Chapter Nine
Riley licked his lips as he watched Brent drop his jeans and underwear, peeling off his t-shirt slowly, almost as though he knew how much of a tease this was for his best friend. It had been a long time since they’d seen each other completely naked—not since they were children.
Puberty had been kind to Brent. Well, no, puberty itself had been a misery for both of them, like it was for most people. But it had left behind a beautiful man with square shoulders, just enough muscle tone to look strong but still cuddly…
… and a really nice cock.
Riley tried not to stare, but he was always a little weak in the presence of beautiful people. Sometimes he forgot how beautiful Brent was, because he knew him so well.
It was hard to forget right now.
“Wow,” Riley said softly.
“That’s not something I hear a lot,” Brent mumbled, blushing all the way down to his collar bones.
“You should hear it every time you’re naked.” Riley paused, considering that. “Every time you’re naked in front of someone who isn’t a medical professional, anyway.”
“It would kinda freak me out coming from a doctor,” Brent agreed.
Riley stood, already naked, and closed the gap between them, leaning in to kiss Brent softly. Their bellies brushed together, the lightest touch of Brent’s cock against his own sending a shiver down Riley’s spine.
Brent was so beautiful, and Riley had wanted this for so long. He would never have asked, never have even mentioned it, but he wasn’t going to miss the opportunity.
Besides, it would make Brent feel better. Riley could make him feel loved, and wanted, and sexy, all things that he needed to feel right now.
“You’ve never done this before, have you?” Riley asked softly.
Brent shook his head, his expression sheepish.
A tiny thrill of arousal somersaulted in Riley’s gut. He didn’t necessarily have a thing for virgins, but the thought of Brent’s first time with a man was exciting.
“That’s okay. We’ll take it as slow as you need,” Riley promised, reaching out to brush his fingertips against the soft, delicate skin of Brent’s belly.
His cock was already starting to react, the length swelling, the head getting dark. Riley could have stared at him all day, basked in the knowledge that Brent was aroused by the thought of sex with him.
Staring all day wouldn’t get them any further, though, and this was about Brent. This was about what Brent wanted.
“Be honest, does it hurt?” Brent asked.
Riley made a soft, sympathetic noise. “No, but I’m not gonna let you worry about that. I expected to bottom.”
Relief washed over Brent’s features. Riley wanted to kiss him again, promise him that he didn’t have to be nervous, that all of this was okay and not actually scary at all, but he wasn’t sure how affectionate he was allowed to be.
He was probably already pushing it.
“Okay.” Brent nodded. “Good. I mean… good, if that’s what you want?”
Riley laughed, touched by Brent’s concern. “Trust me, it’s what I want. You don’t need to worry about me.”
“I spend half my life worrying about you,” Brent murmured. “I’m not gonna stop now.”
Riley swallowed. That felt a little too real, a little too intimate for comfort.
He worried about Brent all the time, too, but hearing Brent say it…
Riley was trying so hard not to give this any more weight than it was supposed to have, but Brent was a sweetheart. It should have been obvious that he’d be just as sweet as a lover as he was as a friend.
He scooted back on the bed, leaving Brent plenty of room to join him.
“How do you want me?” Riley asked, spreading himself out.
Brent blushed all the way down to his collarbones. “I, uh…” He paused to scratch the back of his neck. “However, umm… whatever would make you most comfortable.”
Riley chuckled, crawling up the bed and laying himself out in the middle of it, shoving a pillow under his hips and raising one knee to give Brent plenty of access. “This work for you?”
“Yeah,” Brent said, his voice cracking. “That works.”
“Lube in the top drawer,” Riley said, nodding to the nightstand.
He didn’t need to dwell on how cute Brent was being, how his stomach clenched at the thought that he wanted this. Wanted Riley.
How long had Riley wished for that? It felt like forever.
“There’s, uh… there’s an assortment of lube, here,” Brent said, his voice unsure.
“Pick one that says it’s for anal,” Riley responded. “I mean, obviously. It probably doesn’t matter after that.”
“Self-warming, or extra sensitive?”
Riley licked his lips. “Extra sensitive,” he said. He wanted to feel as much of this as he could, and the warming would only get in the way of that.
“Condoms?” Brent asked, extracting a box from the drawer.
