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Their first attempt was- well, what's a word for ‘worse than an absolute disaster’?
"Okay, you're sure you're ready?"
"As ready as I'm going to be," Charlie answered, gritting his teeth.
"You don't look very... You know, we don't have to do this if you don't want to," Nick said, stroking himself absently.
"I know we don't have to but… well we've been over this hundreds of times. Three years of dating, and we've never even tried it."
"Never really felt the need," Nick quipped.
"Mhmm. Glad I spent half an hour prepping then," Charlie said, though nothing about his tone conveyed gladness.
"I just want to make sure. I don't want it to be unpleasant!" Nick said. He leaned down and worked his mouth along the inside of Charlie's thigh, unable to resist taking advantage of the easy access. Few, if any, of their other sexual encounters had resulted in Charlie flat on his back with his legs in the air, and even if nothing else about today went well, Nick was already thoroughly enjoying the view.
"Nick!" Charlie hissed, "We said not sexy! So…" He blushed, and looked away, "Y'know, less of…that."
"Less. But not none?" Nick teased, pressing kisses to Charlie's stomach, hovering just above where he actually wanted his mouth to be.
"Not none, but can we-" Charlie squirmed, trying to get away from Nick's tongue and the things it was doing to him. "Let's get on with it, shall we?"
Nick gave a tiny, pretend frown, but backed off. "I just don't want it to feel… clinical."
"What fucking doctors are you going to, sweetheart?" Charlie was grinning ear to ear now, well past the nerves he'd felt a moment ago. "I understand what you mean," he soothed, "I would just feel safer if we both figure out our general level of interest before we're like… desperately horny. I want to be able to ease into it. Hence the-" he gestured to the rag that they'd used to clean up earlier and thanked the gods for his boyfriend's basically non-existent refractory period.
Nick nodded, then stood and positioned himself at Charlie's entrance, adding an extra swipe of lube to both of them for good measure. "Righto, so I'll just-"
"Nick?"
"Mmm?" Nick paused, his cock just making contact with Charlie's hole, but not pressing in yet.
Charlie grimaced, not only because of the unfamiliar sensation. "...Did you just say 'righto' before the first time you're ever going to put your cock in my arse?"
"I… did."
"I rather wish you hadn't."
"I rather wish I hadn't as well."
"Well good, we agree. Do you want to try–" Charlie suggested, but by then it was hopeless. Nick had started to laugh, and the sight of him standing there, fully hard and cackling, set Charlie off as well. Soon they were both doubled over with laughter, Nick leaning on the bed frame for support as he wiped tears from his eyes, his erection long gone.
"Oh god, why are we like this?"
"I have no idea, but if we ever try this again, you get to be on your back next time," Charlie sassed.
The next time they tried it, Nick was on his back, as promised. Despite the "not sexy" rule being in play again, this attempt inherently felt a bit sexier. Without Nick's superpower of a short refractory period, Charlie had planned to sacrifice an erection to the experiment, although, as he stroked himself just enough to stay hard, he secretly hoped it wouldn't be a complete waste. Between exams and Nick's busy rugby schedule, they hadn't had much time lately for intimacy, and he'd reached the point where his level of need was starting to outweigh his reservations.
"Hi," he said, lining himself up with Nick's hole. He grazed a lubed finger over the puckered, pink flesh, and Nick shivered.
"Hi. Are you ready for this?"
"Feel like I should be asking you that," Charlie mused, pressing forward tentatively. Slow. Easy. You're just trying it, he reminded himself.
"I'm ready. I trust you, Char. Let's give it a go."
At that confirmation, Charlie took a deep breath and pressed in earnest into Nick's arse. Immediately it was warm, and tight. Maybe too tight? Though he was glad just to have some kind of contact after two weeks of hiatus.
Nick remained stoic for the first press, but at the second he winced. "Wait, wait, wait." He tried to catch his breath, to focus on anything other than the uncomfortable sting.
"Nick, are you okay? Shit, I'll pull out."
