Diaper Training - Ch2, Reconciliation
#2 of Diaper Training
The saga continues. NSFW warnings apply.
Cayden struggles to reconcile his feelings for his roommate... and his diapers.
Ch1: https://www.sofurry.com/view/1804896
Cayden awoke the next day to the morning sun streaming through his window. He had nothing to do that day, so he didn't mind sleeping in for a while... until the events of last night came rushing back and hit him full force. His fur immediately puffed up in an indignant fashion as he remembered the diaper, and all of the things that went with it. And in it. Including---no, especially---his horny fun with it before he'd ripped it off and tossed it in the trash in shame. And Milo... his cheeks turned pink and he felt a tingling rush in his chest that he couldn't quite place. Goddamn Milo. It was probably just the weird association with diapers, that's all. Speaking of diapers...
Cayden looked over at the trash can and realized something slightly embarrassing. He'd actually missed the shot last night, and the used diaper lay folded open on the floor. Ah shit. Good thing his door was closed, that would have been awkward. He slithered out of bed and picked it up, intending to toss it in the pail properly. It had some heft from when he'd wet it multiple times, and it was soft and squishy to the touch. He felt a jolt of excitement and curiosity run through his fur. He wasn't sure why he was having these urges, they were definitely not normal. But as long as no one was around... No one to judge him but himself...
He poked his head out of his door and looked around. Milo had class today, and wouldn't be back till much later. No one had to know the antics of a curious kitten. He glanced around shyly one more time before shoving his nose in the soggy padding. It still had its sweet, powdery aroma, mixed with the fresh scent of pee. It crinkled under his muzzle as he handled it, and he thought to himself as he nuzzled it, this is MY diaper... I did this...
He felt himself getting hard, and really had to question his sanity. To anyone else, this would be super gross, and yet... there he was, shoving his nose in it and getting turned on. And then he had another, more naughty thought; it was still relatively fresh, right? It wasn't stale, and it was the only one he had, it's not like he could just get another. Maybe one more time wouldn't hurt...
Feeling very much like a naughty kitten sneaking a cookie late at night, Cayden took the old diaper back to his bed and curled up under the covers as if someone might come in at any moment. His pulse was quickening by the second as he thought about what he was doing. This is so wrong... He thought to himself as he placed the soggy padding on his pelvis. He sucked in a short breath of air, it was cold to the touch. He still had no undies or pants from last night's shenanigans, so it was a simple matter of arranging the diaper correctly on his hips, and then pulling the tapes snugly around his waist. He was pretty sure he wasn't doing this near as well as Milo, it looked crooked as heck and the tapes were losing their stickiness. But the idea was there. The sodden diaper pressed nicely against his hard bits, and he pushed his paws into it, kneading it up and down to stroke himself along the shaft using the diaper's wet bulk.
"Haaaaah..." he moaned as his paws worked the plastic. It felt heavenly. Thinking of Milo fixing his diaper tapes led right back to thinking about Milo putting him in diapers, which only turned him on more. He imagined Milo smiling down at him, sliding the diaper under his bottom. _"Good kitten..."_the dream-Milo cooed, and Cayden stuck his thumb in his muzzle, eliciting a soft purr.
"Kiwten," he repeated with a lisp, rubbing harder and faster with one paw while nursing the other, the cacophony of crinkles only reinforcing the infantile feelings floating in his head that he desperately tried to cling to. His mind was only focused on getting off in his diaper, any other feelings were completely eclipsed at the moment as pure need overtook him. It only took precious few minutes to reach his climax, filling his diaper with a fresh round of kitty spunk, and he collapsed in a panting puddle under the covers. With no more horny to fuel his conscience, reality came flooding back in. And reality was harsh sometimes.
"Fuck..." he lamented, still breathing heavily. The familiar feelings of shame and self doubt came rushing back as well, although they were getting slightly easier to deal with each time. But they were still there. "The fuck is wrong with me..." he repeated to himself, slowly sliding out of bed and wiggling out of the freshly marked garment. He walked over to his small trash can, holding the thing above it. "I'm in college._College! I'm not some diaper wearing freak, I'm _normal." And to make sure his future self wouldn't be ravaged by horny temptation again, he dug his claws into the thing, spilling the saturated gel into the trash can, leaving the plastic front in ribbons. "That settles that," he told himself, tying up the bag. He quickly donned his clothes for the day and took the small but heavy trash bag out to the apartment dumpster, unceremoniously dumping it inside. He replaced the trash bag in his room when he got back; fresh, clean, no diaper, like it never happened. He let out a sigh of relief. Finally, he could move on with his life.
