Did you ever get caught crossdressed on purpose ?

There are a lot of crossdressing questions in here I would like to ask did you ever get caught dressed in purpose by your mum , aunt ,sister or wife , for me the urge to get caught was quite powerful and when I did by my mum in her pink dress , tan tights and pink fluffy open toed mules the excitement was Immense and don’t forget this was 1980 times were very different I got spanked and then made to stay in her clothes for the rest of the day when my aunty and cousin came over to witness me

I’d love to know if anyone else did this and what the outcome was be great to hear from you

Thank you

What did your Aunty and cousin say when they saw you in a pink dress? Did you have to tell them you’d been spanked?

Great thread....

As a young teen I would spend days staying at my best mates house in the summer.

His Mum was so hot, I had a huge crush on her. Rightly or arguably wrongly, when the chance was presented to me, I would sneak into her bedroom and peek at her lingerie drawer. One a few occasions when it was safe to do so, I would slip on some of her knickers, just the thrill of it, the feeling of the material was exciting. I secretly wished I would get caught by her and punished, spanked perhaps or made to dress fully in some of her clothing and parade in front of her. Long ago now, but if I had my time again, I think I would definitely engineer me getting caught by her just to see how it played out

I didn't get caught directly or on purpose. In my early teens I had been giving myself enemas from my mothers enema kit. Part of my routine was to strip nude and put on my mother's bikini panties, bra, and lipstick before preparing my enema. Once I was in her panties, I would walk over to the bath room vanity and find the glycerin suppositories. I would put one well into my rectum and then put a sanitary napkin in the panties. My penis was rock hard as I prepared the enema. I pulled my panties to the side and slid the long tip into my rectum. I hung the bag high on a door hinge and took my enema standing up. By the time the 2 quarts had emptied into my tummy, I was cramping badly. There I was wearing lipstick, a bra and flowered panties with a swollen belly and penis. As I took the nozzle out of my full rectum I began to leak into the pad. I panicked and quickly got into the shower. But it was too late! I had made a mess in my mother's panties. But I was so turned on that I beat off while expelling into the napkin and flowered panties. I quickly cleaned everything up including myself and the lipstick. I put the enema kit back in the vanity. I put the bra back in the dresser but left the panties in the shower to dry. I fell asleep and forgot about the panties. My mother went to use the shower and discovered her panties hanging from the shower handle. She called me into the bathroom and I was mortified that I had been caught! She told me that if I didn't want her to tell dad that I would have to submit to a wooden spoon spanking. To which I did. She beat my ass red with that wooden spoon. But to this day I am still turned on by panty enema and a self spanking!

I kinda got caught on purpose once, I had a small hunch my friend liked me/ my body. So I dressed in a tiny skirt for a study session. It worked perfectly and I got rammed in the first hour 💕