Daring Kai - Part 22 (Patreon)

Kai had been understandably nervous as he made his way to the football pitch. The last time he had been there, he had been cheerleading as part of a dare, and had spent the second half of the match with a vibrating butt plug inside him for the very first time. Being forced into the situation and humiliated by his own constant arousal, it had been absolutely mortifying. To make matters worse, he had been accosted by a group of thugs after the match before being saved by his brother.

Today had been a very different experience. The thugs were nowhere to be seen, as the team they supported weren’t playing, so Kai had immediately felt safer. He wasn’t technically doing the cheerleading under duress either, which somehow made it both more and less embarrassing at the same time. Most of all though, he had been… popular!

Leo and Caleb’s team had already made Kai feel welcome, through a playful humiliation in the showers after their last match, and Kai’s willingness to join in and play along had endeared him to the entire team right away. They were thrilled to have him back to cheer for them at another match. The spectators made him feel just as welcome. Word of his antics had spread to some of the other friends and families of the team’s players and they had all gathered a little closer together than usual when they saw he was back again, ready to follow his cheers.

It had been rather embarrassing at first, as Kai really wasn’t a great cheerleader, though he was learning quickly what got the crowd going and what could get laughs or cheers. Today, he had been joined by two young children, seemingly the younger siblings of one of Leo’s teammates. Kai had happily let the little boy and girl join in, giving each of them a pom-pom before attempting (and failing) to get them in sync with him. By the end of the match, the audience were in hysterics at their antics, though they were very much laughing with Kai rather than at him, which certainly made a nice change.

“No, it’s okay, you can keep them,” Kai said at the conclusion of the match when the two children went to hand the pom-poms back.

“Oh, you have no idea how much you’ve just made their day!” the kids’ mum said with a grateful smile to Kai. She looked to the two kids and said, “Say thank you!”

“Thank yoooou!” the two children said, beaming with absolute glee as they waved their new toys.

Kai laughed as he waved the kids off, heading over towards the shower block where the team was just starting to head.

“Think they’ve got anything planned for you in there?” Miles asked curiously as he left the small crowd and tagged along with Kai.

“Don’t really know,” Kai answered honestly.

“But you hope they do?” Miles enquired, though it was mostly rhetorical.

Kai just laughed at the question and chatted with Miles a little longer until he caught up to the team who cheered at his approach. “Wow, a guy could get used to this!” Kai said cheerfully.

“Have fun,” Miles smirked as he lingered back to let Kai follow the team inside.

“Come on, cheerleader boy,” one of Leo’s teammates said cheerfully, as they headed to the locker room.

As always, it was the smell that hit Kai first as he walked in, a mixture of mud, teenage sweat, steam and cheap body spray, an odour thoroughly distinct in its ability to fall into both ends of the pleasantness scale. Kai recoiled at it slightly, but felt a twitch in his cock at the same time. He didn’t really have much time to consider his feelings on the smell as he found himself looking at the team already starting to remove clothing.

“KAI, OVER HERE!” Oz bellowed across the loud chatter filling the locker room.

The shout caused a slight lull in the noise as Kai headed over towards Oz. He felt like he should be more nervous than he was, but the team had already made him feel welcome both days he had been at their matches, so his fear was more of what was to come than who he was with. “Hey Oz,” Kai said with a meek smile. He briefly glanced off to one side where Caleb and Leo were both watching. Both looked amused and intrigued, which never boded well.

“We got your next dare for ya, dare boy!” Oz said, clearly speaking primarily to Kai, but with his voice raised enough to ensure it carried across the locker room.

Kai smirked a little. First cheerleader boy and now dare boy. These football players may have been fun, but original thinkers they certainly were not! “And what makes you think I’ll do it? Just cos you say it’s a dare?” Kai asked, knowing he would absolutely do whatever they dared, but still wanting to give them a bit of a challenge.

