I nursed my DS1 all through my pregnancy with my DD and then tandem nursed them afterwards. I am currently 14 weeks pregnant and I'm still nursing my 15 month old DS2. I'm planning on tandem nursing this time as well. There are lots of mamas here with plenty of experience with nursing during pregnancy. I've also heard that "The Womanly Art of Breastfeeding" also had lots of info but I read it a long time ago so maybe someone else is better able to give advice on some reading material.
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In my experience...
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It is normal for your milk to dry up a bit at first. My supply always drops during the first trimester but usually starts to increase again during the second. My milk dried up a lot this time around, starting around 6 weeks pregnant, then started to increase around 12 weeks. It didn't deter DS much, though I know he felt a little frustrated at first. Make sure to drink extra water and get plenty of protein and calcium. Staying hydrated is key.
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If I remember correctly, it is also normal for your milk production to slow down again shortly before birth. I know my milk switched to colostrum at around 36 weeks or so. There was less of it but my DS still nursed without issue.
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DS1 nursed well through my entire pregnancy. The rise and fall in supply didn't upset him enough to make him wean, but I know that some babies are frustrated enough to stop nursing when there is a significant decline in supply. So far, DS2 hasn't been discouraged, either. I have never dry nursed as far as I know, there is usually something there, even if it isn't much. Sometimes he will comfort nurse for an extended period and I know my supply gets down to the bottom and he is probably getting nothing, but it isn't any more painful than productive nursing.
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As far as pain goes, most mamas find that it gets better as you get further along. This time around 7-11 weeks was the most painful time period. My nipples were so sensitive and painful. Now I don't find nursing to be any more uncomfortable that it normally is, which for me is pretty much not at all unless DS has been teething and has bitten me recently! LOL! The discomfort is usually the worst when he latches on and with let down but it was pretty painful the whole time for a few weeks.
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Congrats on hanging in there with it! Nursing through pregnancy and tandem nursing isn't for the faint of heart but it can have some pretty great benefits! :)