To make it a quick pain for Nao, as soon as the head entered her, I pushed the entirety of my cock in one swift thrust. Ignoring the resistance from her hymen. With how much virginity of a girl I've already stolen, I could say that it's better to rip it in one thrust than trying to do it gently by using five or more. It would hurt the girl more if it was done like that after all.
As tears started to form from her eyes, I wiped it away with my thumb and locked Nao's lips into a deep kiss while my cock was buried in its entirety inside her. Her lower body kept on squirming from the pain as it tried to pull away from me. The intense throbbing of the walls of her vagina was also trying to choke my cock as a defense mechanism to its invader.
However, even with all of that, I kept it inside her while I tried to take her mind away from the pain.
"I love you too. We did it, Nao."
I whispered as sweetly as I could to her.