Daring Kai - Part 18 (Patreon)

‘Normal’ is a subjective term. Being up all night and sleeping during the day is weird to some, but normal to a night worker. Being a grown-up with an imaginary friend is weird to some, but normal to a religious person. And being tied up all night with a vibrating butt plug inside you is weird to most, but had rapidly become normal to Kai. It was worrying how quickly that had become the case, barely a handful of nights, but by now he had gotten used to it.

One thing he had not gotten used to was the early wake-up call he had been getting from his brother and Miles ever since the plug got put to regular use. The last four mornings he had been woken up, tired and hopelessly horny as his morning wood positively throbbed from his nights of stimulation and long days of continuing abstinence. Ever since his sunscreen-induced orgasm and mutual masturbation with his twin later that same day, Kai had returned to being deprived of the pleasure of cumming. It was both frustrating and exciting.

Groaning at the noise of Leo and Miles barging into his room, Kai kept his eyes closed as he felt his wrists and ankles being freed, then grumbled, “It’s too early!”

“No, it’s not. Get up!” Leo insisted, poking his brother in the ribs.

“It is!” Kai insisted, “It’s the summer break. It’s meant for sleeping!”

“Maybe… we SHOULD leave him alone and let him sleep,” Miles said, shrugging a little at Leo.

“Better idea,” Kai said sleepily as he reached out and grabbed both of the other two by their wrists. He yanked them towards him so they tumbled onto the bed with him. “Get comfy,” he said as he let his eyes close again.

“What… why… what…” Leo stuttered a little awkwardly, but moving into place anyway.

The twins had nestled their heads together, forming a V-shaped space with their bodies that Miles found himself lying in. He felt Kai pull him up slightly so his head rested against the other boy’s chest as Leo slid closer to him, sandwiching him between them. “How is this a better idea?” Miles asked incredulously.

“I get to sleep in,” Kai said dozily, “And I get to do it knowing you two aren’t off… plotting something!”

“We don’t plot!” Leo argued.

“We… kinda do, actually. We plot a lot!” Miles corrected him.

Leo sniggered as he said, “Plot-a-lot. That’s funny!”

“Oh my god, shut up,” Kai grumbled, “Sleepy-time!” He threw an arm over Miles and onto Leo, letting his hand rest on his twin’s hip as he nuzzled his head against the other two boys. He quickly drifted off back to sleep.

*****

Miles awoke to the sound of gentle clicks. It took him a moment to remember where he was, but smiled gently as he felt the twins either side of him. As weird as it was to be in bed with two boys, it had been a wonderfully enjoyable and comfortable nap, but the quiet click that he heard again shook him fully back to reality. Opening his eyes, he saw the phone pointed at him as the sound of another picture being taken emanated from it. “Hey, stop that!” he called out, embarrassed to be seen in the compromising position.

“Wha…” Leo grunted as he suddenly awoke, rolled over and fell off the bed with a thud, and a pained proclamation of, “FUCK!”

Stirred by the sudden commotion, Kai awoke, opened his eyes and winced at the light. Shielding his eyes as he blinked several times, he glanced over to see the source of the issue and exclaimed a little too excitedly, “Caleb!”

“I don’t know what THIS is,” Caleb said, gesturing to the three of them, “But it’s FUCKING adorable!”

“You’re a cunt,” Leo groaned as he got up off the floor, looking slightly pained from the fall and annoyed at the laughter it drew from the others.

“Wow, greetings have gone WAY downhill while I was away!” Caleb sniggered as he put his phone away.

“I thought you weren’t back til Sunday!” Miles said, blushing a little but clearly trying to act casual to diminish his embarrassment.

“Oh, yeah,” Caleb said, the smile dropping away suddenly, “We… came back early!”

“Oh, really. We couldn’t figure that out ourselves!” Leo said sarcastically.

Kai looked over at Caleb. Knowing what he did about the other boy’s grandmother, his mind had jumped straight to the worst-case scenario, which was obvious from his expression. Caleb looked back, giving a gentle nod to indicate he was on the right tracks, but a meek smile to suggest it wasn’t quite as bad as it sounded.

“Looks like I’ve… missed a few things!” Caleb said with a knowing grin as Kai threw back the covers to get out of bed, casually revealing his nudity. He frowned a little as he saw the trailing cable and asked sarcastically, “Is Kai still on charge?”

Miles snorted with laughter as Leo gave a begrudging smirk at the comment, while Kai just blushed.

“No, it’s the butt plug,” Miles said bluntly, “He sleeps with it now!”

