Daring Kai - Part 39 (Patreon)

“This is assault, and it is unacceptable and I’m going to be writing a very strongly worded email to your mother!”

As threats went, it wasn’t the best, but it was all Luca had managed so far as he found himself at the mercy of Leo and Caleb. He was currently pinned to the ground with Leo kneeling gently on his back.

“Yeah, that’ll stop ‘em,” Miles said sarcastically, suffering right alongside Luca beneath Caleb.

The game of truth or dare had fizzled out a little after Leo and Caleb’s arousal from their prolonged near-nude cuddling had been revealed. It wasn’t that any of them really chose to stop playing. Luca and Miles had started mocking the two bigger teens about it and their teasing had been met first with angry/embarrassed glares, which shortly after escalated into playful teasing back and finally into the playful violence that had taken over.

Kai had happily stayed out of it. Pulling a pair of shorts on, he had stretched out on his bed, happily watching the other four mess around. Every time peace seemed to be returning, Luca or Miles would throw out another insult and it started all over again. Spectating was fun. Not just because Caleb and Leo were still both dressed in their underwear which was clearly exciting Luca, but also because it was just nice to see everyone getting along. No Leo drama. No Caleb drama. Luca comfortable as part of the group. It was just… nice!

As much as he was just enjoying the sight, he couldn’t stop his mind from wandering. It had been a week since Miles dropped the bombshell on him that he knew (or suspected!?) that Leo was in love with him. Leo being into a guy would have been the bigger shock, had the news come a few months earlier, but it was something Kai had been growing to suspect over the past few weeks.

Being in love with Miles, that was the part he had struggled with! At first it had actually started to make sense, explaining some of Leo’s behaviour, but now he could see Leo interacting with Luca he was starting to doubt it once again! The way Leo acted with the newest member of their group was so similar to how he was with Miles. Leo and Kai were brothers, which meant their relationship would always be different from the others. Leo and Caleb were frenemies, which meant they had their own set of rules too. Miles was neither of those things, and nor was Luca. Perhaps this was just the way Leo acted with people who weren’t his brother or frenemy. Kai really couldn’t figure it out, but right then he really didn’t feel the need to, he was simply enjoying the moment.

As the night grew late and thoughts of bed drew in, Miles had stated quite bluntly, “Guessing you want us three to fuck off so you two can be all gay together, right?”

“Yes!” Kai replied at the same time Luca said, “No!” They looked at each other a little awkwardly.

“Oh, I… umm…” Luca mumbled uncomfortably.

“Excuse us,” Kai said politely to the other three as he took Luca’s hand and led him away slightly. “Hey,” he said softly as he saw Luca looking a little nervous, “If you’re not ready for a night of… just us, it’s fine!”

“No, I’m ready!” Luca insisted, then grinned as he leaned forward to press his crotch against Kai’s and growled, “I’m VERY ready, I just…” He paused to look round at Leo, Caleb and Miles who were very busily trying to look like they weren’t eavesdropping. Smirking a little at their obviousness, he looked back to Kai and said quietly, “Last week, all of us sleeping in here together, it was one of my favourite nights ever and… umm…”

“It’s okay, I understand,” Kai said, reaching up to stroke Luca’s cheek gently, “Then how about I suggest we all stay in here, but… this time… you stay in my bed with me?”

Luca’s eyes widened as he nodded excitedly.

“You’re so cute,” Kai said dreamily as he slipped his arms around Luca and pulled him into a kiss.

Luca happily kissed Kai back, ignoring the teasing they immediately heard from across the room. When he finally pulled away, he smiled and said, “How about we just do that all night instead of sleeping?”

“I like the way you think,” Kai said happily, giving him a final peck on the lips before moving to threaten the others for their teasing.

Despite even more chatting-related delays, wrestling-related shenanigans and kissing-related teasing than usual, the boys eventually settled down for the night in Kai’s room. Leo and Miles had taken the spare bed as usual, though this time Miles and Kai had exchanged amused looks when Leo had claimed it so vehemently. Kai had declared that he and Luca would be sharing his bed, and that he would hear no teasing about it – he immediately heard a lot of teasing about it! That had relegated Caleb to the pull-out mattress on the floor which he didn’t seem happy with, but he also didn’t outright object.

