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 πŸ™‚

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 triedΒ ferventlyΒ 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 wereΒ 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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I’m passionate about creating a safe space for everyone in the transgender community to find laughter and friendship on their journey. I completed my physical transition in 2011 and through it I lost everything, and gained everything. I am blessed that I was forced to gaze inward and embark on the journey to discover and live my authentic self. My deepest wish is that all who wander here may find peace, happiness and freedom.
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5 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… Read more Β»

Dame Veronica Graunwolf
Active Member

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!.

4 years 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

Keri Q
Keri Q
5 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… Read more Β»

4 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… Read more Β»

4 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… Read more Β»

4 years 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… Read more Β»

Michelle Davis
1 year ago

One morning when I arrived at the office and greeted my secretary she looked at me like I had three heads. It took me a moment to figure out what was wrong and then I realized what it was. I had tried on a pair of my wife’s clip on earrings that morning. They were very pretty and I liked them on me. Turns out that they were so comfortable that I forgot to take them off before leaving the house. I mumbled something to her about my wife must have been playing a joke on me but I’m pretty… Read more Β»

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