He pressing me like button-downs on a Friday night

from Young Money (Ft. Lloyd) – BedRock Lyrics on Rap Genius

Meaning

“Pressing” is pursuing aggressively, but you also “press” (iron) a “button-down” before heading to the club on a Friday night, when the dress-code is “Dress to Impress: no Timbs and no hoodies”

“Pressing” could imply sexual intercourse as well. This would make sense, since she ends up “coming off the top.”

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