On The Road Again - Chapter 23

“It’s really nice here, isn’t it? Quaint and quiet. I can’t believe I’ve never been here before!” Kennedy babbled on as she led Jill and Isla from the hotel and into the small town. “I always thought I could live in a small town, you know? Where it’s all quiet, and everyone knows everyone. Simple.”

Kennedy continued talking to the girls, not realizing she was just talking to herself. Isla and Jill exchanged worried and annoyed glances. It didn’t take long for Isla to realize that Jill was already desperate, and most of the water she had drunk hadn’t even processed through her system yet.

Isla pulled out her phone and started texting. Jill’s phone buzzed shortly after.

Isla: If you need to pee, we can find a toilet in town for you to go. We don’t have to go through with it.

Jill read the message, looked over to Isla and then typed back.

Jill: I should be okay. Besides, I’m the big girl, right? I can tell when I need to use the potty.

Isla blushed when she read the text and bit her lower lip.

Isla: Yes, Mommy.

Jill smiled devilishly and looked back at Isla, who was all smirks. However, once she looked away from Isla, her face changed to wear worry. Jill did not feel like wetting herself in front of anyone but Isla, but essentially not in front of Kennedy. Not again.

“Ooo! Let’s stop in here!” Kennedy pointed to a clothing store just ahead. Jill and Isla just followed, neither offered much choice nor in the shopping mindset anymore.

Kennedy sifted through clothes excitedly, picking out a bunch of articles to try. Isla and Jill stayed close, not saying much to each other and casually looking through the racks.

“Jill! Come here!” Kennedy called over to Jill. Jill looked up and casually walked over to Kennedy.

“What?”

“This romper. You HAVE to try it on!” Kennedy demanded.

“Oh no, I’m not really looking to buy anything, I-” Jill said before Kennedy cut her off.

“Don’t worry about the money. Just try it on!” Kennedy insisted. Jill continued to hesitate.

“Can I get a room started for you ladies?” An associate of the store appeared and asked Jill and Kennedy.

“Yes. These are for me, and this is for her.” Kennedy handed the romper and her other selections over to the associate. “Oh! And maybe get one started for her too,” Kennedy asked and pointed at Isla.

“Do you have anything picked out?” the associate asked Isla.

“She’ll try this!” Kennedy answered for Isla before Isla could even open her mouth. Kennedy handed the associate a tight, form-fitting dress for Isla to try. Isla blushed as she noticed just how tight it was and as the associate walked away, she approached Kennedy.

“I can’t wear that!” Isla whispered.

“Why not?” Kennedy replied at full volume.

“It’s…too small!” Isla replied.

“Aren’t you a small?” Kennedy asked.

“...yes, but..”

“Then it should fit fine! Besides, all you’ve worn all trip is baggy clothes. I think it's time to skimp it up a little bit. I saw how that Peter guy was looking at you last night.”

Isla blushed and looked down. Jill watched on and felt a strange sensation in her tummy that was beyond pain from her bladder.

“I don’t think he was into me, to be honest,” Isla replied, then she looked up at Jill.

“Do be serious. He was all over you. I swear he didn’t take his eyes off you for a second. I got his number; I’ll give it to you after you try this on!” Kennedy continued.

“That’s alright. Besides, we’re going away for school anyways. Why would I want a relationship right now?” Isla replied. The words hit Jill’s ears, and she felt her stomach drop.

“Um, sex? It’s called a fling? You fuck each other and go separate ways. Easy,” Kennedy explained.

“Even if that was the case, I doubt we’ll see them again,” Isla continued to deflect.

“Uhh, yeah…about that.”

“What?”

“I kinda…invited them to come to the carnival with us,” Kennedy revealed.

“Kenny!” Isla groaned. Jill rolled her eyes.

“What! Heather said it was a good idea. I think she liked hanging out with them more than she liked hanging out with us.”

“Well, you didn’t ask us first,” Jill said.

“I figured you’d just say no!” Kennedy explained.

“You figured right!” Jill replied.

“Okay, okay, I may have overstepped, but this is for both your own good. We’ll give you both some alone time with one of the guys at the carnival and just see what happens! If you really don’t want to fuck them at the end of the night, you don’t have to.”

“I don’t think I’ll want to,” Isla said.

“Neither,” Jill agreed.

“Okay! Alright! I’m just saying, give it a chance!” Kennedy ended the debate and walked towards the change rooms, giving Isla and Jill a moment alone.

“Are you okay?” Isla asked, making a casual glance at Jill’s crotch.

“Holding on for now, but I don’t think I should try on that romper.”

“I don’t think I can try on that dress. My…diaper…will definitely show!” Isla complained, whispering the word ‘diaper.’

“Then you definitely should try it on,” Jill teased.

“No way!”

“Hey, who’s the mommy here?” Jill replied, putting on a stern tone. Isla blushed and looked down.

“You are…”

“Then be a good girl and go try on the dress. Send a picture to me when you have it on, and come out back in your ordinary clothes and say it didn’t fit. Okay?”

Isla hesitated. “Okay…”

“Okay, who?”

“Okay…mommy,” Isla blushed and looked around to see if anyone had heard. “But what about you? Are you going to try on the romper?”

“No, I don’t think so,” Jill replied.

“Why not?” Isla asked with a smirk.

“Just because…” Jill replied, trying to maintain control of the conversation. “I don’t need to give you a reason for everything!”

“I know why. You’re afraid you’ll go potty in it and have to buy it!” Isla said, now with confidence. Jill shushed Isla and looked around.

“That is not true!”

“Well, try it on then! Since you’re a big mommy with a strong bladder, it shouldn’t be an issue, right?”

Jill’s discomfort grew, and her bladder was already screaming. Her tummy was still bloated with water which put additional pressure on her bladder. It hadn’t even been 20 minutes, and she already was worried about losing control right there.

“How much longer do I have?” Jill asked. Isla pulled out her phone to look at the timer.

“41 minutes. What’s wrong? Can’t you keep your big girl panties dry for 40 little minutes?” Isla continued her counter-tease.

“Fine. I’ll try it on,” Jill replied confidently and walked over to the change room. Just as she was about to open the curtain to enter, she paused. Pain struck her bladder and swelled through her core. Jill buckled over slightly and pushed her hand into her crotch.

“You alright?” Isla whispered to her.

“Just fine!” Jill groaned as she clenched up. When her strength returned, she quickly opened the curtain and stepped inside. A giant mirror reflected her whole body back at her. Slowly, she spread her legs and squatted slightly to see the crotch of her tight jeans.

“Fuck,” Jill whispered as she saw the golf ball-sized wet stain between her legs. She looked at the romper.

“If anything happens, I’m sorry,” she said to the clothing, then started undressing.