My neighbourhood is full of people wearing shirts like that. The first group are poor white trash and crackheads. The second are ironic hipsters (see skinny jeans thread)...
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"I'll never forget the moment during the lovely Alyssa Allure's scene in 'American Bukkake' where the fellow got out of his wheel chair to ejaculate on her face. It was grotesque but had a certain frisson." -Sock