One girl I think
almost cried from pain. She was an Asian with a very tight pussy, and I have above-average girth. We went at it about five minutes missionary before she orgasmed (lol), pushed me off, and laid there with her legs shaking like crazy, telling me to "give her a minute" and that "it hurts". It was OK though cause she orally aided me in finishing myself off.
Only one other girl has ever cried after sex, but this was after we'd fucked several times over the course of a month. At the time, I was actually in a long-distance relationship with another girl (we're broken up now), and though we loved each other dearly, it had been six months since I'd had any, and as a bit of an addict, I couldn't keep going on like that. I ultimatum'd my GF into a PHYSICALLY open relationship (with some caveats, like not with anyone we spend considerable time with, no multiple dates, etc.).
Any way, this other girl I'd been intimate with had known from the very first time we slept together that I have a girlfriend whom I love with all my heart and am going to be with in the end. Of course, I was being a bit consciously ignorant of how a girl's heart works, and she quickly grew attached. I spent too much time with her, partying probably three or four times a month and then heading back to her place. I should have cut it off when she sideways mentioned, "I like you." The last time we had sex she laid there quiet afterwards, in thought kind of. I asked what she was thinking about and she said "sex with you." I didn't get what she meant in that moment, but shortly thereafter she left for the bathroom and spent a good deal of time in there. When she came back, I had a feeling she'd been crying. That was a turnoff simply because I started to feel bad, realizing I was toying with this girl's heart. After that, we went out a few times, but she continually denied letting me sleep over. When I questioned what was up, she said, "What am I going to get out of it?" I ceased contact completely, and a few weeks later, she unfriended me on Facebook.
My GF only ever cried when on her period and having a college exam in the following days. Nothing about any of that turned me on, that's for sure. lol