Riley hesitated a moment, then shook his head. “I don’t have anything you could catch, and I get tested all the time. If you’re comfortable going without…”
“I got tested recently,” Brent said. “And you know I would have already told you if there was anything, but it’s up to you.”
“Don’t worry about it,” Riley said, excitement making his stomach feel tight.
He’d never, ever gone without a condom before, not with anyone, but Brent was different. This might have been his only chance to feel Brent inside him, and he wanted it all.
Brent closed the drawer, moving back to the bed, the mattress dipping as he climbed on it. Riley spread his legs wide, suddenly aware of how exposed he was. With someone else, he might have felt vulnerable. Nervous, even.
Not with Brent. He trusted Brent with anything.
Riley watched as Brent poured lube onto his fingers with more confidence than he’d been expecting.
“You look like you know what you’re doing,” Riley said, raising an eyebrow. That was a surprise.
“I know how anal sex works,” Brent said, blushing darkly. “I’ve just never actually done it.”
“Is this the part where you confess you learned everything you know from porn?” Riley asked.
Brent cleared his throat. “Something like that. You want one finger or two to start with?”
Riley grinned, lifting his hips up just a little. “Two. I’d like you to fuck me some time this century,” he teased.
This might have meant a lot to him, but it was still Brent. If they couldn’t be friends while they were having sex, then what was the point?
Riley gasped as he felt Brent’s fingers pressing against him, the lube still cold in contrast to the heat of his body. Apparently, Brent didn’t need to be told twice.
Brent pushed his fingers inside before Riley could say anything else, leaving him moaning breathlessly as the pressure knocked the air out of his lungs. Brent’s fingers were thick and strong, making Riley squirm as they moved inside him, stretched him wide.
It’d been way too long since he did this, his muscles protesting at being forced to stretch in a way they weren’t used to right now. Riley squirmed against Brent’s hand as he got over the initial ache of being stretched, his stomach bottoming out as discomfort gave way to pleasure, every sensitive nerve ending he had firing at once.
It was like riding a bike. Riley had never forgotten how to relax and go with it, his body responding exactly as he’d hoped it would once it started to warm up.
He’d been half-hard before, but he could feel his cock straining now, curving up toward his belly button, blood rushing to fill it up. He felt hot and tight, his thighs tensing up with the urge to rock back onto Brent’s fingers.
“You’re, uh… you’re very responsive,” Brent said. “That’s kinda…”
“Hot?” Riley offered.
“Intense,” Brent responded.
“Good intense?” Riley arched his back, giving Brent the opportunity to slide his fingers in further and moaning low and needy as he did. Brent felt so good. So much better than he’d imagined.
“Yeah.” Brent swallowed so hard that Riley could hear it without even needing to look up at him. “It’s… I wasn’t expecting…”
“Tell me,” Riley encouraged, wanting Brent to feel comfortable with him. If he couldn’t give Brent anything else, he could give him that.
“I wasn’t expecting to really get off on this,” Brent admitted softly. “I was expecting it to be comforting, but not… not like this.”
Riley bit down on his lip, barely suppressing a whimper. He knew he needed to be responsible right now, protect Brent’s heart as well as his own, but this was all his Christmases coming at once.
“Do you need to slow down?” Riley asked, his voice rough with arousal.
“No,” Brent swallowed again. “I just… I wanted you to know.”
“You’re so sweet.” Riley chuckled. “It’s okay that you’re enjoying yourself. You’re supposed to. It’s okay if we have really great sex, I promise.”
Brent huffed, slipping a third finger inside Riley, stretching him wider. The burn didn’t last as long this time, the fullness of Brent’s fingers overriding everything else. Riley’s cock twitched as Brent stroked his insides, as his balls caught on Brent’s wrist and rolled back and forth with the motion of his hand.
“I dunno about great sex. I don’t think I’m that good.”
“I think you are,” Riley said. “But I’m a little biased.”
“You’ve also got most of my hand in your ass,” Brent pointed out. “So you gotta be nice to me.”
Riley laughed, rocking back against Brent’s fingers. He’d always hoped it’d be like this between them. A little intense, but mostly fun and easy. Awkward in the perfect way that could only happen between friends. Real, lifelong friends.
