jack sitting on the edge of the changing table. It was somehow more embarrassing for her to see him in just a diaper than it had been when he had worn a dress, although he could not exactly say why that was. “Can I make some popcorn?” Only then did Jack realize that he still had the pacifier in his mouth. He reached up to pull it out, but stopped when he realized that his mom would not be happy if he did. He looked away from his sister, his blush reaching down to his bare shoulders.
“Of course. I’ll be out there in just a few minutes. Just gotta get Jack situated.” Jessie tittered as Diane pulled out a baby blue nightgown with bubble sleeves and a lacy collar.
“Looks perfect. I think I had one just like it.” She said, turning to leave the bedroom. “Good night, baby brother.” She called over her shoulder with a wicked smirk that their mom somehow missed.
“Mom, do I really have to wear” he nodded to the nightgown in her hands.
“A nightgown?” She gathered it in her hands to pull over his head. “Compared to the dress you were wearing, this is more like a long shirt, don’t you think?” He simply shrugged. “Arms up. Really, objecting to a plain nightie, but not the diapers you’ve been in all day. Honestly, your priorities are all out of whack.”
“Just keep Jessie out of here.” He muttered, bashfully raising his arms.
“Once you’re in bed, she won’t come in until morning.” His mom promised. Helping him down from the changing table, she held his hand as she led him over to the crib, the nightgown’s lace hem brushing his legs with each waddling step.
“Can I have the side down at least?” He asked. “It feels like I’m trapped in there otherwise.”
“Why would you need the side down?” She asked. He could not think of an explanation, so he sighed resignedly and remained silent. He cringed all the same as his mom raised the side of the crib, locking him inside. He knew that, were he not in the absurdly thick, fat diaper that pressed constantly against his thighs, he might have been able to climb over the side, but he did not want to try his mother’s patience. For the moment, it was better to simply behave. “Sweet dreams, Jack. We’ll try to get you out of diapers tomorrow, okay?” He nodded, the pacifier still in his mouth. He would spit it out the moment she left him, he resolved.
Walking to the door, she turned off the light, leaving Jack in the darkness, save for the soft pink-white glow of a nightlight near the changing table. The rain still falling lightly outside blocked any light in the night sky. The darkness in the room seemed to press in and Jack felt almost grateful for the nightlight’s gentle glow that held it at bay. Jack had been afraid of the dark when he had been young. Maybe this treatment was rekindling that fear. He could not say for sure. He rolled onto his side but could not get comfortable. He had no way to know for certain, but he at least strongly suspected that, back home, he would not be going to bed for another few hours. Of course, he knew that it was the diaper more than anything else that was keeping him awake.
Jack returned to lying on his back, staring up at the barely visible mobile overhead. It remained stationary. Remembering his resolution, he spit out the pacifier and it rolled onto the pillow next to his cheek. Shifting slightly, he found a more comfortable position. Now he just had to fall asleep, but that was more easily said than done.
Trying to figure out just how he had fallen so far in a day still made his head spin. Had his mom drugged him or something? That did not seem like her. Being honest to himself, he could not deny that he had had some close calls recently. Jessie had not been as far from the truth as he had claimed with the incident with Mrs. Axworthy.
Despite being roughly the same age as Jack and Jessie’s mother, Mrs. Axworthy had old-fashioned ideas. She did not allow anyone to use the restroom outside of designated breaks, regardless of how politely they asked or how urgent they deemed the situation. Her argument was that young ladies and gentlemen such as them should be more than able to hold it. In the vast majority of cases, she was correct, but Jack sometimes forgot to take full advantage of the breaks. His attempts to skirt her restroom rule only added to her belief that he was rapidly becoming a bad influence on the other students.
“And of course, Jessie’s a little goody-goody.” He muttered. He was convinced that just about every aspect of his life would be improved if his sister was not the constant presence she was.
* * *
The early morning sun drew Jack from a slumber he did not remember falling into. He immediately realized that the pacifier was back in his mouth. Not only that, but the doll he had played with the evening before now lay nearby. He suspected that his mother had sneaked in while he was asleep, but feared that it might have been his sister.
Turning the doll’s face away from him and spitting out the pacifier, Jack pushed the blanket off of him. Grimacing at the soft cotton nightgown he still wore, he none too gently yanked it up to investigate the diaper. His bladder ached, so he couldn’t have wet the bed, right? He felt a swell of pride as, slipping his hand into the plastic panties, it rested on a dry diaper. He could not help but beam, but his smile faded as he realized that he might end up wetting it if he did not get out of the crib and soon.
Grabbing the bars of the crib, he slowly got to his feet. Examining it closely, he realized he could probably make it over without too much trouble. He grimaced at his reflection in the mirror across the room, a brown-haired boy in a light blue nightgown. He adjusted the nightgown to at least cover his diaper again, but the reflection could only be improved so much in his current situation. He made an ugly face at himself, which made him feel a bit better.
“Now to climb this thing” Jack had climbed countless trees in his life. For some reason, Jessie had always struggled with it, but he had excelled. Jessie had always been more balanced than him, as their brief stint in gymnastics had demonstrated, but he was just plain better at climbing trees. He made short work of getting to the top of the wall of the crib, but just as he was shifting his weight to slide down the exterior, a latch released and the entire wall came down with a crash! He rolled along the carpeted floor, diaper fully exposed. Although a short spurt of urine escaped into its cottony confines, he thankfully kept most of it in.
The door flew open and his mother looked down at the disheveled boy on the plush carpet. She simply shook her head. There was too much to do this morning to even begin to understand what had transpired a moment ago.
“Good, you’re up.” She said. “Apparently, the neighbors are coming by for a visit and we need to get you ready.”
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Thanks for this latest installment. I sure hope his Mom gets around to punishing him for climbing out of his crib! Can't wait to see where and how far this goes.
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Nice installment. Good to see Jessie is recognizing that Jack really is her baby brother now. Should be interesting to see how Jack responds to the neighbors coming over.
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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.
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Or so he thinks! Tee, hee, hee.
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First of all, thank you for this wonderful story. As I might have mentioned earlier, the story follows almost exactly a favorite fantasy of mine and I appreciate you continuing to produce great writing.
I have to agree that Diane has been mighty unreliable in keeping her word and Jack's skepticism in the bathroom was well warranted. Very curious to see how Jack is further "entrapped" in sissy babyhood. After all, Jack and family will be at the cabin for a week. Unless the neighbors leave, how will Jack go back to his regular life while at the cabin. Also looking forward to knowing more about the neighbor kids. Wonder how their and their parents roles will emerge and interact with Jack, Jessie and Diane. Jack and family are only in the first full day of a week long vacation so anything can happen.
I was surprised that Diane claimed that Jack was small enough to disguise as a baby girl. Even if small for his age, I doubt any adult could mistake Jack for a baby or toddler. Same would go for Kyle's awareness, if he's Jack's and Jessie's age. That can't bode well for Jack. I'm hanging on the cliff for the next installment.
Many thanks, again.
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Merci tout le monde for reading and commenting!
Babycakes, you caught me! I've been playing fast and loose with Jack's size this entire time! I can assure you, however, that it will all be explained in time and just adds further impetus for Jack to cooperate and behave. I dropped some hints about what's to come for Jack during the neighbors' visit and Kyle may be the least of Jack's worries. It's possible that it will occur to Jack that being a baby girl at the first visit and a 12 year old boy at the second visit will create some problems, but he's not really one to think about consequences, now is he?
DaraJaney, you've written so many stories along these same lines that I know I have little hope of pulling the wool over your eyes. As has been the case throughout this entire story, Jack may find some obstacles between him and maturity.
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Last chapter might be the best yet.
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.
Delicious. I love how you describe how he ends up before describing how he gets there, and leaving out a lot of the middle to tease our imaginations about what precisely, beyond the already obvious, left him so pouty.
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Last chapter might be the best yet.
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.
Delicious. I love how you describe how he ends up before describing how he gets there, and leaving out a lot of the middle to tease our imaginations about what precisely, beyond the already obvious, left him so pouty.
My hope is that, once the next chapter's out, everyone enjoys this last chapter even more, since we've officially moved into the main story as we meet the neighbors who will play key roles in what's to come. Of course, for that to happen, I need to post the next chapter, so I had better return to writing, shouldn't I? Thanks so much for reading!
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This story is amazing, love it - thankyou Andlat :-)
Not sure why but most of my absolute all time favourite stories have 'real boy' involvement if that makes sense (sisters boyfriend or mums boyfriend or a boy that makes friends with Jack/Jackie) do you think that will happen in this story?
Not even sexual just friendship/teasing from a 'real boy'.
(my female curiosity asking hope you dont mind!)
Philipa x
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This story is amazing, love it - thankyou Andlat :-)
Not sure why but most of my absolute all time favourite stories have 'real boy' involvement if that makes sense (sisters boyfriend or mums boyfriend or a boy that makes friends with Jack/Jackie) do you think that will happen in this story?
Not even sexual just friendship/teasing from a 'real boy'.
(my female curiosity asking hope you dont mind!)
Philipa x
I don't want to give too much away at this point, but I can confirm that the neighbors have a role to play in the story as we move forward. It'll become more clear in the next part or two.
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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.
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I sure would not mind if he gets to be a flower girl at some point. :)
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Excellent chapter Andlat! Our protagonist goes from thickly diapered baby girl as part of his punishment to 12 (almost 13) year old boy in his own clothes in one chapter (jammies aside). Amazing. This is the most realistic sissybaby/petticoating punishment scenario I've ever seen described. Jack is actually able to earn his way back to his proper age, though we don't know if he will squander it going forward ;) and Mom actually keeps her promise and does not sadistically come up with limitless excuses to extend his infantilization.
You also opened a lot of interesting possibilities with further description of the neighbors. Is Michael a single Dad? Is there romance in the future for Diane? Does Jessie end up in a babysitting role? Can Jack stay dry in the bottom bunk his first night out of diapers? And, most importantly, what other "life changing" events, to quote Denise, will befall Jack and is he joined in his punishment by Kyle?
Can't wait to find out. Many, many thanks for relating this wonderful story.
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Hope not dry night then back into diaper onesie baby dress
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Sissykimmy1 - I love the idea of boys as flower girls, so it's certainly possible! Maybe Jack and Caitlyn can both be the flower girls for a wedding!
