Daring Kai - Part 2 (Patreon)

Kai shivered as he stood in the lounge, as much from the thought of what dare was coming his way next as from his near-nakedness and lingering damp from his dip in the lake. “Can’t I get dressed first?” he asked hopefully.

“Let’s wait and see what the next dare is first!” Leo said, grinning wickedly at his twin. He turned his attention to Miles and said, “Come on, let’s see who’s going next!”

Miles stood up and approached Leo with his hand at the ready for a round of rock, scissors, paper to decide which of them would be having the next dare. He promptly lost. With a dejected sigh he reached into the bag Leo was holding and pulled out a slip of paper. He opened it and read, then thought for a moment and smiled before he read out, “Next dare is to jerk off for thirty seconds in front of everyone!”

“Pfft, lemme guess, you’re totally bailing on it and just making Kai do it,” Caleb scoffed derisively.

“Actually, no. I’ll do it!” Miles said casually.

The comment certainly caught the others by surprise. Even being fully naked in front of each other was something they didn’t do (aside from Leo and Caleb in the showers after football practice). They certainly couldn’t (or wouldn’t) openly talk about wanking, let alone do it around each other. That was what made it so unexpected for Miles to be so willing to take the dare.

Kai felt a knot in his stomach at the thought of having to do it too, especially as it now meant the dare would be made even harder for him. At the same time, he felt an undeniable twitch in his cock at the thought of seeing Miles’s dick and seeing him jerk off.

“Okay, someone gonna time me?” Miles asked as he dropped the paper and remained standing in the middle of the room.

Caleb pulled out his phone, tapped briefly on it and then called out, “Okay, go!”

Miles reached down into his shorts and underwear… and didn’t pull anything out. His hand started pumping away, but it seemed he had absolutely no intention of showing the others his dick.

“Hey, no fair!” Kai whined.

Leo shrugged and said, “Dare didn’t say he had to strip or get his dick out. I’ll allow it!”

Disappointed as Kai was to miss out on seeing some skin, it was still exciting to think Miles was touching himself right there in front of them all. It was only the cold chill of his wet underwear clinging to his little dick that stopped him from swelling, though it did chub up a little.

“Okay, time’s up!” Caleb called out as he tapped on his phone to stop the timer. Without wasting a single moment, he looked to Kai and said, “So big fella, over to you. How you gonna make that… harder?” Leo and Miles both laughed at the deliberate double entendre as Kai just blushed at the question.

Kai shuddered again, though this time it was almost entirely from anticipation as an idea popped into his head. “H… how about… umm…” he stuttered anxiously, “I have to jerk off for 30 seconds… every minute… for 30 minutes?”

The others laughed a little awkwardly but didn’t look repulsed.

“Oh, like 30 seconds on, 30 seconds off, stop and start?” Caleb clarified, getting a nod from Kai. Smirking, he nodded back and said, “Definitely harder. You guys agree?” He got more nods, so he narrowed his eyes as he looked Kai up and down. “Okay, then… I say you gotta do it naked!” he said happily.

“Fuck,” Kai grunted. He knew it was probably coming, especially after Miles had abused that particular loophole, but hearing Caleb say it made it terrifyingly real.

“And he’s not allowed to cum!” Miles quickly added his contribution.

“Ah, so if he does, it’s a punishment. Nice!” Leo approved with an eager head bob. “For my one then…” he paused, contemplating the options. His eyes suddenly widened as a manic grin spread across his face. “You’ll be jerking off thirty times, so each time you do, you gotta say the name of a guy from your class at school and talk about him and what you think his sexiest feature and stuff like that while you’re jerking!”

Kai’s eyes widened in horror at the suggestion.

“Ohhh, that’s evil, I fucking love it!” Caleb said happily.

“I don’t… find any of their features sexy,” Kai lied shakily.

“Then pretend you do!” Leo said firmly. “If you don’t convince us that every single one of ‘em turns you on, then you earn a punishment!” he threatened, then let his grin grow even bigger as he added, “One punishment for each person you don’t convince us on!”

