Hi
So you just had Halloween and got a chance to go out en-femme (for those who need a reason )
I am from Israel, so the Jewish equivalent is called "Purim" where it is common to go in disguise (this year "Purim" is in March).

So I always wanted to go out in en-femme in "Purim" and never did it. I never had the courage to go to a party alone.
I always think it's better to go out with company.
Now, dressing up en-femme (as we do) would "out" me immediately to anyone who knows me. It would be obvious that I am not just wearing regular female costume (women's shoes in man's sizes is a dead giveaway). I never confided in men, and frankly prefer women's company, so I want to go out with a woman..

My wife doesn't really want to see or hang out with me en-femme. So I tried several times with friends (women, naturally), but I always got turned down, or things didn't work out.
I can only assume that it is embarrassing for woman to go out with a crossdresser, especially if we might encounter people she knows.

Any insight or tips anyone?