“Cos you’re dare boy, and you’re already getting a boner for it!” Oz said, causing a wave of laughs and jeers from the team as Kai began to blush, glancing down at the bulge in his shorts.

“Fine, what is it?” Kai demanded, slightly annoyed that his own teasing hadn’t paid off.

“You’re gonna join us in the showers again,” Oz instructed, “But this time when you go in there, you’re gonna find a… new toy!”

Oz’s comment got mixed reactions from the team, with some laughing sinisterly, seemingly in on the dare, while others simply exchanged looks as confused as Kai’s.

“Your dare’s pretty simple. You’re gonna use the toy… til ya jizz!” Oz said, this time getting unanimous amused reactions from the rather blunt choice of words.

Kai gulped slightly. Cumming in front of the team was nothing new, but still a thrilling mix of exciting and intimidating, but throwing in the unknown toy… it could be anything! They might even mean a regular toy, rather than a sex toy, it was hard to know with these guys as they all talked the talk when it came to sexual boasting, but how much was actual experience and how much was bravado and bluster!?

“No need to wait for us,” Oz said as he squatted down to start unlacing his football boots.

Kai quickly began to strip, avoiding looking round for fear that he might see something that turned his semi into a full-on erection. Just walking to the showers naked and without a towel felt exposing enough, he didn’t fancy doing it with a boner bobbing around ahead of him. Thankfully, anxiousness was his friend for once and by the time he was naked, his cock had softened.

He shot his brother and Caleb a nervous look, getting a supportive smile back from each of them. He hurried over to the door to the shower area and stepped inside to see something small yet somehow prominent on the ground in the centre of the area – a dildo! “Oh fuck!” Kai grunted quietly to himself, then sniggered at the unintentional appropriateness of the word.

Kai walking in seemed to have been the trigger point for the rest of the team to follow as they started filing in behind him.

“Dildo!” “He’s gotta use that?” “Hey, it’s bigger than you!” “I think I know him!” “What’s that?” The comments from the team were mildly amusing to Kai, though he barely had the mental capacity to register them. So far, he had put two things up his butt – a carrot and a small butt plug. The dildo sitting before him was, thankfully, not huge. It was certainly bigger than the plug, and while he winced slightly at the thought of pushing it inside him, he didn’t hate the idea… although he certainly would have preferred to explore it without such a rowdy audience.

“Damn, he’s gonna use that thing!” “Is he gonna sit on it?” “That’s pretty big. It’s big, right!” “You gonna watch your own brother do that shit!”

The comment caught Kai’s attention as he realised who was coming in and looked round to see Leo, who was grinning broadly as he replied, “Yeah, but only so I can tease him about it, like… forever!” It got laughs from the boys around him as they spread out to start using the showers.

Kai failed to suppress a smile. Leo threatening to tease him about the dildo was sweet, because despite all of the dares so far, the actual teasing from his twin had been virtually non-existent – yet another example of Leo’s tendency to sound a lot meaner than he ever really was.

“Think about how he worded the dare,” Caleb suddenly whispered as he moved behind Kai, “What would Miles do?” He gave Kai a playful wink before continuing on to claim a shower head.

“Come on then dildo boy,” Oz said as he walked in proudly, towel slung over his shoulder.

Kai rolled his eyes slightly. Dildo boy? They really needed a new writer! “Okay, okay,” Kai said as he approached the centre of the room and reached down to pick up the dildo. It was a light beige, likely intended to be Caucasian-skin coloured, though Kai couldn’t think of anyone who was actually such a weird shade. It stood at about six inches long and was thankfully not too thick, as his fingers easily met as he gripped the base of it. It felt slimy to the touch, as it had apparently been pre-lubricated, which was strangely considerate of the team. He stared at it for a few seconds as the comments around him swirled once again.

“He looks scared!” “He looks horny!” “He looks cute? What? He does!” “Which end’s it going in?” “You think he’s used to bigger?” “He doesn’t have pubes. Did he have them last time?” “He’s so not gonna do it!”

