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The utility applications that come with opencv as of vers 3.0 don't support generating positive sample from multiple positive image.

To accomplish this you would need generate a script that loops through all your positive images and for each one, run it through the opencv_createsamples app and tag each generated vector file with a unique name. Once this process is finished you would need to, as mentioned in the other comments and answers, stich together all the generated vector files into one big vector file for use in training.

Having said all of this you might want to check out this page and this page.

The author of the first linked to page has create scripts that accomplish what i described above.