“Fuuuuck,” Kai groaned. Much to his dismay, his cock was already swelling at the thought of what he had to do. The fact he would be thinking (and talking) about his classmates while he did it just made it 100 times worse.

“Best get these off!” Miles said as he walked round behind Kai and yanked his wet underwear down.

Kai’s hands immediately grasped at his own crotch to try and conceal himself as he stood fully nude before his brother and friends. He was already red-faced, but blushed a little more as he heard, “Nice!” from Miles behind him as his butt was finally fully exposed to them.

“Why the fuck are you bothering to cover up?” Leo asked, shaking his head as he stepped forward and swiped Kai’s hands away. “Oh damn, he’s hard again already,” he said as he saw his twin’s cock at full attention.

Kai wanted the ground to open up and swallow him. Standing with his blonde hair still matted to his head and his scrawny naked body still covered in a fine sheen of moisture, he shivered once more now he was fully exposed. His pubis bore the smallest patch of hair. Though it was darker than the blonde mess atop his head, and darkened further by the wetness, it was still barely even visible from a distance. His dick, now at full erection, was a rather meagre 12.5 centimetres (that’s five inches, to save you looking!) with a plump hairless scrotum beneath, which had pulled up a little tightly from the chill.

“Wow, he really IS your LITTLE brother, isn’t he!” Miles sniggered, getting a pout from Kai as the other two laughed.

“Well let’s get to it!” Leo said as he took a seat on the sofa. “Miles, set a timer to go off every thirty seconds. Kai, when you hear it, you either stop or start. You can take the guys from your class in register order to make sure you don’t miss anyone. In fact, you can do it all for 31 minutes to make sure you get ‘em all!”

Kai gulped and cast his eye briefly across to Caleb. There were four classes in their Year group, with thirty-two students in each. Leo and Miles were in 10C, soon to be 11C after the summer break, while Kai was in 10D… with Caleb. That meant Caleb would have to be one of the guys he talked about while wanking!

“Ready to begin?” Leo asked, almost bouncing with glee as he held up his phone to record.

“Aww, Lee, come on,” Kai groaned.

“Right, enough of that!” Leo said with a heavy scowl. “I’m gonna be recording most of what you do, so from now on, any time you complain about it, you earn yourself another punishment AND we throw another dare in the bag!”

Kai wanted to argue, but he knew Leo well enough to know that he wasn’t bluffing. If he tried to fight back now, it would simply earn him exactly what Leo had threatened, so he huffed and said, “Fine, let’s get on with it!”

“Fine,” Leo said back firmly. “Miles, ready to start?”

“Yeah,” Miles replied, “Three, two, one… go!”

Kai heard the beep and grabbed his dick. It felt absolutely mortifying to be touching himself in front of the other three, though he knew part of him must have been enjoying it as he felt absolutely rigid between his fingers. Just as he saw Leo preparing to prompt, he started the other part of the task and thought about his class. Every morning and afternoon in their form room, their form tutor took a register so he was used to hearing the names of the other members of 10D in alphabetical order, so he started at the beginning and stated, “Amir Ahmad!”

“What about him?” Leo prompted when Kai didn’t immediately go on.

“I…” Kai paused, cheeks blazing crimson as he pumped away at his dick, going as slowly as he dared without being told off by the others. “I like his… skin!” he said a little awkwardly, then clarified, “I mean… the colour of it. It’s a really sexy light brown and when I see it I wonder if… if his… umm… if his dick is that shade or if it’s darker!”

“Jesus!” Miles gasped, “I’m convinced. Nobody’s making up embarrassing shit like that!”

As Leo and Caleb sniggered at Miles’s comment, Kai continued stroking, talking about Amir and blushing until he heard the beep of the timer and happily dropped his hand away. While he wasn’t close to the edge yet, he had gotten further along than he expected he would in 30 seconds. He wasn’t sure what was increasing his excitement so much. Was it being exposed to his friends? Being forced to pleasure himself? Thinking about his classmates? It was hard to tell, and he didn’t really have much time to think about it. Enduring the laughs, taunts and jokes from the other through the brief break, the timer soon beeped again and his hand found its way straight back to his still-hard prick.