"Don't!" Nick insisted. "Besides, you're barely even in," he said, managing a short laugh. He was right, Charlie had only just barely gotten the tip in so far.
"Does it… hurt?" Charlie asked, concerned. He wiped his hand on the rumpled duvet, suddenly aware that his fingers were still slick with lube.
"I mean, you're not small, so… um. It's definitely noticeable. I think you can go a bit more though." When Charlie hesitated, Nick said, "Look, we're never going to know if we don't try. It doesn't hurt, just feels weird." It was mostly the truth.
With a deep breath and a few prayers, Charlie cautiously pressed in another inch. Part of him immediately felt the tightening in his gut that usually preceded orgasm, then another much more urgent part could only focus on the sensation of tightness directly on his cock. Which, he could now conclusively say, was too tight; almost vice-like.
"How're you feeling, babe?" Charlie asked, soothing his hand along the back of Nick's thigh and pretending not to notice the crease of discomfort on his brow.
"It's… I'm okay. It's not bad, or good necessarily. Just really odd. I think… if you wait just a sec you can probably go all the way in?"
Charlie nodded and licked his lips. He inhaled slowly, one, two, three , then on the next exhale pressed all the way in.
He and Nick made eye contact and nearly started laughing all over again.
"Not good or bad, just… odd," Charlie confirmed, scrunching up his face. "Is it doing anything for you?"
"Somehow it got way less uncomfortable when you did that. I'd be curious to see what it feels like if you moved a bit?"
Charlie nodded but didn't answer out loud. He shifted his hips to pull out slightly then thrust back in as gently as he could manage, and Nick yelped.
"Noooope, I take it back. Oh my god, that feels so weird."
"Bad weird?" Charlie asked, trying to make sense of what he was feeling. On the one hand, it was genuinely unpleasantly tight. On the other hand, it felt like he might come at any moment, despite what could only accurately be described as mild pain.
"Ah… I can't say it's good weird." Nick answered, shifting slightly on the bed in an attempt to find any position that might alleviate the uncomfortable feeling of pressure. "How about you?"
"It's… I feel like I'm going to come?" Charlie said, more a question than a statement.
"Oh! Oh, well that's…" Nick tried to push himself back against his boyfriend, and moved a hand to play across Charlie's bare stomach, setting aside his own discomfort. "That's good, babe. Yeah, I want you to come for me."
"No, like…" Charlie winced as Nick tensed around him. "Sorry, can I pull out, please?"
"Oh, um, yeah. Yeah, of course." Charlie started to slide out and Nick caught his arm. "Just… go slow, okay?"
Charlie nodded and pulled back inch by inch until he was finally free. A sense of relief washed over him, and at the same time, the sense of impending orgasm immediately dissipated. He watched as a wave of relief seemed to spread across Nick’s entire body.
It felt like a ridiculous statement to make, but Nick made it anyway. "You, um… you aren't… coming."
"Yeah, I appear not to be," Charlie answered, squinting down at himself. "Sorry, that was the strangest feeling."
"You don't have to tell me," Nick said, eyes wide. “I was there.”
"No honestly, I'm sure it felt incredibly odd for you too, but for me-" Charlie flopped down onto the mattress next to Nick and started some of the basic, gentle aftercare they'd read about. "It felt like… well first things first, you're way too tight. Good lord."
"It felt that way for me too, so I can only imagine how it was on your end. You think I just wasn't relaxed enough?"
"I'm sure that's part of it." Charlie frowned and pressed a kiss to Nick's forehead. "You didn't do anything wrong, though."
Nick nodded shyly. "Do you think… you would have liked it more if I'd been more relaxed?" He did a poor job of concealing the self-conscious edge to his voice.
Charlie kissed his forehead again, almost insistently. "I think if you like it, I could learn to like it. But if you don’t, I’m not really keen." He ran a hand through Nick's bangs lovingly.
