Daring Kai - Part 44 (Patreon)

“I call it… Daring Miles!” Leo said triumphantly.

Caleb scoffed, shaking his head as he said a rather blunt, “That’s shit!” As he got a scowl back from Leo, he shrugged and added, “Ooh, Miles is doing a dare so… Daring Miles. Lemme guess, when it’s Kai doing a dare you call it… Daring Kai?”

“No, I just call that a normal day now!” Leo said with a smirk, getting a snort of laughter back from Caleb. “Besides, it’s cleverer than it sounds,” he said defensively, “It’s like a… whadda you call it… double meaning. Yeah, Miles is doing a dare, but he’s also BEING very daring! Y’know, like… brave! He coulda so easily just said ‘fuck it, I’m not letting a teacher catch me wanking’ but he didn’t. He’s actually going through with it… which is very daring… AND a dare! See, it works on two levels!”

Caleb frowned thoughtfully, then nodded and said, “Okay, fair, not quite as shit as I thought, but I’m still keen to get back to ‘Daring Kai’!”

“Umm, yeah, me too!” Miles said, blushing heavily as he sat discretely masturbating. His discretion was largely unnecessary as it was only the four of them in the classroom as everyone else was at lunch. Even though he knew how this was going to end up, he was still cautious of being caught BEFORE he was supposed to be caught! “And may I say for the record,” Miles continued moodily, “You’re a buncha cunts for this!”

“Noted and ignored!” Caleb grinned.

“Yeah, I’d say I feel sorry for you, but lying is wrong,” Kai said with a wicked snigger. He did feel bad on some level. Miles and the others had put him through a lot of embarrassing things over the past couple of months, but he was wilfully complicit in them and had long passed the point of denying his enjoyment. Fun as it was to see the others get a taste of it, it was a little difficult to see them doing things they really didn’t enjoy.

“Lemme ask you a question, ya lil wanker,” Leo said, blushing slightly as he unsubtly looked at Miles’s penis, “If it’d been me that got this forfeit, or Cay… or even if it was Kai, would you have been nice and made us get caught by someone less embarrassing?”

“No,” Miles said with a headshake, “I completely understand and respect your choices and your right to make them!” He pouted for a moment before he added, “But I’m still entitled to think you’re cunts for making them!”

“Ah, don’t worry, it’ll soon be over, and you can all get back to tormenting me,” Kai said, standing up to pat Miles on the back as it was almost time for them to leave him.

“And Kai can get back to getting off on it,” Leo added with a nod.

“Yeah,” Kai agreed, then blushed and said, “I mean… shut up Leo!” It got amused chuckles from both Caleb and Leo as they got up to follow Kai towards the door.

They were in Leo and Miles’s form room. Their class would be due to come back in after lunch for afternoon registration, though thankfully Miles was not being made to get caught by their classmates. Instead, they had chosen Mr Langdon, their form tutor, who they always knew was in the classroom fifteen minutes before registration began.

Miles had been positioned perfectly so that he would be spotted the moment their teacher walked in, instructed to sit with his legs wide apart. They hadn’t gone as far as forcing him to strip naked, largely because that felt more like it would be harder for Miles to try and explain. They were aiming for embarrassment, not expulsion.

Just to ensure Miles had less chance of ‘performance issues’ he had been restricted from cumming for the last couple of days. He had been subjected to the same level of supervision that Kai had endured in the early days of their dare games, though unlike Kai, Miles had no punishments for failing, so his attempts to masturbate had been frequent. Somehow the others had managed to keep him under control and now, with a three-day load ready to blow, he was preparing to let it fly… in front of a teacher!

Always keen to immortalise his friends’ embarrassment, Leo had set up his phone in a concealed spot to capture the moment. He started it recording as the three of them headed out, probably a little earlier than they needed to, but keen to avoid bumping into Mr Langdon and ruining the surprise.