If only things were that easy.
It all started---or, he should say, continued---when Milo got home. He meant to act big, tough, like nothing really had happened, but as soon as he saw Milo enter the apartment, set down his bag, and give that customary wolfy smile, he felt that flutter in his chest, it choked any words he'd wanted to say.
Sup is what he would have said, all cool and casually, if his mouth would cooperate.
"Sup 'kay," Milo said first, preempting his own greeting and using his shortened nickname.
"H-hey," Cayden replied nervously, giving a little wave. What the heck was wrong with him this time? No diapers or bet to distract him, clean slate, and he still acted this scared? Get it together, Cayden! Man up!
"How was your day off?" Milo asked, flopping on the couch opposite Cayden.
"Pretty good. Just relaxed a lot..."
"I hear that. My day off tomorrow," he declared, pulling the side handle to put his feet up. He looked so... snuggleable. And that thought made him cringe. Why? Why would he think that? Call of the void. This was definitely call of the void. He went through a bad experience once, and now his brain was punishing him. Thankfully, mercifully, Milo seemed to have forgotten the previous day even existed. No mention of it, or the bet. Work tomorrow would take his mind off of it.
But it didn't. Periodically while stocking shelves, he'd find himself zoning out, thinking about what it was like to wear diapers. If the diapers in the cub section would fit him... (he was pretty small, after all). If they had any diapers like the one Milo had in the incontinence section... he just couldn't help himself. After reprimanding himself the first dozen times, he gave up trying to stop entirely and let his mind wander. Could he... he felt a tiny electrical tingle run down his spine, and his stomach flip flop just forming the thought. Could he actually ask Milo to... see about getting another diaper and... well, of course he'd have to do that thing again if Cayden was too "stiff to continue..." even if it was embarrassing, he'd never had a sexual experience with another person before, and it felt so-
"Hey. You alright?" His coworker Sam, a cute panther girl asked, causing Cayden to leap five feet in the air and drop the product he was holding.
"Y-yeah, sorry, you just startled me. What's up?"
"You've been spacing out all day. One of the managers was worried."
"Oh, yeah, just a lot on my mind is all."
"Do you need to talk about it?" No. Nope. Nuh uh. Not one bit. Cayden hadn't even wanted _himself_to know, let alone another soul. Not in a million years.
"Nah, it's fine. Just some personal stuff."
"Alright. You know I'm here if you want to talk."
"Thanks," he replied sheepishly, picking up the box he'd dropped. "I'll be alright. Just some things I have to figure out."
As expected, Milo was at home relaxing when Cayden finished work. He shed his shoes on the way in, and it was his turn to flop on the couch.
"Rough day?" Milo asked.
"Just a lot to think about," he admitted before he, surprise, thought about it. Unlike Sam, Milo would actually know what Cayden was thinking about, and that would tip him off that something was up. "Work stuff," he added quickly.
"Aight well, I'm gonna get ready," he said, rising from the armchair he was seated in. Oh, right. This was the day he went to his friends house for drinks, games, and hanging out. When they first met, he was too shy to ask because he didn't know Milo all that well and he didn't want to impose. He was curious over the course of the year, but he hadn't been brave enough to ask. Until...
"Can I come with you this time?" He blurted out. He never cared before, he enjoyed the solitude, actually. But tonight, knowing Milo was going to leave, being all alone... he felt unnaturally scared of being alone.
"Really?" Milo asked, pausing as Cayden posed his question. "You've never asked to go before."
"Yeah, well... I don't know... I just thought I'd ask, you know? It sounds fun." Milo appeared to think about it for a moment before rendering his verdict.
"Tell you what. I'll ask them tonight what they think about bringing you along, and if they agree, I'll take you next week, deal?" Cayden felt the crushing sting of rejection, even though he understood the reason. He was an outsider, inviting himself along... it was a wonder Milo had agreed at all.
"Alright," he said, swallowing a small lump.
"I don't mind if you meet my friends, I just have to give them the heads up first," he reiterated.
"Right on. I understand." Milo wandered off to gather his things, and Milo sighed. One night alone... but thankfully, the only night of the week.
