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?”
Betty Pearl's Sissy Stories 20.1
Topic: Secluded Cabin Sissy (Read 75249 times)