Miles sat alone in the empty classroom. Masturbating at school just felt wrong… well it actually felt great, but in theory it felt wrong. He flinched at every noise he heard, expecting the door to open at any moment. Part of him kept hoping that the others would burst in and tell him they were just psyching him out, that they weren’t REALLY going to make him go through with it. Sadly, there was no sign of them. He scowled a little, imagining them hiding in one of the nearby classrooms in anticipation of his total humiliation.

Caught up in his angry thoughts, Miles almost got carried away and had to suddenly clench everything to hold back from cumming. He had considered questioning the part where he had been ordered to time his orgasm for the teacher’s arrival. The forfeit had been to get caught wanking, not to get caught cumming, but he was determined to pay up and not give the others the pleasure of seeing him squirm.

Calming down from his near-orgasm, he grabbed his dick and started stroking again. Leaning back in his seat, he spread his legs wide and closed his eyes as he stroked. This couldn’t be happening. Something had to go wrong… or right!? There was no way…

The door rattled. Someone was coming in!

“Fuck!” Miles gasped as he gave himself a quick flurry of strokes.

As the door opened and Mr Langdon appeared, he stopped abruptly at the sight of Miles, just as his first shot of spunk flew.

“Nooooooo!” Miles whined, completely genuinely. He had done what he was supposed to… and it was mortifying. Despite the situation, and what was to inevitably follow, it was a wonderfully pleasurable orgasm, and the three days of spunk seemed to make it last forever as he sat holding his rigid prick and spattering the floor of the classroom with his seed.

“Miles, what the hell are you doing?” Mr Langdon asked, quickly realising he was standing in an open doorway. He stepped in and closed the door behind him. Seemingly regaining a little of his composure, he suppressed a smirk and said, “Well, I can SEE what you’re doing. I suppose what I mean is WHY are you doing it HERE and NOW?”

Miles had formulated a dozen wonderful excuses in his head – some simple, some elaborate, some shifting the blame elsewhere, some just deflecting a little – but every one of them vanished as he found himself caught in the teacher’s steely gaze. “I… was… really horny!” Miles managed to stutter.

Mr Langdon sighed and shook his head. “So I can see!” he said, nodding to the erection still tightly in Miles’s grip. “You should probably put that away,” he said, clearly still holding back a laugh. He wandered over to his desk as Miles quickly fumbled with his penis and his trousers to conceal himself.

“I… I… I’m… sorry sir,” Miles rambled awkwardly as he stood up, trying to catch his breath.

“Mmm-huh, well, first of all, here,” Mr Langdon said, holding out a box of tissues.

Miles frowned and started, “Oh, it’s okay, I wiped it on…”

“It’s for the floor!” Mr Langdon interrupted, shaking his head.

“Oh, yeah, sorry,” Miles said, somehow turning an even deeper shade of red. His face felt so hot he worried he might spontaneously combust! He accepted the box and pulled a few out before hurrying over to start wiping up his spunk from the floor.

“Now, Miles. I think we may need to have a talk,” Mr Langdon said as he sat on the front of his desk. He gestured to the desk right in front of it.

Miles placed the box of tissues back on the teacher’s desk, then looked at the balled-up tissues in his hand. He nearly put them in the small bin next to the desk, but blushed and instead squeezed them into a ball to slip into his pocket. He took a seat as instructed, remaining silent but still blushing profusely.

“Now I understand at your age hormones can… be a little uncontrollable and sometimes… make you think certain things are a good idea when they are not,” Mr Langdon explained.

Miles nodded his understanding.

“Such as masturbating in a classroom in the middle of the day!” Mr Langdon stated bluntly.

Miles winced. Hearing the man actually say it was almost as mortifying as being caught doing it.

“Now I don’t want you to feel bad… or guilty… about doing it,” Mr Langdon said calmly, “Because it’s a perfectly natural and healthy thing to do, but there are some considerations you should keep in mind for propriety!”

“Like… not doing it in school?” Miles ventured awkwardly.

