Work Header

What Matters Most

Work Text:

Daring stumbled into his and Humphrey's apartment and slammed the door shut. He popped the button on his jeans and pulled the zipper down as he collapsed to his knees. He groaned as the thick butt plug lodged in his ass jostled against his overstimulated prostate. He pushed the rough denim fabric and his boxers down to his thighs, and finally wrapped his fingers around his aching cock. 

He tugged it fast and fierce, leaning forward and using his free hand to brace himself on the floor. He needed to come. 


Daring barely heard Humphrey approaching over the blood rushing in his ears. He knew the moment the man spotted him spread doggy style in the entrance way, though.

There was no missing Humphrey’s boisterous laugh.

“Look at you,” he teased. “You need relief so bad you couldn’t even make it five more steps to the bathroom to jerk yourself off.” He chuckled. “And you thought winning the bet would be so easy.” 

Daring lifted his head, too far gone to care that Humphrey had a front row seat to his impromptu show. Humphrey gazed at him, a goofy smirk on his face. Daring filled out nicely since they’d started college three years earlier. 

He had the look of a sports model. Tall height, lean muscles, and a nice, round ass. Humphrey was pretty much his opposite, standing five inches shorter and sporting the thin physique of someone who didn’t possess an ounce of athleticism. His own ass was nothing compared to Daring's, and although it was small, it was good enough, but that was the only positive thing able to be said about his behind.

In all words short, Humphrey looked like the art major that he was. 

The two of them were an odd pair. That was the thing about longtime best friends, though. It doesn’t matter how different they end up looking after their grown up, the bond that forms from spending almost every waking moment of their childhoods together is not one that can be easily broken. And they become immune to feeling awkward around each other, no matter the situation. 

Even Daring bent in half, jacking himself in the hallway, desperate for release, wouldn’t make things weird between him and Humphrey. They’d probably just laugh it off when it was all over. Daring didn’t feel a single ounce of embarrassment. All he felt was the need to blow his load, best friend watching or not. 

He had spent the last hour and a half awkwardly sitting through a history lecture, aroused and leaking continuously into his boxers. And it was all Humphrey’s fault. Well, it was a little bit of Daring’s fault. After all, he was the one that took the bet. It was a stupid bet. 

During a Sunday football game, they were both on the couch, having a random conversation that led them to talking about a plethora of things, including their prostates. When discussing it, Humphrey told him about how sensitive his was, and Daring eventually admitted that his seemed to be dead. He’d had hookups play with it before, but it had done very little for him. Humphrey had argued with him on the topic, swearing Daring just hadn’t had the right stimulation. And somehow he ended up accepting a bet that he couldn’t sit through a lecture with a butt plug in and not end up needing to get his rocks off by the end of it. 

Daring figured there was no way he could lose, especially since he’d chosen his history lecture as the one he’d sit through for the bet. He thought for sure his monotonous old professor droning on about the wars of a foreign country would keep his dick limp no matter what he had crammed in his rear end.

Man was Daring wrong.

He hadn’t considered that Humphrey would select a thick, textured plug for him, nor had he remembered his tendency to fidget when he was bored. As suspected, class had drug on. It seemed every other second Daring had subconsciously shifted to cross and uncross his legs, tap his foot, or resituate his upper body. Every slight movement had the bumpy toy rubbing against his prostate, and Daring had seriously underestimated the effect of repeated attention on that tiny little hot button. 

Turns out, his prostate was responsive. 

Forty minutes into class, Daring’s boxers had grown so damp that a stain had formed on the front of his pants. It was a wonder he hadn’t shot into his jeans untouched by the end of the lecture. Pure willpower was the only reason why. 

He had a record to uphold. In the twenty-one years that he and Humphrey had been friends, Daring had never lost a bet to him. By the end of class he still had a little hope that his record would hold, but any chance he thought he had left was completely dashed on his walk home. His cock had pulsed in time with each footfall, threatening to erupt as his steps rocked the plug in a pleasurable way. 

At one point Daring had even considered ducking behind a bush to take care of his problem. After that thought he spent the rest of the distance chanting reasons why getting a ticket for public indecency would be a bad thing. The closer he got to home, the more he struggled. And by the time he made it back, Daring couldn’t hold out any longer. There was absolutely no way he’d be able to get his dick to deflate without coming. 

So that’s how he’d ended up wanking his goods just inside the entrance to their apartment. His winning streak was about to come to a screaming end. Humphrey’s mouth spread into a wide grin. “Is Never-Lose-A-Bet-Daring finally about to lose his first bet? I never thought I’d see this day.” 

