Daring Kai - Part 23 (Patreon)

Kai had been fishing for dares all week. Or challenges. Or forfeits. Or bets he could lose. Anything, it really didn’t matter what, so long as he ended up naked, embarrassed and, ideally, cumming excessively. And yet… nothing! The agreement had been made that the games would cease while the four of them weren’t together, and Miles had been away since the previous Sunday on his family holiday. He had hoped to tempt Caleb and Leo into teasing him, but he had realised pretty quickly that it just wasn’t happening!

Leo had been in a really bizarre mood. Considering how much he fought with Miles, it might have seemed like he would be positively cheerful with his annoying, ginger, living shadow on vacation, but it had caused the opposite – he was thoroughly dour from the moment Miles left. His mood was worsened even further by a constant feeling of exclusion from the other two members of the group, who seemed to take every chance they could get to be rid of him. He had continued to force his presence upon Kai and Caleb, unaware of their actual reason for wanting to be alone.

Caleb had been just as down as Leo, though his was driven by the recent loss of his grandmother, a loss he had chosen NOT to share with Leo and Miles. Kai hadn’t been sure why, but Caleb had always been exceptionally private and not very open about his feelings or anything going on in his life. It was likely the result of his unpleasant brother, unapproachable parents and general unhappiness at home, but they had never questioned it. His recent closeness with Kai had started breaking that down a little, but it was yet to spread to any more of his friends, so he just continued to shut Leo out, preferring to get any time alone with Kai he could get, which was mostly spent cuddling.

When Kai awoke that morning, he had been alone in bed once again. With Caleb staying over every night to steer clear of his brother, and Leo making himself ever-present, the three of them had slept in Kai’s room, though Caleb was on the spare bed and Leo on the camp bed. Kai had tried rather unsubtly to hint at a return to his nighttime restraints and butt plug, but Leo frustratingly never seemed to catch on. When the other two awoke, they had dourly discussed the day ahead, with both Leo and Caleb suggesting they skip football practice as they weren’t in the mood.

Kai was having none of it. “No, you need to go, practice is important!” he had started with, followed up by, “It’ll be good to actually get out and do something!” With the other two not quite convinced, he had concluded his persuasion with, “You know how important you both are to the team. They’d really struggle without you!” Kai actually had no idea how important they were, as he paid virtually no attention to the games he had started cheerleading for. He also didn’t really care about the importance of practice. Kai’s mind was on one thing only… a dare in the team shower afterwards!

The previous week, he had been dared to ‘use’ a dildo, which he had… on Oz, one of Leo’s hunky teammates. Fucking the bigger teen with the toy had been thrilling, and something that played on Kai’s mind all week, featuring frequently in his wank fantasies… not that he was actually allowed to wank! He was sticking to his ‘no cumming outside of dares’ rule, so those fantasies always ended up in frustration. He hoped a new dare from the team might get him the embarrassment he craved and the orgasm he needed.

The atmosphere at the pitch was quite different from the previous week. While match days saw a significant number of friends and family coming to observe both teams, practice days weren’t really observed, and with Miles away Kai was sitting alone as he watched the team running drills at their coach’s command. With no crowd to cheerlead, Kai was dressed in his normal clothes, which felt strange as he was so used to wearing his cute and revealing cheerleader outfit around the team.

Throughout practice, Kai received a lot of looks from various members of the team – meek smiles from Caleb, annoyed glares from Leo (because of the smiles from Caleb), strange stares from Oz and more than a few furtive glances from other members of the team. His first shower dare – a straightforward wank – had amused the team but not caused much more of a visible reaction than that. His second dare – the Oz/dildo incident – had caused a fairly substantial number of unwanted, embarrassing and probably confusing erections for the other boys. As Kai saw team members looking his way, he couldn’t help imagining how many of them had thought about him while wanking over the last week.

With the practice session seemingly going on forever, Kai eventually looked up from his phone as he needed to pee. He wandered off towards the toilets, situated around the rear of the shower block but came to an abrupt halt as he turned the final corner. There they were, two boys from the football team… kissing! They saw Kai just a few moments after he saw them and quickly jumped apart looking both terrified and guilty.

Kai smiled as he looked the two boys up and down briefly. Neither of them went to his school, but he was gradually picking up the names of the ones he didn’t already know. The first was called Mark, a tall slim sixteen-year-old whose arms and legs looked positively scrawny as they protruded from his football kit. His short blonde hair looked to have been fairly neatly styled before the rigors of practice messed it up, while his pale blue eyes, normally quite soft and soulful were suddenly filled with dread.