“By choice?” Caleb asked, eyes wide as he squirmed slightly.

“Yeah, but not his!” Leo replied with a wicked chuckle.

“Ha, nice,” Caleb laughed, “Hey, you guys wanna go grab a drink? I miss overpriced, sugar-filled crap that’s awful for me!”

“Sure, we can fill you in on what you missed while Kai gets ready!” Miles suggested. “We’ve had a really…”

Miles was cut off by the sound of Caleb’s phone ringing. “Oh, I should take this!” he said as he looked at who was calling. Seeing a renewed look of concern from Kai, he instinctively stated without thinking, “It’s just Ellie!”

“And Ellie is…” Miles prompted curiously.

Caleb blushed, wishing he hadn’t said anything. He looked from Miles, to Leo and then awkwardly to Kai as he said, “She’s… my girlfriend! Be right back!”

Kai felt suddenly empty… as he had just pulled out the butt plug. He also felt emotionally empty, though that was all down to Caleb.

*****

“Cum in your own face!” Caleb said with a sigh as he looked at the slip of paper. He rolled his eyes, shook his head and stated, “Can definitely tell I’m back with you guys!” He looked at the paper again and said, “It also says I gotta be naked and do it in front of you guys to make sure I don’t use any sneaky loopholes to make it less embarrassing!” He sniggered a little as he glanced at Miles and said, “It also says Miles is the best. I wonder who wrote this!”

“I don’t know, but they clearly have very good taste!” Miles said with a wry grin as he bounced playfully on Kai’s bed.

“Cay’s about to get a very good taste of himself!” Leo said with a teasing smirk.

“Well fuck my life!” Caleb grumbled.

“You mean fuck your wife!” Leo taunted.

Caleb rolled his eyes at the comment. Ever since he had told the others about Ellie, it had been a source of constant comment and teasing. He had met her on holiday and, in Caleb’s words, “We just hit it off right away!” The two had spent basically the entire holiday together and by the time Caleb and his family came home (early) they were officially boyfriend and girlfriend. Ellie lived relatively close by – close enough for them to see each other once Ellie got home, but not right on each other’s doorstep.

After Caleb had filled them in on that, Miles had taken great pleasure in recounting the events of the past ten days. He had taken particular pleasure in sharing all the details of the incident at the park and the embarrassment it had inflicted on Kai at first, and then Leo once he incurred Freddie’s wrath. Kai had done his best to downplay his brother’s embarrassment, mostly because he didn’t want him getting pissed and storming off as he was prone to do.

Once the four were all caught up, it had taken barely minutes before they agreed it was time to restart the dares. Heading back to the Robinson household, the dare bag had been retrieved and they worked out who was next to have a dare – Caleb.

“Are you even allowed to do shit like this?” Miles asked curiously as they contemplated Caleb’s challenge. “Won’t it be like cheating?”

“Oh,” Caleb stated, looking slightly embarrassed not to have even thought of that himself. “I guess… I’m only doing myself. I’m just… doing it with an audience!” He blushed at the comment, then quickly scowled as he said, “Dammit, why didn’t I say ‘yes, it’s cheating, and I can’t do it!’ Fuckwit!”

As Leo and Kai both smirked, Miles said thoughtfully, “I don’t know if three counts as an audience!”

“Hey, speaking of audiences, you seen Kai’s followers on Instagram?” Leo asked.

His brother’s smile could have been mistaken for a teasing one, but Kai recognised the rare look of pride on his twin’s face.

“Yeah, it’s like three-and-a-half thousand now or something!” Caleb said with a smile and a nod. He suddenly looked a little sheepish as he added, “I’m guessing!”

“Yeah, good guess,” Miles said with a knowing smirk. “But enough. Come on, it’s facial time!”

“Have I told you how glad I am to be home?” Caleb asked with a bemused eye roll. “Fuck, fine, okay!” he said as he started to strip off.

Nice tan,” Miles commented, just an observation rather than with any intent as he looked at the bulky, shirtless boy.

“You mean nice tan LINES,” Leo said with a smirk as Caleb got down to his boxers, a clear line showing around his waist and legs to show where his swim shorts had been while he was away.

“Guessing yours’d be more speedo-shaped,” Caleb taunted back, wiping the grin off his face as Miles and Kai both sniggered at the retort.

As Caleb pulled his underwear down with one hand and covered his cock with the other, Leo scoffed, “Mate, why you covering up? We’re about to watch you jackin’ it!”

