When I squeeze my nipples I get a clear, somewhat sticky discharge during certain times of the month. There's no pain, and no change in my breasts. My mother had breast cancer when she was 38 years old (she's now 63), and I worry about it. I'm 41 years old. Thoughts?
First, please read our post, Nipple Discharge: When Should I Worry? This will give you detailed information about what's going on, why, and what to do about it (if anything).
Thankfully, what you describe isn't a typical breast cancer symptom. Clear or milky discharge from both nipples, that only happens when you squeeze your breasts (and only at certain times of the month), is almost certainly hormonal. As you age, your hormones start to fluctuate a bit; and you may see a number of changes related to your female hormones as you head through your 40s and get closer to menopause.
To answer your question about whether you need to check with a doctor: yes, but not for this discharge specifically. You should talk to your doctor about starting annual screening mammograms, recommended by the American Cancer Society starting at age 40. This is especially important since you have a family history of breast cancer, which means your own risk is higher than normal.
If you've had a breast exam and mammogram within the last year, you don't need to make a special appointment about the discharge unless it becomes spontaneous. And it's best not to squeeze your nipples to see if the discharge is there; it only irritates them.