The Dare Box

Ryan and Jake were like brothers. Maybe even closer. Their whole lives fit together like two puzzle pieces.

Jake lived just north of the city in a sprawling ranch house in a forest with a view through the trees to the bay. His parents were rich, successful, and spent their summers running a resort in the Caribbean, so ever since he turned 18 Jake had been left alone with a credit card and the keys to a hand-me-down mercedes. Last summer, after they graduated high school, the boys spent almost every day swimming in Jake's pool, hosting parties around the backyard bonfire, and generally living it up as kings of their kingdom.

But it wasn't just Ryan leeching off Jake's good fortune. When Jake's parents returned in the winter and the house parties had to come to an end, it was Ryan's time to shine. He lived in a penthouse condo at the heart of the city. The private rooftop balcony was one of the highest around, so from the inset jacuzzi they could survey the city lights and not have anyone looking down on them. Ryan's parents were socialites (and probably swingers), and they were always sending late-night texts telling him they were staying over at a friend's house and to order in.

So as the boys settled into their second summer free of homework and teen drama, the first summer they were both 18, and they had built a pretty nice routine that had them swimming and sunning at Jake's through the days, playing video games and watching movies through the nights, and enjoying the city life trying to hook up with girls on the weekends before slipping back to Ryan's empty condo for a beer in the jacuzzi when they both struck out.

Life was pretty sweet.

So when they were laid back in the jacuzzi on a Friday night and Jake said, "I'm bored," it caught Ryan off guard.

"What?"

"I'm bored."

"You want to watch a show or something?" Ryan asked.

"No, I mean, this!" Jake gestured around him. "All this! We're just doing the same thing over and over and not doing anything real."

Ryan didn't get it.

"I just mean," Jake continued, "we're adults now, right?"

"I guess."

"But like, we're going to have to go to University soon, and get jobs, and get married and shit."

"You'll have to propose to me first."

Jake rolled his eyes. "You know what I mean."

"What's the rush, man? Are your parents on your case or something?"

"No, that's just it. They haven't told me to get a job or find a school or anything. They offered to bring me down to help out in the resort if I wanted--

"That's pretty sweet"

"Yeah, but I'd be down there for months and my mom said they basically have all the staff they need, so I'd just end up doing the same thing down there as I do here. At least here I can hang out with you."

"Awe, that's sweet. Maybe you really are going to propose?"

"You're telling me you aren't bored?"

"Bored of swimming and hanging out and chasing girls? No."

"But there's no challenge, no goals. At least in school we had homework or finals or something to work towards."

Ryan splashed his way across to his friend and put a damp hand on his forehead. "Are you feeling ok? Did I hear that right? Jake Porter is missing homework?"

Jake smacked the hand away and pushed Ryan back to hide his smirk. "Shut up."

Ryan stepped back and pulled himself out of the water to sit on the deck. He tugged the wet fabric of his blue shorts away from the six inch semi that lay along his left thigh. Something about the warm air and the hot water had kept his blood flowing.

Jake caught a glimpse of the round, circumcised head up the leg of Ryan's shorts and let his eyes slide up Ryan's smooth, tanned chest to the stars above the hazy lights of the city. His thoughts wandered and he adjusted himself under the steamy surface and covered it by stretching forward and then back and resting his hands behind his head.

The movement caught Ryan's eye and he looked his friend over, from his red shorts distorted beneath the water's surface to his hairless armpits - still shaved even though they weren't on the school swim team anymore.

On another rooftop a few blocks away was a large illuminated pool. The blue water stood out against a terracotta patio hosting a few dozen partiers. Jake could see half-naked bodies jumping in and out of the water and could imagine that he heard the splashes and laughter over the din of city traffic below.

"I've got an idea," he said, his hands still behind his head and his eyes on the pool.

"What's that?" Ryan asked, still looking over his friend's smooth skin.

"We put challenges for each other in a box and we draw them out one at a time. We don't do anything else until we accomplish it, and then the other person goes."

"What sort of challenges?"

"It could be anything--something like getting three girls number in one night, or I don't know--

"So just truth or dare?"

"Yeah, but not just that, like it could be more complicated too. Like, get into the private suite at the Cocktail Lounge. Then we have to figure out how to do it before we can pick another one."

