A sexual maneuver whereby a female virgin demands that she and her partner engage in anal sex only, because she believes that she will remain a virgin if she avoids vaginal intercourse. The man, who if a gentleman, complies without objection.
Sally's says she wants to wait for marriage. She wouldn't let me hit the skins, so I gave her the Virginia Gentleman instead.
by Dan, Daniel, Matthew January 16, 2006
When a drunk friend asks for a glass of water while being extremely intoxicated and you hand them a glass of vodka.
Lisa was puking her guts out and Stevie kindly gave her a Virginia Gentleman.
by DooDooSoup July 19, 2015