Daring Kai - Part 11 (Patreon)

“Wait, you’re not coming over with me?” Kai asked as his twin and their friends stopped. He looked out across the Regents Retail Park’s expansive car park. The massive space was surrounded on three sides by large stores, with people coming and going all over the place, both on foot and in their cars.

“Nah, we’ll enjoy the show from here!” Leo said, already aiming his phone, “The zoom on this thing’s great… and I don’t just mean for finding your tiny dick!”

“Mate, you’re hardly fucking massive yourself,” Caleb said, never one to pass up an opportunity to insult Leo.

“Fuck you!” Leo snapped at Caleb before looking back to his brother, “Anyway, go on, you know what you gotta do!” He nodded over towards the far end of the car park where some large charity collection dumpsters stood.

Kai let out a slight whimper and said, “You’d best still be here when I get back!”

“Like we’d wanna miss the show!” Miles called out with a wicked cackle as Kai took off on his bike.

Kai cycled across the car park in a few moments, remaining standing on the pedals as his saddle had been removed as part of the punishment to increase his visibility. He came to a stop by the collection bins and glanced back over to where the other three stood. He already had the other three teens watching, and doubtlessly as soon as he started stripping other people in the car park would begin to notice too. Plus, Leo was recording it. He felt completely on show. It was humiliating and degrading, which made his growing erection all the more confusing.

He had dressed in clothes he didn’t mind getting rid of, but also ones that were quick to remove so he could make a hasty exit. His t-shirt was old, baggy and slightly frayed in places, one he worn in bed for quite a while until he switched to sleeping in just his underwear. It quickly came off and got placed over the handlebars of his bike. Already he was down to just a single item of clothing - his shorts.

They had gone to the shopping centre before stopping by at the retail park so that the others could buy his outfit for another punishment that would take place the next day. Although he wasn’t humiliated at the mall like he had been last time – the ‘pretty pink princess incident - he had still ended up embarrassed on several occasions. The constant teasing from his friends, and thoughts about his imminent naked bike ride had caused him to get a little excited. Wearing the shorts without underwear had been done to speed up his strip, but it had also inadvertently made even the slightest arousal painfully obvious too. He had seen plenty of people passing him by as he walked around, smirking at the tent on his shorts. They were bulging just as obscenely now!

“Fuck my life,” Kai sighed as he grabbed his shorts and slipped them down, easily sliding them over his trainers without removing them. He had turned away from Leo and the others so as not to put himself on show, but in doing so he realised he had just flashed his butt to the entire retail park instead. Any hopes that he had not been seen were dashed by the immediate sound of a car honking its horn, followed by a couple of male voices shouting something unintelligible.

Kai grabbed the t-shirt along with his shorts and stared at them for a brief moment. Once he put them into the collection bin, there was no way of getting them out. Even without the torment of the additional challenges in getting home, he was a ten-minute naked ride from the safety of clothing. His cock positively throbbed as he reached up. As he let go of the clothes, he gasped a shaky, “Fuck!” Frozen for a second from the magnitude of what he had just done, another car horn shook him from his stupor. He jumped towards his bike. He got on and started pedalling desperately across the car park.

Conscious of his erection bobbing about from side-to-side as he pedalled, Kai attempted to reach down and cover it. Had he been seated, riding with one hand on the handlebars might have been manageable. Unfortunately, being forced to stand meant that without both hands holding on, as soon as he shifted his weight to pedal on the unsupported side, he veered wildly and nearly fell off. Placing both hands back on the handlebars and resigning him to a ride home without covering up, he headed for his friends who were in absolute hysterics watching him approach.

“I fucking hate you all!” Kai yelled as he heard a cacophony of car horns, laughter and shouts around and behind him as more and more people noticing the naked teen. “Now keep up or I’m leaving you behind!” he called out unhappily.

Leo slipped his phone into the mount on his handlebars, unsure how well it would capture the ride, though it was certainly better than nothing. He took off after his brother along with Caleb and Miles who were both still laughing at the red-faced, pale-butted figure ahead of them.

“Stop there!” Leo called out as they reached the end of the street.

