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On the easy side (right side), I do cradle hold and side-lying... but honestly he will latch on before I'm ready and get a perfect latch from anywhere. EASY!
On the painful, horrible, I-almost-want-to-quit left side, the best position is... where he is pretty much sitting straight up on my leg, and I am sitting on the edge of the couch with really good posture. I also do the cradle hold on the boppy with his legs between me and the boppy, not up on top of it (better angle, I guess). Sometimes I do football hold. I cannot do side lying on this side. I also do some funny random positions involving sitting on the ground and using my left leg to help hold him--this is the least painful.

I hate the cross cradle and never get a good latch with it.

We started with cradle, added football when I started pumping in the morning. Then added laying down when he still wasn't sleeping through the night or gaining weight. Them we learned to nurse in the carrier sitting upright. At 14 months I think the only thing we haven't done is upside down. Mastering the sitting on me and nursing has been a godsend.

Football was my go to when she was smaller, it was so easy and it only took one hand. Now I just mix it up, cradle, cross cradle and side-lye. I lay down to nurse first thing in the morning (when I still want more sleep!) and if she's super fussy and fighting her nap, and I'll just leave her to nap on my bed.

@BabyBoecksMom: ditto!

I'm trying to get her to do the side lying but it's only worked once. hehe

Football when he was super small, then cross-cradle almost exclusively. Now we can do cradle as well, from almost any sitting or standing position (which is great when he wants to nurse and be rocked/walked around). Side-lying worked really well at first, then only on one side, and now on both sides again. We can do the baby-on-belly thing only on one side, but he LOVES it. He's been really fussy while eating lately (hello, 4 month development hurdle!) so we've had to get creative.

I do sooo many positions!!

My favorite while learning to breastfeed was definitely football hold. It helped with his breathing too because my breasts were so big compared to his tiny little face.

It wasn't until recently that I've started using cradle hold.

At 4 weeks we mastered side-lying, and we do that at night. I get him from his crib, go back to our bed, feed him til he's asleep again and put him back in his crib (okay okay, I admit to not always putting him back lol!!).

We actually just tried the position where I lay on my back and he is on my chest - it was pretty funny but it worked. We did in on my bed.

And we also have used the position where he sits on my lap and feeds sitting up. It's the most difficult for us now though because he can't sit up on his own and honestly my breasts are so big I have to hold both him and my breast or else he can't keep it in his mouth.

@Coco Bee: haha, I have the same issue with the sitting straight up one, but I still like it because it hurts less.

I mostly nursed Lo lying down. Sometimes used the cradle hold when we were out.

I only use cradle. It just the easiest for me and baby has no complaints.

Cross cradle is the easiest for my large boobiness. I used football with Toddler Girl until she got to long and I can nurse Wonder Baby side lying in bed.