“Exactly, Miles,” Mr Langdon said with a nod. “Now if you have questions or curiosities about things of this nature, you ARE welcome to talk to me, though I do suggest the school nurse is more equipped to handle questions of this nature if you have any.”

“I don’t!” Miles said urgently, “I’m sorry sir, please don’t report me!”

“Miles,” Mr Langdon said, shaking his head, “If I reported every boy who… gave in to those urges, we would have a LOT less students at the school!”

“So I’m not in trouble?” Miles asked, smiling hopefully.

“Trouble? No. But I’m not letting you off completely,” Mr Langdon said with a nod. “First… and MOST important of all, I will ensure to remind you of this incident – discretely – for the remainder of your time at this school, simply because I can and because it’s funny!”

“Great,” Miles blushed, though he did manage a slight smile, genuinely shocked to have not drawn anger from the teacher.

“And secondly, by the end of the week I want a one-thousand-word essay on the importance of discretion!” Mr Langdon ordered, getting a groan from Miles, “And lastly… I’m going to ask you to promise to keep things like that in a more appropriate time and place, okay?”

“I promise!” Miles said with an eager nod.

“Very well, then we’re done here,” Mr Langdon said, gesturing for Miles to get up as he stood and moved back round to his desk chair. He smirked as he added, “No need to stay, lunch break isn’t quite over… feel free to shoot off!” He sniggered at his deliberately suggestive choice of words.

“Oh my god, I hate my life,” Miles muttered as he blushed and shook his head.

*****

“Wait, wait, wait, here it comes!” Leo said giddily as he held his phone, showing it to Luca as they walked along together, heading home for the day.

“Feel free to shoot off!” Mr Langdon said on the recording, which perfectly captured Miles’s face as he heard the words.

Luca, who had already been laughing at the whole video, broke into absolute hysterics. Staggering against Leo, who was laughing just as much, the two came to a full stop and earned an angry glare from Miles, who was flanked by Kai and Caleb.

“It’s not THAT funny!” Miles pouted.

“Mate, it’s PRETTY funny!” Caleb said with a snigger.

“Feel free to shoot off!” Mr Langdon said as Leo replayed the final moment again. “Feel free to shoot off!” “Feel free to shoot off!”

“Oh… my god… stop,” Luca shrieked as he gripped onto Leo, laughing uncontrollably, “I’m gonna… wet myself!” He panted heavily, slowly calming a little as Leo stopped the replay. Luca stared at Leo, still gripping onto him. “That was… really funny,” he whispered, blushing a little.

“Yeah, it… it was,” Leo said back quietly.

“I hate you all!” Miles pouted as he continued walking now that the excessive laughter had stopped.

“Hey, if you don’t wanna hang out with us…” Kai called out, grinning round at the others as they caught on to where he was going with it.

“FEEL FREE TO SHOOT OFF!” the four of them called out in unison before promptly bursting into hysterics once again.

“Fuck every single one of you!” Miles snapped angrily.

“Ah, ahh mate, come here!” Caleb called out as he hurried to catch up to Miles as Leo started replaying the video again, this time for both Kai and Luca. “Chill, it’ll pass… eventually!” he smirked.

“I know,” Miles said with a grin.

Caleb frowned curiously at the sudden change in demeanour.

“I’m not even that bothered,” Miles stated honestly, “I’m just hamming it up for those guys. Look how much they’re enjoying it!”

Caleb looked over at the other three, who were all clinging onto each other and almost falling over as they revelled in Miles’s humiliation. He looked back to Miles and said, “Aww, you suffer for their enjoyment. That’s so sweet!”

Miles shrugged and said, “You know I like when Leo’s happy. Besides, we all gotta take our turn, right? It’s only fair to Kai! I still can’t believe he gets off on that stuff! When Mr L was talking to me, I was definitely NOT horny. He’s such a freak!”

“Yeah,” Caleb said, smiling fondly back over at Kai, “He’s…”

Miles frowned curiously at Caleb’s rather abrupt stop. Leaning close he started to grin and asked leadingly, “He’s… what?”