“Fuck,” Kai grunted. Part of his dare was that he had to stop at each junction to play rock, paper, scissors, and was only allowed to head in the right direction if he tied or won. It inevitably meant the journey home would take even longer, but what he hadn’t considered was that stopping at the junctions only increased his visibility. With drivers slowing or stopping entirely before turning, and sometimes queuing to wait for an opening, he would likely have an audience at almost every single one!

As he came to a stop, he placed one foot on the ground and clasped both hands over his privates as a car full of laughing people drove past, calling out things he couldn’t make out. “Hurry up!” he snapped moodily as the others caught up to him, “From now on, if I have to wait more than a few seconds, I just go which way I want!”

As much as the others wanted to torment Kai, they could see that he was close to breaking point and didn’t argue with his suggestion. Instead, they just silently resolved to match his pace.

“Okay,” Leo said as he stopped and held out a fist, “One, two, three, go!” He kept his hand in a fist while Kai’s hand was held out flat. “Fuck!” Leo grunted at his loss, then quickly started pedalling again as Leo took off towards home.

Each street they rode down went basically the same way for Kai – cars passed him and he sped past pedestrians, all of them laughing, pointing and shouting. Though there were a few scandalised faces, most just looked surprised or amused at the naked teen, figuring it was just some childish prank or YouTube stunt. If anyone was truly offended, Kai was long gone before they even had the chance to do anything about it.

Mush to his relief, Kai won the draw at the next junction against Caleb, but lost at the third one against Miles. “Hmm,” Miles hummed as he looked around all four options at the crossroads they were stopped at and said, “This way!”

“No. Fuck!” Kai grunted as he saw the road Miles had chosen. It was a long, straight road which meant he would be more visible for longer in both directions. It was also an annoyingly long way to the next junction which would add a substantial amount of time to his exposure, which also brought with it other forfeits that Kai was trying desperately not to think about.

“This is fun, we should go on more bike rides!” Leo teased as he followed close behind his twin.

“Yeah, but maybe a route with a better view next time!” Miles joked, getting a scowl back from Kai.

Caleb laughed along with the comments but didn’t add anything further to it.

Blushing constantly, Kai turned an even brighter red as he got to the end of the road and stopped. It was a busy junction with a queue of cars in two of the directions as traffic flowed back and forth across it. Instantly he was drawing stares and shouts once again as people in the stopped cars saw him and began laughing and calling out.

“Nice dick!” “Great day for it!” “If you got it flaunt it… or if you don’t got it, flaunt it anyway!” “We can see your butt!” “Someone call the police!”

Kai was so distracted he almost missed Leo’s count for their next game but drew scissors at the last minute to beat Leo’s paper. “Yusss!” he hissed as he turned his bike and took on back down the long road. As he cycled along, his cock was positively aching as it slapped about, side-to-side and occasionally up and down. He had cum five times that morning (in the space of one hour) yet already he could feel himself needing to cum again, though he had no idea when he would next be allowed to do so.

He allowed himself a brief moment to imagine just ejaculating from both the embarrassment of his current dare and the movement of the cycling, shooting a load in front of all the passing cars. It was an intoxicating thought that almost become self-fulfilling, so he forced himself to stop. The last thing he needed was ANOTHER punishment for cumming without permission. As he got to the end, he played Caleb again and looked utterly distraught as he lost, and Caleb directed them right back down the same long road once again.

“Just so you know,” Leo called out as they followed Kai, “You’re getting close to having to send someone one of your videos!”

Kai groaned. He didn’t want to think about the final part of his punishment, courtesy of Leo. It involved the video clips from one of his earlier dares – the one in which he had masturbated while talking about his classmates masturbating while talking about a classmate. For every five extra minutes it took to get home, he would have to send one of the clips TO the classmate he was talking about. Thinking about it, on top of the fact he was naked in the street in broad daylight, he was beginning to feel a little overwhelmed. He also felt painfully close to cumming, but this likely wasn’t the time to think about why he was enjoying these dares so much! “Wait!” he called out as he hit the brakes so hard that he almost flew over the handlebars.

“What?” Caleb asked as he and the other came to an equally abrupt halt, with the sound of skidding tyres.

“The punishment!” Kai stated, “It was to dump my clothes in the collection bin, right?” He positioned himself to hide as much as he could from the passing cars behind a large tree.

