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1.
To move in a unobtrusive, sideways action.
"Mandy," I whispered sidling up to her.
by Morgan T. May 01, 2006
 
2.
To dominate a woman sexually. Often to have caused pain with the extraordinary legnth of the penis.
Danny: He has only just met her, that is incredible.

Aaron: I love that guy, he is definitely going to to be sidling her tonight.
by 24jynnad March 28, 2009