Daring Kai - Part 4 (Patreon)

After a frustrating night of restless sleep, plagued by unpleasant dreams, Kai’s day had not gotten off to a great start. Thanks to the dried-on spunk on his face, his eyes were hard to open. Unable to rub them with his hands due to the restraints, it had been a challenge to even open his eyes at all, though once he did he realised he couldn’t really do anything anyway.

Being tied up to sleep had been bad enough, but the realisation of how helpless he was when he awoke was a sobering first thought of the day. To make matters worse, his dick was raging hard. Disturbing as his dreams had been, it seemed they were a little exciting too, and his morning wood felt like it might never go down.

Just on the verge of calling out for someone to come and untie him, he heard the door open and tilted his head to see Miles approaching.

“Good morning!” Miles said cheerfully.

Kai just grunted in response.

“Well, if you’re gonna be like that, then maybe I won’t bother releasing you,” Miles said with a shrug as he turned away.

“Fine, sorry, good morning,” Kai croaked, his throat dry.

“Wow, you’re a mess, what happened?” Miles asked with a wicked smirk as he looked down at the restrained boy.

“You know what happened,” Kai growled.

“You should probably wash that stuff off, but it looks a bit dry. Maybe we could moisten it up a bit!” Miles said with a thoughtful nod.

Kai was about to object but remembered he had offered daily blow jobs. Miles was clearly just getting it out of the way early. He did let out a groan, however, when Miles grabbed the same underwear from the night before to blindfold him again. “What, you scared I’ll see how small your dick is?” Kai taunted.

“Screw you. I’m bigger than you, bitch-tits!” Miles replied, twisting both of Kai’s nipples at the same time to emphasise his contempt as he climbed on top.

“Oww, fuck,” Kai grunted. “Why don’t you…” The rest of whatever he intended to say was lost as he felt Miles’s dick shoved into his mouth. He was tempted to bite it just to teach him a lesson, but figured it would only cause him more issues so he sucked it briefly before the other boy began to face fuck him again.

A couple of minutes later, Miles was shooting another load over Kai’s face. Almost as soon as he finished, he had climbed off and started removing the restraints holding him onto his bed.

Kai groaned in disgust as he reached up and used his own underwear to wipe off the spunk, using the added moisture to scrub away some of the previous night’s load too.

“Come on,” Miles said as soon as he had the last of Kai’s limbs free. “Caleb’s already here, we’re ready to draw your next dare!” he said eagerly.

“Can I at least get dressed first?” Kai asked.

“Nah, chances are you’ll just have to take it all back off,” Miles said with a smirk as he led Kai out and across the hallway into Leo’s room.

“Oh, just… not even bothering with clothes anymore?” Leo asked as he saw his naked brother.

“I tried to tell him, but he insisted. I think he likes it!” Miles said, holding back a grin.

Covering up as he blushed, Kai glared at Miles who was sniggering at the embarrassment. He shot a brief glance to Caleb who promptly turned his attention to Leo.

“Come on then, gimme the bag, I’m drawing this one so you can’t cheat it!” Caleb said as he held out his hand.

“Rude! I don’t cheat!” Leo scoffed, but handed over the bag anyway.

Kai couldn’t help noticing the nervousness on Leo’s face as Caleb reached into the bag.

“Ugh, lame,” Caleb huffed as he read the scrap of paper. He rolled his eyes and said, “I’m guessing Leo put this one in! It says ‘Let Leo choose what you wear today’!” Annoyed that Leo was getting off so easily, he huffed, “Guessing you’re gonna do it!”

“Yussss! Perfect!” Leo said, visibly relieved. “Yeah, I’ll take it and as I’m just gonna be doing that anyway, let’s go straight to Kai to see how you can make THAT harder!”

Kai thought about the dare for a moment. He briefly considered suggesting it should be for more than just today, but the prospect of being at his brother’s mercy for his clothing choice all summer was not something he relished. He hummed thoughtfully for a few seconds, then sighed at his own twisted imagination as he said, “You get to choose what I wear, but we do it in a clothes shop where you can buy whatever you want, and I have to wear it!”

“Ohhhh, that’s good!” Leo said happily. “Nice, you twisted little cunt. You really love to suffer, don’t you!” he said, sounding somewhere between amused and disgusted.

“Oh yeah, love it,” Kai grumbled.

“Come on then, Smiles,” Leo said, using the nickname he usually threw Miles’s way when he was in a particularly good mood, “What ya got?”

“Hmm, that’s tough,” Miles said with a nod, before his eyes widened and he said excitedly, “I know! He isn’t allowed to use the fitting rooms. Anything he tries on, he has to do it on the shop floor!”

