Just a thought...
Smoking a cigar or smelling cigar smoke triggers a normal, gay, wallflower type guy to become assertive, outgoing, maybe even a bit cocky and act more masculine, if not hypermasculine. Perhaps over time, encouraging him to be more interested in cigars and being this way all the time, as well as maybe other changes.
If anyone's up for that challenge, I'd be interested in hearing. I'm definitely interested in something like this and have chatted with others who would be, too.