Daring Kai - Part 35 (Patreon)

“I thought we only played when everyone was here!” Kai frowned as he looked at the dare bag nervously.

“Umm, we ARE all here!” Caleb scoffed, glancing at Kai, then to Leo, who was holding the bag, and Miles who was standing right beside him.

“Luca’s not here!” Kai said, with a slight twinge of sadness.

After their sleepover, which had involved Kai receiving an unrequested and guilt-riddled handjob from Caleb, Luca had headed off quite early. He had wanted to stay, but had, in his own words, “Some annoying family stuff I’m not allowed to avoid!” Kai had not objected but had been rather open in expressing his disappointment to see his new boyfriend leave.

“He’s a guest star at best,” Caleb shrugged.

“He’s part of the game!” Kai insisted angrily.

“Oh please, one dare and suddenly he’s ‘one of us’? I don’t think so!” Caleb argued.

Surprised to see the other pair squabbling, as it was usually more their thing, Miles and Leo glanced at each other before Leo said, “Shut up, both of ya!”

Miles rolled his eyes at Leo. He had hoped for something a little more constructive. Figuring it was up to him to step in, Miles stated, “We can’t hold everything up, just for your boyfriend. With your dating record, we’d never get anything done!”

“Dating record?” Kai said, recoiling a little as his brow furrowed. “He’s literally the first person I’ve dated!”

“Exactly, and you’ve been a couple for exactly one day. If your longest relationship EVER is only a single day, that makes for a pretty shit record!” Miles said matter-of-factly.

Kai went to object, his mouth opening briefly before it closed and he cocked his head curiously. He looked to Caleb, feeling a little sheepish for beginning to lose his temper, then shrugged as he said, “It’s annoying that he’s not actually wrong!”

“True,” Caleb nodded, looking equally embarrassed, “Although if you look at it the other way, you’re the only one of us who’s had a relationship that never ended!”

“Ha. Yeah, suck it, straight-boy!” Kai cackled, pointing accusingly at Miles. The comment took a moment to register before he looked at Caleb again and said, “You mean we’re the only TWO of us. Straight relationships do count, even if they ARE weird!”

“I’M BORED!” Leo huffed moodily as he waved the dare bag in front of Kai’s face.

“Hey, don’t do that,” Miles smirked, “That’s not the kind of sack he usually likes in his face!” The joke got immediate laughs from everyone, even Kai.

“Okay, you’re a twat, but that was funny,” Kai conceded. He sighed as he looked at the bag, then Caleb and said, “Fine, let’s pick a dare. Who’s next anyway?”

“Leo,” Miles immediately answered, then made a robotic movement as he saw Caleb snigger at him once again for his flawless memory.

Kai paused briefly, then considered his brother’s last dare. Leo had lied about it, deceiving the others into thinking he had been dared to give a blowjob, when the actual dare had only stated he had to get tickled. Neither Miles nor Caleb knew about the deception, and Leo had no idea Kai knew either. “Why don’t you draw it yourself then,” Kai said, his eyes narrowing slightly at his twin, “It’s fun seeing you read out something you REALLY don’t want to do!”

Leo hesitated for a moment as he pulled the bag back from his brother, looking a little guilty as he said, “Yeah, fine, okay.” He took a breath and reached into the bag before pulling out a dare. As he read it, his cheeks flushed. “I fuckin’ hate whoever wrote this!” he complained, rolling his eyes. “Don’t wear underwear on the next day we have PE!”

“Ohhh, fuckin’ love it!” Miles said happily.

“And you get two days to spend looking forward to it!” Caleb sniggered, as their PE classes took place on Tuesdays and Fridays.

“Seriously, who put this in there?” Leo demanded. He looked to Kai and asked, “Was it you?”

“No, but what’s the big fuckin’ deal? You made me shower. Just getting changed without underwear on… not exactly the toughest dare!” As soon as he said it, he regretted it.

“Then it’s time to make it tougher!” Leo said gleefully, happy to have the focus move on from himself. “Oh hey, should I message Luca and ask him his idea for making it worse?”

“No!” Caleb snapped, frowning heavily, “If he’s not here, he’s not part of it!”

The aggression of the reply didn’t go unmissed by any of the other three, but none of them questioned it, mostly as they had other things to think about.

Kai sighed as he thought about the dare, then said, “Well… okay… no underwear… and let’s say I have to wear the old PE kit again!”

