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cross dressing mishaps and fails

21 Posts
14 Users
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Posts: 1766
Duchess
Topic starter
(@fiona06)
Famed Member     Bolton, Lancashire, United Kingdom
Joined: 6 years ago

ok girls. I wanted to post something light hearted and humorous for us all to enjoy, share stories and above all laugh! do you have any funny stories regarding your cross dressing, however trivial? lets keep this funny, no sad stories or negativity please!

i'll add one funny story and it was a complete oversight. I bought a lovely pair of soft, black tights and was looking so forward to wearing them, so forward in fact that I totally forgot to trim my toe nails and my tights had the longest rip marks anyone had ever seen! gutted! lesson learned!

fiona xx

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20 Replies
Posts: 1264
(@bianca)
Noble Member     GB
Joined: 8 years ago

Hi Fiona

When I go out I usually dress en femme in the house and put on some jogging trousers and a hoody to cover up.Then head for the car with my bag full of make up, wig, shoes, jacket, accessories etc etc (its a big bag😂)

I then drive to a secluded country lay-bys or car park where I transform into Bianca, then change back when I have to😢 return home.

One day as I was returning I looked in my rear view mirror reversing into my driveway, and to my horror saw my gorgeous clip on pearl earrings still adorning my ears. I had driven through my hometown in drab, with my earrings on, and I have a hairstyle similar to Bruce Willis 😂

I have no idea if I was clocked with my earrings on.

love

Bianca

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Posts: 1766
Duchess
Topic starter
(@fiona06)
Famed Member     Bolton, Lancashire, United Kingdom
Joined: 6 years ago

lovely story Bianca!  ha ha i can just imagine you driving home! 🙂 keep the stories coming girls!

fiona xx

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Posts: 2144
(@cyberian2)
Noble Member     Elliot Lake, Ontario, Canada
Joined: 8 years ago

Fiona........destroying tights.........you win The Fail Army award this week! LOL.

Dame Veronica

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Posts: 2144
(@cyberian2)
Noble Member     Elliot Lake, Ontario, Canada
Joined: 8 years ago

Bianca......that story and description gave me chills.............Bruce Willis in earings......screeeeeech!

Dame Veronica

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Posts: 0
Guest
(@Anonymous)
New Member
Joined: 1 second ago

A long time ago I had accepted to meet with somebody from a chat room and Sunce I wasn’t totally sure this person was legit, I asked my friend Rose to join me and we were at the restaurant where I had agreed to meet “Mike”. (No not a date!).

Anyway, he was a no show so we had some coffee and pie and when in line at the register Rose ask me “so how’s your wife?”  I was quick to answer “his wife is fine”. Luckily the two or three people in the line either didn’t connect the “your wife” with me, or thougth it has been just some mistake. Still, don’t ask stuff like that in public!!!

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Posts: 2023
Baroness
(@ryanpaul)
Famed Member     Outer Eastern Suburbs Melbourne, Victoria, Australia
Joined: 7 years ago

Hi everyone.

"Frustrated author" here and I've learned the hard way that links from other sites that  incorporating links here does not always "come out the 'other end"

In my business career I spent a good 30 plus years "on the road" and that's when Caty would emerge in her hotel room etc.

So over the 30 years some quite funny and also quite serious events occured.

If you google "Tales of a Travelling Tranny" you'll see the whole "shooting match".

EG. The zip on my garment bag let go on a trip to Stockholm in Sweden. Luckily all Caty's "Intimate apparel" was in shopping bags inside that pocket. But they were  merrily going around on the carousel when I got to baggage collection

To quote Jimmy Buffet from "He Went to Paris".

"Some of it was magic, some of it was tragic, but I've had a good life along the way"

 

Caty

 

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Posts: 0
Guest
(@Anonymous)
New Member
Joined: 1 second ago

I get the horses ass award this week: pardon my language. We were talking about cosplay on here last week and I commented about my nurses costume. So it got me thinking, Should go over to my friends place and put on my outfit and surprise him when he got home from work. So I slip in to his place and get dressed, white PVC nurses dress, very short, red stockings, white PVC thigh highs, with a long blonde wig and red lipstick. Well I was in the bedroom and heard the door open and strutted out in a very seductive manor and said, hey baby does this get more than your temperature up and as I turned the corner he was standing there with his sister, who I've never met before! Oh boy, I just wanted to die, she knows my friend is gay and says, well does it and starts to laugh. We were introduced and she left a little while after. I've had a lot of dumb moments but this one just took the cake. Thankfully my friend has a great sense of humour and we laughed at it and he told me he really did like my outfit. We made out for a bit and had a great evening.

If you can't laugh at yourself, you do have a problem.

Take care, Heather, the incredibly dumb blonde.

