Now that I think of it. This does not need to be limited to student and student. Your character could even be one of the school faculty like the librarian, vice principal, teacher, school secretary or nurse. Going outside of school, a nerdy and lonely housewife. She could even be a famous youtuber and cosplayer, if you wanted to really reinforce the 'lucky chance of being in the same area' thing. Personally, I would like to do a school thing, but I am open and have other suggestions. Hell, it could even be his own twin or older sister even and they could have even RPed sex online with each other for years too. The other would be incest as well, but the woman being his stepmother.
Also, I really do want to do an interracial with this and darker the skin and thick girls are were I would like to go. Probably one of the few things I'll budge on. =/ However, I do have other images and I will be willing to still look at others.