splitmemory | late night study sessions

It's awkward, isn't it? Trey admittedly doesn't always get the chance to undress, to look at someone and be looked at in turn..... Anyone would be bashful, getting watched in a position like this--especially when they're as open about it as Riddle is. Trey knows better than to call attention to it, even without Riddle's warning--but isn't it asking a little much, telling him not to look too hard when Riddle is putting himself on display like this? Had he seen--no, is he trying to imitate the poses he'd seen in that beastmen porn? ~~No, wait. Shouldn't Riddle be on all fours to get..... well, mounted, in that case?~~

"Alright....." It doesn't matter. Don't think about it. Don't think about anything except..... except this. Them. Trey sets their pants aside, brushing past a dangling leg to open his bedside drawer. It neatly obscures what he's looking for, reaching in there blindly, but he emerges with a bottle of lube and condoms in hand. Better safe than sorry, right? Besides, better this kind of mess be contained than demand incriminating cleanup he might not have time for.

Edited 2025-04-12 10:03 (UTC)

He absolutely WAS NOT trying to copy the beastmen video he'd watched -- Riddle would be appalled to even have that suggestion made. Lucky for Trey that he wasn't foolish enough to say that out loud... but what he does next was enough to incriminate him for a lifetime.

Lube was... well, it's somewhat incriminating, but on its own Riddle could make excuses, could figure it was in Trey's drawer for much the same reason that HE kept a tiny bottle tucked away in his bedside table drawer. It's the condoms that do him in.

Riddle stares for a moment, his eyes wide, and--

"Trey Clover, what have you been getting up to?" Sorry, Trey, he might be desperate and horny but this won't slip THAT easily under the radar, unless he's distracted rather quickly. There's... also, a very small part of him that aches, that pputs, at the realization that this would only be his first, their first together, but....

With those supplies, it's obvious. Or, well. Sort of. He hasn't exactly caught Trey in the act.

The one silver lining? Riddle isn't exactly yelling at him, more in shock than angry. For now.

Erk! He can't exactly claim he was caught red-handed, when he's the one who pulled the things out himself, can he? Talk about awkward..... But he can't very well not do this properly, either. He doesn't want to hurt Riddle, and letting them get messy? They'd need to leave the room and use the communal showers in the dead of night. How much more incriminating could you possibly get? What if other students were awake to see and start asking questions?

Maybe he'd better focus on the questions Riddle is asking, first. Trey laughs, smile somewhere between sheepish and slyly knowing. "Hah, don't tell me..... You're not looking for tips, are you? I'm not really sure how good any advice I could give you would be, you know. Then again..... I guess anything would be better than what you've managed to find so far."

A successful diversion by Trey, putting him back in the lead! Riddle stammers, before biting down on the inside of his cheek, half glaring at him. He's caught, too, in a way. There would be more to say on this later. For now? He'll relax his body some, bring his hands up to rest them near his head against the bed, tilting his chin up and staring up at Trey through his own lashes.

"Tips? From you?" He scoffs, as if that's the most impossible thing in the world. "Hardly makes sense to ask for tips on how to get with someone from one I want to be with. Besides. I can handle flirting and courting someome just fine, thank you very much."

There's a hint of pink creeping back into Trey's ears, at that--what is he supposed to say, when Riddle claims that he's the one he wants to be with? That sounds almost as absurd as asking for tips from the same person you'd use the tips on, if he's honest. Even so, he looks back down at Riddle, fingers trailing up the younger boy's thigh in a slow caress.

"Really? You've flirted and courted before?" He may as well ask, if it means they'll steer further off-course, deeper into this new topic..... But honestly, who even uses the term 'courting' anymore? Has Riddle been watching fetish porn and reading etiquette guides from a century ago? What a wild combination.....

This was... essentially a confession at this point, wasn't it? More than literally being laid bare, Riddle was laying bare his emotions without even thinking about it, unable to think about it before he says the words that slip out from his lips. His heart is pounding in his chest, a small breath being taken in as those fingers trail up his thigh in a way that feels so intimate with how the topic is turning, how the topic has been steered by complete accident.

"Well, no..." Riddle shakes his head lightly, turning his gaze away from Trey. "... however, I am sure I could handle it." They're doing this a little backwards, aren't they? Riddle takes in a short breath, turning his head to look at Trey again. "Why do you ask? Shouldn't you be focused on getting me ready for you?"

