Riddle // Tell me How
Pairing: Riddle Rosehearts x Reader A/N: Brief break from requests for this self-indulgent Riddle piece. (I say as if everything I write isn’t already self-indulgent) More intimate than I was intending for my first Riddle piece but oh well Warnings: chest-touching 1.3k words
Riddle’s room was lovely to be in. If it wasn’t somewhat inappropriate you’d ask to stay all the time, just for the bed alone.
You considered the crowning achievement of your time at Nightraven College the fact that Riddle let you on it. He had made very sure to assure you of the importance of him doing so. And you, of course, felt appropriately honoured.
Honoured and self-indulgent enough (the sheets were so incredibly comfortable!) that it took a while for you to realise that Riddle was fretting.
Of course, the Heartslabyul housewarden carried an air of anxiety with him quite frequently. Especially you were no stranger to the shuffling of his feet or the nervous way he liked to brush hair behind his ears or adjust his clothes. Though it had lessened somewhat as Riddle had gotten used to the notion that his fond feelings for you were, in fact, reciprocated.
“Riddle” you interrupted the circles he’d been walking on the soft, checkered carpet. Riddle looked up, mid-biting his lip, and blushed as you took his hands in yours to rub your thumb on the back. “Is it something I can help with?”
“No- yes. Yes,” he said, squeezing your hands and taking a deep breath. “You- we said we’d both be okay with… exploring a bit if the mood arose, correct?”
“Mhm,” you confirmed, tilting your head fondly.
“So, what exactly qualifies as the mood?”
Ah, right, you probably should have specified. Riddle liked his frameworks clear, if they could be. And this was very, very new after all. It would be good to clarify.
“I suppose it’s when the atmosphere gets charged,” you tried to put it into words. “Like when we catch the other looking at our lips or staring into our eyes or we get… affected by each other.”
“Right, right,” he agreed with a quick nod before curling his fist into your sleeve, shifting his weight onto one foot so the other could rub against it. His cheeks were so red it reminded you of when he got angry. “And, say I was affected…how would I, uhm, have you reciprocate the feeling?”
You couldn’t help the bright smile that bloomed on your face as you nudged him to come sit on the bed with you. Riddle was so sweet and you’d gladly provide the steps he wanted even though he seemed to perform them intuitively.
“Being cute and squirmy will do the trick,” you said, leaning over him a little, Riddle instinctively leaning back, his head hitting the pillow, its white case contrasted by the red hair that fanned out as Riddle looked at you with his beautiful big eyes and a shy smile. “Telling me what got you affected might help along too.”
He’d been in the process of gently pulling you down by the front of your tanktop when his eyes widened further and he protested.
“No, that’s embarrassing.”
“I’m sure it’s not,” you said as you found a stable position over him. “Won’t you indulge me?”
Riddle chewed on his lip as he seemed to debate whether to stroke your ego or preserve his dignity before finally ruling in your favour.
“...your muscles. Your shoulders. They looked nice just now.”
You grinned, rubbing a thumb over his heated cheek.
“I’m flattered. Thank you for telling me.” You felt like adding on some praise but refrained, unsure how Riddle would feel about it in this context.
He visibly gulped and you watched his eyes shift in discomfort.
“Riddle, do you want to be on top?” you asked, leaning up a little to cage him in less, but he held onto you.
“What, no, why?”
You shrugged.
“To feel… safer, I guess?”
“I feel safe,” he assured you and you smiled in relief. “Just… a bit exposed.”
You lowered back down, trying to loom less. It would probably help if your line of sight was mostly restricted to his face.
“You wanted to explore, right?” you reminded. “Would you like to be touched or do the touching?”
His beautiful blush returned and he lowered his head, but answered firmly nonetheless.
“I would like to be touched, I think. If you’d like to.”
You really couldn’t overstate how much you would love to and how happily you’d indulge him, but decided to do instead of speaking.
You laid down next to him, nudging him to turn a little so you could settle in behind him, making sure to minimise the feeling of exposure he’d be experiencing. Resting your chin on his shoulder you wrapped your arms around him from behind.
“How does this feel?”
“It’s good. Thank you,” Riddle said, turning his head back a little to bless you with a small smile.
You placed a kiss on his nape and delighted in the little, pleased shiver you got in return.
“Anything specific you would like me to touch?” you asked, open to suggestions.
“My chest maybe?” Riddle offered. “I don’t think I’m ready for… more yet.”
“Sounds perfect,” you assured him.
Your hand wandered innocently over the button-up he was wearing at first but you quickly let it travel under it when you saw the pout forming on Riddle’s lips and preemptively saved him from having to specify his request.
He was warm and you could feel his smooth tummy flutter under your fingers, a hint of muscle poking through. Probably from the horse riding, your mind supplies.
You let your curiosity dictate your movements, fingertips dancing lower to feel for the differences in-
Riddle gasped, grabbing onto your wandering hand with both of his, his shoulders jumping.
“Sorry,” you said softly after giving him a moment to relax his posture again. “I wasn’t going to go any lower. I promise.”
“I know,” he assured you. “Sorry, I just got spooked.”
“Don’t apologise. I’ll stay right up here, yeah?” you said, moving your hand up to his ribs and he let go again.
“Mhm.” He nodded and gave you a grateful smile.
After a bit more exploring you reached his chest and enjoyed getting a feel for it before starting up a gentle massage, moving and pressing your fingers deliberately in ways you thought Riddle might enjoy.
“That feels nice,” he said with a blissful little sigh.
“I’m glad.”
You continued for a while, happy at the little contented noises you could draw out of Riddle, as well as the way his eyes fluttered closed and the heartbeat you could feel hammering against your hand before slowly calming.
“You can touch them too,” Riddle mumbled after a while. “M-my nipples, I mean.”
You gulped and gingerly (but very much eagerly) complied, beginning to explore the little nubs you’d carefully avoided so far. It was warm in the room so they were soft at first and you had the pleasure of feeling them stiffen under your touch. You were so absorbed in the experience of Riddle’s bodily reactions that it took you a bit to notice how silent he’d gotten.
“Riddle? Is it okay?” you asked.
“Hm?” he responded, sounding a little panicked at having gotten distracted. “Yeah! Sorry, I- it feels nice. I like it. I don’t think I’m very sensitive there but I like having you touch me there. It’s comforting but also a bit exciting.”
“That’s good,” you hummed and couldn’t help but adding: “They feel so nice. I bet they’re as beautiful as the rest of you.”
Riddle’s head snapped back and you adjusted a little so he didn’t have to strain his neck so much.
“Do you want to see them?” he asked and you blinked.
“I- yeah, of course. That is, if you’d show me.”
Riddle nodded quickly, clearing his throat to downplay the smile that was forming on his lips. But he turned back around, snuggling back in your arms.
“Not right now though,” he said. “I’m comfortable.”
“Me too,” you agreed, hugging him firmly.
