Daring Kai - Part 5 (Patreon)

“I wanted to be a pretty pink princess today. Do you think I’m pretty?” Kai asked as the sound of sniggers echoed around him. He had expected the embarrassment to die down the more he got used to saying it, but somehow it was just getting worse. Walking around in the skimpy pink tank top and mini skirt with his legs, midriff, shoulders and arms exposed, he almost wished he could just be fully nude. Surely that had to be less humiliating than claiming to be a ‘pretty pink princess’ repeatedly.

Leo, Miles and Caleb had worked their way around most of the shopping centre, deliberately heading to anywhere that seemed busy in order to draw more attention to Kai and his embarrassment.

Despite the constant stream of onlookers, teasers and taunters, Kai actually felt surprisingly safe. As much as the other three were clearly enjoying his ordeal and actively encouraging the teasing, they had gone out of their way to look after him.

“Look but don’t touch!”

“Hands off!”

“No means no!”

“Touch him and lose the fucking hand!”

These were just a few of the comments and threats the other three teens had thrown out around the spectators who took the slutty appearance as non-verbal consent to do whatever they wanted. A few times, they had even gone as far as slapping hands away, or the occasional shove to keep the more eager taunters away from Kai. It also helped that Leo was continuing to record almost every moment. Nobody seemed willing to risk overstepping while being recorded.

It was a confusing arrangement, having the same people who were tormenting him protecting him. Kai couldn’t really give it much thought as his focus remained, as always, on that damn sentence – “I wanted to be a pretty pink princess today. Do you think I’m pretty?”

The route Leo was leading them on seemed to make very little sense to Kai either. They seemed to be constantly going up and down, never sticking to the same floor for very long. Eventually, as they got onto an escalator mere moments after leaving another, he had snapped at his brother and said, “Fuck’s sake, I get you wanna drag this out, but pick a fucking floor!”

“I would,” Leo had replied before bursting into sniggers, “But I’m guessing you hadn’t noticed… every time we go up an escalator, everyone behind us can totally see up your skirt!”

Kai had discovered in that moment entirely new levels of humiliation he hadn’t even dreamed possible before. Strangers had been seeing his butt every time he rode up a floor. As expected, as soon as he tried to reach back to conceal his butt, he was banned from doing so. From then on, he had to stand on the escalators fully aware of the show he was putting on. In turn, that meant reaching the top of each one with the front of the skirt lifted slightly as it rested on his persistent erection.

The boys were just leaving a shop, laughing away. When asked, “Do you think I’m pretty?” he had answered with, “Fuck yeah, I’d tap that!” As they got outside, Leo stopped to catch his breath from laughing so much, then said, “Okay, come on then, let’s see what’s up next!” He pulled the dare bag out.

“Kai’s dick, probably!” Miles sniggered.

“Ha fucking ha,” Kai scowled.

“Do we have to do it here?” Caleb asked anxiously, “I’m probably not gonna want to do whatever gets drawn out while we’re here!”

“Tough, we’re doing it anyway!” Leo said as he reached into the bag of dares. “So Caleb, your next dare…” he paused to unfold the paper and read out, “Stick something up your bum!”

“What? Someone actually wrote that?” Caleb asked, snatching the paper. He rolled his eyes and looked at Miles as he recognised the handwriting.

“What? Don’t judge me!” Miles said back petulantly, “It’s a fun dare!”

“Guessing you’re not gonna…” Leo started, but paused as he saw Caleb reach into the back of his sweatpants.

“There, done!” Caleb said as he pulled his hand out, “Stuck my finger up!”

“We didn’t see it!” Miles said unhappily. Finding ways around his own dares was funny and clever. When anyone else did it, it was wrong. It was a double standard he was shameless in admitting.

Caleb held out his hand and said, “You’re welcome to sniff it and check for yourself!”

“Ewwwww!” the other three chorused, getting a proud snigger from Caleb.

“Mate, what the fuck is up with that outfit?” a teen slightly older than the four of them asked as he stopped, along with some friends who burst into laughter at the sight of Kai.

Kai sighed and said, “I wanted to be a pretty pink princess today. Do you think I’m pretty?”

“I think it’s fierce! You go girl!” the teen said without a hint of derision, then walked on as his friends seemed to start teasing him about it.