Nick gave a soft little shake of his head. "To be honest, I didn't like it very much." He took Charlie's hand and held it to his chest, carefully examining each finger. "I'm still confused by… you said you were going to come."
"Oh. No, I said I felt like I was going to come. But it wasn't, um… d’you ever have those times where you're stroking off, and you've only just started, and you're not even properly hard yet, but you get that twinge anyway? And it's, y'know, totally out of place? That's what it felt like."
"Mmmm," Nick said, his attention still focused on Charlie's thin fingers. "So… did it feel weird enough that you don’t want to get off anymore?” he asked, casually.
“Oh, um,” Charlie blushed, suddenly feeling exposed. “I might have to kiss a bit first and build back up to it, but,” his face went redder and he took his hand back to cover his embarrassment, “to be honest I’ve been going a bit mad without you.”
“Yeah, I can tell.”
Charlie raised an eyebrow, then followed Nick’s gaze down to his cock, which was still fully erect and throbbing needily. “Ah, yeah, I…” he swallowed hard and tried to find the right words, to say something appropriately sexy, but Nick saved him the trouble by reaching down to wrap a hand around him, stroking confidently. There was still enough lube left that the slide of his fingers made Charlie’s toes curl.
“Is that it, then?" Charlie barely choked out, as Nick began to stroke him properly. "Are we just writing that off?”
“I think,” Nick paused, and Charlie whimpered. “Oh, sorry.” He resumed stroking and said, “I think we should give it one more go. You bottoming again, if you’re up for it. We didn’t actually try that last time. And then, if we don’t like it after that… honestly I’m okay writing it off for good. Deal?”
Charlie nodded and tried to answer, but Nick chose that moment to twist his fingers gracefully, and all Charlie could manage was a low moan instead.
So, at least the experiment hadn't been a complete waste, then.
Their third, and final, attempt was over almost before it started.
This time they agreed that they should strive for “medium sexy,” reasoning that a degree of arousal might loosen them up. Which is to say that Charlie had already come down Nick’s throat and was feeling quite satisfied, but Nick hadn’t gotten off yet. Charlie still insisted that they maintain a level of detachment. “I just don’t want you… getting ahead of yourself,” he said, nervously eyeing his boyfriend’s girthy cock.
“I’ll be really gentle Char, I promise. I’ve got this. We’ve got this,” Nick reassured him. “We don’t even have to do this though, seriously.” He ran his fingers up and down his cock lightly, trying to maintain the balance between keeping himself hard and getting overly excited. If he was being honest, Charlie looked fucking delicious like this. It wasn’t anything about his arsehole particularly, but this level of exposure and openness was doing something for Nick that he made a mental note to explore more thoroughly at a later date.
Charlie smiled up at him. “No, I… I do honestly want to know. We found out that we’re not particularly into me topping, so maybe we’ll enjoy the reverse? It’s worth a try, yeah?”
“Yeah,” Nick agreed, nodding. He reached for Charlie’s hand and laced their pinky fingers together. “Third time’s the charm, eh?”
“God let’s hope so!”
With that, Nick wordlessly applied a generous amount of lube and lined himself up at Charlie’s entrance. “Okay. You’re sure you’re ready?”
“I’m ready,” Charlie answered without hesitation.
This time Nick felt anticipation and anxiety, rather than just anxiety alone. When Charlie nodded, he pressed in the first inch or so, waiting as they both got accustomed to the feeling. It was warm, and tight, though Nick noted it didn’t rival Charlie’s mouth on either count. With his boyfriend’s verbal approval he pushed in another inch, trying to ignore the mounting pressure building in his core. He also tried to avoid looking down at Charlie, spread open and ready for him in a way that made him feel dizzy.
Charlie, for his part, found it less unpleasant than the opposite position had been. He felt like he could take ‘odd’ off the table, and leave it at ‘neither good nor bad.’ “This is… kind of okay, right?” he said, pleasantly surprised. “I don’t necessarily love it, but I don’t dislike it either.”
He looked up at Nick, whose face was just shy of panicked.
“Nick?”