Ryan had some idea of what his friend was getting at, but he hoped it wouldn't interrupt things too much. Despite what Jake said, Ryan was never bored with their hangouts.

"Ok," said Ryan, "so we just write a bunch of things on papers and put them in a box?"

"Yeah, you down?"

"Sure, but there's got to be stakes, right?"

"Like what?" Jake asked as he also lifted himself out of the water and sat on the edge, pulling the damp fabric away from his crotch.

"First person to fail on a challenge has to give up something. Not money, but like, how about if you fail a challenge you have to give me your car for a month."

"Oooh, I don't know about that."

"Scared you're going to lose?" Ryan taunted.

The boys were friends, but they were also highly competitive. All through their time on the swim team they competed over everything, and that just made them better. Either one of them could put down a challenge and know the other would never back down.

Jake thought it over and finally said, "Alright, but when you lose first you have to wash my car for a year. And no drive-throughs. I want to see you out on the driveway in a bikini with a bucket of soap."

Ryan laughed, "In a bikini?"

"Fine, a speedo. Enjoy January, numbnuts."

They both laughed and knew it was on.

Ten minutes later and the boys were dripping on the kitchen floor, still only wearing their shorts, standing on either side of the island counter with a pen, a stack of notecards, and a bottle of scotch passed between them as they wrote out their challenges for each other.

The first few ideas had come quickly, and pretty soon they had more than two dozen each and they folded them in half and tossed them in a pair of shoeboxes Ryan had pulled out of his closet. They each took a celebratory double shot to start things off and pushed their boxes of dares across to each other.

Ryan tossed the cards around and then propped open the lid to pull the first card. A coin flip had decided who would start.

Ryan unfolded the paper and read the challenge, and his eyebrows went up.

"What?" Jake asked.

Ryan read the card aloud, "Make a post and get a subscriber on OF.' Are you kidding me?"

Jake covered his face as he tried to hold back his laughter. "I can't believe you pulled that one first!"

Ryan tried to look mad, but he couldn't deny he was amused at the idea.

"So," said Jake as he composed himself, "You wanna back out already? My car is looking mighty dusty this week."

Ryan barely broke eye contact as he said, "You're on." He grabbed his phone and opened the app store. A minute later he showed Jake the blank profile of his new fan page.

"Done."

"No no, come on, you have to post something. The challenge is to get a subscriber. Anyone can just open an account."

"Alright fine," Ryan said and he handed his phone to Jake and took another shot of scotch, "but that means you have to be the camera boy."

"Camera man, you mean."

Ryan walked around to the living room side of the apartment and flipped on some lights. He stood against an empty part of the wall and did his best cover model pose.

Jake snapped a few shots, enjoying how loose Ryan was becoming as the drinks took effect. They stood together, bare shoulders rubbing, and scrolled through the pictures. Ryan chose his favourite and added it to the account as his profile and cover photo, which he had to admit were looking pretty good.

"So what's your post going to be?" Jake asked.

"Just those, right? We'll have to wait and see if someone signs up."

"No no, that's weak. You're not going to get anyone that way. And the challenge said, 'Make a post'."

"So, what, you want to film me jerking off or something?"

"It's your account man, I'm just the camera man."

"Ok, camera boy." Ryan grabbed the scotch off the counter and took a deep swig. Then, bottle still in hand, he hooked his thumbs in the waistband of his shorts and pushed them down.

As the shorts landed in a damp puddle around Ryan's bare feet, Jake had to admit that his buddy cut an impressive image. Slim legs with light hair led to a neat bush with a thick dick sitting at a low angle but getting higher. His dick was cut and had a bulbous head that made it look like the perfect mould for the classic dildo design. Ryan still had the flat abs and slim waist with a 'v' of muscle pointing at his dick like a big tan arrow. His chest was hairless and his skin was radiating the light heat of post-hot tub booze on a warm summer night.

"You just gonna stare, or are you gonna roll the camera?" Ryan held out the bottle of scotch and Jake shook his eyes off his friend's perfect body, took a swig of scotch and held up the phone.

Ryan grabbed his dick with the same right hand grip he'd always used: wrist on top, thumb pointing down with his fingers wrapped around between his dick and his belly, the underside of his cock nestled comfortably in the palm of his hand.

Jake almost forgot to press record.

