splitmemory | late night study sessions

Oh, poor Riddle. he's not used to getting caught doing something wrong, is he? Only a few times, only for significant things, with even more significant punishments. Trey can't help but feel bad for flustering him so badly, but even so..... He can't help but think, deep in his heart, it's probably a good thing.

Maybe Riddle needs an opportunity to realize it's okay to screw up, to get caught out in something embarrassing but mercifully small, and realize that it's okay to not be perfect. It's okay if his research is a little skewed, strange though the direction is. It's okay if he admits to having needs and desires--even if that's admittedly something Trey himself struggles with. Nothing terrible is going to happen to him, save for this moment of being flustered, before he hopefully forgets all about it in the excitement of finally getting touched.

"Okay, okay..... My lips are sealed. Just leave it to me." Should he try to help Riddle find somewhere better to look later? Maybe, if they don't expire from sheer embarrassment over the attempt. Trey smiles sheepishly to see just how alarmed Riddle looks, but he pulls away from the hand holding his face now, head dipping to oblige him. Soft lips press against his skin, obediently kissing his way down Riddle's neck. He'd asked for him to explore, hadn't he? Might as well be a little methodical about it.

Riddle does need an opportunity to mess up, in small ways. Ways that won't end up hitting him in a negative way, in a way that won't force him to take two steps back at each turn. He's already coming up on so many of those roadblocks with the changes he's making. The steps he's taking, the things he's learning, will always have some very small things he can mess up on. Social situations, especially.

Intimacy, too, was something he was so new to. Admitting his own needs, desires, wants; all of that was so strange, so foreign to him, when previously he'd always been focused on what he needed to do, what he needed to focus on, without any added factor of what he wanted, what he needed.

His flustered state regarding that little embarrassment does quickly fade away, with the press of those soft lips against him. Riddle lets out a shuddering breath at the feeling, his head tilting ever so slightly in the other direction to give Trey more room, to allow him more space to kiss, to adore. His face stays flushed such a deep red, as his hand moves to now rest against the back of Trey's head again, to encourage him to continue, free hand again moving to his waist, to press in against his skin and cling to him there.

"... Trey..." He just about whines, sensitive with his own need, squirming under him and, despite his own wishes to keep his arousal a secret for now (which he absolutely failed at), his hips are moving on their own. Slight movements, but movements nonetheless, allowing him to grind ever so slightly up against the other boy.

It may all be new territory, but the unknown doesn't have to be dangerous or frightening. It can be something exciting to explore together, right? Even Trey has to admit, this isn't exactly something he's done before; they're both figuring out what they need to do, how they want to feel. This kind of hesitant tenderness..... Even Rook's habit of romanticizing everything doesn't hit quite the same way. They just don't have the same kind of history together, after all.

"Hmmm?" Does he want something more? Something different? Surely Riddle doesn't want him to stop, the way he can feel Riddle's arousal sliding against his thigh. Either way, he'll have to speak up; Trey's head stays obediently bowed beneath the hand in his hair, lips trailing down over Riddle's chest. A moment's thought, and he tilts his head to wrap them around a nipple, sucking soft and experimental. Had he meant teasing them like this? Harder, maybe? Should he be using his teeth or tongue instead?

In a way, this was more intimate than anything Riddle could have imagined. Almost like they were meant to reach this most basic of stages, to enjoy each other wholly and completely. As much as he wants to think, to continue to make demands, the tenderness sending little shivers throughout his body. How is he supposed to focus when-?

His fingers curl, grasping onto his hair as those lips wrap around that sensitive nub, a quiet whimper pressing past his lips.

"Keep- Keep going." He murmurs, "Just like that." A continued encouragement, as he arches his back and tries to press his own knee further between Trey's legs, slowly but surely trailing his free hand down the other boy's back, fingertips light and careful, yet filled with a purpose.

"It feels-- hot, under your touch, your kisses. I like it. Don't you dare stop." What a silly demand...

Amazing how Riddle manages to get a grip on such short hair, when even this much is making him tremble already. Even Trey can't stay unmoved, when Riddle is touching him so deliberately; slowly but surely, his own arousal grows against Riddle's thigh, breath coming hot and shaky against the younger boy's skin. "I-it's supposed to."

