Metaplastic homonyms like this one are a favorite of the Metaplasm team.
"One that I heard my brother use a number of years ago was 'weary', as in 'I'd be a little weary of doing that.'," Steve Terry explains. "Of course he meant either 'leery' or 'wary', but the inadvertant portmanteau was interesting in that 'weary' is something you might become if you were to do something you were leery or wary of."
"Exactly right Steve," says Metaplasm staffer, Tim C. "I'm always weary of a trip to the in-laws and by the time the visit is over I'm weary from my trip to the in-laws." (Originally posted December 8, 2003)