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Cayden sat chilling on the couch in his apartment near the campus, not exactly waiting for his roommate to get home, but knowing he would be soon. And, just like clockwork, Milo stepped through the door. Milo was your standard gray wolf, a big ol fluffy boy that had secured his education with a swimming scholarship, and had a pretty muscular build as a result. Cayden himself was a lot smaller, a standard feline with pristine black fur. Cayden was a bit of a nerd, he loved video games and rarely did anything physical, so he came across as scrawny at times. There was an age old myth about cats and dogs not getting along, but he and Milo were pretty tight. They'd only met through college a little more than a year ago, but they were already the best of friends, mostly from their love of watching sports.

"Sup," Milo greeted, setting down his laptop bag and strolling inside towards the kitchen.

"Chillin'," Cayden answered casually.

"Ready for the game?" Milo asked as he rooted around in the kitchen for something, probably a snack.

"Ready for the Hawks to lose," Cayden taunted.

"Oh yeah? You feel like ah... putting a little wager on that?" Milo grinned as he entered the room, and as Cayden suspected, he had a plate of chips. Betting on the game wasn't out of the ordinary for the two of them, but it was usually something small like five or ten dollars. Just enough for a little fun, without affecting them much if they lost.

"What you got in mind?" Cayden inquired.

"Well..." Milo began, and out of the corner of his eye, Cayden could see him_grin._ Milo always grinned when something was afoot, that much Cayden had learned. "I got this funny prank idea from a friend..." Milo continued, setting down the chips but wandering off for something else. He came back with something square and pastel colored in his paws, and at first Cayden wasn't even sure what he was looking at. But as he studied the folded plastic, it slowly dawned on him what Milo was holding.

"A diaper? The fuck?" He questioned. He didn't even know they _made_them in that size. Well... he knew adult diapers existed, but not ones that looked like baby diapers like that. They usually tried to avoid that so as not to insult their customer base. "Where did you even _get_that?"

"Like I said, it was a prank idea from a friend. He let me swipe one so I could come up with something funny to do with it, and I did."

"Okay, but... why now?" Cayden hadn't actually thought of diapers since he'd been in the sixth grade, come to think of it. His father had caught him stealing a diaper from the daycare his sister had gone to, in the process of putting it on, no less, and gave him a thorough whipping for it. After that, he dared not try again, forcing himself to never think of it again.

"Why not?" Milo asked, "you scared?"

"Scared? Nah. Just wondering what the hell goes through your head sometimes."

"Alright then. Don't do it, if it's too weird. Don't freak out over a diaper or anything, hahaha." But the more Cayden thought of it, the more the idea intrigued him. His curiosity was piqued. Milo was offering an out, but part of him didn't want it to go away. He wanted to see where this went, for better or worse. He didn't necessarily want to_wear_ the diaper, that would be weird. But he didn't want it to go away and be forgotten. He was too interested now. A bet was a bet. The stakes were established.

"Nah... I ain't scared. You'll wear it if you lose?"

"Of course. A bet is a bet, right?" Milo grinned again. A wolfy, toothy grin. The kind that made Cayden squirm and wonder what was going on in that thick canine skull. "As is customary, I picked the stakes, you pick the win. Who you got?" Now this was Cayden's specialty. He was studying statistics, which is why he enjoyed sports.

"The Bears are on a hot streak, and their offense is top notch. The Hawks couldn't defend themselves out of a paper bag, and they're not doing too well. Give me the Bears any day."

"Alright then. Loser has to wear this diaper until tomorrow morning. Deal?"

"Deal." The two shook paws on it, and Cayden curled up on the couch again to watch the game when it had finally started. Milo brought in some more chips and soda, which Cayden partook liberally in during the course of the match. It was close, all the way up to the second half. 7-7, and each side looked equally matched, which was a bad sign for Cayden. He had expected the Hawks to get floored. However, his faith was restored when they made a touchdown in the third quarter.

