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So here’s an interesting question for our public going cd sisters
What is the most embarrassing thing that has ever happened to you or a friend while out in public? I’ve got one that’s a real whopper. several years ago one of our members from our support group was traveling en femme in a major department stores, Sears or Penney’s or Macy’s. She was in the lingerie department when her too large panties happened to slide down her thighs and end up on the floor. She unobtrusively stepped out of them and left them. Though not wishing to put them back on in plain sight, she turned around a few minutes later and one of the lingerie clerks had spotted those panties on the floor and thinking they fell off the table picked them up and delicately folded them and put them back on the panties Table- on very top of the pile!
A month later after our monthly newsletter when out to members an out of town person said to my girlfriend “ So you’re the lady who lost her panties in Penney’s eh?!”
Now that’s one heck of a whopper TRUE story, try to beat that sisters.
Wow can any one beat that? I can only offer the time I wore a ‘plunge’ bra.
Back in the day when I was getting out more I had found some silicone boosters which fitted well into the bra and enhanced my bust nicely giving me that added confidence. They replaced the lighter foam ones I had constructed myself.
I was in a shop and went to take something off a shelf when I felt something slip under the bra and plunge straight down my front and onto the floor. It took a second to realise just what it was and there on the floor was an insert! I stood one boob up and one boob down. I promptly dropped my basket over it and collected my thoughts. Looking round everyone was still milling around and no eyes looking straight at me. I crouched down and as careful as I could picked up the form and dropped it into the pocket of my coat. Pulling my coat around me I paid for the goods and made my way to the ladies room and re balanced my chest. I think I got away with it.
What I did learn from that was I was not wearing the correct size bra so went the next band size down and my bust lived happily ever after.
A few years ago, I decided to catch a matinee at the local cinema. If I recall correctly, I was wearing my black and white gingham sundress with a white belt. Being a little rushed to catch the show, I was still putting the belt on as I ran out of the house. Somehow, I manage to get the back hem of the skirt caught in the belt. Unaware of this, I parked my vehicle and walked into the theatre and across the lobby to the concession stand while showing off my panties to all the world. Fortunately, it was a slow day at the cinema so I was able to avoid complete embarassment. At the concession stand, I was thankfully saved by two older ladies who politely informed me of my faux pas.
MacKenzie Alexandra
A few years ago I was on a business trip in Florida. So excited to have some time enfemme, I packed a couple of outfits, makeup, and all and checked into the hotel a day early so I would have some time for myself. The hotel where I was staying had rooms that exited directly to street level so I wouldn’t have to go through a lobby. I took my time, showered, did my makeup and got dressed and left to have a fun day out shopping. Arriving back at the hotel around dinner hour to drop off my packages, I took out the card key for the room and swiped it in the door. ‘Red’ light, and the door did not open. Tried again, same result. Bit of panic. Tried a few more times and couldn’t get the door to open. Was just about to go to the hotel desk and ask for a replacement key, expecting to have to explain myself and not knowing what to expect. Heart pounding, I tried the door one last time and got a green light and the door unlocked. Panic averted. I think if the same thing would happen today, I wouldn’t be as unnerved, but that was in the early days of full up dressing, when I felt like everyone could see right through you. Much more confident now, and don’t care as much about what the next person thinks as long as I am happy.
Love,
Rachel.
Rachel,
I had a similar experience. I was on a business trip and one evening I did exactly as you. Took my time, got all dolled up but wore “normal” female clothes for simply going out shopping. When I got back to the hotel, it was dark and I used a side entrance. Insert the key…nothing. Not working. Tried a few more times with the same result. So I walked around the front of the building trying to get the nerve up to go to the front desk when, now in a more lit area, I realized the key was UPSIDE DOWN. Good grief! So I went back and inserted the key correctly and everything worked. Problem resolved. Boy did my heart pound there for awhile. Lol
Hugs… Dana
I had bought a skirt with an elastic band at a thrift store on a work trip and had not had a chance to wear it out until another work trip a few weeks later to Green Bay. I had stayed in this hotel many times and there is a small restaurant/bar area across the lobby from the elevators with some furniture (couches and such) in the lobby area between the two. You pass the front desk to get to the elevators. I did have my key not work once and had to show idea there without incident. I had eaten there a few times and even had the same waitress two nights in a row, once as Nancy and once in drab.