“Yeah,” Miles answered, “Plus no saddle, the game at each junction and the videos for how long you take. Why?”

“Someone gimme some clothes!” Kai said eagerly, “The dare never said I couldn’t put other clothes back on!”

“No!” “No chance!” “Fuck off!” the others chorused back.

“Put it this way, I’m willing to do pretty much WHATEVER you ask if you’re willing to give me stuff to wear!” Kai said, looking mostly at Miles and Caleb, as he knew Leo was enjoying the dare too much to help him.

“Anything?” Caleb asked, wide-eyed.

“And, like… in front of the others or in private?” Miles asked.

“In private!” Kai said with a nod, knowing it was more likely to pique their interest than something that might embarrass them in front of their friends.

“Oooh!” Miles called out, then moved close to Kai and whispered in his ear.

As Miles pulled back, Kai gulped slightly as he looked at the other boy, then nodded a little and said, “Yeah, okay, for your underwear and hoodie!”

“Deal!” Miles said as leaned his bike against the tree. Pulling his shorts and underwear down in a single gesture as he let his hoodie conceal his privates and his butt, he stepped out of them, tossed the boxers to Kai before pulling the shorts back on. As Kai quickly pulled the underwear on, Miles pulled off his hoodie and tossed it to Kai, quickly pulling his t-shirt down as it had ridden up.

“This is fucking cheating!” Leo scowled.

“Rules didn’t say I can’t!” Kai said with a cocky grin as he pulled the hoodie over his head.

“He’s not wrong,” Caleb agreed.

“Great, so let’s go!” Kai said, happily dressed again as he took off. On a normal day, being out with just underwear on his bottom half would have been mortifying, but after spending the last quarter of an hour naked, it didn’t seem quite so bad. He immediately stopped drawing so much attention, much to his relief.

They soon reached the end of the long road where Kai tied against Miles and a quick ride back down it and he tied again against Leo, letting him finally continue towards home. Though he lost a few more times, the diversions were mostly short and soon enough they were at the final junction, where Kai beat Leo one more time to earn his way back towards Miles’s house. While they tended to spend more time at Kai and Leo’s house, they were spending most of today at Miles’s house as Mr Beston had said he was expecting a couple of deliveries, having taken advantage of having someone home during the day for a change.

“Mate, I can’t fucking believe you just did that!” Caleb said in genuine admiration as they got back.

“I can’t believe you cheated,” Leo pouted.

“He didn’t cheat and if you keep bitching about it, we’ll make YOU do another dare!” Caleb said pointedly.

“Pfft, I’d like to see you try, cuntface!” Leo snapped.

Caleb shrugged off the insult and asked, “You don’t think we got enough shit on you to make you do stuff now?”

Leo blushed profusely as they slowed to a halt on Miles’s driveway and stuttered, “Err… umm… you… I’d destroy you too!”

“SO scared,” Caleb said with a dismissive eye roll as he passed by Leo.

“Well whatever, it’s done now and… oh, would you look at that!” Leo said with a grin as he checked the time, “Twelve minutes longer than usual!”

“Fuck!” Kai grunted. Five minutes for each video, that was the dare. That meant he had to send videos to two of his classmates. Not a thrilling thought.

“Well, we know the first one,” Miles said a bemused eye roll as they headed inside the house.

“We do?” Kai asked curiously.

“Duh!” Miles said, pointing to Caleb as they headed into the lounge, casually flopping down into seats.

“Oh! Yes! Caleb! I choose Caleb! Send it to him!” Kai said excitedly, then muttered sheepishly, “I totally thought of that!”

“Ugh, pussy move,” Leo grumbled, but sneered derisively as he said, “You don’t get off so easy with the second one. Who’s it gonna be?”

“Fuck,” Kai said as he ran through the options in his head. Thirty boys, thirty classmates… thirty friends! Well… friends may have been an exaggeration. Most were casual acquaintances at best, and couple were outright unpleasant, but it was still thirty terrible options! While they had all almost certainly seen him naked during their years together changing after PE lessons, that was a fleeting glance of him. The videos were… much more exposing, and not just physically. Being fully nude and hard was bad, masturbating was worse, but it was the fact he was actively talking about them that made it a truly horrific concept. It was personal, it was intimate and it was something he knew they could never unsee! Having run through the class register in his mind, he reached the end and let out a gentle gasp as he exclaimed, “Luca!”