Kai continued masturbating his way through the beginning of the register. Luke Bailey, whose dick he talked about, having seen it a few times in the changing rooms after PE. Freddie Baker, who Kai thought was just incredibly good looking, particularly his eyes which he blushed even heavier when he referred to them as ‘pretty’. Oliver Campbell’s most attractive trait was apparently his personality and sense of humour. Oakley Chapman was another boy who Kai had seen changing, though he talked more about his butt. Next was Jun Cheng, whose lips seemed to have caught Kai’s attention, apparently looking very ‘kissable’.

Leo, Caleb and Miles had been in fits of laughter throughout the challenge so far as they teased Kai about his nudity and his small dick and his almost non-existent pubes, throwing in the occasional taunt about the other boys he was talking about. They fell a little quiet as Kai began his next session, stroking his cock as he stated, “Caleb Clarke!”

“This’ll be good!” Leo muttered to Miles, sniggering as he playfully elbowed him.

Kai tried not to look at Caleb, but ended up doing it anyway, making brief accidental eye contact before he said, “I… I really like Caleb’s body. He’s… he’s thick and… muscular and he has really nice arms and I reckon he’d… he’d give… really great hugs!” Kai explained, feeling his cock throb and twitch as he slowly pleasured it.

“Ah, fuck man,” Miles guffawed as he reached across Leo to shove Caleb. “Y’alright there, hugger?”

“Kai, bro… that’s cringe!” Leo laughed.

Caleb just remained silent, blushing almost as much as Kai.

Glad to have Caleb out of the way, Kai found the rest of the boys in his class substantially easier to talk about now he was over the hurdle of talking about someone who was actually in the room. The challenge now became holding back from cumming. The 30-second break seemed to feel shorter and shorter each time. As he reached Noah Phillips, about two-thirds of the way through the class register, Kai was almost hitting edge each time he stopped. The wetness across his body from the dip in the lake had long since evaporated, but the moisture covering him now was a fine sheen of sweat as he desperately tried to hold back from ejaculating as he fantasised about his classmates.

Avoiding eye contact, Kai had to look somewhere and instead found himself looking at the crotches of the other three. Leo had leaned forward as he watched, and though it seemed to be to get a better shot for the recording, Kai couldn’t help but imagine it may have been to hide something too. Caleb had also made a move that suggested he was hiding an erection of his own. He had lifted one foot up onto the seat, so his leg concealed his crotch from the other two. Unfortunately for Kai, it now meant the bulge of his cock was more pronounced, turning Kai on even more as he tried not to stare.

“D… Diego… Smith…” Kai gasped shakily as he began stroking again, barely feeling like he had calmed down at all since the wank before. “He’s… he’s got… a lot of armpit hair already… which… which I’m not… into or anything but… it just makes him stand out more and… is… kinda… hot!” He let out a strained whimper as the timer went off again, signalling his next break. Only three left to go!

“I got pit hair. What’s the big deal?” Leo asked casually as he raised his arm and pulled back the sleeve a little to reveal his armpit and the small tuft of brown hair in it.

“Yeah, I’ve got a bit!” Caleb stated, raising his arm to do the same.

“That’s not hair, that’s lint!” Leo scoffed.

“Oh jesus,” Kai whimpered as he watched the two boys comparing body hair and arguing, adding a gentle groan as he saw Miles lift his arm to reveal his armpit.

“Smooth as a baby’s bum!” Miles chuckled, “Or Kai’s bum actually!” It got a laugh from the others as they turned their attention back to Kai.

“Oh god,” Kai panted as the timer went off again. Grasping as his dick, now slick with precum and almost painfully hard, he stated, “Xavier… Vincenzo!” He continued to pant as he thought about the other boy. “His… his accent is really sexy and… I really… I really like the way he says my name, it’s… I dunno, I can’t explain it but it’s hot! Ahh, fuck, I’m so close!” he whined just before the timer went off for him to stop.

“He’s totally gonna blow!” Leo sniggered.

“Wanna bet?” Caleb replied instantly.

“Sure,” Leo said eagerly, always happy to get one up on his rival. “He blows and YOU have to do the next dare with Kai, WITH the stuff making it harder!” he demanded.

