Did you use a thimble? I couldn't hand sew without a thimble; my fingers would get too sore. Also, how large was the needle you used? A thicker needle with a big eye will be harder to push through the fabric than a finer needle with a small eye.
Here is my favorite video on how to machine-stitch binding on both sides:
http://www.youtube.com/watch?v=wprg5...os=_w0gFlqkSgE