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2.
Vaginally challenged is a word to define a homosexual male who had made the conscious decision to become gay. There is no medical fact, statistic, or case proving that you are born homosexual. It is a choice just like everything else in this world, just like I choose to have sex with a female.
John, Mike, and Steve all went to the gay porn store because the doctor has diagnosed them with being vaginally challenged.
by Cameron Seisan June 07, 2007
 
1.
Anyone who is considered bad with women.
From the book I Hope They Serve Beer in Hell
Girl - So you're single?
Guy - I prefer 'vaginally-challenged'
by whodunnit? November 18, 2010