“Ah, it’s really the gift that keeps on giving,” Leo sniggered at the clothes his twin wore. “Anyway, Caleb did his dare, so you know what that means!”

“Fuck!” Kai grunted. Butt stuff was something Kai had thought about. He had watched it, fantasised about it, watched more of it, but never actually tried it. Needless to say, doing it while near naked in a public place with his brother and friends around him was not how he had imagined he would eventually give it a go. Knowing the drill by now, he thought for a moment about how to make the dare worse for himself and stated, “I dunno, umm… whatever I stick up there I have to… to keep it up there til we get home!”

“Ah sick,” Miles sniggered, “I say it has to be bigger than a finger!”

“Fair,” Caleb nodded, then quickly added, “Then I’ll say… if it comes out before we get home, he gets a punishment for each time it comes out!”

“Ha, awesome,” Leo grinned, “Miles, you got a pen in your bag?” As Miles nodded and pulled out a pen, Leo took it and flipped the piece of paper over to write on it. Handing it to Kai, he said, “You gotta go into the shop over there and buy the two things I wrote down! We’ll see you at the checkout.”

Kai took the paper, read it and then glared furiously at his twin. “Money,” he said, holding out his hand. He snatched the card from Leo’s hand and stormed off into the shop.

“What was it?” Miles asked eagerly.

“Wait and see!” Leo sniggered as they lingered near the row of checkouts. A minute later, they saw Kai approach one of them and moved to the end of it, watching as the person in front of him got served. “Here! Here it comes!” Leo whispered to the others.

As the person ahead of Kai left and the conveyer on the checkout rolled forward, a single large carrot and a tub of KY jelly rolled towards the cashier. The young woman looked at the items, then to Kai, looking him up and down as he blushed profusely. She didn’t say a word, but her smirk said everything it needed to, especially as Leo, Caleb and Miles burst into laughter.

Kai paid for the items, glaring again at Leo as he refused a bag from the cashier, then followed the laughing teens out of the store with the embarrassing items in hand.

As they got outside, Leo wasted no time in opening the jar. He tried to shove the carrot in, but the jelly was harder than he expected so he stuck his fingers in and scooped some out, then slathered it onto the carrot, leaving the top two inches unlubricated where he held it. Looking at his slippery hand, he scowled and then reached out to wipe it on Miles’s top.

“Fuck you!” Miles complained as he got covered in the discarded jelly, before putting the tub away in his bag.

“Turn around,” Leo growled.

“I can do it!” Kai insisted.

“I said… turn around!” Leo said firmly.

“Mate, come on,” Caleb said, shaking his head. “It’s tough enough already. At least let him do it himself!” he said sympathetically.

“Fine,” Leo huffed, “But once it’s in, you’re not allowed to touch it again!”

“Fine,” Kai agreed, shooting Caleb a brief thank you smile. Nervously he took the carrot, glad of the human shield the other three made as they concealed him in a corner. Wincing as he looked at the carrot, he reached back and placed the tip into the cleft of his butt. He didn’t find the hole right away, instead working the tip downwards until he felt the right spot. He gulped slightly as he started pushing it in. He was glad Leo had put so much lubricant on as it certainly made the entrance easier. He attempted to relax a little and felt it get a little easier and less painful, so he took a deep breath once again and attempted to unclench. It definitely helped, as he felt the carrot sliding inside himself.

“How does it feel?” Miles asked curiously.

“Like there’s a fucking vegetable up my arse!” Kai growled back at him, getting amused smirks in response from the others. He pushed a little more and stopped as the unlubricated part reached his hole. He had around four inches inside himself, though it felt like a lot more. He wasn’t sure if he was supposed to push it all the way in, but worried that it he did he may not be able to get it back out, so he pulled his fingers away and immediately tensed his buttocks. “Oh fuck,” he grunted as it changed the position slightly, moving inside him as he kept it inside. “How… how long… til we go home?” he asked shakily.

“Oh, hours yet! Absolutely ages!” Leo said with a wicked grin. As he saw a look of absolute dismay on Kai’s face, he sighed and said, “Fine, just a quick walk back through the centre and then onto the bus, okay?”

“Thank you!” Kai said, panting slightly. “Fuck,” he added as he looked down to see the skirt tenting again.