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Posts: 46
Lady
(@biolass1000)
Trusted Member     Michigan, United States of America
Joined: 6 years ago

Not sure whether the fault is mine of the manufacturer's but here it is. So here I am getting ready to see Amelia for the first time as well as showing my mom me in full femme for the first time. I managed to get my lower body dressed without much difficulty. However, once I put on my only  pocket bra, one of the straps unraveled. Luckily, I was able to tie it back on to salvage it and my mom offered to repair it.

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Posts: 358
Lady
(@nancygamms)
Reputable Member     South Carolina, United States of America
Joined: 8 years ago

Wore nail polish to the hotel gym, it was light pink and not very noticeable.

Worst was in Green Bay in the flower skirt in my pic by lambeau field.  I had just gotten that skirt at goodwill and I'd not worn that skirt out.  I got gas, got a beer at a tavern and returned to the hotel.  I was waiting at the elevator which is across from the restaurant/ bar and near the check in desk.  As I stopped by the elevator my skirt literally drop to the floor.  I yanked it up very quickly, never turned around, and got on the elevator as soon as it arrived.  I have no idea if anyone saw me standing in my pantyhose and panties or not.  The next morning I was trying to figure out the site lines and their is furniture, columns, and no one should have been facing me except maybe the desk clerk.

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Posts: 11
Lady
(@lizzy)
Active Member     ZuidHolland, Netherlands
Joined: 6 years ago

Go on a journey with me!

 

Imagine a hotel. Classy but not too expensive, in the city center of a town in the Netherlands. It is your first time going out dressed, nerves coursing through your body as you get ready. You slip on the lingerie, do the make-up, put on that special outfit, style the wig and on go to heels. The brand new, pink shiny high heels that fit perfectly.

 

Googlemaps says it's a 7 minute walk to the party you'll be attending.

 

You go outside and this is the first time you realize the hotel is right next to a mosque. You start realizing the route takes you right across the busiest square in the city.

 

Aaand you realize the entire route is made out of mothereffingharrypottersbrokenbroomstickandholyhellcownsonwheels... COBBLESTONES.

 

Well google...it takes about 20 minutes. and it'll damage your brandspanking new heels.

 

 

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Posts: 121
Lady
(@mandycericross)
Estimable Member     Cheshire, United Kingdom
Joined: 6 years ago

Ok, I'll add to this then 😉

This happened a few years ago when I was just really starting to venture outside crossdressed. I was about 9pm and I'd scoped out a safe quiet route round a local park near me that had a fairly well lit car park near an athletic stadium that I thought I had the courage to cross, the stadium was generally a day time thing so figured I'd be ok.

Anyway, started my walk away from my car, looping round to the car park and the athletic stadium, got to the well lit car park, took a deep breath and started to cross over when suddenly a local women's running club consisting of about 30 -40 women pile out of the stadium gates en mass towards me, all round me and past me!

I was literally frozen to the spot in terror in the middle of the car park in my hot little mini skirt, heels, stockings etc as all these women runners dodged round me and on into the night!

Needless to say I was a bit more wary of that spot on future strolls out I can tell you!

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Posts: 149
(@skyler1090)
Estimable Member     Chicago, Illinois, United States of America
Joined: 6 years ago

Well I underdress (bra, panties, cami) every day as I can’t fully dress at work. So yesterday I was sitting at my desk, only weirdo in the office at 4am, clearing some paperwork and one of the girls I’ve become pretty good friends with came up behind me. Leaned over and whispered “That color is cute on you. Just wanted to let you know before someone else notices sweetie.” Well apparently in my rush to get into the office, I hadn’t checked how opaque my shirt was. My bright red bra straps were showing right through. Rushed for a sweater to cover up and spent the rest of the day sweating my tits off lol. Super glad she was so relaxed about it and didn’t make a big scene. Talked at lunch and told her quite a bit. Nice to have someone who knows other than my therapist and fiancé lol.

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Posts: 594
(@myfanwy)
Honorable Member     Mid Glamorgan, United Kingdom
Joined: 6 years ago

Not so much of a mishap but a bit of a close call.When I was in my late teens or early twenties I was dressed in my bedroom wearing one of my mothers skirts and pantyhose.I heard a ring at the doorbell.My heart sank as I probably thought that my mum had forgotten her key.I quickly dressed in my boy clothes over my tights.I answered the door to two gas engineers who had come to pickup an unwanted gas appliance.Although they could not see the hose under my trousers I felt uneasy and nervous.They picked up on my discomfort I think.They give me a form to sign,I shook as I signed my name.They must have guessed I was up to something naughty.However,what a relief that they didn't see me in girl mode.Very sensibly,I always took the precaution of drawing the curtains when dressed up when my parents were out.

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Posts: 0
Guest
(@Anonymous)
New Member
Joined: 1 second ago

Enjoying a dress day... the doorbell rang! I quickly slipped on my bathrobe, opened the door, accepted and signed. Only after I’d closed the door I realised that I’d presented two inches of dress hem below the robe along with black opaques and flat shoes with cute bows... along with C cup boobs. 🙈

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