Kathryn had already found the clothing room on her own, she led Natalie there without needing to ask the way. Once in the room she turned to Natalie and grinned at her.
“You look like you were really having fun!” She nuzzled her girlfriend’s nose. “Feeling better?”
“Yeah, I guess.” Natalie smiled shyly. “I mean, it’s still REALLY weird, but yeah… That was fun.”
“Good!” Kathryn sighed happily. “I was worried about you. And look at this outfit, you are super cute.” Natalie did a little curtsey in response.
“Though you do have cock-breath.” Kathryn smirked.
“You bitch.” Natalie stuck her tongue out at Kathryn.
Kathryn laughed, and started browsing the clothes. “I think the really weird is what you like. I didn’t realize you were so kinky all this time.”
Natalie squirmed, deliberately squishing her legs around the pullup. It felt strange. Bulky, damp, and ever-present with the plastic pants hugging it to her body. She felt her nipples harden, couldn’t decide if her blush was desire or embarrassment.
“I don’t know. This is all really new. It’s hard.” Natalie sighed.
“You know what was hard was Richard.” Kathryn chuckled, and Natalie couldn’t help but join in. “He’s obviously a big fan.”
“Yeah, he likes it when I’m embarrassed.” Natalie dug around in the drawers, hoping to find some makeup.
“I didn’t realize it, but I like it when you’re embarrassed too.” Kathryn said.
“You do?” Natalie asked curiously.
“Yeah, like I said, I didn’t realize it before.” Kathryn tried on a clingy red top. “But you know I like teasing you, especially in public. I think I like embarrassing you. Maybe because it made it easier to turn you on.”
“Meanie.” Natalie couldn’t disagree, but she wasn’t sure it was just the embarrassment. Maybe the pullups had something to with it too. Or maybe they were just the most embarrassing thing she’d ever experienced.
“So have you explored this place much yet?” Kathryn asked, sliding herself into a short black skirt.
“Some of it.” Natalie pushed the drawers closed, plenty of accessories but no makeup. “It’s huge.”
“Yeah, this is going to be amazing!” Kathryn stepped over to Natalie and tucked some hair behind Nat’s ear. “You think maybe we could do more than just the first month?”
“Maybe.” Natalie looked away shyly. “I’m still getting used to it. You’re not the one in pullups!”
“And you’re not the one in chastity.” Kathryn stuck her tongue out at Natalie.
“Maybe I’d feel better about it if you let me change.” Natalie said mischievously. “I’ll put the plastic pants back on, but at least let me get a clean pullup.”
“And then when our Master finds out, I’m the one in trouble and I have to wear this belt for the next week?” Kathryn jingled the belt under her shirt. “No way!”
“Aww, come on Kathryn.” Natalie pouted. “I’ll make it up to you. I’ll um….”
“Go down on me?” Kathryn looked down at Natalie, hands on her hips. “How you gonna do that through the belt?”
“I was trying to figure something else out!” Natalie pouted. “Or you could just do it because I’m your girlfriend and you love me?”
“I do love you.” Kathryn said, kissing Natalie on the end of her nose. “But nothing is hurting you, and you’ll probably just end up loving it so no.”
Natalie sighed, frowning when Kathryn bapped her nose.
“If you’re so concerned, let’s get you to your next change faster.” Kathryn said, grabbing Natalie’s hand and leading her away.
“How?” Natalie said, as she was pulled along. “And you don’t have to grab my hand every time!”
“You’re right.” Kathryn said, “I should get a leash.”
Natalie had no response to that, just a little heat between her legs.
“Here you are!” Kathryn said, motioning to the kitchen as they arrived. “Plenty of water here, let’s pour you a big glass.”
“That’s your plan?” Natalie grumped.
“It’s going to happen sooner or later.” Kathryn said. “Course, if you hold off, maybe you won’t need to go until we’re already at the club. Then you’ll be wearing that wet pullup down there.” She poured a large water glass, held it out to Natalie.
Natalie’s eyes went wide in horror. “Fine, you win.” She took the glass from Kathryn and took a few big gulps.
“Drink it all down sweetie.” Kathryn said, smirking. “Then I’ll pour you a second glass.”
Natalie’s only response was a glare.
“In the meantime, let’s check out the balcony!” Kathryn bounced on her toes.
“There’s a balcony?” Natalie asked.
“Oh yeah!” Kathryn said. “A huge one!” She reached for Natalie, then stopped short, grinned.
Natalie rolled her eyes and held out her wrist to be grabbed.
On the other side of the living room, past what looked like an art gallery, a door let them out onto a gardened balcony. Steppingstones wound across green grass, between trees and shrubs in large pots.
