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.

Unleash Your Inner Woman

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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36 Comments
  1. Cdjenna622 2 years ago

    my most embarrassing moment was when I got a makeover done and was wearing a silver dress. I had a sandy blonde wig on and had my eyebrows waxed. I even had on a pair of eyelashes on. I drove to Ventura looking pretty. I had a suitcase with all my girls clothes next to me. as I got in to town I was pulled over by the police right in the middle of the busiest Street. I was so nervous about getting caught. when the officer walked up to my window and saw me he ask me to step out of the car and stand in front of his cop car with the spotlight shining on me. he searched my car and did not find anything it took him about 20 minutes making sure I had no warrants and then he searched my car again. it was about 6 p.m. and there was so many cars driving by. about 15 people walked by me whistling at me and some of them called me a sissy boy. one girl called me a cross dressing slut. I just smiled at them. it was so windy I had 2 hold my dress down. I let go for a second and it gust of wind lifted up my dress showing everyone who’s staring at me my thong panties. I grabbed my dress pulled it down holding on. the officer ask me to walk to his driver’s door to give me back my license. he told me I was free to go so I walked back to my car and a gust of wind blew my dress up again showing off my thong panties and showing him my bulge.

  2. As a male equipped CD’r, when it comes to pee….I would prefer to stand but when en femme, must sit. It amazes me how long it takes to prepare ones self to perform the act. I have to hands it to the genetic females…..they have the skill and art down to a fine point. It is horrible to try to remove, pantyhose, panties, leggings, girdles, corsets just to be able to perform the function. Such panic when one must go really bad

    Just an observation….on being a girl!.

    • Janine 1 year ago

      I went through the same things that you did until I found a answer to the problem.
      It’s a prosthetic vagina that allows me to sit down and pee without removing anything except for taking my panties down
      The prosthetic vagina has a sheath inside of it that holds my penis and I can urinate sitting down
      It also directs the flow of urine into the middle of the toilet bowl so that it sounds like a girl dose when she’s peeing
      Very convenient when I use a ladies room so my feet are pointing in the right direction

  3. Keri Q 2 years ago

    I have had a couple of situations that were embarrassing. One was clearly my own doing and the other was accidental.

    The one I should have not placed myself in was very awkward. I was in my local work out place and it was late. I always wear panties and often wear other women’s things like running shorts, tops etc. I thought I was the last person in the locker room and decided to prance in front of the mirror in just a pair of pink lacey panties. In walks a guy and takes one look at me and calls me a faggot. I dart to my locker and quickly dress. As I get into the parking lot he is leaving and puts his window down and calls me a faggot again. I was totally embarrassed. By the time I got home I was totally excited. In those days I hadn’t quite accepted that I was a fag but times do change.

    The second time I was home and this was unexpected. We had a housekeeper and she had the key. It was a holiday week and she came a day early. There I was in the kitchen in a full nightie and panties on. She went oops, sorry and I rushed to the bedroom. She never said anything after that. She was quite aware that I wore women’s things as she did the laundry and always folded my panties, bras etc separately from my male things. I had no male undies so it was more than obvious.

    We all grow as crossdressers and although I am still closeted to a great extent I have less inhibition about it.

  4. kimberly 2 years ago

    i think the scariest and most embarasing moment happened when i was 11 or 12.
    i dont remember where i got it from but i had a black bikinni. the house we lived in had a porch with a like wall on the edge and a roof. so you could lay on a lounge chair and not be seen unless you started to come up the stairs to the porch. even though it was covered the sun stillhit the porch most of the day so tanning was easy. so i was laying on the lounge chair in the sun wearing the bikinni. after a while i needed to use bathroom so i went inside and did what i had to do. i was inside for a little while doing who knows what when someeone knocked on the door. i dont know why i went to answer it but i did and boom, and there i was standing in a black bikinni facing my grandparents. i think my mind did a quick “oh shit” and i ran to my room and threw on some shorts and a shirt. my grandparents never said anything to me and it was never mentioned by my mom so i dont know if they told her or not but i was scared

  5. Keniffer 2 years ago

    I like sort of setting myself up to be seen and embarrassed a bit when I’m in some other town. I stopped at this store one time, as soon as I walked in I got the attention of this cute teen girl that worked there. I was in guys clothes still. I watched this girl and she was bouncing back and forth from the second till to the ladies wear. I made my way there a was holding a bra when she came over. She watched me from a distance and I could just barely see her out of the corner of my eye. I kept looking through the bras. Then she disappeared into the back room. I could see the one way glass and thought she might be watching. I looked around. No one was watching me and I slipped the bra over my arms and held it against my chest. She came flying out the door and looked right at me with a weird look. I looked down and took off the bra while she watched. I moved to the panties next. When I saw her next she was coming up behind a rack of clothes. We could only see each other from the waist down. I held the panties right up to myself to see how they looked. I heard her say omg and then went up to the other girl at the till and imitated me holding the panties. The two of them laughed out loud for a long time. Suddenly I realized I was the only person there and the store was closing. I went to the till with one pair of panties. They both where laughing uncontrollably. I went to the till that this girl was working at. She said we have a return policy, just that. She got a bag out then put it back and said you can just carry your panties without a bag. As I was almost out the door I heard screams of laughter.

  6. Janine 1 year ago

    One of my most embarrassing times was when I was in a store and found a skirt that I just couldn’t live without.
    Taking it to the fitting rooms the girl there directed me to a unoccupied fitting room.
    I was excited about trying the skirt on and went into the room and closed the door behind me.
    I sat down on the bench seat and was removing my skirt and it was down by my feet.
    I was sitting there without any panties on and all of a sudden the door to the room opened and there stood a girl looking at me sitting there.
    Thankfully I was wearing my prosthetic vagina and she hurriedly closed the door saying excuse me.
    I was so embarrassed that I hadn’t locked the door in my haste to try on the skirt that I just couldn’t live without and had exposed myself to a complete stranger
    I finished trying on the skirt and it fit perfectly.
    I put my skirt on and took the skirt with me to the checkout and paid for it
    Thankfully I didn’t see the girl who had opened the door and saw that I was sitting there without any panties on.

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