Moms.cross.dresser - You'll just have to wait and see, but I think it'd be wrong to think that Jack will stay out of diapers forever.
Babycakes - Thanks so much! I felt like it was a bit of a risk to have Jack return to his clothes, but I personally think it's more fun to have Jack's journey be more tumultuous than a simple, straight descent. In the next part, you'll see that clothes don't always make the man, as it were, and Jack might find it difficult to assume his old role despite being in "normal" clothes again.
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The next morning, Jack could not believe how well he had slept and secretly, he was thrilled that he had woken up dry, even as he dashed to the bathroom to empty his loudly complaining bladder.
“Bit of an emergency?” Jessie asked, making her bed when he came back.
“Shuddup.” He muttered.
“Did you stay dry, Jack?” Diane asked, walking into the room.
“He did.” Jessie said before Jack could even think to respond.
“Attaboy!” He could not believe how genuinely proud both his mom and his sister seemed of him. It actually brought a glimmer of a smile to his face. “Michael’s invited us over to their cabin today, kids, so get dressed so we can eat a quick breakfast.” Jack felt that she left a lot unsaid, but he was too embarrassed by the idea of asking to even bring it up. How would they react to seeing him in a completely different outfit? Maybe they would not even realize. He hoped against hope that that would be the case.
Sure enough, they ate breakfast quickly and then set out for the neighbors’. It was a beautiful summer morning and Jack, though he hid it, still delighted in being able to walk without waddling.
When they arrived, Kyle and Caitlyn were still eating breakfast. Caitlyn excitedly waved at Jack and Kyle vaguely smiled at Jessie, still basically ignoring Jack.
“Sorry.” Michael said. “The kiddos had a bit of a slow start this morning, but at least they’re dressed.” He chuckled.
“Yeah, I know the feeling. I actually didn’t have to drag Jack out of bed this morning. It was a miracle.”
Jack slowly snuck closer to Kyle, trying to figure out how best to break the ice as it were with him. Standing next to him, he realized that the boy, despite being the same age as him, was taller even than Jessie. He had to be at least three inches taller than Jack and Jack felt his nerve shrink as he realized he was afraid of the bigger boy.
He realized how ridiculous it seemed. He would have never been afraid of someone his own age before. Somehow, the events of the last couple days had made him into some sort of coward.
“I was thinking we’d go upstairs to my room and play some video games.” Kyle said to Jessie, unconsciously stepping away from the suddenly bashful Jack.
“That sounds fun. I always beat Jack, so I’d like a challenge for once.” Jack rolled his eyes. Jessie won just barely over half the time and she usually resorted to cheap tricks like tickling him to ensure her victory.
Even though no one said anything, Jack knew that everyone had connected the dots and realized that he was the baby girl in the playpen the day before. He figured he could play it off as a punishment and get Kyle to understand, but when he tried to follow Kyle and Jessie, Jessie looked back at him.
“Jack, why don’t you go play with Caitlyn? We don’t need you hanging around with us.” Jack looked beseechingly at Kyle.
“That seems fair.” Kyle said. “I know you’re older than Caitlyn, but I think pairs works best. Older kids.” He gestured to himself and Jessie. “And younger kids.”
“What? I’m the same age as Jessie!” Kyle looked surprised by this.
“He’s lying.” Jessie said at once. Jack’s eyes widened and his face fell as he saw that Kyle seemed to believe her at once. He knew he looked younger than the other boy, but this was ridiculous!
“But” Jessie gave him a look so much like their mom’s that he fell silent.
“Go play with Caitlyn.” Jessie ordered. “Little brothers.” She muttered as they disappeared upstairs. Caitlyn immediately grabbed Jack’s hand.
“C’mon, Jack! Let’s go play in my room. I know you like girl stuff, so” She tugged him along, amazing Jack with her strength.
Caitlyn’s room looked exactly like what Jack expected it to. She had a Pretty Ponies of Periwinkle Park bedspread and even had the vast majority of the dolls, in addition to a few Barbies and other dolls.
“What game do you want to play, Jack?” She asked, doing her best to be a gracious host. He shrugged. “We can just each pick a doll and play mommies?”
“Couldn’t we play something else? You have some board games, don’t you?”
“I have Barbie checkers! My grandma bought it for me for my birthday!” She excitedly grabbed the box. “But we both have to pick out a doll anyway to sit in our laps.” Jack shrugged and nodded.
“Fine.”
“Which one do you want?” Jack looked around the room, trying to pick the least embarrassing doll he could. He quickly realized just how limited his options were and he grabbed one of the ponies, figuring that they would be better than a human doll. “Is that your favorite pony? I love Sterling Sprinkles!”
“She’s okay.” Jack said with a shrug. Jessie had been almost aggressively into the Pretty Ponies when they had been younger and, in truth, if Jack had been forced to pick a favorite pony, it would probably have been Sterling Sprinkles. Her sky blue coat and silver mane were the closest to a masculine pony, at least compared to the other main characters.
“I’m going to pick Petite Belle!” Caitlyn said, picking up the pony. “Oui, oui! That’s her catchphrase.”
“I know.” Jack did know that, much to his chagrin.
“Ready to play checkers?” Jack nodded, but he wondered if he should let Caitlyn win or try his best to win.
After the first three games, however, he realized just how outclassed he was by the little girl and he gave up any pretension about ‘letting’ her win. He successfully won both the fourth and fifth games, but the sixth went to Caitlyn.
“Four to two.” Caitlyn said with a giggle. “I guess Petite Belle is better at checkers than Sterling Sprinkles, hmm?”
“Yeah” Jack grunted. “I’ll win the next game.”
“Oh? Wanna make a bet?”
“Not really.” Jack said, a hint of nervousness sneaking into his voice. Caitlyn’s grin unsettled him every bit as much as the smile Jessie had whenever she thought of some nefarious scheme that Jack would end up not enjoying. “Let’s play something else.”
“Like what?”
“How about we go outside?” Jack suggested, hoping to get out of this girly bedroom. He knew that the nursery back at his cabin was far worse, but he could choose to leave this bedroom, at least.
“Wanna play tag?” Caitlyn suggested. Jack, figuring that he could win that game pretty easily, readily agreed.
“How about we ask Jessie and Kyle to join us?”
“Naw, they’re probably playing video games in his room.” Caitlyn said. “We’ll have fun without them!” Jack was not so sure, but Caitlyn had made up her mind. “Take your dolly with you!” She said, picking up Petite Belle and waiting expectantly for Jack to follow suit. He hesitantly rose, trying to find the happy medium between reluctantly carrying the pony in his hands and showing enough care not to draw Caitlyn’s ire. Satisfied, Caitlyn led him out of her room.
“We’re going to go play outside.” Caitlyn declared as they passed by Michael and Diane. Diane noticed the pony doll in Jack’s hands and smiled.
“What’s the rule for playing outside, Caitlyn?” Michael asked.
“Keep the cabin in sight.” Caitlyn replied dutifully. “Don’t go in the woods.”
“That’s right.” Michael said. “And that goes for you too, Jack.” Jack nodded, but his mom had other thoughts.
“Jack, what’s the rule?”
“Keep the cabin in sight and don’t go in the woods.” Jack replied.
“Attaboy.” Diane said with a smile. “If anything happens, you better believe that I won’t be happy.”
“I’ll keep an eye on Jack, Miss Diane.” Caitlyn said. “We’re just going to be playing with our dolls.” Diane could not help but giggle.
“I appreciate that Caitlyn. If Jack does anything naughty, you be sure to tell me, okay?”
“Oh, yes!”
“But” Michael added. “That doesn’t mean you need to be little miss tattletale, okay?”
“Oh,” Diane said with a Jessie-like twinkle in her eye. “Jack’s pretty good at being little miss tattletale too. Aren’t you, Jack?” He could tell she was just trying to embarrass him, so he simply nodded and held back his words.
“It’ll be time for lunch in a little bit, so we’ll call you when it’s ready.” Michael said. “Have fun!” Jack followed Caitlyn, hoping that whatever plans she had for playing outside would not be too embarrassing.
“What do we do now?” Jack asked, hoping to devise some way to get rid of the sky blue pony doll in his arms.
“We’re going to pretend that our ponies drank from the Fountain of Bellerophon!” Caitlyn exclaimed. Seeing Jack’s confused expression, she sighed and explained. “That means that they’re able to fly! Duh!”
“Oh.”
“Like this.” Caitlyn demonstrated, making Petite Belle swoop and soar around her head. Jack halfheartedly mimicked her, but he could not help but have fun, running around the yard, the sun shining down on his smiling face.
Before either of them knew it, Michael called them in for lunch. How long had they spent running around, giggling? Jack could not say. He stepped inside the cabin, but did not see his mom anywhere. There was just two places set at the table.
“Sit down, kiddos. We’re going to get you two out of the way before the bigger kids come down.”
Jack stared down at the food in front of him. Just like Caitlyn, he had a peanut butter and jelly sandwich cut in half and a little pink cup filled with juice. It seemed like a childish lunch even for a six year old, let alone an almost teenager.
“If you want seconds, you just have to ask.” Michael said with a smile.
“Where’d my mom go?”
“Oh, she ran back to your cabin for a moment, I think.” Michael replied. “She wanted to show me some photos from a trip you all took last year.” He gestured for Jack to start eating. Caitlyn, across the table, was tearing into her lunch like a wild animal.
Jack had never really liked peanut butter and jelly, so he mostly nibbled at it, wishing that he could have anything other than this. He had a suspicion that Jessie and Kyle would get something else for their lunch and he once again bemoaned the fact that he had somehow gotten stuck as Caitlyn’s playmate.
“Did you two have fun outside?”
“Yeah, Daddy!” Caitlyn exclaimed, her mouth full. “Jack and I are princesses now!” Michael chuckled.
“Well, you’re Daddy’s little princess, that’s for sure, and I bet Jack is his mommy’s little prince, maybe not a princess.” Caitlyn considered this and shrugged.
Once they finished eating, Jack tried to get up, but Michael gently touched his shoulder. With a washcloth, he wiped Jack’s face and then nodded.