Despite the condom, which Charlie had suggested might dull the sensation a bit, Nick was immediately past the point of no return. “Charlie, I… fuck. Ohhhh fuck.” He furrowed his brow and dug his fingers into Charlie’s thighs, trying to hold back, but it was useless. Still only halfway into his boyfriend’s arse, he tensed and then, against his better efforts, he was coming, the sensation washing over him dully as he cursed under his breath.
“Damn it,” he moaned, trying to fight back the waves of disappointment and shame. With Charlie’s hand on his arm, both soothing him and guiding him, he pulled out slowly, then removed the condom and tossed it into the bin.
“Nick?” Charlie said, perplexed. It had seemed to be a somewhat successful attempt, from his point of view. "You came! Was it not good?"
"It was okay."
"Nick, babe. You came like… immediately. You're telling me that was just 'okay'?"
Nick considered his answer for a minute as he settled on the bed next to Charlie and snuggled against his chest. He didn’t want to sound sour, but the experience had been more or less all of his worst-case scenarios for sex.
He and Charlie had spent years finding creative ways to help him prolong sexual encounters so he could enjoy them, and he’d come to expect and enjoy a bit of nuance. Some teasing here, complex and interesting sensations there, holding out long enough to get a proper, full-body orgasm rather than just a little blip.
He could already tell that with anal, it would only ever be him absolutely powerless to hold back, and getting the briefest, most basic pleasure out of it. The physical sensation had been disappointing, and the emotional side of it had felt downright degrading. Unless it was something Charlie needed to try a fourth time, he hoped they could agree not to repeat it.
Nick worked the words around in his head, trying to soften the blow. "Okay so… you know that thing you do with your fingers? The little twist?"
Oh, he's caught on to that trick, Charlie thought to himself with a smirk. “Yes, I’m familiar,” he answered.
“Right, well. Your arsehole doesn’t know that one.”
Charlie choked on a laugh, but tried to compose himself. It was a serious topic, after all. “Ah. I see,” he said, as evenly as he could.
“And that move you do with your tongue? Right below the tip? Yeah, your arse can’t do that either.”
“Oi, are we discussing all my trade secrets here?”
Nick laughed and pressed a kiss to his boyfriend’s cheek. “Sorry love, I take it back. You’ve been fucking my brains out for three years, but I have no idea what it feels like or how you do it. And I definitely don’t use the same tricks on you.”
Charlie blushed, then frowned, then practically scowled. “Do you really think…” He averted his eyes. “Do you think what we do is actually… fucking?”
Finally, one of them had said it out loud. After three years of intense, sensual, passionate, blindingly pleasurable, and entirely non-penetrative sex.
Nick sighed, letting the question hang in the air for a beat. Then he reached over and tipped Charlie’s chin toward him, forcing him to make eye contact. “I think… you make me come really hard, all the time,” he said, sweetly, brushing his fingers along Charlie’s cheekbone. “I think just the sight of you gets me incredibly hard and makes me want you desperately.”
Charlie blushed again and tried to look away, but Nick held him in place gently and went on, “I know that I’ve honestly never wanted more than what we already do together. We were both curious about this, sure, but what makes me feel connected to you, and wanted by you, and turned on by you… I don’t think it ever needs to involve that again. That was just–” he bit his lip and frowned. “There wasn’t any love in that.”
“You don’t ever worry,” Charlie said, wrinkling his nose, “that we’re like… bad gays?”
“Well I’m bisexual, so…”
“Oh come off it, you know what I mean.”
“I do know what you mean,” Nick said, "and I worry about that sometimes as well. But I also know that our sex life is… frankly pretty mind-blowing, wouldn’t you agree?”
Charlie nodded hesitantly.
“So then, yes, it's fucking. What we do is fucking. I mean, honestly, I’d be forced to conclude that based solely on some of the noises you make…” Nick teased.
Not missing a beat, Charlie teased right back, "I seem to recall you getting a housing complaint that time with the vibrator, so you’re one to talk," and Nick went beet red.