Caleb blushed as he realised, he had been staring. “Nothing. You’re right, total freak,” he sniggered. “Come on, let’s walk, they’ll catch up… or die laughing where they are. It’s their problem either way!” he said, hoping that moving on physically would also lead to moving on in the conversation.

“So…” Miles said after a few quiet moments, “How are things with Ellie?”

Caleb tutted and rolled his eyes as he said, “I knew that dick couldn’t keep a secret. Leo told you we broke up, didn’t he?”

Miles’s eyes widened as he said, “Umm… no, but YOU just did! What the fuck? You broke up? When?”

Caleb groaned at his own temper and pouted awkwardly as he mumbled, “About a month ago!” As he saw Miles go to react, he snapped, “And yes, I know, I shoulda told you all, Leo already tore me a new one about it. I get it!”

“No, that wasn’t what I was gonna say,” Miles said defensively, “Well… it was, but… good to know it’s been covered. I guess, firstly, are you okay and secondly… what happened?”

“Yeah, I’m fine,” Caleb nodded, “And… well… y’know… these things happen. It was a holiday romance and I think… being home, being back in real life… plus the travel time between us… it just… made things NOT work out, that’s all!”

Miles frowned and shook his head very slightly before he glanced back at the others who were lagging way behind, then to Caleb as he asked, “And there’s NO other reason?”

“No,” Caleb said, lying poorly, “But I don’t wanna talk about it!”

“Okay, well… I’m here if you ever do,” Miles said, then muttered, “Not that you ever will!”

Caleb chuckled a little at the comment, then fell silent again.

“Well, maybe I was too late to be the first one of us with a girlfriend,” Miles mused, “But maybe I can still be the first one to have a girlfriend who lasts more than a month!”

“Fuck, Miles! Too soon!” Caleb scoffed.

“Hey, just like the end of your relationship!” Miles joked.

“Jesus, you’re fuckin’ savage!” Caleb scoffed.

Miles sniggered and shrugged as he said, “Think of it as payback for laughing at the Mr Langdon thing!” He got a shrug and nod of acceptance back from Caleb. “So… what was it like anyway, y’know… having a girlfriend?” he asked curiously.

“Good while it lasted, I suppose!” Caleb replied, not really sure how else to answer it. He contemplated further for a moment, then let out an involuntary sigh.

“Sorry, should I stop talking about it?” Miles asked curiously.

“No,” Caleb replied, then looked round to make sure the others were still a safe distance away. “Look, can I… talk to you about something?”

“It’d make a nice change!” Miles answered bluntly. As he got a glare in response, he shrugged and said, “Sorry, yeah, go ahead!”

“Do you ever feel…” Caleb started, then paused, clearly thinking of the best way to put it. As he averted his gaze awkwardly, looking down at himself he spotted his school tie, striped with red and blue and an idea formed in his head. He nodded a little to himself and continued, “Do you ever feel like everyone’s telling you to be something? Like… imagine everyone’s spent your whole life saying… ‘You’re blue, you’re blue, you do blue things, cos that’s what colour you are’. But then you’ve got other people who come along and they answer it back and say, like… ‘I’m not blue, I’m red! I don’t wanna do blue things, I wanna do red things!’ Do you get what I mean?”

“Umm… yeah,” Miles said with a thoughtful nod. Despite Caleb’s rather clumsy attempt at an analogy, he was following along, but he also had a fairly good idea of the meaning behind it, though he chose not to press the matter. If Caleb wanted to avoid saying things directly, he would respect that.

“Yeah, so… you’ve got the blue people and you’ve got the red people and it’s like… everyone seems to know they’re red or they’re blue and sometimes it’s like… well, clearly I’m blue, look at me, look how blue I am, look at the blue things I do,” Caleb went on, “But other times, it’s like… I wanna do red things, I like these red things, I… like some of the red people. And it’s just really confusing because sometimes I feel blue and sometimes I feel red and it’s like I’m suppose to know which one I am but… but I don’t because… neither one of them… feels right!”