“Fine, but he DOESN’T blow and you gotta do BOTH of your next two dares, no matter what they are, no passing!” Caleb demanded in return.

“Fine, deal!” Leo agreed, never able to back down against Caleb.

Kai gulped as he imagined the possibilities of what he had just witnessed. On one hand, if he blew before the end he would be punished, but he would get to see Caleb doing the next dare with him. On the other hand, seeing Leo forced to do whatever dares he drew out was just as enticing. The timer beeped and any thought of intention disappeared as he just focused on his dick and the next name. “Luca Ward!” he stated as he stroked himself, “I think he’s REALLY fucking brave to be out at school but he’s also just so fucking cute. I just wanna pick him up and hold him and kiss him and treat him like my own little teddy bear. He’s adorable!”

“Awww,” Miles said softly. As he got bemused looks from the other two, he stated, “What? That’s so fucking cute!” He shrugged dismissively at the looks he got as the timer stopped.

They all looked at Kai expectantly, and though his small erection dribbled up a bead of precum that stretched most of the way down to the floor before dropping off, he didn’t ejaculate.

“One to go!” Caleb said happily.

“He’ll blow!” Leo said, though his face didn’t bear the same level’ of confidence as his tone. “Kai, try not to think too much about cumming, or having us watching you, or the fact I’m recording you!”

“Shut up Leo,” Kai groaned, his cock oozing up and glob of clear goo.

“I believe in you, Kai. You can hold back, I know you can!” Caleb said.

As self-serving as the cheer was, Kai still smiled at the vote of confidence.

“I don’t care what happens, I’m having fun either way!” Miles said with a casual shrug. “Time for the last round,” he said as he looked at his phone and saw it about to beep.

As the tone sounded, Kai gasped as he grabbed at his wet, sticky cock. “Finley Watson!” he declared the last name on the register, “He has a really big bulge and I reckon he’s got a massive dick and probably really big balls too and I’d love to see them and see if I’m right! I bet he’s massive and not just long but thick too and I bet he cums a fucking bucketload. Oh my fucking god, oh god, I’m SO close!”

As the timer beeped, Kai let out a whimper as he clenched his eyes closed and strained every muscle in his body to hold back. Somehow, through sheer strength of will, he managed to stop himself ejaculating, though he did dribble another massive drip of precum.

“Yussss!” Caleb called out excitedly as he jumped up to celebrate. “Ha, in your face, Robinson!” he said, pointing at a very unhappy-looking Leo.

“Wow, looks like you enjoyed it as much as Kai did!” Miles suddenly interjected, getting a cackle from Leo as they both looked at the bulge and heavy wet patch in his sweatpants.

“Oh, like you two aren’t boned up!” Caleb snapped, sitting back down with his arms across his lap.

“I’m not!” Leo insisted.

“Me neither!” Miles added.

“Prove it!” Caleb challenged them.

“I… don’t have to!” Leo said evasively. “Besides, this isn’t about us!” he said in a poor attempt at deflection.

Kai stood watching the squabble, panting as he slowly began to ease back from the edge. He had literally never been so close to cumming before without actually doing it. He wanted release, desperately, but as he thought about it, he remembered the punishment he had been given… no cumming all summer, unless dared! That was going to be hard… in every way!

“We should pick the next dare!” Miles suggested excitedly.

“Nah,” Leo said dismissively, “I wanna keep this game going, but we can’t knacker Kai out too quickly. Mum and dad may not be around much but I’m pretty sure they’d noticed if we worked him to death!” It got wicked sniggers from the other two, their squabble immediately forgotten.

“Does that mean I can get dressed now?” Kai asked, glad to finally heard some good news, though he suspected the delay was more for Leo to put off his own dare than to actually help him.

“Hmm, how about this… we’ll let you get dressed and have no more dares til tomorrow… if you take a punishment!” Leo suggested.

“What? Why am I being punished? I didn’t do anything wrong!” Kai argued.

“Don’t think of it as a punishment, think of it as… payment for our mercy!” Miles said with a broad grin.

“Nice!” Leo nodded, offering Miles a fist-bump.

