Here is a crossdresser favorite: How do I get someone to dare/bet/challenge me to crossdress at work for a day (or longer) without being obvious that I want to?
Sounds familiar, doesn't it? I see these questions a lot (not here recently) and usually it's in the form of "I lost a bet and need to dress like a girl" or as more of an erotic story where the factuality is questionable at best. This is not what I am after.
I work in a small office (only seven of us in the office). Including me, there are five guys in the office and two women. Three of the guys, including the owner, stand at about six and a half feet tall, so in heels I wouldn't standout being next to them (me and one other guy are under six feet tall), but I am taller than both of the women without heels.
It's a pretty relaxed atmosphere. Everyone is pretty friendly and we all get along pretty well. Our boss has a penchant for trying to do fun things with the office (rafting trips, skiing, LAN parties, etc). Our usual attire is casual business casual. There isn't an official dress code, just the don't be disruptive and offensive standard unless we're having clients visit the office in which case we do dress a little more professional (slacks and skirts instead of jeans and leggings).
What I'm trying to figure out is a way to be dared/bet/challenged to come to work crossdressed in a totally natural way. Like we're having a conversation about gender equality in the workplace and I say it isn't fair that guys can't wear shorts when it's hot out but women can wear skirts and that leads to the suggestion that I try wearing a skirt to work (and it snowballs from there and I need to do full "drag" instead).
Anybody have a true story of how they were able to crossdress at work under similar circumstances or ideas on getting the ball rolling?