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Upstate NY Babies
PHOTO Credit: Meryl 
Creating freezer stash
I have been pumping once per day since Friday about 30-45 minutes after the morning feeding. I have been getting a little more each day (3 oz. this morning). I want to start storing some away. When else do you pump? So far I have not had any over supply issues and I really want to avoid that if possible. He almost always eats from both sides.
PHOTO Credit: Meryl 
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Re: Creating freezer stash
I never pumped much, since I wasn't returning to work... but I did need a decent stash because we had 8 weddings to attend the year E was born (3 out of town!) So, I would pump in the morning after his first feeding, during his afternoon nap and around 11pm. Pumping at night seem to give me the best results, when I did it regularly (I would often be lazy, and go to bed earlier, set my alarm but turn it off and go back to sleep!) My body got used to that feeding, and it really helped my overall supply, I think.
A is probably a little too young, and not on that kind of schedule yet though. But, if he is going down for the night at a certain time every night, you might want to try and pump a couple of hours after?
When eve was a baby before i went back to work and after I was back at work, I would pump one side while feeding from the other at the first morning feeding.. I tried to pump after her morning feed too but it didn't usually work out because she tended to be fussy and needed to nurse again, so I always pumped right before I went to bed, which was a couple hours after her last feed for the night (this was once she was sleeping longer stretches at night).
I just pumped for N for the first time because she slept last night and then woke up and nursed on one side and fell back asleep so I had one really full boob! I only got a little under 2oz though. I was hoping for a bit more.
m/c 1/2/08 and 3/12/08
Eve Amelia- Born 2/24/09. 6lb 9.9oz
Natalie Ruth - Born 6/13/11 7lb 6.6oz
I was dealing with a little bit of an oversupply in the first few weeks, so I took advantage of it and pumped a lot, so I have quite the stash already. Now I just pump once a day at night, when we give him a bottle.
I think I would just pick a time during the day where he goes a long-ish stretch and pump about 30-45min after he eats. If you keep it to the same time each day, your body should adjust to meet the demand without creating an oversupply.
DD also would always eat from both sides. Except for when I would pump from the other side while she nursed in the morning. The double stimulation would allow her to get what she needed from just 1 side. I wouldn't do that though if you are going to be pumping right afterwards bc I would be afraid of signalling my body to be engorged in the morning. But if you ever want to save some time in the morning, maybe give it a try....
Also, I would occasionally pump right before bed. So do your last feeding put him to bed. Get ready for bed yourself and then pump. I wouldn't get much out - maybe only an ounce in the beginning, up to 3 at my peak - but I considered it extra and I think it also helped me not get a dip in my supply at night time.
My main stash building came from doing the pump while she nursed in the morning and then once she started sleeping from like 9pm-3am and droppped that 11pm feeding, I still pumped that one for about a month.