“Yeah, makes sense you’d pick the gayboy,” Leo stated, shaking his head.

“Hey, save the attitude!” Miles said sharply. It caught everyone a little off guard. While Miles was not afraid to tease Leo, or any of the group, hearing him actually annoyed was a rare thing. “That sounds dangerously close to homophobia and that shit doesn’t fly in this house!” he said pointedly.

“Jesus, chill, I’m not fucking homophobe,” Leo said back defensively. As the others all looked at him, he did genuinely look apologetic as he said, “I’m really not. Sorry, I… forget it, I’m sorry, okay!”

“S’cool,” Miles shrugged, “Didn’t mean to get pissy. You know what I’m like with this stuff. Equality for all, and all that jazz!” He offered Leo a sincere smile and got a sheepish but sincere one in return.

“Okay, okay, I gotta ask,” Caleb interjected, if only to break the awkwardness. “What the fuck did it take for you to give him clothes to wear?” he asked Miles.

“Oh, just a nunya!” Miles shrugged.

“What’s a nunya?” Leo asked with a confused frown.

“Nunya fuckin’ business!” Miles said with a coy smile, getting immediate laughter from all of the other three.

“Nice!” Leo said approvingly, any lingering awkwardness already forgotten, “But anyway, back to business!”

Kai let out a whimper as he stared sadly at his brother.

“You do the dares, you pay the price!” Leo shrugged dismissively.

“Technically it was a punishment, not a dare!” Kai muttered unhappily, then said, “Fine, but… at least let me send it myself!”

Leo already had his phone out, tapping away at it. He thought for a moment and said, “Yeah, so long as we can see it send, that’s fine!”

Kai quickly ran off to get his phone and as he walked back in, he was blushing heavily as he stared at it. It was the first time he had looked at the device since posting his picture earlier that morning… his first of MANY pictures! The replies and comments were much like the ones he had got back on his snap story a couple of days earlier, and it already had over 200 likes! Not wanting to draw too much attention to it from the others, he didn’t mention it and instead just opened the messages he had just received from Leo.

As Kai found the two videos he had been sent, he prepared the first one to send to Caleb and stopped suddenly. “You’ve split the video up,” he stated, cocking his head curiously at his twin. He tapped briefly on his screen as he looked back down and said, “And you’ve actually named the files by each person!” He glanced at his brother again, smirked and asked, “Exactly how much time have you spent looking at your videos of me?”

Leo turned bright crimson as Caleb and Miles both held back laughs, staring at him. “No. Nothing. I mean… it was… I knew…” he stuttered awkwardly, floundering for a moment before a thought came to him and he said confidently, “I just knew I’d need it for punishments. Don’t fuckin’ flatter yourself, ya little perv!”

“If you say so,” Kai smirked, looking away, happy in the knowledge Leo now had the other two sniggering at him. He sent the first video to Caleb, then prepared the second message.

Luca Ward was another boy in Kai and Caleb’s class. Kai didn’t exactly consider him a friend, but he also didn’t consider him NOT a friend. He was very much ‘just’ a classmate, though Kai had been curious for a while about the other boy. Luca was gay, and out. In fact, he was the only out gay kid in their year, something that both excited and scared Kai. While Luca didn’t receive the sort of bullying, abuse or torment that ran through Kai’s mind when he imagined coming out, he didn’t necessarily have full acceptance either. There were a couple of boys in their class who really seemed to have an issue with it, but they were generally unpleasant to everyone, so he wasn’t sure it was really about Luca’s gayness.

LGBTQ things were discussed and taught at school, along with various other matters of equality diversity and inclusion. The general attitude of the students was one of acceptance, though there was always the seedy underbelly of any group that took a darker approach. Luca definitely had a hard time from some people though it had died down over the past year. Now the majority of students at the school didn’t even seem to think about or mention it. Kai had come close to discussing his gayness with Luca on multiple occasions, but every time he thought about it something else came up – someone would come along, or a bell would ring to end a break or… Kai would just wimp out, which was the most common outcome.