Kai took a breath, steeling himself to try and insert the toy until he glanced over and saw Caleb. ‘What would Miles do?’ That was his advice. Miles was sneaky, always finding loopholes and work-arounds… like the masturbating dare where he had not exposed himself… because the dare hadn’t told him to! That was it! ‘You’re gonna use the toy until you jizz!’ That was his dare, exactly how it had been worded. Use the toy! Not ride it, insert it, fuck himself with it or anything that REQUIRED insertion, just… USE it!

Ideas began to form for how Kai could save himself. The dare didn’t even say he had to cum now, in front of the team, so he could likely weasel his way out of that part too… but he didn’t want to! But turning the rest of it around would be a fun way to mess with the team… and Oz. Kai’s eyes widened as he contemplated the ringleader and in that moment, the mess of ideas crystalised into a final plan. “I gotta use this dildo til I cum, right?” Kai called out, blushing slightly at the mention of making himself cum.

The team cheered.

Kai approached Oz as the team quietened and watched intently. “Okay then, I’m gonna do your dare,” he said, getting another cheer. Grinning at the figure towering over him, he cleared his throat and said loudly, “I’m gonna use the dildo like you told me to… and I’m gonna use it… on Oz!”

“What? No!” Oz suddenly gasped as the crowd burst into laughs and cheers. Oz took a step back from the small, dildo-wielding boy, but instantly he had teammates grabbing at him to bring him forward. “This isn’t… this isn’t what we…”

“NUH!” Leo cut his teammate off. “This is what you gotta learn,” he said over the excited murmuring of the team, “Make your dares clear otherwise… stuff happens!” As he got a red-faced scowl from Oz, he challenged him, “So you gonna let him do his dare, or you backing out of it, cos… well, I reckon the team wouldn’t be happy with that, would ya?”

“No!” “No way!” “Do it!” “You gotta!” “Dildo boy beats dildo man!”

As annoyed as Oz looked, he also looked slightly amused and almost… proud of the way Kai had beaten him. With a huff and an eyeroll, he called out, “Fine, just fuckin’ do it, okay!” The crowd went wild, backing away now that they no longer felt the need to restrain Oz, though they remained in a tight group around them, rather than returning to their individual shower heads.

“Well, turn round and grab your ankles then,” Kai said, waving the dildo as his own cock stood erect. Amazingly, nobody even seemed to care about how aroused he was, their focus was on the imminent dildo insertion.

“I will SO get ya back for this,” Oz said, sounding only partially sincere. As he turned and bent over, it got another wave of mixed reactions.

“Eww, it winked at me!” “Damn, that’s a hairy butt!” “Does yours look like that?” “How the fuck would I know?” “Dildo boy, ha!” “Shove it in!” “Weirdly hot!”

Kai gulped as he aimed the toy for the hole. He pressed the tip against it and circled it gently. He wanted to tell Oz to relax, but wasn’t sure if it would embarrass Oz or himself more. His own cock positively throbbed. He wanted to grab it with his free hand, but worried he might cum quickly and that would end the dare, freeing Oz, so he held back. After teasing the hole for a few moments, he pressed it into the centre and felt a little bit of give.

The spectating crowd began to move slightly, as more of them moved around to stand behind Kai or to the sides to watch the toy being pushed in, while a few remained the other side, either insisting they didn’t need to see it, or hoping to get a look at Oz’s reaction as it slid in.

Kai continued to push gently and watched in delight as the ring opened slightly to allow the slippery toy to start sliding inside.

“Oh my god,” Oz gasped, visibly trembling as the toy impaled him, getting laughs and shrieks and in response from his teammates.

Kai pulled the toy back out, not wanting to push too hard, too quickly, but also because he liked the sight of the ring allowing it to push its way in. Glancing round, he saw a lot of hands awkwardly positioned to hide crotches. In a way it was frustrating as it spoiled his view of the team’s dicks, but at the same time it was thrilling to know it was likely because they were becoming at least a little aroused. His own prick ached to be touched.