"Yeeeeeeah!" he shouted, jumping up and cheering. "Get some!"

"Alright," Milo said, nodding, "I see you." Cayden took a victory chug of soda. The game dragged on with Cayden's team in the lead, giving him a nice ego boost all the way until the end. Up until he was a few minutes away from victory. He could _feel_it. He was standing up and cheering, excitement surging through him!

...all the way until the Hawks scored a miracle touchdown in the last few minutes of the game. It was tense, but at least it would go into overtime. The color drained away from Cayden's face as they scored a two point conversion, locking them in at one point higher unless the Bears could do anything to counter. As the clock dwindled, so did Cayden's hopes as the realization slowly set in; he'd have to wear a_..._

"I..."

"Just lost!" Milo taunted, grinning. "Guess who gets to get all nice and padded up?" He held the diaper up menacingly for Cayden to see. Shit, he couldn't do this. He had to find a way out. This was too humiliating, there's no way he could be expected to do this. And yet, they shook on it. It was sacred, unless he wanted Milo never to trust him again. And he didn't want _that._That would be a hundred times worse than any humiliating bet. Think Cayden, you're in college for a reason...

"Uhhh... double or nothing?" Cayden offered in a last ditch effort to wiggle out of the situation.

"Go on..." Milo continued, intrigued.

"How about... there's a Coyote's game on the other channel that's in the third quarter." Cayden picked up the remote, and switched it to the other game. It was 21-21, dead even.

"Oh that's easy, Coyotes win this hands down," Milo told him.

"So let's say, you pick the winner, loser has to wear the diaper for _two_days?" Cayden asked, hopefully.

"Mmm... no." Cayden's heart sunk. His plan, up in smoke.

"No...?"

"Nah. Not two days. How about... the winner gets to put the loser in the diaper, and you're not allowed to use the toilet at all until the bet is over." Okay, really weird bet parameters here, but Cayden didn't exactly have a choice at the moment. It was either that or the diaper.

"Fine," he said, "deal. So definitely Coyotes then?"

"Hell yeah," Milo replied. Cayden settled in anxiously on the couch. He was confident this time, but he was also confident last time, and look how that turned out. The Coyote's opponents did a really good job of shutting them out as the fourth quarter raged on, which pleased Cayden; until the opponents fumbled the ball and the Coyotes recovered.

"YES!" Milo cheered, "Just what we needed!"

"Speak for yourself..."

"Oh I am." And wouldn't you know it, not minutes after, the Coyotes kicked a field goal in the last few seconds that secured them the last-ditch win. "It's gooooooooooood!" Milo declared, jumping up and throwing his arms in the air, cheering. Cayden, on the other hand, was at rock bottom. FUCK. He'd lost both bets in one night. He couldn't even stand to think about it right now. But Milo would make sure that wasn't the case for long.

"So..." Milo asked with a smug expression, "about that bet..." Cayden had to face the music. A bet was a bet. It was the bro-code, and he had to honor it. He still thought it was extremely weird that Milo wanted to be the one to put it on him as he had stipulated in the double or nothing, but he was secretly glad it was that instead of two days.

"Fine," he conceded, exhaling in an annoyed fashion. "What do I have to do?"

"Well it's a diaper, and you can't exactly put that on over clothes, so strip em off." Okay, this was starting to sound really weird. But at this point, he didn't have a choice. With shaky paws he fumbled with his belt, finally freeing it from its lashing and loosening it enough to slip his pants down and step out of them. He considered keeping his undies on, but he knew Milo would just logic his way out of that too, so he may as well just go ahead and get it out of the way. Cayden turned pink as his private parts were revealed, sliding down his undies and throwing them on the pile as well, standing before Milo half naked.

"Good boy," Milo praised, and Cayden was about to protest, but hearing those words did some funny... things to his tummy. He felt... excitement? Happiness? He wasn't sure, but he felt a shiver of _something._But he couldn't let Milo know that. How dare he call him a boy, he was in college! He had to keep his reputation, so he frowned instead. "Now lay down," Milo continued. Cayden did as he was told (_not_like a good boy, but only because he had to), sighing and flopping down on the couch.

