A Diapered Bet (Patreon)

“So that’s the bet–what do you say?” Ruby asked.

Jamie put his hand on his chin, considering the offer. “Just 24 hours? That’s all I’d have to do?”

Ruby laughed, holding out the folded plastic rectangle to her partner. “Do you really think you can keep your pants dry for that long?”

It was immature, but the comment had its intended effect. Jamie instantly became indignant, folding his arms. “You know I can do it, just let me use the bathroom first.” he scoffed, looking away from the punkish young woman. He turned back after a moment, blushing, “I’m pretty sure I can anyway; just because I like diapers doesn’t mean I need them.”

Ruby raised an eyebrow putting her hand on her hip. “I'm glad you’ll get the chance to prove how true that really is. Won't you, big boy?”

With his face turning fifty shades of red, the thin, nerdy sub stuck his hand out. “Fine, you’re on!” he blustered.

Ruby shook the offered appendage, sealing the agreement between them before sending Jamie skittering off to the bathroom with a slap on his bottom. “Go on,” she said with a chuckle, “get it all out so I can get you all diapered up.”

The moment the door closed with a click Ruby made a beeline for the kitchen. She’d never intended to let her diapered boy-toy win the bet between the two of them–that’s why she’d offered such a high price.

“As if I’d let that twerp pad and dress me up,” she scoffed, carefully opening a chocolate bar, “there’s no way.”

With the wrapper of the original treat intact, Ruby slipped a bar of almost identical chocolate into the cover. The difference between the two treats couldn’t be caught by the naked eye but she was sure Jamie would notice it about twenty minutes after devouring the sweet treat. "Silly boy never can turn down sugar," Ruby joked. "That and a few diuretic tablets in his apple juice will make sure that he soaks his padding."

With her assurances of Jamie's loss in place, Ruby slipped back into the living room just in time to hear the bathroom door in the hallway open. He strode into the living room with a new, seemingly unwarranted, confidence. “Alright,” he said, “I’m ready.”

Ruby gave him a shove backwards, causing Jamie to fall onto the couch dramatically. She paid his cry of protest no mind, confident that he was fine–this was their usual ritual after all. She hooked her thumbs into the waistband of his jeans, pulling down the trousers and boxers with one swift tug.

Just like always, he’d blush and hide his gaze, turning into a ball of embarrassment all while Ruby giggled and tickled and teased. Lotioning and powdering was his favorite part because it meant he got lots of special attention paid to all his delicate bits. Her favorite part was taping up the diaper and leaving him unsatisfied with the heated erection trapped against his body.

The way he’d moan and buck was always so fun, desperate for satisfaction, but the threat of a few swats to his bottom always quelled that. With the thick padding taped between his legs, Ruby helped Jamie to his feet. She didn’t bother giving him his pants back. It was so much cuter to watch him waddle about with his diapered bottom exposed.

The first hours of the bet weren’t too bad, with the pair going about their day doing housework or relaxing. Because their third roommate had moved out over a month ago, the pair indulged in their dominant/submissive back-and-forth openly within the apartment.

After a round of dishes and vacuuming, the diapered dork flopped onto the couch, sighing with mock exhaustion. Ruby put aside the controller, pausing in the middle of her game.

“Why do I have to do a bunch of chores while you sit around playing Resident Evil?” Jamie whined, flailing his hands at Ruby in a very bratty manner.

“It’s not my fault you always procrastinate and leave doing your half of the chores all for one day. I already did most of mine earlier this week. Did you get everything done?”

At this, Jamie nodded, sinking into the comfort of the couch.

“Good,” Ruby said with a smile, “Then why don’t I get you a treat?”

With an enthusiastic nod, Jamie agreed.

Ruby passed over the controller and stood, “Good, don’t let me die.” As she entered the kitchen she could hear the sounds of the game behind her and she was free to prepare Jamie’s favorite little snack. When she set it down in front of him he tossed the controller aside, snatching up a square of chocolate greedily.

Just as Ruby had expected he devoured the sweet treat before chugging down the apple juice with vigor. At no point did he recognize that the flavors of the candy were different than normal, nor did he sense a change in the sweetness of the juice. It was gone so fast that Ruby wondered if he had even tasted it at all.

