Yes. I fed DD (my second) for over 7 months, stopping by choice when I returned to work.
Some of the things that made a difference:
(1) Read a lot of the breast-feeding boards on here, so had a lot more knowledge.
(2) Contacted a (private) breast-feeding counsellor before the birth. She came to my house, showed me a video of a baby latching itself in the bath, gave me various written information, listened sympathetically to me spouting about my horrible experiences with DS, promised to come around when DD was born if I'd like her to.
(3) Watched a DVD - mine was Clare Byam-Cook's Breastfeeding without Tears. Has a section of her taking about 10 minutes stuggling to latch on a baby, but getting there in the end. Personally I found that an eye-opener, and actually quite supportive.
(4) I didn't expect it to work second time, whereas first time I'd been "very determined" that it would. Thus I was a hell of a lot less anxious.
(5) DH supported me for the first few days / nights. Helped me to latch her on, looked at the latch etc. (Instead of turning away and sighing loudly because of all this nonsense that was disturbing his beauty sleep.)
(6) I had some confidence in myself. So when became very sleepy on day 2 (more than 12 hours), I expressed colostrum and gave it her in a syringe. And ignored the midwife who was asking about the amount DD had had: "You said 15mls? 1.5 mls? I'm sorry, you mean ONLY 0.15ml???!" (Shut up woman, I worked hard to get out those 20 drops..)
(7) DD was an easier baby generally.
For the record, I can think of 3 other friends who didn't succeed b/f their first but tried with their second. Two of them succeeded in feeding their second for as long as they chose. The other gave up after 2 weeks, due to mastisis (which she had repeatedly 1st time around).
If you decide to go for it second time - good luck.