Daring Kai - Part 21 (Patreon)

The boys had spent the evening watching movies (not scary ones this time, despite Miles’s suggestions) before splitting off into the usual two rooms. Miles and Leo had squabbled the usual amount before heading off to Leo’s room, as Kai and Caleb settled into Kai’s room.

Leo hadn’t attempted to secure Kai to his bed or put in the vibrating butt plug. It wasn’t clear whether he had assumed Caleb would do it, whether he had chosen to give Kai the night off or whether he had simply forgotten about it, but Kai didn’t question it. It did feel a little strange. Being unrestrained was fine, it actually allowed him to get comfortable, but being without the plug he felt strangely empty.

Unable to get to sleep, Kai tossed and turned a lot, struggling to figure out what the problem was. He nearly went to retrieve the plug, but the more he thought about it, the more he figured it was not the cause of his sleeplessness. He clearly had… other things on his mind.

It had certainly been one hell of a day. Playing a game in public that had left him naked and exposed for so many people to see, thinking he was going to get arrested, seeing Caleb’s cunt of a brother again, being naked barely more than an arms-length away from his parents without them knowing, cumming while eating dinner and then being recorded sucking on his brother’s foot. It felt like the game had escalated really quickly and he wasn’t sure how he felt about it.

It was the game in Market Square that seemed to be bothering him the most. He knew he had been photographed, and doubtlessly videoed too. While he was exploring his own exposure through Instagram, that was under his control. He got to choose what he shared, he got to see the reactions, he got to read the comments (both good and bad). With the public incident, that control was completely absent. He had no idea who had footage of it, he had no idea if they would share it, he didn’t know if he would be identified. It was scary… and annoyingly also exciting. The mix of fear and arousal was always a strange one as it made him feel uncomfortable, but also desperate to cum.

Forcing himself to think about anything other than masturbating, his mind cast forward slightly and he found himself replaying what had followed the square – the escape! He had just run for it, and it had been downright terrifying. The naked part was bad enough, but as he replayed the few minutes over in his head it was the fact he was alone that had made it so difficult. In everything else he had done, the others had been there right beside him. Admittedly, they were usually there to make it worse, but still… they were there and he knew every one of them would protect him. For the naked run, he had been completely isolated, alone, solitary. He shuddered slightly and involuntarily whimpered, “Caleb!”

“Yeah?” the voice came from across the room.

Kai sighed softly. He hadn’t even meant to call for the other boy, and certainly didn’t think he’d still be awake. He knew he could pretend he was actually asleep, or just say it was nothing, but… he didn’t want to! At the same time, he also didn’t want to just come out and say what was bothering him. Instead, he was stuck in the middle, remaining silent and still.

“Kai, you okay?” Caleb asked when the other boy didn’t reply.

Kai still didn’t… or couldn’t… answer. He heard Caleb climb out of bed and pace across the room until he was standing over him.

“Kai?” Caleb enquired softly as he clicked on the lamp. As he saw Kai staring back at him thoughtfully, he remained silent and sat down onto the floor, leaning his back against the bed. After a few more silent moments he said, “Today was a lot, huh!”

Kai nodded, but realised Caleb couldn’t see it from where he was sitting, now facing back across the room. He shuffled round and put his feet on the wall as he let his head hang off the side of the bed, next to Caleb’s. “Yeah,” he replied quietly.

“Was it… too much?” Caleb asked gingerly, giving the upside-down head beside him a quick shot of side-eye.

Kai sighed deeply and replied, “I don’t know. Maybe.”

“I can imagine,” Caleb said with a nod. As he heard a gentle scoff from beside him, he quickly added, “I mean… obviously I don’t know how YOU feel, I just mean… even on my side of it, it was a lot!” Kai didn’t reply, but did tilt his head so he was looking at Caleb, who pursed his lips for a moment before he went on, “When we ran, and then I looked back and realised you weren’t with me, that was… I didn’t like that, especially when the others called and said they’d lost you too! It was… kinda scary just being on that side of it, so… yeah, I know your side was even harder! That’s all I meant!”

