Hi Neptune!
Oh your nipples - you poor thing! I don't know whether you want bf advice today, but sometimes it does start like that, and yeah, they don't tell you, hey? Only that it shouldn't hurt - but it bloody well does for some people! DS took 11 weeks to get the hang of latching on properly so I wasn't in pain - despite being assured by 3 different LCs that he was attaching beautifully and my technique was perfect. Nipple shields got me through.
Anyway, expressing what you can in the meantime is a good compromise. You just do what feels right for you and your lovely little boy.

Must go, DS is playing monkeys with his auntie. so cute.