As there were no rules in place about what Kai could say along with the message, he decided to try a bit of pre-emptive damage control. [Hi, really hope this doesn’t offend you getting this. I kinda did a dare and had to do some stuff and now I have to send it to you too. It’s really embarrassing and I’m sorry and please don’t show anyone else. Sorry sorry sorry!] He stared for a moment and hit send, then let his hands drop away as he huffed and said, “There, it’s done!”

Leo jumped up to check Kai was telling the truth, smirked at the message and said, “Yeah, you did it. I kinda thought you’d resist more!”

“You mean you HOPED I’d resist more so you can get off on it or whatever… MASTER!” Kai said bitterly.

“Umm, you’re the one getting off on this shit, perv!” Leo scoffed back, “And for that, you’re having another dare!”

“Oh sure, cos otherwise I’m sure you wouldn’t have even considered giving me another one,” Kai said with an eye roll. “Whose turn is it next?” he asked, annoyed but intrigued about what was awaiting him.

“It’s Cay,” Leo said happily, offering the dare bag to Caleb.

“No, it’s not,” Caleb disagreed, “Mine was the cream one and I passed!”

“Oh yeah, I forgot you pussied out!” Leo said derisively.

“Pfft, you’re just pissed cos you were stupid enough to lose a bet so you COULDN’T pussy out!” Caleb said back with a teasing smirk.

“What if… NONE of us could pussy out!” Miles said, cocking his head curiously.

The room fell deathly silent as the other three looked anxiously around at each other and at Miles.

“You ever heard of Mutually Assured Destruction?” Miles asked, looking almost as nervous as Leo and Caleb.

“Punk metal band, right?” Caleb asked with a wry grin. It got a snort of laughter from Leo who blushed slightly at his own noise but offered Caleb a fist-bump for the joke anyway.

“It’s a military thing, but whatever, it’s not exactly accurate here,” Miles said, shrugging off the joke, “I was thinking along the lines of, like… setting something up so that if one of us welches on a dare or a bet or whatever, then the others have the ability to, umm… well… punish them for it!”

“Punish… how?” Kai asked, utterly intrigued.

“Well, with, like… video shit,” Miles shrugged. “Kinda like Leo’s doing with you,” he said to Kai. “But against all of us. I doubt Leo fancies the world seeing him getting blown by his brother,” he said, grinning as Leo looked mortified. He looked to Caleb next and continued, “And unless you want the world to see the hot new porno ‘Caleb’s Creamy Crack’ starring Kai and Caleb, we’ve got that on video for you!”

“Fuck!” Caleb and Leo both gasped at the same time, then blushed and laughed awkwardly in synchronisation too.

“What about you?” Kai asked, cocking his head curiously at Miles.

Miles smiled, then copied the gesture, cocking his head at Leo.

Leo tutted, rolled his eyes and said, “Yeah, okay, fine, I MAY have recorded you blowing him this morning!”

“You twat,” Kai growled at his brother, then looked to Miles and asked, “You knew?”

Miles shrugged and replied, “Like I said, mutually assured destruction. We show anyone Leo doing stuff and he takes us down in retaliation.” Everyone looked quite intimidated by the comment, so Miles went on, “Actually I’m thinking I could set up a thing where the really incriminating stuff is set up and password protected, and can only be released if, like, ALL the other three agree and approve it. So, like, Leo skips a dare, so we wanna punish him, but we can’t send his stuff out unless all three of us agree on it, but then he can’t retaliate cos the rest of us wouldn’t approve him trying to send our shit!”

“What, so… you set that up and what happens? All of us HAVE to do the dares from now on?” Caleb asked nervously.

“Yeah, we know Kai’s a little perv who’ll do whatever we tell him, but… I dunno, I kinda like the thought of a bit of risk too. It’s like Leo said before we started, the fun’s in the risk, right!” Miles reasoned.

“But Caleb already skipped on a dare. That’s not fair!” Leo pouted.

“Get over it,” Miles shrugged, “It’s me up next anyway!”

“Oh yeah, good point,” Leo said with a manic grin.

