Not his first time in a Dress, heels, and women's underwear ? This is meant to be FUNNY !
I know many of us have turned down opportunties to be dressed as woman for costume events for fear of giving ourseleves away !
So it we were pretty clueless or wanted to drop hints, what might we Do or say or ask for that would get the womwan involved thinking you know a bit more about women's clothing than you should ?
So for example If you said
"I really think the dress would look better if I could also wear a full slip underneath !
And also even if you didn't request the slip and had to wear one, how do you put it on ? Is stepping into a slip and dress a give away ? Would most guys do that or pull it on over thier heads ? And then would take the time to kind of flatten the slip as they admire themselves in the mirror ! LOL
Some thoughts please ?