Cayden hunted around the apartment like a cat on a mission, rooting around through every container he could find. He had made the mistake of working himself up on the couch after Milo had left, and he no longer cared if liking diapers was "weird." His body wanted it for some reason, and that meant he really wanted it. He was in a horny-fueled mood, the kind where you'd do anything to get off, look anywhere, use anything. He felt extremely naughty as he poked around Milo's laptop bag, and not the sexy kind of naughty, either. He felt like he were a kitten in his parent's house again, sneaking into places he shouldn't, raiding the fridge at night, staying up all hours of the night, risking being grounded. However, no matter where he checked, the house was totally devoid of anything diaper related.
He stood on the precipice of Milo's room, gazing into the dark interior. If there were diapers in the apartment, they'd be in here... he knew it. Milo wouldn't be home for hours. As long as he left everything how it had been...
But in the end, he couldn't do it. It was too naughty. He would get in trouble if Milo ever found out. He pouted and returned to his own room, flopping on the bed, momentarily defeated. Well, if he couldn't paw with ONE set of naughty underwear... he pulled a box out from under his bed, full of girly clothes. Not that he was gay, mind you. He just loved the way it made him feel, cute and pretty. He would never tell anyone about this for as long as he lived, much like the diapers, except for the fact that Milo had caught him once or twice. That had been awkward. Thankfully, Milo was a bro and never mentioned it. Much like the diapers, come to think of it. He was cool in that regard.
It wasn't like Cayden couldn't paw. He most definitely could. However, it just didn't feel the same after his last few orgasms had been in diapers. He never realized just how much that would affect him, the thickness, the squish, the crinkling, the little feelings... it was all too perfect, all too wonderful and blissful and... nice. He never thought he'd say such things about a diaper, but here he was.
And what would he have done if Milo was here? Well... he had been thinking about asking Milo if he had one of those spare diapers lying around, hence searching for it when he was gone. However, he'd forgotten about his late night hang out, so that plan had been ruined. He let out a resigned sigh as he was forced to paw with what he had on hand, so to speak. It wasn't as exciting, but it would get the job done. Tomorrow.... he would attempt to work up the courage to ask Milo if he had a spare diaper. But for now, he slept.
Cayden sat through statistics class, every bit as spaced out and dreamy as he had been at work. He didn't think he even heard half of what his teacher was saying, which would be a problem for future-Cayden, but not present-Cayden. But his daydream would be interrupted by a pencil eraser pinging off the side of his head, snapping him back to reality.
"Earth to Cayden," a corgi girl named Sarah told him, with a smirk.
"What do you want," he whispered back in an annoyed fashion. He had known Sarah since high school times, but lately she had taken it upon herself to be extra irritating, teasing him, making fun of him, making herself a nuisance.
"For you not to miss half the lesson, dipshit," she taunted.
"Okay, second question, why do you_care?_"
"Fine, don't pass the class, no skin off my nose as they say. Don't have to be such a baby about it~" Cayden's ears perked and he pursed his lips, nonplussed. It's a generic insult, he had to tell himself. There's no way she could know. ... could she? Was he giving off some weird vibes lately? There was that thing with Sam yesterday... was he really that readable?? "Jeez Cayden, are you alright? You look like you've seen a ghost!"
"I'm fine, alright?" he replied, "I just got some stuff going on, and you're really distracting from this lesson you know." God. He couldn't wait to just end this existence at class and run home. But home was going to be a nervous wreck, considering what he was going to do. Why couldn't he just teleport forward in time to when everything solved itself? That would make it so easy...
But thankfully, time did move forward, and before long, Cayden was throwing his own bag by the door like Milo had done the other day, sprawling out on the couch and turning on the TV. His anxiety was already starting to spike as he both anticipated and dreaded what was to come. Last night, he had come to some realizations. He could not just let this go. Every time he tried to run from it, he failed. It only came back stronger, and he felt shame from his denial. So he was going to do it. He was going to ask Milo if he had a spare diaper. And of course, he had no idea how to put one on... so he'd have to ask to be diapered again, logically. And, logically, if something were to get in the way, it would have to be tended to...
Cayden shuddered as he felt like his chest were compressed and he were lightheaded. That thought certainly had some sort of effect on him, but it was needlessly working him up; he was already nervous enough without dwelling on it. But it was hard not to!
After about an hour of languishing in mental turmoil, Cayden heard the door opening. This was it... the moment of reckoning. His heart was pounding out of its chest. Why was he so nervous? It was just a diaper, a stupid piece of plastic. But it was also his pride, his reputation, his dignity vs his wants. All of this was doing through his head as Milo strolled through the entrance and made his way to the kitchen.