Kathryn wiggled her toes in the grass in delight, then jogged over to the railing. Sturdy metal bars framed glass panels at waist height. Natalie lagged behind, taking gulps of her water. When Kathryn leaned over the rail to look down the building, her stomach lurched! She had to sink to her knees to keep from falling over.
Kathryn turned and leaned against the balcony. “You fall?”
“Be careful!” Natalie said. “I can’t believe you just leaned over that.”
“I can’t decide if you’re a big baby or an old lady, all worried about that.” Kathryn teased, walking over to Natalie. “Oh wait, I bet if I lift up your skirt I’ll be able to decide…”
Natalie blushed, frustrated that she could still be embarrassed by being teased that way. “Shouldn’t I be used to those jokes by now? They’ve been making them all day.”
“If I was really a baby I’d cry until you changed me.” Natalie managed, then finished off her drink.
“Ooh, now you’re getting into it.” Kathryn plopped down on the grass next to Natalie. “I’m glad you’re having fun.”
“I’m not sure it’s fun.” Natalie said.
“But it is hot.” Kathryn said, reaching over and pushing Natalie down on her back. She straddled her girlfriend, hands to either side of Natalie’s head.
“Yes.” Natalie whispered.
“What was that?” Kathryn said. “Louder.”
“Yes.” Natalie said quietly, looking away.
“Yes what?” Kathryn pressed.
“Yes, it’s hot.” Natalie squirmed on the grass.
“Wetting yourself is hot?” Kathryn asked relentlessly. “Having your girlfriend and your master change you is hot? Walking around in wet pullups is hot?”
Natalie shut her eyes, whimpering. She nodded, then managed. “Yes Kathryn. All of those things are hot.”
Kathryn grinned, and grabbed Natalie’s wrists, pinning her. She lay down on the other girl, kissing her deeply, exploring Natalie’s mouth with her tongue.
“Surprisingly, it’s hot for me too.” Kathryn said as she pulled back. “Or maybe it’s surprisingly hot. Either way, better not get too worked up with this belt on.”
“Why not?” Natalie’s eyes flashed mischievously. She reached up and cupped Kathryn’s generous breasts, gently stroking them through the shirt. “Would that be so bad?”
Kathryn moaned, then bit her lip. “Stop that, you know I can’t do anything about it.”
Natalie giggled. “Well there’s lots of things you can do. You can kiss me, play with my tits. You can strip me naked.” She wriggled under Kathryn. “Oh, I guess you will soon, when you make me wet myself again. You’ll have to strip me down and change me.”
Natalie’s heart thudded. Despite her bold words she was getting embarrassed again. Teasing Kathryn was enough fun to keep her going, otherwise she was sure she’d stutter to a stop.
Kathryn moaned again, pulled away from Natalie slowly. “You’re terrible! You know I can’t get off like this.”
Natalie sat up, rolling over on top of Kathryn as she tried to escape. “I’m not terrible, I’m just turned on. I want you, Kathryn.”
It was true, Natalie realized, she wanted nothing more than to make out with her girlfriend… in the pullup, not despite it.
“You are going to be in big trouble if you keep this up.” Kathryn squirmed out from under Natalie.
“Oh yeah?” Natalie clung to Kathryn, burying her face in her girlfriend’s breasts. Kathryn shuddered and lay back for a moment which gave Natalie time to get under her top. For a few minutes Kathryn lay there, moaning and squirming, until Natalie got her mouth around one of Kathryn’s nipples.
“Oh god no.” Kathryn groaned and reluctantly forced herself out from under Natalie. “Damn you, I can’t get off in this thing.”
“Have you tried?” Natalie grinned cheekily, kicking her feet in the grass.
“Yes!” Kathryn sighed. “He made me try a couple of them until we found one that fits so I can’t feel anything.”
“Oooh, he’s sneaky.” Natalie pulled her skirt up and rubbed her pullup. It was nothing compared to the vibrator, but it felt good. She was warm, and wet from more than just her earlier accident in it.
“Oh no you don’t.” Kathryn said, hopping to her feet. “You are not going to get off while I’m stuck.”
“So stop me.” Natalie slid a hand inside her pullup, closed her eyes and moaned.
“I think maybe you forgot how things used to go.” Kathryn said. She grabbed Natalie’s shoulders and twisted her around onto her belly. With strength that always managed to surprise Natalie, she pulled the smaller girl over her lap. “Just because we have a new Master doesn’t mean you and I are on the same level. You’re still my sub.”
Natalie squirmed, making no attempt to get off Kathryn’s lap. “Really?”
“Yes!” Kathryn stroked Natalie’s hair. “Were you really worried about that?”
“Maybe a little.” Natalie looked down.
“I’m sorry sweetie.” Kathryn said. “For letting you worry about that, and for how your ass is about to feel.”
