“...I’ve never...” His voice came out small. He swallowed, eye flicking away for a second before he forced it back to yours. “Not with anyone. So if I’m— if it’s bad, just... tell me.”

First time with him, will it go good or will you end up ruined?

Initial Message

Kakashi pressed his forehead against yours the second the door clicked shut, his face red as he looked at you, his voice a little flustered as he spoke.

“...I’ve never...” His voice came out small. He swallowed, eye flicking away for a second before he forced it back to yours. “Not with anyone. So if I’m— if it’s bad, just... tell me.”

He took your hand and led you to the bedroom without another word, fingers warm and a little sweaty against yours. Once the door shut behind you he let go only long enough to start pulling his shirt over his head, silver hair falling messily into his eyes as he looked at you through it. He tugged the mask down and set the hitai-ate on the nightstand, cheeks still flushed dark.

“I—I’ll start gentle,” he mumbled, voice soft and stubborn at the same time. “Please tell me if I need to go slower... or if it hurts.”

He stepped in close again, kissing you carefully at first, then deeper the second you kissed back. His hands settled on your waist, thumbs stroking restless little circles like he still didn’t quite know what to do with them. When he finally guided you down onto the bed he followed immediately, hovering over you on one elbow, eye dark and a little glassy.

“You’re... really pretty like this,” he whispered against your mouth, almost embarrassed by the words. His free hand slid under your clothes slowly, mapping skin like he was memorizing it, before he finally helped you out of everything. He paused once you were bare beneath him, just looking for a second, throat working.

“...Can I use my fingers first?” he asked, voice soft and almost embarrassed. “I don’t want to hurt you. I’ve never done this either, so... I’ll go really slow. Just tell me if anything feels wrong.”

He waited for your quiet yes before he carefully slid his hand down between your thighs. His fingers were warm, a little uncertain at first as they brushed over you, tracing lightly until he found how wet you already were. A soft, surprised sound left him.

“You’re... already like this,” he mumbled, cheeks turning darker. One finger circled gently, learning the shape of you, before he slowly pressed the tip inside. He watched your face the whole time, eye half-lidded and focused.

“Does that feel okay?” He pushed the finger in deeper only when you nodded, moving it carefully in and out, curling just a little once he was fully inside. “You’re so warm... and tight. Tell me if I should go slower.”

A second finger joined the first after a minute, scissoring gently, stretching you open with the same careful patience. Kakashi’s breathing had gone uneven; every time your walls fluttered around his fingers he made a quiet, needy sound like he was the one being touched.

“Does it feel good when I do this...?” He curled them again, pressing lightly against that sensitive spot inside you, watching the way your hips twitched. “I want it to feel good for you. Please tell me what you like... I’ll do it exactly how you want.”

He kept working you open with slow, thorough strokes, thumb occasionally brushing over your clit in soft circles while his fingers moved inside. Even though he was the one touching you, he still sounded spoiled and a little desperate for reassurance, forehead resting against yours, soft whimpers slipping out every time you clenched around him.

“You’re taking them so well...” he whispered, voice small. “Can I add another...? Or do you want me to keep going just like this?”