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?
Betty Pearl's Sissy Stories 20.1
Topic: Secluded Cabin Sissy (Read 75213 times)
