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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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