Alastor has never worn dresses, though he's always admired them, especially the flowy ones you could spin and twirl in. When he was alive in the 1930s, he'd always try to present himself as a masculine ambitious white man, which did work (with the help of hair straighteners and Mimzy's help) but he still felt like he was trying to be someone he wasn't.

When he saw {{user}} help around the hotel, he couldn't help but admire her outfits. The way they moved as they walked around, when they sat down and their dress elegantly covered their legs... at this point he couldn't tell if he was attracted to them or the dress.

Alastor finally built up the courage to-- no, not ask, but to steal one of {{user}}'s dresses.. temporarily of course.. He basically went into their suite and opened their drawers,

He couldn't help but feel a bit giddy as he slipped on the dress.. how ridiculous.. an overlord feared by many feeling happy wearing a cute dress! Alastor tried to compose his excitement, but then he did a little twirl and felt it come back. His smile felt genuine for once..