Author's Note – The basis of this story was inspired by a story I read elsewhere about the same concept (a teen who asks for dares and then makes it worse for himself). Unfortunately, I can't remember what it was called or where I read it, so if you happen to know of it, please let me know so I can credit the author for the inspiration. If you have any questions or comments, my email is always open at matterotica@hotmail.co.uk.
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Finally, check out the links at the end for details of my other stories. For any fans of my previously posted story `The Humiliation Games', the sequel story is currently in progress on my patreon, why patrons can vote each week on what happens next. As always, the story will be posted on Nifty once complete too, because Nifty is great (did I mention, consider donating!!)
Daring Kai ----------
Chapter 01
It was only two days into the school summer holiday and the boys were already bored! Twin brothers Kai and Leo Robinson, along with their two best friends Caleb Clarke and Miles Beston, all fifteen, intended to spend most of the summer together as they had every year since they were six. With their parents happy that the boys were now old enough to be left unsupervised, the four boys were facing six weeks to do whatever they wanted... and they already had nothing to do!
"We could play truth or dare!" Kai suggested with an impish smile.
Despite being Leo's twin, Kai was very much the `little brother' of the group. As fraternal twins rather than identical, the two boys couldn't look more different. Kai was short and skinny, Leo was tall and muscular. Kai looked young for his age while Leo looked mature beyond his years. Kai was blonde while Leo was a brunette. The only physical trait they did share was their piercing blue eyes.
"Oh my god, give it a rest Kai," Leo huffed. The four of them had played truth or dare several times over the last couple of years, though realistically they didn't even bother with the truths and instead just skipped to the dares. "You know it always ends up the same way!" Leo added, giving a disapproving look to their two friends.
"What?" Caleb shrugged dismissively, "You give me stupidly risky dares and I'm just not gonna do them. Why would I wanna do stuff like that?" Caleb always enjoyed disagreeing with Leo, the two sharing a relationship that was as antagonistic as it was friendly. Standing only a little shorter than Leo but a similar weight, the two were rivals in any sport they played and any game they took part in, always keen to out-do each other. Sporting jet-black hair, brown eyes that were so dark that they almost looked black too and a dashing smile, Caleb was undoubtedly the most conventionally attractive of the group.
"It's not a dare if it's something you already wanna do!" Leo said, rolling his eyes.
Kai watched intently. He really wanted them to play, if only because it meant there was a chance to see some of the others partially or fully naked, or maybe even doing some of the `naughtier' things their last game had come close to involving.
"Fine," Miles agreed, "But then why would we wanna play a game that involves us doing things we don't wanna do?" He gave a cocky grin at the obvious logic of his point. Miles was a mischievous-looking, chubby-cheeked boy who was slightly on the shorter side of average height and a little on the chunkier side of average weight, certainly not fat, more just boyishly plump. His ginger hair always seemed to be a mess, even when it was tidy, while his adorable deep green eyes seemed a little bit magnified by his thin-rimmed glasses that he didn't wear anywhere near as often as he should.
"That's the fun of it!" Leo argued, "It's about making everyone ELSE do stuff they don't want, not doing it yourself!"
Kai was glad to have Leo arguing FOR the game. If the other two hadn't been arguing back with him, he likely would have been opposed to it simply because it was Kai's idea. As it was, his brother had taken to fighting for his suggestion and Kai was happy to silently let it play out for now.
"Fine, we'll tell you guys to do stupid things you don't wanna do and then laugh at you doing them," Caleb suggested with a smirk.
"Yeah, not happening, dickwad!" Leo snapped back.
"How about..." Kai started, the words leaving his mouth before he even had the chance to register the stupidity of what he was saying, "... if we have it so that if you get a dare that you REALLY don't want to do, then... I'll do it instead?"
The other three looked at him, then exchanged glances and shrugged at each other.
"Why... why would you..." Miles started but was cut off by Leo raising a hand.
"What, and you'll do it, no matter what it is?" Leo asked.