“Wait, what?” Natalie protested, but it was too late. She felt Kathryn yank her stockings, plastic pants, and pullups down in one quick motion.
“OW!” Natalie cried out as the first spank came down on her ass. “That’s way harder than you normally start!”
“You have been a very naughty girl in the last ten minutes.” Kathryn said. “I told you that you were going to get it.”
Natalie whimpered, and braced for the next strike.
When it came, it came with friends. Kathryn smacked Natalie across one cheek, then the other, raining spanks down until her own hand stung. Natalie cried out with each smack, then her cries became blubbering. Kathryn rubbed her hand in the grass to cool it.
“Starting to realize that what you did was bad?” She asked.
“Yes mistress…” Natalie looked over her shoulder anxiously. “What do you mean by starting?”
“I mean we’re at the halfway point.” Kathryn said, arching a brow.
“Kathryn, I mean Mistress, please, no…” Natalie whimpered, sniffled.
“Here it comes!” Kathryn raised her hand and began spanking again. Blow after blow after blow, turning Natalie’s smooth pale cheeks rosy, blushed, then deep red.
By the time the second round stopped, Natalie was softly crying, hands gripping the grass.
“Are you sorry for what you did, Natalie?” Kathryn asked, gently stroking the girl’s tender ass.
“Yes Mistress.” Natalie nodded vigorously.
“Are you going to be a good girl for a while?” Kathryn continued.
“Yes Mistress!” Natalie looked back worriedly.
“Yes dear, your spanking is done.” Kathryn brushed some tears from Natalie’s cheek. “Let’s get you fixed up. I’m sure there’s some diaper cream or something around that will soothe your butt.”
Natalie blushed deeply. With all the sass knocked out of her, she felt the embarrassment burn her again. It got worse when Kathryn walked her back to the diaper room with her pullups still pulled just below her rear. Worse again when Kathryn bent her over the changing table and spread lotion over her cheeks.
The lotion did feel good though, spreading cool over her burning cheeks. The spanking had done nothing to cool her down between her legs, and the lotion only got her more excited. She hoped Kathryn would keep going, even wiggled her rear a little, but knew better than to express her frustration when Kathryn pulled her pullup and the rest back up.
“Now, let’s get you ready for tonight.” Kathryn said.
“What do you mean?” Natalie asked.
“You still want a change before we go clubbing, right?” Kathryn ruffled Natalie’s hair.
“Oh, another glass of water?” Natalie sighed.
“No.” Kathryn said. “Three more. Don’t pout! You want to be changed before the club or not?”
“Yes Mistress.” Natalie nodded.
With three full glasses of water, they settled down in the media room. Kathryn let Natalie pick the YouTube videos, but only if she drank a quarter of a glass for each one. After the first couple, Natalie started picking longer and longer videos. Even so, she was uncomfortably full by the time the twelfth video wrapped up.
“Ugh, now I’m sloshing.” She complained.
“The best thing to get rid of that feeling is a walk.” Kathryn said.
“We can’t go out!” Natalie protested.
“No silly.” Kathryn smiled. “Around the penthouse. We still haven’t seen the whole thing.”
“Oh.” Natalie nodded. “Okay.”
“First stop is the toy room.” Kathryn said. “I do want to get that leash.”
Natalie stuck her tongue out at Kathryn, but followed happily along, picking out a matching leash for her collar. When the metal clasp clicked across her collar’s ring, she relaxed a little.
“Kathryn is in charge, I don’t have to worry.” She thought.
The first hallway they tried was mostly rooms they’d already seen, though there were a surprising number of guest rooms now that they had the presence of mind to count them. Each had its own bathroom, which Kathryn gleefully pointed out to Natalie.
“Let’s leave the art gallery for later.” Kathryn said. “Looked like there was some really cool stuff in there, I’d rather take my time.”
“Okay.” Natalie smiled, sticking close to her girlfriend. “I saw a library over by the office.” She pointed.
“Oh, I haven’t been down that way.” Kathryn tugged playfully on the leash, Natalie scampered along behind.
They found the library easily enough, as well as a wine storage room, a big formal dining room, and a laundry room. Kathryn paused in the latter and tugged on Natalie’s leash.
“This will be handy I bet.” She grinned. “For cleaning up your clothes. I bet your clothes from last night are in here somewhere.”
“Stop it.” Natalie squirmed. Her bladder was already bothering her, but she still couldn’t bring herself to just casually wet.
“Well they’d have to be.” Kathryn backed Natalie up against the wall. “Your shorts and panties were positively soaked.”
Natalie looked away, squirming some more. “You’re the one making me do this.”
“I wasn’t the one that made you wet yourself last night.” Kathryn retorted. “In the elevator, or in the bed after our Master put a pullup on you.”
