Different strokes for different folks
Fabian Nicieza (I think he was the one) refer to Cable and Deadpool as one of the greatest love story he has ever wrote, and Wade Wilson's entire body is scarred by tumours.
At first, I really shy away from the fanart, even though I thought the fic was hot, because Wade's personality is hot, but over time, I found the fanart hot because Wade's personality is hot. I wager the same thing it is with Tony, he loves her personality enough to love her face as well, it sound like they had a hack of a snarky time together.
...and Christ, I've always read Tony as a bit of a submissive, so a villaintress suits him...