My Most Embarrassing Crossdressing Moment

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.

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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  1. Mona. 4 days ago

    Few of the embarrassing moments I came across are quite similar to ones told above..

    Once I was traveling to Germany where I have had gone out en-femme and felt quite safe. We were group of friends traveling together that time and none had any idea about my cding. Since I had plans to dress up, I had my toes painted in bright red and I was wearing stockings and panties under my clothes. Later we all decided to go for some waterspouts and swimming. I did not realize my mistake until I almost removed my pants only to find the sexy lace top stockings and panties… I immediately pulled my pants up and it was very difficult to convince my friends why I am not getting into the pool or sauna… I had to run back to buy nail paint remover and I cleaned my nails and returned back to enjoy the rest of the day.

    Another occasion was when I was returning from a short walk down the street and the list stopped at the lobby level. 3 teenage girls and 2 boys entered the list and they keep staring at me in turn and they continued to pass some signs to each other while giggling… The moment I got out of the elevator, I heard a loud laughter behind me… I realized that my cover was blown and I was not passable…. But never disheartened.

  2. Terri 6 years ago

    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.



  3. Leslee 6 years ago

    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.

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      Vanessa Law 6 years ago

      Ouch! That’s definitely enough to make a girl blush :) Kudos to your mom for giving them to you anyway :)

  4. Carol 6 years ago

    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.

    • Profile photo of Vanessa Law
      Vanessa Law 6 years ago

      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 :)

  5. Darleen 6 years ago

    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…………..

  6. Vanessa Law 6 years ago

    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 :)

  7. Franny 6 years ago

    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 feeling that I lock the door! When I reached the door knob and tried to turn it, it was lock! I didn’t know what to do, so I went to the side of the house and saw that the rest room window was open. It was kind of high so I placed a milk crate in front of the window and tried to heave myself through the window. I strained with all my might and finally was able to stick my head and shoulders through the window. My butt was now in clear view of any one walking or driving by my house. I started to crawl through and realized that my short skirt was not concealing anything. My stocking clad legs were dangling in the in the air. The vision I envisioned was my panty butt was fully exposed, and it was. Just as I started to go through the window I heard someone yell, “Hey baby you are looking fine”. I went through the window and fell on the bathroom floor. They didn’t see my face but my heart was racing a hundred miles an hour. My panty hose was torn and my baby blue stockings were ruined. That my friends was my most embarrasing moment.

    • Andrea 6 years ago

      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 if you wanna talk some more.

  8. Susan Veronica 6 years ago

    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.

  9. Jeanette 6 years ago

    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 !

  10. Paula 6 years ago

    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.

  11. Ragina 6 years ago

    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.

  12. Racquel Lynn 6 years ago

    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.

  13. cdalyssa 6 years ago

    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.

  14. rogina garter 6 years ago

    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.

  15. Carolyn Ann 6 years ago

    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.

    • Vanessa Law 6 years ago

      Hehe, I’ll bet they had quite a surprise when they walked in on you 😉

  16. Terri 6 years ago


    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

  17. Susan Veronica 6 years ago

    I am in the same position.

  18. Susan Veronica 6 years ago

    I sort of having the same issue.

  19. sashasxycd 5 years ago

    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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