with Susannah. I think your adding stress on yourself by unnesessary pumping. Your body produces as much as your baby needs. If he eats more than your body makes more if he eats less your body makes less. After 6 months your milk wont dry out that quickly. I remember getting frusterated but life is too short not to enjoy nursing your son for as long as you can. My last (planned ) "baby" is now 4. I nursed her until she was 31/2. People thought I was nuts. I loved my time alone with her. We tried weaning each other when she was 2 but It was too hard for both of us. Knowing she was my last I was really trying to cherish it as much as I could. Hang in there.......This is just a wrinkle in time. I also agree with Becky, in regards of getting a break. Do you ever get one?
In regards to the sippy cup I always found giving the cup to the baby in the highchair and letting them play with it always led them to figuring out how to drink out of it. Have you tried a straw? I like the ones that come from the fast food resteraunts. If he doesnt suck on it you can always put your finger on the end and give some to him that way.
Anyway, enjoy your baby. And you have support here.
Amee