When my milk come in I had extreme engorgement and bub couldn't attach at all. We had to massage my boobs for 5mins before a feed as well as ice packs.
I agree with Tanstar - a slight adjustment in bub's position could make a world of difference, and if your boobs are quite large you may need to hold them up... I still have to 4months on!
Hope you work it out soon... but good work and thumbs up for asking for help!