"Aw, it's okay! Just relax and pretend you're at a toilet!" Jill told him.
Jack shook his head. "I... I just don't think I can bring myself to use this thing."
"Just imagine a leaky faucet, a shower head..."
"Sh-Shut up...!" Jack stammered, now digging his hands into his crotch.
Jill shrugged and continued. "Just imagine yourself drinking a nice, cold lemonade... sitting by a beautiful fountain..."
"I-I said shut up!" Jack whimpered, now even more desperate.
"Sorry, did I say a fountain? I meant... a pristine waterfall...!"
It was at that moment that Jack lost all control. He sighed as he felt his diaper getting warmer and growing in size.
All the while, Jill was watching with a big, goofy smile on her face. "Oh... my gosh... I'm peeing in a diaper right now... What has become of my life?!"
"You'll get used to it, ya big baby~," Jill teased.
"Don't call me that!" Jack yelled. "You're wearing one, too!"
"Just try and get used to it. Maybe walk around, sit down?"
Jack shook his head and walked around a bit. Because of how thick the padding was around his legs, it ended up more as a waddle if anything. He made a circle around the room before sitting down on the bed, his diaper making a quiet squish as he did so. "...You know what? I... can kinda see the appeal of it... You don't have to stop what you're doing to go..."
"That's the spirit!"
He stood back up and looked down at the big, yellow spot on the front of his diaper. "This actually feels... nice... Yeah, I think I've gotten used to it..."
"Yay! I knew I could get you into it!" Jill cheered.
Jack scoffed and said, "Well, if you like diapers so much, how about you use yours right now, too?"
"I already pee in it almost every night, you can see that anytime," Jill retorted, scoffing back.
"I didn't mean pee..."
Jill blushed when she realized what he was trying to get her to do. "O-Oh... Well, I've never done that... Not sure if I'd want to..."
"But it's what diapers are for," Jack encouraged. "Come on, you got to see me use one, and now it's time for you to repay the favor!"
"O... Okay... If you want..." Jill slowly got into a squatting position. "Here goes nothing..."
She closed her eyes and began to push. She whimpered a bit as the back of her diaper bulged out and turned a shade of brown. Jack just stared in pure awe. He wasn't even disgusted in the slightest. If anything, there was something fascinating about watching his friend doing her business in a diaper in front of him.
"Hah... Okay, I think I'm done now..." Jill muttered, standing back up. She took a few steps towards Jack, but the smelly load in her diaper made it very difficult. She had to go into a deeper and more embarrassing waddle than before!
Jack smiled as he looked behind her and pulled the back of her diaper open to check. Sure enough, a brown mound was nestled in there, and a rancid smell began to seep out. "Yep, this little baby made a big stinky! Ha-ha!"
"S-Stop...!" Jill nervously giggled. "You wanted me to do it!"
"Only because you made me use mine," Jack said as he patted her messy behind.
Jill cringed and covered her bright-red face. "Ewww! Oh my gosh, ew! That feels so nastyyy!" she whined.
"Come on... You'll get used to it, ya big baby~," Jack teased, using her own words against her.
"Okay, fine..." Jill waddled around, feeling her mess squelching around all the while. "Maybe... Maybe we could get used to this whole diaper thing..." she mumbled.
"Maybe..." Jack agreed. "But we should hide the evidence for now. How about... I change you, you change me?"
Jill gasped. "I, uh... If you want, I mean... I guess..." It was clear she wasn't very comfortable with being changed by someone else.
"If you don't like it, we don't have to do it..."
"W-Well... Maybe it could be... interesting for a change?" the girl murmured. "N-No pun intended, of course, eh-heh..."
Jack sensed her unease and volunteered to be the first one on the changing table. He hopped up onto the table and laid down. "Ready when you are..."
"O-Okay..." Jill approached the table and slowly began undoing the tapes on Jack's diaper.
"It's only wet, no need to fear it," Jack told her. "I'm gonna have a lot of trouble with your rancid booty, though."
Jill chuckled anxiously before continuing. She tried to imagine it was someone else and not her boyfriend lying there as she took the diaper off and dropped it into the pail. She then grabbed his underwear and tossed it to him so he could put it on himself.
"Alright... Out of that thing, I can walk normally again..." Jack murmured. "Now it's your turn, poopy-butt."
Jill nodded as she crawled onto the table and laid down. "Just... make it quick, okay?"
As Jack undid the tapes and pulled the diaper away, he realized that the smell was much more intense and vile than any of Isabelle's diapers, at least with his experience. "Sheesh, what did you eat?"
"Shush... Just hurry it up..."
He quickly grabbed the wipes and cleaned her off, resisting his sensitive gag reflex. Once he made sure her bottom was all clean again, he tossed them into the pail with the used diaper. He finished off by helping her off the table and presenting her with her panties. "M'lady."
"Heh... Thanks..."
Once the two were back in their normal clothes, Jack brushed off his jacket and said, "Okay, changing each other is gonna get some getting used to... but I can really see why Isabelle likes them. Comfy, convenient..."
"Yep. Could be nice to have around the Town Hall," Jill added.
Jack nodded and unlocked the door. "Okay, I think I've mustered up the confidence to take this bull by the horns..."
"So you're gonna talk to Isabelle about it?"
"It seems crazy, given her current state... but yes. I'm gonna do it."
He opened the door and stepped out to find Digby desperately trying to calm down a sobbing Isabelle. "Everything alright in there? I heard a lot of yelling..."
"No, no, everything's fine. We just... had a bit of an enlightenment, shall we say..." Jack nervously lied.
Digby gave him a skeptical look. "Are you sure?"
"Totally," Jill confirmed.
With a shrug, Digby continued patting Isabelle to calm her down. "I've been trying to stop her crying, but nothing is working out..."
"I can take her," Jack quickly said. "Trust me. Just set her down on the floor and get yourself a coffee or something..."
"Wha- O-Okay... You're acting really weird this morning..." Digby remarked as he was practically shoved out the door.
Jill stepped up and patted his shoulder. "It's fine. Erm, Mayor Jack is doing just fine. Say, this reminds me, we haven't had a chance to really know each other! I know Isabelle and Jack, but not you! Mind if I join you?"
"...Okay..." Digby agreed, still incredibly confused.
"Alright, have a nice time, you two!" Jack cheerfully said, escorting them out.
Once the doors were closed, he took a few deep breaths and dropped the happy facade. He slowly walked up to the puppy sitting on the floor. She stared back up at him with shy, almost scared eyes. He stared back the same way. Clearly the conversation that was about to follow would not be an easy one.