The other was called Sam, a boy who looked more like he belonged on a rugby team than a football team, standing a little short for his age but broad even compared to someone of average height. His weight was carried all over, just looking generally ‘big’ rather than sporting a belly. Like Kai, he was on the verge of turning sixteen, and like Mark, he looked absolutely terrified about being caught.

Both boys suddenly burst into pleading at the same time. “Please don’t tell anyone. Please. You can’t. Please!” Mark pleaded while Sam begged, “I can’t get outed now, please, I’m not ready for that, please it wasn’t what it looked like!”

“Woah woah woah, hold up!” Kai silenced them, raising his hands as he shook his head. As the two anxious teens fell silent, he smiled sweetly at them and said, “I’m not telling anyone anything. There’s nothing to tell. I didn’t see anything!”

“Seriously?” Mark asked, panting slightly.

Kai smiled and offered an emphatic nod.  “I’ll keep quiet… for a price,” Kai joked playfully. As he saw both boys looked terrified again, he laughed and said, “I’m kidding, I’m kidding. No price, I swear!”

“Ya little fucker!” Mark sighed.

“Shame,” Sam added, “Coulda been a fun price!” He winked flirtatiously at Kai.

“Oy!” Mark immediately objected.

“Oh!” Kai said with a grin and a knowing head bob as he looked at the two teens. “So this wasn’t, like… a first kiss. Are you only meant to be winking at him?” he asked playfully, looking at Sam as he nodded to Mark.

Sam and Mark exchanged anxious looks before they both shrugged and Mark replied, “Yeah, he’s… we’re… I’m…”

“He’s my boyfriend!” Sam said, not even attempting to conceal the glee on his face.

Mark stared round at Sam wistfully and said quietly, “I’ve never heard you say that out loud before!”

Sam looked a little choked up as he stared back, then leaned in slightly before he paused and they both looked at Kai.

“Oh, don’t mind me! I can cheerlead if it helps!” Kai offered cheekily, “And I gotta say, seeing you having to lean over to kiss the little shortie… fucking adorable!”

As Sam laughed, Mark rolled his eyes and huffed, “Don’t you start. It’s bad enough when HE does it. He keeps saying I need to carry a stepladder round to save his neck!”

Kai chuckled and replied, “Cute, but yeah, I’ll leave you to it!” As he headed past the two boys, he added a playful, “Have fun!” As he reached the door to the toilets, he stopped and glanced back. Sam and Mark were kissing and while Kai had expected the sight of it to make his cock throb. He did feel something, but it emanated from a little higher up. He felt a dull ache in his chest as he watched them briefly before he sighed wistfully and continued inside.

*****

The rest of practice was mostly uneventful. Kai enjoyed watching, as he kept looking for Sam and Mark. Now that he knew they were together, the longing looks and glances they shot each other, the fleeting touches, the chemistry, it all seemed so obvious. Kai was just surprised he hadn’t noticed it before and wondered what other things were right in front of him that he hadn’t noticed.

Lost in thought, Kai didn’t even noticed Caleb until he was right in front of him! “Oh, you finished?” he asked, blushing slightly.

“Yeah, just give us a few minutes to get changed and we’ll be good to go!” Caleb said with a nod.

“So it’s shower time!” Kai said happily as he stood up, grinning excitedly.

“Nah, we don’t usually bother showering here after practice. We don’t usually get as muddy!” Caleb explained, gesturing down at himself.

Kai looked the other boy up and down and let out a gentle whimper as he realised he looked sweaty (and sexy) but substantially cleaner than he usually did at the end of a match. “No showers?” he whined, “But that’s all I came for!”

“And here I was thinking you actually wanted to support me and Leo,” Caleb smirked, “Sit tight, we won’t be long!”

Kai pouted as Caleb ran off towards the locker room, but it quickly changed to a nervous stare as he saw Oz hang back and begin approaching him. “Umm… hi… Oz,” he said nervously. He hadn’t spoken to Oz after the incident in the shower the previous week and so far he was unsure exactly how annoyed he was about having the dare turned back on him, so he could feel his anxiety growing as the looming figure approached.

“You!” Oz said with his brow heavily furrowed, “I need to talk to you!”

Kai let out a noise that had been an attempt at actual words, but became an incoherent, nervous grunt.

Oz surged forward and grabbed Kai… and hugged him so tightly he actually lifted him off the ground. “Thank you!” he said as he squeezed Kai tightly.

Kai wheezed slightly from the vice-like grip, then took a deep breath as Oz put him down and repeated curiously, “Thank you?” He gulped a little and asked, “For what?”

