My most embarassing crossdressing moment

Have you ever had a moment when you wished your high heels would part the sidewalk beneath your feet just long enough to envelop you? A moment when time seemed to draw out like the never ending strands of your favorite silk blouse, and all you could hear was a wave of laughter slowly washing over you? It’s perhaps at times like this you wished, hoped, dared to believe that crossdressing would forever remain in your past.

I’ve been quite fortunate in my crossdressing career (my transgendered life?) to have had few moments of outright crossdressing embarrassment. Most people I meet in public are either friendlier than usual, or don’t notice me as they walk by in their own world. A few people share a look of dawning surprise on their face – one which is usually soothed by my friendly smile. At least I think it’s my smile – perhaps they figure I’m a crazy woman and don’t want to attract too much of my attention 🙂

My Most Poignant Crossdressing Embarrassment

There is, however, one moment which sticks out in my mind and still makes me blush. Though I find I blush more so at my reaction than the situation itself. One evening many years ago I decided – quite boldly – to apply a coat of nail polish before venturing out as a guy. Having once attended boy scouts, I knew to always ‘Be Prepared’ and “wisely” wore a baggy jacket with plenty of hand-hiding room. Perfect for concealing my painted nails, should someone choose to notice them.

I spent a nervous fifteen minutes browsing Circuit City, where I’m sure I spent a good three minutes with my hands courageously not shoved deep into my pockets. After mustering all the nerve left within me I took my purchase to the cashier. Just as I was paying a man behind me exclaimed to his friend in a rich Southern accent, “Hey, there’s one of them crossdressers”.

I was busted, and couldn’t very well finish paying with my hands in my pockets. I smiled nervously at the cashier, and felt my vision narrow as I tried fervently to hide in plain sight from the two men next in line. Time seemed to stand in awkward stillness as I rushed to finish paying and get out of the store. The cashier seemed to be embarrassed as well, as if somehow my crossdressing embarrassment were contagious.

Eventually I made it out the store and into my car. Apart from a few moments of furious blushing, nothing bad happened at all. I sometimes wish I could go back in time to that moment and do it differently. I imagine myself turning to the gentlemen, and with a warm smile extending my hand and saying, “Pleased to meet you.”

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Darleen
Darleen
13 years ago

I was caught in my older sisters clothes, panties, bra, slip, dress, and heels. She called me names, teased me about being a sissy, and told me she was going to tell our mother. I begged her and she didn’t tell, but several weeks later, she took me into her room and made me dress up again. She put eyeliner and lipstick on me and combed my hair in a feminine style. Then she told me to wait a minute and left. I was admiring myself in the mirror when she walked through the door with our mom. “See, Daryn… Read more »

Carol
Carol
13 years ago

Years ago, I was in my favourite restraunt, sitting at the bar, having a steak dinner. I heard a commotion behind me, but didnt look round, as that might call attention to me. Well anyway, about a half hour later the manager came over and apologised about the commotion. I said no problem, but what was going on? It seemed some macho dude said some wise crack to his girlfriend about me, and the manager caught the remark. He got into a commotion, and threw them out. I felt proud they would support me.

Leslee
Leslee
13 years ago

When I was about 10 years old I ordered some very sexy panties from mail order. Normally when they arrived I was home in the summer from school and got to the mail first, but this time my mother got there first. There were three very sexy panties in a black box. She embarressed me but than gave them to me anyway. I think she already knew as one time she refered to me as her special child.

Terri
Terri
13 years ago

Hello, My most embarrassing moment was a few times for me, but the one that does stick out in my mind now would be the time I was catch going into the boys bath room when I was a boy. I was ten years old and had to pee. Just when I was about to go into the boy’s bath room to pee my teacher stopped me and told me that girls cannot go to the bath room in the boy’s bath room. My teacher marched me into the girls bath room to pee, then she marched me to the… Read more »

Gail
Lady
Member
7 years ago
Reply to  Terri

Nice try—No not really, not even a possible fiction story!

I grew up during the 50’s/60’s and even with standards of the time, (I went to Parochial Schools, taught by Nun’s) parents were Always notified and there was no way a teacher would ever confuse the gender of a student, even if that student were in another classroom!

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Mona.
8 years ago

Few of the embarrassing moments I came across are quite similar to ones told above.. Once I was traveling to Germany where I have had gone out en-femme and felt quite safe. We were group of friends traveling together that time and none had any idea about my cding. Since I had plans to dress up, I had my toes painted in bright red and I was wearing stockings and panties under my clothes. Later we all decided to go for some waterspouts and swimming. I did not realize my mistake until I almost removed my pants only to find… Read more »

evette
evette
7 years ago

hi my story is a little different than most, i dont dress up all the way much but i enjoy wearing a skirt when i go out sometimes some people looknbut most of the time people dont even care what you have on, but i dont care one way or the other, im a older man so it dont matter what they say.

helene
helene
7 years ago

The most embarring with , after shopping all day at several stores, trying all dressing rooms and rest rooms. I went to a second hand store and found a gorouse mini dess , that I had to try on, As I entered the dressing room I heard the fatefull words from a young girl I did not even try the dress on, I only wait until I calmed down, Left the dressing room, checked out and left the store. PS the dress fit perfectly!

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Janine
6 years ago

My most embarrassing moment was when I was in a mall dressed en.femme and needed to use the ladies room. I walked over to where the entrance was that led to the ladies room and there was a young mother standing there with her three young children. She was looking at me as I came towards her and when I got close enough she said You’re not a woman.You can’t use the ladies room I stopped in my tracks and said I’m as much of a woman as you are so excuse me but I have to use the toilet… Read more »

Helena
Lady
Member
6 years ago

My most embarrassing moment was when my roommate walked into my bedroom and discovered Helena for the first time. I was alone in our apartment, as I assumed Greg was going to be at work for most of the day because of a huge project he and his team had been working on. I just decided to dress up, and go about the apartment in all my glory. It had been a long time since I had been able to do that, and I was taking full advantage of the opportunity. I didn’t expect Greg to be back until well… Read more »

Jennifer
Jennifer
6 years ago

hey venessa i once was in a lowes home improvement store and noticed a man and woman standing there they both wore sandles and both had their toe nails painted bright red i had wished it was me

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