Neither boy had ever thought gay thoughts before, except the normal glances for comparison in the pool showers, or the odd porn search when they were still learning the anatomy of sex. Despite all that they were both feeling more excited standing on either side of the camera than they had in dozens of one night stands and short-lived relationships.

"So that's how you hold it, huh?" Jake asked from behind the camera. He was using both hands to hold it steady because he didn't know if he could hold himself back from joining in otherwise.

"Yeah, but usually I'm laying down."

"You want to lay down? Why don't you use the counter?"

Ryan met his eyes, "You're director boy now?"

Jake smirked, "Get up on the counter, bitch."

Ryan pretended to be shocked but he hopped up on the counter, his swim shorts slipped off his feet and left him completely naked under Jake's gaze and the black lens of the phone. He twisted to the side and lay his legs on the counter top. It was just long enough that his feet dangled off one end and his head rested on the edge of the other. The cold marble sent a chill over his skin in the otherwise-warm evening.

Without even thinking about it Ryan rolled over onto his front, his left arm propping him up while his hips started to rock and his abs flexed as he started to slowly fuck his right hand.

"Holy shit," Jake said under his breath. He was suddenly flooded with regret that they hadn't found an excuse to jerk off in front of each other before. The idea of seeing his friend fuck his hand cut through the last of the pretense holding him back and Jake reached into his own shorts to adjust his hardon into a more comfortable vertical position.

Jake stepped closer and found himself circling Ryan as if he was a roman statue on display and Jake was there to capture all the angles. He stepped towards Ryan's legs and lost sight of his friend's flexing torso but gained an angle on his thrusting ass. Ryan's cheeks flexed with each push and Jake watched the trimmed hair on his balls lift and fall against the marble counter.

"I don't think I should cum," said Ryan suddenly, slowing his thrusts and then rolling back over to reveal his pulsing cock, the head glistening with lubricating precum.

Jake reluctantly stopped the recording and raised his eyes to meet Ryan's, "Why not?"

"Just a feeling. Gotta keep them wanting more, right?"

There seemed to be more going on behind Ryan's eyes, but Jake couldn't argue. The point was to get something to post so people would subscribe and the only reason to keep going until he shot his load was that Jake really fucking wanted to see it.

Ryan held out his hand and Jake handed over the phone and stepped up to the counter as Ryan swung his legs off and sat on the edge.

Jake watched from beside Ryan's bare shoulder, stealing glances at his friend's glistening cock while having thoughts that he had never had before.

Ryan watched his own performance with awe and had to hold himself back from touching his pulsing dick. He had never had these sorts of urges before, but from the moment he pulled down his shorts and saw Jake's eyes drop he had felt a thrilling sensation burning in his gut at the idea of being watched and lusted after. The ambitious corner of his brain had already rushed ahead to when he had hundreds of subscribers and he could post videos like this all the time. The money would just be a bonus. He quickly trimmed the ends off the video and uploaded it to the account as a free preview.

"Now we wait." Ryan turned to Jake and they were both suddenly very conscious of how close they were and how naked Ryan was. "I guess it's your turn."

"Huh?"

"The dares -- the challenges I mean. You should start one."

"Oh, right." Jake grabbed the box from where Ryan had pushed it aside and tried to let a thought in that wasn't about Ryan's naked body. He grabbed the first card and opened it up and read, "Suck a dick." He looked up to see Ryan smirk.

Jake swallowed involuntarily and some corner of his mind imagined what it would be like to swallow a load of cum instead. He had tried to suck his own dick a few times, but never been able to do more than make brief tongue contact. Once he'd shot far enough to hit himself in the face but he'd just wiped it away without thinking much of it.

"What are the odds of that?" Ryan said as he leaned back on the counter, resting his palms on the marble behind him and glancing down where his still-throbbing dick lay pointing at his chest.

Something about Ryan's tone caught Jake's ear and he looked back at the box in his hands. He pulled another card and read, "Suck a dick." Another one. "Suck a dick. What the fuck?"

Ryan shrugged. "I don't like to lose. Either I get your car, or I get a blowjob." Ryan's smirk was a grin now. They had been playing dirty in their competitions for years. This time was just a little more dirty than before.

"So you just flooded the box with 'suck a dick' so I'd have to forfeit?"

