Questions: Flirting

Anyway in class today i was talking to this girl about cuddling
we were in the back of the classroom and i was pulling/playing with her hair, we had nothing else to talk about..

And i was looking down at her breast.. her breast are abnormally large.. and she's not even big.. i was asking if she's ever cuddled with someone, she said with her friends but that was all.. i wanted to ask.. isn't it weird cuddling like that with breast that big? but i avoided asking it probably would have gotten weird so...

Guys have you ever cuddled with a girl who had large breast and was it weird?
Girls if you've ever cuddled with one of your friends or girlfriends and either of you had large breast was it weird?

Itd be more than weird if you both had them...
if you've been in that situation tell me what it was like lol

I've been texting this girl for almost a week and she always replies but i'm wondering if she finds it annoying or not. Should i take a break from texting her?

I am quite shy and likely socially awkward (or something akin to that) and I can't really imagine making a first move. The closest I got was asking a mutual friend to mention my name and 'test the waters' and she like told the girl that I liked her and she told me that the girl was interested in someone else who she later ended up dating.
Anyway, will I really have to put myself out there more to start a relationship? I know that it's only rejection but I really hate putting myself out there and I think that girls should make the first move if they're interested and are more confident than the guy but I don't usually see that happen (with people I know, people I don't know who talk about their stories, in movies and such).
So I wanted to know what most people think about initiation and showing that you're romantically interested.