"What up," Milo greeted on the way there, and Cayden heard the sounds of rooting through cabinets and the fridge.
"Oh you know, hanging out after class," he answered, trying to sound casual as he fell apart internally.
"Anything fun happen?"
"In a stats class? As if..." And Milo laughed at that as he walked in with a single glass of soda, sinking into the couch seat on the end.
"Anything good on?" Milo continued, and Cayden threw him the remote so he could browse through himself. As the two sat in silence, Cayden was so nervous he was practically shaking. Just do it... just ask... he told himself, but he couldn't make himself act. It was like a mental block. Unfortunately, or perhaps thankfully, Milo also seemed to eventually notice what was going on. "Hey, you okay? You look like someone's going to jump through the window at any minute and assassinate you or something." Cayden realized he had been really tense, sitting in an upright position while squeezing his hands in anxiety instead of relaxing as he usually did.
This was his moment. He'd been addressed, it was time to make his move. Just do it. Just do it!
"I'm fine..." he started out, his pulse loud in his ears. "But..." here it comes. He was doing it! "I wanted to ask a... question..."
"Yeah?" Milo inquired. Cayden's reply would come slow, like he was struggling with each word. (Because he was).
"Do you... have... uh..." he could bail right now if he wanted. Change for a twenty? An extra soda? An opinion on the next Hawks game? ...but no, that was the coward's way out. He'd come this far. "...another one of those... ...things?" He couldn't make himself say diaper. That was just TOO embarrassing right now. At least he said it, hopefully Milo would catch on.
"What things?" Milo asked casually, not even hinting whether he might be fucking with Cayden or not. He was going to make him say it out loud, wasn't he? You know, usually it was felines that were the masters of subtlety and wordplay and facetiousness. That's just how they were as a culture. But Milo sure was giving him a run for his money.
"Uuuugh," he lamented, and Milo cracked a grin. HA! Milo had revealed his tell. He did know!! "You know what it is!"
"I know," Milo said, not hiding his smirk anymore, "But I want to hear you say it." Okay, he was definitely having too much fun with this.
"You're into this!" Cayden accused indignantly. So was Cayden, technically... maybe? He was still new to this. But Milo had to be!
"Yeah, no shit," Milo confirmed matter-of-factly. "When did you figure that out?" Cayden just sat there for a moment, completely frazzled. He hadn't expected Milo to just declare it like that so easily! "So are you going to say it or not?" Milo added. This was it. Cayden had been defeated. He huffed in frustration.
"Do you have a... diaper..." he forced himself to say, and if it was possible, Milo grinned even_more._
"Yeah, I think I got another one around here. Let me go see." Milo rose from his spot on the couch, and Cayden felt like he were going to die of embarrassment, despite Milo treating it like it were nothing. He returned in short order, carrying one of the diapers from the other night, pristine and unfolded. "Here you go," he said, tossing it to Cayden before sitting back down on the couch where he'd been. Cayden clumsily caught it, fumbling with trembling paws.
"Th-thanks," he stammered, laying it in his lap, practically dying.
"No prob. Just let me know if you want any more." The two sat in silence (minus the TV that was still in the background) for a minute or two, with Cayden burning a hole in the floor because he couldn't bear to look at anything else. Well, now what did he do? If he was too chicken to actually ask Milo to put it on him, was this all for naught? And Milo said he was into it! So it shouldn't be a problem... right? Come on Cayden, do something!
"Ummm..." He started nervously, and Milo looked over.
"Mmm?"
"I have... no idea how to do this..." he confessed. "Y-you had to put it on me... remember?"
"Does the little kitten not know how to put on a diaper? Do you need big ol Milo's help?" He teased, and Cayden went crimson. He wasn't sure he was ready for this much blood rushing to his head, he might even pass out. There also seemed to be blood rushing to another part as well... what the heck? Was he really being turned on by this? Being talked down to like a toddler? Oh god. He just kept digging himself deeper into the proverbial hole.
"Y-yes," he squeaked, still trying to turn the floor into ashes with his stare.
"Alright well, you know what to do~" Milo replied in a playful voice. Cayden certainly did NOT know what to do! But, if last time was any indication, it was probably to lie on the couch and wait for Milo to do it for him. He forced himself to turn in his seat and scoot his bottom down, settling into a lying position on his back with the armrest supporting his head, his feet nearly touching Milo, holding the diaper to his chest.
