Have you ever been caught cross dressing if yes who caught you and what happened?

Answer 1

Got caught by my sis when I was 16. She was cool about it (after a lot of tears and begging lol) She let me dress up a few times after that, and one halloween even took me to a party

Answer 2

First thing.... Yes, I've been dressing for over 30 years, and in that time, it's happened a few times even though I am always very carefull about choosing the time and place for dressing. I have been caught by my mother, sister and two care staff (Boarding school). On each occasion I was treated like a joke, laughed at, in an attempt to humiliate and shame me into not doing it again, needless to say, this failed.

Second point, in retrospect.... I realise now, that during my teenage years I activley wanted to get caught by my sister for exactly the reason above, in the hope she would try to shame me, because I found it pretty damn thrilling at the time.

Answer 3

I have not, but one of my tgirl friends has just been caught at work. She is finding some of the men are now flirting with her and now the laughing is over is thinking about going to work dressed as a woman. Single never had a girl friend, small company, i think the office had guessed before. As a man very femme. I like that in a man.

Answer 4

I've been caught twice cross dressed, both by family members when I was younger.
The first time my older sister caught me dressed in her private school girl uniform. She laughed at me a bit and told my parents. But nothing bad happened. She told me she always wanted a sister, later she took me into her room and totally dressed me as a girl with make up and all. It was great bonding with my older sister that way.
The second time my mother caught me wearing my sister's nightgown while I was sleeping. Again, nothing bad happened. My mother just told me to quit wearing women's clothing because if other people find out, they won't be as understanding.
Now that I live on my own now, I dress up anytime I like when I'm home.

Answer 5

Yes. I was caught by my college roommate, when I thought he had left for the weekend.

I was wearing a wig and had water balloons for breasts. Dressed in lingerie, a sklrt and heels.

He was like what the heck ?!? But then ended up telling me to dress like this more often or he'd tell. We never did anything, but I'd have to dress for him during the weekends and late at night.

Answer 6

No, never caught though but here are my thoughts, When younger I think a younge man wants to get caught by his sister or mother with the hopes that they will accept it and help him further with his feminine side. As they get older, maybe in college dorm, he would like to get caught by his male roomate - again hoping to be excepted and even hope he gets to live out his bi-feelings or fantasys. Then when gets older he no longer wants to be caught, but is usually honest with his girlfriend or wife and hope again that they too will help him with his feminine side of his life. Women's cloths are much more soft, smooth and sexy than a man could ever experience with typical mens cloths

Answer 7

I hav'nt been caught outright and now my g/f and i do it quite alot. I think most guys have tried crossdressing but very few will tell you they've been caught red handed. Sorry i'm off the track a bit but was intrested in the question.

Answer 8

I've never been caught cross-dressing, but I have had a few close calls.

Answer 9

yes when i was 15. i went outside into the garden to put rubbish in the bin and my mate's sister saw me from her home across the road. i didnt know until the Monday back in school. i got ribbed there after.

i go out now in womens clothes -jeans, tops and trainers and no one notices. i am transitioning step by step mind. butend of the day, who cares. people have got there own insecurities any way to be concerened about what someone else is wearing anyways.

Answer 10

yes i have
One night my Gf and i whent out all dressed mustach and cocks the hole bit. on the way I really needed to take a leek and i obviosly couldint go to the womans wash room so i creeped into the mens were i bumped into my Boss and lost my mustach.

I quit the next day. lol