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I had a girlfriend who cried the first time we had sex, and not in a good way. It turned out that she had been raped at 12 yrs old and it caused her to relive that, but I didn't know that at the time so it freaked me out pretty good.
Myself, never, sex is just not something associated in any way with anything that would cause me to. My wife is the same way, she either gets playful or touchy/cuddly or just demands more, but never crying.
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