“Mt Hargreaves is gonna love that!” Miles smirked, getting titters from Caleb and Leo. “Hmm,” he hummed thoughtfully for a moment before he grinned and said, “Butt plug goes in!” As he got gasps from the other three, he quickly added, “At the START of the PE lesson!”

“Damn, that’s…” Caleb started, but didn’t have a way to finish the sentence. “Well… umm… fuck, I don’t know. Isn’t that enough?”

“Someone’s going soft again,” Leo teased.

“No, I’m not!” Caleb snapped angrily, taking a step towards Leo before his eyes widened and he declared, “And neither’s Kai. He has to wear a rubber band round his junk, like a… a… what are they called?”

“Cock ring!” Leo exclaimed, then blushed and added a feeble, “Probably!”

“Might not do anything,” Kai shrugged, trying to sound unbothered by the horrific dare, “Those shorts are so small I couldn’t get hard last time even if I wanted to!” He blushed a similar shade to Leo and said urgently, “Not that I WANTED to!”

“Sure,” Miles smirked. “And you, boss man?” he asked as he looked to Leo.

Leo looked at his brother, picturing the scenario in his head. He squirmed slightly at the thought of it, but figured the worse he made things for Kai, the less likely people were to comment on him going commando. “Well, you’ll shower after PE. That’s pretty much a permanent thing now!” he ordered casually.

Kai sighed as he said, “I don’t know what’s worse, the fact he thinks he can just decide stuff like that for me now or the fact I know I’ll fucking do it anyway!”

“You’re so twisted. I love it!” Caleb chuckled, then cringed slightly at his casual use of the L word. He didn’t say anything to excuse or justify it but he did look away from everyone in obvious awkwardness.

“But for the actual dare,” Leo said, passing up the opportunity to tease Caleb as he knew he made for just as easy a target and didn’t want to face mockery in return, “You have to ask at least five other people… not including us… if they’re going to shower too!”

“Fuck!” Kai groaned. Once again, Kai knew that exposing himself, being hard and being naked were all things he would find embarrassing, but it was interacting with other people that truly made it awkward.

“Oh, I guess you can take the band off for showering. I mean… we don’t wanna be too obvious, right?” Caleb offered, shrugging at his attempt to sound reasonable.

“Thanks,” Kai said softly before looking to Miles to ask, “And the butt plug?”

“Fuck no, that’s staying in!” Miles sniggered, “You’ll just have to stay clenched to keep it hidden!”

Silence hung in the room for a few moments as they all dwelled on the dare that was to come on Tuesday. Finally, it was Kai that spoke up, already cursing himself for what he was about to say. “Well, that’s… not for a couple of days, so why don’t we take another dare to try and find something fun to do now!”

“Fun!?” Miles smirked, “Freak!”

“Yeah, and doesn’t Caleb LOVE that!” Leo smirked, unable to resist a slight tease.

“Shut up, Leo,” Caleb pouted, giving Kai a furtive glance.

“Sorry, I can’t hear you over the sound of me picking up the dare bag for your next dare!” Leo said as he picked it up, sniggering.

“Dick!” Caleb grunted as he stood still, making Leo come to him rather than making it any easier for him.

“Is that what you’re hoping to get out of the bag?” Leo sneered.

“Fuck you, Leo!” Caleb snapped, shoving Leo as he got closer.

Leo staggered back, laughing as he knew he’d got under the other boy’s skin. Eager to push further he added, “Oh, now THAT’S what you want the dare to say… or would you prefer it to say ‘fuck you KAI’. That’s more like it, right?”

“Woah woah woah, hold up!” Miles said as he jumped between them, along with Kai who was more than a little taken aback by the comment.

Resisting the urge to lash out with the others in his way, Caleb’s fists clenched as he snapped back, “Well maybe if it said ‘fuck you Miles’ you’d be begging to do it in my place, right!”

Miles and Kai both winced at the comment and turned, bracing themselves for potential violence. Much to their surprise, Leo didn’t look angry. He didn’t even look upset either, he just looked… pale! He turned and threw the dare bag angrily. It hit the wall and dropped onto Kai’s bed as he dashed out the room, slamming the door behind him.

“Ugh, is this where you tell me how shitty I am?” Caleb huffed as the other two looked at him.

“No, he totally started that,” Kai shrugged, then looked at Miles.

They all started slightly as they heard the sound of the front door slam too, presumably at Leo’s hands.

