I have actually know a couple Americans that visited the Dominican Rep, and bought Cubans, COHIBAS to be exact. But they took off all the labels and put the cigars in a different box or bag. Then they mailed the labels to there house address later during there vacation. Dont know how it worked out, but I dont see how customs could prove anything. Its maybe a great way to smuggle legally.
I suggest bringing a empty Dom Rep cigar box before visiting anywhere and smuggling them in there. Should work !