Milo Yiannopoulos took aim at 'angry lesbians' after a protester hurled a shoe at him during his speaking event in Sydney.

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The leather slip-on was thrown at the outspoken author during Tuesday's show, but missed its target and slammed into the head of a female audience member. 

'I sometimes wonder about being assassinated by angry lesbians. If that's any indication of their aim I don't think I need to worry too much,' Yiannopoulos said. 

'[There's] no fear of me having a George Bush dodging-the-shoe moment when they can't even reach the second row. You f***ing losers.' 

Four people were arrested for breaching the peace, one for assaulting a police officer, one for affray and one for not complying with direction. 

Banners and placards saying 'f*** off Nazi scum' and 'kill yourself like Adolf Hitler' greeted Yiannopoulos he arrived to denounce Islam, feminism and cultural Marxism. 

Police on horseback were called 'animals' and 'racist pigs' as they kept more than 70 youthful demonstrators to a patch of grass by the shores of the Parramatta River. 

Protesters held signs including a large banner that said: 'First they came for the Muslims and we said, 'Not this time you f***er'.'  Read More

 

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