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Thread: embarrassing but funny moments in crossdressing

  1. #26
    Silver Member JoAnne Wheeler's Avatar
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    Going to the door to greet the UPS man while I was partially dressed

    JoAnne Wheeler
    "I'm an all American Bluegrass Girl and Proud As I Can Be"

  2. #27
    Trans Species Joy Carter's Avatar
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    They can take me or leave me as I am. I refuse to react to what others might say. Just give a smile and a wave.

  3. #28
    Gold Member TxKimberly's Avatar
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    I think I may have shared this before but I'm suffering from CRS and I'm not sure.

    When you spend as much time in airports and on airplanes as I do, you can read a LOT of books. As a result, when I get where I'm going, get dressed, and go shopping, I often end up in a book store.

    So here I am, presenting as a female, paying for my books, and the lady asks me if I have one of their reward cards.
    "I AM a member, but didn't bring it with me" I told her
    "That's no problem, whats your phone number? I can look it up that way!"
    I gave her my phone number and she looks it up on her PC. By way of verifying she has the right account, she looks at me and calls me by my wifes name.
    "Dawn XXXXX?" she says with a smile. Out of sheer habit and running on autopilot, I responded.
    "Nah, that's my wife!" As soon as the words left my lips I realized what I had just done. I had to stop myself from yelling "DOH!" like Homer Simpson.

  4. #29
    Junior Member StephiefromSyr's Avatar
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    Only once i've had some embarrassing story happen. One day at a payless in guy mode i was out pretending to check out new sneakers, well right behind my size is the female size of me. I picked out 2 different sets of heels and walked out. Sure enough i get home and one pair is slightly to big. So I go the next day to return it. So I go in and explain I needed to exchange for a smaller size for my gf, the girl at the counter says ok go right ahead and i go over to the aisle and grab the next half size down and figure I should be smart this time and try it on. Well dummy me forgot payless' policy and 3 seconds after i get the heel on she came around the corner and asked if i needed assistance. I must have turned beet red as i said i was all set and took the long walk to the counter.

  5. #30
    Senior Age Member sissystephanie's Avatar
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    Very embarrassing, but not funny!

    On a warm day early last fall, I decided to go to a local Sam's Club to pick up a few things. Most of you know that I go out dressed but looking like a man. No wig and no makeup! I wore a tight knit top with my usual bra covering my natural 40 B's and a pair of black leather Hotpants over hot pink satin panties. Did my shopping, with only a few "doubletakes," and a compliment from the checker who liked my outfit. Then, since this Sam's Club has a gas station I decided to go there. Drove over, parked at the pump and got out the car. Ooops! The side zipper on the Hotpants had come undone and there was no hook and eye, and as I stepped out of the car they fell down to my ankles! There I was, standing by my car wearing my knit top and pink satin panties!! Talk about exposing yourself!! I quickly pulled up the Hotpants as I looked around to see if anybody was looking. Luckily, no one was!! I pulled them up in place and fastened them properly. Haven't worn them since! Think I will take them to the lady who does my alterations and have a hook and eye put in!
    Stephanie

    Lady on the outside, but man underneath!

  6. #31
    Banned Read only Sakura Rini's Avatar
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    i was kinda embarrassed when i ordered some clothes off the net and when they wear delivered the parcel was sitting on the dinner table and my mum ask did you order a "dress" because on the label it had dress. i made up some lie about it being t-shirts i had ordered and dress just meant clothes, lol

  7. #32
    Lady By Choice Leslie Langford's Avatar
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    Quote Originally Posted by TxKimberly View Post
    I think I may have shared this before but I'm suffering from CRS and I'm not sure.

    So here I am, presenting as a female, paying for my books, and the lady asks me if I have one of their reward cards.
    "I AM a member, but didn't bring it with me" I told her
    "That's no problem, whats your phone number? I can look it up that way!"
    I gave her my phone number and she looks it up on her PC. By way of verifying she has the right account, she looks at me and calls me by my wifes name.
    "Dawn XXXXX?" she says with a smile. Out of sheer habit and running on autopilot, I responded.
    "Nah, that's my wife!" As soon as the words left my lips I realized what I had just done. I had to stop myself from yelling "DOH!" like Homer Simpson.
    Well...not necessarily. Who's to say you weren't doing an Ellen de Generes and had a same sex spouse? Judging by the popularity of her show, aside from a few redneck parts of the U.S., seems as if a lot of people are O.K. with that type of union nowadays.

    Just tonight, Ellen did a spoof of the Newlywed Game on her show, with her and her partner Portia di Rossi in a mock competition with a straight couple, and the audience just lapped it up.

    B.T.W., the straight couple won the contest and the prize, but that really was a "gimme". You can only push the envelope so far at any given time..."baby steps, baby steps", as we are so fond of saying here on this forum.