“Mmm-huh,” Miles hummed, nodding thoughtfully again.

“Sorry, that probably sounds proper mental, and you probably didn’t follow any of it,” Caleb sighed.

“No, I followed, and it doesn’t sound mental at all,” Miles reassured him, “I just… I wasn’t sure if you were just wanting to get it off your chest or if you’re looking for, I dunno… comments or thoughts or whatever!”

“You have thoughts?” Caleb asked slightly nervously.

“Yes, I do. Frequently. Unlike you bunch of idiots, my brain actually works!” Miles teased.

“Funny,” Caleb said flatly with a single eyebrow raise, “And kinda true, but… yeah, if you have thoughts, I’d like to hear them!”

“Okay,” Miles said. He looked back and saw the others had stopped again, once again rolling around in hysterics at another replay of the video. He smirked at their amusement, then stopped and waited for Caleb to look back at him. “So yeah, some people are blue and some people are red, and some people know that they’re blue or red, but… some people don’t. Some people figure it out quickly, some take a long time and there’s really no pressure to… pick a colour right away.”

Caleb nodded, smiling meekly at the reassurance.

Miles knew he could have stopped there. It was already good advice, but he thought Caleb needed to hear the rest. “You should keep in mind that, although yeah, most people are blue and… some are red, well… there are more colours out there. Some people are… yellow, or green or… or pink with orange stripes. The world isn’t red and blue… and I’m suddenly thinking this might sound better if you’d chosen ‘black and white’ but whatever!”

“Other colours,” Caleb mumbled, nodding gently as he looked thoughtful.

“Although, if you don’t mind me making a suggestion here,” Miles ventured, “Based on the whole red or blue thing… and what you just said… have you ever consider that maybe… you’re purple?”

Caleb stared blankly for a moment, taking in the comment. His eyes slowly widened as he thought about it. “Oh fuck,” he muttered quietly, “I… I think I need to go!”

“Cay, I’m sorry,” Miles said, worried he had really over-stepped.

“Oh, no, I’m okay, I’m good!” Caleb said with a smile and a nod, “I’m not upset or anything I just… I wanna take a bit of time to think. I’ll come over to Kai and Leo’s place a bit later, okay?”

“Okay!” Miles nodded, then watched as Caleb hurried away. He waited a few moments and gradually heard the sound of chatter getting louder as the other three caught up.

“Hey, where’d Caleb go?” Kai asked curiously.

Miles went to answer, then realised he almost missed a perfect opportunity. Holding back a smirk, he said, “Oh, he had something he had to do. He… had to shoot off!”

Kai, Leo and Luca burst into laughter once again as Miles feigned annoyance.

*****

Later that evening, with Caleb rejoining the group for dinner, they finished their usual after-dinner chores and headed up to Kai’s room for the evening.

“Oh my god!” Kai exclaimed as he casually scrolled through his usual array of daily messages, “Guess who got invited to Carl Kroeger’s Halloween party?”

“Everyone who’s shallow, vapid and popular?” Miles answered cynically.

“Me!” Kai declared, showing his phone to the others.

“I stand by my comment,” Miles muttered, getting a laugh and an elbow to the ribs from Caleb.

“Well, it’s hardly a surprise. You probably got more followers than him by now,” Leo said with a shrug.

Carl Kroeger was in the Year above them at school, and for the last four years, he had thrown Halloween parties that had proven to be legendary, though the guest list was always reserved to the most popular (or rich) kids at school. As an eager art student, Carl had always taken great pleasure in outshining everyone at his parties by having his friends sycophantically awarding him the ‘Best Costume’ award each year.

“Says I can bring guests,” Kai said thoughtfully as he sat down mindlessly into his desk chair, “Think they’ll let me bring four?”

“Three!” Caleb stated. As he got a curious look from the others, he shrugged and said, “Luca won’t let anyone see you talking to him at school. You think he’s gonna go to a party in public with you?”

“Oh yeah,” Kai said with a slight sigh.

