[Encouraging. Those strong fingers of his play up and down his shaft, teasing the underside and rubbing the smooth tip. The size didn't bother him, either. If anything, he just found it cute, to go with the rest of his cuteness.]

Well, if you're still a virgin, it just means I have to be extra careful with you. I don't want to hurt this tight little ass, now, do I?

[After saying so he lifts his hand, sucking over his thumb to get it nice and slick with saliva, then starts to smear it over that hole. It's not as good as proper lube would be, he knows, but it's at least a step in the right direction. Who knows, if he does his job right, he actually might get the brat to loosen up.]