“Ready for more?” Brent murmured, twisting his fingers inside Riley like a pro. He’d always been a fast learner, and he was clearly enjoying the way Riley gasped and writhed against his hand, rocking his hips, right on the edge of begging.
“I thought you’d never ask,” Riley panted, his lungs tight. He could have laid there and let Brent stretch him all night, except that he really, really wanted Brent’s cock.
He hadn’t forgotten how gorgeous it was. How thick and beautifully curved, perfect for this. His balls ached at the thought of it, the knowledge of how it’d fill him up, of how satisfying it was going to be.
“You could’ve asked first,” Brent pointed out.
Riley shook his head. “No, this is for you. Whatever you want. I’m here to make you feel better.”
Brent paused, reaching out to touch Riley’s knee with his free hand. “But… you’re enjoying it, right? Because I really don’t want to use you.”
Riley made a soft, sympathetic noise and lifted his hand to place it on top of Brent’s. “Look at me for a second and tell me if I’m enjoying it.”
Brent did look at him, his gaze roving down from Riley’s face, over his flushed, heaving chest, down to where his cock was achingly hard and dripping precome on his stomach. He swallowed, his Adam’s apple bobbing in his throat.
“I never noticed how pretty you are before,” Brent said softly.
Riley bit his lip, committing that to memory. He’d always have that. He’d always have this one time, and yeah, he was enjoying it.
“I’m definitely enjoying it now that you’re breaking out the compliments.” Riley grinned. “Come on. You’re a beautiful man, and I like you. Of course I’m enjoying it.”
“Beautiful?” Brent asked, so much cautious hope in his eyes.
Riley wished he could call him beautiful all the time. Brent clearly needed to hear it more often.
“Yes,” Riley said. He couldn’t bring himself to turn it into a joke, though that might have been easier for both of them.
“But I’m-”
Riley reached out, pressing a finger to Brent’s lips. “Unless you were about to say perfect, I don’t wanna hear it.”
Brent opened his mouth to object, even with Riley’s finger in the way, but then sighed instead.
“You’re a good friend,” he said the moment Riley moved his finger away.
“You can thank me by fucking me. Soon. Please.”
“And a demanding friend,” Brent said, but he was smiling.
This was so nice that Riley could barely believe it was happening. He’d always felt close to Brent, but this was a level of closeness they rarely got to share. This was so much more than Riley was used to having with him, and it was making him greedy for more.
This still wasn’t about him, though, so he clamped down on the feeling and shoved it aside. This was about Brent feeling loved and wanted, and Riley intended to give all that to him and take nothing in return.
Well, nothing except a really good orgasm.
Brent shifted his position, grabbing another pillow to shove under Riley’s hips, lifting him up higher. He barely needed Riley’s cooperation to do it, easily able to push him around, hold his weight, move him however he wanted.
Arousal curled in Riley’s stomach again at the thought. Brent was more than capable of providing a really good orgasm. He was so strong, so much bigger and heavier than Riley was.
It was still blowing Riley’s mind that his awkward best friend had grown up to be this hot. Riley had always loved him, and he’d wanted sex with him for the closeness, the intimacy of it, but a bonus of waiting as long as they had was that Brent was extremely fuckable now, regardless of whether or not Riley had feelings for him.
“I’m dying of old age, here,” Riley said, spreading his legs wider.
“Are you always like this? How do you ever get anyone to have sex with you twice?” Brent asked, lining himself up, pressing the head of his cock against Riley, so close to where he wanted it.
“Generally, I don’t.” Riley grinned. “The ones who come back are special.”
Brent leaned forward, bracing one hand against Riley’s shoulder, his fingertips digging into the flesh there, hard enough to bruise. He took a few deep breaths, obviously psyching himself up, then closed his eyes and rocked his hips forward.
Riley bit down on his lip as Brent’s cock finally filled him, barely holding in an embarrassing moan. He shifted his legs a little further apart, the mattress creaking under the movement.
Brent felt amazing inside him, the lack of a condom making him feel bigger, hotter than he’d ever experienced before. He could feel the skin of Brent’s cock catching against him, just a little. He could almost tell himself that he could feel Brent’s pulse, feel the vein along the underside of his cock twitching as his heart beat, but he had to be imagining that.
Either way, he felt so good that Riley already knew nothing else would feel like this again.
Riley had always wondered whether it would be any different with him, whether his feelings for Brent would make sex better, or worse, or whether he’d really notice at all.
