they often do... but there's a problem. people who don't transition by like 25 are seriously unlikely to pass. fucking a dude basically forsakes women. your options with women will be reduced to like the most progressive 5% of them if you've ever fucked a dude. men don't want to forsake women until they're pretty certain they'll never have a loving wife, family, etc.. so probably not until they're like 45+. they're not going to transition at that point, and they're not going to be banging trannies either unless they're paying them, which is not going to fill the void of an actual relationship.
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