I changed only one word in 'Sandwood Down to Kyle' to put the narrator (me the singer) and the person met in opposite places in the story. This allows the 'person met' to eulogise parts of the West of Scotland which I felt unqualified to do as me.
But you can sing as an actor. If you hear Alan Prior sing 'The Star of the Bar' you'll believe He was the actual man in the story but that's his skill as a singer.
You couldn't cross dress that song. But many you could with the care I think you intend. Been done before.