Really, he's being a fool, thinking that Trey wouldn't accept his attempts to get in his bed with him.... Considering that's where they were, both undressed and preparing to do more than friends ever really do.

The conversation has kind of taken a turn for the weird, if he's honest. But isn't that just like him? If you put him on the spot when it really counts like this, of course he'll end up floundering. He's really just..... Isn't this too much for a guy like him? He can handle something low-stakes and casual, but..... this is important. Riddle is important. What if he seriously messes this--them--up? Riddle's not the sort of guy to just laugh off mistakes, right?

"Hah, you're probably right. I'm just..... curious, I guess? You saw me make a fool out of myself with that ghost, after all, but you never even got a chance to try." Any other flirting he's done is casual at best, accidental at worst..... everyone else tends to be the one carrying that sort of conversation. (And think his awkwardness is somehow endearing, thank Seven.) But Riddle is already getting impatient, isn't he? Trey takes a moment to slick his fingers, one pressing cautiously against Riddle's interest. He can't be too rough, if this is Riddle's first time.....

Or let Riddle be too rough with himself, just because he assumes he can handle it. It would be way too embarrassing to let either of them end up in the nurse's office.

Really, Riddle was questioning how they'd ended up here, too. This conversation was... not what he expected to have, during his first time. Actually, he hadn't expected to EVER have a conversation like this, talking about ... honestly, how does he even begin to summarize this conversation into the most basic of descriptions???? Riddle turns his head slightly to lean his cheek against his arm, keeping his gaze up on Trey.

In a way, even if this was awkward and strange, speaking so openly like this was somewhat... helpful? It helps Riddle focus, helps him understand where Trey's mind is at. "And that is precisely the other reason why I wouldn't ask you for tips." Riddle reiterates, though he's soon gasping slightly in shock as the cool, slick finger presses against his entrance, tentative and cautious. Suddenly, this is all the more embarrassing-- but he swallows that feeling down, shoves it deep away from himself.

"... If you're curious, maybe I'll just have to work on courting you and prove how simple of a task it would be for me." There, last comment on that, a light tease, before completely shifting the topic back in the other direction.

"I've-- done this part before. By myself. You don't need to worry. I can handle it." Riddle mentions, taking in another shaky little breath.

"Ouch..... I guess I deserved that." A brutal assessment, but not an inaccurate one, either. If Eliza hadn't driven every last nail into the coffin, then surely tonight had. It had just been a joke, a way to lightly and easily turn the topic away from any indiscretions Riddle might feel the need to punish him for, but that doesn't make it any less true. Still, he can take a wounded ego better than spending this encounter in a collar, right? It's an acceptable sacrifice.

"Th-that's really not necessary....." Read as: please do not. He doesn't know what he'd do if Riddle actually tried to court him. Sink straight through the floor, maybe? He's gotten used to the impatience, the rough edges, the way Riddle prickles over the past few years. How would he be supposed to handle Riddle acting like he used to, these days? He'd be completely unrecognizable, as much of a shock as reuniting with him had been originally.

No, no. Don't think about it. That's not important right now. What's important is making sure that this is gentle and comfortable, even if Riddle insists he can handle a little roughness. He wants to prove him wrong--prove that this doesn't have to be painful, whatever questionable videos he might have seen. Just focus on slowly, steadily stretching him open..... Too bad he hadn't had the time to let the lube warm enough to be comfortable. Then again, Riddle probably doesn't do that for himself either, does he?

It's Trey's own fault, the harsh words that left Riddle's mouth. Not that he was trying to be mean or insulting. More, they're honest statements, how Riddle was thinking in the moment.

Luckily for Trey? He seems to let go of his other thoughts and comments as he feels those fingers moving inside of him, slowly stretching and preparing him. He can't hold back the soft noises he makes, bringing one hand up to half cover his mouth, to quiet him and stifle any and all noises he might make. His body is more relaxed than might be expected, for someone who this was new to-- because he trusts Trey, really. Believes he would keep his word, prove to him that it doesn't need to be painful and harsh.

His hips shift, rolling slightly down against his fingers, to press them further inside. A movement fueled by need and desire, by nothing more than his desperation and lust. If Trey wants to control the pace, to keep it so gentle and caring, he might need to do something about that.

"It feels-- good. Mnn, better than when I do it." Riddle is gopd at giving feedback, that's for sure - and he doesn't tend to lie all that much, makibg it easier to trust his words.