“Damn, you took my one,” Caleb sniggered. Thinking briefly to come up with a replacement for the idea Miles had beaten him to, he nodded to himself and said, “He can’t put clothes back on between trying things. Once things are off, they STAY off!”

“Sweet!” Leo said excitedly, “Okay, and my one then… I’ll be kind and keep it simple!”

Kai rolled his eyes. Leo’s idea of ‘kind’ and his own were very different things.

“Once I’ve picked what you’re gonna wear, I’ll tell you what you have to say if anyone asks about it!” Leo said with a smile and head bob. “See, nothing too bad!”

Kai wanted to disagree, but didn’t want to attract any more punishments for talking back, so he held his tongue. Instead, he asked, “So I guess I should go get dressed for a trip to the shopping centre then!”

“Well technically the dare said I choose what you wear. That would include now, so just give me a minute!” Leo said before he dashed off into Kai’s room. A minute later, after the sound of a lot of rummaging, he returned carrying some clothes.

“Oh!” Kai said in surprise as he saw the unusually normal outfit Leo had selected for him, but his surprise turned to bemused annoyance as he saw the underwear Leo had picked. “I knew I shoulda cleared shit out,” he grumbled as he held up a pair of tighty-whities he had grown out of a couple of years earlier. “These aren’t even gonna fit me!” he declared unhappily.

“Well let’s see ya try!” Leo suggested to the amusement of Miles and Caleb.

Kai rolled his eyes once more as he finally moved his hands away from his crotch and stepped into the old underwear, giving the others a brief glimpse of his cock. He could feel the tightness of the legs as he pulled them up. Thankfully his morning wood had mostly subsided, as it meant his dick had shrunk enough to actually fit into the tiny briefs, albeit only just. His package was squished tightly against his body in a firm lump that was only just covered, while the top of the underwear didn’t even cover the area that, until yesterday, had sported his small patch of pubes.

“A perfect fit!” Leo declared with a wicked snigger, “Come on guys, we got shopping to do!”

*****

So far the morning had felt worryingly humiliation-free for Kai. Despite the tightness of his underwear as a constant reminder of what was happening, the group had enjoyed breakfast together before catching the bus to the St Francis Shopping Centre just a short ride away from home. When they arrived, Kai had expected them to make a beeline for a clothes shop to begin his dare, but they just wandered around for a while first. He suspected it was Leo’s way of building the tension… and it was working. He was completely on edge the entire time, fearing what was to come.

It was almost a relief when they made their way into an actual clothes shop and started browsing. Kai wasn’t sure which way to look, or who to follow as all of the other three spread out. Were they looking for something in particular, or just looking for whatever they could find to embarrass him. The wait was torturous but as he finally got beckoned over by Leo, he suddenly found himself wishing for the wait all over again, if only to delay his inevitable embarrassment.

“Why don’t you try this on!” Leo suggested, offering Kai a t-shirt.

Kai whimpered as he reached down and started peeling off his own top. As he pulled it over his head, he noticed he was already drawing attention. The sudden show of smooth, flawless skin had caught the eye of a couple of other customers, as well as a staff member over by the checkout.

“I’ll keep hold of that,” Miles said as he snatched Kai’s t-shirt away.

“Thanks,” Kai pouted and quickly pulled on the t-shirt Leo had selected for him.

“Hmm, nah,” Leo said, shaking his head almost as soon as Kai had it on. “Stick it back!” he said and promptly marched away.

Kai took the clothing off and returned it to the hanger before hanging it back on the rack. As he turned, Miles was gone too, leaving him to wander around the shop shirtless. None of the commands this time had forbidden him from covering up, so he folded his arms in a poor attempt to conceal some of his body from the other shoppers who were increasingly notice his partial nudity.

Kai soon found himself being called from Leo, to Caleb, to Miles and back again to try on tops, though he never got to keep them on for long. He wasn’t sure whether it was intentional or not, but the embarrassment of just being shirtless was actually magnified by the fact he didn’t just take his shirt off in public once, he did it dozens of times, exposing himself over and over to the random strangers passing by.

“Umm, we DO have fitting rooms, young man!” a shop assistant finally said after several minutes of trying on clothes. He was a young man in his mid-twenties, dressed casually but with a store lanyard hanging around his neck showing his name was Eddie.

Miles quickly answered for him as he said, “Yeah, umm… we’re really indecisive so he’s probably gonna be trying on a lot and last time we were here someone thought we were up to no good taking so many things into the fitting room. We figured this way you can keep an eye on us. I believe our demographic are most prevalent for shoplifting and I’d hate for us to be seen as anything less than honest when all we really want to do is find a cute new outfit for our friend!”