“Fine, just… draw me one then so I can get dressed!” Kai sighed.

“Care to do the honours?” Leo asked as he grabbed the bag and offered it to Miles.

“Gladly!” Miles said with a nod as he reached into the bag. He pulled out a slip of paper and immediately read out, “Remove your pubes using just a pair of tweezers!”

“What? No way, that’s… no way!” Kai groaned as he heard the others laughing hysterically at the punishment seemingly provided by Miles.

“Are you refusing to do it?” Leo asked, sounding almost hopeful.

Kai’s shoulders slumped as he shook his head and said, “No, I’ll do it!”

“Great, I’ll be right back!” Leo said as he jumped up and dashed out. He returned a moment later brandishing a pair of tweezers that he tossed to Kai and stated, “There ya go. You can do it in here, cos you know we can’t leave you unsupervised in case you… y’know!” He gave a wanking gesture with his hand.

“I won’t wank!” Kai pouted, blushing at even using the word.

“No, you’ll tweeze!” Miles giggled. “Get to it, baldy!”

Seemingly disinterested in watching the slow monotonous task, Leo, Caleb and Miles started playing video games as Kai sat beside the TV, hunched over with his legs spread as he plucked hair after hair, wincing a little with each one.

From where the others were sat, they could see perfectly between Kai’s splayed legs, showing off his softened prick, his loosened balls and any time Kai leaned back a little, a brief glimpse of his butthole.

After what felt like forever, and with a small pile of hair on the floor in front of him, Kai declared, “I’m done!”

Leo paused the game and instructed, “Come over and let us inspect!”

Kai rolled his eyes as he stood and approached the three other teens, painfully aware of his ongoing nudity. He felt his cheeks redden again as all three leaned in to take a close look at his now hairless pubis. The attention had an almost instantaneous effect and as he felt himself being scrutinised, his cock twitched and throbbed it was way to a full erection once again. It drew even more laughter and taunting than he expected as he stood exposed before them.

“Yeah, you missed a few!” Leo instructed as the laughter at the boner died down, “Miles, pluck the rest!”

“Why should I do it? I don’t wanna touch his giblets!” Miles recoiled.

“Don’t look at me,” Caleb said, pulling back from the other side.

“Fine, rock, scissors paper for it!” Leo huffed.

A quick three-way game later, Caleb was the loser and reluctantly held out his hand to take the tweezers from Kai. He reached out with them to grab an errant hair and tugged it out, hearing a slight wince from above. As Kai jerked a little, his dick bobbed from side-to-side. Caleb’s hand jerked away as the sway of Kai’s movement made the rigid dick touch the side of his hand.

“Geez, get over it,” Leo scoffed. “Just grab his fucking dick and hold it out of the way or we’re gonna be here all fucking day!”

Caleb gulped as he glanced up at Kai, then back down to the erection. He had literally never touched a penis other than his own and he had certainly not expected that to change today. Taking a deep breath, which he realised resulted in him inhaling the scent of sweaty balls, lake water and precum, he grabbed Kai’s dick and held it down, out of the way of his pubis. He reached out and began plucking the final few stray hairs.

“Oh god, oh god,” Kai whispered shakily as he stared down at it and felt Caleb’s fist gripping onto his small boner. “No, no, no, no,” he whimpered but it was too late.

Caleb took a moment to realise what was happening. He felt the dick in his hand throb but thankfully wasn’t in the path of the shooting spunk, which flew between himself and Leo, who jumped away like it was a grenade about to go off. Caleb jerked his hand away, which allowed Kai’s dick to spring back upwards, flinging a streak of spunk into the air as his dick slapped against his stomach.

“Oh god, no,” Kai whimpered as his cock spasmed spurt after spurt of spunk up into the air and over himself, dripping down his chest, stomach and now-smooth crotch as it started dripping onto the floor.

“Damn, Caleb’s good!” Miles sniggered.

“Oh Kai, how embarrassing!” Leo taunted as his brother barely even finished ejaculating. “And more importantly… you just came without it being part of a dare. That means you need ANOTHER punishment!”

“Ugh, fuck my life!” Kai grumbled as he stepped backwards shaking his head at himself.