On The Road Again - Chapter 22

“Are you trying to kill me?” Jill asked, only half-joking.

“Nope! If you want to try to hold for two hours, you can have one now and then one in an hour. But if you want to get it over with as soon as possible, then….” Isla replied with a smirk.

“I’m not actually sure what is the better option,” Jill contemplated. “Alright. Fill it up, and I’ll drink two now.”

Isla jumped with devilish glee, and Jill rolled her eyes before looking down at her jeans. Her hands glided over her thighs to feel the denim, and her heart raced at the thought of them getting wet. She imagined the wetness spreading in them; how warm it would feel so tight against her skin. Jill lost herself in her imagination for a moment, and her core started to warm, slightly dampening her panties with a different wetness than she was imagining.

“Here’s the first one!” Isla reappeared and snapped Jill out of her fantasy. Jill tried to keep her annoyed persona, but she eagerly grabbed the bottle and started swinging back the water. Isla watched in anticipation as Jill lifted the bottle to her lips and tipped it back. The cool water filled Jill's mouth, and she began chugging it back the best she could. A chill washed over her as the water spread its cool temperature down her throat.

Jill only took two breaks to breathe but finished the entire water bottle in just over a minute and handed the bottle back to Isla.

“You know, that’s actually enough water, I think…don’t you think?” Isla said as she grabbed back the bottle.

“You trying to go easy on me?” Jill teased.

“No, it’s just as I was filling it I realized just how much water it was and-”

“Go fill it up,” Jill said, cutting off Isla.

“A-are you sure? Because I don’t want…I don’t know….” Isla blushed. Jill moved in close to Isla’s face and kissed her. Then, she grabbed Isla’s empty hand and guided it between her legs.

“You want to feel this get wet, don’t you?” Jill asked. Isla nodded, still blushing.

“It’s just, I know this is going to sound silly, but this is kind of a strange thing that I like, and I don’t want you to feel like I’m forcing you….”

“Hey,” Jill replied definitively. “It’s a strange thing WE like. You aren’t forcing me to do anything I don’t want to do.”

Isla looked into Jill’s eyes and knew she was serious.

“Fill it up,” Jill said again. After a moment, Isla obliged.

Isla returned, ready and excited after getting in her own head for a moment, and handed the freshly filled bottle to Jill. Jill began chugging it back again, and as Isla watched, she continued to reflect on everything that’s happened over the last day. It was hard to believe that she and Jill had only really been having this kind of crazy fun for such a short amount of time. It was even harder to believe that Jill was so into playing along with her games. These sort of scenarios had only been so much as fantasies for Isla before leaving on the trip, and she thought that she might get to live out a part of one when she figured her friends would keep their word and wear diapers on the trip.

When that wasn’t the case, she felt discouraged but also somewhat excited. She had a secret, a naughty secret. When Jill came into it full force though, it intensified. Now they both had secrets: their diapers and their very sexual relationship.

“Finished,” Jill gasped as she reached the bottom of the 2L bottle once again. “Fuck I’m going to need to pee so bad.”

“Well, you have an hour from….” Isla pulled out her phone and set a timer for one hour. “Now.”

“Where are we gonna go?” Jill asked.

“I think there are some clothes stores just down the road. We could walk there, have a look around, maybe find a cafe, then head back once the hour is ending,” Isla explained.

“And what if I….” Jill alluded to her pants.

“Well, I don’t want you to be too embarrassed, so if you start leaking, we’ll rush back, and you can finish the hour in the bathtub.”

“Sounds fair. Shall we?”

“Let’s go!” Isla sprung up, allowed her skirt to lift and Jill to see her diaper for a glimpse. She knew Isla had one on, but something about seeing it teased like that was exciting to her. Jill stood, and as she did, she felt the rush of water weigh her down. Her tummy felt full and bloated, and she could swear that her bladder was already starting to feel full.

“I’m gonna wear this hoodie, so if you have an accident, we can wrap it around your waist!” Isla said as she put on a grey zip-up hoodie. Jill blushed, feeling small.

“Yes Mommy,” Jill joked.

“Oh my god,” Isla said. “I don’t know if I liked that or not. I think you’re Mommy.”

“I’m Mommy?” Jill asked.

“Yeah! I mean, you have on the big girl panties. I have to wear a diaper because I pee and poop my pants,” Isla said, every word growing into a babyish voice. Jill got close to Isla as they stood near the door.

“So, I’m your Mommy, and you’re just the little potty-pants, huh?” Jill teased.

“Mhm! And Mommy’s don’t pee their pants…that would make them little potty-pants girls too!” Isla replied. Jill bit her lips, enjoying the dynamic.

“Alright, little girl, let’s go.”

Jill and Isla opened their door, exited the room and headed straight for the elevator. As they descended, Jill slowly put her hand under Isla’s skirt and patted her diapered butt. Isla blushed and smiled. Jill pulled her hand away just as they reached the bottom floor. The doors opened and they both stepped out, and Jill realized she already needed to pee.

“Fuck,” she whispered.

“What?” Isla asked.

“Nothing!” Jill pretended.

The girls continued to the doors, and just as they opened them to step outside…

“Hey! Where are you two going?”

Jill and Isla went pale and turned around slowly after exchanging worried glances to see Kennedy waving at them. Kennedy lightly jogged over to them.

“What’s up?” Kennedy asked.

“We were just, uh,” Isla started.

“We were just going to look at some stores,” Jill finished, her need to pee building as her anxiety of the situation grew.

“Oh, cool! Can I join? Heather wanted to take a nap. Classic Heather,” Kennedy asked.

Isla and Jill looked at each other, not replying.

“Oh my god. Seriously? This was our trip! We’re supposed to hang out before we like, never see each other. Come on. Let’s go,” Kennedy said, charging past Jill and Isla to lead the way.

Isla turned to Jill and whispered, “Are you going to be okay?”

“I think so,” Jill replied with uncertainty.

Isla and Jill took some worrisome breaths and exited the hotel.