Miles shrugged too, then sighed deeply as he stated, “I wish you hadn’t said that to him, but… yeah, he started a fight he wasn’t prepared to lose!”

“Oh,” Caleb said, surprised to have the understanding of the other two. “I think… maybe I should go home!” he said sheepishly.

“You don’t have to,” Kai said, noting the avoidance of direct eye contact.

“Yeah, but I’m gonna,” Caleb sighed. As he headed for the door, he said a sorrowful, “Look, I’ll see you guys tomorrow. If he’s still pissed at me, just text me or something and I’ll head to school on my own, okay?”

“He’ll be fine, but thanks,” Miles said appreciatively.

Kai gave a meek smile and little wave to Caleb when he looked back before leaving.

“Well… this was fun,” Miles said with an eye roll.

Kai gave an awkward chuckle and asked, “Are you leaving too?”

Mile scoffed as he said, “Why would I? We ain’t done anything wrong!” As he got a gentle laugh in response, he smiled broadly and said, “Besides, how often do the two of us get to hang out alone?”

“Like… pretty often, actually!” Kai said with a raised eyebrow, “Usually when you want another…” He stopped as he rolled his eyes and shook his head, then finished, “When you want another blowjob!”

“I wasn’t even THINKING about that!” Miles said defensively, but as he saw the unconvinced look on Kai’s face, he took a deep breath and admitted, “Fine, I was thinking about it a bit!”

“You seem to be forgetting about my BOYFRIEND!” Kai said pointedly.

“Oh,” Miles pouted a little, “So that means you can’t do sex stuff anymore?”

Kai went to answer but paused as he thought about last night in bed, when Caleb had jerked him off secretly. He had felt guilty about it at the time, and then even more in the morning when he saw Luca. “I don’t know,” he said honestly as he sat down on his bed. “I mean… it’s not like we’ve been able to talk about this stuff yet. We got together and then basically right away we were just with you guys!”

“Fair,” Miles nodded as he dropped down onto the bed beside Kai. He smiled a little as he saw the dare bag lying behind Kai. Reaching for it, he waved it gently and said, “Luca seems like he’s really into the dares. I bet he’d be okay with you doing stuff if it was for a dare!”

Kai sighed gently. During the summer, he had gotten around his ‘no cumming’ rule once with Caleb by making it into a dare. Maybe he could do it again. “Yeah, but just saying ‘I dare you’ and then saying whatever it is you want me to do is kinda cheating!”

Miles frowned at the dare bag and cocked his head, looking thoughtful for a moment. “I’d say the chances of me pulling out ‘Suck Miles off’ from this bag are pretty slim,” he mused, getting a snigger from Kai, “So… maybe we play a game!”

“Why do I have a feeling you’re not talking Fortnite?” Kai asked with a wry smile.

Miles tossed the bag aside and pulled out his phone, then said, “How about this? I’ll roll my D6.” He glanced up at Kai briefly and smirked as he said, “That’s a regular dice to you plebs!”

“Brave talk for someone who’s about to have a very delicate piece of their body dangerously close to my teeth!” Kai replied coyly.

“Fair point,” Miles winced, “Please don’t bite me! Anyway, you’ll have to guess what number’s gonna come up, and then I roll! If you guess right, then… game over!”

Kai shuddered slightly as he sat up a little straighter and asked, “And… if I guess wrong?”

Miles looked Kai up and down. Knowing the odds, along with the growing understanding of his friend’s enjoyment for such things, he grinned and said, “You have to take something off!” He heard Kai gulp, so he continued, “And once you’re naked… I mean… IF you end up naked, then losing earns you a forfeit of my choice!”

“And whatever it is,” Kai started, unsubtly lowering his gaze to Miles’s crotch for a moment, “I have to do it?”

“That’s right!” Miles said, nodding eagerly, “SO I’m not even gonna ask if you’re in, cos we both fucking know you are, in which case… what’s your first guess?”

“Let’s go four!” Kai said, “That’s in the middle, better odds, right?”

“Wow, monogamy AND maths are both taking a hit today,” Miles muttered as he tapped the screen to roll the die. He watched for a moment as the virtual die rolled and came to a stop, then stated, “Five!”

“So close,” Kai said, already pulling off a sock. As he reached for the other one, he asked, “These count as one thing, right?” As he got a nod back from Miles, he tossed the socks aside and stated, “One! That’s my next guess!”

Miles tapped to roll again, then smiled as he said, “Nope, four!”