Kai gulped slightly. He was already regretting the offer, but something about it also felt... exciting! He could feel his dick thickening just a little. He had gone into this keen to see the others doing dares, so why was he now so interested in doing them himself? Again he spoke without thinking as he replied, "Yeah, if you don't wanna do it, then I HAVE to do it, no matter how bad it is!"
"Now that's a different game altogether!" Caleb said with a grin.
Miles shrugged and said, "Just sounds like us giving Kai a buncha dares. Why would we ever do one ourselves?"
"Oh! I know!" Caleb quickly replied. Grinning broadly, he paused as the others glanced at him, Leo and Miles intrigued while Kai looked understandably nervous. "If we choose not to do the dare, Kai's gotta do it, but..." he paused to build the tension, grinning again, "If we DO choose to do it, Kai has to do it anyway, but we get to add something in to make it harder for him!"
"What?!" Kai gasped anxiously.
"Oooooooh, that's interesting!" Miles said, staring at Kai excitedly.
"Nah, we can do better than that!" Leo smirked. He gave his twin a brief sideways glance and held back a smirk at the nervous expression, then said, "If we do the dare, Kai's gotta do it too, but HE has to suggest something to make it worse and then ALL of us get to add something else in TOO!"
"Yessss!" Miles hissed excitedly, "And if his idea doesn't make it hard enough, he gets a punishment to do as well!"
"Fuck yeah, this sounds fun!" Caleb said, almost bouncing out of his seat.
"Wait, don't I... I mean... I didn't..." Kai stuttered. It had all escalated so quickly, and though he felt the continued stirring in his groin, the whole idea was increasingly terrifying.
"How many dares do we do?" Miles asked, clearly ignoring the smaller boy's trepidation.
"We should each write down five," Leo suggested, "Then we can draw them out at random so you might even get your own dare! And if you wanna do ones that take a while, y'know, like... do something every day for the summer break or whatever, throw them in too. This shit could keep us going all summer!" He was already busying himself with grabbing some paper and pens to write down their dares.
"Oh, how about if we do the dare, we get to write another one and add it to the pot!" Caleb suggested, getting immediate nods of agreement from the others, except Kai.
Leo passed out paper and a pen to each of them, then grabbed two small bags. On one he wrote dares' and on the other punishments'. "Put as many as you like in here," he said holding up the punishment bag before starting to write down his own ideas. As he saw Kai just sitting and staring, he added, "Come on, you too. We've ALL gotta write dares, but leave the punishments to us!"
Kai let out a gentle whimper. He felt like he should stop this before it started, but the other three all seemed too excited by the idea that pulling out now would likely earn him either the silent treatment for the rest of the summer, or a quick beating followed by being forced to play anyway, so he just got to work writing down his ideas.
Several minutes later, twenty dares had been written down, folded up and put into the dare bag, while several punishments had been added to the other.
"So who's going first?" Leo asked, looking to Miles and Caleb, "Rock paper, scissors?" Getting a nod of agreement, the three boys quickly played, coming out in a tie before playing again with Caleb losing to the other two. "Looks like you're first, Caleb!" Leo said with a wicked grin.
"Fine, let's see what Kai's gotta do," Caleb said with a snigger. He reached into the bag and pulled out a piece of paper which he unfolded and read to himself. He smirked and said, "Yeah, I ain't doin' that!" Shaking his head, he read out, "Run to the corner and back in just your underwear!"
"Boo! Chicken!" Miles taunted.
"Hold up," Leo said with a smile, not even looking Kai's way yet. "I can understand not wanting to do that, but remember, if you do... we can make it even worse for Kai!" He paused to grin for a moment before he added, "HOWEVER we want!"
"Ooooh," Miles cooed with a massive grin.
Kai quickly interjected, "No, if he said he won't do it..."
"Nuh-uh, I didn't decide yet!" Caleb silenced Kai, then looked to Leo for a moment. Considering the possibilities, he nodded and said, "Okay, fine, I'm in!"
"So what's Kai gotta do?" Miles asked excitedly.