Kai had been unsure what position he would lie in with Luca, but as they got comfortable he found himself on his back with one arm resting around his boyfriend, who was happily curled up against him. With Luca’s head resting on his shoulder, they hadn’t been lying together long when he felt Luca’s hand on his stomach. It didn’t seem to be there with any particular intent, it just happened to be where it had come to rest. Eventually it began to move a little as Luca started mindlessly tracing shapes across the smooth, taut skin with the tip of his finger.

For several minutes, Kai remained happily motionless as Luca cuddled against him and continued his teasing touches. His dick was rock hard, purely from having another boy in such close contact, but particularly from the roaming finger. He knew it wasn’t intended to turn him on, but it was doing it anyway and he was almost enjoying the frustration of it. He wondered if he was alone in his arousal until he heard Luca whisper, “I’m so horny right now!”

“Fuck, me too,” Kai gasped back softly.

“Should we… go somewhere?” Luca asked, lifting his head a little to glimpse at the vague dark outline of the room’s three other occupants.

“Maybe,” Kai whispered back, thinking for a moment before he smiled to himself and asked, “How would you feel about… doing stuff WITH the other guys?”

Luca didn’t speak. Instead, he answered by shifting a little, pressing the raging hardness of his cock against Kai’s hip.

Kai sniggered slightly, then reached out to click his lamp on.

“Woah! Too bright!” “A little warning next time!” “Is it morning?” the other three groaned out in response to the sudden illumination.

“Is anyone else finding it… HARD… to get to sleep?” Kai asked with barely even a pretence of subtlety. The awkward silence he got back answered as clearly as the erection he had just felt pressed against him. “Look, if you guys wanna… y’know… umm… knock one out, we won’t tease or anything!” he offered.

More silence followed.

“Orrrrr…” Kai said, pausing to build the tension as the room remained silent, “Unless you all want another speech from Luca about eunuchs… I do have… ONE more dare in mind!”

Caleb stared over at Kai from across the room, then looked back at Miles and Leo.

“What… kind of dare?” Miles asked, seemingly speaking for all three.

“A simple one,” Kai grinned, “Two words… circle… jerk!”

If the room had been silent before, it had now crossed the line into something even quieter than silence!

“I’m not scared!” Leo said bluntly, shrugging in a poor attempt to look casual.

Kai stared back at his twin, wondering how much of this actually was his bravado and how much was just him taking the opportunity to see Miles jerking off! His eyes fell on Caleb, knowing that Leo’s willingness would almost certainly force him to follow, if only to avoid being out-done by him. He felt his cock throb at the thought of watching him. He wasn’t displeased with the thought of seeing Miles doing it, and the thought of watching his brother wasn’t exactly terrible either, but Caleb masturbating… Kai WANTED to see that. “Well?” he asked curiously.

Caleb was staring back, looking equal parts terrified and excited, especially as he nodded and added a quiet, “Whatever!”

“Great, come on then,” Kai said as he threw back the covers and swung his legs out of the bed, making no attempt to hide the bulge in his underwear.

“Don’t I get any say in this?” Miles protested as he sat up.

“Well WE’RE all doing it. D’ya really expect me to believe you’re just gonna roll over and go to sleep?” Kai asked with a wry grin.

Miles rolled his eyes and said, “Fuck, Leo and Caleb being nice to each other, Kai being right about something… we’re officially in bizarro world tonight!”

“Me am Bizarro!” Luca said with a smile as he climbed out of bed to follow Kai.

“Ugh, he’s a keeper!” Miles sniggered at Kai.

All five boys headed back for roughly the same positions they had been sat in for the short-lived game of truth or dare. As Kai pulled his underwear off and stood shamelessly nude, he grinned at Caleb and asked, “Want Leo on your lap again?”

“No!” Caleb and Leo both replied in unison, the following laugh from the others breaking a bit of the obvious tension as they gathered.

“So, umm… do you guys… do this often?” Luca asked, slipping a hand inside his own underwear to grasp at his dick, not stripping quite as eagerly as Kai.

“Never!” Miles said, shaking his head emphatically.

“Well there WAS the popcorn thing!” Kai said with a nod, smirking as Leo and Caleb seemed to have silently decided between them that they would both get their dicks out at the same moment so neither had to go first.