"Like this...?" He asked timidly, and Milo rose from his seat, standing over him, which made his heart drop through the floor. Milo looked so... big? ...parental?... from this angle, and Cayden felt the same electric feeling from earlier zap through his fur and cause his heart to flutter. Milo was going to see him naked... again. And this time, he'd asked for it. No "bet" to fall back on and blame this time.
"Yes, exactly like that. Good kitten. Now are you going to take off your pants, or do I have to do that too?" Cayden felt his ears turn pink upon being called a "good kitten," and his pulse raced as he realized he'd have to show the hard-on he currently had from all of the teasing and the daydreaming from earlier. Except now... the daydream was actually going to happen. This is what he had wanted, right? All according to plan. He was actually surprised it had gone down this easy, there were so many things that could have gone wrong.
"I can do it," he offered quickly, fumbling with his belt. He pulled his pants and his boxers down with one fell swoop, kicking them off to reveal the present beneath, naked for all the world to see.
"Mhmmm, I see," Milo noted, looking down at him like a doctor assessing a patient. "No wonder you wanted me to diaper you." Cayden couldn't even argue. This _was_why he wanted Milo to diaper him, there was no mistaking it. Cayden covered his face with his paws and just let it happen... just like last time. However, unlike last time, he felt a curious rubbery object touch his lips and he opened a crack in his paws just enough to see Milo poking a pacifier at his muzzle. In no position to protest, and completely unable to even if he wanted, he took the soft teat into his maw and started nursing it intently. To his own utter surprise, he immediately felt his anxiety start to decrease as the soother went to work, so aptly named.
"Good boy," Milo praised him in a gentle voice, "now lift your butt." And Cayden did exactly that. He felt the diaper slid under his bottom, and then a paw on his hip indicating he should sit back down, and he laid on it. "Now, we diaper the baby." Those phrases were going to be the death of him if he kept blushing this hard, he was going to die of lack of oxygen, he just knew it. He chewed on his new pacifier to ease his flustered mind. His nose picked up the distinct sweetness of baby powder, and he felt the light fluttering on his groin, followed by an unexpected force that used his ankles to lift his butt in the air just enough as the powder was applied there, too. He forgot how strong Milo could be, being fit from swimming and all. This was it. There was only one thing left to do: take care of his erection before Milo... before he... wait.
"W-wha?" Cayden eeped around the soother as Milo brought the diaper up between his legs, adjusting the front across his tummy, pressing his dick flat against his body with its soft padding, completely covering it. "Buh..."
"Mmm?" Milo questioned, as Cayden heard the distinct sound of diaper tapes being pulled away from their sticky backing. Milo stretched the wing and pulled the plastic taut, pressing the tape to the front landing zone, completing one out of the two tapes.
"I fought you had to... you know... take cawe of the thing fiwst, so the diaper would fit..." Cayden lisped around the pacifier, shocked by just how babyish it made him sound.
"Oh that? Yeah, I lied. I just wanted to see you squirm, and it worked, didn't it?" Milo huffed indignantly as the second tab tape was pulled and stretched across the front.
"No faiw!" He whined as Milo taped him snugly into the big baby diaper, giving it a soft pat, right on the erection.
"Is that so?" Milo asked, with a knowing smile.
"Hmph!"
"Is the little kitten going to pout until he gets his way?" Goddamnit, Milo. Stop doing this to him! He was literally too good at teasing! It seemed he was going to have to do this the hard way... by asking.
"C-can you...?" He managed to eek out. He was nervous, and embarrassed, but he was also horny, and as any person would know, once you were horny, you would do _anything_to alleviate the situation. Milo had given him his first sexual experience, and it had been the best orgasm of his life, and he desperately wanted to feel it again.
"Mmm... no." Milo answered, and Cayden felt like he were just doused in ice water. His whole world, his plan, shattered. He suddenly felt extremely self-conscious laying there in front of Milo like that, and he contemplated running away.
"N-no?" He squeaked, hoping for some kind of reason.
"No. Not yet." Okay, so there was hope.
"Not y-yet?"
"The first one was free, because you're really cute, and I wanted to see you squirm. But now kitten has to do something for me if kitten wants a reward, that's how it works. Plus, you owe me."
"Owe...?" he asked softly. What could he possibly owe to Milo?
