It sounds like your corking device doesn't work correctly for your purpose.
Check with your local home brewing store to see if they rent floor corkers. These have a multiple jaw compression ring in the center that squishes your cork such that it fits in the neck of your bottle, and then a small push rod on the handle that pushes the compressed cork smoothly and completely into the neck of your bottle without any risk of breaking off.
For example:
http://morewinemaking.com/view_product/6300/102727
http://morewinemaking.com/view_product/19436/102727
http://morewinemaking.com/view_product/6174/102727
Or, by hand, this is the best option:
http://morewinemaking.com/view_product/19435/102727
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