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In practice, the phrase is targeted at an audience with a "little sister" fetish (imouto complex). The "squeezing" is a euphemism for intimate or dominant-receptive physical interaction. imouto bitch ni shiboraretai link
While "imouto ni shiboraretai" may seem unusual or even provocative to some, it has become a significant aspect of Japanese popular culture, with a dedicated fan base and a growing presence in various forms of media. This media is intended for adult audiences