“Damn,” Kai said with a scowl. Though he enjoyed the forfeit for losing, quickly pulling off his t-shirt, he didn’t like being wrong so it was a strangely conflicting feeling. “Okay,” he said, casually stroking his flat stomach with one hand, “I’ll stick with one!”

“Bad luck, six,” Miles said after rolling again, watching happily as Kai’s sweatpants came off, one step closer to the inevitable dick sucking.

“Oh no,” Kai smirked as he rolled onto his back to pull his sweatpants out from beneath his butt before sliding them off completely.

Miles watched as Kai sat back up, then lowered his gaze to the other boy’s crotch, where his underwear was straining to hold back a fierce erection. “Oh, I’m sorry you’re having such a bad time,” he joked.

“Why you even looking, straightie?” Kai asked, grabbing at his cock through his underwear, “Like… are you even still straight?”

“Yes!” Miles replied firmly, but without any kind of anger, “I told you this already. I like girls!” He paused to grin for a moment as he added, “Actually I like WOMEN!”

“Gross,” Kai smirked.

Miles smiled at the comment, then shrugged and said, “But I’m only human… despite what Caleb says. I like cumming and I think it’s fun embarrassing you and making you do stuff. That doesn’t mean I’m into guys or into YOU.”

“Fair,” Kai nodded, then glanced at the phone in Miles’s hand and said, “I’ll go two this time. It’s got to be due to come out!”

Miles rolled his eyes a little as he tapped the screen, then held it up to show the four he had just rolled.

Kai repeated his previous move, rolling onto his back to pull his underwear free, then rolled back forwards, fully naked with his boner on show. “Oh no. It looks like I’m naked,” he said in a deliberately wimpy voice, “This is so embarrassing, being naked in front of you. I… don’t know if I dare to guess again!”

Miles held back his amusement at the charade and decided to mess with Kai a little as he said, “Oh, okay then. We’ll stop there!”

“But I’ve thought about it,” Kai suddenly blurted out, “And it turns out I DO dare, and… three!”

Miles finally lost the fight to hold back his laugh. Shaking his head, he tapped the screen and watched as the dice rolled. “Oh, look at that!” he said happily as he revealed Kai had guessed wrong again. “And for your forfeit, I think you’ll be sucking my dick!” he stated, sticking to his original goal.

“Okay, but… umm…” Kai said sheepishly, blushing a little as his cock throbbed, “Well… what if we… kept going?”

Miles frowned thoughtfully, eyes narrowing as he urged, “Okay, say more stuff…”

“Well we could just… keep rolling until I guess right and that’s when we stop,” Kai suggested, “And every wrong guess up til then you can, like… make it worse or make me do more or just… just… add something new entirely.” His hand reached down to paw at his raging erection, clearly revelling in the idea of more losses.

Miles grinned as he nodded and said, “Okay, but let’s make it quick. My dick ain’t gonna suck itself!”

Kai cocked his head as he saw Miles look strangely thoughtful. With a wry grin, he asked, “Are you imagining your dick being able to suck itself?”

“Yeah,” Miles nodded before looking mildly worried as he continued, “But my brain’s gone a really weird way about it and now I’m disturbed, so… guess!”

“Three!”

“Nope. Now you gotta suck my dick every day for the next week!”

“Five!”

“Nope. Now it’s every day til half-term!”

“Five again!”

“Nope, end of term now!”

“Fuck, six?”

“Bad luck. Let’s make it more than just sucking. Now any time it’s just the two of us, I get to be totally in charge!”

“Ugh, that shouldn’t make me wanna cum! Okay, two!”

“Same deal, but now til the end of year eleven!”

“Oh my god! Fuck. Okay, okay, come on, I can do this! I have to!”

Miles paused rather than tapping straight away. “Well why don’t we make this the last one then. One way or another! Guess it right and you’re JUST my slave for the rest of year eleven!” he suggested.

“Just!?” Kai sniggered, “Okay, and… if I’m wrong?” He was now openly masturbating over his mounting indebtedness to his friend.

“Then that’s it. No limits. Literally anything I want you to do, you do… forever!” Miles said, his own hand now pawing at his erection through his jeans. Realistically he knew he wouldn’t do much more than the occasional embarrassment and a daily blowjob, but he could see how excited the thought of it was making Kai. As much as he got his own enjoyment from the dares, it was nice to be able to give Kai something he so clearly enjoyed too.

