K.D.
Hi M.
My son and I had the same issue. What my sitter used to do was hold him in the same position that I held him when I breastfeed him then she stuck the bottle in his mouth. It was a bit akward at first and did take a few weeks to smooth out but it worked eventualy. My husband also put on my robe and held him the same way and that transition was a bit smoother.
Good luck
Hope you find a solution that works for you
K.