“Popcorn…” Luca started, frowning, “Wait… do I want to know?”

“We had to shoot into a bowl of popcorn and then Kai ate it!” Miles explained, enjoying the flushing of Kai’s cheeks at such a blunt way of putting it.

“Wow, what cinema do you guys go to?” Luca asked with an impish grin.

Kai let out a gentle whimper. As the others looked at him, he chuckled a little awkwardly and said, “Sorry, just… imagining a cinema like that!”

“Jesus, one week outta the closet and you’re already the world’s biggest slut!” Miles said with a headshake.

“Woah!” Caleb and Leo both recoiled at once.

“Oh, no, wait, sorry,” Miles said, looking mortified, “I know that sounds like a massive insult but it’s not, I promise. I think it’s really cool that you can just… say stuff like that and be okay with it. I swear I didn’t mean slut like a bad thing!”

“Chill guys,” Kai smiled. “And thanks,” he added, glancing to his brother and then Caleb, “Sweet of you to defend my honour!” As they both blushed a little, Kai turned his attention to the last person in the circle, Luca, and added, “It’s more than my own boyfriend did!”

Luca shrugged and said, “What? I agree! You’re a slut!” It got a few laughs, that turned into groans as Luca leaned over to Kai and added, “But you’re MY slut!” before giving him a kiss. “Ah, shut up,” he said dismissively to the teasing noises coming from the others.

“So Miles,” Kai said, casually tugging away at his dick, “What ‘stuff like that’ do you feel you CAN’T say?”

The short, chubby, ginger boy was already red-faced from the fact he had pulled out his penis and started masturbating in front of his friends, but his cheeks managed to darken more at the question. “Nothing,” Miles insisted, “I just meant… well… I was just saying… umm… oh my god, shut up Kai!”

“Aww, look how red he is!” Luca joked. His eyes narrowed slightly as he looked round to his boyfriend and said, “Come on Kai, why don’t you start us off. Tell us something you’ve never had the nerve to say before!”

“Oooooh!” Leo, Caleb and Miles chorused playfully, enjoying the slight distraction from their masturbation.

“Thanks for that,” Kai growled, getting a cheesy grin back from Luca. “I dunno,” he said, blushing a little as he tried really hard to avoid looking at Caleb. Suddenly, something came to him and he said, “Yeah, I know something!”

Miles gasped with playful dramaticism and demanded, “Dish it!”

“Well… these… these dares, I mean… when we started playing,” Kai said a little awkwardly, slowing his hand as he could already feel himself getting close to cumming, “Well I… may have only been so keen because I thought… well… that there might have been a chance to… see you guys naked!” He glanced around the group, from Miles who had his t-shirt pulled up to his chest and his dick out, to Leo who was shirtless with his underwear tucked beneath his balls and to Caleb who was basically naked, with his boxers around his knees as he knelt in the circle. “Which I guess kinda worked,” he added with a shy smile.

“Oh my god, I’m so shocked!” Miles said flatly.

“Yeah, never woulda guessed,” Caleb agreed, smirking at Miles.

“Am I really the only one who never knew about Kai?” Leo asked, sounding playful but with a slight twinge of sadness behind his smile.

“I didn’t,” Luca chimed in, “But I wasn’t here, so I don’t know if that counts!”

The whole group laughed for a few moments, but it slowly died down to leave just the sound of slow wanking. All five of the boys seemed to be matching pace, though for some it was from a reluctance to cum first and for others it was to prolong the enjoyable experience.

“Fine, not THAT big a reveal, but still… I admitted it,” Kai shrugged, casually stroking his chest with his free hand. “Anyone else got anything they’d… like to confess?” It took all of his willpower not to stare at his brother and he couldn’t help wondering if Miles was having the same struggle.

“I’ve…” Caleb started, then stopped, looking mildly annoyed at even starting to speak. Before any of the others had to prompt him, he rolled his eyes and continued, “I’ve got something, that’s… I dunno, I don’t even know why I’m… ugh, forget it!”

“No, please,” Kai quickly jumped in, “You never share stuff so… it’d be good if you do!”

“I share things,” Caleb said sheepishly without making eye contact.

