I have been caught many times, so I’ll give you a good story and a bad story.

I started crossdressing very young. At age 5 my parents would laugh and tell me “boys don’t wear that”. But soon it changed to fussing at me and then beating me for trying on girls things. When I was 14, my mom and brother went out of town, to my grandmothers I think. My dad said he had to go to work and that I was to stay in the house all day, and when he got home around 6 we would go get dinner. So as soon as he left I put on my moms things: bra, pantyhose, dress, shoes, makeup! Along about noon I was getting hungry so I went to the kitchen to make something for lunch, and then I heard the front door open. I looked around the corner and saw my dad coming in. Before I knew it he had pulled out his belt and was swinging it at me (holding the leather end so the buckle was hitting me). He chased me around the dining table and eventually I got up to the bedrooms and took the clothes off. I ended up with bruises on my back, arms, and sides of my head from that one.

OK, enough of that, here’s a good story:
A few years ago (I’m almost 60) I started feeling like I’m tired of sneaking out of the house. So now I get up one or two days every week, get dressed and go out to do my errands, shopping and lunch out. By the time I’m ready it is usually about 9am, and most of my neighbors have already left for work, and the children have gone to school. And when I’m done and return home, it is usually mid afternoon, like about 3pm, so the neighbor are still at work. But one day I returned home and sat down at my computer to see if I had any emails. As soon as I turned it on, a facebook message popped in from the lady across the street. She asked “Who did I just see driving your truck with lots of hair?” CAUGHT! Obviously she knew, so I told her it was me, and that I did this a few days a week. She had left something at home and had come back to pick it up. We traded a few messages, she seemed interested and even said she wished she had been able to see me better, so I sent her a couple photos of me dressed.