“You were worried about me?” Kai asked, managing a meek smile.

“Well… yeah, obviously,” Caleb replied with a casual shrug. Glad that the low lighting where he was sitting concealed much of his blushing, he quickly moved on with, “Not as worried as Leo. I swear, when he found out you wasn’t with any of us, he lost his fuckin’ mind.” He thought for a moment and asked, “I wonder what life’d be like if Leo ACTUALLY showed how much he cares about you or Miles!”

“Or you!” Kai added. He knew his brother was seemingly incapable of showing how he actually felt, but Kai knew him, and even though he fought with Caleb a lot, he knew they were almost as close as Kai was with Miles.

“If you say so,” Caleb said with a dismissive shrug, then went on, “So maybe we should avoid any dares that are quite so… big and public! That’s assuming you even wanna keep playing?”

“Fuck yeah,” Kai said with unexpected enthusiasm. As Caleb turned and grinned at him, he grinned back and said, “Yeah, I don’t know why I’m so into it either but… I dunno, it kinda feels like I’m learning stuff about me and what I like, and… and getting to know you guys better and meeting new people and doing new things. I know a lot of it’s… pretty freakin’ embarrassing, but… it’s kinda fun too!”

“Weird, but… understandable,” Caleb nodded.

“Ugh, I’m getting dizzy,” Kai groaned as he pulled himself back up onto the bed. “Come up here with me,” he requested as he could no longer see the other boy.

“Okay,” Caleb replied as he turned and climbed up onto the bed as Kai shifted across to make room. Both remained silent and still for a few moments, seemingly thinking the same thing but cautious about saying it. Caleb eventually broke as he raised an arm and asked, “Cuddle?”

“Fuck yes!” Kai said, with much more deliberate enthusiasm this time. He moved to rest his head on Caleb’s shoulder as the arm draped down around him. “Sorry, wasn’t sure if this was, like… still allowed,” he explained, then added a slightly unnecessary, “Y’know… cos of Ellie!”

“Oh, she’d be okay with this!” Caleb nodded as a broad smile spread from ear to ear. “She actually really liked that I was… I guess… cuddly. She said I was different from other guys, so… thanks for kinda starting me off on it!”

Kai felt a twinge of bitterness at being thanked for helping Caleb start his relationship, but managed a gentle chuckle as he said, “You’re welcome!” Thinking for a moment, he asked, “Wait, so why would that make you think she’d be okay with you hugging other people?”

“Oh, I… mentioned you,” Caleb explained, “And… that we… kinda started doing this and she thought it was so cool that we were, like… good enough friends to do this kinda thing. Not gonna lie, she also said it was kinda hot to imagine too!”

“Oh!” Kai replied, unsure how to react to all of that. Eventually he managed a curt but honest, “She sounds cool!”

“She is!” Caleb said happily. “So cool, and funny, and smart, and pretty and… honestly… fucking amazing tits!” Caleb explained.

“Good to know,” Kai replied, not wanting to state his honest reaction. Keen to change the subject, he looked up at Caleb a little and said, “You haven’t said much about your holiday… or Kieran. I was kinda hoping he’d… I dunno, grown up or whatever but today…” He stopped, shaking his head.

Caleb took a deep breath in, then exhaled shakily before he replied, “I hate him!” He felt his arm involuntarily tighten around Kai as he continued, “I just… I hate him SO much. He’s just… horrible ALL the time and… and nobody else seems to see it except you guys!”

“I’m sorry, I know it’s hard for you,” Kai said, reaching his hand up to gently stroke Caleb’s stomach. The skin was warm and soft, the hair of his treasure trail tickling Kai’s hand gently. As erotic as it could have been, the gesture was made purely platonically, and seemed to be received in that same manner.

“Yeah,” Caleb said sadly. “Earlier, when… when I was at home, he said…” Caleb trailed off, shaking his head.

Kai stared silently, still gently rubbing Caleb’s stomach.

“He said it was a good thing he’s here as it means Gran gets to see at least one… decent grandson before she dies!” Caleb explained, pausing briefly midway, carefully considering his wording.