“But for this to work, ALL the stuff you record you gotta send to me to save where you can’t just… use it whenever you want it!” Miles said sternly.

Leo suddenly blushed. Caleb and Kai both noticed but stayed silent, slightly surprised when Leo quietly agreed.

Several minutes, and a quick password selection later, Miles had the accounts set up and that was it, the arrangement was made, and the game had changed. Feeling a significant sense of trepidation, Miles announced he was ready to take the next dare. “Just remember,” he said as Leo reached into the bag to pull it out for him, “We can’t be going out anywhere. If I miss dad’s deliveries, he’ll be bitching about it for weeks!”

“Yeah yeah, whatever,” Leo huffed. Miles was such a little suck-up sometimes. He was as badly behaved as the rest of them but just did a much better job of hiding it. His sucking up was cringey to watch, but he couldn’t deny it worked as Miles’ parents, as well as Caleb’s and the twins’ parents, all thought he was such a ‘good boy’. Puke! “Oh,” Leo said, a grin spreading virtually from ear to ear as he pulled out the dare and read it, “You… you said you need to be in for the deliveries, right?”

“Yeah, why?” Miles asked, already regretting ever suggestion to enforce compliance with the dares.

“Look,” Leo said, showing the paper to Caleb.

“Fuckin’ perfect! Get the camera ready for that one!” Caleb guffawed.

“What? What?” Miles demanded, lunging at Leo to try and grab the dare.

Leo kept Miles at bay, holding the paper up in the air as he teased for a few more seconds before announcing, “Answer the door in just your underwear!”

“Well… shit,” Miles said dejectedly.

“Wait, so if he’s GOT to do it, then… that means we HAVE to make it harder for Kai, right?” Caleb asked, getting a nod from the others and a groan from Kai. “So let’s not wait for Miles to do it before we pick the shit for him to do. You never know, they could turn up around the same time. I’d HATE for Kai to miss out on a full dare just because we’re unprepared!”

“Oh, thank you, you’re so considerate!” Kai said flatly. He huffed at the laughter it got, then said, “Guess I’m first as always, so…”

“No!” Leo interrupted, shaking his head. “For a change, why don’t YOU go last so you can’t just take the easy way out!”

“Oh yeah, so easy,” Kai grumbled, “Go on then!”

“Cay, you go,” Leo suggested.

“Sorry Kai,” Caleb shrugged, “You probably guessed, but… answer the door… naked!”

“How original!” Kai said flatly.

Miles laughed, though he still looked anxious about his own dare. It may not have been as bad as Kai’s, but for a body-conscious boy, it weas still pretty intimidating. “Umm… how about…” he paused, humming thoughtfully for a moment, “You gotta be hard too!”

“Ugh laaaaame,” Leo heckled, “It’s Kai. He’ll probably be boned up anyway, but hey, you wanna waste your turn, you do you!”

“Oh, so what’s YOUR genius idea?” Miles asked grumpily.

“He has to be stroking when he answers the door,” Leo said confidently, “And ask the delivery person if they wanna see him cum, and if they say yes… cum in front of them!”

All of the other three stared at Leo wide-eyed for a moment before Miles conceded shakily, “Okay, yeah… that’s actually pretty genius!”

“Thanks,” Leo said with a smirk, “And that just leaves Kai. What’s it to be, little bro?”

“Don’t fucking call me that!” Kai snapped angrily, then shrugged and said bitterly, “Fuck, I dunno, what’s left? Asking the guy to fuck me right there on the doorstep?” As he saw the others staring in shock, he waved his hands and said, “Not my actual suggestion!” As the others stared on expectantly, he thought about what he had already been ordered to do.

Getting naked in front of a stranger he would run past on the street was tough, but actually standing there naked in front of a delivery person… that was an entirely different kind of exposure. On top of that, actually being hard AND masturbating too. It was insane, but the thought of offering to let them watch was… annoyingly exciting. Yet again, it was a horrific dare that he was absolutely loving. Feeling his cock throb as he considered it, he shrugged and said, “I dunno, how about I have to do that for the next… five times I answer the door?”

“That’s literally five times harder,” Miles said with a nod.

“Wow, I can see why you’re the brains of this operation!” Caleb said sarcastically.