“Damn, you’re really into that then!” Miles said, more observation than tease.

“I don’t know,” Kai whimpered, sounding genuinely confused.

“Come on, let’s walk,” Caleb said as he turned away.

“Oh, that feels weird,” Kai gasped as he started walking, keeping his buttocks tightly clenched.

Leo laughed and replied, “I’d be worried if it didn’t!”

They continued walking through the shopping centre, stopping two more times when Kai was questioned about his outfit, delivering the required line with a little more shakiness than he had before, blushing heavily at the knowing looks the bulge in his skirt got.

“Oh fuck, it’s sliding out!” Kai groaned as they continued on, despite his desperate clenching.

“Nuh-uh,” Leo said as he grabbed Kai’s hand. “You’re not allowed to touch it, remember!”

“Then… what do I…” Kai panted, scared at the prospect of it falling out. It wasn’t so much the thought of punishment that scared him, it was more the humiliation of having a carrot fall out of him and onto the floor in front of the many strangers around them. As if their stares weren’t bad enough, he couldn’t tolerate that too.

“He can’t, but we can!” Caleb stated, then stood behind Kai and reached as discretely as he could to push the carrot back in.

“Oh fuck!” Kai gasped, feeling his knees almost buckle at the carrot pushing back into him.

“Wow, I reckon Caleb wants to make him cum again!” Leo taunted.

“I’m not… gonna cum!” Kai growled back at his brother.

“Not yet, but home’s a long way off!” Leo smirked, “Come on, next bus is due soon!”

They all hurried on through the shopping centre. Kai began signalling Caleb any time the carrot started to slip, which was happening increasingly often as the carrot and his hole got increasingly slippery. By the time they got outside and headed for the bus stop, Caleb’s hand seemed to be in Kai’s butt every few seconds, fucking him repeatedly with the vegetable.

“Oh thank fuck!” Kai gasped as the bus pulled up a few seconds after they reached the stop. He was so relieved to be heading home that he barely even blushed at the recital of the embarrassing phrase two more times – once to some passengers and the other to the bus driver.

Heading to the top deck of the bus, the four boys rushed to the back row and sat down. Kai let out a shuddery gasp as he sat, the carrot pushing deep into him, now at an entirely new angle. His cock twitched, knocking the skirt off and leaving him sitting with his erection exposed to the other three. “Lemme guess, no covering up?” Kai groaned, getting a nod back from the others as they continued to laugh and revel in his humiliation.

Thankfully their position meant nobody was going to be walking past them, so Kai was able to sit exposed but relatively safe as they travelled the short distance home. As they neared the final stop and Miles pressed the button, Kai steeled himself to stand, clenching tightly as he stood to keep the carrot inside. Despite his best effort, it slid out a little and he blushed as he said, “Caleb, could you…”

As Kai trailed off, Leo finished for him, “Fuck him with a carrot!” Leo and Miles burst into hysterical laughter.

Caleb shoved the carrot back in and they all headed back to the front of the bus and down the steps as the bus pulled up.

“Bye, pretty pink princess!” the bus driver said as they stepped off, getting laughter from the boys and a few of the passengers.

Kai just let out an annoyed grunt. On the bright side, home was now close as the bus stop was only a short distance away from the corner, where they usually met.

“This was fun, we should totally do it again,” Leo said happily as he strolled along with the others.

“Well technically we need to put four more dares into the bag, so… we could easily make that one of them!” Miles stated.

“Oh yeah!” Leo said happily, “I forgot that bit!”

“Wow, thanks Miles,” Kai pouted before he felt the carrot slipping and muttered, “Fuck, Caleb…”

Caleb nodded and reached across to shove the carrot in once again as they neared the end of the driveway.

Kai gasped sharply at the vegetable pushing into him, but the breath caught in his throat and he coughed loudly. The tensing of his body as he coughed suddenly expelled the carrot from his rear like some kind of vitamin-loaded missile. “No!” he yelped through his coughs as he realised what had happened.

“Ahhh, so sick!” Leo burst into laughter as he saw the carrot fly out.

“Good distance!” Miles sniggered.

“Fuck fuck fuck,” Kai growled.

“Oh, punishment time!” Leo called out, “And I totally know what he should do! He has to EAT the carrot!”

“Aww, gross!” Miles baulked.