  8. #33
    Silver Member Leslie Mary S's Avatar
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    Well here we go. First a bit of staging.
    I have two younger people that now live with me. One is a lady of 35 that I call 'Daughter'. The other is a male class mate. 'M' is 38. All three of use go to collage and even have some of the same classes.
    It is not unusual for me to dress out around the house. They both know about it and support me. We fequently go out as a threesome. I am just starting to come out of the closet but rarely go to town in fem and untill this weekend alone.
    Anyway “M” had gone had gone home for the night the night before. Daughter and I were in the living room. She, in her bathrob, and I in a T-top, mini-skit, and low heels, with only lipstick and eyebrow liner makeup on. When what do we hear but 'M' is at the locked door. ‘M’ doesn't have a key. I went to unlock the door and what do I see but ‘M’ with his dad in tow.
    I don't know if his dad knows who my dab self is or that I CDer. So I go into full ‘Leslie’ mode. Here in my own home is an unexpected guest.
    I don't know to this day if I pulled it off last Friday.
    I did tell 'M' to never bring in a guest without first advising in advance.

    On a side note:

    Yesterday I got a small complement. I was Leslie and went to get a sandwich for us girls. The young man at the drive thru window said " Thank you mam‘ will there be anything else for you mam’?", an unsolicited comment of my femininity. I felt great! I was accepted as female in this straight laced Bible Belt community.

  9. #34
    Junior Member ChibiKaiju's Avatar
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    Was in a Payless last night with my fiancee, I was hoping to get some shoes for our honeymoon (going to toronto, and the only other shoes I have are mary janes and they're missing), started out kind of nervous but eventually found something I liked and we were talking a bit bolder, when all of a sudden the SA asks if we need any help from the other side of the shelf! Now I know they have great customer service but atleast give me a chance to hide my evidence lol

  10. #35
    Life, only in color! MAJESTYK's Avatar
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    Anniversary, the musical

    I have actually been waiting for a moment to happen......This morning it did.
    I was in the kitchen adjusting the "girls" and noticed through the miracles of science and an ill fitting bra, the left one well, SQUEAKED!
    Upon noticing and being able to repeat, this phenomenon, I had to share this hillarity. When I showed the new found musical boobie to my wife , she directly tried it out, thinking of course that I had used the dog's squeaky toy to fill out my bra and amuse her as it's our annivesary today and I could think of nothing that says "Happy Anniversary Honee" more than musical boobies.
    As my lovely spouse poked he aforementioned breast to see is she could also make make melodious humour in the key of "D", she then realized I had NOT used the dogs playthings to fill out my bra to which both of us were extremely suprised all though in different ways.As my lovely Lady is a very private person and doesnt usually go around "feeling me up" she proceeded to turn the loveliest shade of red and I turned the loveliest shade of blush. Now, being absolutely mortifed, she began to appologise profusley and I backed away and went to put on a slightly better fitting although less musical article of under clothes.
    Well behaved Women rarely make history

  11. #36
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    This requires a bit of backstory;

    I work an odd shift - when I leave for work, the average person is going home, when I get home, they're long asleep, when I wake up, they're at work.

    Additionally, on Fridays I'm pretty much left in the warehouse alone for the majority of my shift. The perfect opportunity for cross-dressing... to an extent.

    I get home from one such adventurous Friday, and I hear an odd noise; talking coming from the basement... My room is also in the basement. And under my work uniform my chest is about three cup sizes larger than normal. The only saving grace is that it was still around -16C outside and I had my winter coat on (Bulky enough to hide at least an additional two cup sizes with some effort)... Apparently one of my house mates had a friend over doing something-or-other... Luckily no-one noticed anything amiss as I hurried through introductions and then rushed into my room to remove the forms...

    That was probably the closest I've come yet to being caught by friends... If I had been a bit more tired from my shift, and they had been a bit quieter...

  12. #37
    Silver Member kellycan27's Avatar
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    while taking a kickboxing class I was distracted by a cute guy who was sparing with another student right behind my sparring partner. Not paying attention I caught a kick square in the nose. No big deal. no damage done. After my lesson I went to join some friends for lunch, and when I walked in everyone just sort of gasped.. My g/f led me into the ladies room and when I looked in the mirror I saw the beginnings of two shiners. By the end of the day, both eyes were black and blue.. On Monday morning I walked into my office wearing a pair of oversized sunglasses. Needless to say it wasn't a very good cover-up. My employer was concerned about what our clients might think. I said... well if they ask I'll just tell them that I have a very tough boss. I got a few days off . With pay!
    Last edited by kellycan27; 03-22-2009 at 02:24 PM.
    "one day I'll fly away..... leave all this to yesterday"

    http://youtu.be/kR7NlgwVHHg

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