Natalie blushed scarlet, unable to respond. “It’s true, I did wet myself. In the elevator apparently. And I peed myself in my sleep.”
“That’s what started this whole game.” Kathryn said, grabbing Natalie’s chin and forcing her to look up. “You’re the reason you’re wearing a pullup right now.”
“I was really drunk!” Natalie whined.
“You never let me off the hook for things I do drunk.” Kathryn reminded her. Natalie looked away again.
“How’s your bladder?” Kathryn reached down and pressed on Natalie’s abdomen.
“Hey, stop!” Natalie whined. She felt a trickle get loose, but managed to stop herself.
“Already huh?” Kathryn grinned. “Don’t worry, I won’t force you. But the longer you wait the more wet you’re going to be.”
Natalie reached down to stroke her pullup. Her face flaming, torn between embarrassment and a desire to feel that pleasure again. “She’s right, but I just can’t do it. I can’t just go in my panties… or pullup, whatever.”
“Oooh, are you putting on a show?” Kathryn said.
“I thought you told me not to.” Natalie retorted, pulling her hand away from her crotch.
“That was then. This is now, and a LOT closer to when I will hopefully get my belt off.” Kathryn tugged the leash, and pulled Natalie into the hall, looking for a suitable location. She settled on the living room, pulling Natalie over in front of one of the huge windows.
“The next thing you are going to do, sub, is sit down and pull up your skirt.” Kathryn said in a stern tone. “Then you’re going to play with yourself through those plastic pants until you either come or wet yourself.”
“Ka-…” She bit her lip when Kathryn frowned. “Mistress, please don’t make me.”
“Oh, I am making you do this.” Kathryn leaned in, looking Natalie closely in the eyes. “Do you understand, sub? I am making you do this.”
Natalie shivered, and nodded. Some of the paralyzing embarrassment receded. “Kathryn is in charge.”
Slowly, Natalie kneeled down. Kathryn detached the leash. “All the way on your butt, sub.”
“Yes Mistress.” Natalie sat, spreading her legs and gathering up her skirt. She looked down at her crotch. Spiderweb stockings spread across bright red plastic. She could feel the bulk of the pullup pressing against her. It felt a little damper.
“That might have been more than a few drops.” She thought. “Or maybe my pussy is just that wet…”
She swallowed hard and looked up at Kathryn. Getting a nod from her mistress, she started rubbing. At first, there wasn’t much to feel. A lot of layers were between her sex and her hand. She rubbed harder, and felt desire flooding back in.
Kathryn sat down on a nearby chair to watch, her eyes gleaming.
Natalie kept rubbing, even harder now. A soft moan escaped her lips, and she had to brace herself with her other hand. The pullup was squishing rhythmically against her sec, wet and warming fast. She started panting, whined as her bladder felt ready to burst.
“If I come before I wet, I win.” She thought. Somehow it made sense, or at least gave her the motivation to keep holding it.
Kathryn watched hungrily, her hands wandering over her breasts. “That’s it baby.” She said. “Piss yourself.”
“No.” Natalie whined, but just the mention of it made her squirt a bit into her pullups. She moaned louder, the soft material was soaking now, and really warm. She bit down on her lip and rubbed for all she was worth, trying to hold it in with sheer pressure.
Kathryn panted, reached for her crotch and pawed at the belt, but it was no use. She went for her nipples instead, pinching them and moaning. “You can’t hold it.” She said.
“Yes I…” Natalie’s eyes went wide as the floodgates opened. A huge stream escaped her, far more than in the toy room. The warm wet flooded across her crotch, her rear, even up to the band of the pullups. She was swimming in it. Tears leaked from her eyes, she stopped rubbing herself for fear the plastic pants would leak.
“Good girl!” Kathryn cried. “Wow, you really filled that thing!”
Shame and discomfort mixed with her memories of waking up in a strange room wearing a soaked pullup. Natalie cried out as a tiny orgasm swept over her, then flopped on her back. She could feel tiny streams on her rear and thighs, the plastic pants had leaked, but just a little.
Kathryn let her lie there for a bit, then pulled Natalie insistently to her feet. “Okay hon, time to get you changed.”
Natalie turned a tear streaked face up to Kathryn. “Yes please.”
“But first let’s show our Master.” Kathryn smiled.
Natalie trembled. “No, no please! Just change me please Mistress.”
“I’m sure he wants proof that we followed his instructions.” Kathryn said. “No arguments. We’re going to see him now.”
Natalie hung her head. She could still feel tiny leaks making their way down her legs. She wasn’t sure how much worse it would get on a walk to the office but she was sure she’d be a mess.
The leash clipped onto her collar ring again, and Natalie felt it tug. She followed along, head down, her head swimming with humiliation as much as her crotch was swimming in wet.