Most Helpful Girl
Whatever floats your boat. TBH, sounds like a pretty cool kink. I'd say, wear what makes you feel most like who you want to be/what makes you feel the most comfortable (because women's underwear has no space for male genitalia and side ball spillage might be painful after a while).
Most Helpful Guy
Ummm... okay this took me by surprise
Do whatever makes you comfortable I guess lol