This is suspiciously easy. Maybe even concerningly so. Riddle wasn't kidding that he could take it--what else has he been taking, if this is really his first time? Does he have some sort of crazy toy? Has he been that rough with himself, trying to get ready for what he thought the real thing would be like? Or is he really just that eager? The way Riddle is pushing down onto him--

"Th-that's good, but don't get too ahead of yourself. It's gonna hurt if you're not careful." Hadn't Riddle said earlier he wanted to be grabbed around the waist? Maybe he'll settle for a hand gripping his hip, holding him steady to keep his squirming from turning into harsher grinding. It's okay, just leave it to him; he may not be much good with romance or flirting, but he can at least protect Riddle from himself enough to make sure he enjoys this.

The hand against his hip elicits a tiny whine, as Riddle is held steady. Yes, it's working, keeping him from grinding harshly down onto him, protecting him in whole from his own eagerness, his own desires to push this further quicker. He takes in the words from Trey, nodding slightly to show he understands, to show he's processing that statement from him, not taking it as just a suggestion, but rather.. trusting him.

"Alright, alright..." Riddle murmurs, "You worry far too much, you know." His voice is quiet, soft, and he's moving one of his own hands down to rest it against the back of the one that Trey has against his hip, giving it a gentle squeeze, a small encouragement. "Take a deep breath and let's focus on enjoying this. Nothing else." Trey could still be gentle with him, still be careful and treat him how he deserves to be treated - but that doesn't mean he has to worry the whole time. Riddle wants to see him relax too, to lose himself a little, if he can.

They're both too uptight, aren't they?

"If all of you didn't give me so much to worry over, maybe I wouldn't." Even Trey's complaint is full of fond exasperation, shaking his head and sighing. This whole dorm is full of troublemakers, he knows that more keenly than anyone--Riddle included, as much as he would surely argue the point. All he's ever wanted is a normal, peaceful school life..... But that had slipped out of reach from the moment this year's orientation ceremony had erupted into such chaos, hadn't it? If anything, life has only gotten stranger and more stressful from there.

Still..... Riddle's not wrong, either. Trey's smile softens under that reassuring squeeze, taking a deep, steadying breath. It would be a struggle indeed to let go so far that he could truly lose himself--but he can try to enjoy this as best he can, and trust that Riddle will let him know if he's uncomfortable. A third finger presses into Riddle, gentle but insistent. Just a little further, and he'll be ready--once they're both properly wrapped, of course. But Riddle won't have to worry about that if he's too distracted with need, will he?

Really, it's a miracle he'd been able to speak up to this point, with those fingers inside of him. His body shudders under the feeling of both of Trey's fingers brushing against his insides, exploring him and spreading him with a purpose that only someone who knew what they were doing, at least a little, would have. His hand squeezes somewhat harder against Trey's as he feels that third finger press in, his body tightening and, well.

With the difference in size between the two of them, it's only a matter of time before Trey found the point where he wouldn't be as relaxed, where his body needed to actually adjust and accommodate him. Riddle moans, whimpers, bearing down on his fingers and squirming all over again, this time to adjust and from his need. Trey can probably see the way his dick rests against his stomach, a few drops of pre dribbling uselessly onto his skin.

"T-- Trey...!" He gasps out, squeezing his eyes shut, trying to hold himself together.

It's suddenly considerably harder to be gentle when Riddle is bearing down on him like this. His muscles don't stay obediently loose, his body rebels..... The difference is like night and day. What a turnaround! At least he can rest easy in the fact that Riddle's not in pain, if those sounds are any indication. Riddle's not going to get too loud, is he? Should he find something to help Riddle muffle himself with? Or is this in 'don't you dare stop' territory once more?

Then again..... he might not have much choice, the way Riddle is trembling so tight around him. He looks like he's only barely holding on; Trey hesitates in his work, uncertain, torn between what Riddle had declared he wanted versus what he probably wants right now. It's no big deal if he ends up blue balling himself, honestly; he'll be fine just waiting to calm down, if this turns out to be too much for Riddle. Riddle himself, on the other hand..... "Are you okay? Should I slow down.....?"

There's the fear that he MIGHT get too loud, yes, but Riddle knows well enough to bite his tongue if he needs to, to muffle his own noises with a hand or to pull a blanket over to cover his mouth with. For now, he's not too loud, keeping his noises quiet enough to be considered safe. He wants more, wants Trey to keep going, to not stop at all, even for a second.

So, when he hesitates, Riddle finds himself huffing slightly, fingers curling against the back of Trey's hand.