Leo stood, shaking his head as he said, "Nuh-uh, first Caleb's gotta actually DO the dare, THEN we decide about Kai, so come on, get streaking!"
Caleb huffed as he started undressing.
Kai gulped as he watched Caleb remove his t-shirt. He wasn't as ripped as Leo – not that he looked at his brother in the way – but he was certainly a lovely sight to behold. Clearly defined pectorals with just a hint of thickness about them, slight tufts of dark hair in his pits and below his navel, with a stomach that bulged a little from a mass of undefined muscle. As he pulled down his sweatpants to reveal a pair of black Calvin Klein boxer-briefs, nestled around a small package, his thick legs slid into view, peppered with black hairs that grew thicker towards his shins.
"So, to the corner and back?" Caleb clarified.
`The Corner' was simply the end of the street Kai, Leo and Miles lived on, forming a T-junction with the road Caleb lived on. It was their usual meeting spot any time the four of them went out or headed to school. It wasn't particularly far away, with just a dozen houses between it and the Robinson household, but it felt pretty far to Caleb as he considered his run.
With the dare confirmed and Caleb suitably undressed, they all headed outside with Caleb flinching slightly as he felt the warm afternoon air swirling around his exposed torso and legs. He was keeping his hands firmly clenched in front of the bump of his privates.
"And GO!" Leo shouted to start him off. They all stepped out onto the street and watched as Caleb took off at a mad dash for the corner.
Caleb seemed to close the distance in no time and was soon turned to head back towards the others who started cheering for him as he approached. Caleb looked unhappy about the ruckus and its likelihood of drawing more attention. He charged his way through the group and into the house as the three laughing boys followed. Moments later, before the other three had even started up the stairs, Caleb reappeared, re-dressed.
All attention started turning to Kai who suddenly looked nervous again.
"Well, he did it," Leo said with a wicked grin, "So now it's Kai's turn. Let's hear your idea for how to make it harder!"
"Fuck," Kai muttered. His brow furrowed as he thought about it for a moment and said, "How about... instead of the corner I have to go all the way to Hanson Park?"
The other three exchanged looks for a moment then nodded their agreement before Leo prompted, "Miles, what you gonna add?"
"He's gotta walk instead of run!" Miles said, getting laughs of approval from Caleb and Leo as Kai groaned.
"Caleb?" Leo prompted.
"He..." Caleb paused, contemplating the options before he smirked and said, "He's not allowed to cover up or hide no matter who comes along!"
"What?!" Kai gasped.
"Nice!" Leo said with a grin, ignoring his brother's shock. "Well for mine then..." He paused as he looked his `little' brother up and down, then shrugged and said, "We're just getting started so let's not get too mean... yet! When you get to Hanson Park, you gotta jump in the lake before you walk back!"
The suggestion got uproarious laughs from the other two as Kai just whimpered. Thankfully, the fear of the task had quickly shrivelled his dick back down from watching Caleb's run, so at least he wouldn't be sporting a boner as he stripped off. Already feeling self-conscious as he began to undress, the teases and taunts from the other three only made the feeling of exposure even stronger.
"So scrawny!"
"Has he even STARTED puberty?"
"I've eaten things bigger than him!"
While Leo could probably pass for seventeen at a push, and Caleb still looked fifteen, albeit a very well-built fifteen, Kai was not quite so blessed. With his clothes on he looked a little young for his age, but as he pulled his t-shirt off to reveal his pale, scrawny torso and slender arms, all completely bereft of hair, he looked closer to thirteen. As he reached to pull his jeans down, he let out a groan. While he had thankfully stopped wearing tighty-whities a couple of years ago, he was clad now in a small pair of white boxer briefs that barely even bulged from his small dick.
"Come on, let's do it!" Leo said, urging Kai towards the door the moment he was down to his underwear.
"And remember, no covering up, no hiding!" Caleb added as they headed out.
"And no running!" Miles insisted, "We'll be right behind you. If you go too fast, you earn your first punishment!"
