Hey there...I'm a new member to this forum but have been reading intensely for the last couple months! I've noogled on and off for the last 5 years, had 2 babies in between and seen results especially with it helping my boobies recover from breastfeeding. 
Anyways...my personal opinion for you would be try Large cups. If you get cups too small, they'll help give you some swelling on your actual boob, but won't do much for building the tissue on top. I don't know much about the protective rings, tried them once and found them to be bulky and annoying lol. The key thing I remember when starting is to start slow, a few minutes at a time and be gentle until your skin adjusts to the pressure and your chest gets used to the cups. It feels funny at first, almost painful like wearing a thong for the first time ha ha! Once you get used to the feeling and putting them on, you'll find you can get more aggressive about pumping. As for the red rings that are there afterwards, I took the advice from this forum and only pump 10-20 minutes at a time, then massage for 5-10 minutes then repeat pumping. Barely any red rings when finished! But plenty of swelling, yay!
I personally don't use oil or any basic lotion from the store that has mineral oil in it. I would get acne or red dots from say baby oil. I don't like using even natural oils because for me it makes my skin feel "tight" or like I can feel it stretch...again, this is just my thing. I prefer natural lotions or butters, like Burt's Bees! I'm currently using their Shea Butter cream. Love it...
Hope this helps you somewhat, goooood luck!! Noogling rocks!

Anyways...my personal opinion for you would be try Large cups. If you get cups too small, they'll help give you some swelling on your actual boob, but won't do much for building the tissue on top. I don't know much about the protective rings, tried them once and found them to be bulky and annoying lol. The key thing I remember when starting is to start slow, a few minutes at a time and be gentle until your skin adjusts to the pressure and your chest gets used to the cups. It feels funny at first, almost painful like wearing a thong for the first time ha ha! Once you get used to the feeling and putting them on, you'll find you can get more aggressive about pumping. As for the red rings that are there afterwards, I took the advice from this forum and only pump 10-20 minutes at a time, then massage for 5-10 minutes then repeat pumping. Barely any red rings when finished! But plenty of swelling, yay!
I personally don't use oil or any basic lotion from the store that has mineral oil in it. I would get acne or red dots from say baby oil. I don't like using even natural oils because for me it makes my skin feel "tight" or like I can feel it stretch...again, this is just my thing. I prefer natural lotions or butters, like Burt's Bees! I'm currently using their Shea Butter cream. Love it...
Hope this helps you somewhat, goooood luck!! Noogling rocks!