That seemed like a fine place to leave it for the night, so they settled on a shower together to wash away the discomfort of the experience, and let the subject drop.
The following Saturday morning, Charlie came home from doing the shopping to find a pretty blue envelope with his name on it waiting for him on the dining room table, and the smell of bacon wafting through the air.
"Two seconds!" Nick called out from the kitchen, "Just finishing the eggs!"
"Can I open this?" Charlie called back.
Nick rounded the corner with a smirk, holding a platter heaped with bacon, eggs, and toast. "You literally couldn't wait two seconds?" Charlie pouted at him, and he rolled his eyes. "Go on then."
Nick dished up breakfast while Charlie eagerly tore open the envelope to find two small enamel pins and a card. The card had a simple picture of daisies on the front, and where it would have been blank inside, Nick had written: “You’re the fucking love of my life. Get it? Okay, I love you.” The pins were identical: a gradient of blue, teal, and silver, with the term #sidepride etched in the middle. Charlie turned to Nick and cocked his head.
“So I’ve been doing some research.”
Charlie raised an eyebrow. Between them, 'research' was often code for, "Hey I saw this thing in porn, can we try it?”
“No, not like that. Well… also like that," Nick admitted, rubbing a hand along the back of his neck. "But seriously, I’ve been reading about us. We’re sides .”
“Sides?” Charlie asked cautiously, munching on a piece of bacon.
“Yeah, it’s a position. Just like top or bottom.”
“Wait, really? You’re not pulling my leg?”
“No, seriously. There are articles all over Queerty and Out Magazine about it. There’s even a Facebook group! I honestly feel a bit stupid that I never noticed before. It's not common, exactly, but there are plenty of couples just like us. They actually just added it as an option on Grindr!” Catching the look on Charlie’s face, he clarified, “Christ I’m not on Grindr, I just saw a piece someone wrote about it. Here, I’ll send it to you.”
Charlie’s phone pinged as Nick sent him five links in quick succession. Then, as he started to read, his eyes brimmed with happy tears. "Oh my god, it's actually a thing," he whispered.
"I know, that's exactly how I felt when I read them! But– sorry, could you have a bite of your eggs please, love? We both know you won't touch them once they've gone cold."
Still focused on his phone, Charlie absentmindedly lifted a forkful of scrambled eggs to his mouth, then spat them back onto the plate. They’d already gone cold.
Nick sighed and Charlie looked up defensively. “Sorry it’s just a-”
“Texture thing, I know. Obviously I know,” Nick said gently, taking his plate. “If I microwave them are you up to trying again?” he asked, already heading into the kitchen. When he didn’t get an answer he poked his head back around the corner. “Char, yes or no? I can make something else, but you should eat more than just bacon.”
“Right, sorry,” Charlie said, a giddy smile stretching across his face. He looked like the weight of the world had come off his shoulders. “The eggs will be fine if you warm them back up. Thank you for going to the trouble.”
Nick laughed and called from the other room, “It’s my fault, I should have known not to distract you if I wanted you to be able to eat. That one's on me.”
When he brought the plate back, Charlie tore into the food aggressively, so much so that Nick remarked, “Oi, I said eat them, not inhale them.”
“Mneed my sfrenght,” Charlie muttered, bits of egg flying from his lips.
“I’m sorry, you what?”
“I’m going to need my strength,” Charlie said again, washing the last of the eggs down with a swig of orange juice, “so that once I finish washing up, you can show me some of your ‘research.’”
“I’ve already sent you everything I read on Queerty,” Nick said, innocently.
Charlie stared straight through him, deadpan, with one eyebrow arched.
“Oh, you mean,” Nick blushed furiously. “Oh, um… then yes, eat up. And after that you can join me in the bedroom… and I can show you some of the um… I can, uh, recommend some excellent articles on… Ah, bugger it, I’m just going to fuck you senseless, yeah?”
“Righto," Charlie answered with a wicked grin.