Daring’s mouth hung open as he sucked in air. He dropped his head down, his blond locks falling over his sweaty forehead as his hand flew up and down his shaft. 

So close

Humphrey leaned close to his ear and whispered, “Do you concede?” 

“Yes,” Daring squeaked out. “I need to come so bad.” On the last word the plug in his ass jolted forward against his sweet spot as Humphrey smacked the end of it. Daring cried out as long ropes of sticky white cum erupted from the head of his cock, painting the wood-textured living room floor beneath him. 

He squeezed his eyes shut as he rode the peak of his orgasm, and once he stroked himself dry, he flopped onto the refreshingly cool floor, sated at last. He reached back, removed the plug, and tossed it to the side. The loud plink of it dropping against the ground was the note of finality to his show. Daring cracked his eyes open and looked up at Humphrey. He watched Daring for a couple of seconds, sporting a content grin, proud of what he had just accomplished with making the bet. 

“I give you five out of five stars.” He beamed as he turned away. “Go get cleaned up. I’ll make you some tacos. No doubt you’re hungry after that performance.” All of Daring's bones seemed to have turned to mush, and he couldn’t imagine trying to stand upright in the near future.

Sometime around 3:00 in the morning, Humphrey woke up in Daring’s bed, wrapped in his arms. It wasn’t an uncommon occurrence. Humphrey tended to sleepwalk a lot, and anytime that happened, he somehow ended up there. If his sleepwalking bothered Daring, he never let on that it did. He always teased Humphrey about it in the morning, and even admitted once that it was nice cuddling with someone every once in a while, but he never got mad about it. 

Humphrey stretched his legs, fighting the urge to snuggle deeper against the heat of Daring’s body. It would be so easy to give in and pretend for a few minutes that he and Daring hadn’t come with the agreement years earlier to never hook up with one another, even though they were both gay and cared for each other. Shortly after puberty, Daring had come up with the idea, fearing a relationship might someday ruin their great friendship if it didn’t work out. 

Humphrey had stupidly nodded along, even though he couldn’t imagine a romantic relationship between them not working out. He still felt that way. Humphrey would bide his time for now, though. He’d give Daring space to date other people, to sleep with as many guys as he wanted to (not that he slept around that much), to get it out of his system. Humphrey knew Daring was it for him, that they were meant to be together forever. He just wanted Daring to come to the same conclusion on his own. 

Preferably sooner rather than later. 

Humphrey shifted away from Daring, but was halted when he unexpectedly tightened his grip around Humphrey’s waist and pulled him back to his chest. 

That was a first

Normally Daring let him slip out. He waited a few more seconds, until Daring’s arms loosened again, then he slid from under them. As he climbed off the bed, Humphrey heard a whisper. He turned back toward Daring, who appeared to still be asleep. 

“Did you say something?” he asked in a quiet voice. If Humphrey hadn’t leaned in and placed his ear close to Daring’s mouth, he might have missed his quiet one-word reply. 

“Stay.” Humphrey had never heard him talk in his sleep before, so the chances were Daring was awake and aware of what he’d said. 

People say a lot of things they don’t mean when they’re half asleep, he thought to himself.

Humphrey should've probably acted like he didn’t hear Daring’s soft plea, and go back to his own room, respecting their pact. The temptation was just too great to discard it like nothing. Plus, Daring liked to cuddle, and who was Humphrey to deny the man that. 

Whether it was the right or wrong decision, Humphrey crawled back onto the bed. He wormed his way into Daring’s warm embrace, resting his head over his beating heart. He tugged the covers up to his neck and relaxed into the cozy little cocoon created by Daring and the blanket. Daring probably wouldn’t remember what he’d requested in the morning, and if that was the case, so be it. 

For now, Humphrey would enjoy being wanted and held by his best friend. As always, it was a dream come true, and he’d live in it as long as Daring let him. 

The next morning carried on as usual for a Saturday. Humphrey and Daring ate bowls of cereal in front of the TV while chatting about their plans for the weekend, which consisted of both of them going to the Spring Party on the main campus. There was no mention of the conversation that occurred between them in the dark hours, just the normal laughing about Humphrey’s sleepwalking. 

After showering, they headed over to the college. Loud pop music blared over the grounds, where more than two dozen sections had been cordoned off for various events and activities. As Humphrey scanned the area, Daring grabbed his hand and tugged him in the opposite direction. “Let’s go over there. I think I saw Chase and Alistair.” 

