Story Nook Posted September 7, 2024 Posted September 7, 2024 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 pulling up outside broke the spell, and Emma's eyes snapped to the clock. "Oh no, Liv – Timmy's here! 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." 5
Story Nook Posted September 14, 2024 Author Posted September 14, 2024 (edited) Chapter 2: No Fair! "Come on, Liv, you can't be serious." Emma crossed her arms, annoyed at Olivia for not giving her back her panties. "Can't we settle this later? Timmy's mom is about to knock on the door any second, and I can't go answering it like this." She gestured, her arms showing off her current state in just a grey T-shirt and a diaper. "No way! The bet was if you fit, you had to pee it, and I get to video it. Now hurry up. If you're quick, you can change out of it before Timmy gets to the door." Olivia stood her ground with a grin on her face. She was always a little rebellious and liked to push things a little too far. That's why Emma's parents didn't really like her that much. But they were both adults now, so it's not like her parents could do much about it. "Ugh! Fine." Emma rolled her eyes and tried to change her focus to her bladder. She just wanted to get this over with so she could get changed. The last thing she wanted was to wear this diaper any longer than she had to. But peeing herself on purpose was more challenging than she thought. She felt a flutter in her chest as Olivia pulled out her phone and started videoing her. "Okay, okay... I'm trying," Emma muttered, trying to sound braver than she felt. Olivia giggled. "Alright, let's get this show on the road!" Emma felt the first drops start to trickle down. She closed her eyes, mortified, as the warm liquid hit the soft diaper. "Oh my god, this is so gross," Emma whispered, trying not to make a sound as she peed into the diaper. "Oh my gosh, you're doing it!" Olivia exclaimed, laughing while zooming in on the action. "Is it going to be able to hold it all?" Emma felt her face heat up with embarrassment as the pee started to pool inside the diaper, spreading across the front and back of the diaper. She could feel it seeping slowly, soaking it all up. She was mortified. "I don't know; it's pooling at my butt. This is so gross, Liv! Why did I agree to take this stupid bet?" "You're the one who thought it wouldn't fit. Besides, apparently, me needing to do what you say was worth the risk," Olivia smiled. But now I don't have to. Instead, I have to help watch two babies," Oliva giggled. "How did I let this happen? How long is this going to take? It feels like it's going on forever," Emma groaned, trying to speed things along. As the peeing continued, Emma couldn't help but feel a sense of disgust and amusement at herself and her body. Who would have thought that she'd be peeing into a diaper? It was like something out of a bad dream, and yet something totally stupid and silly that she would never live down. Finally, after what felt like an eternity, the flow slowed to a trickle and then stopped altogether. "There! Happy?" Emma snapped at Olivia. But Olivia just moved closer to get a few different angles. "Very! I'm shocked it held up." She turned off the video and reached out to feel how wet the diaper was. "You really soaked this thing." "Yeah, well, they aren't meant for grown women to use, " Emma said, annoyed. "Now, can I have my panties back, please?" But before Olivia could say anything, they were interrupted. *Ring* *Ring* "Oh no... oh no... NO," Emma muttered, panic setting in, as she looked at her phone seeing the caller ID "It's Timmy's mom. I needed some more time. I'll... uh... change after she hangs up." Emma quickly threw on her skirt, covering the soiled diaper worried that she might have to answer the door before the call ends. "Quick, finish cleaning up the place real quick while I answer this." Olivia was about to protest, annoyed that Emma was telling her to do stuff even though she had lost the bet. But then, an evil thought crossed her mind. "Okay," she grinned, grabbing the random clothes and laundry scattered about in the living room. She snuck off to Emma's room, where she quickly raided Emma's underwear drawer and gathered up all of Emma's panties. She smiled mischievously as she stuffed them into a laundry basket and carried it to the laundry room. There, she tossed all of the panties into the washer. Meanwhile, Emma answered her phone and started chatting with Timmy's mom, praying she wasn't anywhere close by. "Hi, Karen! What's up?." She asked, trying not to let her nerves come through on the call. "Hey Em! I hate to do this to you, but I need to cancel" Karens words felt like a ton of bricks off of Emma's shoulders. She was mortified at the thought of getting caught not only wearing a toddler's diaper, but a wet one at that. "Timmy isn't feeling well, and frankly, this day has been a mess. We're just doing a day in instead. Taking time to just watch movies and stuff." "No worries Karen! I'm sorry to hear Timmy isn't feeling well." Emma had to try to hold back her relief. She wanted so badly to let out a sigh, but didn't want to send the wrong