Yeah, I can't really envision how the two (sex and crying) would fit together for the kind of thing I'm into either.  At the very least, the guy would have to be turned on by his own crying.  But I don't find requesting crying awkward at all if a guy is into it!  I lucked out with one who was willing to comply, but then, I didn't want to have sex with him anyway, just cuddle and stuff (but he knew about my fetish).  It was totally addictive AND mentally satisfying for me.  Which is what I need most.  My *mind* to be blown.  Hehehe.  Yeah, it's like my sex organs actually exist in my brain.  If you're able to get me off up there, your work is really done.  I'm just weird that way.