I did a lot of propping the first few months. As the baby gets bigger and you both get better at it you will need it less and less. Consider trying different positions and see if they work better for you. I also learned how to nurse in a sling (Maya Wrap type) and I would nurse my DD in that while wondering stores. It helped keep her close to me and I just needed one arm to support her head once she was latched on.
With my first child I seemed to rely on the Bobby way longer than I wanted to. It was the "crutch" I needed to keep me comfortable. It did get better though. Practice, practice, practice.