Mama, I feel your pain. What you're describing is extremely similar to what I felt in the early days with my daughter. We stuck with it and it did get better. She was about 6 weeks old before I finally had an "aha" moment and really had a good time with breastfeeding.
For the first 3 months, give or take, your supply is hormonally driven. Once you start hitting about 10-12 weeks, our supply becomes driven by demand. It is absolutely imperative that you have the little one on the breast as often as possible for as long as possible to ensure that your production doesn't take a dive. Any time the baby gets a bottle, you need to be pumping to replace that as close as possible to when baby gets the bottle.
Not having pain when pumping is a good sign - it means that the pain issue is probably not thrush. Our pain started at about week 3 when we weaned from a nipple shield and it lasted about 2-3 weeks. Some of the feedings just started hurting less and less. There's definately a tougheing up of the nipples that goes on during this time period.
You should be able to break the baby's suction easily, no matter how strong the suck. What I do is stick my finger in my mouth first to make it easier to slide into DD's mouth. Then I slide my finger into her mouth, between her gums, and hook my finger around my nipple, and then it just pops out without pain. It's entirely possible that if you pulled out without breaking the suction you may have a bit of bruising in the nipple that's still healing.
I used a lot of lanolin in the early days to help with pain. And make sure to check carefully over your nipple for cracks.
Hugs mama. There's a lot of learning that goes on for both you and baby in the early days. There is a great community on Livejournal.com called "breastfeeding" and there's also a community called "adopt_a_mom" that pairs you with a mentor to provide one on one support and answer questions. Having someone to turn to who had been there, done that, was really helpful to me in those early days.
Sticking with breastfeeding is one of the things I'm most proud of. DD was exclusively breastfed to 6 months when we started introducing solids. At 2 weeks shy of 1 year, she is still breastfeeding daily and we plan to let her self wean when she is ready. I really believe that our nursing relationship is worth all the pain and all the tears. It's so easy to never have to worry about bottles or forgetting formula. Her milk is always with us, always available, always the right temperature, and always a comfort to her. I just wish I would have discovered nursing tanks a little earlier.
Hang in there mama, it gets better.