As they strolled over, Daring didn’t release his hold on Humphrey. He shook his head, trying to make sense of it. It wasn’t the touching that had him confused. After all, they’d spent the night cuddling. Daring just wasn’t usually one to show affection in public. Humphrey opted not to draw attention to it. Pointing it out would probably lead to Daring breaking the contact and playing it off. He stretched to the right, looking around some people in front of them.

“Hey guys,” Chase said, pushing some of his hair away from his face his and strutting toward them. Alistair waved. Daring looked to the line forming at the sumo wrestling tent and motioned toward it with his thumb. “Do you all want to try that before the line gets long?”

Chase pumped his fist in the air. “Heck yeah.” He slung his arm over Daring’s shoulders, pulling him ahead of Humphrey and Alistair, and breaking him and Humphrey's connection. 

Humphrey exhaled sharply as Alistair elbowed him in the side. “So, are you guys finally a couple now?” he whispered, one eyebrow arched high. 

He shook his head. “No.”

Alistair smirked. “You do realize that friends don’t usually hold hands for that long, right?” 

Humphrey shrugged. “Yes, but you and Chase flirt more than any couple I know and you’re not together. So maybe it doesn’t mean anything.”

Humphrey frowned.

Alistair shifted his attention to Chase, his shoulders sagging. 

“It’s different with us, though.” He seemed to get lost in his mind for a few seconds, before shaking his head and re-pasting a smile back on his face. Alistair turned toward Humphrey and bumped his upper arm. “Nice attempt to change the subject there.” 

Humphrey chuckled and gave Alistair a half-smile, making a mental note to ask him what was up with him and Chase when he wasn’t around. “Listen, I don’t know what’s going on with Daring. Do me a favor and don’t point it out to him, though, okay?” 

The corners of Humphrey’s mouth turned down. “I want us to be more, but I don’t want to pressure him.” 

Alistair nodded. “Of course, man.”

He gave Humphrey a side hug. “Don’t worry, though. It’s obvious that he’s attracted to you. Everyone can see it.” While it was nice to hear from his friend, the words didn’t reassure Humphrey. Only Daring admitting his feelings to him could do that. 

The rest of the afternoon continued in the same odd way. As the four of them explored the festival, Daring often snagged and held Humphrey’s hand as they moved around. Even now, as they said goodbye to Chase and Alistair, Daring’s fingers were still twined with Humphrey’s. Daring gave Humphrey a tired smile, his forehead a little pink from spending the day in the sun. 

“Want to head back to the house, order a pizza, and chill?” 

Humphrey nodded. “Sure, that sounds good,” he mumbled. He lifted their joined hands and stared at them. He thought he could pretend it wasn’t weird. He’d tried. But after it went on all day he couldn’t ignore the obvious anymore. 

“Daring,” he whispered, his heart pounding. “What’s this about?” 

Daring let go, their arms dropping down to their sides. Humphrey’s heart sank. Daring opened his mouth, closed it, and opened it again. He let out a heavy sigh, his shoulders falling.

“Can we talk about it at home?” 

Humphrey looked to the left, where a bright red cardinal sat in a nearby tree. He took a calming breath before returning his attention to Daring. “Yes, okay,” he said in a gentle tone. For the first time ever, tension filled the air around them as they walked in silence back to the apartment. 


An hour later nerves had gotten the best of Humphrey. He’d barely been able to choke down one slice of pizza as he waited for Daring to open up. He hated this. Enough was enough. Humphrey picked up the remote and turned the TV off, leaving them in a deafening silence. Daring turned to face him, love and worry at war in his eyes. Humphrey gave him a small, encouraging smile, then said in a soft voice, “I can’t take this anymore.” 

Daring gazed back at him for a few moments, before nodding and taking a deep breath. “The pact we made…can we…”

Humphrey’s brow furrowed. He waited, allowing Daring time to get his thoughts in order.

“It’s just…” he cringed.

Humphrey reached out, placing his hand on Daring’s thigh. 

“Just say what you need to, Daring. It’s okay.” He rubbed his thumb back and forth in a soothing motion. “We’ve never held anything back before, so don’t start now.” Daring let out a nervous laugh and sat up taller, his back as straight as a steel rod. He looked down at his leg where Humphrey’s hand rested, and covered it with his own. Their eyes met. 

“Can we cancel our pact? I don’t want to stand around wanting you anymore,” he added. “I love you, and I want to be with you…as more than a friend. I want everything with you. I have for quite some time now truthfully.” 

Humphrey’s pulse accelerated as reality hit him. It was really happening! Daring wanted him, and he didn’t have to wait until they were old and gray for him to admit it. 

“I can’t imagine my life without you,” Daring continued. “And I believe that we’ll be good as a couple. We pretty much already are one.” He shrugged, one side of his mouth pulling up into a cheeky smirk. “I mean…how many other friends can laugh about a butt plug incident the way we did?” 