"You didn't say the challenges had to be all different. Checkmate, car keys please." Ryan held out his hand.

"So what would this mean?" Jake asked, his heartbeat throbbing in his ears and his shorts.

"Well, if you don't want to give up your car, I can help you complete the challenge." Ryan let his eyes dip to his pulsing hardon for a moment and then back to meet Jake's gaze.

A lot of unspoken things can be said between lifelong friends, and in that moment they were speaking volumes. Was this going to get out? Of course not, it would stay between them. Would it be a one time thing? Who knows? But there were plenty more cards that said, "suck a dick" so who was to say the game would end at one? And was this really going to happen?

"Ok," said Jake, his voice barely a whisper. But his eyes had dropped inevitably to the still-wet dick in front of him and without another word he slipped to his knees on the soft carpet, reached out to grasp the base of Ryan's cock, and slipped it all the way into his mouth in one gulp.

Ryan gasped. He had felt the conversation going the way it did same as Jake, but something about his best friend inhaling his hardon, still sensitive from his countertop performance, was unlike any dance club bathroom fumble he'd had with any girl. There was an instinct to how Jake wrapped his lips around his teeth and wrapped his tongue around Ryan's cockhead. The suction at the back of his throat on the way out and the texture of Jake's tongue on the way in was bringing him extremely close extremely fast.

"Holy shit, I'm going to cum soon," Ryan said. Jake didn't slow down. If anything, Ryan could feel the suction increasing as his friend rocked back and forth along the shaft even faster.

"Oh fuck!" Ryan closed his eyes and gripped the counter tighter. "Are you gonna?" He couldn't finish the thought as the most electric orgasm in his life pulsed from deep behind his balls and Ryan felt the gush of cum burst up his shaft and out.

Jake had pulled back just enough so the ridge of Ryan's cockhead rested on his lips as the jet of cum splashed against the roof of his mouth. He instinctively swallowed and the added suction only made the next squirt thicker.

Ryan's abs twitched as his hands left the counter and grabbed Jake's head. His friend had clearly decided to swallow so Ryan's primal urges took over and he held Jake's head in place as his sensitive cockhead twitched again with a third spurt.

Jake couldn't swallow everything and loosened his lip's seal on Ryan's cock. Cum spilled out and dripped down his bare chest to where his free hand was grasping at his own dick through his shorts.

As Ryan's orgasm slowed, he released his grip on Jake's head and opened his eyes. The sight of his half-naked friend with his cum dripping down his front felt like a core memory had been awakened. Ryan was definitely going to cash in more of the challenge notes if Jake was down for it. And he definitely seemed down for it.

Jake didn't back away from Ryan's dripping cock and let the last drops roll over his tongue as he reached down and desperately tugged his shorts out of the way. His uncut hardon popped into view and he barely needed to pump it twice before his own cum was hitting the base of the kitchen counter and dripping over Ryan's bare feet.

The boys were a sweaty mess in the warm summer air, and the light salty smell of cum added to the horny haze. They had just come and yet both were feeling their blood keep pumping into keeping their cocks hard. They could have gone for round two without stopping but some part of their brains that had been taught to feel guilty for sex started asking annoying questions and the boys found themselves pulling away from each other and glancing to meet each other's eyes.

Thankfully with the reality of their friendship, and all the things they could say without words, included being honest. And they could tell as their eyes met, the cum still dripping from their cockheads, that there was plenty more to do.

Jake looked around at the splashes of cum across Ryan's feet and the drips down his own naked chest. He looked up past his friend's still-chubbed cock and met Ryan's eyes.

"That was so gay," Jake said.

"That was so hot," Ryan replied.

Jake involuntarily licked the cum off his lips and had to smile, "Yeah it was."

"We're cool, right?" Ryan asked. He held out a hand to help Jake up.

Jake took his hand, squishing some more cum between their fingers. It really went everywhere, he thought. He let Ryan pull him to his feet and they stood, their dicks only inches apart, and their bare chests still breathing heavily.

"Yeah," said Jake, "I'm cool if you're cool."

"Oh, I'm cool alright."

"Cool."

Silence fell and they both looked around to get their heads back in reality. They both thought that it should be awkward and weird now that they had shot their loads, but they also both felt just as turned on as before.