I found that putting some nipple balm or coconut oil on my nipples before pumping helped with the friction from the flanges. Just make sure it's the type you don't have to wash off before you feed (I use Motherlove brand).
Yes! Pumping is actually worse,than breastfeeding (the initial latch is all that hurts). I'm hoping that pumping is just new to me and it becomes more comfortable in time...
Once you get used to it it's not painful. However if you have nipple damage it'll keep hurting. Definitely use a nipple balm that doesn't have to be washed off and check with your pump brand on how to make sure your pump flanges are the correct size. You also don't need to pump on the highest setting. I started low and then went to the highest comfortable setting.
Make sure you don't need a different size flange. .. if more than your nipple is getting sucker thru you might need a smaller size. Check with a lactation consultant they can make sure you are using correct sizing and pumping correctly. It shouldn't be painful unless maybe your nipples are blistered from the first week or so of BF.
Re: Pumping Question
You also don't need to pump on the highest setting. I started low and then went to the highest comfortable setting.