“Now you can get up. I still wipe Kyle’s face too, so no need to be so embarrassed.” He also wiped Caitlyn’s face, smiling at them both. “Go ahead and play in Caitlyn’s room again. I’m going to feed the other two and then I’ll be in there to get you down for your nap.” Caitlyn groaned and stomped off with Jack following. If Caitlyn would be napping soon, that meant he would be able to slip away and join Kyle and Jessie! His heart fluttered with excitement.
Back in the room, Caitlyn insisted that they sit back on the floor and pretend that their ponies were talking to each other. Jack did his best to play along, but he felt a bit silly whenever Caitlyn would scold him and make him answer the questions ‘right’.
“Alright, Caitlyn Marie. Naptime.” Michael said, poking his head into the room and giving Jack a brief escape from the ponies’ conversation.
“But Daddy!”
“But nothing. You’re taking a nap. You too, Jack.”
“What? I don’t need a nap!”
“The more you argue, the more you prove you do.” Michael said.
“But” Michael gave him a stern look and his voice tapered off.
“Caitlyn, how about you explain to Jack what happens to kids who talk back in this house?”
“They get spanked.” She said seriously. “Even Kyle gets spanked and he’s nearly thirteen.”
“So am I!” Jack looked from Caitlyn to Michael in a panic.
“Nuh-uh!” Caitlyn said.
“Regardless of anything,” Michael said. “You two are going down for a nap in five minutes.” He could see the defiance still in Jack’s eyes. “Jack, you can either obey or I can explain to your mom that you’re misbehaving. I think we both know what’ll happen after that.” Jack gulped and nodded. “Alright, Caitlyn, change into your jammies. Jack, we’ll figure something out for you.” Without even a second’s hesitation, Caitlyn undressed down to her cami and Disney princess panties before pulling on a Frozen pajama set. Jack remained on the floor, anxious about just what Michael would ‘figure out’ for him.
He returned a moment later with a pair of surprisingly innocuous gym shorts in his hands. He smiled at Jack’s look of astonishment.
“Kyle doesn’t wear pajamas anymore, but your mommy said that these would work.” Michael explained.
“So everyone knows I’m taking a nap?”
“Well, yeah. Why wouldn’t they?” Jack huffed at that
“Where can I change?” He asked, trying to not sound as annoyed as he felt.
“Right here.” Jack started to question it, but realized that it was one fight he would not win. He unzipped his shorts and pulled them down. Caitlyn’s eyes widened and began to fill with questions as she saw his forest green boxer briefs.
“Caitlyn, why don’t you get into bed? Jack will join you in just a second.” Michael suggested, noticing his daughter’s expression. “Oh, and by the way, Jack.” Jack stopped tugging the gym shorts up his legs. “Your mommy says you should be fine without any bedtime protection for your nap, but she was a little concerned that you didn’t bring it up yourself.” Jack felt as white as a sheet. “I know it’s embarrassing, but don’t be shy.
Neither Caitlyn nor I will tease you. Isn’t that right, Caitlyn?” The six year old nodded firmly. “Alright, let’s get you into bed for your nap. After that, you two can go swimming, hmm?” In short order, Jack found himself tucked into Caitlyn’s bed right next to her, each of them hugging their respective pony doll. “Sweet dreams.” Michael said, closing the door gently behind him.
“Hey, Jack?” Caitlyn whispered.
“Yeah?”
“Why are you dressed like a boy today?”
“Cuz I am a boy.” Jack mumbled.
“But yesterday” He quickly cut her off.
“That was just my mom punishing me.”
“Oh.” Caitlyn fell silent before pensively adding “Is it mean of me to want you to be punished again?”
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Hahaha I really like the way that you are transforming jack in little Jackie hehehe me too want to jack to be punished maybe a wet bed after his nap ! But I think he deserves to be treated like a baby prince heheheh and catlyin would love to help to change his nappys hehe
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Hahaha I really like the way that you are transforming jack in little Jackie hehehe me too want to jack to be punished maybe a wet bed after his nap ! But I think he deserves to be treated like a baby prince heheheh and catlyin would love to help to change his nappys hehe
I'm glad you're enjoying it! Jack may not realize it now, but I think he should appreciate that he has at least one new friend who will support him even if he finds himself back in diapers and dresses.
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Really creative chapter, putting him an embarrassing, sissy type role while still in his boy's clothes.
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Thanks so much for this latest chapter. Generally, I'm not usually into the whole "dominated by younger kid" trope, and initially I was sad to see that getting so much airtime here. But the way you convey Jack's social demotion here is so scorchingly hot. Not sure why, but Jack being fed separately because he's a little kid was so deliciously humiliating. Ditto with his fear of the older boy and his rejection from that boy and his older sister. Read this this morning and have been thinking about it all day. Thank you so much! (Now, if only the adult man had not corrected the "princess" comment about Jack!)
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Sissykimmy1 - I wasn't really sure how much mileage I could get out of Jack being not in sissy things, so I'm glad you're enjoying it!
Pervscenes11 - I've taken a few risks with this chapter, so I'm glad you liked it even if it wasn't really your cup of tea.
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I loved it! You're getting something across really subtly but clearly: everyone sees Jack, status-wise, as a very young girl. It's only Jack that doesn't get it. It's so hot.
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Pervscenes11 - Well, they had to pair up somehow. It wouldn't be fair for Caitlyn to have to play alone while Jack, Jessie, and Kyle were all hanging out upstairs together. Really, it was generous of Jack to "volunteer" to play with Caitlyn.
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Jack is in a road to babyhood heheh in the last chapter when we see he been treated like a little kid I think that is a setup to downgrade jack so we can get along that he’s been transform in a baby in the end of the road, now I think he gonna wet in his nap and after this I think he gonna be put in diaper, here I really hope that the author make a way that Michael have some pampers disposable diapers in his cabin and put jack in them I can only imagine the embarrassment for jack to use diapers meant for a toddler, this could cement his road to babyhood hhehe, keep the good work and please use my suggestion heheh
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Considering how logical and true to her word his mother has been so far, I'm honestly surprised she's contributed to pushing him back into the little sissy role.
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As always, your writing is excellent. Thanks for continuing the story. That said, I have to admit to a bit of confusion.
First, I'm confused about Jack's height and the role it plays in the situation he's placed in at the neighbor's house. In response to one of my earlier comments you said, "I've been playing fast and loose with Jack's size this entire time! I can assure you, however, that it will all be explained in time and just adds further impetus for Jack to cooperate and behave." Then, in this most recent chapter, Jack describes Kyle as, "...despite being the same age as him, was taller even than Jessie. He stood at least a head and a half taller than Jack and Jack felt his nerve shrink as he realized he was afraid of the bigger boy." Yet, much earlier in the story Jessie was described as being only "a tiny bit taller than him [Jack]..." Given general statistics, the average male 12 y.o. is 61.5" (156.2 cm) and a "head and a half" would equate to about 12" - 15" meaning Jack is about 49" or less. But since Jessie is only a tiny bit taller than Jack why would Kyle not believe that Jack and Jessie are the same age. If I'm on track about Jack's height then it could be logical that he would be paired with Caitlyn, especially if she's big for her age and especially given Jack's punishment as a baby girl when they last met.
Second, could you be dropping hints that Kyle is treated younger than his age at times either as a punishment or just to keep him in line (e.g., "I still wipe Kyle’s face too, so no need to be so embarrassed”)? Certainly, if that's true, Kyle would not want to be associated with Jack and attract a similar punishment so age is just a ruse to distance himself from Jack.
Third, why is Diane so willing to let the neighbors think of Jack as much younger than Jessie and his true age and enforcing a feminine view of him, calling him a "tattletale princess" when he is dressed as a normal near-teen and we have no indication of him exhibiting any bad behavior. I think earlier comments that Diane can't be trusted are coming true.
Finally, why is Michael so accepting of Diane's treatment of Jack?
As I've said before, sorry to run on but I love this story and it's the realism and your excellent storytelling that keep me coming back for more.
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As always, your writing is excellent. Thanks for continuing the story. That said, I have to admit to a bit of confusion.
First, I'm confused about Jack's height and the role it plays in the situation he's placed in at the neighbor's house. In response to one of my earlier comments you said, "I've been playing fast and loose with Jack's size this entire time! I can assure you, however, that it will all be explained in time and just adds further impetus for Jack to cooperate and behave." Then, in this most recent chapter, Jack describes Kyle as, "...despite being the same age as him, was taller even than Jessie. He stood at least a head and a half taller than Jack and Jack felt his nerve shrink as he realized he was afraid of the bigger boy." Yet, much earlier in the story Jessie was described as being only "a tiny bit taller than him [Jack]..." Given general statistics, the average male 12 y.o. is 61.5" (156.2 cm) and a "head and a half" would equate to about 12" - 15" meaning Jack is about 49" or less. But since Jessie is only a tiny bit taller than Jack why would Kyle not believe that Jack and Jessie are the same age. If I'm on track about Jack's height then it could be logical that he would be paired with Caitlyn, especially if she's big for her age and especially given Jack's punishment as a baby girl when they last met.
Second, could you be dropping hints that Kyle is treated younger than his age at times either as a punishment or just to keep him in line (e.g., "I still wipe Kyle’s face too, so no need to be so embarrassed”)? Certainly, if that's true, Kyle would not want to be associated with Jack and attract a similar punishment so age is just a ruse to distance himself from Jack.
Third, why is Diane so willing to let the neighbors think of Jack as much younger than Jessie and his true age and enforcing a feminine view of him, calling him a "tattletale princess" when he is dressed as a normal near-teen and we have no indication of him exhibiting any bad behavior. I think earlier comments that Diane can't be trusted are coming true.
Finally, why is Michael so accepting of Diane's treatment of Jack?
As I've said before, sorry to run on but I love this story and it's the realism and your excellent storytelling that keep me coming back for more.
I think with a lot of this, you're asking the right questions. All will be answered in time. I was planning on posting the next part today, but with your question about the heights, it's pretty clear that I need to take some extra time and make sure I'm remaining consistent. I may go back and change some details to make the heights make a bit more sense.
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My apologies to you and all your other fans for causing a delay in the release of a new chapter. But thanks for listening abd caring.
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My apologies to you and all your other fans for causing a delay in the release of a new chapter. But thanks for listening abd caring.
