I too, as a kid, my brother and I being raised by our mother, stepped into her shoes...and dress...and make-up...and had such a laugh at her face when she came home from work. Apparently I hadn't done a bad job with the make-up. And going to a fancy dress party with my girlfriend at the time as a 24 year old, we swapped clothes for the evening and I bought size 12 high heels, and with my usual pony-tail fluffed out and half way down my back, was mistaken several times at the party and at a night club afterwards as a woman. My girlfriend and I were very relieved that she was not mistaken for a man. Being 6' tall and athletically slender, I was ribbed for the next few years about my imposing figure gyrating on the dance floor.
But a 'masked topic' needs not necessarily be straight forward, as that just makes for simple solutions and straight thinking. Sometimes best to lead someone into what they perceive as a nightmare, only to show that when the lights are lit, it has been a playground the whole time and only their imagination got the better of them.