How to Make the Right Move/How To Properly Read Her (Possible) Hinting
I have been at it with this girl for the past month, we aren't in a relationship but we act like we are, we kiss, we cuddle. Lately she's been joking around about her and I having sex(even what sounds like her challenging me to make more moves) and I'm trying to read into it whether she wants me to make a move and take that next step yet or not.
Examples may include the fact her and I have shared sex dreams about one another, written stories, and may(wink wink nudge nudge) have had a little thing over webcam together(we know one another in person we just Skype quite a lot). I've seen her shower, she's seen me shower. We've seen each other's private bits quite a lot already. She also likes how nervous I get when she does the things that she knows turns me on over Skype. Another example being how I said that if she ever does that in person she better be prepared for what comes after and she said "challenge accepted".
Main question is, next time her and I start getting intimate(kissing, making out) should I progress it and take it where it sounds she wants it to go? Or should I keep chickening out? I did something similar with kissing her before we finally kissed, where I'd chicken out a bit each time I knew she wanted me to do it.
I am actually surprised that you haven't made a move yet considering all the hints, which seem to be way more than enough. Are you too young or is there any other reason?
I believe timing is important and waiting for too long and being too passive is as bad as being too aggressive. Chickening out will make you come across as very unattractive, so you should try to take action sooner than later.