message that she didn't want to watch Timmy. "I hope he feels better soon, and you and your husband get to have some chill time this weekend." "Thanks Em. I hope so too. I really am sorry about cancelling. If you need, I can still pay you at least for an hour for the time I caused you to waste?" "Oh no, you don't have to do that." Emma really wanted the cash. She was planning on using some of it for the pizza this weekend, as well as some fun money for the weekend with Olivia. But she also was too nice to accept money like that without working for it. "I really don't mind Em, I know you are busy with college and stuff. I don't want you to lose out on the little bit of time you do get. I've been there and done that." Emma was starting to shift a little uncomfortably. The longer she talks, the longer she had to stay in the soaked diaper. The weight of it makes her skin crawl. She couldn't believe the stupid thing fit on her. "Thanks Karen, but I really can't do that to you. I actually invited Oliva over to help, so I already got some company, this just means we can start doing some fun stuff a little sooner is all. I really appreciate the offer, but we're good. I promise" Emma knew Olivia would be pissed that they weren't making any money this weekend, but she would just have to deal with it, it's not like she was going to make anything anyway if it wasn't for Emma. "Alright, we'll you two girls have fun then. Just not too much fun. I don't want to be hearing about anything on the news." Karne chuckled, knowing the history the girls had, and how bad of an influence Oliva could be at times. Emma giggle back, "We won't. Thanks Karen." Emma ended the phone call relieved she wouldn't have to face anyone while wearing the diaper. Plus know her weekend was freed up. As soon as she ended the call, Olivia emerged from the laundry room, looking annoyed. "We aren't getting paid?" she asked Emma, rather angrily. But Emma's patience had worn thin. She rushed over to Olivia with an annoyed expression. "That's nothing, I had to pee in a diaper, and then have an entire conversation with the women who babysat me as a kid. Do you have any idea how embarrassing that is?" she softy yelled at Olivia for making her pee the diaper, and videoed the whole thing, when they thought Timming was right around the corner. Olivia held up her hands, apologetic. "Hey, hey! Don't be mad. It's your fault for taking so long." She grinned. She could have pushed it off, but she knew Emma would have just tried to get away without peeing it, and that wasn't any fun. "Tell you what, to make things fair... I'll do all the diaper changes this weekend," she said with a mischievous grin. Emma raised an eyebrow, "That doesn't even make any sense. We aren't watching Timmy anymore. Now, give me back my panties. I really want to get out of this thing." Emma was frustrated about what took place, but she wasn't about to let it ruin her weekend. Olivia pretended not to know anything about the missing underwear. "Panties? I don't have them," she said innocently. "Come on, Liv. This isn't funny. Give me back my underwear." Emma's eyes narrowed annoyedly as she placed her hands on her hips. "I'm serious. I don't have them." Olivia giggled. She turned her pockets inside out, and twirled around, showing she didn't tuck it into her jeans or anything. "Ugh! Liv!" Emma stormed off to her room to find a new pair of panties. But when she opened her drawer, she found that all of her undies were gone. "Olivia! You bitch!" she shouted, storming out of the room. "Where are they!" "Where are what?" Olivia giggled, enjoying how well her plan seemed to work. "My underwear, what did you do with them?!" Emma couldn't believe Olivia would stoop this low just to mess with her. "I don't know what you are talking about. I just cleaned up like you had asked." Olivia glanced back at the laundry room, where the washer machine was running. "You didn't..." Emma stormed off into the laundry room, searching through the basket of clothes, and pile of dirty laundry, looking for any pair of underwear. Anything would be better than wearing a diaper or going commando. She knelt down to look in the dryer, praying that there would be at least one pair of clean of underwear. But was instead greeted by the uncomfortable cold squishing of the soaking diaper against her. To make matters worse, there was none in the dryer. Reluctantly, she side stepped over to the washer, where it was clear to see, every pair of underwear she owned, swirling around getting cleaned. Even her thongs, and sexy panties she kept for special occasions, all, swirling around now mocking her. "Oh... I'm sorry, did the baby need a change?" Olivia mocked. "This isn't funny Liv." Emma stood up annoyed. "Oh relax. I'm just having a little fun. I was hoping to at least get paid for babysitting, but this works for me too." Olivia smiled giggling, as she looked at Emma. Edited October 6, 2024 by Story Nook Removed little Timmy from the story 6
