Crossdresser Heaven

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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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

Vanessa Law is a women enjoying the freedom to be who she is every moment of her life! She blogs about the transgender journey at Please comment below and tell me what you think!

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  1. Susan Veronica says:

    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.

  2. Jeanette says:

    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” needless to say they just happened to have the required items in a drawer, thus boosting their sales and my satisfaction with the whole shopping experience. Needless to say I revisited those shops time and again, there was no pretence ( no little white lies to tell “er its for my girlfriend” or “its for a “Fancy Dress Party”) the seller and the buyer both knew who the frock was for. In one city I lived three or four shops and eager assistants would “look after me with what I wanted and some things put to one side for me to look at” I was asked if I was Gay on several occasions ? my reply would be with my love of all things feminine and my devotion to women , why would you think I was Gay ! 1 in 4 men are supposed to be Gay, But in the Transvestite-Cross-dressing Community the average is 1 in 7 so girls with a TV-CD you are less likely to be dating a Gay man ! strange but true.!!!!!!! Be honest and careful !

  3. Paula says:

    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 that I turned around and headed straight back home.

    Since then, I’ve become a much stronger person and incidents such as these no longer phase me. There’ll always be someone that has something to say, but as long as it’s not threatening or harmful, I just brush it off.

  4. Ragina says:

    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 that conversation, the subject was dropped and didn’t come out again for a long time. When the subjecy did come up again, I was several years older and I was coming out to her, which went well. So I guess that an embarasing moment turned into a good thing in the end.

  5. Racquel Lynn says:

    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 all embarrassed. I think some of them may have been though. lol But I truely think they were okay with it, no one ever said anything to me directly or treated me bad. I seriously think they were afraid to embarrass me or hurt my feelings. Thing is that I don’t mind people cracking jokes if they are not intending to be hateful. I always let people know that it is okay to joke about crossdressing/transsexualism in my presence. I don’t want them to feel like they are going to hurt my feelings. If they do not mean it in a bad way, I won’t take it in a bad way. I rarely take offense when people want to joke a little. It’s obvious when peolpe are joking to be hateful, but I don’t encounter very much of that.

    Anyway, As I have explained before in other posts, I woke up in the hospital after an accident with nothing but a shirt and panties on. I don’t know at what point they had taken my jeans off or who all had seen me in my panties, but that’s also how my parents found out that I like to dress female. I am still working on trying to tell them the rest of the story, that I want to have surgery, but so far, years later, no one has ever even brought up the panties I was wearing in the hospital. But I know it needs to be discussed soon.

    One other time, I woke up to get dressed and walk to the corner Walgreens for my Sunday paper and a few other items. I picked up the jeans I was wearing the night before and was looking all over for my panties and could not find them. So, I just went ahead and got a fresh pair out and put them on and then my jeans and shirt and walked out the door and down the street. Went in the store, got my paper and other things I needed, paid for them and as I was walking out of the store, I looked down and saw my panties I was looking for laying on the sidewalk. They must have been down in the pantsleg of my jeans or something and fell out after a little walking, Anyway, I bent down to pick them up and stuffed them in my pocket and a guy was sitting in front of the store in a pickup truck watching me and I kind of got a funny feeling that he may have thought I was just some kind of pervert. lol Oh well, they were some of my most comfortable panties, so I wasn’t going to leave them there.

  6. cdalyssa says:

    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 blouse was button down, with a ribbon tie at the collar. I even bought a lacy black thong & bra combo. The only thing i did own was a wig from an old Halloween costume. Any ways, I wore that outfit everyday for about a week, until I made a huge mistake. I knew my mom was scheduled to be home for around 6. Unfortunately, I lost track of time and heard my mother scream. I turned around in my new outfit, including makeup, to see my mom standing in the doorway to my bedroom. I sat there stunned in silence until my mom walked away. After I changed, we had a long talk which led to me going to therapy. It helped for a time, but after a few months I found myself dressing up again, buying clothes from Walmart. To this day, my parents & family believe I ended that faze. If they only knew how many times I’ve been in thongs, hose and painted toe nails right under their noses.

  7. rogina garter says:

    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.

  8. Carolyn Ann says:

    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.

  9. 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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