Oh, it wasn't much of a bother. I was able to edit one part of the story, but being a bit more clear about Jessie's height was at too early a part of the story for me to edit it anymore on here. It's edited in the master copy though. :) Kyle is "at least" three inches taller than Jack, and Jessie is about an inch taller than him. I should be clear, however, that Kyle has his reasons for keeping his distance from Jack, so that's to blame more than anything else for him "believing" that Jack is Jessie's little brother. Plus, there was the whole baby Jackie incident. Anyway, down below everyone should see the newest chapter shortly! Jack's going swimming!
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“I didn’t bring anything to swim in.” Jack said as he returned from the bathroom. It had only been about an hour since he and Caitlyn had been put to bed for their nap, but he had needed to go badly. “I could run back to my cabin.”
“Don’t worry about it. I think we have an old swimsuit of Kyle’s around here that should fit you.” Michael said. “Why don’t you come with me and we’ll go ask him?” Jack could not see the harm in that, so he agreed. “Caitlyn, get changed into your swimsuit while Jack and I go find him something.”
Jack followed Michael upstairs to Kyle’s room, remaining silent as Michael asked Kyle if he had a swimsuit that Jack could borrow. The glimpse he got of Kyle’s room filled him with jealousy. It looked so much like his room back home that he could not help but feel cheated that he had spent the entire day so far in Caitlyn’s little girl room.
“Caitlyn didn’t have one he could borrow?” Jessie teased. Jack glared at her.
“He’s a bit too big for Caitlyn’s swimsuits, Jessie.” Michael said with a smile. Jack’s ears burned. That was not the only reason for him to not wear one of hers! “Plus, they’re not really your style, right?” Jack bashfully nodded, causing Michael to chuckle.
“Here, he can wear these.” Kyle said, handing Michael a pair of Spider-Man swim trunks.
“Thanks, Kyle.” Jack said immediately, eager to break the ice. He knew that Kyle was his age, but he was having trouble remembering that. There was just something about Kyle that made him seem older, more mature.
“Why do you still have these?” Michael asked, holding them up. “They can’t possibly fit you anymore!”
“I left them here a couple years ago.” Kyle replied with a shrug. “If they’re too small for Jack, he can borrow my other pair.”
“Or I can run back to my cabin.” Jack said, trying to sound as helpful as he could.
“We’ll try these first, Jack.” Michael said gently. “But it’s very nice of you to offer.” He closed Kyle’s door and pointed across the hall. “Why don’t you pop in there and put them on?” Taking the Spider-Man swim trunks, Jack disappeared into the bathroom and quickly pulled them on.
He glanced at himself in the mirror and sighed. He had always looked younger than he was, but seeing Kyle reminded him a bit too much of just how young he looked for his age. The juvenile swim trunks definitely did not help.
In a word, they were small. They barely covered more skin than his underwear and they were nearly as tight. It must have been more like four years or so since they had fit Kyle. Maybe he could lie and tell Michael that they did not fit? Then he could run back to his cabin and get his. They were hanging on the railing of the porch from the night before, after all. It would not be a big deal at all.
“Everything okay in here?” Michael asked as he opened the door. “Oh, those should work perfectly.”
“Um”
“I know, they’re a little snug, but it’ll just remind you to bring your own trunks next time.” Michael said with a chuckle. “Besides, you’ve worn worse the last couple days, huh?” He saw Jack’s ears go red and figured that that was reply enough.
Caitlyn was wearing a yellow and blue one piece swimsuit, bouncing up and down eagerly. She seemed a bit disappointed to see Jack in boy’s swim trunks, but she still ran over to hug him.
“Are you excited to swim?” She asked.
“Yeah.”
“Let’s grab you two some towels first.” Michael said. “I think I might even have a Spider-Man beach towel somewhere.” At first, Jack was embarrassed, but then he realized that it could be worse, so he feigned a smile. “You’ve taken swim lessons, Jack?”
“No, but I know how to swim.”
“Ah.” Michael said as he handed him the promised beach towel. “Caitlyn isn’t a certified swimmer yet either, so I’ll need both of you to stay pretty shallow.” Jack nodded grimly. He should have known that there would be something that would keep him from really enjoying this. He tugged on the leg of his swim trunks, wishing that they would go longer than they did. “Alright, I think we’re all set!”
“I’m back!” Diane called, stepping into the cabin. She saw Jack and Caitlyn’s attire. “Going swimming?”
“We are!” Caitlyn bounced again.
“And did you have a nice nap?” Diane looked at Jack expectantly.
“Yeah.” Jack muttered.
“We’re going down to the lake if you want to join us. Might be easier to have two sets of eyes on these two.” Michael said with a chuckle. Diane set her bag down by the dining room table and nodded. She gave Jack a look that said he would need to be on his absolute best behavior.
“Race you to the lake!” Caitlyn said, charging toward it the second they crossed the threshold to the porch. Jack quickly gave chase, the tightness of his trunks on his thighs hindering him to a certain degree. “Last one there’s a rotten egg!” Caitlyn yelled, looking over her shoulder.
“It’s a tie!” Diane called as they reached the shore of the lake. Caitlyn and Jack looked at each other with a smile on their faces. Neither of them had paid enough attention to really see who had won, so they accepted the result amiably.
“Can we go swimming now, Daddy?”
“Sunscreen and water wings first, princess.”
“You too, Jack.” Diane said. “Sunscreen and water wings for both of you.” She saw Jack’s eyes widen. “What do you think, Michael? Can Jack go without water wings?”
“He told me he’s never had swimming lessons, so it might be a good idea. I have two pairs, so it wouldn’t be an inconvenience.”
“Come here, Jack, and let me get sunscreen on you.” Diane said, rubbing it all over her son’s back and chest.
“Mom, please.” Jack whispered, eyeing the bright pink water wings with clear dismay. Caitlyn had gotten the yellow and blue pair, leaving him with these.
“Jack, it’s not that big of a deal. Just wear them for me. It’s for safety’s sake.”
“No!”
“Jack, I don’t like that tone.” She said. “A good little boy would wear them.” She could almost feel the anger rising off of him.
“But”
“Look, Caitlyn’s already in the water. Don’t you want to join her? You’ve had such fun with her today.” Jack had had enough.
“No, mom, listen! I had to play with Caitlyn all day and deal with everyone treating me like a little kid!”
“Jacob Anthony! You are embarrassing me!” Diane said through gritted teeth.
“But mom!”
“You are coming with me into the house right this second.” Michael watched Caitlyn play in the water, pretending not to notice Diane dragging Jack by the wrist into the cabin.
“Mom!”
“I have had it up to here with your attitude, mister.” She said, sitting down on the chair in the dining room she had placed her bag next to. “You’ll be receiving a spanking and then” her voice trailed off. “Well, we’ll start with the spanking.”
“Right here?”
“Yeah. As long as you don’t scream and yell, I doubt we’ll attract much attention.” Jack sighed and took his place across her lap. “It’s just a short one.” She lowered his swim trunks down to his ankles and gave his bottom an almost affectionate pat. “Only a few spanks.”
“To remind me to be a good little boy?” He asked softly.
“Well, since you’re clearly incapable of that” before she finished her thought, she quickly doled out six strikes across his slightly raised buttocks. He bit his lip trying to keep from crying out. In the silence following the spanking, he listened for the sound of Kyle’s door opening upstairs. Hearing nothing, he breathed a sigh of relief.
“Thank you for spanking me, Mommy.” He mumbled, eager to try and get back on her good side.
“Remarkable how quickly your behavior changes.” She casually pulled his swim trunks off the rest of the way. “Stand up for mommy.” He complied, feeling so strange standing completely naked in the neighbors’ kitchen. “Now, which is it? Do you not want to be a good little boy or are you incapable of it?” He remained silent, not meeting her gaze. “Michael says you’ve been mostly behaved today, only arguing about as much as Caitlyn has, but this outburst down by the lake is too much, Jack. You cannot keep behaving like this. It is embarrassing for me and I’m not sure why it doesn’t seem to bother you in the slightest.”
“Sorry.” He mumbled. “Mommy.” He added.
“Saying a few nice words isn’t going to cut it, Jack.” She looked at him. He was so capable of at least looking like he was sincerely remorseful for what he had done. “I need to make sure that you mean it.” She reached down into her bag and pulled out a pink garment. Jack’s eyes widened. It was a bright pink girls’ swimsuit with a little white bow on the chest and, most distressingly of all, a pink tutu around the waist. “I’ve given you more than enough of a chance to behave. Since you refuse to be a good little boy, you’ll be mommy’s good little girl for the rest of our visit to Michael’s cabin.”
“But” he stopped talking, knowing that he stood a good chance of just digging himself deeper.
“Or would you prefer to be Mommy’s little princess?” She asked. “No, I think Mommy’s good little girl is enough, hmm?” Jack did not answer, so she leaned forward and held out the swimsuit for him to step into. He bashfully did so. “I have to say, this fits you much better than those too-small trunks did.” Diane said. Jack remained silent. His mom reached into the bag and pulled out one last item.
“A bow?” He quickly retreated back into silence after the outburst, hoping it would not earn him further punishment.
“Caitlyn has her hair in braids, so I figured you need an accessory too.” Jack stood as still as possible, seething as she put the big pink bow on top of his head. “There, that shouldn’t fall off as long as you’re careful.” She hugged him close. “Let’s get you back outside. You’re going to put on those water wings and play with Caitlyn, do I make myself clear?”
“Yes, mommy.” Jack intoned. She patted him on the shoulder and they walked back out to the lakeshore. Jack tried without any luck to stop the tutu from bouncing with every step. It seemed to draw even more attention to the sissy boy with the grim expression.
Caitlyn, of course, was effervescent about Jack’s new attire, laughing with delight as he stoically allowed his mom to put the pink water wings on his arms. He knew that he looked ridiculous based solely on the smile his mom wore.
“Alright, all set.” She said. Jack shuffled down to the water and stepped in, a bit hesitant due to the coolness, but he also wanted to submerge at least the lower half of his humiliating swimsuit. What if Jessie and Kyle came out? He would never live this down.
“I love your new swimsuit, Jack.” Caitlyn said.
“Thanks.” He mumbled, his hands playing with the tutu. Caitlyn immediately splashed him and he had no choice but to splash back, beginning an all-out splash war.
