Mine was 2009 and he was a punching bag. Other than that haven’t encountered many until after Covid lockdowns when people were fucking mental.
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Furry was around 2013, walking down the steet and someone had a furry tail sticking out of their pants. Had no idea what it was.
Tranny? Before the tranny movement there were lesbians that dressed like men, that was the precursor but not really trannies. Probably around 2014 I saw the first man dressed like a woman.