“Meh, habit,” Caleb shrugged as he kept his hand there and looked round. “I, umm… do you… you don’t have to watch me the WHOLE time, do you?” he asked awkwardly at the thought of having to masturbate all the way to completion on his own with the others watching.

“Why would we want to?” Leo replied back a little too sharply. “Like… whatever, you… you…” he stuttered awkwardly as the others looked at him, “You do what you gotta do and we’ll… umm…”

“Spectate the climax!” Miles said with a grin, saving Leo from his awkward rambling.

“Okay, I’ll… I’ll… be over here,” Caleb said as he gestured over to the spare bed.

As Caleb crossed the room, Kai watched intently, staring at the pert mounds of his untanned buttocks, contrasting against the darker tone of his muscular back and legs. As he watched Caleb sit down, he quickly looked away when he saw the other boy begin to glance his way, attempting to act nonchalant as he pretended to be involved in Miles and Leo’s conversation.

Caleb got comfortable on the other bed and stared at his phone as he began masturbating, releasing his cock occasionally to tap at things on his screen.

“When you’re done perving,” Leo said, grinning at the immediate blushing it got from his distracted brother, “We’re talking about what you’re gonna have to do next!”

“Ugh, I forgot that bit,” Kai huffed at the thought of how much worse his own dare would be. He sat listening to his brother and Miles throwing around ideas for what they could make Kai do, but his eyes kept roaming back across the room to Caleb.

It wasn’t just the fact that a naked, thick, muscular boy was masturbating on his spare bed – though he certainly enjoyed that – it was the fact he hadn’t been able to speak to him yet. No chance to talk privately about why they had come home early, no chance to talk about their last night before he went away, no chance to… talk about his new girlfriend. Kai felt a knot in his stomach as he thought about it. Caleb seemed so happy and excited when he talked about Ellie, which made the slight feeling of resentment Kai felt all the more unpleasant.

“Okay, I’m close!” Caleb eventually called out, panting slightly as he suddenly yanked his hand away from his dick.

The others quickly dashed across the room as Caleb looked round to consider his options. Turning sideways, he walked his feet up the wall as he shuffled his shoulders closer to it, turning himself upside-down as he gradually moved his face beneath his throbbing dick. “Fuck,” Caleb muttered as he glanced at Miles, Leo and Kai. All three were staring at him, with both Miles and Leo recording it from two different angles.

Despite the nervousness from being watched, Caleb had gotten himself close enough to cumming that it didn’t take long to get himself back to the brink. With a sudden gasp, he closed his mouth tightly and clenched his eyes shut as he began to ejaculate, sending several hefty squirts down onto his own face as the other three laughed and cheered for him.

Kai was barely able to resist groping at his own dick as he watched, standing with his shorts shamelessly tenting. He looked at the gooey jizz smeared over Caleb’s face and licked his lips without even meaning to. He wanted to lick Caleb! To be fair, he usually wanted to lick him anyway, but now in particular.

As Caleb turned and allowed his body to flop heavily onto the bed, he let out a muffled grunt and waved a hand towards the others. While Kai and Leo both seemed content to leave him stuck with a faceful of spunk, Miles grabbed a towel and handed it to the blinded boy, who immediately began wiping his face clean. “Ugh, that was nasty,” he grunted as he got the cum wiped away. Suddenly very conscious of his own nudity, he climbed off the bed and hurried over to start pulling his clothes back on. Keen to also draw focus away from his own actions, he prompted, “So what’s Kai gotta do?”

“Mouth open!” Miles immediately blurted out, then shamelessly laughed as he said, “Just wanted to get that in first!”

“Predictable,” Leo said with an eye roll. “What’ve you got, Caleb?” he asked, still shaking his head a little at Miles.

“Umm,” Caleb hummed as his head disappeared into his t-shirt. As it popped out the top and he started getting his arms through the sleeves, he said cautiously, “He… has to do it with the butt plug in and vibrating!”

“That’ll speed things up,” Kai said before blushing a little at the slight over-share.

“Come on then, what’s yours?” Miles asked, cocking his head incredulously at Leo and his previous comment.

Leo grinned wickedly as he said, “He has to do it twice!”

“Oh, that’s original,” Miles said derisively.

“WITHOUT any break in between!” Leo quickly added as his grin broadened.

“Fuck!” Caleb exclaimed.

“Okay, that’s a bit more original,” Miles mumbled reluctantly.

“Oh come on, I can’t just… keep going when I finish. It’s… it gets… too sensitive!” Kai said, worried as much about being unable to comply as he was about the inevitable discomfort. Just as the others looked ready to offer their opinions, he gasped and added, “Fine, okay, then I say it’d be a lot worse if I was restrained and having someone else do it TO me, right?”