"Fine." Milo proceeded to grab the diaper and unfold it really slowly, almost purposely, in front of Cayden. Now that he had a better look at it, instead of a glance... holy crap. This thing looked A: incredibly thick, thicker than a normal medical diaper you'd buy at like CVS or Rite Aid, and B: incredibly infantile, almost like it was made for that purpose. It had soft pastel prints and a landing zone, and the more Cayden looked at it, the more he realized it was exactly like a baby diaper but in a larger size. Where the heck did Milo get_this?_ It seemed like the kind of thing that shouldn't exist. No one who had to use adult diapers for medical reasons would want them like that. And yet, he had to wear it. Him, a big manly cat, forced to wear a big diaper made for babies. This was the _worst._Milo stood over him, and laid the diaper under as far under his tail as it would allow without making Cayden get up.

"Alright, lift your bottom," Milo spoke gently in a soft voice, and as Cayden complied so that he could slide the diaper under his bottom, something... strange... started happening. His eyes focused on the soft padding, the pastel colors. He heard the loud crinkles. He saw Milo standing over him with a kind expression on his face, after having just called him a good boy moments earlier. He felt like he was a little kitten getting a diaper change... just the thought of that alone sent a shiver down his spine, and he felt tingling down below. The same kind of feeling he got when he wore girly panties and watched porn (not because he was gay or anything, mind you).

"Oh my," Milo noted with a playful smirk, noticing the same thing that Cayden had. His little stiffy was rock hard, pointing straight up in the air for all to see, not giving a fuck that his roommate was there to witness it. Cayden immediately covered his face with his paws, mortified. "Don't worry about it, these things happen," Milo assured him. It didn't actually make it better, but at least Milo was okay with it. "But I can't put the diaper on you with uh... that... being like that. And I'm not going to wait forever for it to go down only for it to come back immediately the next time. So just be a good boy and hold still." Hold still? What did that mean? Was he just going to move it around or some-

Cayden let out a little huff as he felt a jolt of pleasure rush through his body, and Cayden peeked through his fingers to see what the heck was going on. Milo had a small container of baby wipes, and was using one to massage Cayden's dick, causing him to squirm in pleasure.

"W-what are you..." he panted, not entirely sure what to do in this situation, but powerless to stop it. He was technically still a virgin, his only girlfriend in the ninth grade had broken up with him for not being "assertive enough" and they'd never actually fooled around, not even a hand job.

"I'm getting rid of this obstacle so I can continue the bet," Milo told him matter of factly as he continued working the shaft with his paws.

"But I'm not gay," Cayden blurted out. He still wasn't sure if he was gay or not, but he didn't know that he was. He'd never had any gay urges before, he'd never thought of Milo in that way.

"That's fine," Milo told him, "you don't have to be gay to get a handjob, just relax. We're just getting this little problem out of the way." It was no use fighting it, and it felt too good to resist anyway. Cayden accepted his fate, keeping his face hidden in his paws and not daring to look at anything else as the pressure in his penis continued to build and build until he could feel the crescendo coming.

After a little more enticing, the pleasurable sensations reached a climax, and he felt an orgasm rock his body as his groin started spasming uncontrollably, sending a short but intense euphoria to his brain before fading away, leaving him panting on the couch.

"That's a good kitten~" Milo praised, but Cayden no longer cared about any of that. In his post-orgasm state, he was filled with an intense shame, to the point where he could feel tears starting to form under his eyes. What the fuck was he doing here? Did he really just cum to the idea of being put in diapers? What the fuck was wrong with him? He wasn't even gay, how did he just let his roommate paw him off like that? Nothing made sense right now, but he was too emotional to say anything; he didn't want Milo to know he was on the verge of tears. After a minute, his erection had finally gone down enough to turn soft. First, Cayden smelled the sweet infantile scent of baby powder wafting about. Then, the diaper was pulled up between his legs and adjusted, and finally taped snugly around his waist.