"I-- I'm fine," Riddle stammers out, peeking at Trey through half-lidded eyes. "Keep going. Even if-... even if it becomes too much, I still want you. All of you. Got it? I won't be content until I've had you." Don't let anyone say Riddle Rosehearts ISN'T stubborn as all hell.

"You still--Riddle, you're going to end up exhausted if you push that hard. You know that, right? It might not even feel good, at that point." Trey stares down at him, incredulous. He knows Riddle is stubborn to a fault, but isn't this a little ridiculous? It isn't as though this is their only opportunity to touch each other..... They can afford to take things slow, to take care of Riddle the way he deserves to be. He just.....

He just feels like he owes Riddle at least this much. Especially after he's already stolen so much from Riddle, the thought of completely ruining something that's meant to be so romantic and special like this..... it hurts his heart in ways he doesn't have words for. They say you never forget your first, right? But he's not--this situation isn't exactly ideal. Seven, what a mess. None of his other encounters have ever felt this complicated or fraught, knowing that they were just..... just because.

Trey's fingers obediently start moving inside him again even so, if more slowly and carefully than before; the hand on Riddle's hip pulls away, instead reaching for the condoms still laying beside them to get them both ready. If Riddle is already struggling, then he'd probably better be quick about this, huh? Maybe he can keep him from feeling like he needs to push past the limits of his endurance to begin with.

"I understand that it may exhaust me. That's hardly an issue." See, there it was: the stubborn attitude. Riddle knew it was crazy, unreasonable, but he's already tired, sleep deprived. His mind was running with thoughts, suggestions, wild ideas of how far they should take this. How many times they should go, how much he wants from Trey. Their hands part, and it's the encouragement that Riddle needs to shift his positioning, to reach both of his own hands up.

Trey might be wanting to focus on the condoms, but Riddle has other plans. This is his first, what he would remember always. He isn't going to say it was the ideal, that it was just as perfect and sweet as he had expected... they can still make it sweet, still add to it and make it a memory worth remembering. Both of his hands grab at Trey's face, cupping his cheeks as the older boy's fingers start moving again inside of him.

"Come here." The demand is made, with the added pressure of Riddle tugging and pulling to lead him to lean down. If he DOES follow his order, Riddle's goig to press their lips together again. This time, softer. Gentler, intimate. Romantic, even, as if he was the one getting TREY ready to take HIM. Both of his hands cup his face, warm and needy but also... nothing else but warm and sweet, to reassure him of several things: this was okay, they are okay, and there's nothing that he'd want to change about this.

"You're impossible." It's surprisingly tough, trying to figure out what he should do when there are no rules that apply. (And isn't that strange, when the Queen of Hearts sometimes seems like she made a rule for everything?) The scripts don't line up the way they're meant to, like trying to watch a TV show when a different episode's audio is edited in by mistake. He may be better at thinking on his feet than Riddle, but who can plan for something they had dismissed as a possibility at all?

This isn't just some casual encounter they can easily fold into their existing relationship--and it's not the sort of mundanely charming meet cute he's always assumed he'd have at the patisserie, either. How they'd met and reunited isn't exactly the kind of story you'd be eager to recount over dinner. Neither is whatever this is, for that matter. Especially if he actually allows Riddle to push past his own physical limits, just because he got a taste of freedom and immediately ran wild.

Even with all his misgivings, though? Trey is obliging to a fault. In spite of his warnings and protests, he still finds himself obediently sinking down to kiss Riddle, hesitation giving way to something sweet and soft. Riddle always does manage to get what he wants in the end, doesn't he? Hopefully they don't end up regretting it enough to tarnish the memory, if nothing else.

It's easier, to handle, once their lips are pressed together again. He can focus on their kiss, on the feelings running through him, on the emotions he feels. His eyes close, allowing him to relax more in full, his hands slowly traveling to allow him to wrap his arms around Trey's neck, to pull him further down, to let one of his hands press against his back, between his shoulders. Eager, yes, but also...

He's trying to help Trey relax. To help him get back into the moment, instead of arguing and trying to bring logic into this. Later, Riddle would have the time to be embarrassed about how rash he was, about the ways he justified this to Trey, about... pretty much all of how this went down, but right now?

He wants to focus on them.

Really, despite being so logic-centric? He's always been a little impulsive, once he's got what he wants in his sights. His lips part carefully against Trey's again, tip of his tongue this time moving to drag across Trey's bottom lip, to ask for entrance sooner rather than later. It'd be him exploring, him taking over Trey's mouth to wholly and distract him away from his thoughts, his logic, his reasoning. Isn't this better, after all? To go with their gut, to proceed with what they're feeling, what they want.