Feeling the toy pushed back in, Oz gasped once again and straightened up slightly, but let out a shocked gasp as the change in position allowed the dildo to hit a different spot this time. “Jesus… fuck!” Oz gasped, feeling his legs wobbling a little.

“I found it,” Kai giggled quietly to himself. The comment was overheard by few and understood by even less. Excited to be getting such a reaction from the large, bulky teen, he pulled the dildo back and then slid in again, deliberately poking at his prostate.

After a few slides in and out, accompanied by tight-lipped whimpers, Oz shook his head and looked back at Kai.

“Need me to stop?” Kai asked anxiously as he saw Oz look.

“No, I just… one sec,” Oz replied as Kai pulled the toy out. He dropped down to his knees, his face bright red as the laughs and jeers from the visibly-aroused team echoed loudly around them. He leaned forward onto all-fours and gave Kai a nod to continue.

Kneeling down too, Kai pushed the toy into the ample rump once again, trying a few angles until he found the sweet spot for the new position and began pumping the toy faster.

“Oh my fucking god,” Oz gasped as he felt the smaller boy fucking him with the dildo, either ignoring or utterly oblivious to the team crowding around them. “Fuck, fuck, fuck, fuck,” Oz grunted as he crossed his forearms on the ground and rested his head on them.

“Jesus, he’s in agony!” one of the team commented, looking visibly concerned.

“Yeah, mate,” Zack Smith commented, shaking his head, “Believe me, that’s not pain!”

Kai looked at the boy from his school and smirked as he nodded his agreement. Casting his gaze down the boy’s naked body, he smiled at the thoroughly unsubtle boner concealment his hands were providing and as his gaze roamed back up to Zack’s face, the embarrassed teen immediately looked away. “Zack’s right. I reckon he’s gonna blow!” Kai called out, then shoved the dildo in hard as he asked teasingly, “Right, dildo man?”

“Fuck,” Oz gasped as he suddenly shot up, kneeling bolt upright to reveal his rock-hard erection which he immediately wrapped his fingers around. Three strokes was all it took and he started squirting his load onto the ground in front of him. He wasn’t getting particularly good distance, but based on the noises he was making, the look on his face and the sheer quantity of spurts he produced, it was clearly a wondrously intense orgasm.

“He’s cumming!” “That’s gay!” “That’s homophobic!” “He’s fucking loving it!” “Looks kinda fun!” “He’s actually cumming!” “Damn, cheerleader boy’s good!” “Shut up, I don’t have a boner, YOU have a boner!”

Looking around the orgasming football player, Kai finally reached his limit and grabbed his own cock with his other hand, keeping the dildo inserted into Oz, but motionless. He masturbated rapidly, barely even noticing the team looming over him. Just as he began to near orgasm, he began to register the comments and jeers once again, but it only pushed him towards a more excited release as he aimed his cock at Oz and plastered his back with spunk.

The crowd went absolutely wild at seeing their cheerleader cumming on Oz, who simply looked too shellshocked to even react to it.

And then… it was over! As if the second orgasm had been some kind of off-switch for the team’s enthusiasm, they began to disperse. Realistically, it was more that they all began to worry that their own erections may begin to draw attention now that the main show was over, but the group collectively did a great job of feigning disinterest as they headed back to resume showering.

Kai pulled the dildo out with a slight slurping sound, then presented it to Oz as he said, “I’m guessing you’ll be wanting to keep this!”

“No, I’m good,” Oz replied, red-faced from the embarrassment as much as the exertion of what he had just been through.

“That was fun!” Kai grinned.

“Yeah,” Oz replied, still looking slightly shaken. He glanced at the toy and said, “Just… leave it there!”

“Okay,” Kai said as he placed the toy down and got up to go and shower.

Once Oz was back on his feet and showering again, the teasing began, but Oz was quickly back to his usual self and retorting with amusement and ferocity, seeming largely unbothered by the jokes at his expense.

