cut contour shapes

I would be grateful for some help regarding bleeds and cut contour lines.

I am working on a project with various different contour shapes (see sample). Each shape has 2 different coloured contours. On top of the shape is another shape acting as a product header. This header has a different colour from the product object. At the moment I have grouped both these objects as they are going to be filled with printed content on front and reverse side and I must be sure to have a 100% alignment front and back.

My questions:

How do I include bleeds as well as a cut contour line for both objects? With the attached sample the letter A has an outer blue contour of 1.5 cm. How do I include the necessary bleed? Command 'outside boundary' doesn't work because I lose the cut shape within the design. Using a third contour "inside" blue contour also doesn't work.

I hope the description of the problem is clear. Can anyone help? Many thanks. Sonny

cut contour shape