Although none of my family members besides my wife knows the extent of my cross-dressing I have actually been caught twice by relatives.
The first time was when I was 14. I had 2 sisters that were older and the oldest one liked to dress fairly trendy at the time. I had been regularly trying on her blouses and miniskirts for some time and I fit very well in my mom’s high heels. Any chance I got, I would put on various dresses and outfits. Usually, this would be when everyone was out of the house for ball games or when I stayed home from school pretending to be sick. I always got away with it, seeming to have a sixth sense as to when everyone would be coming home, and frequently got everything put away seconds before family members arrived home. I was starting to get more and more bold.
One evening I was home with only the one older sister. I was doing my homework at the kitchen table and she was in the basement doing hers. I figured she’d be down there for about a half hour at least and my super-powers would notify me if she was coming up stairs. I silently went upstairs, into her room and pulled out the black silk panties and bra. I knew right where she kept them. And I put them on. I put on some tan panty hose, a black and white blouse, and a black miniskirt that were my favorite outfit. I then went into my mom’s room and got her black high heels and put them on as well and went back into my sister’s room to look in her full length mirror. Just then I heard her open the basement door and start walking up the stairs. I was trapped! I prayed she would go into the bathroom and hid behind her door. When she entered her room and closed the door I gave a cheesy smile in a “ta-dah!” sort of way. I’m sure my face was beet red! She asked what I was doing and as I quickly undressed I said just goofing around. I was so flustered and embarrassed I took off all the clothes right in front of her getting completely naked so that I could contritely put everything back the way I found them.
I rushed back down to the kitchen table and tried to resume my homework but she sat next to me and wanted to talk. She asked if I was gay. She was very liberal and said it in a way that I knew she was saying that it was all right if I was. I said no. She asked if I had done it before and I lied and said I had not and that it was a spur of the moment idea. I made her promise not to tell anyone. She reluctantly agreed, again in a way that she seemed to imply that it wasn’t something to be ashamed of. But I was. The next few days I was walking on egg shells expecting the truth to come out but no one ever mentioned it. To this day she and I have never spoken about it again. I respect her very much for how she reacted and how she kept her promise.
If you have a fun story that didnt have a tragic result send it to me and I'll post the best ones. firstname.lastname@example.org
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