My favorite case is that of James Barry, who was born Margaret Ann Bulkley and successfully impersonated a man throughout her adult life. Barry qualified as a doctor and served as a surgeon in the British Army. It was not discovered that Barry was a female until he died in 1865. Thus, Barry was the first female born in Britain (c. 1792) to qualify as a medical doctor (1812).
So, one could say Barry had a pair of tightly nestled tits.