Hopefully Trey doesn't mind when his fingers curl against his bare back, when his nails dig in, and he makes a quiet noise into his mouth. He's dangerously close, but fuck if he's going to let himself reach that peak before Trey's inside him - with Trey's protests from before.

Riddle's stubborn - and would get what he wants, in the end, as always.

When push comes to shove, he's the one with the temperament to thrive on routine by choice rather than necessity--the one whose expectations had come so wholly from within. Is it really any surprise that he's quicker to get lost in anxiety than passion, that this first taste of relative independence has tasted more of uncertainty than freedom?

Still, he wants to do his best. He wants to make this a cherished memory for both of them, if he can. Trey slowly relaxes under Riddle's touch, lips parting to tangle their tongues together as the kiss deepens. If anything, nails in his back are more normal than this hesitant tenderness; Trey shifts atop him to pull his fingers out entirely, replacing them with a cock pressing slowly but steadily into him. He'd say something reassuring, maybe, (as if Riddle was the one who actually needed it) or ask if he was ready.....

How is he meant to do that though, when Riddle is so busy exploring his mouth? Better to just listen to the younger man's body, instead of asking outright.

Just as Trey tends to lean into anxiety, into order and routine by choice, Riddle is a fire unlike any other. Burning as bright as the fire magic he commands so easily, impulsive and rash to a fault even when trying to impose order. Had he been raised with a kinder hand, maybe he'd even have ended up acting more like Che'nya, more free and passionate, following his heart instead of the rules set out for him.

Oh, but he's following his heart now. His body tenses slightly as those fingers leave him, the smallest of gasps breathed against Trey's lips, before his tongue is right back to tangling with his. It's not a completely new feeling, though he does find his body tensing and his back arching in a way he didn't think possible. The feeling, being stretched by Trey like this - it's ten times better and more overwhelming than his own fingers ever could be.

It's then that he needs to break the kiss, another gasp breaking their silence. He's clinging to Trey, breathing unsteady with need. He knows it's probably going to be a tight fit, especially with his body baring down on Trey as if to help bring him in.

"I... this position is embarrassing..." Now that he's so hyper focused on it, that is. "Can you feel everything? See everything...?"

Ah, this is tight. It's slower going than it should be, with Riddle so worked up; his body wants so badly to accept him that it almost locks him in place instead. Trey lets out a soft, shaky sigh, focusing on easing in as gently as he can manage. As much of an effort as it is though, Trey can't help a breathless laugh at Riddle's questions. "Can you?"

Trey can at least shift his weight enough to free one hand, stroking Riddle's cheek encouragingly; looks like it's his turn to be reassuring this time, hmmm? "Pressed together like this, I can see and feel about as much as you can. Would you prefer some other position, next time?"

That is..... assuming there is a next time, of course. He shouldn't take this--take Riddle for granted.

The hand stroking his cheek does help somewhat, his head tilting enough to let him lean into the touch, his eyes partially closing as he looks up at Trey through his lashes. Under normal circumstances, he might stammer or stutter, shove at Trey to get him to apologize for teasing him. Now? Now, he's focused on nothing more than every physical feeling he had.

"I want to try more, but... there's nothing I'd say I'd prefer, necessarily." As much as he complains and huffs and puffs, or makes little comments here or there, his body tells the story loud and clear, more honest than his words could ever. He's enjoying this, even with the slight ache that pressing in causes.

Here, Riddle will try to help. He shifts his hips lightly, moving his leg to hook it around Trey, pressing his heel in against his lower back, hoping that this position would help open him up just a little more.

Is it really teasing, if he's just pointing out the obvious? Maybe a little, when Riddle is already so embarrassed. Even so, if Riddle's already looking forward to experimenting..... That's a good sign, right? He's enjoying this enough to, well..... to tolerate the awkwardness, and embarrassment, and discomfort. To put up with him, even if this encounter has been strange and stilted.

He might bruise in the morning, having a heel dig into his back like this--but Trey is easily strong enough to support both their weight for them, to finally fully seat himself inside Riddle as the younger boy shifts their angle. They're going to need a minute to adjust before he can start moving again either way, so he might as well ask, right? "What else did you have in mind, then?"

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crimsontyrant - 2025-05-28 04:53 (UTC) - Expand

late night study sessions

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