Hi Lisa,
I did sidelying similarly to what you describe, with my pillow between
my shoulder and my head, and the baby on his/her side facing me.  It
took about 6 weeks before I could comfortably feed sidelying with my
firstborn (big Cesarean incision 'cause he was breech and stuck) but I
was immediately comfortable with my secondborn (homebirth with a midwife).

Some other tricks I've learned from working with other moms:
Moms with large breasts sometimes do better using the "rolldown" method
and feeding from the upper breast- Baby is placed farther away from mom,
either fully or mostly on his side, and further down toward her feet
than with the typical sidelying position, and mom rolls toward her
belly, supporting her body on her upper knee (similar to the way many
pregnant women sleep).   The breast and the baby's mouth connect
somewhere during this roll, or else mom can snuggle baby in for a deep
latch once she is comfortable.  Most of the trick is getting the baby's
body low enough so that one still has an asymmetrical latch (baby should
always have to extend the head a little to get to the breast).  Mom can
snuggle the baby in with her upper arm, or use a rolled up blanket to
hold him in place.

Moms with smaller or firmer breasts may use a normal sidelying position
by just rolling a little more into the mattress to bring the nipple just
about a half inch above the mattress, where baby can grasp it.

Mom's who need to wedge or shape their breast can use the upper
(topside) hand to shape the breast, and the arm coming down from under
the pillow (the lower side arm) to snuggle baby in when he opens wide.

When I make home visits, I like to offer to show the mom sidelying
positions in her bed.  I agree that this is "breastfeeding survival 101".
Catherine Watson Genna, BS, IBCLC   NYC

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