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Medela- Flange Size Issues- Breast Pumping Question.

I use the Medela Swing breast pump and I absolutely love it, however, I immediately had to go out and purchase larger sized flanges.
The Swing came with 24mm flanges which were much too small, so I went to babies r us and got some 27mm, which turned out to be too small as well. I finally went back and got the 30mm flanges and they seemed to do the trick for a while but now my nipples are sore and red.
I went to the doctor today thinking that perhaps I had an infection, but she said that it's just irritation from feeding and/or pumping frequently.
I know that there has to be a more comfortable way to pump.

I feel that with the 30mm flanges my nipple still touches the sides of the flange while I'm pumping and so I think I have irritation from the friction.
The next size of flange after 30mm is 36mm, which seems like a big jump to me, and I would try it anyways except that babies r us and every other store in my hometown only carries up to 30mm :(

I have spent tons of money on medela products at this point and I cringe at the idea of purchasing another flange at an even more expensive online price (which would likely include shipping costs) when it may not even be necessary.

Has anyone else noticed that their nipples are rubbing against the sides of the flange? Is it normal for nipples to touch the sides to some extent when pumping or should only the base of the nipple be tight to the sides? I have seen diagrams showing how flanges should fit but they don't seem to help my understanding.
Also, does anybody have any ideas as to how I can avoid having sore, pink, sensitive nipples from pumping if I do in fact have the right size flanges? 
Has anybody gone up from 30mm flanges to 36mm and found that the switch made a positive difference?
Where can I order 36mm flanges online if I absolutely have to(I live in Canada, as a sidenote)?
And finally, do you think that if I contacted medela via telephone that perhaps I could convince them to send me a sample flange in the 36mm size? I have read online about some women who have been able to receive free flanges from medela when they were having flange troubles and could not locally purchase the appropriate size.

Any advice would be greatly appreciated!

Re: Medela- Flange Size Issues- Breast Pumping Question.

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    Coconut oil can help things slide more smoothly. Are you sure it's your nipple rubbing? Or is it your areola. It's normal for a little bit of your areola to get pulled in. You can get sore nips from too small AND too big.

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    The LC nurses at my hospital had a measuring guide for flange side. My nipples were sore from pumping but it wasn't the flange I was pumping too long. Not more than 20 minutes I was going 30. Also if the suction is too high it can make them rub against the side too much. I agree with pp about lanolin and coconut oil. I also would express milk onto the nipples and let airdry after pumping and that helped. Good luck to you.
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    Your nipple should not be touching the sides, no. That would cause the pain. Suggest ordering the larger flanges and using lubricants as PP said in the meantime.
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    I have the 36 mm flanges that I've never used that I would be happy to ship to you. Pm me if you're interested.
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    I agree with PP -- the diagrams don't make much sense to me because part of my anatomy always rubs the sides of the flange, but it doesn't cause discomfort and my milk output is very good, so I just go with it. 

    BUT, if you're having discomfort, I would highly recommend you try Pumpin Pal inserts. They fit right into the Pump in Style (in place of the standard flanges) and they are so much more comfortable. They're actually shaped more like a baby's mouth, too, on an angle, so it cuts way down on friction. When you buy them you get 3 sizes so you can experiment with which one works best. 
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