Once their energy had faded, Caitlyn and Jack sat down in the water and simply enjoyed the day. After a bit, they were shepherded out of the water by their parents and wrapped in towels before being vigorously dried off. Jack grabbed the towel from his mom as quickly as he could, desperate to regain some semblance of agency.
Hearing the screen door of the cabin open, he quickly wrapped the towel around himself to try and conceal his feminine swimsuit from Jessie and Kyle as they emerged from the cabin, clad in their swimsuits. She wore the same black and white bikini that she had worn the evening before when she and Jack had gone swimming at their cabin. She had begged Diane for it for a whole week before she finally relented. Kyle wore a pair of brown swimming trunks with a white stripe on the side, far more appropriate for a boy his age than the pink swimsuit Jack had on under his towel. He instinctively pulled the towel tighter around him, grateful for just how enormous it was.
“Did we miss swim time?” Jessie called as they approached.
“Jack, are you done swimming?” Diane asked. He nodded.
“C’mon, Jack.” Jessie said, grinning. “We’re going to jump off the end of the dock. You love doing that!”
“She’s right, Jack.” Diane said. “Just do it once.”
“But mommy” he hissed.
“You don’t have to if you don’t want to.” Diane said.
“C’mon Jack! Just do it once! Please!” Jessie pleaded. Jack eyed her suspiciously. She must know something. With a gulp, he realized that, even though he had his swimsuit hidden, there was a giant pink bow on top of his head. Jessie had to know he had something embarrassing on! A mischievous glimmer appeared in her eye. “Bet I can jump farther out than you can.” Jack felt his competitive spirit rise, but then he reminded himself of the swimsuit he wore.
“Nuh-uh! Jack can jump a lot farther!” Caitlyn interjected. “I know he can!” With Caitlyn firmly supporting him, Jack had no choice but to drop the towel.
Desperate to own the moment, Jack did a turn so that Jessie and Kyle could see every angle of his new swimwear, water wings and all.
“Take it all in.” He said with a bit more of an edge to his voice.
“Didn’t like the Spider-Man trunks?” Jessie asked, but her voice was a bit softer. Jack had succeeded, it seemed, in seizing the upper hand. He could not help but stand a bit taller, nearly level with Jessie.
“Pink’s more my color.” Jack managed to reply even as a wave of revulsion hit him. He wondered what Kyle thought, but the other boy seemed as aloof and uninterested in Jack as ever. “So, are we going to see who can jump farther or not?” He could feel his nerve about to leave him and he had to resist the urge to pick the towel up again to hide his outfit. Resummoning his nerve, he turned and hurried to the dock. “Run the whole length and jump off?” He asked. Jessie nodded, taking her place next to her brother.
“Be safe, kids!” Michael called. Caitlyn stood next to him, nervously watching her friend and his sister.
“Kyle, can you be the judge?” Kyle simply nodded and stood far enough away from the dock so that he could easily see the distance each of them jumped.
“Who goes first?” Jack asked.
“You” Jessie said at once, stepping slightly aside so that he was alone on the dock. He readied himself, determined to beat Jessie, no matter what it took. “Wait!” Jessie yelled, breaking his focus. “Do you want me to keep your bow safe for you?” He stared at her for a moment until he remembered the prissy bow on his head.
“Yeah.” He muttered through gritted teeth. She smirked and helped him get it out of his hair. He knew that it would return to its place far too soon for his liking.
Returning to focusing himself, he broke into a run, pounding down the dock, tutu bouncing with every step. Refusing to allow that to bother him, he launched himself off of the end of the dock. He plunged into the lake before bursting back up with a grin. He knew without a doubt that he had won, even before Jessie took her turn. She charged down the dock and he held his breath without even realizing it as she took flight.
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HAhha I really loved the way you make jack be turned in little Jackie hehe I think deep down he really likes ! And maybe you could use my suggestion that make jack use pampers hehe maybe a pampers model kkk it would be hilarious
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Thanks for this latest chapter. The little girl's swimsuit was unbelievably hot for me. Especially his mom marching him back outside in it. I really hope "Jackie" and she/her pronouns come back into play soon. Ditto with Jackie's pacifier.
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Pierrylouys - Maybe we should let Jack read your suggestion. Then he'll know he's getting off easy with his mom in control!
Pervscenes11 - As Jack begins his descent once again, who can say what the future holds in store for him? At least the summer can't last forever!
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I love this story. It shows a lot of imagination and it is fresh. Having a single dad next door with two kids was unexpected.
How tall is Jack? If he is a bit shorter than his sister then he could be as much as three inches shorter. If his sister is average then Jack would be at the lower end of the height scale for a boy his age
I believe Michal believes that Jack has a pants wetting problem and is going out of his was way helping Jack with his problem. This is to impress Diane which is his love interest. Diane may have mentioned Jack’s wetting problems when they met the day before. So I would expect Jack will be having more accidents.
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Bobbie99 - Thanks for commenting! I get the feeling you just "binged" it all at once, so welcome, even if that's not the case! I've gotten a few questions already about the heights because I don't really have an editor reading this for me, I've had my share of continuity problems. Suffice to say, Jack's a little under average for a boy his age, Jessie's an inch taller than him and Kyle is "at least" three inches taller than Jack. I'm a big proponent of readers' images of characters, so if you imagine them differently, all the better. I have a set image of them all in my head, but I sometimes have trouble translating mental images into words. I'm certainly still learning as a writer.
I enjoy hearing readers' theories about the motivations of the various people in the story. I try to sprinkle foreshadowing throughout the story, so when theories line up with what will be revealed in the future, it makes me smile. It also makes me smile when the theories aren't what I have planned because it means readers are engaging with the story, so keep them coming! Tell me about how Denise is actually an alien who's using mind control to manipulate the whole summer. Go crazy! :)
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now maybe after swimming back into diaper and onesie
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Andlat, another excellent segment and further glimpses into the characters. I have decided to do some speculating and character interpretation based on the encouragement you gave Bobbie99
Diane, in my opinion, is starting to show her true colors as a cold harted b....h. First she allows the neighbors to believe Jack is younger than his age and encourages his feminization through play with the much younger Caitlyn. Then, when Jack rightly objects to wearing the water wings since he is fully capable of swimming as evidenced by his prior day swim with Jessie, she spanks him and dresses him in an exaggerated girl's suit with tutu and bow in his hair. I don't trust Diane at all at this point and neither should Jack. He should just walk away at the earliest opportunity. I expect her character to get nastier as the story unfolds. Perhaps she's taking out her anger at her former husband for leaving her (don't know whether they divorced or he died).
Jack, for all his apparent whiny compliance with everyone else's wishes has finally shown some gumption with his response to Jessie's challenge to jump farthest into the water. I pray that this character continues to demonstrate, even if passively, that no one is going to beat him, even mommy dearest. I also wish he had told Jessie to leave the bow in but stripped off the tutu to improve his jump.
Jessie seems to be a prototypical sibling with a bit of a mean edge of passive-aggressiveness as demonstrated by her jumping challenge to Jack so she could see what he was wearing and enjoy his embarrassment. Classic that Diane virtually never corrects or punishes Jessie.
Michael is actually starting to become very interesting. He never seems to defend Jack against Diane. Not that he should generally interfere with a parent's interrogative but Michael seems to reinforce Diane's regression and feminization of Jack with the little boy swim trunks, the nap, the cut up PBJ sandwich consistent with Caitlyn, and his lack of response when Jack objects to the water wings, to name a few. With not a lot to go on but an overall picture of this character I will hazard a guess that Michael is Denise's "daughter" who was regressed and sissified at the cabin where Jack and family are staying. His apparent subservience to Diane seems to support this hypothesis. The fact that the cabin is "secluded" but has a neighbor within walking distance might mean Denise owns both properties and she has and continues to use them to sissify boys and men. Michael may be afraid that Diane will regress and feminize him if he doesn't support her and Denise can always visit to assist Diane.
Kyle has been described as aloof but I think it is fear that has him staying distant from Jack. I believe he has been subjected to the same treatment as Jack and is afraid of it being imposed again. If I am correct about Denise being Michael's mother or at least a relative, it's highly likely that Kyle has been regressed and feminized. Caitlyn's comfort with Jack as a baby girl also supports this position.
Caitly seems more of a catalyst in Jack's feminization and regression. At her age I can't see anything deeper in this character.
I realize that my comments may be longer than parts of your story and so I apologize if you find them offensive; however, you did seem to encourage such discourse in your prior comments. Thanks for your excellent work.
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Jessie splashed into the water not far from Jack, but he knew that he had won. He grinned and started swimming back toward the shore to celebrate his victory. Caitlyn was jumping up and down excitedly and even his mom and Michael looked impressed. Jack could not even say how much his success had meant to him. Even stepping out of the lake in his sissy swimsuit could not dampen his spirits.
“Must be late for ballet class.” Jessie called after him as he emerged from the lake. He grabbed his towel, ignoring her and wrapping it around his waist. Jessie shrugged and called for Kyle to join her in the lake. He complied as Caitlyn came over to Jack.
“You jumped so far!” She said, eyes wide and shining with admiration. “Oh, Jessie gave me your bow to hold on to. Let’s go ask your mommy to put it back in your hair.” She grabbed Jack’s hand and tugged. He sighed, knowing that his mom would expect it of him. “I’m glad you’re dressed like a girl again.” She said as they walked over to Diane, who Jack knew could hear Caitlyn’s continuous monologue. “Boy clothes looked weird on you.” She smiled up at Diane. “Here’s Jack’s bow, Miss Diane!”
“Thank you very much, Caitlyn.” Diane said, taking it from her and quickly reattaching it to Jack’s short hair. He was not even sure how she did it.
“Is Jack going to wear diapers again?”
“Not yet. He’ll be staying in his swimsuit for a while. I didn’t bring a change of clothes for him.” Jack looked at his mom inquisitively, but remained silent. “Do you like his swimsuit?”
“It’s okay. I think Jack likes pink more than I do though.”
“Huh?” Jack looked down at her in confusion.
“I heard you tell Jessie that pink’s your color.”
“You did say that, Jack.” Diane said with a laugh. Michael came over.
“Grill’s lit for our early dinner.” He said. “Caitlyn, if you’re done swimming, why don’t you run inside and get changed?”
“Can Jack come with?”
