I had the same issue with my little girl (now 19 months) I breastfed and had to use a nipple sheild for the first 5 months, so I thought sh'd be used to the silicone feeling and take right to a bottle. We tried about 5 different types of bottles...FINALLY I found the Sassy/Mam Ultivent bottles online at Target, and at the Sassy website - I even got some off Ebay.
http://www.target.com/Sassy-MAM-9-oz-Bottles-Colors/dp/B0...#
http://www.sassybaby.com/category?cattype=category&ca...
We also used that same brand/shape of pacifier, and she still loves those. They have a specially shaped orthodontic nipple - it is slightly flattened and bigger at the tip than it is closer to the bottle, rather than a perfect cylinder like most bottle nipples are. She did so great with those, I think because a real nipple flattens in the mouth, just like those. Another plus is they are easy to get clean, since they come apart in 5 pieces, and they have a vent in the bottom to prevent bubbles/gassiness....we rarely even had to burp her, after we switched to these! In the reviews, lots of people complained about them leaking, but I only ever had leaks, if I didn't take the time to put them together right....and by time, I only mean a few seconds, to make sure the nipple and the silicone seal in the bottom were in straight, and the top and bottom were screwed on tightly. They also have no BPA, and are dishwasher safe! The one and only drawback is that they don't fit in most average bottle warmers....we just used the old fashioned bowl of hot water under the faucet to warm breastmilk, and just made formula with warm water in the first place.
I will start with these bottles for this baby - I am 10 weeks pregnant!