"There you go," Milo announced as he stood up, "that wasn't so bad, was it?" Cayden was still struggling with the shame, but at least it was starting to fade as his body recovered from his orgasm. He nodded in agreement. "Now all you have to do is last till morning, and you're good. No more diapers ever again." Cayden nodded a second time. "I'm going to throw a pizza in the oven. Do you want anything?" Cayden shook his head this time. "Alright, be right back." Cayden was grateful for the break, using the opportunity to jump up and survey the situation. With his shirt, socks, and pastel printed plastic padding, he looked exactly like a toddler standing there in his diaper. It was amazing just how much that little piece of cloth had changed his entire perspective. He quickly sat down and curled up on the couch, trying to hide it as much as possible to lessen the embarrassment before Milo got back.

"Having fun, diaper boy?" Milo teased as he came back, and Cayden scowled.

"Very funny."

"It is pretty funny actually," Milo continued, with a smirk. Cayden didn't respond other than to continue scowling and cross his arms. The two continued to watch television in relative silence, until a stove timer made itself known. "Be right back," Milo told him, stepping out. Finally! Cayden had been feeling a pressure in his bladder from the earlier sodas, and as much "fun" as being in a diaper had been, he did NOT want to actually use it. That was TOO weird. Cayden slowly rose from the couch, peeking into the kitchen. Milo seemed distracted enough, so he tried to creep out. But if losing two bets had not taught him enough by now, luck was not on his side this day.

"Where do you think you're going?" Milo accused, carrying the pizza into the kitchen, spotting Cayden in the process. "You didn't go through all that trouble just to break the bet now, did you?" Oh shit. Think, Cayden.

"Uhh... I was... just going to get my blanket," he lied. "I'm cold." Milo shrugged, setting the pizza on the coffee table.

"Alright then." Cayden sulked as he walked into his room and fetched a white sheet, annoyed that his sneakiness hadn't paid off. Now he had to commit to the lie to save face. He wrapped it around himself and plopped back down on the couch next to Milo, who offered him a slice. It would be rude not to take one now, so he did. However, the pressure in his bladder was turning into pain. If he didn't go to the bathroom soon, it was only going to get worse. Looks like he was going to have to try actually using the diaper, much to his chagrin. This had to be the lowest low point in his life, but he was committed to getting through this (despite literally just trying to get out of it... but pay no attention to that).

He can't tell... there's no way he can tell... Cayden assured himself as he shifted in his seat, trying to find a comfortable position to ease the pressure while pretending to eat the pizza. Milo seemed not to notice; or at least, he didn't look over. Finally, Cayden found a spot where he could slowly release the muscle that held his bladder shut, and as a trickle of pee escaped, he clamped it again in panic. It was weird, trying to go in his pants, without a toilet. He ran a paw over his diaper; everything seemed okay. And his bladder was starting to hurt. He eased it up a little... the small stream felt heavenly as his body praised him for emptying itself, and the pain went away as the stream continued, so he allowed it to flood. He huffed softly as he felt the entire front of his diaper grow warm to the touch and expand, becoming noticeably larger and more swollen. He had just... wet his pants, just like a toddler... in a diaper,_no less... something he hadn't done since he was an _actual kitten, potty trained before he could even remember doing it.

His fur instantly stood on end as he flushed pink, realizing what he'd just done. Milo still seemed interested in the television, chowing down on his pizza, thank god. But he couldn't stop his paw from groping and massaging the front of his diaper under the covers of the sheet, pressing the swollen padding into his crotch, going over and over in his head what he'd just done; wet my DIAPER... like a KITTEN... a little kitten... diaper... and before he knew it, he was instantly hard again, massaging his erection through the diaper. This was officially the most fucked night of his life so far. Why was he getting hard thinking about that?! He'd never thought of diapers like that before, why now?? And now he had a real problem. He wanted to paw off so bad, but Milo was literally right there, and he didn't think he could move enough with Milo watching for him not to notice. He did NOT want to ask Milo again, that was too humiliating. So he had to simply... wait.

