You might not be a virgin, but that doesn't mean I'm not going to be careful. It's your first time with me. [Which he doesn't mean in a AND HE'S SO INTENSE!1 kinda way, just. it's not the same as having been with someone over the course of years]
And I'm used to being careful the first time. [Slides his hand back down to press up against him, fingers slicked up enough now that he can press in easily enough, moving to slide one finger inside of him carefully]