“Mate, your nan died and you never even said a word. You don’t fuckin’ share!” Leo said abruptly. Seeing the slightly annoyed looks from Miles and Kai at his bluntness, he quickly added, “But… you can. And if you’re gonna say you enjoyed our little cuddle, chill, so did I. I’m man enough to admit it, but also man enough to kick the arse of anyone who’s got a problem with it!”

Caleb burst into laughter as he nodded and said, “Fair deal, mate. It’s not that, but good to know!” The smile dropped a little, but only from embarrassment as he psyched himself to make his confession. Taking a deep breath as the other wanking boys looked on intently, he explained, “Well… you know that time I came back and the three of you were, like… napping together!”

“Oooh, details!” Luca interrupted.

“I wanted sleep. Grabbing those two into bed with me was the only way to make sure they didn’t keep plotting,” Kai explained bluntly.

“Fair,” Luca nodded, then looked at a slightly annoyed Caleb and said, “Sorry, carry on!”

Caleb scowled a little but went on, “Well, the picture I took of the three of ya together… I… really like it!” Caleb’s cheeks had turned such a dark crimson it was surprising he hadn’t passed out from lack of blood supply to his brain.

“Aww, that’s not so bad,” Kai said, smiling fondly.

Caleb pursed his lips, unsure why he was saying more, but he went on anyway and added, “And sometimes… when I feel… sad,” He paused to sigh a little. “I look at it and… imagine kinda… being in the middle of it!”

“Mate!” Leo said, shaking his head.

“I know, it’s lame,” Caleb said awkwardly.

“Mate, no,” Leo said, then dropped his hand away from his dick and shuffled on his knees toward Caleb to hug him.

“You don’t think it’s lame?” Caleb asked softly.

Leo sniggered as he held him, then pulled back and said, “Totally lame, but kinda cool too!”

“Okay, I think I’m really getting on board with THIS Leo,” Miles said, cocking his head thoughtfully as he looked at his best friend.

“Is this… not the usual Leo?” Luca asked curiously.

Leo went to speak, but nothing came out.

Seeing his brother in obvious distress, Kai quickly jumped in with, “Hey, maybe this WASN’T the best time to get into a big discussion. Kinda… doing other things!” He released his dick and waggled it, letting it slap side-to-side against his naked body to accentuate the point.

Luca let out a sudden gasp. As the others looked at him, his eyes flashed wickedly as he looked slyly at Kai and said, “Kai should be our popcorn!”

Miles frowned and asked, “Is he having a stroke?” His eyes briefly darted down to the long, slender cock in Luca’s hand and added, playfully, “And I don’t mean THAT kind of stroke!”

Luca snorted with laughter and said, “Clever, I like it! But no. You said you all… ‘did it’ into a bowl of popcorn, right? Well… Kai should lay down and we should… y’know…” He gestured to indicate ejaculation, aiming vaguely at the spot in the middle of the group.

“Ewwwww, that’s disgusting!” Miles recoiled, then looked at Kai and said, “Do it!”

Even though they weren’t alone, Kai still felt compelled to obey Miles. Truthfully, it just seemed like a fun idea, but he put on at least a slight show of unhappiness about it as he got down onto the floor. Lying with his head between Miles and Luca, with his legs between Caleb and Leo, he said casually, “And lemme guess. I don’t get to cum til after all of you?”

“Oh. Oh oh oh oh!” Luca called out excitedly. Without waiting to be prompted, he blurted out, “We should make it a race! First to cum has to make Kai cum!”

“Oh yeah, please, let me win that race!” Miles said sarcastically. He saw Leo sniggering at the comment, but Caleb didn’t react aside from staring intently at the naked boy lying before him.

“Oh my god, another idea…” Luca said, almost bouncing with joy.

“Oh my god, can someone shut him up?!” Miles smirked.

“LAST one to cum has to lick Kai clean!” Luca declared.

Everyone froze, motionless aside from eyes darting around the group. Their hands remained clasped on their dicks, nobody daring to move quite yet, like some kind of masturbatory Mexican stand-off! Then, suddenly… they were off! There was a sudden rush of wanking as the boys accepted the terms of the challenge without saying as much.

“Wait, fuck, no,” Miles said, slowing his hand, “I wanna be not last but I also wanna be not first!”

