I nursed dd until just about a month ago, right before her 2nd birthday. That probably disqualifies me for this thread, but I needed to chime in to commiserate with the ladies who are nursing through the pain! I am still in awe of how much it HURT once my supply dried up. I compared it to getting my nipple pierced, and the pain was constant - it didn't stop until she unlatched. Oy!
When I first found out I was pregnant, I decided to just go with the flow and see how things went. Then when it started hurting, I decided we needed to figure out a way to stop...THEN once it looked like dd might actually wean, I totally regretted it! She was soooo sweet those last few months and I miss it a lot. I started talking to her about how much it hurt mommy to nurse (of course telling her that it wasn't her fault) and that she would need to nurse less soon. It totally didn't work to get her to nurse less, but every time she asked to nurse, she would say, "it's okay mama, it won't hurt, it's not my fault, and she push her hand against my cheek until I relaxed after she latched on. SOOOO SWEET!!!
She was down to about 3 sessions a day, and dropping the one when I got home from work was the hardest. After that though, she just started to forget occasionally, and when I told her once when we were getting ready for bed that we weren't going to nurse that night, she said "okay." And that was it. I was sad for a while, but I don't miss the pain!