“Fuck! What a cunt!” Kai baulked. He leaned over and draped himself over Caleb’s chest, gripping onto him tightly as he said, “I’m so sorry you had to hear that. That’s just… wrong!”

“Yeah, it didn’t feel great,” Caleb understated it as he wrapped both arms around Kai and just held him for several quiet moments.

“So you’re gran, this is definitely it then?” Kai asked cautiously.

“Hmm,” Caleb hummed, nodding gently, “It could be hours, days, might be weeks but that’s about as good as it gets. She’s not coming back from this!”

“That really sucks,” Kai sighed, getting a nod of agreement back. As the conversation seemed to have reached a natural end with Caleb not adding anything further, Kai smiled and said, “Maybe you should take a picture of this and send it to Ellie!”

Caleb laughed and gave Kai a squeeze before nudging him off to the side. “Maybe,” he said, though it was clearly an amused no. “Hey, umm… is it… okay if I stay here?” he asked coyly.

“Oh, you mean because it’s SUCH a long walk back over there!” Kai sniggered as he looked over to the other bed, though he noticed Caleb wasn’t laughing.

“No, I mean… staying here, at your place, just until Kieran goes back to Uni,” Caleb said shyly, cheeks slightly flushed.

“Oh,” Kai said as he propped himself up on one elbow, already nodding, “Yeah, sure, you know you can always stay here!”

“I really hate him,” Caleb sighed.

Kai ventured coquettish smile as he said, “Hey, if it means more time for you here, I fuckin’ love him!”

“Oh my god, shut up,” Caleb laughed grabbing Kai in a grasp that was half affectionate hug and half wrestling move.

Kai closed his eyes for a moment to enjoy the feeling of Caleb’s body pressed against his own, making no attempt to get free. “You really do give the best hugs,” he mewed softly.

“Yeah, turns out you were right in that video you did,” Caleb smirked, grinning even more as he pulled back and saw Kai blushing at the reminder of the dare and subsequent video sharing. “Oh, yeah, that reminds me, what did Luca say about HIS video?” he asked curiously, “I’ve been meaning to ask!”

Kai sat up, pouting as he said, “Nothing. Not even a reply or a joke or anything. He read the message, he got the video and then… nothing!”

“You… seem unhappy about that!” Caleb said, looking slightly confused as he raised a hand to place behind his head.

Kai tried in vain to avoid letting his gaze roam to the small tuft of hair in Caleb’s pit. He wanted to reach out and touch it, but managed to resist going that far. He blushed as he realised how obvious he had been in his staring and answered, “I… guess I am. If he’d reacted and been all, like… ‘haha, look at you, that’s so lame’ I’d have been embarrassed but understood. Same if he’d said, like, ‘wow, nice, you’re hot’, that’d be cool, but… getting nothing at all is just… rude!”

“Maybe he thinks you like him!” Caleb said with a shrug, raising his other hand too so both were behind his head now. He saw Kai staring again and cleared his throat to prompt a reply.

“Like him? Why would he… think that?” Kai asked, trying to remain focused as the shirtless boy with the exposed armpits and pert nipples and nice pecs and sexy stomach and beautiful face laid stretched out beside him.

“Well… you literally sent him a video of yourself knocking one out while talking about his sexiest features, and… y’know, he’s out and everything so he knows you know he’s gay, so… maybe he thought that was you coming onto him!” Caleb reasoned.

“Oh, fuck,” Kai exclaimed, “I never thought of that. So maybe he’s not replied cos he doesn’t wanna hurt my feelings!”

“Why would he be hurting your feelings?” Caleb asked curiously, “If he’s got any sense, he’d be just as into you as he probably thinks you are into him!”

Kai blushed profusely at the comment. Imagining Luca liking him was unusual enough, but the obvious compliment from Caleb really got his heart pounding… and his cock throbbing.

“Wow, maybe you DO like Luca,” Caleb said as he nodded towards the slight bulge growing in Kai’s underwear.

“I… I don’t know,” Kai said awkwardly as he lifted his leg to conceal his growing erection.

