We've been together for 5 years and married 3, we had sex about two months into our relationship, and about the fifth time on, he was pleasing me everytime. You always have a time here or there that isn't as great as you'd like, but thats normal
About four months. I hadn't had an orgasm during intercourse in my prior sexual encounters and really just needed to be comfortable with someone. He was patient and didn't pressure me, and now I come practically every time.