“And make it two!” Miles added. He rolled his eyes as the others looked to him and said, “You wouldn’t catch me dead at that thing. Those guys are absolute bitches!”

“No, they’re POPULAR bitches, which makes it okay,” Caleb sniggered, “And chill, it’s just a party. They sound fucking awesome.”

“Also!” Leo said, then leaned in to whisper to Miles for a moment.

A grin slowly spread across Miles’s face as he listened to Kai. Nodding as he pouted thoughtfully for a moment, he said, “Okay, maybe I could be convinced.”

“Oh no, I can’t possibly imagine what they might be plotting,” Kai sighed flatly.

“Ah shut up,” Miles sniggered. “Anyway. Today’s done. Daring Miles is over, it’s back to Daring Kai. Someone wanna grab the bag!”

Leo’s hand shot out to grab at Kai’s crotch, grasping his balls.

“Not that bag, ya dick!” Kai laughed, slapping his brother’s hand away as Miles and Caleb cackled.

Leo let go and went to retrieve the dare bag.

“Please say get caught wanking, please say get caught wanking, please say get caught wanking!” Miles repeated, sitting with his fingers crossed.

Shaking his head in bemusement, Kai reached into the bag and pulled out a slip of paper. He had to unfold it one more time than usual, turning it into a bigger piece than most of the other dares. “Fuck me, who wrote the essay?” he asked as he looked at the elaborate description written down. His eyes skimmed over it briefly and he smiled as he said happily, “Aww, yay, this one includes Luca. Thanks for including him, guys!”

“What does it say?” Leo asked curiously.

“Okay, get comfortable,” Kai sniggered as he started to read it aloud, “Go to the park with Leo, Miles, Caleb and Luca and remove ALL of your clothes. Give your top/s to one person, trousers to another, underwear to another and footwear to the last one. They then get to go and hide somewhere in the park. You have to find them to get your clothes back. There will be clues to help you find them. Anything you don’t get within the time limit, you don’t get to wear to go home.”

“Woah, awesome!” Miles said, grinning excitedly.

“Jesus, that could… yeah, awesome!” Caleb agreed.

“I know, right!” Leo nodded, then suddenly gasped as he said, “Oh my god, that’s already pretty bad, but… we gotta make it worse!”

“Worse than THAT?” Kai asked, waving the paper emphatically. His heart was pounding, but the blood seemed to be rushing straight to his dick. “Okay, fine, ummm… ugh, god, I hate myself for this, but… even when I find someone with my clothes, I don’t get to put them on until the task is finished or the time is up!”

“Oh my god, that’s amazing!” Miles said, almost bouncing with joy at the prospect. “Umm… oh, I know! There should be some FAKE clues too, so he might take the time to go somewhere, just to find out nobody’s there!”

“Ah fuckin’ mint, mate!” Caleb declared excitedly. He looked a little guiltily at Kai and stated, “Sorry, but this sounds fun!”

“Yeah, for YOU!” Kai said, though he was now openly massaging a raging erection through his sweatpants, which undermined his reluctance a little.

“Oh!” Caleb said as he saw what Kai was doing, “Perfect! I know he’ll probably stay hard anyway, but just in case he doesn’t… any time your dick goes down, you stop where you are and can’t move til you’re hard again!”

“Shit,” Kai muttered, gulping at the thought of having to stand naked in a public place trying to get hard. “And you?” he asked his brother wearily.

“Yeah, let’s make it like the one in the Square… you can’t TALK to anyone, so you can’t ask for help, or ask if anyone’s seen us!” Leo suggested excitedly.

“Or explain himself if he gets caught!” Caleb added.

“You mean WHEN he gets caught!” Miles said, then gave a quick fist-pump in the air as he said, “Yuss, revenge!”

“Fuck,” Kai muttered at the thought of the dare, but couldn’t pass up one final opportunity to tease as he said, “That’s almost enough to make me shoot off!”

“Bastards!” Miles groaned as the others all laughed at him again.