Randnmom... When I was pumping for my bio kids, I did find the massage to be incredibly helpful... I got sprays and it really sped up my pumping sessions at work. You can definitely do massage while using a double pump. While massaging the right side, support the left "pumper" in the crook of your left elbow while pushing against your breast a little to keep it well attached and pumping. This frees up your left hand to hold the right pumper/bottle. Then use the right had to massage. If you're losing suction then you're probably getting too close to your areola and breaking the seal. Massage from the top of the breast only to about halfway down. Also, when the baby latches on, it will take a large portion of your areola into its mouth, not just the nipple. So you actually want bigger cones to pull more of the whole nipple-areola combo into the action. Of course if its too much, I suppose you could actually constrict the ducts and prevent the milk from coming out. Play around with the different sizes and see which works best, but I always found the bigger ones to be more effective (and I actually have pretty small nipples). I hope you don't find this condescending, like you couldn't figure this out yourself, I just know it took me some time to figure out how to coordinate the hands, pump, bottles, etc. and I would have liked some input!!