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Historically, have there been any famous couples who meet these criteria:

The Korean tranny Harisu got married to a korean rapper that's four years younger than him/her.
What dignity of that rapper is left for him to rap about?
 
I really doubt it. AFAIK, transgendered men (or former men, if you like) usually identify strongly as either gay or straight. And anyone in a relationship with a female-to-male person needs to be awfully open-minded -- their surgeries are almost never convincing and the end result isn't equal in function. (As opposed to male-to-female genitalia surgeries, which are much easier and in many cases produce something cosmetically indistinguishable from the real McCoy.) Plus, if there ever has been a couple like this, I doubt they'd advertise their, uh, "conditions."
 
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