Story Nook Posted October 10, 2024 Author Posted October 10, 2024 Chapter 3: Raising the Steaks "Liv, you jerk!" Emma stormed out of the laundry room, determined to find something else she could wear under her skirt. Even going without underwear would be better than this. She dug deep in her closet, trying to find a pair of her secret underwear she only wears on dates, unaware that bending over put her diaper on full display under her skirt. Oliva couldn't help herself. Everything about this gave her more ideas on how to mess with her bestie. Olivia pulled out her phone and snapped a few more photos to match her video. She wanted to keep this going, but how? Then it struck her: the perfect way to mess with Emma. Olivia stepped out of the room and snuck across the hall to the bathroom. She grabbed the spare keys and locked the bathroom door closed. "This is too perfect. Without toilet access, she'll have no other choice but to wear another diaper." Olivia returned to the living room and began looking through the diaper bag again. She needed to get everything ready for the 'baby's' diaper change. Looking through the bag, she came across something she hadn't seen before. It looked like a pill bottle but much larger. Reading the label, Oliva grinned. "Oh, this is too good." Olivia set aside everything she needed for the change, including her little surprise, and returned to Emma's bedroom door. "You aren't going to find any." Olivia taunted. "You are such a bitch you know that." Emma smiled back at her. She was frustrated, but she also enjoyed Olivia's antics; that's why they became such best friends. "Yeah, but you still love me." Olivia leaned up against the door frame, enjoying making her friend squirm. "That doesn't change the fact that there is no way you will get me to wear another diaper." Emma walked towards the door, wanting to take the diaper off and throw it away in the trash. "Wanna bet?" Olivia smiled devilishly, blocking the doorway. "Ha! As if. Betting with you is what got me in this mess." Emma lifted her skirt, showing off her diaper. "I think I'll pass. Thanks." Emma rolled her eyes, trying to push past Olivia, but she stood her ground, blocking the doorway. "I tell you what. Let's make another deal. If I get you to wear another diaper willingly, I get to call the shots for the rest of the weekend. But until I do, I'll wear one, and if you don't wear another diaper for the rest of the day, you can call all the shots." "What? No way. There is no way you will get me to wear another one." Emma hated the idea of wearing another diaper. "Oh, come on." Olivia wined. She had to get Emma to wear another diaper; she just had to try that prank she thought of. "How about this: I'll follow the same rule if we get a diaper to fit me. I'll have to wet it, and you can video it." Olivia paused, looking at Emma with confidence. Then we would both have something on the other. "You can't be serious." Emma couldn't believe Olvia was willing to wet a diaper. She had to be bluffing. There was no way. "Fine, but you have to do it using the next size up, not this little thing." Emma wasn't going to let Olvia off the hook that easy. If she was going to have Oliva wear a diaper, it was going to be one that actually stood a chance of fitting her. "There are bigger ones?" Olvia giggled, covering her mouth. She hadn't even noticed them. That meant her plan was going to work even better than she imagined. "Uh yeah! I babysit kids of all ages. This is a size 5. They go up to size 7, and then even bigger ones for special needs kids." Emma realized her mistake too late. If she managed to fit in this one, then that meant the others would likely fit even better. "Shit, why did I tell her that?" "Let's get this over with then." Olvia moved out of the way so they could go back out to the living room and get this taken care of. She needed to distract Emma after she got her video and had the perfect excuse to do so. "Hey, given we have to wait for your underwear to dry before we go out, do you wanna watch a movie or something?" Even if she was messing with her friend, which was still a part of the plan, she still wanted to have fun with her. It's not often they get to do this kind of stuff, not since college started. "Haha, Sure." Emma followed Olivia back out into the living room. "First, let me throw this silly thing away." Emma was starting to feel a little better about the whole situation. Sure, Olivia crossed the line, but it was Olvia; Emma should have known she was going to pull something as stupid as that. Emma walked over to the trash can in the kitchen and removed her soaked diaper. She was left without any underwear, which is fine for now. They were going to watch a movie and chill, so she didn't need it. "Awe! No fun, here I thought we would be soggy girls together." Oliva teased. She didn't care about the whole diaper thing. She thought it was silly and stupid, but it was clearly something Emma didn't like, and that made it a little more fun. "Hell no! This thing is gross. If you like it, that's your provocative." Emma threw the diaper in the trash with a loud thud from the weight of it. "Now, let's get that butt of yours diapered!" Emma skipped over to the diaper bag, excited to get a little revenge. "Come on, your turn, lay that booty down!" Emma tapped on the ground next