I am new to induced lactation, but not to breastfeeding or to pumping, so I'll try to help.
Especially if you have never breastfed, yes, it is going to hurt for the first few days. Some soreness is to be expected. As long as you are not bleeding or developing fissures, the pain is probably normal. Sorry! However, if you can make it through the first week or so, they will toughen up, I think.
Do you have any Lahsinoh lanolin ointment? If not, some people use A and D ointment or something similar. I highly recommend the Lahsinoh, though.
I also have relatively small areolas, and yes, they do get pulled into the tube along with the nipple.
Just an idea: How long are you pumping each time? It probably wouldn't hurt to reduce the amount of time that you spend pumping each session by a few minutes. It is more important to pump frequently than to pump for a long stretch each time. If you end up feeling like your nipples are being pulled off and set on fire, you won't be highly motivated to continue, and like you said- you can't give up! Maybe just pumping for 3-5 minutes each time would be OK for now until your nipples toughen up.
I don't know if you are experiencing more pain because nothing is being expressed yet. Someone else with more experience with induced lactation could address that. Although I breastfed 3 bio. babies, I am new to induced lactation and I'm only on day 5 pumping, so I'm right there with you. Please let us know how it turns out. Hang in there- things can only get better from here.
-Jenny M.