“Who else REALLY wants to see Miles come last?” Kai asked as he stared excitedly round at the masturbating boys around him. Grinning even more broadly, he added, “And hey, I guess I mean that literally!”

“Is it wrong that someone actually using the word ‘literally’ correctly is almost enough to make me cum?” Miles joked.

“I know right,” Luca giggled, “Now shut up. I got a race to win!” He pumped away rapidly at his slender cock. He had been expecting to face no challenge for first place, but Leo and Caleb were both masturbating furiously too. “Ah damn,” Luca gasped as he watched the other boys wanking, “This’d usually be the moment I wake up lying in a wet patch!”

“I probably shouldn’t find that as hot as I do,” Kai said, gulping slightly as he reached out to stroke Luca’s thigh. Excited as he was about the game and the imminent forfeits, he REALLY wanted to touch himself. Instead, he was forced to lie and watch one of the most exciting things he had ever been part of, without so much as touching himself.

“Ah, damn, damn, I’m getting close,” Luca gasped gently.

A few moments before Luca began to shoot, Caleb had shuffled forward and sent his first spurt of spunk flying onto Kai’s chest without a word. The second hit Kai’s stomach at the same time as Luca’s first.

“Fuck, that wasn’t meant to happen,” Caleb said, blushing heavily as he finished squirting his spunk onto his naked friend.

“Bugger,” Luca complained, flicking the last drips of jizz from his dick before quickly pulling his underwear back on.

“Fuck, gotta go faster!” Miles suddenly declared, now realising the race was just for who would be last, and with only Leo in opposition.

“You may as well claim your prize!” Luca said to Caleb, gesturing to Kai.

“How do I…” Caleb started, shrugging a little.

“However you want I suppose. We never said!” Luca shrugged.

Kai let out a whimper. His boyfriend was telling his best friend to make him cum. It was surreal but thrilling at the same time. He watched as Caleb deliberated for a moment, then reached down to grasp at Kai’s raging erection and started jerking him off. “Ah fuck,” he gasped. Tilting his head back to look at Luca, he added a feeble, “Don’t judge me if I cum quick. I’m CRAZY horny right now!”

“Shh,” Luca said as he reached down to place a finger on Kai’s lips, then grinned as he said, “There’s no shame in being premature!”

Kai frowned at the tease, but it dropped away quickly as he opened his mouth to suck on Luca’s finger for a moment, then released it and said, “Mmm, Italian spunk is tasty!”

The comment got a mix of laughs and groans from the other four.

“Shut up, don’t make me laugh when I’m trying to… y’know!” Leo said, shaking his head. Despite the apparent race between him and Miles, Leo’s hand had actually slowed.

“What if I can’t cum?” Miles whimpered, visibly struggling.

“Maybe you need help!” Kai suggested, then cocked his head to indicate for Miles to approach.

Miles looked torn. On one hand, cumming last meant doing a horrible forfeit, but on the other hand, getting sucked by Kai in front of the others was embarrassing. Opting for the one that didn’t end up with Miles learning what semen tastes like, he scurried over, pushed his underwear right down to his ankles and knelt with a knee either side of Kai’s head. Thrusting his cock down into Kai’s mouth as he basically sat on his face, he let out a muted moan.

“Okay, that’s hot. It’s not just me, right?” Luca giggled.

Leo and Caleb exchanged brief glances before blushing and returning to their wanking, Leo casually pawing at his own cock while Caleb continued teasing Kai’s, having slowed a little to prolong his torment.

“Okay, no judging… me… either,” Miles gasped as he felt Kai’s tongue swirling around his penis, “He’s just… very good at that!” Quickly showing he meant what he said, Miles yanked his cock from Kai’s mouth just in time to spurt his load out onto Kai’s chest, joining Luca and Caleb’s, his cheeks blazing red as he did it.

“Leo loses!” Luca declared happily.

“Fuck,” Leo said, suddenly speeding up. A moment later, he added another, “Ahhh fuck!” and began to ejaculate. It was quite spectacular, as his cock ejected several hefty spurts in rapid succession, hitting Kai’s torso hard enough to make a gentle splashing noise.

As Miles climbed off of Kai’s face, he inhaled sharply before he declared, “OH MY GOD!” and added his own load to the four covering him, his entire body convulsing as Caleb continued masturbating him right up to the point it became too sensitive and he had to swat the hand away.

