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Hm...the two feminization scenarios that come most immediately to mind are some sort of machine intended for girls going off on a guy or some sort of punishment...
Yep. Sometimes it's possible to have two people in one role, although even then there tends to be a top/bottom element between even two bottoms, and those are hard to set up.
As I said, I don't really have a major preference. Bottoming is nice, but I've also learned to like doing the top role too, so if your preferred role is the lower, I can do the top.