Flange size issue

Sorry for the tmi pic but I'm going crazy over here. I've tried sizes 21, 24, and 28 and have a size 17 flange on the way...I have the same issue with all of them, my areola seems to get pulled in like crazy and causes my nipple to swell up and the skin on my areola double over the base of my nipple. I've tried the measuring to fit on medelas site and without pumping I have a 16mm nipple base...am I heading in the right direction getting an even smaller flange? First time mom so I'm new to this whole pumping thing. Thank you!