"Oh yes. I know you took off your diaper the night of the bet. I opened your door to check on you before I left for class to see if you'd keep it on, and you didn't. So now, you owe me for breaking your part of the bet." Cayden's heart sank; Milo knew. He knew he fucked up, and now it was coming to bite him in the ass.
"I'm sowwy," he whimpered, "I used it to paw and I fewt bad so I frew it away. But I put it back on in the morning, I sweaw!" Why was he admitting that? That was gross!
"Oh really?" Milo asked, genuinely intrigued. "Well, that's a step in the right direction. But I still want my favor."
"W-what's the favor?" He inquired timidly.
"Sit up." Cayden did as he was told, shifting to sit up on the couch, the diaper rustling loudly with every movement. Milo went over to his armchair and gestured for Cayden to follow. "Come." Again, Cayden obeyed, walking over. Milo was being so firm and dominant... he couldn't resist. "Kneel down." As Cayden knelt before Milo, he started to get a feeling on where this might be going, and his heart started to throb. Was he really about to do this? He never thought he was gay... but he never thought he'd be into diapers, either. Could he do this? He was still a virgin, after all... what if he screwed this up royally?
His suspicions were confirmed when Milo slowly unzipped his pants to reveal his tented briefs underneath, the fabric clinging to his form as it revealed the bulging outline clearly. He pulled the underwear down, causing his rather large cock to flop out, standing at attention, pointing right at Cayden's face.
"I won't make you do anything you're uncomfortable with," Milo started out, "so if you can't do it, don't worry about it. It'll be okay. I won't be upset. However... if the little kitten wants his 'treat...' and wants to make Milo forget about how much of a naughty kitten he was with the bet... well, babies know what to do with bottles, don't they?" Cayden's head was spinning. The way Milo was talking to him was driving him crazy, and he couldn't even fight it. He didn't want to fight it. He was enthralled. Milo was drawing him in with his charm, and he was powerless to resist. He'd never so much as touched another person sexually, so this was entirely new territory.
Cayden leaned in, the tip of Milo's dick almost touching his nose. His pulse was ringing in his ears from how nervous he was, but he fought it back enough to continue. He_wanted_ this. His own throbbing member demanded it, not the least bit put off by the thing in his face; nay, it was even more of a turn_-on,_ being told to go down on his roommate, ordered around by someone else who was in charge. He was just a kitten, after all. He had no idea what he was doing, but he'd watched enough porn that he knew how to do it... in theory. But_actually_ doing it... he had to beat down his anxiety, push aside his hesitation, and just... commit. He still didn't know if this made him gay, and he was almost scared to find out. But there was only one way.
He forced himself closer, the smell of Milo's crotch deep in his nostrils now. Of course, there was only one thing stopping him now; Cayden removed the pacifier from his muzzle and set it aside, making room for another type of teat. He couldn't believe he was doing this. Years of dreaming of sex, and this_was going to be his first experience. Instead of having sex with a girl, he _was the girl. That thought alone sent a tingle of happiness through his body. There was a reason he had a collection of girl clothes deep in his closet he kept hidden.
He brushed the underside of Milo's cock with his tongue, testing the rubbery texture, getting his first taste of another boy. It was a point he never thought he'd be at in a million years, but so far, he had no regrets. As he ran his tongue along the length, he heard Milo give out a soft huff of approval, and he knew he was doing something right, at least. The final step was to... open his mouth and...
Cayden slowly took Milo into his muzzle, exploring the sensation of his roommate's dick pressing into the back of his throat; being his first time, he wasn't accustomed to the feel, and he nearly gagged. But then he felt Milo's reassuring paw press gently on his head, giving a soft ruffle right between the ears. He wasn't shoving Cayden back down, merely letting him know he was there with his presence, and he approved.
"Gooooood kitten..." Milo cooed softly, and that's all Cayden needed to hear. Milo's praise egged him on, his own little stiffy aching in his diaper, begging for attention. His head was fuzzy and he was in full horny mode, desperate to do anything for release, even if it meant having his roommate shove his cock in his muzzle before he was "taken care of." In fact, at this point, he might as well just do it himself. That's what people in porn did, right? Fondled themselves while giving a blowjob? He put one paw on Milo's member like he'd seen in the videos, right behind his knot, and his other paw went to his diaper, pressing it and rubbing it against his throbbing bits, sending a shock of pleasure through him. Yes, just a little-
"Ah ah!" Milo reprimanded firmly, grasping Cayden's hair and pushing him away far enough to make him stop. He looked up in panic, wondering if he'd done something wrong; oh god, did he brush against it with his teeth? A hundred thoughts flooded through at once, and he nearly cried.
