I went back to work when dd was 3 months. i pumped 3x or even 4x a day until she was 14 month or so. then slowly got down to 2, then 1, and now (she's 16.5 mnths) I rarely pump during the day.. (i just got lazy and she doesn't drink the ebm anyway, and my supply is just fine for nights/mornings/weekends)
anyway, to answer your question, my bosses were all fine with me pumping. I work for a large company, but in my dept. I am the only mom i know of that ever pumped
well, there aren't many women here. I used our ladies' room - the last stall was big with an extra chair and its own sink - and our bathrooms are cleaned twice a day (and like i said, there aren't even many women on the floor) so that worked out fine. then I just used the common fridge. I've had to go on several trips. for day trips, my boss was very accomodating, he knew what I had in my small carry-on bag
and even made some jokes about it. one time on the flight home my carry-on started to leak and he helped me find a plastic bag to fix the situation
I have gotten a few "how long are you going to keep that up for", but every time I said "well, something I didn't know about before dd was born, is the the World Health Organization says at least two years" so that usually ends it.
It can be tough, but I think it is so worth it!!!!