“He’s still wet, sweetie. You go get changed and then you and Jack can play again while you wait for dinner, okay?” Caitlyn nodded and hurried inside, waving back at Jack. “She’s an energetic one.” Michael said with a chuckle. “And she certainly seems to like you, Jack.”
“Yeah.” Jack said. “It’s tough keeping up with her sometimes.”
“That it is.” Michael grinned. “That it is. Every year, we hope one of the neighboring cabins will have a girl around her age to keep her occupied. Kyle tries to play with her, but he’s not always the most willing.” He looked out at the lake where Kyle and Jessie were playing an informal game of Marco Polo. “I’m sure this’ll embarrass you, Jack, but you’re honestly the closest thing to a girl her own age we’ve ever had at the cabins. You must have played a lot of girl games growing up with Jessie?”
“Definitely.” Diane interjected with a fond smile. “I eventually had to sign Jack up for Little League just to get him some time with other boys.” Jack looked at her. Standing there in a pink swimsuit that his mom had put him in to make him be a good little ‘girl’, he wondered why she was talking like this.
“Kyle and Caitlyn are far apart enough in age that they just kind of stay in their own spheres. Kyle tends to disappear whenever Caitlyn has friends over, but Caitlyn always wants to play with his friends. That’s why she’s so excited about you, Jack. You’re an older boy who plays her games.” Jack nodded, pulling the towel tighter around him. He felt almost like a grown-up in this conversation and he did not want his swimsuit to remind his mom and MIchael that he was steadily becoming more and more of a little girl in their eyes. “Anyway, I better get the meat from inside.
Jack sat on the nearby bench, holding the faded Spider-man towel around himself, trying to cover up his swimsuit as much as possible. Diane sat down next to him, slightly adjusting the bow that he had forgotten was still atop his head.
“It’s a shame your hair isn’t longer. You’d look so cute in pigtails or braids like Caitlyn’s.”
“Mom!” She gave him a look. “I mean, mommy!”
“Well, you’re being a little girl right now, remember?” She gave him a hug. “You look so much like Jessie that it’s not hard to imagine you with longer hair. But, it would take a while to grow it out.” He could not even say how grateful he was that that was the case.
“Can I go back to my clothes when we get back to the cabin?” He asked, knowing that there was little chance it would happen any sooner.
“I’m not sure, Jack.” His mom replied. “You’re a lot better behaved as a girl than as a boy.” She smiled at his face. “But, but.” She added to mollify him. “I’m not too keen on changing your diapers this whole vacation.”
“That’s a relief.” He muttered.
“You should be glad I don’t put it up for a vote. Jessie and Caitlyn would team up and probably get rid of all your boy clothes before you even knew what happened!” She chuckled at the thought.
“I still think it’s weird that you’re making me do this.”
“I know, Jack, I know.” She said gently. He sighed.
“Can I go change?”
“Into what?” She asked. “I’ve packed up your clothes. You won’t be wearing them again for a while.”
“But” Jack could feel tears welling up in his eyes. “I’m trying really hard to behave, mom, but it’s just so embarrassing being treated the same as Caitlyn!”
“I know, Jack, I know. I can’t say why, but you really do behave better dressed like this than you did in your regular clothes.”
“So, I’m stuck like this?”
“For now. Like I said earlier, we won’t do diapers, at least during the day.” She hugged him. “You’ll wear the dresses in the nursery again, but what we’ll do for underwear, I’m not sure. Probably just let you wear your regular undies under them.” She smiled. “It’ll be strange, but I think that’ll just have to work.”
“I promise I’ll behave.”
“I know, but you seem to forget your promises pretty quickly, don’t you?” A few tears of frustration slid down Jack’s cheek. She hugged him again.
“You're really going to keep me in dresses?” Jack asked.
“Yes, but you’ll get to pick them yourself. I know you can’t imagine yourself picking out a dress, but it’s what’ll happen.” She replied. “But remember, you’ll wear your own underwear under them, so it’s not all bad.”
“Not at night.” Jack muttered.
“Right. You’re still going to wear diapers at night. Your little dash to the bathroom this morning made me and Jessie nervous.”
“What about swimming?”
“Well, I suspect Jessie will have you go swimming everyday once she realizes you’ll be wearing your new pink swimsuit.” She smiled, moving his towel slightly out of the way as if he did not remember that he had it on. “But, if you cooperate with this, you might just find yourself earning your boy clothes back. If you don’t cooperate though, I won’t hesitate to take you into town to buy some panties. Maybe even get your ears pierced and your nails done.” The look of horror on his face almost made Diane regret mentioning it. “That’s just if the dresses don’t seem to be working.”
“There must be some way to keep Jessie from teasing me constantly.”
“You know your sister, Jack. She’ll tease you until you stop letting it bother you. You’re obviously getting to that point, so just keep it up.” Jack nodded, but he wished his mom would intervene more. “Oh, remind me to take a photo of you and Jessie in your swimsuits.”
“Mom!”
“Oh, come on! I didn’t take any pictures of baby Jackie, let me at least get a couple of you in your pretty pink swimsuit.” She hugged him again, but he did not know if she was joking or not.
Caitlyn emerged from the cabin in a denim skirt and a yellow t-shirt, carrying both Petite Belle and Sterling Sparkles in her arms. She skipped over to Jack.
“Here’s your pony, Jack. Let’s pretend they’re flying again.”
“What’s your pony’s name, Jack?” Diane asked.
“Sterling Sparkles.” Jack replied softly. She smiled and eased the towel off of his shoulders.
“Go play with Caitlyn, Jack.”
“Can’t I wear the towel?” He asked.
“I think it would be tough to run around if you’re worried about the towel, but if you want to try, you can.” He knew that she was right, but he was too stubborn to admit it. Draping it over his shoulders like a cape, he tried to tie it around his neck, with little success. Diane watched, patiently smiling.
“C’mon, Jack!” Caitlyn whined. “Petite Belle and Sterling Sparkles need to get to the Frost Queen’s castle before it’s too late!” Jack sighed and tossed the towel on the picnic table.
Encouraged by the presence of an audience, Caitlyn insisted they do more than simply run around. Jack followed her as they skipped, pranced, and did a variety of other activities always in the sight of either his mom or Caitlyn’s dad. Throughout it all, Jack felt terribly exposed, dressed as he was in nothing but the pink swimsuit. He could hear the snickers once Jessie emerged from the lake to see him playing with Caitlyn, but there was nothing he could do with his towel over by his mom.
“Girls! Dinnertime!” Michael called. Jack could not be sure that he had actually said ‘girls’, but that was what it had sounded like. He hurried over to the picnic table with Caitlyn, glad that it appeared as though everyone would be eating this meal together. “Who wants a burger and who wants a hot dog?” Michael asked. “Got plenty of both!”
* * *
Once dinner was done, Michael wiped Caitlyn’s face and Jack had his wiped by his mom before he could even protest. Kyle sagely scrubbed his own to make sure he did not get the same treatment.
“I suppose we’d better get back to our cabin.” Diane said.
“Yeah, it’ll be bedtime for a certain little girl soon.” Michael patted Caitlyn’s shoulder.
“Yeah, Jack.” Jessie whispered to him. Jack tried to kick her under the table, but missed.
“Say your goodbyes, kids.” Michael said.
“Can’t Jack spend the night?”
“Not tonight.” Michael said. “But maybe we can play a sleepover sometime soon?” Jack looked less than enthused.
“Ok. Bye, Jack! I hope I get to see you again tomorrow.” She hugged him and Jack shyly returned the hug. Kyle quietly said good-bye to Jessie and disappeared inside before Jack could even blink, it seemed.
“Let’s go, kids.” Diane said, standing up. “Thank you very much for a lovely day, Michael. We’ll have to get the families together again soon.” Michael smiled and nodded.
“I think they’ll all like that.”
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Hi Andlat, thanks for the new chapter. Poor Jack is right back to where he was no matter how much he tries to satisfy the monster that is his mother. Will he ever ask her why she hates him so much? I imagine the pics she is taking will be used at home to force him to do exactly what Diane and Jessie both make him do.
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This is a great story presented in a way that the reader feels and identifies with the humiliation James is experiencing. Very good writing. Use of the sibling rivalry and a mom that can see no wrong in her daughter is classic.
James should only realize how lucky he is. I sure hope that this is at least a two-week vacation. Please keep this story going in the current direction. We readers are loving it.
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Please more it great story
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I have to say you are keeping me on the edge of my seat wondering what picayune thing Jack does or says will cause Diane to inflict more sissy punishment and the severity of that punishment. Especially like the carrot and stick approach of Jack being required to be a little girl in a dress but allowed to keep his boxers. Then the stick again of Jack needing to wear diapers at night and Jessie as a partner with Mom in making that decision. Love the more mature and superior role Jessie is growing into and Diane's encouragement of Jessie's position as the "older" sister. Very realistic given sibling rivalry with Jessie not being too involved at this point and very well written.
Still trying to figure out Michael's role in Jack's sissification and regression and his motivations. Finally, I can understand Kyle's standoffish attitude to Jack not wanting to be associated with a sissy but I don't see him as just the alternative real boy to Jack's sissy. I still think there is something in store for Kyle but even if not he's a great character to highlight Jack's descent into little girl status.
Thanks for writing and keep up the great work. You may have noticed that with 17+K views you have a lot of people's attention.
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Will please post more
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Wanted to add to the chorus of voices begging for more of this great story. I, for one anyways, have really enjoyed the slow pace of Jack's social demotion into little girl-dom. Would kill to see more of it!
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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.
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Thank you for this awesome new installment. One thing I've loved about this story is how everyone in the story except for Jack (his Mom, his sister, the neighbors at the next cabin) have just rolled right over him and made it clear that they see him as a little girl. It was interesting to see that that steamrolling is starting to affect Jack's outlook in certain ways. I can't wait until everyone starts using female pronouns for Jack regularly.
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Thank you for another well written sweet chapter.
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This last segment was very good. It gives us readers a lot to think about. Personally, I would have found this segment hard to write.
Jessie and Diane are once again their selves. Diane being manipulative and allowing Jessie to taunt poor Jack. Jack maybe has had enough of Jessie in that he choses to sleep in a crib rather than sleep in the same room with her. Then again will to sleep in the crib removes a possible punishment Diane can use against him.
Readers please show your support for this story by sharing your appreciation with the author.