"Good kittens don't touch their diapers," Milo instructed him gently, looking him right in the eyes. "Only naughty kittens play in their diapers without permission. You want to be a good kitten, right?" Cayden nodded eagerly. "Then you let Milo decide when you're allowed to touch yourself. And I want you for myself, so you're going to have to wait." He released Cayden's hair, and Cayden was so relieved he immediately went back down on Milo with renewed vigor, desperately wanting to please him so he could get to his reward. Milo was in his head, his instructions, commands, and firm but gentle hand were winding him up like a tight spring, and all he could think about was release.
"Theeeere you go, that's a goooood boy..." Milo cooed as Cayden started to notice an odd, salty sensation on his tongue; from curiosity in the past, he knew what it must be, and Milo was getting close. As he sensed the other boy so close to release, he bobbed his head and worked the underside with his tongue as he'd seen others do in the videos. Now that he wasn't allowed to touch his diaper, he could use both paws to help with Milo's member, one behind the knot to give the sensation of being tied (or so he'd read in the smut stories), the other right in front of his own muzzle along the shaft to give the sensation of being deeper than he was. All of the times he'd imagined himself being the girl in porn, and he was finally living his dream, in a roundabout way. His efforts were rewarded as his ears picked up the sounds of Milo panting softly, felt the weight of Milo's paw still held on his head, tasted the ever increasing amount of pre in his throat.
Without warning, he felt Milo's cock buck in his muzzle, and Milo's paw pressed on his head so he couldn't pull away. In that instant, a thick, hot load of fluid filled the back of his throat, and thanks to the paw on his head, he had to desperately swallow as much as possible to avoid choking and gagging. He was successful for the most part, as some leaked out of the side of his muzzle and dribbled down his fur. After an intense few seconds that seemed to stretch for an eternity, Milo finally sighed and sank into his chair, removing his paw from Cayden's head.
"Holy shit, you're so good at that," Milo praised as Cayden pulled back, wiping his muzzle with his paw, his face freshly abloom with a flustered blush. He'd just given his first blowjob, and swallowed it all. Milo's cum was in his tummy right now, the evidence all over his chin. And he liked_it. That was the shocking part. He wasn't traumatized, or felt like he were blackmailed or forced. He was horny, turned on, wound up, and he _enjoyed pleasuring his friend.
"Did you enjoy your treat?" Despite his flustered state, he nodded. "Good. _Now_it's time for your reward. C'mere, cutie," he beckoned, giving his lap a pat. Cayden stood up shyly, assessing the best way he should do this. Face to face? Back to front? In his indecision, Milo chose for him, taking him by the hips and guiding him into his lap back to front. Milo fetched Cayden's pacifier and returned it to his muzzle, which he gladly accepted. Milo had an easy, natural access to Cayden's diaper now, reaching around his waist and pressing his paw into the front, causing that familiar shock wave of pleasure to shoot through his body as his own needs were finally tended to.
"Mmf!" Cayden squeaked in ecstasy as Milo rubbed, massaged, and pressed the soft padding into Cayden, working up a slow and steady rhythm against the shaft. Cayden bit down on the pacifier in pure unadulterated need, clenching Milo's pants in his fists as he squirmed and huffed and moaned behind his soother.
"You like your diapers, don't you?" Milo teased as he pawed Cayden's diaper his lap, and Cayden nodded eagerly. "Tell me. Say it."
"I wike my diapews," he cooed behind his pacifier, utterly lost in need. "I wike... I..." the poor cat couldn't even last that long as he positively exploded in his diaper, wave after wave of pleasure washing over him, soaking the front of his diaper with his little kitten squirts. Those precious, euphoric moments were mind blowing.
"That's a good kitten..." Milo cooed tenderly as Cayden came down from his high, panting. "That felt really good, didn't it?" But Cayden couldn't answer. Not right away. Unfortunately, his post-orgasm shame hadn't gone anywhere, but with Milo's comforting embrace, and his own coming to terms with himself, he could at least mitigate it this time instead of running away or getting angry with himself.
Cayden covered his face with his paws again---a gesture that was becoming all too common, he felt---and leaned into his friend. Without the haze of heat hanging over his head, he could finally take stock of what he'd done. He'd given his friend a blowjob... in a diaper. His first sexual experience. And he'd even swallowed. He couldn't claim it was forced, he did it willingly and eagerly. He wasn't ashamed of it, he knew he enjoyed it at the time. So why was he so emotional? Why did he feel like he was about to cry?
