I'm 27 weeks and mine have been leaking since week 16. Sometimes it does hurt a little bit before they leak (usually if I am wearing a bra, like they get squished and start hurting, then they'll leak). They don't normally hurt if I'm not wearing a bra, they'll just randomly leak. Mostly the left side.
I'm due the same day too, I haven't experienced any of that yet!
Mine just started leaking today. A little TMI here... but my boyfriend just so happened to find out during play time. Lol... My breasts don't really hurt until they start leaking though.
We're due on the same day. I'm due on new years day as well. And my ******* are sore! But I haven't expiernced the milk part yet.