Because of course he would grasp onto the cerebral, scientific side of this, in some effort to ground himself and soothe his nerves. Riddle gets his wish, either way; Trey's tongue toys with Riddle's nipple as he sucks, free hand squeezing the thigh that isn't trapped between his own. Pulling it tighter against him, helping raise Riddle's hips to encourage him to grind against him more firmly..... Now isn't the time to hide behind propriety. Riddle needs--no, Riddle deserves to pursue what he wants with everything he has. Just because he feels the need to be gentle doesn't mean Riddle has to be, if he doesn't want to.

Trey is so damn lucky that Riddle doesn't scold him for his words, for the logic he points out to him. Instead, Riddle breathes out a little huff, his own nerves completely soothed in favor of focusing on the moment. On the physical sensations he was experiencing, on what he wanted, what he needed to demand from Trey.

Maybe not so much in words, either. With his hips guided, it does encourage him to be more firm with what he wants, to press himself against Trey in full. His body, small as it may be, has some strength, enough that he can roll his hips harder, his arousal pressed up against Trey's thigh desperately, while his knee shoves hard against Trey's own.

His pants, while thin and loose, felt uncomfortable now.

"Be a good boy and finish helping me get undressed already." He murmurs the demand, as his hand loosens it's grip on Trey's hair, to instead smooth it down. Seven, it's hard to focus when he's like this -- if he's not careful, he's going to have a damp spot in his own pants, from pre alone. "You know I'm not one to be patient. I want you." Petulant and bratty, as per damn usual.

Anyone who judged Riddle only by his appearance would be caught off-guard by just how powerful his legs are, wouldn't they? An equestrian like him might well be better-suited to be on top than Trey himself is, straddling Trey to grind on him with enough strength to completely control the pace of their encounter. Even in this position, Riddle is quick to take control once it's offered; Trey sucks in a shaky, conflicted breath, borderline overwhelmed with the force of Riddle pressing into him. Even for someone who likes some roughness, that's a little much.....

"R-right, right. Let me just....." Don't dare stop, but also get him undressed..... Which one is it, then? The most recent order probably takes precedence, right? At least Riddle only sounds impatient, not genuinely annoyed. Trey shifts back enough to put a bit of space between them, squeezing his hands between their hips to unfasten both sets of pants. Better get them both off at once, while he has the time and room to; Riddle certainly won't want to untangle himself a second time. If he's honest, he doesn't really want to, either--both because he's starting to feel a little impatient himself, and he just..... doesn't want to let himself think too long and hard about this.

The more he ~~over~~thinks about it, the more he's going to dwell on it, the more reasons he'll find to question the wisdom of this decision. Someone has to be the voice of reason around here--but for once, he desperately wants it to be someone else, anyone else.

It's a process, one that Riddle wishes would go quicker. Needing to untangle at all was frustrating, annoying, but he understands the necessity. The smaller pulls back enough to assist, letting his knee fall back from Trey's arousal, legs shifting enough to assist with the process of getting the two of them fully undressed.

All at once, the embarrassment floods back into his form, his face burning such a bright red that he matches the color of his hair. Now laid bare for Trey to see. In the same vein... Trey was, too, or would be shortly. Riddle shifts slightly, to prop himself up on one elbow. To watch him get his own pants off, too, and to see what he's be working with.

Is he staring? Maybe a little.

"..." Swallowing, he lets himself lie back again fully, bringing a hand up to partially hide behind. It helps, then, when he brings his legs up slightly, spreading them to give Trey room to settle between them again, this time in a different position. One that, while Riddle wouldn't be able to shove his knee back into place, he would surely still have plenty of control, by virtue of who he is. One of his hands presses to the back of his own thigh, allowing him to partially spread himself open to make it more clear.

A sight that, probably, isn't at all expected of Riddle of all people, showing himself off whether on purpose or not.

"Don't look too hard or stare, alright...?" He says, despite his own staring and the position he's got himself in.

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.

late night study sessions

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