He did notice, and it was already better. Every touch of Brent’s fingers sent sparks bouncing over his skin, every soft sound of pleasure Brent made curled up in his chest to be kept and remembered later.
“I need a second,” Brent gritted out, his voice already rough. “I… you’re so…”
“Hot?” Riley offered, grinning to himself. He was determined to get Brent to admit he was hot.
He might have been a little over-emotional about this, but that wasn’t going to stop him teasing Brent mercilessly.
“Tight,” Brent corrected. “I had no idea.”
Riley laughed at that. Being Brent’s first man was nice, too. He’d always wanted that.
Really, this was perfect. It didn’t matter that it was a one-time deal, something they’d never do or speak of again. Riley was happier to have it once than not at all.
Brent rocked his hips experimentally, making Riley gasp as his cock dragged over a sensitive spot. There was no point in trying to be quiet about this, there was no way he could maintain it.
Besides, Brent deserved to know how hot he was, how good this felt, how much Riley was enjoying it. It wasn’t fair to pretend otherwise.
Riley focused on Brent’s fingertips pressing into his shoulder, the other hand pushing down on his hip, holding him in place, tiny anchor points keeping him grounded.
He wanted Brent closer, but he didn’t know how to ask. He wanted to dig his fingers into Brent’s back, meet every one of his thrusts, pant and moan into his ear, tug on his hair…
He wanted all of it. Everything Brent had to offer.
But this wasn’t about him.
“Ready when you are,” Riley prodded, eager to get Brent to move. His cock was leaking on his stomach, his thighs were tight, arousal coiled in his gut. The shape of Brent’s cock inside him was so perfect, so satisfying that it was taking all his willpower not to flip them over and ride Brent until he begged for mercy.
That wasn’t quite what Brent needed right now, though.
Brent’s fingers tensed on his shoulder as he gave his hips another tiny, experimental roll. Riley barely stopped himself from rocking back against him, meeting his thrust to spur him on, make him go harder and faster.
Brent needed time, and Riley knew that. He didn’t want this to be over too fast, but at the same time, he couldn’t wait for Brent to come inside him, his cock twitching, his breath coming in short, sharp pants.
Riley shifted the leg Brent had pulled over his hip earlier, using it to urge him closer. He groaned low in the back of his throat as Brent shifted, brushing a spot inside him that made stars explode behind Riley’s eyelids. The feeling made Riley squirm, spread his legs wider, shift his hips so he could have just a little more, arousal making his skin tingle, searing heat building deep in his stomach.
He didn’t remember closing his eyes, but he had to force them open again to look up at Brent’s face. His eyes were wide and dark, his cheeks flushed, lips parted softly.
Nothing Riley had ever imagined even came close to the real thing.
“Come here,” Riley said, reaching out to put his hand on Brent’s cheek, hoping he’d come closer.
The change in position bent Riley practically in two as he locked his ankles at the small of Brent’s back, but he hadn’t spent hours upon hours of his life practicing yoga for nothing. Sometimes, his quirks had other advantages.
No one really thought about it until they could do this to him without him complaining.
Brent didn’t seem to notice, too busy leaning closer to kiss Riley, sucking on his lower lip, biting down just enough for Riley to feel it. That made Riley rock his hips, rubbing his cock against Brent’s stomach and leaving a sticky trail in his wake.
Brent moved the hand that had been on Riley’s hip to the headboard, bracing himself against it and rocking his hips again, building an agonizingly slow rhythm between them, rocking Riley back and forth.
“You’re so gentle,” Riley said, unable to hide his delight. Of course Brent was gentle. Riley had always known he would be. “You don’t have to be.”
“Just warming you up.” Brent murmured, resting his forehead against Riley’s. “Unless you’re in a hurry?”
Riley chuckled. “I wanna come so bad,” he admitted. “But don’t speed up on my account.”
Brent hummed, rocking his hips just a little harder, grunting with the effort. Riley knew that if he wanted to be forceful, he wouldn’t have any trouble. Brent was a big guy, heavy and muscular.
Even though they were going slowly and carefully, Riley could feel his arousal building, the first tingling of an orgasm starting in his inner thighs, at the base of his spine.
