Though the snipMate plugin provides mirroring (i.e. copying the typed contents of the current placeholder to another position), it has no ability to run transformations on it (and this is needed here: you want each typed character to be translated into an asterisk). This should be possible with the more modern UltiSnips - The ultimate snippet solution for python enabled Vim plugin.
Nonetheless, I would ask you to reconsider your approach to "clean" commenting. If your style requires special setup with a custom plugin in a particular editor, chances are that your colleagues / collaborators won't have the same setup, and are therefore likely to ignore your scheme. That could be even you, when you're forced to make edits on another computer / editor. IMO, you don't lose much in beauty, but gain a lot in maintainability if you stick to simpler formatting, like this:
/****************************************
This is a comment
****************************************/
In particular, dropping the trailing, right-aligned *
enables you to quickly reformat comments with gq
.