Considering the popularity of both the nautical lifestyle and the disapproving-brother-Spain in the EngPort fandom, this popped into my head...
Remember the general idea that Portugal became acquantied and allied with Portugal (en route to a Holy War) whilst Portugal was fighting for independance from Spain (and the Old Islamic Empire)? I'm thinking that Jack Sparrow might not have been alone in his mistaken brothel-vist.... What if a certain English pirate-Captain had accompanied him and found himself a lovely little prize in the form of rebellious Fem!Portugal shut away in that Spanish convent by her possessive brother Spain...? Well, as a gentleman, he could hardly leave the distressed damsel (read: wildcat) in there...
I realize that
A) This is going to be severly challenging historical chronology, so it can be as humans rather than Nations,
B) I'd love a full-fledged fic of this, but that could potentially be an intimidating epic to write, so a one-shot is welcome!
Um... Someone fill, pretty please? ^_^