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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I was about 15, maybe 16, when Mom and Dad arrived home a “little early"… There was I, sunning myself in the (very private) backyard when I heard my Mom asking my Dad something. I was wearing a brown skirt and some heels that almost fit.
Yeah, it was an embarrassing moment.
Hehe, I’ll bet they had quite a surprise when they walked in on you 😉
I have a thick skin so any embarrassment rolls off me.I enjoy my time out and about and refuse to be fazed by anything.. Wish others would carry themselves this way and enjoy their girl time as I do.
My embarrassment occured at 21(I’m 35). I had decided to finally purchase my first femme outfit. I was still wearing my mother’s clothing(which I started @ 14). I was still living at home while going to a local community college. I didn’t have the courage to go to a store, so bought the clothes from a crossdressing store online. The clothes were shipped with no problem and were excuisite. I still remember the outfit. 2″ black platforms with 4″ stilleto heel, black fishnet hose(control top); a black, faux leather mini-skirt with a white w/various size black dots silk blouse. The… Read more »
Can’t say I’ve ever been embarrassed, but a few moments I have had. Once while at a job (I had come out to most of my friends by this time, but not to anyone on this job) I was sorting paperwork, standing over a table where a lot of people walking past behind me when I realized that my panties were showing around the top of my jeans. They were white with pink roses on them, so obviously female underwear. The next day I overheard some people talking and some laughing. It didn’t really bother me, I was not at… Read more »
My most embarasing moment was several years ago. I had been in the garageand had taken a fancy to one of my mothers bras. I decided to try it on. After taking off my t-shirt, I put it on. I couldn’t believe how good it felt. Next, to fill it out, I used newspaper, not the most comfortable thing to use, but it was what was available. Just about that time, here comes Mom and caught me red handed. Of course, the questions started, mostly why. I tried to explain why, but just couldn’t get a reasonable excuse out. After… Read more »
I remember a number of very embarrassing situations that occured many years ago, when I first started cross dressing. At the time, I was fairly insecure about the whole thing and was always very conscious of what other people might think. I specifically recall a time when I spent the whole morning dressing up as Paula and then headed out for some retail therapy. I’d only just entered the first shop when I saw a young guy point at me and tell his friend “That’s a Man!". I just wanted the ground to swallow me up. I was so embarrassed… Read more »
I used to purchase my clothing from Charity Shops but after one incident in a YWCA shop when the old girls behind the counter refused to sell me a dress saying " this is a nice dress far too good for a man to mess about with" (what magazines had they been reading?) I then started shopping at “Second Time Around " Dress Agencies, shops where the commercial acumen took over, they where keen to sell and cross sell with " have you got a nice slip to wear" and “a foundation corset would help you achieve a good figure"… Read more »
I also have a thicker skin. I was not embarrassed per se getting caught a couple times wearing female attire. It was an annoyance mostly because I wasn’t ready to come out.
My most embarrassing moment happened when I was 38 years old. I was home alone one day cleaning up the house. I was wearing a black micro mini skirt, panty hose, baby blue stockings above the knee, a baby blue top, and black high heel Mary Janes. Anyways I had a bag of trash and stepped out in the back yard and walked to the side of the house to toss the bag in the trash can, my backyard is pretty private. As I walked back to the house feeling very sexy I began to panic because I had the… Read more »
That’s such a great story, Franny, and reminds me of my own cat calling incident! I actually loved it when I got caught with my pants down and my round butt was exposed to some guy! Email me at CurvyAthelene@gmail.com if you wanna talk some more.
Gosh Franny, that’s quite a story! I’m glad you made it inside your house. At least you know that you pass well from one angle 🙂