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.
Betty Pearl's Sissy Stories 20.1
Topic: Secluded Cabin Sissy (Read 75220 times)
