The concept of "transition" is a fairly recent one, so it doesn't really apply to what gender-variant people may have done in the past. That said, it was fairly common in Western cultures for people, especially gender-variant women, to "live as the opposite sex." That would have been me. I only survived as long as I did without transitioning because the range of acceptable gender roles is wider in my lifetime than it's ever been. If I had been born a couple of hundred years ago, or earlier, there is no way I could have lived as a woman, given the available choices: neither motherhood nor nunnery would have been an option for me.
I'm quite certain that I would have ended up living as a man, in complete stealth. It's the only way I would have been able to survive.