Stroking and image not created in Illustrator

I have been a Photoshop hobbyist and enthusiast for years. Now I own a  printing business to put my hobby to work. This has forced me into the  world of Illustrator for our printing and cutting machines. Although I  am very comfortable with PS, Illustrator is giving me fits. One of the  key things is making "Cut lines" in Illustrator to send to the cutting  program. Now here is my dillema, all of my images I have made are in  Photoshop. To make these cut lines I have to stroke the image. When I  bring a picture into Illustrator I can not get it to stroke that  picture. It just strokes the box around it, or unless I draw a circle  or shape around it and stroke that shape. Please refer to the picture I  have attached. The first one is a decal that we initially made. The  second is the image that I want to stroke for cut lines do I can just  have that as a decal without the white circle. Any help would be  appreciated.

Hello Dimitri try this.
Why not use the pen tool and draw a stroke around the image and make a clipping mask of the outline, like you would in Photoshop, then increase the outline to your requirements.
See rough example below, with outline.
TREX

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