Top Definition
When a guy is about to hook up with a girl but is too much of a bitch to actually kiss her so instead he skips to tenderly and awkwardly massaging her boob whilst pretending nothing is happening and more often than he pretends that his attention is elsewhere by looking off into the distance.

Crossing the mound comes from the proverbial baseball field of sexual progression, in this case the guy runs straight from the batters box to second base thus running over the pitchers mound on the way. (Hence crossing the mound)
Laura: "Hey Jessie I heard that Steve was crossing the mound with you last night."

Jessie: "Yeah he's got no balls, I had to kiss him first."
by JkJ121 July 24, 2009
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