Kai whimpered again as the others laughed sinisterly. He took a deep breath as he started down the driveway. As he stepped out onto the street, he cursed himself for his own suggestion. The corner was only a minute away at a walking pace. Hanson Park was easily ten times that, maybe more. Ten minutes of walking, plus ten minutes of walking back. Twenty minutes of being out in public in just his underwear, which would be wet for half of it. He was sure he had had nightmares less scary than that.
Almost as soon as he started down the street, a car sped past. He went to cover up but just managed to hold back, blushing profusely as the car honked its horn at him. He heard a wave of laughter from behind him as Leo, Miles and Caleb followed, clearly enjoying the show. As the sudden realization occurred to him that the others were staring at his back, including his butt which was virtually on show squeezed into the tight underwear, he felt the stirring in his groin return once again.
Kai felt himself getting hard and wanted nothing more than to cover it up as he crossed the street to keep heading towards the park, but he knew if his hands left his sides the others would notice, and he would be punished for it. While it did mean his (small) tent would be on show to anyone who passed, at least the others were behind him and couldn't see his shame.
He continued on down the street, shuddering a little every time the breeze licked at his exposed torso. His nipples were rigid, poking out ahead of his non-existent pectorals while his erection continued to press against the inside of his underwear. Thankfully nobody was walking the route he followed, though three more cars passed him on the way, two approaching from ahead and one from behind. Two of them beeped at him, while the other clearly noticed but didn't react.
As they reached the gates to the park, Kai could see the lake ahead. Worried the others would catch up to him and spot his erection, he continued walking as fast as he dared and promptly jumped into the water. He let out a muted shriek as the coldness enveloped him. It may have been a warm day, but the water still had a severe chill to it.
Turning to face his hysterical brother and friends as he knelt in the shallows, he asked, "Happy now? Can I go home?" His face suddenly dropped as he saw what was in his brother's hand... his phone. He was recording. "What are you doing? Stop it!" he said desperately.
"Yeah, I don't think so. This stuff is gold. Besides, how else are we gonna make sure you keep on playing?" Leo sniggered, getting more sinister laughs from the other two. "Now come on out, LITTLE brother. And remember, NO covering up AT ALL!"
"Aww, Leo, come on, I'll keep playing. Just... don't record it. Please!" Kai pleaded.
"If you're not out of that water in the next five seconds, you earn yourself a punishment!" Leo replied mercilessly.
"Fuck," Kai muttered, then stood. On the bright side, the cold water and shock of realising he was being recorded had shrunk his dick back down again. In fact, it had probably shrunk him even smaller than usual. That might have been okay had he been dry, but he quickly realised as he stood that his underwear had now turned almost completely transparent, putting his shrivelled cock and meagre balls fully on show to the other three teens. He looked tiny, which was probably why all three were laughing uncontrollably at the sight of him.
"Oh my gosh!" a voice suddenly declared from the nearby path.
Kai turned to find a middle-aged couple standing there looking almost as shocked as he did himself. Instantly his hands clamped over his crotch as he declared, "I was just cooling off!" before he turned and ran for the gate with the others close behind him. He stopped as he got back to the street and dropped his hands to his side, hoping that the humiliation of being seen might be enough to distract the others from his brief cover-up.
"Wow, nice buns!" Miles called out with a snigger.
"Full moon tonight!" Caleb added, even though it was the middle of the day.
"It's the only big thing on him!" Leo added with a wicked smirk.
Kai, already red-faced, blushed so intensely he was sure he could feel steam coming off himself. The water trickling down his body was a constant reminder of his nakedness, especially as he felt the wind licking across him. The comments brought back the same feelings from before, especially now that his butt cheeks and crack were completely visible through the tight, wet fabric. Despite the cold wetness and the fear of being seen, his cock began to swell once again. Soon enough, he was at full mast with the tip of his boner stretching out the wet cotton, pulling it away from his pubis, leaving only the head and the small bulge of his balls visible through the transparent material.