Please keep the story going.
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You're definitely taking us on a roller coaster ride with Diane's mercurial nature. One of my favorite aspects of the story is the carrot and stick approach used by Diane, from the extreme of making Jack a baby girl in a playpen when the family first met the neighbors to granting him full boy clothes for a day or so. I especially like the fact that Jack has to wear a dress for the rest of the vacation but if he's good he can wear his own underwear. Talk about conflicted!!!! My guess is that he will be in full feminine finery again soon. And, of course, it's diapers and baby panties at night.
I'm also still waiting for a greater impact from the neighbors. Seems Michael's primary interest in encouraging Jack's sissyhood is that he makes a perfect companion for Caitlyn but wonder if there is a deeper reason. Also, Kyle's rejection of Jack seems instinctual (he doesn't want to associate with a sissy) but I wonder if his standoffishness (is that a word? ;D) runs deeper than that (e.g., is Kyle a bedwetter or has he ever been disciplined like Jack). Finally, I'm hoping Jessie will emerge as a more central character. So far her major impact has been teasing Jack and he is beginning to slough that off. It would be interesting if Jessie emerges in a superior role as, perhaps, a babysitter for the inevitable sleepover. Kyle could join and be advised that Jessie's in charge after he arrives for the event. If Kyle is a bedwetter, then what role does Jessie take???????
Thanks for all your effort and the great writing you provide. Looking forward to the next chapter. In closing, don't mean to pry but hope that chapters coming further apart doesn't mean you are having any personal difficulties. If so, hope any issues are soon resolved and all is well for you.
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My apologies, all, for the period of silence on my part. I have resumed work on Jack's summer adventures and I hope to have more for my wonderful readers soon. We're about to enter a whole new phase of the story that I'm very excited to share with everyone. Questions will be answered, I assure you!
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Better not be April Fools, Andlat. :P
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I take you at your word even if it is April 1. 8) I have to admit, the long period of silence had me worried about your circ-umstances/health. Glad to hear from you.
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Ha ha! While you both weren't looking, I pinned paper fish to your clothes! Poisson d'Avril!
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Hoping against hope that this word of new material is NOT an April Fool's joke. This story is SO amazing. I've been checking every day hoping for a new installment. The more I re-read, the more I am fascinated by Caitlyn's dad. I love that he seems willing to feminize Jack in order to get his daughter a playmate. Cannot wait for the promised sleepover. I think I'm going to lose my mind when Caitlyn's dad starts using female pronouns for Jack and calling him a princess/girl.
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Just to be unequivocally clear, this is not an April Fool's joke. I am genuinely working on the next part. Watch this space for more news as it develops.
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Thank you! So exciting! Really hope we get to see Jack spending the night with Caitlyn and being fully seen/treated like a little girl by her Dad.
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Diane chose not to mention to Jack that she saw him admiring his dress, knocking on the door to warn him. She smiled as he spun around, a guilty look on his face. She knew he knew that she saw him and that was all that mattered.
“All set?” She asked, walking over to him and gently adjusting his dress’s skirt.
“Yes, mommy.” He mumbled. She smiled and could not resist gently stroking his hair before kissing his forehead.
“I hope you don’t mind me saying you look pretty.”
“Can I be handsome instead?” Diane smiled and fussed with his hair.
“Let’s get some breakfast.”
When Jessie saw Jack’s dress, she smiled, but her mom’s look silenced her before she even began. She sat down across from him and ate her breakfast without a word.
“What shall we do today?” Diane asked merrily.
“I’d like to go swimming again.” Jessie said.
“Will we be seeing Kyle and Caitlyn again?” Jack asked with a touch of anxiety sneaking into his voice.
“I don’t think so, at least not today.” Diane replied.
“I think Kyle said his grandma’s visiting today.” Jessie added. Diane nodded.
“Looks like you’re stuck just playing with your sister.” She smiled impishly. “I don’t think she’ll play the same games you played with Caitlyn.”
“Well, we’ll go swimming.” Jack mumbled. “As long as I don’t have to wear water wings again.” His face fell as both Diane and Jessie giggled.
“Oh, calm down, Jack. The water wings you wore were left at the other cabin. I know you can swim. You and Jessie took swimming lessons together.”
“Do you want to swim now?” Jessie asked as they cleared the table following breakfast.
“Not yet.” Jack replied.
“Well, what do you want to do?”
“Dunno.”
“I’m leaving it up to you, Jack, since you stand the biggest risk of being embarrassed, dressed like, like that.” She gestured to his dress. Diane watched her daughter closely, but it seemed as though Jessie was behaving, for now. Jack did not answer, feeling Jessie’s eyes on him. Would she figure out the secret he held deep inside? No, there was little risk of that. Even his mom did not know.
“Do you want to play inside or outside?” Diane asked, trying to nudge Jack toward a decision. He shrugged again. “I don’t want to hear you two saying you’re bored, so” she paused and thought for a moment. “Jack, go pick out a doll. You two are going to play the game that Caitlyn taught you yesterday.”
“We played checkers.” Jack said, but he knew that that was not what his mom was alluding to. Diane’s smile faded slightly for the briefest second, but quickly returned.
“I think we can assemble a whole tea set for you two to have a nice tea party. With dollies.” Jack and Jessie exchanged a look, bonding in their lack of enthusiasm for that idea. “My mind’s made up, kids. Jessie, clear the table. Jack, go pick your doll.”
Not ten minutes later, they sat across from each other on the living room floor, an ottoman serving as a makeshift tea table as Diane looked on approvingly from the other room. At first, they kept up appearances and played with the dolls as earnestly as they could, but they soon discovered that, as long as they held the dolls, their mom did not seem to care what they did.
“I’m really glad mom didn’t insist on me wearing one of those dresses.” Jessie said softly.
“You should.”
“Don’t you dare tell her!” Jessie hissed. “I’ve got an awful lot of blackmail on you, you know.” For once, Jack almost felt relieved their mom had insisted they did not need cell phones on the trip, going so far as to search their bags to make sure they did not try to smuggle them.
“Like what?”
“The way your face turns red should be more than enough proof for my friends.” She said confidently. “Or your friends.” She added. Jack did his best to project indifference, but he knew that his twin sister could see right through him.
“Shuddup or I’ll tell mom you want to wear dresses like” he paused, trying to think of a way to word it without it sounding like he was claiming ownership of the dresses. “Like the ones she’s made me wear.” He smirked. “Wouldn’t you just love spending an afternoon as a baby girl?”
“Kids.” Diane called from the other room, not even looking up from her book. “If either of you intentionally gets the other one in trouble, you’re going to start sharing punishments again.” As kids, if one of them got a timeout, the other did too. That was back in what Diane had dubbed the ‘double trouble days’.
“Mom, can we go swimming?” Jessie called, eager to get out from under their mom’s watchful gaze.
“I suppose so. Jack, your swimsuit should be in your room still, right?”
“I think so.” Jack said. He tried to stand up gracefully, but the frothy petticoats of the dress had other ideas. Jessie giggled at her glimpse of his boxer briefs.
“I see your panties.” She whispered. Jack glared at her, but he would wait to get his revenge until their mom was not right there.
* * *
Jack set his underwear aside and stood there naked for a moment, sighing softly as his gaze fell on the pink swimsuit. His trunks had to still be upstairs in the suitcase, but how would he get to them? He weighed his options for a moment before inspiration struck him out of the blue. He would sleep upstairs tonight and, once Jessie fell asleep, he would hide his suitcase somewhere where only he could find it. He would take back his regular clothes and then no one would be able to stop him from dressing like himself again. It was foolproof, wasn’t it? He looked at his reflection for a moment, hoping that it would reassure him, but he still doubted his plan. How would mom react if he tried it? He shuddered as he imagined being sent to school again in September still in dresses. His mom would never do that, would she? It was one thing to make him dress like a girl in front of strangers, but in front of his friends? That was too far, right? She could, he supposed, let him dress like a boy at school and make him dress like a girl at home. He shuddered. That almost seemed like a possibility.
As he stepped into the swimsuit, he faced the facts. He would have to continue wearing dresses. It really was not all that bad. Sure, if he was not careful, he flashed people, but it was not like his mom or Jessie had not seen his underwear before! He glanced at himself in the mirror, a bit shocked that he had just admitted, even to himself, that wearing dresses was not that bad!
“It’s not like I like wearing them.” He reassured himself. You just don’t mind, a nagging voice in the back of his head accused. He chastised it, reminding the nagging voice that wearing a dress over his regular underwear was a lot better than the brief period he had spent as a baby girl.
As he looked around the nursery, however, he realized that he probably would have to wear a diaper for the drive back home, but maybe he could earn a thinner diaper with good behavior. He marveled once again at just how much he had gotten used to in the last few days. What had happened to the tough boy he had been?
“I’m still the same.” He said without much conviction. After all, the dresses had started to grow on him, much as he hated to admit it. A soft knock at the door pulled him from his thoughts. “Don't come in! I'm naked!” Jack called, hoping that that would stop whoever it was from barging in. He had to relish every second of privacy he got.
“You ready now?” Jessie called through the door. Jack took one last look at his reflection and sighed. He stepped out of the room and they headed to the lakeshore, blissfully unaware of how things would change completely once their swim was over.
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Andlat, thanks so much for this latest installment. I find the idea of a boy forced to wear a little girl's one piece bathing suit super hot, and so I was glad to see Jack back in that. Seems like his feelings about the whole situation are changing rapidly, and now we have signs that he's keeping a deep secret. Is it just that he wants to be a girl? Intrigued to learn more, and to see what this big change that's been alluded to is.
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Andlat please more to this story
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Please continue this story. Maybe an accidental pants wetting or a wet bed during nap time will put Jack back in diapers and baby girl dresses? Maybe both? This is my favorite story.
Andlat. I also like the suggested idea of Jack spending the night with Caitlyn and the being fully treated as a little girl by Caitlyn's dad and grandma. Night time diapers with ruffled panties at bed time. Wet diapers in the morning. Even Caitlyn beginning to treat Jack like a baby.
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I second bobbie's comment x1,000,000! I so hope this story continues and that we get to see Jack and Caitlyn's sleepover (with Caitlyn emerging as the older, more mature of the two girls, and with Caitlyn's dad fully accepting/embracing Jack as a girl).
