On The Road Again - Chapter 14

“Hold on, so you’re like, on the run basically?” Isla asked Jill as Jill tried to reach under Isla’s skirt.

“I guess so, yeah. Kind of exciting!” Jill said, brushing it off. Isla grabbed Jill’s hands and moved them away from her diaper.

“What are you going to do? You’ll have to go home at some point, right?” Isla asked.

“I don’t really want to think about that at the moment. I just want to enjoy this trip away, and maybe she’ll be more understanding when I get back.”

“That is if she doesn’t find us and take you home first!” Isla replied.

Jill shrugged. She was drunk, and Isla could tell she was probably ready to crash soon.

“Can I please change you?” Jill asked, almost begging. Isla sighed.

“Fine. But do a good job; I don’t want any diaper rash!” Isla conceded and grabbed another diaper from her bag. She handed all the materials to Jill, who was giddy to hold them. Isla removed all her bottoms and laid back on the bed on her back. She felt the slight crunch of plastic under her and smiled.

“What?” Jill asked, noticing her reaction.

“The hotel staff. They put plastic sheets under our beds.”

“Really?” Jill laughed. “Why?”

“I got caught trying to dispose of a diaper earlier while you were in the shower. Apparently, they want you to disclose incontinence so they can prepare the room. I think they even outfitted a dresser drawer as a diaper bin.” Isla pointed to her bedside table, and Jill walked over to it. She opened the bottom drawer and gasped with excitement.

“It’s like plastic lined and everything!” She said.

“Well, I guess we know where this one is going then!” Isla said while patting the front of her soaked diaper. Jill repositioned herself between Isla’s legs and removed the plastic tabs on Isla’s diaper. Isla blushed as Jill pulled back the padding, revealing her smooth-shaven pussy.

“Do you have wipes?” Jill asked. Isla nodded and pointed to her bag. Jill pulled them out and resumed her position between Isla’s legs. Jill pulled out the diaper from under Isla, wrapped it up and tossed it in the outfitted dresser. Then, she grabbed a wet wipe and began slowly running it over Isla’s crotch. Isla watched as Jill carefully cleaned her bits, then looked up to see Jill in completely unwavering concentration.

“You’re a virgin, right?” Jill asked quietly. Isla lightly recoiled from the question.

“Uh, yeah…” she replied, her cheeks burning brighter red and her body closing up more. Jill didn’t ask anything more. Once she finished wiping, Jill unfolded the fresh diaper and lifted up Isla’s hips towards her. Isla’s heart pounded, but she couldn’t help but be incredibly aroused. She felt the heat radiating from her core and her freshly cleaned pussy. Her eyes dashed down to Jill’s diaper as Jill leaned in to position the diaper underneath her. As she leant over Isla, their eyes met, and for a moment, there was a pause.

Jill continued, and Isla dropped her hips. Isla averted her eyes, not sure what she was feeling. ‘Probably the alcohol,’ she thought.

Jill covered Isla in baby powder, gently rubbed it in and then pulled the diaper over her crotch. She then carefully tapped Isla in, and when the diaper change was complete, she let out a heavy sigh.

“There. All done.”

Isla sat up straight and instantly felt woozy from the alcohol still running through her system. She wobbled and nearly fell back, but Jill caught her arm and pulled her upright.

“Careful!” Jill laughed, her face now inches from Isla’s. Another moment of heavy breathing and wondering eye contact passed. Isla licked her lips instinctually.

Suddenly, Jill pulled herself into Isla and planted a kiss on her lips. Isla pulled back, shocked.

“Jill…” she whispered, uncertain. Jill remained still, desperate to know what Isla would say next. But Isla didn’t say a thing; she just pulled Jill back in and kissed her back.

The kiss started to flow, and tongues began to fly. Isla laid back down, and Jill followed her, now laying on top of her on the bed. Isla moved her leg, positioned it between Jill’s thighs, and then pushed it up against her crotch. Jill inhaled with pleasure, then started to move her diapered hips against Isla’s leg. Isla grabbed her ass and encouraged the grinding, her pussy tingling with anticipation. Jill moved away from the kiss and pulled at Isla’s top. Isla aided her and removed her own bra as Jill pulled off her top, revealing her perfectly perky tits.

“Is this right?” Isla asked in the heat.

“If you like it, it’s right,” Jill replied. Isla pulled her back in.

The sounds of moaning and crinkling filled the room, until suddenly.

BANG. BANG. BANG.

An eruption of sound from the door stopped Jill and Isla, and the pair froze in place.

“Jill! Can we talk?” Kennedy called from outside.

“Shit!” Jill whispered, then got off of Isla, and the two began scrambling for clothes.

“Jill! Come on; I know you aren’t asleep yet; I can see the light on.”

“One minute!” Jill called out while putting her top back on. “Where are my bottoms?” She whispered to Isla. Isla shrugged and motioned for Jill to just wear her skirt. Jill grabbed Isla’s skirt and pulled it over her diaper while Isla put on her top and got her bottomless, diapered butt under the covers of her bed.

Kennedy kept knocking. “Come on Jill! I don’t have all night!”

Jill finally opened the door. “What.”

“Can we come in?” Kennedy asked, motioning to James, who was standing there awkwardly.

“No.”

“Fine.” Kennedy sighed. “I just wanted to say like, sorry.”

“Great. Bye!” Jill started to close the door, but Kennedy stopped her.

“I know, I know I’ve been a bitch,” Kennedy said, slurring her words and clearly even more wasted than before. “I think I’m just mad about mom, and I’m taking it out on you. You’re dealing with a lot, and I want you to know that I’m here for you.”

“Thanks…”

“No, seriously Jill, I’m here. That’s why I let you come because I’m like, trying to help you. Like I care so much, you know?” Kennedy staggered, but James caught her.

“Thank you, Ken, now go to your room. Isla and I are trying to sleep,” Jill urged. Kennedy leaned into the room to see Isla in bed and waved at her. Isla waved back, her hair a total mess.

“Okay, well, look. New start tomorrow. We’re back on the road bright and early!” Kennedy said.

“Bye!” Jill said, starting to close the door.

“Oh, but seriously Jill, seriously….” Kennedy started.

“Seriously, what?”

“No more… no more peeing your pants, okay?” Kennedy asked.

“Yeah, I don’t think we have to worry about that again,” Jill replied. “Goodnight Ken.”

“Goodnight Jilly, Goodnight Isla!”

Jill began to close the door before stopping and stepping outside.

“Hey! Asshole. Take her to her room and go home. Nothing else.” Jill warned James.

“I was gonna suck his dick!” Kennedy replied. Jill just glared back at her. “Fiiiiiinneeee.”

Jill finally returned to the room and closed the door. When she turned back, Isla had removed her top and pulled back the blanket, presenting herself in only a diaper for Jill. Jill removed her clothes and jumped in.