The assistant was a little surprised by both the explanation and the eloquence of the response. The others were mostly just amused, knowing Miles was both smart and quick-witted, so his ad-libbed excuse was impressive but unsurprising.

“Oh, well, you certainly seem trustworthy… but the best shoplifters always are!” Eddie said with a chuckle. “You do what you need to do then and I’ll make sure to keep a close eye!” he said cheerily.

“On me, or him?” Miles asked with a smirk.

Eddie blushed a little and just chuckled as he walked away and chatted quietly with his colleagues.

“Hey, whadda you think of these?” Leo called out, holding up a pair of shorts. “Kai, come try ‘em on!” he said with barely-concealed glee.

Kai felt a knot in his stomach. He knew this was coming, but that didn’t make it any easier to handle. As he approached Leo, he trembled a little. Taking off his jeans with regular underwear beneath would have been hard enough, but clad in just the tiny briefs it was pure nightmare fuel. He unbuttoned and slid the jeans down, closing his eyes for a moment as he imagined who could now see him near-naked. Annoyingly, he had to pull his trainers off to remove his jeans and, without any socks on, he felt his bare feet touch the cold floor. Somehow, it felt more exposing than the fact he was wearing nothing but pants in public.

Kai grabbed the shorts as he saw Miles snatch up his jeans and trainers and quickly pulled them on. He barely had them up to his thighs before Leo said, “Nah, don’t like ‘em!” Clearly the clothing was little more than an excuse to progress Kai’s exposure.

Once again Kai was back to running around the shop from person to person to try on clothes, both tops and bottoms this time. Shoppers around him were sniggering at him as he paraded around almost nude, his blushing now so profuse it had spread from his cheeks, down his neck and onto his pale shoulders. While the briefs were an absolute horror, in that they left so little to the imagination, they were also a blessing. They were so painfully tight that they literally prevented Kai’s dick from being able to swell, even as he felt the confusing twinge of excitement as he humiliated himself in front of countless strangers.

After trying on what felt like every garment in the shop, Kai figured they had to be almost done… until he saw something the scared him more than any other dare, challenge or punishment he had done so far – Leo was heading into the female section. Freezing in place, he stared over at his brother with wide eyes, silently pleading for him to turn around.

“Oh, perfect!” Leo called out, “Kai, get over here!”

“No no no no no no,” Kai muttered shaking his head as he approached his twin. “Leo, you… you never said… this isn’t… you can’t…” he stuttered anxiously as he got near to Leo.

“I get to choose what you wear!” Leo said frankly, “Try this on!”

Kai stared in abject horror at the short, hot-pink tank top Leo was holding. It looked absolutely tiny. “Leo, no, please!” he begged.

“Kai, one more complaint and I send a clip from yesterday to one of your classmates!” Leo growled back at him, “Now try it on!”

Kai let out a shuddery breath and took the tank top, pulling it on over his head. It was skintight, clinging against his scrawny torso. The straps were barely more than two centimetres wide, while the bottom of it only came to slightly below his nipples, leaving his midsection completely exposed.

“Oh, now that’s cute!” Leo said with a nod as he looked at Kai in the tank top and white briefs. “Just needs one more thing!” he added as he turned away. “You can keep that on,” he called back without looking round.

“Wow!” Miles said as he appeared nearby and looked Kai up and down. “That’s… certainly a look!” he said, very visibly struggling to contain laughter.

“Shut up Miles,” Kai pouted as he marched after Leo.

“You look cute!” Caleb stated as Kai passed him.

“Shut up!” Kai growled angrily.

“I was…” Caleb started, but sighed and shook his head as he watched Kai continue on.

“Here!” Leo said as he held out another hanger. As he saw Kai preparing to complain, he pulled out his phone and raised an eyebrow. The threat didn’t need to be spoken.

“Fuck you, Leo,” Kai muttered angrily, so embarrassed now he was almost in tears. The item he had been handed was a tiny pink pleated skirt. Panting heavily from sheer anger, Kai leaned down and stepped into it and pulled it up. Covering up the briefs should have been a relief, yet it was even more embarrassing than being in just his underwear.

“Come on, that’s a bit low,” Leo said, shaking his head as he reached out and grabbed the waistline, tugging it up a little.

The bottom of the skirt rose to mid-thigh on Kai, barely concealing the underwear beneath.

“Ah, that’s better. Whadda you guys think?” Leo asked, looking past Kai.

Kai turned to see Miles and Caleb both standing there staring at him.

“Weirdly hot!” Miles said, seemingly honestly.

Caleb hesitated, clearly cautious to say anything else, so he just nodded as he looked Kai up and down.

“Well there we go. That’s today’s outfit chosen. Let’s go pay and get the hell outta here!” Leo said confidently.

