I am a life long crossdresser and have had some extreme situations happen because of it.
The first time I was ever caught while dressed happened in 1989, I was at home alone and as nobody knew about my dressing I wasn't as careful as I could have been and long story shortened my brother walked in on me wearing black lacy lingerie (bra, suspenders panties and stockings) and high heeled shoes as I was doing my makeup.
I was startled by his appearance but was even more alarmed by his smile, before I said anything he was already telling me what it was going to take to keep him quiet.
I spent the rest of the day pleasuring him and some of his friends by both sucking and allowing them to fuck me.
I only did this as I was already married and had 2 children and didn't want to lose them, I spent one day a month for the next 3 years in that situation until my brother moved abroad and I moved to a different town away from his friends.
Depending on comments made by those who read this I may go into more detail about the things I did as it actually feels quite good to finally get this off my chest
