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I had a similar issue with breastfeeding. I came to dread it. I don't know why, but I always got the worst feeling when my baby nursed or I pumped. It just didn't feel right to me. My advice would be to see if the larger cones work any better, and then see if you feel different once your little guy is up to nursing on his own before you make any decisions.
My son was 8 weeks early and has been on a fortified breast milk diet since. I've been pumping for him and using Similac's Neosure as perscribed by his pediatrician, but now that he's gaining weight at a wonderful rate and has been given a great bill of health at his one month check up his doctor said I could try nursing with him and slowly wean him off the fortifier.
We tried this afternoon and I was amazed at how much it HURT! Were we doing something wrong or is it normal for me to experience pain as we learn how best to coordinate our efforts? Does anyone have advice? After about half an hour of us both getting frustrated I gave him the bottle and resolved to try again tomorrow and my nipples did not stay sore for long. I would REALLY like to breastfeed my son, but if it's going to be that painful then I'll just continue to pump and bottle feed him.
You might want to let the lactation consultant check his latch. It shouldn't have really hurt the first time you did it. They definitely get sore (and I mean VERY sore) for the first few weeks, but I never remember pain those first few tries. Instant pain on the first try tells me something wasn't right.
He should have his mouth wide open and look like he is trying to swallow your breast. Your entire nipple, areola and all should be in his mouth. If he gets just the end of it, you will experience much more pain than necessary.
Dont feel llike a failure i so desperatly wanted to breastfead my baby girl but during labor i had to have and emergency c section and for some reason my milk didnt come in untill 8 days later i was forced to put her on formula and i felt really bad and felt like i wasnt giving her the right nutrition. But come to find out that formula was a better choice for her any way. so dont feel bad you were doing just what you were supposed to be do doing sometimes these things just happen.