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The expression is "to pop her cherry". It refers to the hymen - a small stretch of muscle that may, or may not, already be broken through other activities (such as gymnastics, horseriding, etc.) If it is still intact when the woman first has sex (sometimes called deflowering) then the experience may be painful for her and will usually result in some spotting (small amounts of blood dripping onto the sheet - or whatever). It is because of the spotting that the act is referred to as "popping her cherry". As a total aside this was picked up on by the makers of Pacman and they used a cherry as the first bonus awarded to pacman.
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