Humphrey burst with laughter. “Not many I’d imagine.” 

“So…” Daring drew the word out, one eyebrow arched high. Humphrey’s mouth stretched into a wide grin. 

“I’m sorry. I thought it was obvious,” Humphrey said, taking hold of Daring’s jaw. “I want that too. I want everything with you.” He closed the gap between them and pressed his lips to Daring’s. 

“I love you," he whispered to Humphrey. 

Daring wrapped his arms around his waist and tugged him onto his lap. Humphrey shifted until he straddled Daring’s thighs. He moaned as their mouths found each other again, and their jean-clad cocks brushed against one another. Daring slipped his hands under Humphrey’s shirt, his fingers clenching.

“I want to be inside you so bad,” he admitted with a groan. Humphrey nodded his agreement. He hopped up and stripped his clothes off in record time. Daring laughed while hurrying to remove his own. He pulled a condom and lube out of the nearby end table. It was convenient of them to have stashed supplies in various places throughout their apartment. 

Humphrey climbed back onto Daring’s lap after Daring rolled the condom on himself, then opened the lube, and squirted a generous amount onto his fingers. Humphrey wrapped his arms around Daring’s neck, tilted his head, and captured his lips again. 

He rose up on his knees, giving Daring room to press one finger, then two, into his ass. Humphrey worked himself on Daring’s digits as he moved them in a scissor motion. He had let out a startled moan once they had hit his prostate. Apparently, his best friend had magic fingers. 

No other man had ever made Humphrey feel this way. 

Their kiss grew sloppy as Humphrey panted into Daring’s mouth, lost in the sensation of his best friend touching him intimately. Daring removed his fingers, and placed the head of his cock at Humphrey’s entrance. He pushed through the tight ring of muscle easily. 

Humphrey leaned back and held Daring’s gaze as he lowered himself all the way to the base of his shaft, until Daring’s balls rested against his ass. He held his hips in a vice grip, his fingers digging into Humphrey’s flesh. He let out a deep moan as Humphrey lifted up until only the tip remained inside him, then brought himself all the way back down again. He increased the pace with each rotation, working himself faster and faster on Daring’s thick cock, until they were both left panting out loudly. 

Daring thrusted his pelvis up, pounding into Humphrey, driving them closer to the edge. Humphrey’s head fell back and his mouth dropped open as he pushed his hips forward and found the position that had the end of Daring’s rod hammering his prostate each time it moved past it. Daring grunted, his motions growing erratic. “I-I’m going to come,” he said in a harsh breath. 

Humphrey rode Daring’s cock like a professional jockey, chasing his orgasm. He was so close, could feel it beginning. His body locked up, his toes curdled, his eyes shut, and he let out a high-pitched cry and came all over Daring’s chiseled chest. 

When Humphrey reopened his eyes, it was just in time to watch Daring fall apart as he shot his balls dry inside Humphrey. When Daring was finally empty, he sagged back against the couch, pulling Humphrey with him. Their gasping breaths filled the air. As his heart rate slowly returned to a normal rhythm, Humphrey relaxed against Daring. Daring hugged him, pressed a soft kiss to his temple, and said, “I love you.” 

“I love you too,” Humphrey mumbled against Daring’s shoulder. 

He chuckled, then a few moments later, spoke again, tentatively, “Hey Humphrey…” 


“How do you feel about marriage?” His voice lilted up at the end. Humphrey sat upright, shock renewing his energy. 

“To you?” Daring nodded. 

Humphrey’s eyes popped open wide. “Are you proposing right now?” 

Daring’s eyebrows rose and he shook his head. “No, not now. I just wanted to know if you were open to the idea of marriage. Because I want that with you…but if you don’t want it, that’s okay. We can just be together.” Humphrey’s mouth broke into a full grin, his teeth shining. 

“Yes, I like the idea of that.” He brushed his lips over Daring’s. He ran his hand over Humphrey’s back, his smile widened. 

“Good.” He tugged Humphrey down so that he lay draped over Daring's body again. A few seconds later, he added in a small, hopeful voice, “And kids?” Humphrey pressed his lips to Daring’s heart. 

“Yes, all of it, Daring. I meant it earlier when I said I wanted everything with you. You make life worth living.” It was the truth. Humphrey couldn’t imagine his life without Daring. He wanted to marry the man, wake up every day next to him, raise kids with him, be there for him in the hard times, and laugh with him through the fun times. 

No matter where life led them, Humphrey knew they’d be just fine, because they had each other.