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.”
Betty Pearl's Sissy Stories 20.1
Topic: Secluded Cabin Sissy (Read 76958 times)