With snacktime done, the pair returned to relaxing on the couch, passing the controller between them every so often and laughing. It was all fun and games, a normal relaxing Sunday… at least until the cramps hit. Ruby could see the expression change on Jamie’s face, his hands falling to his stomach, and he started looking around worriedly.

Ruby gave him a look of feigned ignorance. “Oh what’s wrong?” she asked.

Jamie shook his head, leaning forward. “N-Nothing,” he groaned. “I’m fine.”

She gave a wry smile and reached forward. “Awww does your tummy hurt?” she asked. With a probing hand, Ruby started rubbing his belly, applying targeted pressure to his bladder on each pass.

Jamie squirmed, trying to wriggle away from his partner’s touch. “N-No…” he said weakly. His focus was obviously more spent on keeping his pants dry instead of escaping Ruby. Either way it didn’t matter as seconds of inactivity left him vulnerable physically to her tricks and he let out a gasp while his pants swelled. A faint hissing could be heard inside the plastic shell, a steady stream of acrid failure permeating the inner absorbent core.

Ruby let out a gasp of her own, trying to sound surprised. “Wow! I knew you wouldn’t make it the whole twenty-four hours, but only three? You can’t even keep your pants dry for three hours?”

Jamie sat with his hand on the soaked padding, stuck in a state of shock while Ruby stood up, extending a hand out to him. “You know what this means don’t you?” she asked teasingly.

Jamie took her hand, the far-off look of defeat still in his eyes. “I have to do whatever you say…” he whispered, fearing the embarrassing task his partner would give him.

Ruby didn’t give a command, not immediately anyway. Instead she led Jamie by the hand down the apartment’s hallway, to the room that had previously been their roommate’s.

Jamie was confused, a feeling that continued until Ruby cracked open the door and revealed a fully decked out pink and white nursery with plenty of leather accents to promote the possibilities of kinkier activities.

“I-I… Ruby, what is this?” Jamie asked nervously.

Ruby laughed, patting Jamie’s soggy bottom to push him into the room. “This is your new room. I made sure to deck it out with all the things a wittle pants-piddler like you needs, plus you’ll be padded all the time from now on. We’ll throw all of your big boy undies in the fireplace later.”

Jamie’s jaw practically dropped to the floor, he couldn’t believe the outlandish nature of the proposal. “That’s crazy!” he cried, stamping his foot on the ground “The wager was that if I lost I’d have to do whatever you said not completely become a bab—”

Ruby interrupted him “You’re right, it was whatever I said, and I’m saying this is your new room. Not only that but I am saying you’ll be diapered 24/7. Get used to it kiddo, you lost.”

Jamie scoffed, crossing his arm over his chest. “Why would I do that? You can’t make me!”

Ruby chuckled, taking a seat in the rocking chair opposite the doorway. With her free hand she pulled out her phone, clicking the record button. “Haven’t you learned by now, puffbutt? All it takes is one little click and I can make your diapered butt internet famous on Twitter. I can hear your stomach grumbling from here. I’ll have the perfect video of you filling that padding here in just a second. Will you be good and listen to Mommy Ruby or do you want the internet to see everything?"

Jamie blushed, clutching his stomach. He knew she was right and could feel the roiling that signified he was reaching the end of his control. “I can’t believe you’re doing this again…” he said.

“Really?” Ruby asked, “It feels pretty in character for me. Does that mean you’ll listen to me?”

Jamie nodded.

“Good boy,” Ruby said, praising Jamie.

He blushed deeply, holding his hands in front of the tented front of his diaper in a weak attempt to hide his enjoyment of the situation. Ruby made sure to zoom in directly on that spot, putting her filmmaking degree to good use.

“W-Why’re you still filming?” Jamie asked, dropping into a squat.

“Oh this is just for me~” Ruby replied, slipping her hand down her own pants, “Don’t worry, I just want to capture the moment. Now be good and fill your pants for me, stinker.”

Jamie obliged by releasing his hold on his bowels, giving a little push to help it along.