"It's okay," Milo cooed, stroking his hair softly, and Cayden immediately felt his anxiety subside, just like earlier with the pacifier. Milo seemed to be attuned to what Cayden was feeling. "You're alright, kitten. It's alright. There's no need to be ashamed. Okay?" Cayden nodded, feeling safer already with the tender ministrations. "Good boy." If Milo had not been there to reassure him, he most certainly would have run into his room and locked the door, probably stripping the diaper off in the process. But he didn't want to do that, it was his stupid brain rebelling. He wanted to be here, with Milo, enjoying his presence. And so he would. The two sat in silence for another minute or two, until Milo felt it were appropriate to speak again.
"Cayden... you don't have to if you don't want to, but I have a little request of my own, if you'll humor me." Cayden peeked up at Milo between a crack in his paws, indicating he should continue. "Could we... stay like this, just for a while?" Stay here... in Milo's lap? It seemed too good to be true. There's nowhere else he'd rather be at the moment, and what else was he going to do? Hide in his room? He didn't want to do that. He gave a shy nod. "Thank you, Cayden."
Milo reached to the side of his armchair and pulled the lever, causing the entire thing to tilt back. He shifted Cayden in his lap so his feet were to the side instead of in front, lending itself to be cradled naturally against the larger boy, his head on his chest, listening to the heartbeat and soft breathing within. With his arm cradling Cayden, his paw ended up at just the right angle to rub his diaper softly, giving it a pat every now and then, causing it to rustle and crinkle and remind him exactly of what he was wearing. Between that, the pacifier, being cradled in someone's arms, and the afterglow, Cayden was feeling incredibly small an infantile in this moment, safe in Milo's loving arms. Without realizing it, he started purring softly, contentedly, happily. And the thing was... he didn't regret it. It felt nice. It felt right. It felt like a piece of himself that had been missing all of these years, that he had been repressing, and now it was coming out full force---and Milo had been there to help him explore those feelings. He sighed happily and closed his eyes, soaking in the tender pets, snuggling into his friend.
Cayden must have been more tired than he'd realized, because he didn't even notice he'd fallen asleep until he was awoken by jostling and shaking. In his sleep-addled state, he clung to Milo to avoid falling, who seemed to be carrying him in his arms with ease. Cayden was in no position to question it, so he just snuggled into Milo's chest and went along with it, although the walk wasn't long and, much to Cayden's fussing, he was laid in his own bed and tucked in. His last memory of that night was the sensation of a soft kiss right between his ears, before drifting off for a second time.
Cayden groggily rubbed his eyes in the darkness of his room, his feline vision adjusting swiftly to find his phone, checking it for the time. It was four in the morning, which seemed about right, given that he'd fallen asleep SUPER early in Milo's arms when he...
Cayden's paw shot up to his muzzle. His pacifier was still in, surprisingly. He put a paw to his groin; thick diaper, no pants. The memories came rushing back. He blushed softly, realizing he had to pee, badly. At this point, it wasn't a question of should he wet his diaper, it was just a matter of doing it. He wanted to, he was put in diapers for a reason. His blush increased further as he knelt on his bed, letting go. He felt the warm flood bloom throughout the front of his diaper, the thick infantile garment more than adequate for the job, soaking up the entire thing. With his bladder needs satisfied, he laid back down on the bed, still a bit groggy. There was no need to get up for a few hours, so he may as well catch up on some more sleep.
As he pulled up the covers and nursed on his pacifier, his paw explored his wet diaper, groping it and feeling the new warm, squishy bulk. He was pleased, and slightly turned on. But the "fun" from earlier had worn him out, and he wasn't in the mood to paw... yet. He snuggled under the covers, closing his eyes for sleep. As his mind wandered in the still silence, he found his thoughts drifting to the idea of what it would be like if Milo had taken him to his bed instead, and he instantly started to purr happily at the thought. He also realized, with a flutter of his heart and a tingle through his fur, what exactly all of those feelings he'd had earlier were. The same ones he just experienced now as he thought about it. The same ones he felt as he snuggled up to Milo's chest. The same ones he felt when he thought about Milo at all, really. Snuggling him, the diaper changes, the uh, "treats..." it was finally time to admit it to himself.
He was crushing on his roommate. Hard.