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This stands for Outlaw Biker. An Outlaw Biker is the type of guy the girl of your dreams goes and fucks because you're too much of a pussy to take control of your "relationship" with her. Most of the time he is either unemployed, has a substance abuse problem, or has callous "dating" habits. A combination is certainly possible, too. Commonly used to conjunction with "IW" or "intellectual whore" which is exactly what you are if your dream girl fucks OBs then cries to you about it.
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