I have been playing around with this idea. I realize that this is an old thread but here is my method works well. With better machine control I would eliminate indentation by the needle. But it was pretty simple. I finished the leather first. Dyed it brown and put a finish coat on it. I used fiebings tan-kote. I stencilled the tattoo using the method for transferring a pattern for regular cutting and stamping. I put a heavy layer of vasoline and tattooed. Wiped with damp rag applied more vasoline. Continued. After I was done I scrubbed the vasoline off. Applied a second coat of the tan-kote.