“Right!” “Yeah!” “I suppose!” the other three chorused back.

“So that’s my one. I get tied up and you all have to take it in turns doing it for thirty seconds at a time!” Kai explained. It was strange to be giving himself an unpleasant task, but enjoying the suggestion. He knew this was as much a challenge for the others as it was for himself. For Leo, making him touch his brother again when he had avidly avoided talking about their previous encounter was a good way to taunt. For Miles, who made it clear he enjoyed being touched, but not actually touching other guys it was an unwelcome task. And for Caleb… well, Kai just liked the idea of Caleb touching him! “And…” he added as the others looked uncomfortable, “Whoever makes me cum the first time has to just keep on going til I do the second, no stopping for anything no matter how much I beg and no passing it on to someone else!”

“Damn, I think someone’s been missing the dares!” Miles sniggered.

“Are we doing this or not?” Kai asked, both eager and nervous at once as he began undressing.

Once Kai was naked, the other three helped get him in position. Rather than being at the head of his bed, they secured his wrists with the restraints usually reserved for his ankles so they could all get easier access (and a better view to record it). Unlike Caleb, who had only positioned himself to cum in his own face at the climax, they lifted Kai up so his dick was pointed down at his face from the start. To support him, Caleb positioned himself behind the prone boy, so his naked body rested against Caleb’s bulky frame.

Humiliating as it was to be in such a position, Kai couldn’t help but enjoy the close contact with Caleb as he readied himself for the dare. As it was Caleb’s dare originally, he had been selected to go first, with the others following in usual dare order with Miles right after him and Leo after that.

Caleb reached around the upside-down Kai and grabbed his dick. It had been rock hard ever since the dare first started and was yet to go down, so the tip was slippery and gooey with precum. Having gone several days without cumming and several nights with the plug (which he had in once again) keeping him on edge, Kai had never been so eager and desperate to cum.

“Aaaaaand go!” Miles said as he started the timer.

Caleb was exceptionally red-cheeked as he effectively hugged the naked boy, one arm wrapped around him to keep him steady as the other started wanking his raging erection.

Between the abstinence, the embarrassment of the position, the buzzing toy and the gorgeous teen jerking him off, Kai could barely comprehend the extent of his arousal until he yelped after just five seconds, “FUCKING HELL I’M GONNA CUM!”

“Oh my god, already!” Leo called out, laughing but mostly just in shock.

“Mouth open!” Miles called out.

Kai didn’t need to be told. The sensation was so intense that his mouth was agape anyway, but he held it even wider as he stared up at Caleb’s hand pumping away as the orgasm ripped through him. It began to rain spunk. The first shot went cleanly between his lips, though the second went a little off target and caught him in one eye. A third shot followed, catching the corner of his mouth, letting some of the jizz dribble in while the rest spattered over his cheek.

On and on the shots went as Kai experienced one of the longest and heaviest orgasms of his life, feeling a constant spray of thick white goo squirting into his own face as Caleb continued pumping away. Struggling to swallow, Kai nearly choked but just about managed to compose himself. Swallowing again just as the orgasm subsided and the post-orgasmic sensitivity began to build, he yelped out, “Oh my god, stop, please!”

“You said no stopping, no matter how much you beg!” Leo said, nodding at Caleb to keep going.

“I’m… a fucking… idiot!” Kai whimpered, almost in tears from the extreme sensitivity, the pleasure so intense it was verging on pain. “Oh god… Caleb… Caleb… please…”

“Should I stop?” Caleb asked shakily, tightening the arm he had around the whimpering boy as his other hand continued wanking the still-hard, cum-drenched cock. He looked to Miles this time.

“Kai said not to stop and I reckon if you do he’ll regret it after!” Miles stated with a shrug.

“Fuck, okay, sorry Kai,” Caleb said, giving another squeeze. As he glanced down, he looked at the vibrating plug filling the naked boy’s hole. He dropped his head a little and pressed the toy with his chin, shoving it more firmly into him.

“Oh god, Caleb, FUCK!” Kai yelped as he trembled and whimpered helplessly. “Nearly… nearly… I’m… close again,” he gasped as he slowly felt the sensitivity fading and the pleasure increasing. “FUCK!” he screamed out as he began to shoot for a second time, unleashing a load much smaller than the first, comparable to one of his usual loads. Gasping from the intensity again, his mouth was agape and managed to catch most of the second load which he gulped down.

