Have been caught multiple times, and I felt sick to my stomach and very embarrassed most times. Here are a few times. Not in order, and many are years apart.
Caught by my friend's sister trying on her pantyhose in their bathroom with the door closed and locked, but she opened it up the door quickly lke it was unlocked.
Caught by my older sister in her bra(stuffed), panties, dress, pantyhose, and high heels, practicing walking in her high heels when no one was supposed to be home.
Caught by my mom when she came into my room unexpectedly and wanted me to strip off what I was wearing and try some pants and shirts on immediately. I hoped that she didn't notice that I had on my sister's jeans and shirt that looked similar to some I had, but also was wearing her bra and panties. I protested doing it right then and in front of her and even told her I had to use the restroom first, but she insisted trying those clothes on right that moment. so I pulled down my jeans in front of her revealing not only my sister's stretchy pink nylon panties I was wearing that day, but also revealing to her that my legs were smooth and hairless, because I had shaved them as well as my armpits and also wearing my sister's bra. She told me to get my sister's clothes off and try on those clothes and left me standing in my sister's bra and panties.
Caught by my aunt wearing my sister's bra(stuffed) and panties and a girl's nightgown. Was staying the night with her and had worn my normal pajamas thay she saw, but had later changed into that for bed after sneaking into her makeup and putting on some lipstick, blush, and mascara. Got up to use bathroom and thought she was still asleep, still dressed in the nightgown and walked right in on her as she began washing her hands. I was going to run back to take off the nightgown and put on my pajamas over the bra and panties when a wet hand grabbed my wrist. She told me the bathroom was free and led me to it. I had to go badly and was going to lift the lid, but told me that I could set down to pee like a good girl. I washed and was going to change when I was finished, she said don't change out of my mightgown, but I should remove my makeup before breakfast. When I went to to wipe off the makeup, it wasn't wiping off like my sister's makeup did. I walked into her kitchen still in the nightgown and still wearing her makeup, which I found out was waterproof. After breakfast, she helped me remove the makeup.
Was wearing my underwear over my sister's panties to hide them. Her panties were very comfortable and after wearing them for a long time, they would feel like I wasn't wearing anything, so I forgot I had her panties on after a while. My other sister said something mean to me, so being immature I would often give her the full moon (show her my bare butt) when she did and would sometimes also slap and say kiss my a**. Instead of showing her the full moon as I quickly yanked down my shorts and underwear and tell her to kiss my a**, I revealed to her that I was wearing our sister's panties, which I when I slapped and felt panties instead of bare butt. She roared with laughter at my expense. She wanted me to play dress up alot after that.
Home alone and was wearing my sister's swimsuit. We had a wooden privacy fence and it was cloudy, so played in that for a long time. Didn't realize till dividing up to play where one team of boys got to keep shirts on and other boys had to remove shirts that I had girl's tan lines that could have only been from a girl's swimsuit. There was a comment and I lied and said it was from my top, not a girl's top.
Thought everyone was gone, but was caught by a female teacher when I was trying on one of the girl's band uniforms which was a skirt and sweater. Tried to play it off as a gag, but don't think I nor my shaved legs fooled her.
Had an afterschool job that required uniform pants, even very hot weather, but girl's were allowed pants or skirts. I asked if I could wear shorts during a very hot period of weather, but was told no shorts, only pants or skirts. I already was wearing panties and the skirt was appealing to me with the heat, so I joked with my boss that I might wear a skirt or maybe skort then, but she said no, because skorts weren't allowed and no on the skirt because it would be too distracting to see a boy wearing a skirt. She was a "skirts are only for girls" type of person. We wore a smock-like garment over our tops, so I sometimes a girl's top that looked unisex and girl's pants I had picked up used which looked like boy's pants, but they didn't have back pockets and fit tighter like girl's pants, which I liked because I could pull up the top and see a pantyline on my reflection. I even went so far as sewing in a tag from ine of my other pairs of pants, so I could say I thought they were boy's pants if asked or anyone saw them and questioned the tag would be in a boy's size. The day it happened, I was wearing girl's pants and panties, which luckily were yellow panties that were faded enough, because I went to do something and the seat of my used pants ripped open showing the panties to everyone behind me No one said anything, so hopefully everyone thought I was just wearing stained white boy's underwear and not girl's faded yellow panties.
Caught by my sister with some breastforms I had acquired and attached wearing her prom dress with a wig makeup and heels.
Caught by my sister wearing blouse, skirt, heels dancing around twirling the skirt.
Caught by my sister wearing her cheerleading uniform with makeup and wig shaking the pompoms and trying to mimic the cheers.
Caught by my sister dressed in her clothes in the middle of using one of her tampons on myself.
Caught by my sister in the middle of using something on myself that vibrated that I had found along with some lube in her drawer.
Caught by my mom wearing my sister's school uniform along with one of my guy friends that liked me wearing my sister's school uniform (in the middle of an adult situation).
Caught outside locked out of the house wearing bra(stuffed), panties, wig, makeup, dress, and heels and having to wai for them to get home to unlock.
Caught by my sister when I was wearing bra (stuffed), panties, pantyhose, heels, hair fixed like a girl's, and her dress, which I was able to zip up the back and fasten, but couldn't get the zipper back down. She unlocked my door and even though I tried to hold it closed, I couldn't get traction with the pantyhose on and she was able to push open the door. I had to get her help to unzip the dress.
Got pants pulled down by a couple girls when I was wearing my sister's panties.
Was given a wedgie while wearing panties.