Hi i breastfed my dd until just before her second birthday.
From the time she was 9mths i had begun "planning" on stopping. But no matter how much i tried to prevent her having a feed, she'd find a way. The older she got the stronger she got at ripping my clothes off me until i fed her!
I went through periods of wanting to stop, and then periods of thinking oh well, lets carry on a bit longer. From one year onwards she was only feeding at nighttimes because i did make an effort to cut out days, just by not cuddling her, and distracting her as soon as i knew she was "digging" for the boobs. I did substitute with bottles sometimes if i couldn't distract enough.
Finally in the last few months before her second birthday, i began telling her boobies were for babies and she was a big girl. If she tried to feed at night, i would laugh and say you're not a baby - she used to find this funny and then not feed, just tease and then shake her head and say i'm not a baby, don't need boobies.
Believe me it was a very gradual process! But she no longer ever requests a feed.
Now i know it was possible to give up in the end (before she got to school) i think i would relax more now with a next child and let them feed until two as well. I think first time round i felt under a lot of pressure from health visitors, family and friends who made comments about my breastfeeding and joking that she'd still be doing it at school.
Next time i'd have more confidence, knowing what a very secure little girl i've brought up and i don't see any reason why bf until 2 is a negative experience (apart from maybe frequent waking in night still!!).
I was fortunate to not suffer with mastitis, so i don't know how best to cope with that, expressing sounds like a good idea.
But really i wanted to let you know my experience. And if you have are choosing to give up because that seems to be appropriate in society - then don't let it be your only reason. I think it is wise to start discouraging daytime feeds, but you can afford to do this really slowly so that hopefully you won't suffer as you have been.