Silence lingered for several moments, save for the sound of slow panting as the boys caught their breaths. One by one, the other four’s gazes turned on Leo, who blushed a little as he said, “Fine, whatever, okay, let’s just get it over with!”

“Yusss!” “Do it!” Lick him!” Luca, Caleb and Miles all called out at once.

Leo knelt by his twin’s side and made the stupid mistake of glancing at him. Seeing the amused but aroused look on Kai’s face, he rolled his eyes and leant down. He considered taking a gentle, cursory lick to see what it was like, but decided to be bold and just started lapping away at the puddles of semen covering the smooth, taut skin.

“Eww!” “Oh my god!” “Kinda hot!” “That feels weird!” the others chorused as they watched Leo licking away at Kai.

Despite the five loads covering Kai, it didn’t take Leo long to finish. Red-faced and with a slight shininess of spit and spunk around his mouth, Leo sat up and said, “Well that was absolutely fucking disgusting!”

“But ya did it!” Luca said, almost proudly. He looked round at the whole group and said, “You all did. I guess there’s no eunuchs here after all!”

“Okay, you are WEIRDLY obsessed with that word!” Miles smirked, pulling his underwear back up.

“Eunuch,” Luca repeated, “Eunuch, eunuch, eunuch… oh wait, eunuch…orn!? Is that where the word Unicorn comes from? I guess a boner without balls might kinda look like a horn!”

“Okay, it’s FAR too late for wherever THIS conversation is going!” Kai smirked as he sat up, gesturing to Luca.

“Yeah, I’m going back to bed,” Caleb said, heading for his mattress.

“Wait!” Leo called out, putting an arm out to halt Caleb. “How about… umm… well… that thing you mentioned…” As everyone looked at him, slightly confused, his cheeks reddened once again, having only just started easing off. “The… the bed thing… with the picture!”

“Fuck off, Leo. Tease me tomorrow,” Caleb huffed.

“No, I…” Leo objected, looking a little hurt. He glanced coyly at Kai’s bed and said, “I thought, I mean… after what we just did… maybe… we could all…” He didn’t finish the sentence, gesturing to the bed instead. The meaning was obvious.

“I dunno, five of us on one bed. That don’t leave a lot of room,” Miles shrugged.

“Oh no, we’ll be right on top of each other, how awful!” Kai said with a grin as he jumped onto his bed. “I’m up for it!” he said cheerfully. Looking at Caleb, he asked, “Whadda you say?”

Caleb gulped as he glanced at Kai, the only one still naked. He nodded silently.

“Great, come on, you gotta be in the middle!” Kai said happily.

“Yeah,” Leo said, giving Caleb a gentle nudge towards Kai’s bed, “This is YOUR fantasy after all!” Getting an angry scowl back from Caleb, he shrugged and muttered quietly, “I’m trying to be nicer but I’m not fuckin’ perfect, get over it!”

Caleb gave Leo a brief questioning look before getting shoved again towards the bed. All five of the boys started clambering onto the bed, with Caleb right in the middle. To one side, he had Kai nestled up against him, with Luca spooning against his back. Leo slid in on Caleb’s other side.

“Yeah, you’re gonna need to squeeze up or I’m falling off!” Miles said as he tried to get on the last little bit of space, shoving Leo’s back.

“Hey, here we are again,” Leo chuckled a little awkwardly as he found himself half on top of Caleb.

Miles clamped tightly onto Leo from behind. Though the two of them were not really cuddlers, they were used to sharing the smaller bed across the room, so it wasn’t really that different from usual.

The lamp was clicked off and then the squirming started. One of them would shift a little, which would make one of the others need to move a little to get comfortable, then another, and another. When they finally stopped moving, Kai asked, “Okay, okay, are we there? Are we actually able to sleep now?”

“This is so uncomfortable,” Caleb said with a slight headshake.

He got hums of agreement back.

“And so weird!” Caleb added as he felt the twins either side of him, as well as Miles’s arm draped over Leo to rest gently on him.

More hums of agreement.

“And I kinda love it,” Caleb admitted, chuckling gently.

There was a final, quiet chorus of agreements before the silence finally settled in properly and the boys began drifting off to sleep.