“Fuck! Seriously. Just… slave to a straight guy for life,” Kai gulped. He frowned a little and said, “Okay, but… nothing that’ll get me dumped, killed or arrested!”

“Oh, well there go all my plans,” Miles said flippantly. “Yeah, of course. Just… fun stuff, with me in charge and you obeying. So… you gonna guess?”

“Yeah,” Kai nodded, “I guess… seven!”

“Kai, it’s a D6!” Miles chuckled.

Kai stared his friend dead in the eye, looking completely serious as he growled, “Seven!”

Miles tapped his phone and tossed it aside without even looking at the result. “Oh no, you lose. I feel so sorry for you! Now suck my fucking dick!” He stretched his legs out as he quickly began undoing his jeans, then giggled as Kai excitedly pulled them down with his underwear. “And you seem pretty keen to cum, so… start wanking and don’t stop til I cum in your mouth!”

“Gladly!” Kai said as he positioned himself to start sucking, pushing the bottom of Miles’s t-shirt up to reveal his pudgy stomach.

“Even if you cum, you keep wanking!” Miles added with a wicked grin as he linked his fingers and placed his hands behind his head.

“Fuck,” Kai grunted. He was ready to shoot already, so he had to hope he could get Miles off pretty quickly otherwise he was in for a very uncomfortable time. As he took his friend’s cock into his mouth, he put his summer’s-worth of experience to quick use stimulating Miles’s big dick in the ways he knew he liked best. The happy groans he could hear spurred him on, but also sent jolts of pleasure down to his own boner.

Glancing up without pulling the dick from his mouth, Kai saw Miles had his eyes closed. That was normal for him. He liked to let Kai suck his penis while he fantasised about it being someone else’s mouth. Kai sometimes thought he should be a little offended by it, but it actually turned him on to realise he was just being used as a tool for pleasure, rather than a sexual partner.

Kai felt his cock throb in his grasp and cursed silently for letting himself get distracted by erotic thoughts, as his hand had pumped away much faster than he needed to. He was about to cum and despite slowing his strokes, it was too little, too late. Groaning with his mouth still full, Kai pumped out a hefty load onto his bed as he continued pleasuring Miles.

By the time he stopped cumming, Miles had still not ejaculated, so he resumed stroking and felt the sharp discomfort of his post-orgasmic sensitivity. He gasped and whimpered his way through his own slow, torturous stroking, but the vibrations in his mouth from the noises he was making seemed to help spur Miles on towards his climax.

“Ah yeah, baby. Suck it!” Miles called out. “Swallow it! Every drop. Good girl!” he gasped dreamily as he shot into the imagined girl’s mouth.

Kai was quite happy being the fictional female as he gulped down Miles’s surprisingly hefty load. Satisfied that he had done as he had been told, he released his own cock, but continued sucking Miles in an attempt to get at least a modicum of revenge for the order.

“Ah fuck, Kai, stop!” Miles giggled as he pushed Kai away. Panting heavily as he laid exhausted on the bed, Miles grinned at the other boy and said, “I get to make you do that literally ANY time I want!”

“At least any time until you get a girlfriend!” Kai sniggered.

“Oh, maybe… maybe that’s what it should be!” Miles stated as he propped himself up on both elbows. “I know you were totally beating your meat over the ‘forever’ thing but… maybe we just say we do this until I get a girlfriend. I mean, I can’t see much chance of finding one who’d want me getting blown by my mate all the time, so it’d stop then anyway. So… yeah… you’re mine until I find a better option!”

Kai growled as he sat up and started trying to clean up the puddle he had made. “I wish that didn’t turn me on, but it totally does!” he said with a bemused headshake.

Just as Miles was laughing at the comment, the door flew open and Leo reappeared, looking like he was about to say something. He froze as he saw Kai naked, Miles half-naked and correctly assumed what was going on. “Fucking sluts. Fuck you both!” he scowled before slamming the door again.

“Fuck’s sake, what now?” Kai sighed at his brother getting upset again.

Miles sighed as he looked at Kai and asked, “Can I tell you something, just between us?”

“Technically I’m your slave, so I have to,” Kai giggled.

“True,” Miles said with a meek smile that quickly faded as he pulled his clothes back on, “But I’m serious!”

“Sure,” Kai said as he retrieved and pulled on his underwear.

Miles sighed as he looked round at the door, then back to Kai. “Leo’s in love with me!”