“What, no way!” Kai insisted as he retrieved the carrot from the floor.

“Yeah, you heard me. Eat up!” Leo insisted.

“Yeah, no,” Caleb said, shaking his head.

“You gone fucking soft!” Leo scowled, then sniggered as he looked to Kai and added, “Unlike Kai, who never goes soft!” The joked received a celebratory high-five from Miles.

“I’ve not gone soft, I just know that’s really fucking unhygienic. Kai gets sick and there goes our entertainment!” Caleb explained, “Besides, we draw punishments from the bag, we don’t just make shit up as we go along!”

“Fine, whatever,” Leo grumbled, “But draw it now. If it’s embarrassing, he can do it out here!”

Miles pulled the bag of punishments from his backpack and held it out for whoever was going to draw it.

Kai reached out and slipped his hand into the bag, then pulled it out and read it. “Seriously?” he sighed as he shook his head. He held up the paper which bore just two words – Cum! Twice!

“Oh yeah, he’s definitely doing it here!” Leo said with a nod, almost giddy with excitement as he continued on with his frequent recording.

“Fuck you all,” Kai pouted and shamelessly grasped at his dick, letting the skirt bunch up above it as he quickly began stroking. Thankfully, the day of humiliation, embarrassment and torment had kept him horny and built up a lot of tension, while the carrot-fucking had been gradually pushing him towards the edge so it took less than thirty seconds before he was letting out a shuddery groan and spurting his first load of the day onto the pavement.

A car drove past and honked its horn, though it was unclear whether it was just because of the outfit or if they had seen what Kai was doing. Either way, paired with his post-orgasmic comedown, it was a sobering reminder of his situation.

Keen to get the second load down and out of the way, Kai grasped at his wet, sticky prick, but let out a shuddery groan at the post-nut sensitivity and had to let it go. “Gonna… need a minute,” he gasped shakily.

Miles and Leo both exchanged smirks. “You thinking what I’m thinking?” Miles asked.

“Yeah, probably, definitely something to put back into the bag as a new dare!” Leo agreed, getting a nod from Miles as the two both got the same idea.

“Fuck,” Kai muttered. A few seconds later, still sensitive, but desperate to get it over with, Kai started wanking anyway. It was a little painful and not at all sexy, but masturbating in front of Caleb, Leo and Miles made it at least slightly exciting, even if he would never admit it. Despite cumming mere moments earlier, the excitement of the day and the pressure it had built was still enough to make things happen quickly. Kai was not quite fully hard, but hard enough to get things done.

“Damn, you can get going again that quickly!” Miles stated in seemingly genuine admiration. “I gotta wait, like, hours before I can even touch it again!” he shared casually.

“Didn’t really need to know that!” Caleb said, smirking at Miles as he blushed at the realisation of his admission.

Leo just stared at his best friend, blushing too until the noises from Kai drew his attention back.

“Fuck, fuck, fuck, I’m close, I’m close!” Kai gasped. “Ah no,” he groaned as he heard voices. Looking back down the street, he could see a group of people approaching. “Fuck fuck fuck fuck, come on, pleeeeeease!” he pleaded his cock to comply. “Ah, fuck yes,” he gasped, finally crossing the point of no return just as the approaching group saw them. He could hear laughing and shouting as he shot his second load and immediately sprinted down the driveway towards the front door.

Laughing heartily at Kai getting spotted, the other three quickly followed and let him inside the house.

“That was… horrible,” Kai whimpered.

“But you did it!” Leo said, sounding almost proud. “Why don’t ya go clean off and get dressed… in whatever you want. We can just chill for now!” he offered.

“No more dares?” Kai asked hopefully.

“Hmm, not til later,” Leo said with a wicked grin. He glanced to the other two and said, “One of you go supervise him!”

Kai immediately looked hopefully at Caleb, who looked avoided his gaze and said, “Miles, you go!”

“Fine, whatever,” Miles shrugged. “Come on, princess,” he said as he headed for the stairs.

Kai groaned softly as he looked at Caleb, who was very deliberately not looking back. He let out a dejected sigh and followed Miles up the stairs. As he neared the top, he remembered the escalators and glanced back. He caught both Leo and Caleb looking, though they promptly scurried away, pretending they hadn’t been.