“Fine, that’s it then. Miles is answering the door in his undies, then the next five are all Kai!” Leo said excitedly. “Are you dad’s deliveries coming from the same place or could we get Kai’s first one done this afternoon too?”

“I… don’t know actually, I’ll message him and ask,” Miles said, feeling slightly less awkward about his own dare now that he knew how bad Kai’s was.

*****

“Oh my god, oh my god, it’s here!” Caleb said, almost bouncing with excitement as they saw the delivery van pull up at the end of the driveway.

“Sweet!” Leo said happily. “Come on Miles, down to your underpanties!” he teased.

“And it seemed like such a good idea at the time,” Miles sighed to Kai as he quickly stripped off. Even being near naked in front of his friends felt awkward.

“Hnnh, looks like he’s enjoying it!” Caleb smirked at the bulge in Miles’ underwear.

As Miles blushed, Kai just smirked a little to himself. He knew Miles wasn’t aroused, he was just a little more hung than the others and the bulge was just from his flaccid dick. It was funny to think that the only way Miles could disagree with Caleb’s assertion was to talk about his own penis size, and there was no way that was happening. He was already bright red just from stripping near-naked. He was only wearing as little as he had at the pool the previous day but somehow being seen in just underwear in his own home felt more exposing.

“Here he comes,” Kai said as he peered discretely out the window at the approaching worker. He felt a slight twinge of jealousy as the driver was a very attractive young man. He felt his own cock swelling as much from the sight of Miles’ humiliation as it was from imagining himself jerking off for the stranger.

The doorbell rang and Miles let out a whimper of mild despair, then headed out into the hallway as the other three gathered in the doorway to watch. Miles approached the door, sighed again and pulled it open. He managed to mostly conceal himself behind it.

“Yeah, you’re not doing that!” Leo whispered, nodding at the way Miles was hiding.

“Shocking,” Kai said despondently, getting a gentle titter from Caleb.

“Hi,” the driver said with a smile as he looked at the obviously-shirtless boy behind the door. He immediately clocked the other three and smirked, catching on to at least a vague idea of what was happening.

“Hi,” Miles said awkwardly.

“Can I take your name please,” the driver stated, taking a step back.

“Oh, umm… Miles. Miles Beston!” Miles said timidly.

“Great, here you go,” the driver said as he held a small box, but remained far enough back that Miles couldn’t reach it without stepping out from behind the door. The young man smirked as he looked the blushing boy up and down – his bare legs with their hint of ginger fuzz around the shins and smooth chunky thighs emerging from his tight boxers which clung to his bulging package. Miles’ top half was concealed slightly by his arms, but not enough to hide him fully, exposing his thick, smooth stomach and slightly chunky chest. The driver grabbed his phone as he held onto the box with one hand and said, “Sorry, just gotta take a picture to prove it was handed to someone at the property. Lots of thefts going on lately, so they’re really strict on it!”

“Oh, umm… oh… umm…” Miles stuttered as he heard sniggering from behind him.

“Don’t worry,” the driver said, grinning at the laughing boys down the hallway, “We don’t get your face in it!”

“Sure, cos the face is the embarrassing part,” Miles mumbled as the man took the picture, getting a snigger in response.

“Thanks, have a great day!” the driver said as he turned to walk away, laughing as the door slammed.

“Oh my god, that was horrible!” Miles said, as he put the box down and rushed past the others to get his clothes back on.

“You went so red!” Caleb commented.

“He was totally checking you out!” Kai said with an eager nod, still a little jealous as he hid the bulge in his shorts.

“Mate, total cringe!” Leo said, shaking his head.

“Yeah, well whatever. Knowing what Kai’s doing for the next one made it easier,” Miles said, smiling as he saw the grin drop from Kai’s face. “And considering what’s in the dare bag, I reckon you two are gonna deal with worse shit than that!” he added, wiping the smiles off Leo and Caleb’s faces too. “Oh, and look at that,” Miles said as he finished dressing and pulled his phone from his pocket, “Dad just said he got a notification to say the other delivery’s only eight stops away. Kai… I think it’s time to get ready!”

“Fuck!” Kai grunted as the others started cheering for his next humiliating dare.