Simon pulled his tongue out slowly after a few moments and undid his pants slowly to free his erected cock and sighed softly in relief. "C-Can I put it in, now?" Simon asked.

"W-what... no... It will hurt", protested Naoki, a bit scared.

"I'll be gentle so it doesn't hurt so bad." Simon said softly, then made a face realizing he needed lotion to ensure it didn't hurt as much as before. "There's lotion in the nightstand."

"Huh?", asked only Naoki, not knwoing at all how it could be done without girls wettness.

Simon used his levitation ability to get the lotion from the nightstand and he took it in his hand to coat his member, hissing a little from the cold feeling of the lotion on his cock and he then pulled Naoki's waist to the head of his cock where he rubbed it against the neko's entrance and he slowly and gently pushed inside with a deep groan.

When he was pulled to the man he parted his legs and due to that his hole was placed perfectly on the right place. When the hard cock started to part his walls he whimpered, not really used to the feeling. Digging his nails into Simon's shoulders he didn't even notice when they became claws.

Simon groaned softly as he felt claws dig into his shoulders through his leather top and he pulled Naoki against him, having turned the neko to face him before pushing inside. He kissed the side of his neck once he was all the way inside, waiting until Naoki was ready for him to move. "Easy...is it worse than last time?" he softly panted.

Naoki cried out as the hard thing was pushed inside his ass so deeply. Digging his claws a bit deeper he closed his eyes, a bit startled.
"....don't know... I'm scared", gasped Naoki, hiding his face in Simon's arm.

Simon rubbed Naoki's back slowly and played with his tail to keep him relaxed. "Shhh...remember, if you don't relax, it'll hurt more."

"Stop making it even more scary..", gasped Naoki and then tried to take some deep breaths in and out, hoping it would help him a bit.