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all men value being masculine it's rooted in men's evolutionary development 
the shame from femininity or the distress is always present even when it doesn't consciously appear to be distressful because the emasculation is felt even when there is no obvious humiliation involved 
the root of masochism is rooted in trauma when as a young male your gender role was thoroughly ridiculed 
emasculation resonates with this trauma which is experienced as masochistic sexual arousal