Cayden watched the seconds go by agonizingly slow as Milo put his feet up on the recliner with some popcorn. He would have gone to his room and taken care of his little problem a long time ago, but he did NOT want to get up and risk Milo seeing him in a wet diaper. It was bad enough that he had to endure being put in one. And yet, the more he looked at Milo, the more he imagined himself curled up in his lap in a diaper and-... nope, not going to go there. He refused to go there. That was weird. This was a BET, nothing more. So he waited, all the way until Milo finally, finally rose from his chair later in the night.

"Welp," Milo said, stretching, "I'm going to bed. I have class in the morning. Don't stay up too late~" he teased, gathering up the empty popcorn bowl and pizza tray and taking them into the kitchen to dispose of, before heading to his room on the opposite side of Cayden's. "Tomorrow morning. Remember," he said, looking right at Cayden.

"I know," Cayden replied, sticking out his tongue. Milo just smirked and closed his door. Cayden waited for a few minutes, making sure Milo didn't pop out again just to tease him. After he was satisfied there were no shenanigans going on, he hopped up from the couch and made a dash to his room, blushing at how much the swollen diaper made him waddle like a preschooler with a load in his pants. He shut the door behind him, exhaling in relief. Safe at last... so that he could take care of the other pressure building up.

But first, while he was still semi soft, his bladder was full again from all of the drinks, and he knew the sound of water in a toilet or just flushing was sure to alert his roommate. Besides, he'd already done it once, what was the use of holding back now? This time Cayden had the benefit of holding onto the bed while he stood bow-legged, making it quite easy to flood his diaper for a second time that night, the warmth trickling down his crotch as it was distributed throughout the soft padding. He put a paw down to feel it again, and was surprised to find that the bottom and butt area was still mostly dry, only the front was swollen. Holy crap, these diapers held a LOT. But he'd only need it for the rest of the night, he would never find out just how much they held anyway. And in the morning, he could use a proper bathroom, so this was probably his last wetting. GOOD.

But he still had the other issue to deal with... the fact that running paw over the soft, crinkly, swollen plastic while thinking about what he had just done and what he was wearing had caused him to get hard yet again. The fuck was wrong with his brain... but at least Milo would never know. No one had to know. He would do this one last time, and in the morning, never think about it again. At least, that's what Cayden told himself as he settled down in bed, using both of his paws now to gently knead his diaper, purring softly in pleasure.

He switched back to one paw as the other found its way into his muzzle, sucking his thumb like a little toddler. He imagined himself back on the couch, Milo hovering over him... calling him a good boy as he got his diaper changed... Cayden's purring got even louder as his paw worked the soggy plastic, the thick swollen padding felt like heaven against his needy bits, crinkling intensely to the rhythm of his paws as the pleasure built up, pushing him closer to the edge. As he neared the precipice, he thought of even more horny and ridiculous ideas to spur him on that he probably wouldn't have otherwise; Milo replacing his cups with baby bottles. Getting rid of his bed while he was away and replacing it with a crib. Imagining himself in a crib right now, in a daycare instead of college...

He came within seconds of imagining his infantile fantasy, arching his back and moaning softly as he filled the inside of his already-soaked diaper with his hot seed.

Unfortunately, just as before while on the couch, Cayden was then filled with an intense shame. What the fuck. What the actual fuck. These were some fucked up fantasies. He was in COLLEGE. He shouldn't be enjoying baby anything. This was so stupid. He didn't care if it was a bet, it was over. Done. No need to humiliate himself further. He ripped the tapes off the sides and tore the thing from his waist, flinging it towards the trash can in his room. It bounced off the side and landed with a plop on the floor, but he didn't care. He'd deal with it---and confront Milo about this whole stupid thing---tomorrow.