The walk back felt torturously long, especially as there seemed to be a sudden influx of vehicles passing by, with seven approaching from ahead and getting an eyeful of his small erection while five passed from behind and honked at the sight of his plump little butt.
"Hey bro, turn round and give us a proper look!" Leo called out as they got near to the house again.
"That wasn't part of the dare!" Kai pouted, shouting back over his shoulder without turning.
"No, but do it anyway!" Leo called out, his tone firm.
Kai sighed. He knew if he didn't they would likely just make him, so he stopped, let his shoulders slump and turned, ready for the onslaught of taunts of laughter. He got exactly what he expected as they once again burst in hysterics at him.
"Oh my god, is he hard!" Caleb guffawed.
"If you can call that a boner!" Leo sniggered.
"Did you enjoy this?" Miles asked in shock.
"Can I go in now?" Kai pouted.
"Sure, go ahead!" Leo said with a nod, then stood and watched, still recording as Kai got to the door and realised it was locked. "Oh yeah, I've got the keys!" he taunted.
"Leo, come on, before anyone else sees," Kai groaned, looking anxiously around at the neighbouring houses. The front gardens were quite large, but the dividers between them were mostly knee-high decorative walls or waist-high ornamental fences. Aside from the odd tree or large shrub, the area was mostly open and visible. Kai scowled as Leo walked deliberately slowly down the driveway before letting him into the house.
"Hey, where are you going?" Leo called out as Kai dashed for the stairs.
"To... dry off and get dressed," Kai said nervously.
"Nuh-uh," Leo said, shaking his head. "First we've got the issue of punishments to deal with!"
"For what?" Kai whined.
"When those people saw you," Caleb stated, "You covered up!"
"AND you ran!" Miles added. "So that's two punishments, right?" he asked, looking to Leo.
"Yup. Miles go grab the bag!" Leo requested, "We'll be in the lounge!"
Kai grumbled as he headed into the lounge, already scared of what the punishments would be. Unlike the dares, he had not written any of the punishments, so he had no idea what was in store. Once again, the fear had shrunk his boner back down, though it just meant his small dick was now more fully on show inside the wet boxer briefs.
Miles came storming down the stairs and threw the bag to Leo before jumping onto the sofa, eager to see what would happen.
"You wanna pick, or shall I?" Leo offered.
"You pick!" Kai pouted. Although he was sure his dare was over, he still didn't cover up for fear of giving them any more reason to punish him.
"Okay, your FIRST punishment," Leo said, emphasising the number to taunt his twin as he pulled out a piece of paper. He sniggered as he read it and said, "Nice!" Looking at Kai for a moment he said, "You have to post a picture of yourself wearing JUST underwear to your snap story!"
"Oooooh!" Miles cooed.
"Yussss!" Caleb hissed, clearly glad to see a punishment he had written come out.
"What? No, come on!" Kai whined, "I don't... want people seeing me!"
"Well they're gonna," Leo said mercilessly. "And y'know what, you look perfect like that!" he said, but as he saw Kai go to react he added, "Don't worry, we'll put an emoji over your junk!" He smirked at the others as he mumbled, "A SMALL one!" It got laughs from the two spectating boys. "Now smile!" he ordered as he held up his camera.
Kai whimpered, but took a deep breath and smiled, trying to at least look slightly confident as he stood all scrawny and wet and virtually naked. He heard a few clicks as Leo took several pictures, then watched as Caleb and Miles immediately gathered round to look at the results. They whispered to each other for a few moments before seemingly agreeing.
"Okay, I've sent you the one you need to post! Go get your phone and post it right away!" Leo ordered.
Kai huffed and headed upstairs to grab his phone. He opened the message from Leo and gulped slightly as he looked at the picture of himself. He really did look skinny and pale, his nipples erect and his cock just visible through the still-damp underwear. He put a smiley emoji over his cock. He considered making it a bit bigger to cover more of the area, but aside from knowing Leo would make him re-do it, a twisted part of him quite liked the idea of being exposed to all of his snap friends. He readied the post and took a deep breath before hitting send. He threw his phone down and headed back downstairs. Halfway down he heard a few notifications followed by laughter as the other three looked at the post.
