I leaked until...ummmm...a couple months into this pregnancy actually, so that's what? A year and a half!
No leaking and no colostrum stains before the birth, then my milk came in a few days later and Oh My Gods! For the first month or two I needed to press a cloth dipe over my "open" nipple while nursing. And it would be soaked by the time DD was ready to switch from one breast to the other. If I didn't cover the nipple I would literally SHOOT milk across the room during letdown! It was crazy.
After the first month or so I leaked a lot less, but for the first 8-9 months I had to wear nursing pads (the super absorbant disposable kind and even then they were doubled up and changed every couple hours) 24/7. Then my period came back and I only leaked during letdown or if I missed a regular nursing or pumping session. I was thrilled. Honestly despite all the pain and problems nursing dd during this pregnancy the fact that I'm not leaking makes it all worthwhile!
My personal tricks...cloth diaper or "urp cloth" held tight over my breast while nursing to catch leaks. Always covering the mattress with a waterproof pad or absorbant pad to catch nighttime leaks. Gerber brand nursing pads (the super thin ones) are good for not leaving a huge "line"...the Lansinoh brand is actually more absorbant but the "perky nipple" design is horrid through clothes and I'm forgetting the name but there's another brand that seriously looks like a starfish crawled into your bra.
For me nursing tops were never worth it. I wore my maternity tank tops with the built in shelf bra (the spaghetti strap style from Target) and just pulled the side down when I wanted to nurse. I just don't like the look/feel or those "bullseye" breast cut-outs found in many nursing bras and tanks. I also seemed to settle into an odd size...tops that fit well around my breasts were too large over my shoulders. Or the breasts would be fine but the tummy area really baggy. So the maternity top + a cardigan or other shell worked well for coverage and a work appropriate look that was easy to nurse in. I also slept in those tops since the shelf bra could be easily stuffed with prefolds!
Oh, and I was one of those lucky mamas who had the postpartum sweats/chills...for the first week or so I wake up to nurse but also because I was drenched in sweat and either too hot or waaaaay too cold. It's apparently not that uncommon. So I had a bunch of old/oversized flannel button down shirts that I'd keep next to the bed. I'd wake up, nurse dd, pull on a new (dry!) flannel shirt and tank top, stuff a dry dipe into the shelf bra, and roll over again. It sounds complicated, but it wasn't that bad. And I wish someone had been a little more up front about the night sweats/chills. The books mentioned it, but they didn't really talk about just how wet you can get during one of these mama moments!
DD and I are still nursing and I'm looking forward to tandem nursing when Roro arrives, but...well...maybe this time I wont leak like niagra falls?