“You, umm… you gonna take care of that before we sleep?” Caleb asked, nodding towards the hidden boner. Looking a little embarrassed at what he had asked, or rather, the possible reason behind it, he added, “I just don’t want you poking me awake in the night!”

“Oh, well… I wasn’t planning on doing that. I’m not really allowed, remember!” Kai replied. In his peripheral vision, he noticed Caleb lifting a leg too. Was he also hiding an erection. It was worth a shot, so he asked, “Are you… taking care of yours?”

“No!” Caleb replied sharply, “I mean… I don’t… have one!”

“Put your leg down then,” Kai challenged him.

“No!” Caleb objected.

“Yes!” Kai replied, grabbing Caleb’s knee.

“No, get off!” Calen said, pulling his knee away, though he was smiling reluctantly as he did it.

“You’ve totally got a boner!” Kai teased.

“Yeah, well… so what if I have. It’s bedtime. It’s just… used to the routine!” Caleb explained. Cautiously he put his leg down, showing the sizeable bulge of his boner in his boxers.

Kai thought about Miles’s words from earlier in the day – you miss every shot you don’t take! He looked Caleb in the eye and said, “I still have the whole… daily blow job offer going, y’know!”

“Umm… I think… that may be where Ellie draws the line!” Caleb replied a little shakily, “Or… I guess I do. I… I… don’t wanna be a cheater!”

Kai nodded and gave a polite smile as he said, “Good, I’m glad to hear that. Cheating’s bad, sorry, I didn’t think!” He was more than a little downhearted to no longer be able to do anything with him.

“We could… just… jerk off together,” Caleb said with a very forced attempt to sound casual.

“I think that’d still be breaking the rules for me. I can only cum as part of a dare!” Kai explained as he laid back down.

“Okay,” Caleb said with a nod as he looked to his side, “Kai… I dare you to jerk off with me!”

“I don’t know if it works like that!” Kai said, before realising he really shouldn’t be objecting. He quickly covered over his own excuse as he added, “At least not without doing things to make it worse!”

“Fine, we jerk off together and… I cum on you!” Caleb said with surprising eagerness.

“And then I have to eat it!” Kai added, eyes wide at the prospect of consuming Caleb’s load.

“Yeah, perfect!” Caleb said, nodding happily for a moment before calming himself a little to say, “I mean, that’s… yeah, that’s nasty. You should… do that cos… cos it’s hard!”

“It’s not the only thing that’s hard!” Kai chuckled as he raised his hips off the bed and pushed his underwear down to mid-thigh, letting his erection spring free.

“Yeah, same here,” Caleb laughed, copying the move. Once again, he seemed to catch on to what he was doing and grow a little shy as he placed his hands over his boner and said, “We… we should… do the dare, right!”

Kai didn’t reply verbally, but the hand grasping at his rigid prick answered for him. Excited as he was, he didn’t jump straight to the rapid pumping that would have reflected his extreme arousal. Instead, he managed to contain himself and began a slow, gentle stroke as he stared intently at Caleb’s hands, waiting for him to join in.

Caleb’s hands massaged at his swollen prick and aching balls as he watched Kai masturbate. He didn’t dare raise his gaze to Kai’s face for fear of seeing where he was looking. Was he just staring down at his own dick? Was he staring at Caleb’s? Was he trying to look him in the eye? Or were his eyes closed, maybe? That would be the least embarrassing one, probably. But it would mean Caleb wouldn’t be able to see Kai’s eyes, his deep, beautiful, blue eyes… not that he had ever noticed them! Of course, having them closed wouldn’t exactly be awful either. He had seen Kai asleep many mornings, his eyes closed and his chest slowly rising and sinking, looking absolutely peaceful and angelic… not that he had ever noticed! Caleb’s left hand had pulled away as he considered the boy beside him, leaving his right to begin stroking. He barely even realised he had done it.

Caleb finally ventured a look to his left. Kai’s eyes were fixed squarely downwards, eyeing Caleb’s hand as it stroked up and down on his raging hard-on. Was it exciting to be watched by him, or awkward? It was a little hard to tell, but from the way his cock throbbed within his grip he could probably guess. Suddenly, Kai’s eyes flicked up and met Caleb’s. He met the gaze for the briefest of moments before tilting his head away to stare straight up at the ceiling as he masturbated.

