I did exactly the same as Phoenix and it worked really well. Cushion to my side or pillow and rest bub on there and in the football grip. Once we both got better at feeding I could do it in cradle position but she always got the best feed in the fottball hold position also the breast didnt smother her then either.

When out I had a few tricks. Nappy bag with a blanket on top can double as a support underneath bub (if your nappy bag isnt to lumpy or I found sitting on the floor (if appropriate) with my legs crossed like a school kid helped support DD better in the cradle hold.

HTH. It will get easier for both of you