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At 13 or 14 by my best friend at that time. He was always sagging, wearing snapbacks, sneakers and calf socks etc. and I thought it looked hot. I dressed quite nerdy at that time and it was he who told me once after we "did" it that I should stop looking like my mother dressed me. So I started slowly by wearing caps sometimes, wearing hoodies and baggy jeans and also sneakers and nike crew socks later on. When I had enough courage I started slowly sagging and it felt and looked great. The sex was definitely better after my transition from nerd to sagger