The game continued for several minutes, each of them taking it in turns to look, prompting the other to look away as they both wanked eagerly. It was Kai who eventually broke the silence when he asked, “Where are you… gonna cum?”

“I… I hadn’t… thought,” Caleb replied. “I guess I’d just…” he paused to roll to the side, aiming his dick towards Kai’s stomach and continued, “… do it like that!”

“Cool, okay,” Kai nodded.

Caleb hesitated for a moment as an idea came to him. Before he even knew what he was doing, he had rolled onto his side, pushed himself up onto one knee and swung his other leg over Kai. Kneeling up, he found himself straddling the other boy’s legs. His dick was still grasped firmly in his hand, pumping away and mere centimetres from Kai’s. “Or like this!” he said, surprising himself as much as he did Kai.

“Fuck,” Kai gasped quietly as he stared at the large figure looming over him. Being able to look to the side and see Caleb’s dick in his hand had been exciting. Being able to just stare ahead and see all of him – his thick torso and pert nipples, his muscular arms, his beautiful face, his tantalising cock – it was almost too much for Kai to take. “Oh god, I’m gonna… cum soon,” he gasped.

Caleb nodded, beginning to pant slightly as he stared at the cute boy lying below him. “Me too I think,” he said shakily, unsure exactly what he was feeling.

“Fuck, fuck… ahh, yuss!” Kai gasped as he began to squirt his load over himself. The first shot hit the underside of his chin while the following spurts left long white streaks across his smooth, flat stomach and chest. Still panting from his own release, he stared intently at Caleb’s cock for a moment then let his gaze roam slowly upwards until his eyes met Caleb’s. Neither of them looked away this time, holding the stare for several seconds. As Kai heard a gentle whimper from Caleb, he nodded a little and gave a serene smile.

That seemed to be all Caleb needed to finish as he let out a low guttural growl and began to add his load to Kai’s, painting the prone boy’s torso with his load. He continued stroking until it reduced to a dribble that trickled down over his fingers and dripped onto Kai’s cock.

“I guess… I gotta eat it now!” Kai said, almost trembling. He reached down and scooped up a hefty glob of his own jizz mixed with Caleb’s, moved his hand above his mouth and let it drip in for a moment before slipping the fingers into his mouth to lick them clean.

Caleb watched intently as Kai repeated the process several times, slowly cleaning most of the goo from his body. His own hand remained gripped tightly onto his softening prick.

“Nearly done,” Kai said nervously as he reached down and grasped at Caleb’s wrist. Pulling the hand away from his dick, Kai stared up at Caleb and asked barely louder than a whisper, “Can I?”

Caleb was breathing rapidly, with shallow quick breaths as he nodded and then watched his fingers disappear into Kai’s mouth. His eyes fluttered closed for a moment and he let out an unintentional groan as he felt Kai’s tongue lapping the spunk from his fingers. A few moments later, it was like a bubble had burst and reality had kicked in. He pulled his hand away and span back round to lie next to Kai again. He stayed motionless for a brief moment before he sat up a little, as if to leave, and started, “I should…”

“Don’t!” Kai pleaded, grabbing at Caleb’s shoulder. It felt like the night before Caleb went away, when he had run away from their intimate moment.

“D… don’t… what?” Caleb asked anxiously.

“Just… don’t,” Kai replied, then added a breathy, “Please!”

“Okay,” Caleb replied, nodding as he laid back down and clicked the lamp off.

Glad Caleb was staying, but cautious not to scare him off again, Kai rolled over to get comfortable, being careful not to touch the boy behind him and make it awkward. A few moments later, he heard movement. At first he was worried Caleb had decided to move back to the other bed anyway, but then he felt the warmth of a body against his back, followed by an arm snaking its way under his neck, while another looped over him to meet it. Before he knew it, he was spooning with Caleb.

Neither of them said anything, and they barely had time to even enjoy the feeling as they had both drifted off to sleep within moments.