"Fucking brilliant. Love it!" Caleb laughed.
"That's great," Miles grinned, looking over at the near-naked boy as he walked back in. He quickly turned his gaze away from Kai and back to Leo as he asked, "What's his second one?"
"Let's see," Leo said as he put his phone down and reached into the bag again. "Oh, looks like we got our first long-term one!" he said as he read it.
"Yes!" Miles declared excitedly. "Is it..." he started as he moved closer to Leo to look at the slip of paper, then repeated, "Yes!" as he read it.
"Guess we know who write this one," Leo sniggered. "So Kai, ya filthy little wanker," he said, giggling to himself at the choice of words, "For the rest of the summer, you're banned from wanking unless it's part of a dare!"
"What? No!" Kai gasped, then immediately blushed and said, "I mean... I... I don't... do that!"
"Oh please. EVERYONE does that!" Miles scoffed.
Caleb frowned a little as he shook his head and asked, "How do we even make sure he follows that?"
"I guess we just make sure he's supervised at all times," Leo said with a derisive grin.
Miles gasped and leaned in to whisper something to Leo, with Caleb leaning in to listen too.
"Oh, yes, love it!" Leo said happily, getting a nod of agreement from Caleb.
"What? What is it?" Kai asked anxiously.
"Wait and see!" Leo replied, eye wide in anticipation, "Now, how about we get onto your second dare!"
Thank you for reading, I hope you enjoyed. New chapters will post weekly, so be back same time next week for more!
If you have any questions or comments, my email is always open at matterotica@hotmail.co.uk. Alternatively, I can be found on patreon where I also post my stories, along with bonus content and exclusives, at patreon.com/matterotica
If you wish to read any of my other stories, please see below for links
The Kingswood Saga
Tales from Kingswood (Book 1)– https://new.nifty.org/stories/tales-from-kingswood-05107/
Half-Term at Kingswood (Book 1 bonus story) – https://new.nifty.org/stories/half-term-at-kingswood-02038/
The Kingswood Eight (Book 2) - https://new.nifty.org/stories/the-kingswood-eight-72284/
A Very Kingswood Easter (Book 2 bonus story) - https://new.nifty.org/stories/a-very-kingswood-easter-59761/
The Kingswood Effect (Book 3) - https://new.nifty.org/stories/the-kingswood-effect-64914/
Chris and Danny's Super Sexy Summer (Book 3 bonus story) - https://new.nifty.org/stories/chris-and-dannys-super-sexy-summer-98673/
The Kingswood Complication (Book 4) - https://new.nifty.org/stories/the-kingswood-complication-63298/
The Benny Saga (in reading order)
Benny Takes Control – https://new.nifty.org/stories/benny-takes-control-42615/
The Dangers of Desire – https://new.nifty.org/stories/the-dangers-of-desire-57149/
Benny's House – https://new.nifty.org/stories/bennys-house-65127/
Other Series
Possession – https://new.nifty.org/stories/possession-25306/
Phil's Naked Adventures – https://new.nifty.org/stories/phils-naked-adventures-02988/
The Humiliation Games - https://new.nifty.org/stories/the-humiliation-games-31885/
One-shots
The Art of Seduction – https://www.nifty.org/nifty/gay/adult-youth/the-art-of-seduction
Jake's Exposure – https://new.nifty.org/stories/jakes-exposure-73714/
Becoming an Internet Master – https://new.nifty.org/stories/becoming-an-internet-master-13630/
Brian's Big Mistake – https://new.nifty.org/stories/brians-big-mistake-31378/
And Then It Got Worse – https://new.nifty.org/stories/and-then-it-got-worse-05003/
Missed Opportunity – https://www.nifty.org/nifty/gay/young-friends/missed-opportunity
There's a Naked Alfie in the Garden - https://new.nifty.org/stories/theres-a-naked-alfie-in-the-garden-35531/