My Most Embarrassing 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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The Last Crossdressing Poll

Wow! Almost 3000 lovely ladies answered the last crossdressing poll. Under-dressing was the overwhelming favorite for expressing your feminine side while dressed ‘en homme’. From panties to stockings, a cami or bra hidden underneath an otherwise normal exterior you ladies enjoy your well concealed feminine graces.

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About the Author

A woman living in Seattle, enjoying the freedom to be who she is every moment of her life!

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  1. Terri says:

    Hello,

    I am still shy about going out in public do to the fact I want someone to go with me so that I can feel very comfortable.

    Thank you

    Terri Virgil

  2. Darleen says:

    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 dresses up like a girl.” she told my mom. I was in tears, but my mom just smiled and said. “Yes and he makes a very cute girl too.” As she walked out she said “Play nice.” My sister was mad that I didn’t get in trouble and told me to get out of her things. Over the next few years until she graduated and moved out, she would occasionally make me dress up and do my makeup, and then tease me. I continued to dress in the things she left behind and moms things. I was never confronted by mom and she never mentioned my being “caught”, but now my sis is very supporting of me and allows me to come to her apartment and dress. She has taught me a lot about being feminine and has even taken me out in public with her roommate girlfriend, (she’s gay). We have gone out to bars a number of times and they tease me about hooking me up with a guy, or trying to get me to flirt. The rush is so exciting, but I really would prefer a woman like my sister as a lover/husband, rather than a man…………..

  3. Carol says:

    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.

    • Vanessa Law says:

      Wow! Bravo to the manager on this one. That’s definitely a first that I’ve heard – a manager throwing someone out for discriminating against someone else. Perhaps there’s hope for society yet :)

  4. Leslee says:

    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.

  5. Terri says:

    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 Princlipales office where I was punished for trying to use the boy’s bath room. I would like to point out that this was in the 1960’s and there was standared to follow.

    I tried real hard to explan that I was a boy, but noone would even listen to me. i was told that I should never of lied saying that I was a boy when everyone could see that I was a girl.

    I was even told that I must start wearing dresses and skirts, and not to wear any more pants. I told everyone there that I had no dresses and skirt. So the next day my teacher brought me some dressess and skirts to wear, and she made me change into a dress that very same day, and to take the rest home.

    From the moment on I used the girls bath room to pee, and got away with it. Here is one thing even my classmates thought that I was a girl.

    Here is one thing not even my parents knew that I was told about that and they did not know that I was even being passed as a girl in grade school.
    Here is one thing I never took the dresses or skirts home.
    The same year we where having a school play, and guess what, I was given a girls part in the play. It was the main or lead role I had to sing and kiss a boy.

    Here is what my parents thaught about me play the role of a girl. They said that it was nice to see me play the lead in the school play. They did not say any thing. I found out late on in life that they thaught that it was normal for a boy to play the oppisete riole in a play and it was good that I had to learn how to be a girl, and it would not hurt me.

    To this day none even knows that I like to cross-dress.

    Love.

    Terri

  6. sashasxycd says:

    i was dressed pretty slutty in a short skirt high-heels and a tank top my first time out aand i went to a xxx shop to hit the video booths i was there for like 35 mins and when i was walking to my vehicle to leave someone that worked there came out and said Hey! i wanna talk to you n i was like what? he said come here i wanna talk to you then i walked to himn and he said We dont mind you coming here just dress a lil more appropiately. I was like sorry and hurry to take off. I havent been back since but i want to reallly bad

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