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When I gave up my ass cherry (I was in my 50's) the tears started a little after the initial squeal, writhing, leg kicking, etc - when he completed the insertion to full depth. I think the sobbing helped me deal with the pain as he deliberately and methodically took his pleasure, and showed me how a woman feels when she is popped and split for the very first time. I had mostly stopped crying in time to receive his natural insemination.
It was embarrassing and humiliating to cry like that, but very much a significant part of getting fucked for the first time.
It was embarrassing and humiliating to cry like that, but very much a significant part of getting fucked for the first time.