The anticipation is always fare worse or far better than the reality of the event.
The biggest barriers that I have seen are the ones we put up in our own mind.
Case in point, preparing to go to a Reinsurance Festival I suggested to my friends (Jess and others) giving our outfits a dry run at Medieval Times (a medieval style dinner theater) the idea didn't catch on. However when we were at the festival one of the girl's told me that they didn't want to do the dinner theater because there were a lot of family's and thought the parents may have an issue ? Shes telling me this in the middle of the Reinsurance Festival witch is full of family's.
The biggest barriers are in our own minds.
There are places I will not go (note: most of these places are ones I wouldn't feel comfortably going to in boy mode either). One place I would go in boy mode and not in girl is a LOW end topless club, I don't go to these clubs but recently some lesbian friends took me to one (boy mode) lot of red-neck's, lot of hillbilly's, possibly some Hitler youth, think I saw 1 other black guy. We had a good time but glad I was not enfemme witch was the original plan.
Is this a barrier in my mind or is it a real unnecessary risk. I think my rule of thumb is "if its something I have to think twice abut as a boy I'm sure not going as a girl".
Footnote to this I do plan to go to a HIGH end topless club soon, with friends or on my own I have no qualms about it, lots of security and upper end clientele, that's if they let me in the door (no unescorted ladies). I think a lap dance enfemme would bee fun. (receiving not giving)
