I know many of you are deep in the closet and I remember completely the pain and paranoia it creates. The problems of near misses and discoveries are legendary.
Of course I have my own, and many of you have commented here in Cyrsti's Condo about yours, but here is one classic. From an acquaintance of mine years ago, who just happened to open the door to the wrong person when he was cross dressed.
I am going to switch pronouns now and say she was able to cross dress extremely well into an attractive classy woman. She also was single and her house was pretty much a central "meet-up" point for a group of individuals I knew who spanned the full spectrum from an admirer or two to transsexual women.
As she told the story, a couple of friends from our group were due at her house at a certain time. As the time came, the doorbell rang and when she opened the door it wasn't the expected friends at all. The person outside was one of her male co-workers! When he saw her, he got this little grin on his face and asked for his male friends name. Even though her mind was exploding at the moment, our cross dressing friend said she managed not to lose her cool and said they were going out later and he had just ran up to the store.
Fortunately, this was in the mid 80's back in a time when his career could have been totally ruined by being outed at all-but he wasn't. Instead, in the very intensive male job he worked at everyone wanted to know who the new hottie he was dating was.
Even though he had the benefit of appearance when he cross dressed, he said he was always careful to see who was at the door before he opened it. No matter when it was.
I'm going to try to come up with a "best of" list of my screw ups in a later Cyrsti's Condo post!