“All done,” Caleb said as he pulled his hand away from the embattled cock. Moving to the side, he gently lowered Kai’s body onto the bed and stared down at his sweaty, reddened, cum-covered face, looking into his one open eye. “You okay?” he asked softly as the other two released Kai’s wrists.

“You didn’t stop!” Kai gasped, shaking his head.

“Sh… should I have?” Caleb asked anxiously.

“Fffffuck no,” Kai said, venturing a slight, cummy smile, “That was amazing!”

“That’s one word for it!” Miles interjected, chuckling in slight disbelief.

“I think I need a shower!” Kai said, still panting slightly. “A regular one,” he added with a grin.

“Are they still supervised?” Caleb asked, glancing at the other two.

“Nah, we trust him to behave,” Leo said with a shrug, “Besides, I can’t see him knocking one out after that!”

“But feel free to supervise him anyway,” Miles suddenly blurted out, “Y’know… just in case!”

“In case of what?” Leo asked, giving Miles a curious frown and headshake.

“Just… just in case of… whatever,” Miles said back curtly, “We’ll be in Leo’s room when you’re done!”

“We will?” Leo asked before being dragged away by Miles.

Caleb glanced down at the sweaty mess of a boy still lying on the bed, smirked a little and said, “Here, I’ll help!” He grabbed Kai and lifted him off the bed with relative ease.

“What are you… oh my god…” Kai laughed as he was hoisted onto Caleb’s shoulder. “I can walk, y’know!” he giggled as he was carried through to the bathroom.

“Where’s the fun in that?” Caleb asked playfully as he locked the door and then placed Kai down to stand next to the shower.

Kai smirked as he replied, “Good point!” Still holding one eye shut from the semen gunking it up, he turned on the shower and waited a moment before he stepped in. Letting the water rain down over him to wash away the week’s-worth of jizz, he let out a content sigh.

“You… umm… you didn’t message,” Caleb said softly, curious rather than accusatory.

“Yeah, I… well… I kinda figured you might want time away from… y’know… everything,” Kai replied awkwardly.

“Oh, right, yeah,” Caleb replied, then went quiet as Kai continued washing off.

“So… girlfriend, huh?” Kai called out, then winced and shook his head slightly at the lameness of the comment/question.

“Yeah, it was… umm… yeah,” Caleb replied, staring at the vague silhouette of Kai through the steamed-up frosted glass.

Kai felt his stomach churn. Potentially it was the half-gallon of his own spunk not sitting right, though he suspected that was not the case and it was likely the result of thinking about Caleb being with Ellie. He took a deep breath in and exhaled slowly before he replied, “I’m… really happy for you!”

Caleb frowned slightly at the comment. While he came close to voicing his actual thoughts, he stopped himself and replied, “Yeah, I’m happy for me too!” He gave a slight chuckle. Keen to quickly move the subject on, he asked, “So how bad was it being stuck with dumb and dumber?”

Kai let out a grunt, then popped his head around the screen to shake it slightly as he said, “Oh my god, so bad at first. Kinda figured out they didn’t argue so much as long as they were working together on torturing me!”

“How selfless of you!” Caleb said with a snigger, “And… what I walked in on this morning?”

“Oh, that,” Kai said as he stopped the shower and reached around the screen to grab his towel. As he started drying off he explained, “That was the first time. I was just not in the mood to get up yet, so… I kinda dragged them into bed to make sure they didn’t do anything mean while I was sleeping!”

“Ah, sensible!” Caleb nodded, watching as Kai emerged with the towel wrapped around his waist. His scrawny naked torso was still slightly damp, glistening slightly as he stood before him. “And you get cuddles out of it too. That’s a win, right!” Caleb said with a sweet smile.

Kai pursed his lips. He already felt like he had held back too much about Ellie, but his resolve weakened a little and he stated honestly, “They’re not as good as you! I really like cuddling you!”

“You do?” Caleb asked as he stared at the half-naked boy wistfully.

“Yeah. Are we… I mean… with you having an… an Ellie now, are we… umm…” Kai asked a little uncomfortably.

Caleb stood and approached, stopping right in front of the shorter boy to grin down at him. “We can still do this!” he said as he put his arms around him.

“Good,” Kai sighed as he gripped onto the taller boy, his head resting against his chest and leaving a wet patch on his t-shirt. “I’m really glad you’re back!” Kai sighed.

“Yeah, cos it means more dares, right?” Caleb laughed as he let go of Kai and headed for the door.

“Yeah,” Kai replied absently, his mind wandering as he stared at Caleb’s back, “For the dares!”