He gasped as Brent shifted, the angle of his cock changing again, his hips rocking just a little faster. This wasn’t the frantic, needy sex he’d always imagined his first time with Brent would be, but it was wonderful.
The low, slow burn of arousal was making his skin feel tight, beads of sweat tickling as they rolled down the back of his neck.
“More,” Riley whined, not even sure himself what he was asking for. All he knew was that he wanted more of this, more of Brent, as much as he could get.
Brent sped up again, his thrusts making the mattress squeak under them, the wood of the bedframe straining. Riley was confident it would hold—he was confident it had seen worse. The sound was soothing, rhythmic, perfectly lined up with the sound of Brent’s harsh breaths, the way Riley’s pulse was pounding in his ears.
The urge to come started in the pit of Riley’s stomach, but he held it back, forcing himself to take a few deep breaths. He wasn’t ready yet. He needed so much more of Brent.
Riley wrapped his arms around Brent, dug his fingers deep into his back, his nails digging in. He’d leave scratches, and he knew it, and he wanted it. Wanted to leave a mark on Brent, some evidence that they’d done this, that they’d had this, even if it was only one time.
How was he supposed to give this up after one time? It felt so good, so right, like everything Riley had been waiting for all this time was coming true.
“Riley,” Brent panted in his ear. “Riley, I’m gonna…”
Riley nodded eagerly. He knew what Brent was about to say. He was ready to come, too, overwhelmed by how good this felt, how amazing it was to be this close to Brent, his cock catching on the soft skin of Brent’s belly as they rocked together.
He shoved his hand between them to help himself along, wanting to come as close as possible to Brent. Wanting to come while Brent was still inside him, still filling him up, making him feel complete in a way he’d never even known to look for before now.
“Come for me,” Riley whispered, moving his other hand down to Brent’s ass, squeezing it tight, pulling him in closer.
His own hips jerked, torn between thrusting into his hand and back onto Brent’s cock, so thick and hot and satisfying that Riley knew he’d be ruined for all other men after this. Nothing would ever compare.
No one else would ever be Brent.
Brent groaned a low, heartfelt groan that vibrated in Riley’s chest, his hips bucking as he started to come, his cock twitching inside Riley as his thrusts got harder, faster, more intense than they had been.
Riley bit down on his lip as the beginning of his orgasm hit him in the back of the neck, making his back arch as a jolt of pleasure ran down his spine and he fisted his cock, squeezing tightly as he felt himself coming, thick spurts coating the back of his hand.
He panted, screwing his eyes shut, his mouth falling open. A shout caught in his throat, coming out as a broken sound he wasn’t sure he’d ever made before as he stroked himself through waves of pleasure, taking advantage of the aftershocks until he was too sensitive, too completely exhausted to continue.
Riley hissed as he felt Brent slip out of him, wincing at the loss of his cock. He was too sensitive to really enjoy it now, but he missed it all the same.
Above him, Brent panted like he’d just run a marathon, his hair soaked with sweat, plastered over his forehead.
He was glowing. His face was flushed and relaxed, his eyelids heavy, his mouth slack.
Riley could have stared at him all day and never gotten tired of it.
All too soon, Brent heaved himself up and flopped down beside Riley on the bed, the mattress moving with him.
Before Riley could say anything, Brent groaned the most deeply satisfied groan he’d ever heard.
That made him grin. He clearly felt better after that, which had been the point.
As long as Brent was happy, Riley was happy. That was how it had always been.
“I hope you enjoyed that as much as I did,” Brent said, his voice already sleepy.
Riley grinned again, pleased that he’d worn Brent out. Especially because he was exhausted, too, and at risk of passing out on him at any moment.
“I did,” Riley said, stretching his legs out gingerly. “It’s been a while.”
“Couldn’t tell,” Brent murmured.
“Good.” Riley yawned widely. “Don’t freak out in the morning,” he said, closing his eyes.
Brent would definitely freak out in the morning, but hopefully not too much. Not more than he could handle, anyway.
“I won’t,” Brent promised. He probably believed it, too, but Riley knew him. Between them, he was the calm one.
“Night,” Riley slurred, his tongue refusing to cooperate as much as he would have liked.
Brent grunted in response, apparently just as close to sleep as Riley was.
As he felt the world slipping away, Riley reached out to touch Brent’s hand, smiling as he did so.