“For that shit with the dildo. Fuck me!” Oz exclaimed, shaking his head. He grinned as he realised his accidental pun and chuckled, “Ha, fuck me, that’s good!”

“You… you… you liked it?” Kai asked, suddenly feeling a surge of excitement. Oz liked the dildo. Oz liked butt stuff. Oz liked HIM for doing butt stuff on him. Oz was hot. Oz was hot and into butt stuff and grateful to him. Oz had lips. Lips are used for kissing. Kai wanted to try kissing. Maybe Oz would kiss him. Maybe Oz was in love with him because he did butt stuff on him and now he wanted to kiss. It ran through Kai’s mind in a heady blur of expectation and hope and anticipation.

“Oh my god, yes!” Oz nodded emphatically. “And cos I knew some of the guys just can’t keep their mouths shut about ANYTHING, I figured I’d tell my girlfriend before any of them did and she thought it sounded hot and… she did it to me. Like… she just… went with it and did it to me, and… oh my fucking god. Seriously! Best sex we’ve ever had!”

“You… your… your girlfriend…” Kai stuttered, feeling his momentary hope melt away. Not wanting to give himself away, he forced a smile and asked, “What, so she just… dildo-fucked you and… it was good?”

“Good? Mate, it blew my fucking mind…” Oz exclaimed, then blushed slightly as he added, “And my load. Oh, hey, you won’t… tell anyone any of this, right?”

“Of course,” Kai nodded.

“Good, cos she didn’t just use a dildo on me, she… she used…” Oz paused, looking round to make sure nobody had appeared nearby to eavesdrop, then lowered his voice and continued, “She used a strap-on and, like… FUCKED me with it. I think they call it pegging!”

Kai’s disappointment had vanished as quickly as his hope had appeared as he listened to Oz. Instead, he felt a rush to his cock which chubbed up in an instant. Squirming a little at the thought of Oz getting fucked (even by a girl), he attempted to adjust his swollen cock subtly but only drew more attention to it.

“Oh, ya like that do ya?” Oz sniggered.

“No, well… yeah, kinda, but… I’m just…” Kai stammered, then let out a groan and admitted, “I’m just REALLY fucking horny and I thought I might get another dare in the showers today but Caleb said you guys don’t shower after practice, and…”

“Say no more. Come with me!” Oz said as he placed his hand on Kai’s back to lead him towards the shower block.

“Wh… what are we…” Kai started nervously, but as he got a wicked grin back from Oz he just gulped, nodded and went along with him.

“Hey guys,” Oz called out as he entered the locker room, causing a sudden lull in the racket that had been filling the large room. “Our lil cheerleader’s already thinking about his next dare after our next match and I had an idea!”

“What are you doing?” Kai asked quietly. Just having everyone looking at him, even fully dressed and just standing there, somehow felt exposing and embarrassing.

“I think we should play a game to decide who gets to give him a dare next week! Who’s in?” Oz asked, receiving an immediate cheer as the rest of the team began to gather.

Kai gulped, but managed a meek smile as he saw Leo and Caleb both looking amused by the whole thing.

“What’s the game?” Sam asked, clearly trying not to sound too interested as he shyly avoided eye contact with Kai.

Mark was standing close to him, though Kai smirked a little as he noticed the deliberate distance they kept so as not to appear ‘too’ close.

Oz started, “Well it seems cheerleader boy…”

“Cheerleader boy has a name!” Kai snapped a little bluntly, getting a chorus of ‘oohs’ and laughter from the rest of the team.

“Fine, then it seems Kai…” Oz started, then looked to the smaller boy and asked, “Happy now?” As he got a nod back and titters from the group, he continued, “…is a horny little bitch. See!” He suddenly reached out and yanked down Kai’s shorts and underwear in a single gesture.

“Hey, what are you…” Kai started, but he was cut off by Oz grabbing his t-shirt and pulling it off over his head. Suddenly naked, he feebly attempted to conceal his erection as the team cheered and hollered for their nude cheerleader.

“See, like I said… horny little bitch,” Oz sniggered as he tossed the t-shirt aside. “So, we’re gonna play Russian roulette, and Kai’s playing the part of the gun!”

“Oh, I know where this is going!” Caleb whispered to Leo and got a wicked giggle in response.

“Gather round, lads,” Oz said casually. “Ya gotta jerk him off for 5 seconds. He cums and YOU get to give him his dare next week!”

“Eww, I don’t wanna touch that!” Mark groaned, getting a few murmurs of agreement.

“THAT!?” Kai snapped back at them grumpily.

“Hey, look, none of us WANT to be touching it,” Oz interjected, “But if you want the chance to give cheerleader boy a dare… and believe me, he will do WHATEVER you dare him, right?”

