Alrighty then, assuming you've installed the Cuttin Master proerly and created a setup for your plotter...
Set up the image to be printed in Corel.
Create a new layer, optional but easier to explain.
In that layer create the path around the image that will be the contour.
In that layer draw a rectangle around the image and its contour path. Leave maybe 1/2" or so margin between this bounding rectangle and the image. Make the rectangle a rational number of inches, preferably an integer, wide and high. This is a bit of a trick they don't tell you in the documentation.
Make sure the bounding rectangle is the top object in the layer and is selected.
Invoke the Corel application launcher, the little rocket ship icon, and select 'Registration Marks'. Select 'Graphtec Type 2 Automatic'. Select the 'Convert Rectangle' option and press 'OK'. The bounding rectangle of known dimensions will be replaced by 4 registration marks.
Print the layer with the actual image by whatever process you use. Make sure the registration marks print with it. Leave at least 3"-4" of media at the end of the print and 1"-2" at the beginning. Leave sufficient side margins or 1"-2" as well.
Load the print in the plotter in exactly the same orientation as it was printed. Load it as square as humanly possible.
In Corel hide the layer with the print image and invoke the application launcher. Select Cut/Plot. The cut/plot dialog is displayed. Set up whatever parameters you fancy and send the job to the plotter.
A dialog will display telling you to position the blade over the first registration mark, that would be the lower right one. Do what the dialog tells you. The plotter should then read the marks and take off cutting the contour paths.
If somehow the plotter doesn't successfully read the marks, you can save the day and do it manually. That's a topic for a different conversation.