As the group approached the checkout, Kai continued to draw attention from the other shoppers, many of whom were openly whispering and pointing his way.

“Huh, certainly not what I was expecting,” Eddie said with a nod as he looked at Kai, “But quite a good look!”

“Thanks,” Kai said shakily.

“I assume you’re wearing it out of the store!” Eddie stated, getting a nod from Leo. “Great, if you could lean this way I can scan them and I’ll pop the tags out for you!” he stated as he leaned in with the barcode scanner.

Kai blushed more as he exposed bits of himself again to show the barcodes, then felt the young man’s hands brush his skin as he removed the tags.

Leo paid for the clothing and Eddie handed him a small bag and said, “Tags are in the bag with the receipt. Enjoy your day!”

“Oh we will!” Leo said happily as he headed out with the other three close behind.

Kai let out a whimper as he stepped out into the shopping centre. Immediately, he felt eyes on him. Some people looked amused, some appalled and a few strangely aroused. He heard whispers right away and it was a surprising mix of negative and positive, along with a worrying amount of comments that were insensitive at best, and outright transphobic at worst.

“Hey, round here,” Leo said, stepping round to a slightly more discrete corner. As the others followed him round, he smiled and said, “Miles, you can give him his trainers back. We don’t want him stepping on anything and hurting himself!”

“Just emotional harm only today please,” Kai said bitterly.

Leo ignored the comment and said, “We won’t be needing these now!” He reached up under both sides of the skirt and grabbed the briefs to start pulling them down.

“No!” Kai objected, grabbing hold of them.

“Kai, let go or get punished!” Leo said angrily.

“Fuck,” Kai grunted as he let his brother pull the underwear down and stepped out of them. The briefs were added to Miles’s bag, where his other clothes had been stashed. He slipped his feet back into the trainers Miles had placed on the ground and felt a sudden chill down below as his cock, balls and butt were exposed to the open air.

“There ya go, good girl!” Leo sniggered.

“If you think ‘girl’ is an insult, it explains why you’ve never actually had a girlfriend!” Kai said sharply. He saw the hurt look on his brother’s face, especially as the other two sniggered, but didn’t say anything else or apologise.

“So, who’s up for some shopping. I got a feeling we’re gonna be here for a while!” Leo said, doing his best to look unbothered by what Kai had just said to him.

Kai groaned at the prospect of spending the day walking around the shopping centre in the humiliating outfit. Surprisingly, the fact it was girls’ clothes didn’t actually embarrass him as much as the fact the outfit showed a lot of skin and drew a lot of attention to it. Making the mistake of allowing himself to think the embarrassment couldn’t get any worse, his now-free cock soon reminded him that ‘worse’ is always possible. His dick began to swell.

“Oh my god,” Miles guffawed at the sight of the bulge.

The skirt was long enough that it covered his short erection, but only just. It would only take a slight lean downwards for anyone to see the tip of Kai’s boner poking out from beneath it.

“This feels like a slight design flaw,” Miles cackled.

“To be fair, most girls don’t need to worry about erections, and those that do probably wear underwear!” Leo stated, joking but not incorrect. “Oh well, I’m sure it’ll go down eventually. Them too!” he added, pointing to Kai’s chest.

Blushing once again, Kai looked down to see his erect nipples showing very visibly through the tiny, tight tank top. “Oh my god, fuck my life,” he groaned.

“Let’s not forget the final part of this dare,” Leo said almost bouncing with excitement.

Kai huffed. He literally had forgotten that Leo still had another part to add. “What is it then? What have I gotta say?”

“If anyone asks you about the outfit,” Leo said with a smirk, “You just say to them, ‘I wanted to be a pretty pink princess today. Do you think I’m pretty?’ You got that?”

“Are you serious?” Kai asked, looking appalled.

“Hey Kai,” Leo said with a lop-sided smile, “What’s with the outfit?”

Kai looked apoplectic at the command, but didn’t lash out. Through gritted teeth he replied, “I wanted to be a… pretty pink princess today! Do you… do you think I’m pretty?”

“Yes!” Caleb replied. As the others looked at him, he blushed slightly, but quickly burst into laughter as he said, “Pretty pink princess! That’s fucking classic!” The others joined in laughing.

“Mate, you’re in for a bitch of a day!” Miles said, sounding almost sympathetic.

Leo nodded along with the comment. “Yeah, tough day out for you, Kai,” he said, trying to sound as sympathetic as Miles… and failing as he added, “But we’ve got a surprise for you!” He gave a sweet smile… which scared Kai.

“What?” Kai growled.

Leo reached into Miles’s back, rummaged around for a moment and said, “We brought this with us!” He pulled out the dare bag. “I think it’s time for your next one!” he said as he waved the bag menacingly.