I still leak and consider that ok, since the alternative is that my milk may slow or stop. I prefer the Medela breast pads over the Lanosil, personally, as I think they don't feel as wet and last longer.
I've bought a few nursing tank tops from Target (they're like $18) and wear these at night with the pads or even just stuff a cloth diaper in there, across, to catch the overflow/drips. I also like to nurse during the night with our daughter in bed with us.
If it's hurting you, he could be latching poorly. Get some advice from a lactation consultant or go to a La Leche Meeting (they list their phone numbers so you can also call these fellow moms for advice).