Definder - what does the word mean?

What is bogey on my tail?

an ugly chick who follows you around, speaking to and flirting with you both blatantly and incessantly, thus blocking your cock in the worst way possible.

douche 1 "dood, i'm never gonna get laid with this bogey on my tail."
douche 2 "brahsef, you either gotta shake that bogey or we need to go to a party with clear skies cause she's killing my game by association."

disclaimer: obviously douche bags don't use such profound sentence structure or vocabulary, but you get the point.

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bogey on my tail - video