Idiom that refers to the moment when a person with unconventional manners or mode of life feels comfortable enough to be himself/herself in front of others. It's when we allow ourselves not to be ashamed of our own wicked personality.
The time's come for you to let your freak flag fly and show everybody who you really are!
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To walk with your penis out. This can be either completely naked, with only a shirt on, or with everything on but ur member hanging out of ur fly.
Male exhibitionists like letting the flag fly.