first match is settled by Mid-Boss. fact is that man was an overlord among overlords and had women. laharl's even from his relationship with a human woman - who knows how many women he banged that were actually demons. he had everything: money, power, and the man calls himself The Dark Adonis.
it's a no brainer there. that man got laid regularly, by angels, demons, and humans.
...second match kinda goes to Siegfried/Nightmare by virtue of me thinking neither Ramza nor Delita ever got laid. maybe Ramza banged his sister. if you assume that they somehow survived and that wasn't ghosts it'd work. otherwise... yeah, pretty sure no sex, ever. Siegfried had to have banged somebody before going crazy though and just has better odds to having gotten some action.
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The King Wang.
Listen up Urinal Cake. I already have something that tells me if I'm too drunk when I pee on it: My friends. - Colbert.