The Diaper Bet

Chapter 1: The Bet

Emma was practically bouncing with excitement as she welcomed her friend Olivia into her home. The two friends had been planning this baby-sitting gig for weeks, and finally, the big day had arrived. Or rather, the not-so-big kid would arrive soon.

Finally, having a break from college, the two of them couldn't wait to spend time together, and babysitting made the perfect storm. They both had time off, and neither of their parents would argue about such a good-willed idea, such as watching a little kid for a family friend, and best of all. He would be too little to be able to tattle on them as they had some fun girl time. Sure, they had to keep the little guy entertained, but that's what cartoons are for.

As they settled in, sipping coffee and chatting about their plan of attack (aka getting through the next few hours without losing their minds), Olivia suddenly zeroed in on the diaper bag sitting on the floor. "Hey, how old is this little guy again?" she asked, eyeing the assortment of diapers and other baby-like items with amusement.

Emma laughed and replied, "2 years! I'm basically his personal butler now."

Olivia's grin grew wider as she reached for the diaper bag, pulling out a random diaper to examine. "Wow, these things are huge!" She looked up at Emma with a mischievous glint in her eye. "Hey, you know what? I bet I can get you to fit into one of these."

Emma's smile faltered for a moment before she regained her composure. "Oh, no way, Liv! You think I could possibly squeeze myself into one of Timmy's diapers?" She chuckled, confident, knowing full well that a young adult like herself surely had to be too big for something meant for toddlers. "There's no way I'd even come close to fitting – I'm way too big!"

Olivia raised an eyebrow, intrigued by Emma's confidence. "Oh yeah? Alright, let me raise the stakes a bit. If you don't fit into one of these diapers, I'll let you call the shots for the rest of the night – no questions asked. I'll change all the diapers, get him all the snacks, anything and everything you want." She paused for dramatic effect with a mischievous grin. "But if you do fit... then you have to pee in it."

Emma's eyes widened in horror at the prospect. "Uh, no way! There's no chance that thing will fit me." Emma chuckled nervously.

Olivia's grin started looking less like amusement and more like genuine excitement for a real challenge to start off their fun weekend. "Then you have nothing to worry about. But I'm warning you, Emma – those diapers look pretty big."

Emma's eyes were fixed on Olivia, still trying to convince herself that there was no way she'd fit into one of Timmy's diapers. But the thought of actually wearing a baby diaper and needing to pee in it sent shivers down her spine.

"Make it the whole weekend." Emma wasn't about to risk something so embarrassing for just the evening. They only had Timmy for a few hours. No, if she was going to go through with this, she needed more than just a few hours.

"If she really thinks it'll fit, she'll go for it. Then I'll have her pay for the pizza this weekend AND start my history homework for next semester."

""Hmmmm..." Olivia paused, wondering if it was worth the risk. "Deal, but I get to video you wetting it."

"What! No way." Emma took a few steps back, horrified at what that level of blackmail could do.

"Hey, you're the one that wants to take something from a few hours, small and innocent, and turn it into the whole weekend. Besides, you're too big for it, remember? So you have nothing to worry about," Olivia mocked Emma, trying to push her buttons.

"Fine, fine," Emma said, holding up her hands in surrender. "You win. Deal. Let's just get this over with before Timmy gets here. If we got caught, we'd never be trusted to have a weekend alone again."

Olivia let out a squeal of excitement and quickly started preparing the diaper. She grabbed some wipes and cream from the diaper baby. "Okay, 'baby' needs her diaper changed!" Olivia grinned, confident in her abilities.

Emma giggled nervously at Olivia's overly excited demeanor.

"I might have just made a huge mistake." Olivia began to peel off Emma's skirt and underwear, much like she would with a real baby. Olivia carefully cleaned Emma's bottom, then slapped on a generous layer of cream.

"Liv, you don't have to use that stuff you know! It's not like I'm a real baby needing their butt protected from rashes or anything." Emma rolled her eyes annoyed on how far Olivia was taking this.

"Oh, relax, I'm just having a time of fun. Now, time for the diaper, baby!" Olivia cooed, picking up one of the enormous diapers and holding it out so Emma could see the design. Unfolding the diaper, revealing how large they really are.

"Alright, lift your butt, I need to get this under you." Olivia giggled, enjoying every moment of their silly bet.

Emma felt a flutter in her chest as Olivia placed the diaper under her, ensuring it was centered.

"Good girl! Now, back down." Olivia genitally pushed on Emma's waist, one hand guiding it back down. "The moment of truth." Olivia swiftly pulled up the front of the diaper and began stretching the sides, trying to get them to wrap around Emma's large waist.

"Ha! See, there's no way it'll fit." Emma felt a little more confident seeing Olivia struggle to get the first tape in place.

"Hold your horses; these things stretch. Now, lie back down. I got a bet to win" Olivia pushed Emma's chest backwards so that she was laying flat once again.

"It's not going to work," Emma mocked Olivia.

Oliva just focused on getting the tapes in place; she pulled one side, stretched it, and placed it to its limit into place. Holding it briefly. To her shock, it stayed. "Ha! One down." Emma's heart skipped a beat, as she felt the snug tape stubbornly staying in place.

"Yeah, but there's no way the other one stays. Like, I have to be able to stand up with this thing on for it to count." Emma had to find a loophole; otherwise... she might have to pee in a diaper for the first time in over 14 years!

"Ugh! Fine, but this is going to work" Olivia started to stretch the other side. Pulling and tugging at the tape, trying to get it to reach. Then, finally, it did! "Shit!" This is going to work," the first tape snapped back into place.

"Told you, my butts are too big" Emma grinned; she was so close to winning this bet.

"No, it's not." Olivia pulled the tape back into place, holding both sides in place for a moment ot ensure they would have some sticking power.

The tapes seemed to be holding, and Emma held her breath. The diaper seemed... snug. But still, surely there was no way it could possibly fit...

Then Olivia stepped back to admire her handiwork. Emma looked down at herself in horror as she realized that the diaper did indeed fit – but just barely. It was stretched taut across her bottom, and if she shifted even an inch, it felt like it might fall off. She hoped that as she stood up, it would just fall righ off, but it didn't. It held on.

Olivia let out a triumphant shriek, pumping her fist in the air. "Yes! You're so busted, Emma! I knew it would fit you. You're such a baby."

Emma's face went bright red as she stared at herself in the mirror in the living room. She couldn't believe she'd actually managed to squeeze into one of Timmy's diapers. It was absurd... and yet, here she was.

The sound of a car driving by broke the spell, and Emma's eyes snapped to the clock. "Oh no, Liv – Timmy will be here any second! I have to get out of this thing"

Olivia grinned mischievously, holding onto Emma's panties. "Yeah, yeah... but first, we have a little bet of our to settle."