Simon started to stroke Naoki's member slowly as he remained still, trying his best to have the neko relax while he struggled to keep himself calm. "Shh...relax, kitty, relax." he said in a soft, soothing whisper. He was tempted to ignore Naoki's pain, if it were anyone else he would've, but he couldn't do that to such a frail youth. Not when he was acting so damn helpless.

When his member was touched, being still half hard, he gasped a bit startled but then those whisperes made him relax slowly. Simon wasn't moving so the stress and fear disappeared and were replaced with pleasure. Naoki moaned as his cock was stroked, making it become fully hard once again. What Simon could feel was that the boys body stopped trembling and his hole slowly adjusted to his cock.

Simon smiled feeling Naoki relax around him and slowly began moving in and out of him gently, panting softly into his ear. "See? This isn't so bad." he teased.

Naoki moaned softly as Simon started to move. It was somehow.. not so bad. It still hurt but not as badly as before. And after some time it even started to feel good, making Naoki let out a sweet, small moan while his claws digged into sheets of Simon's bed.

Simon purred hearing those sweet moans and ran a hand into Naoki's hair to lightly pull on it while he started thrusting faster and harder, thrusting even deeper into the neko. "That's a good boy...make more of those sweet sounds for me." he softly panted.

Naoki shivered when he felt mage's hand pulling on his hair and then moaned louder when the thrusts became rougher and deeper. Good boy.. Was he a good boy? He asked that himself but soon that thought was wiped out from his mind when something inside him was hit, making him meowl and then cry out in pleasure while clawing on the sheets beneath him.

Simon grinned hearing that mewl. "Right there? You want me to fuck you right there?" he asked roughly as he assaulted that same spot over and over again as hard and fast as he could. He panted much quicker and was lost in a white haze, not really paying attention to what he was saying anymore. He was strongly turned on by the sounds that Naoki was making and the way his hole shook around him with every thrust to his prostate.

Naoki was only to nod as an answer and then cried out in bliss. There was some pain as Simon started to pound into his hole but it was distant because of waves of pleasure coming every time the hard rod inside him pushed forward. With his tail rised high he let out moan after moan being in heaven right now. His cock started to let out drop of pre cum, wetting the sheets more and more while his claws teared them deeper. Naoki was too much into the pleasure to realise what he was doing.

Simon felt Naoki's cock leak precum in his hand and he felt himself leaking precum into Naoki's hole, getting close to cum. He pulled Naoki's hair harder so he could roughly kiss the neko's lips, shoving his tongue into the boy's mouth and dominating his tongue as he did so.

He gasped when he was brought to the kiss by pull given to his hair. It felt so good to be kissed like that. Simon dominated him in every way possible and he didn't mind. More.. he loved it. Naoki moaned lustfully into the kiss, his holtightening a bit as his cock become bigger, showing it was ready to cum again.