to her with all of the supplies. "Alright." Olivia didn't mind their little agreement at all. She knew that if things went according to plan, she would rule the weekend, and they would laugh about this later. Olvia more than Emma. Each time Emma thinks back to this weekend, she'll want to die of embarrassment. Olvia swiftly removed her jeans, followed by her panties, as she lay down on the ground. "Now, don't think you can just steal my underwear." Olvia teased. "Eww. Gross. First off, there's no way I would do that. Secondly, there is no way my tiny butt would even fit in those things." Emma had to make fun of Olvia a little bit, but it was only a fair game. "Ha Ha." Olvia fake laughed. "Just get this over with; your carpet is super uncomfortable." Olvia shifted slightly after her lower back hit the ground. "Fine." Emma pulled out one of the larger diapers, still opting to go with one of the size sevens. She didn't want to have to get into the pull-ups if she could avoid it. Using tape-ons meant she at least stood a small chance on the sides stretching enough to get securely put in place. Being an expert babysitter, Emma had no trouble getting the diaper on Olvia. "See, I know one of these ones would fit you. Emma sat back, admiring her handy work. "Fuck." Olvia looked at the diaper, annoyed that the bigger ones barely fit. "Fine, a deal's, a deal." She stood up, and looked at the diaper a little closer. She was worried the thing was going to go flying off with how tight it felt around her waist. "You have to wet it. Remember?" Emma wasn't going to let Olvia off the hook. She made her wet it, so it was only fair she did the same. "I know." Olvia had an easier time opening up the floodgates and wetting her diaper, practically doing it right away. "Whoa! Wait, I need to record it." Emma stumbled, trying to grab her phone to get a recording. "Well, hurry up, I'm not about to stop." Olvia giggled as she was about to finish up. Emma managed to get her phone out just in time to capture a few seconds of Olivia's 'accident' as she finished wetting her diaper. The sound of Olivia's giggles and the sloshing of the diaper filled the air, and Emma couldn't help but laugh at the absurdity of it all. "Ah ha! Got it!" Emma exclaimed, holding up her phone to show off the recording. "Now we're even!" "Good. Now, if you'll excuse me, I have a diaper to get out of." Olvia started to walk toward the kitchen but felt the pee that had pooled in her diaper begin to shift, causing her to waddle a little. "How long does it take this thing to soak it all up?" Olvia asked while waddling over toward the trash can. "Don't ask me; you're the one who peed so much." Emma couldn't help but giggle. Now she understood why Olvia seemed to enjoy the idea of her being stuck in the diaper longer. It was kind of funny. "Shit!" Olvia froze when she entered the kitchen; she felt a small trickle running down her leg. "What?" Emma stood up, approaching Olvia. "The damn thing leaked." Olvia started to laugh uncontrollably. The whole thing was too funny. Funny and stupid. Why had she even thought of making this silly bet in the first place? Emma joined in the laughter. "Should I get a mop?" She laughed harder at the thought of her college friend leaking her little diaper. "No, I think it got the rest. I don't feel the pool anymore." Olvia waddled the rest of the way over to the trash without anything else running down her leg. She ripped off the diaper and tossed it in the garbage with a loud thud, much louder than Emma's. Olivia quickly wiped her legs off with some wet paper towels, tossing them in the trash, all the while laughing and teasing Emma about being a 'good babysitter' and wanting to help out with a leaky diaper. She grabbed some snacks from the kitchen, along with some drinks for the two of them, before returning to the living room, where Emma was waiting with Olvia's panties in one hand and her jeans in the other. "Trade ya for the soda?" Emma taunted. "Deal." Olvia giggled. That was her plan in the first place. Have Emma drink the soda so she'll need to pee. She'll have to ask for another diaper with the bathrooms locked and no other option. The two friends settled in on the couch, with Olivia pulling her pants back up and Emma handing over the remote control. "Okay, what movie do you want to watch?" Emma asked, scrolling through the options. "How about something sappy and romantic?" Olivia suggested, winking at Emma. "I need some serious feel-good vibes after this diaper debacle." Emma raised an eyebrow, laughing. "You're such a sucker for rom-coms, Liv." Olivia shrugged. "Hey, someone's got to keep the mood light around here." As they settled in to watch their movie, Emma couldn't help but think about how much she loved spending time with Olivia, even if it meant enduring some embarrassing moments like this one. "You know, despite all the crap you put me through today," Emma said, smiling at Olivia, "I'm still having a pretty good time." Olivia grinned back, her eyes sparkling with mischief. "That's what I'm counting on, Em. Now, let's get this movie started!." 1
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