Tucker was 15 mos when I got pg w/ Griffin. He was nursing a TON at that time. It hurt like hell from the beginning, and, I hate to say it, but didn't go away until I had Griffin.

There were days I just sobbed because it was so uncomfortable. I tried to get him to cut back, but he never really did, and I just didn't have the heart to wean him, he seemed like such a baby to me.
My milk dried up around 4 months, but it didn't deter the little man at all. He acted like nothing had changed. Then when colostrum came in, he hated the taste --- would suck, smack his lips and go "Ick!" but then giggle and latch right back on

(I swear, vinegar could come out of my boobs, and he'd just swig it down)
So needless to say, on the third day after Griffin was born, my milk came in BIG TIME, and Tucker was overjoyed. Now I am officially tandem nursing, and it hasn't been easy, as Griffin is a nonstop nurser, but it's getting a little better day by day.....
Oh, btw, the pain was totally gone the minute I had Griffin. I mean, I nursed Tucker that morning and it was incredibly painful. That night, I nursed Griffin and there was noooo discomfort. So I thought maybe it was because G was a newborn and T nursed harder. He came to see me in the hospital the next morning, less than 12 hrs after I had G, and nursed, and it was fine....totally painless.
Didn't mean to write a novel!!
Oh, and CONGRATULATIONS again!!!