As the team began to finish showering and head back into the locker room to get dressed, Kai followed. As he headed for the door, he bumped slightly into Zack and shot him a sincere smile, but he didn’t get one in return as Zack hurriedly scurried away, though not before giving the towel-less Kai a quick look up and down.

*****

“We should totally put another dare in the bag!” Miles insisted. He was sitting on Leo’s bed, while Leo sat on the floor and Kai was casually spinning on Leo’s desk chair. Caleb had headed off after the match for a family thing, so any formal dares had been put on hold until he was back.

Leo tutted and rolled his eyes as he replied, “No, we shouldn’t! I know it was technically a dare he did in the showers, but it wasn’t one of OUR dares and it wasn’t part of the game!”

“He did a dare. We should add another! The rules said when he does a dare, we add another to the bag!” Miles said firmly.

“It wasn’t part of OUR game!” Leo huffed.

“It’s a chance to give him ANOTHER dare. Why you fucking bitching about it?” Miles demanded.

“Ugh, the game’s never fucking ending anyway. Even without you being away for your stupid holiday, the bag’s still full and every time we do one, we add one so they’re never going down!” Leo said grumpily.

“Speaking of going down…” Kai interjected, winking at Miles.

“Meh, later, I’m not in the mood!” Miles replied casually, then frowned at Leo and added, “And our holiday isn’t stupid. I can’t wait!”

Leo tutted and rolled his eyes again.

“What?” Miles demanded, “What now?”

“Nothing,” Leo snapped, looking very clearly like it wasn’t nothing.

“It’s just part of the fucking game. If you’re that bothered, you know he can do you too!” Miles said, smirking slightly as he looked back and forth between the twins.

“Eww, I don’t want him touching my dick!” Leo replied sharply, but winced a little as he saw the sad look on Kai’s face. They hadn’t done anything together since jerking each other off, and not even spoken about it, so for that to be the first thing he said about the encounter seemingly upset his brother a little. “I mean any guy, not Kai specifically! I don’t want a guy touching my dick!” Leo corrected himself defensively.

“You know what, if you two are just gonna be bitching at each other again, I’m outta here,” Kai said, mostly upset about Leo’s comment, though being around the squabbling pair wasn’t exactly appealing anyway. He stood up and staggered slightly, dizzy from his spinning on the chair. “I meant to do that!” he said as he bumped into the doorframe and heard laughter from behind him. Before he even had the door fully shut the other two had resumed arguing.

Kai glanced at the door to his room but didn’t really fancy sitting alone as he had little to do, so he wandered downstairs to see what his parents were up to. His dad was in the kitchen doing some baking – an attempt to recreate something he had seen on a TV show – while his mum was outside doing some gardening in the back garden. He stood chatting to his dad for a while before going out to talk to his mum. When he heard the doorbell chime, he felt his heart pound.

A couple of weeks ago he had been given a dare to answer the door naked (and hard, and masturbating, and ask if they wanted to see him cum!!) His own suggestion had been for him to do it five times! He had done it twice that day, but since then it had only cum up twice more. The first of the two, he had exposed himself to a pizza delivery guy who laughed at his offer and walked away. The second, he had ended up cumming for the enjoyment of a delivery man who looked like he wanted to do more than just watch. It still left one more time he had to do it, but it was risky with his parents around.

“Kai, can you get that, I’m covered in icing!” Mr Robinson called out.

“Fuck,” Kai muttered under his breath, feeling his cock swell almost instantly. He rushed back inside, through the kitchen and out into the hallway. Thankfully he had the wherewithal to at least shut the kitchen door. The doorbell rang again as he started pulling his clothes off. He finally reached the door, naked and hard, and pulled it open.

“Oh!” the young man standing on the other side of the door exclaimed as he saw Kai standing there fully exposed with his hand on his dick. He looked to be barely out of his teens, dressed in a shirt and trousers with a hi-vis vest over it bearing a company logo, with a tablet gripped in one hand. He had a name tag beneath the logo that identified him as Jamie.