This time I went to Target and Walgreens and came back with a bag that I was going to take to my room and then come back to eat provided it seemed low key and safe. The clerk was checking someone in as i walked by and there were a few guys sitting at the bar and high tops mostly talking and watching tv. As i stood in front of the elevator waiting my skirt suddenly dropped to the floor around my ankles. I quickly pulled it up, stared straight ahead and got on the elevator with arrived about 10-25 seconds later. I changed and went to eat in drab.
At that point I was checking out all the site lines and am not sure anyone even saw or noticed and no once had a great line of site but the clerk who was occupied. I don’t have that skirt anymore.
One night at a dance club, my guy was getting too frisky with his hands and my panties slipped down to my ankles! It is quite impossible to dance with panties around you feet, so I stepped out of them and left them on the floor. After returning to our table, a waitress approached with my panties saying “Excuse me Miss, but I think these are yours.” and dropped them next to our drinks. I nearly died of embarrassment!
For me there have been a few incidents that have been embarrassing while out in public.
Back in the mid 90’s I worked as a manager of a group of aircraft mechanics, so had to keep up appearances and therefore couldn’t grow my hair long. At the time, I was also sidelining with someone that owned his own business working with dry cleaners, basically doing pipe fitting. This friend I had met through a a Crossdressing group in South Florida. At the time, I was rather shy but passed pretty easily. At least every week or week and a half he would convince me to go out as girlfriends to many different events. So one night he planned to go roller skating at an indoor rink. I was quite rusty and spent a good amount of time squarely on my butt. One of those times my wig went flying. I overheard as I was scampering to get my hair “OMG, she lost her wig.” From a girl going by. She got to the wig before I could retrieve it then assisted me on the floor and in the ladies with straightening myself out. It was good, but was embarrassing. Another time after I’d left aviation, I’d been growing my hair out, but was marked by a clerk at a department store. She had evidently had a bad experience sometime in the past and completely broke down while trying to check out with a couple of blouses and a skirt. The manager had to finish the transaction, I really felt badly for her, and myself too as all the other shoppers figured it out about the same time. Yet another time, I was out with a coworker (don’t remember how she figured out that I was a CD) but she wanted to see Jessica and we did a day of thrift shopping together. While I was in the changing room trying on some things, someone stole the wallet out of her purse. The cops were called, and although they were really quite respectful, they knew after looking at my drivers license.
For the first dozen times I went out en femme I left the house male & changed in my car. One day I pulled into a mall parking lot and changed into a long sleeve t-shirt tucked into a denim skirt. I got out to walk to the mall entrance without realizing that, in all the contortions involved dressing in a car, one of my boobs had slipped out of my bra and was sitting down by my waist. I had a belly boob! I held my pocketbook in front of the wayward boob, walked back to the car and corrected my anatomy. It’s tough being a woman.
“off topic” a bit I know but…
One of my frequent cities I used to travel for work to was dear old Montreal Canada. The “widget” company” I worked for only made small items so I could carry quite a few in my luggage. I was always a “good girl” and declared my samples on all customs decs. Mostly no more than $20.00 worth.
The only airport worldwide where I was told to go through the “red inspection lane” was Montreal… Sorry if I offend anyone, but those pesky French Canadians gave me a lot of grief on some of my trips!!!
So I quickly mumbled “private room” and avoided the full public humiliation.
