I am 4 months in and my DS is a bit of a tricky customer - he shouts between suckles, people probably think I am nipping him or something. However, they are usually way more embarrassed than you, haha, seriously - if your nipple is on view, most people Avoid Any Position Which Could Suggest They Are Looking. Apart from very young children, who mortify their parents by staring.
My preferred method of dressing is a nursing bra plus a bando or bump band with a normal top (so long as it is liftable). Didn't like any of the nursing tops in Jojo etc.
I did find it painful at first, but the pain does go really soon. The first few sucks were sore but it would ease to bearable if the latch was correct. This lasted no more than 3 weeks and got better all the time (kicked in when the milk came in). Now it feels nice, the letdown reflex is a very satisfying feeling.
I did express from the early days trying to prepare for the return to work, but have stopped because I couldn't be arsed. Will start again when really have to start stocking the freezer.
I intend to keep breastfeeding until at least the point where I wouldn't need to buy a substitute - at least a year.
When I've been out with others, who have been slightly embarrassed and asked me if I'm not, my answer is to rant about page 3s/ nuts/ zoo etc., which people are allowed to look at with impunity. I have a specially prepared mini-lecture about the commodification of the female body and how I think anyone who is uncomfortable looking at a woman feeding is feeling the discomfort of the challenge to that. I am so popular.
OOOH and if you are going to do it, prepare yourself for the long dark night of the soul which is the growth spurts. I very nearly gave in to formula on the 6 week one, because it felt so much like I wasn't producing enough. But having a couple of bottles of expressed milk in the fridge (I was still at keen, 'practicing' stage) really helped.
Good luck darling