"I know it hurts. You have to relax or it'll hurt more, okay?" Simon asked, speaking more gently.

Hurt more? Trembling a bit he gulped. More than that? What Simon could feel it was that Naoki tensed up even more.

"Shhh...relax. Relax, Naoki." Simon whispered as he rubbed Naoki's stomach and whispered soothingly against his ear.

And the boy slowly relaxed. Being in those arms and hearing those whispers without any threat is was kind of... calming.
"It will hurt?", he asked, still a bit tensed.

"Not as much if you relax." Simon replied softly as he continued rubbing his stomach.

"B-but it will?", he aske nervously though he was slowly relaxing a bit more.

"For a little while, but I promise it'll feel good after awhile." Simon replied, trying to make Naoki relax enough to where he could move.

Young male nodded then and tried to relax some more. Though it was impossible to do that fully.. still it was enough for Simon to move.

Simon pulled the head of his cock out slowly, then pushed in again and this time went deeper and deeper until he was fully sheathed within Naoki's entrance. He let out a shuddering groan as he did so and kept his arms wrapped around Naoki.

Naoki cried out in pain as it happened. It almost felt for the poor boy that the thing going inside him didn't have end. The way it was spreading him was so.. overwhelming. He couldn't really think about anything else. Trembling a bit he let out a shaky breath, trying his best to relax a bit.