“Would you… like to see me cum?” Kai asked, gulping heavily.

“Umm… no thank you,” Jamie replied. Then something unexpected happened – he didn’t move!

So far, all four of Kai’s observers had either accepted the offer and watched the show, or basically run off in shock and disgust. Jamie did neither, though the nude teen did throw him off a little it seemed.

“I, umm… I’m here to ask about your… your internet provider,” Jamie said a little shakily, “Do you… know who you’re currently with?”

“Umm… Virgin!” Kai replied, then immediately blushed as he said, “I mean… umm… that’s who we’re with, I wasn’t… calling you one, not that I’d know if you are, umm… you might be. Umm… I’m not, but… but there’s nothing wrong with… with being one!”

“O… okay,” Jamie stuttered, clearly every bit as embarrassed as Kai.

“And do you know how much you pay for that?” Jamie asked, very visibly working hard to keep his gaze fixed on the naked teen’s face.

“I… I don’t,” Kai replied.

“KAI, WHO IS IT?” Mr Robinson called out from the kitchen.

Kai looked terrified, suddenly reminded of the risk of his situation. “Oh, I’m sorry, I think… we’re happy with who we’re with!”

Jamie nodded and started, “Umm, it’s just… we’re in the area today offering…”

“Oh my god, what are you doing?” a voice suddenly called from behind Jamie. As Kai looked past him he saw Caleb approaching. “What are you doing with that naked child?” he asked firmly but (thankfully) quietly.

“I… I was… I…” Jamie stuttered, looking absolutely mortified, “I’m sorry!” he said and ran off down the driveway.

Caleb snorted with laughter as he watched Jamie run.

“Well, that’s him scarred for life!” Kai sniggered, then remembered once again his situation and called out to his dad, “IT’S ONLY CALEB!”

“Only!?” Caleb muttered as he walked in, “Rude!”

“Hnnh, sorry,” Kai laughed as he shut the door.

“HI CALEB!” Mr Robinson shouted.

“HI MISTER R!” Caleb shouted back.

Kai quickly gathered his clothes and started up the stairs as he called out, “GOING UPSTAIRS, SEE YOU LATER!” Glad to have finished the dare without getting caught, Kai squealed as he felt Caleb slap his bare, naked butt as he ran behind him. They hurried into Kai’s room where Kai threw his clothes down onto the bed. “Thanks for saving me,” he said with a chuckle as he looked round at Caleb who had shut the door and now stood motionless behind it.

Caleb said nothing and did nothing, looking almost frozen.

“Cay?” Kai asked curiously as he took a step closer, “You alright?” He saw Caleb gulp but still not move or speak. He let out a gentle gasp and asked, “Your… gran?” He got a hint of a nod. He stepped closer, now right in front of the other boy as he asked barely above a whisper, “Did it… is she…?”

Caleb nodded and finally lost his fight to hold back. He burst into heavy sobs.

Kai immediately wrapped his arms around Caleb and felt the other boy grip tightly onto him as he buried his face in Kai’s neck. Neither of them spoke, Kai simply held Caleb as he cried helplessly.

After several motionless minutes, they heard sound outside the door, which opened and hit against Caleb’s back.

“Hey, move, what you doing?” Leo demanded.

“Not now, Leo!” Kai replied softly.

“Are ya shagging? Come on, let us in!” Miles demanded.

“I SAID NOT NOW!” Kai snapped back and slammed the door closed. He heard angry muttering on the other side of the door but Leo and Miles made no further attempt to get in. “Sorry about that,” he said softly as he held Caleb again.

“I’m sorry,” Caleb sniffled, “I don’t know why I can’t stop!” He started crying more heavily again.

“It’s okay,” Kai whispered to him as Caleb gripped on tightly, “You can cry as long as you need to. I’m not going anywhere!”