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Thank you all for your kind words and for indulging me as I took a bit of a break from this story. I enjoy reading your comments and it makes me so happy to see that you all are still thinking about my story. Below is the next chapter in the story!
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Despite wearing the girly pink swimsuit, as they walked back up to the cabin, Jack almost felt like things were normal. Even the fact that he would have to put a dress on again did not really faze him. Seeing Michael’s car parked in front of the cabin caused him to stop though.
“Looks like your best friend Caitlyn’s here, Jack!” Jessie teased. “Maybe it’s time for your sleepover?”
“I hope that doesn’t actually happen.” Jack muttered. Jessie giggled.
“I promise, little bro. I’ll make it happen.” Jack tried to punch her in the arm, but missed and stumbled, much to her delight.
When they stepped inside, however, they were surprised to see that it was only Kyle there, along with an older woman who had a glass of lemonade in front of her. She smiled as she saw Jack, but did not say anything. Kyle seemed perfectly content to study his hands, but he seemed nervous about something.
“Go get changed, you two.” Diane said. “This is Kyle's grandmother, Denise.”
“Nice to meet you.” They mumbled in near unison before going off to change.
“Hurry back. She wants to talk to you, Jack.” Diane called as Jack disappeared into the nursery. She wanted to talk to him? What did that mean? What about?
In his anxiety, Jack hardly even blinked as he pulled the dress over his head, but as it settled, he considered how nonchalantly he had put it on. What had happened to him? Not even a month ago, he had turned his nose up at certain shows for being too girly and now, now he willingly put a dress on after taking off a girl’s swimsuit. He need to stand his ground. Enough was enough!
“Almost ready?” His mom called from the kitchen.
“Yes.” He called back, feeling a bit rebellious for not saying ‘mommy’. No, his days of saying ‘mommy’ were over again. That much was for sure. It was only as he pictured marching out there to give his mom a piece of his mind that he remembered the presence of Kyle's grandmother. What was she doing here? Why did she look so happy to see him in that swimsuit? “Guess there's only one way to find out.” He muttered, looking at his reflection. He knew that the yellow sundress was about the plainest dress that there was in the room, but he still missed his old clothes. He liked dark colors, but there were no dark colors in the room, except for the boxer briefs he wore under the dress. He took a deep breath and marched back toward the dining room, determined to still remain firm, no matter what Denise threw at him.
“Let me took a look at you, princess.” Denise said as Jack walked back into the dining room. It took him a moment to realize she was talking to him, and it was only when he noticed his sister giggling at him. He dutifully walked over and stood by her chair. “Give us a spin.” Jack did so and her sharp eyes caught a glimpse of what he wore underneath.
“What's this?” She asked, lifting his skirt and looking at his underwear with evident distaste. “Why is he wearing those?”
“It's made him a lot more cooperative.”
“There are other ways to make a boy cooperative. Just look at what Michael and I did with Kyle.” Kyle's eyes widened and his face reddened. Denise looked around the room at the surprised faces. “You mean Michael didn't tell any of you?” Denise said. She clicked her tongue in annoyance. “Kyle, dear, show the nice people your secret.” Used to his grandmother's domineering ways, Kyle unbuttoned his shorts with a minimum of fuss, revealing a pair of pink rhumba panties, a more mature version of the panties Jack had worn over his diapers, albeit only slightly more mature. He could not be sure, but Jack suspected that Caitlyn would dismiss them as too little girlish for her, yet here they were being worn by a guy that Jack had thought was cool! Kyle's face was red, but he knew he could not pull up his shorts without Denise's approval.
“I spent all of last summer in the same position as you, Jack.” He explained softly. “Dresses, diapers, the whole nine yards.”
“But I was here to make sure he learned his lesson.”
“At the end of the summer, my dad and grandma thought that my behavior had improved to the point that”
“We decided” Denise interrupted. “That he would remain in panties. And look, your grades were much better.”
“You wear panties like that all the time?” Jessie asked, wide-eyed. Jack knew his sister and could tell that she was shocked, but he could see the slightest glimmer of delight in the back of her mind.
“My dad relented and lets me wear boy undies for Phy Ed days.” Kyle said.
“Yes,” Denise said, her disapproval written all over her face. “But nothing like the underpants Jack is wearing under his dress. What was it you called them when you first saw them, Kyle?”
“Uh, tighty whities.” Kyle replied a bit bashfully.
“But you prefer your panties, right?”
“Yes, grandma.” Kyle mumbled.
“See? Now, Diane, there's a boutique in town that sells just the sort of panties Kyle wears. What do you say we go get Jack some more appropriate underpants?”
“Mommy, no!” Jack exclaimed. Jessie, however, looked like Christmas had come early.
“Can we, Mom?” She asked eagerly. Denise smiled.
“At least one of you is enthusiastic.”
“Denise, can I talk to you in the other room?” Diane said. “I’ve been taking things slowly and I’m not sure if this is quite the right move.” The two women disappeared into Jack’s bedroom, closing the door behind them. With a sigh of relief, Kyle zipped his shorts back up.
“So, now you know my secret.” He said, looking from Jack to Jessie as if he could not decide who he did not want to know his secret more.
“You really wear those all the time?” Jessie asked.
“Um, yeah.” Kyle replied.
“How do you keep them secret?” Jack asked, thinking of all the times his pants had sagged just enough to show his waistband.
“I'm really careful." Kyle said. “I've been wearing them for a year, so I've had a lot of practice.” He glanced toward the closed door. “Maybe I can teach you a few tips and tricks, but it sounds like you'll be in dresses for the rest of the summer, so it'll be hard to practice.” He looked at Jack sympathetically. “I never really got used to dresses.”
“I won't be in them for the rest of the summer.” Jack said firmly, but he knew that no one, including himself, really bought his conviction.
“My grandma tends to get what she wants.” Kyle said. “And she seems pretty committed to you going through the same thing I did.”
“Why?” Jack asked. Kyle could only shrug.
“My dad says that once she gets an idea in her head, nothing will convince her otherwise. She's dedicated and stubborn.”
“Mom will fight for you, Jack.” Jessie said, sounding oddly supportive. Jack could not help but smile at her appreciatively.
“Thought you loved this happening to me.”
"Well, just as a punishment.” Jessie replied, a bit sheepishly. “I don’t want you permanently in panties and stuff. Sorry, Kyle.” Kyle shrugged.
“Honestly, I’m used to it. You guys had no idea I wore them until grandma made me show you.” He glanced away for a moment. “And honestly, I usually forget that I’m not supposed to wear them.” Jack could not imagine ever feeling like that, but he kept his mouth shut. It seemed like Kyle would be more of an ally than he had expected.
It seemed to Jack that it was hours before his mom and Denise emerged from the bedroom, both women looking quite satisfied.
“We’ve come to an agreement, Jack.” His mom said as the older woman nodded approvingly. “You’ve got a choice.”
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Whaaaaaattt a cliffhanger!! Please I want to knowww
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Me to me to I want to know please.
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Wow, what a chapter! A great twist and a cliffhanger. I'm more excited for this story to continue than ever. :)
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SO GREAT to see this story continued. Thank you, Andlat. Curious now about Kyle/Caitlyn's Dad and his role in all this. I so hope Jack's status as a young girl is permanent, so I'm sorry to see that it was (at least for now) temporary for Jack. Not sure why, but I really long to see Robert accept/treat Jack fully as a girl, use female pronouns for him, etc. Anyways, thanks for continuing this!
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Thank you for coming back to this story so pleased, I love it x
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Well crafted. You nicely present the deep pleasure and confused submission to being infantalized and feminized. Please continue.
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As noted in other responses I can't wait for you to publish the next chapter(s) in this saga. Of course, neither "option" will be reasonable alternative for Jack. Not surprised that Kyle is a petticoatee but I am surprised he is so relaxed about it. I'm having trouble understanding Jack's 'crimes" that are pushing his mother to subject him to petticoating and Denise's Svengali-like influence over Diane.
I think Michael is the original occupant of the nursery where Jack now finds himself and this would also explain why he is so agreeable to Kyle's and Jack's petticoating. Wonder if Michael is still petticoated and also was he ever married and, if so, what became of his spouse. Are Caitlyn and Kyle his natural children or are they adopted?
I do like that Jessie doesn't want Jack petticoated either for the whole summer or permanently. Her position enhances the reality of the situation. While I read these petticoating stories for the same reasons as everyone else, I also like to consider what I would do in these situations and how I would avoid entrapment. Hence, I loved when Jack jumped out of the crib even if his attempt was quickly thwarted. Hopefully, Jack puts up a little more resistance to Denise's twisted plans.
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Andlat, PLEASE continue this amazing story. I am surely not the only one dying for a new installment!
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Andlet please continue this story. We know that life sometimes gets in the way but your readers are out here waiting.
From a previous episode of mom putting Jack and his sister to bed we see that Jack is appearing to his mom as being regressing toward being a baby. Willing to wear diapers and nighty and volunteering to sleep in the crib. While his sister appears very mature for her age.
In the last chapter Kyle is exposed to all as wearing very frilly panties all the time to help make him cooperative. Jack’s boy underwear does not sit well with Kyle’s grandmother Denise. Where the story left off Denise and Diane were going into the nursery to discuss Jack’s underwear situation. As we know Denise seems to always get her way.
My best guess is that Jack will be given a choice in underware. So Jack has to choose between very bad alternatives. Either will tear down his masculinity even further.
Any guess what the choices will be?
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nice story...
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great story yes please more
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Andilat, I do hope that you finish this story. It would be nice to know how this story ends. :D :D
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Is this going to be continued?
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Is this going to be continued?
It's on a bit of a hiatus at the moment. Sorry.
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I just finished reading your story and I really enjoyed it. I liked the twist and turns that you included on Jack's journey.
Your last post seemed to give us hope that you may continue the story at some point in the future. I certainly hope that you do.
Take care.
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I'll second what Baby Denise says here. "Secluded Cabin Sissy" is a masterpiece, one of the all-time great sissy/age regression stories. It is a MASTERPIECE, and I'd pay cash money to see it continue. Obviously, Andlat owes no one anything, and can do as he pleases, but I soooooooo hope that this story continues one day. Dying to see the sleepover with Caitlyn, with her Dad supervising!