“Umm… so long as it doesn’t get me arrested I suppose!” Kai said, blushing as he felt his cock throbbing at the prospect.

“Oh, you mean like playing strip high five in Market Square!” one of the boys called out.

“That was you!” Zack Smith exclaimed.

“Oh my god, I was there!” “I heard about that from a friend!” “Did he really get naked?” “I heard he wanked off right there!” “I wouldn’t have the balls!” “He’s such a show-off!” “Did he actually get arrested?” “He’s cute when he blushes!”

“Okay, okay, okay,” Oz said, gesturing for quiet. “Probably safe to say it WAS Kai, cos let’s face it… who else is fucking daft enough to do something like that!”

“It was, and you’re right!” Leo called out, getting more laughs and comments about the very public incident.

“Great, talk about that later. For now… we got a game to play!” Oz insisted.

“Do I get any say in this?” Kai asked feebly.

“No,” Oz replied curtly, “And take them off!” He pointed down to Kai’s shorts and underwear around his ankles.

“Fine,” Kai huffed as he kicked the clothing aside.

“Great, now form a circle,” Oz instructed, keen to get the game going as he continued, “And I’m going first!” He reached down and grabbed Kai’s dick, pumping away rapidly.

The team counted the five-count aloud before Kai was unceremoniously shoved towards the next person in the circle.

“Fuck,” Kai grunted as he felt himself getting wanked off by the second person in less than a minute. Oz was right, he had been ready to blow. Between the prolonged abstinence, seeing Sam and Mark make out, hearing about Oz’s pegging and the sudden strip in front of the team, he was already on the verge of orgasm as he moved onto hand number three.

A quick five count later he had moved on again, this time to a more familiar hand as Caleb cautiously masturbated him, blushing heavily as he did it. As Kai felt himself close to release, he heard a sudden wave of jeers, taunts and laughs as he realised he was about to get wanked off in front of more than a dozen guys… by his own brother!

“That’s sick!” “Weirdly hot!” “That’s his twin!” “They don’t even look alike!” “They’ve SO done that before!” “So weird!” “He’s gonna blow!”

Kai was mere moments away from ejaculating as Leo quickly shoved him away. The moment he felt the next hand grab his cock, that was it. Letting out a shuddery gasp, he yelped, “I’M CUMMING!”

The boy holding his cock – a boy named Tyler Everett he knew from school by name only – suddenly let go and turned Kai away to make sure he didn’t get hit with the imminent spurts.

Staggering to the middle of the circle, Kai stood and ejaculated as the boys hooted, hollered, cheered and laughed at him.

“He’s definitely got balls… and they work!” “How can he just stand there like that!” “Tyler wins!” “Tyler loses!” “Kinda hot!” “It was totally Leo that made him do it!” “I never got a turn… which… is good. Shut up!” The comments swirled around once again as Kai sprayed the floor with his spunk, his raging erection twitching and bobbing wildly.

“Well there we go. Ty, get thinking about what you want him to do next week. Remember, anything goes!” Oz explained.

“ALMOST anything!” Kai quickly interjected.

“Oh yeah, he’ll be ‘thinking about it’ all week,” Sam teased, giving a wanking gesture.

“Fuck you!” Tyler snapped back at the other boy.

“Is that the dare?” Oz called out, getting more laughs as the boys dispersed, seemingly disinterested in Kai who still stood naked in the middle of the room.

“Guess I’ll… get dressed then,” Kai said, embarrassed at the indifference the boys seemed to have towards his nudity. He grabbed his t-shirt from the bench where Oz had tossed it and pulled it on as some of the boys started rushing out of the locker room, shouting brief goodbyes. Walking over to where he had kicked his shorts and underwear, he frowned slightly as he saw only his shorts. “Anyone seen my pants?” he called out, and immediately regretted his choice of words as it got laughter from the remaining boys, more of whom were disappearing.

“Hnnh, ended up in the same place as that dildo, I guess!” Oz said with a shrug as he shoved his clothes into his bag, seemingly heading home in his kit.

“Where’s that?” Kai asked curiously.

“Fuck knows,” Oz replied with a shrug, “Just kinda disappeared!”

Kai gulped at the thought of someone taking his underwear. It was a little annoying, as it was a pair he liked, but at the same time… it was a little exciting too. Pulling on his shorts, he glanced over at the door and made brief eye contact with Tyler who was just on his way out.

“See ya next week, Kai!” Tyler said with a slightly shy smile, getting sniggers from the few boys left in the locker room.

“Yeah, can’t wait,” Kai replied with a shameless grin.