I’ve already posted on here about driving around industrial estates in Perth Western Oz in the middle of the night, playing “female rep” The cops pulled me up and after being satisfied I was not up to no good, told me to “go back to your hotel,…. sir”
Another time at Stockholm airport Sweden, ( I was not femme) the zip let go on my garment bag and all Caty frillies, (luckily all in plastic shopping bags) were merrily sashaying around the baggage carousel. Got em” gathered up”, and got “out there” very quickly
Caty
I forgot this one,
Whilst staying at my favorite self contained apartment chain, I went shopping en femme. Got back to the entrance to the underground parking and found i could not get my keycard to lift the garage door. So out came the receptionist to let me in.
I just took off my wig and said, “I look a bit different”
She just smiled and opened the door….
I’m down there about once a month and have been doing so for many years. The staff, rooms and amenities are great and I’ve made a “business friend” or two with the management and office staff.
Still love to look at my personal “incident file”.. tho to see if that day gets a mention
Caty.
Last winter I decided to go out completely dressed for my second time. I went at night to a local Walmart that is not too busy. I wanted to buy a woman’s winter coat, while I was trying on a cute, pink waist length jacket with hood the zipper jammed, and I was unable to slide the zipper down. I thought about trying to pull the jacket over my head but was afraid of pulling off my wig. I also thought about just breaking the zipper to get it off, but it was too strong. I must have stood there for a few minutes trying to get it off and thought about going to a dressing room to get it off when it finally became free. I put another one like it in my cart went to the checkout, paid and left.
Love
Rose
I was stopped by a police car on a corner of two streets in downtown Frankfurt while walking home en femme. They had been alerted by someone who had read me short before when I was taking photos of myself, and who claimed that I was secretly taking pictures of girls. I showed the two young policemen that the only “girl” on my camera was me and after they had run my ID through their computer and had convinced themselves that I was not some police-known pervert, they let me go. Unfortunately, I did not have the guts to ask for a “selfie” with them. My profile picture happens to be from that day and one more of my public photos. Love, Franzi
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Great stories from all. Since I only started going out publicly in 2022 I don’t have many funny/embarrassing stories. Probably the funniest were both in Victorias Secrets stores… one in Denver, and one in Dallas. In Denver I strutted into a VS store in the Cherry Hills mall and a sales associate looked at me and asked “Would you like a free bra fitting today”. I stuttered out a “No thank you” and the look on her face hearing my voice was priceless.
The second time was my November trip where I visited the Grapevine Mall north of DFW airport. When I walked in the VS I was again greeted by a sales associate asking if she could help. Much more brave this time, I told her I was looking for a specific panty style I had purchased at another VS. She clocked me and got just a little flustered as she walked me around the store and pointed out panties that were not the specific type I wanted. So I stood there, with many others around explaining the style “They are a string bikini, with adjustable bands to tighten or loosen:” As I said that I didn’t realize I was mimicking how they adjusted with hand motions around my hips… I had her red faced and several other patrons staring. Was a little embarrassed myself.
I have two stories – both of which I have shared on CDH years ago so if you an an ‘old timer’ please forgive me for being repetitiously redundant.
First – I stopped for gas at my regular place in man mode. I had been there many times before both en femme and in man mode – but apparently the store workers had not connected the dots. The attendant asked me if anyone had ever told me I look like Bob Newhart. I said ‘yes many times’ then asked “who do I look like in lady clothes?” She replied “IS THAT YOU?!!!”
Second – I was not out at this time but would answer the door en femme, normally it was a maintenance worker, a package delivery person, or a church recruiter so no big deal if they saw me in lady clothes. I was dressed my best when the doorbell rang, I opened the door, there stood my next door neighbor. Deep breath, then I asked him to come in. A tree had fallen from my yard into his, he didn’t have a chain saw, didn’t know how to run one even if he did, could we work on it together over the weekend. It was so bizarre me standing there in full lady wear talking about chainsaws with my neighbor. Coincidentally we had worked for the same company (I was retired at the time) and in the same building. So no doubt in a few hours everyone at my former workplace knew about Elaine. I would have loved to be a fly on the wall and hear my former workmates conversation.
Hi, I’m sort of late to the party, but I had an embarrassing experience while out publicly en femme – like getting arrested! I came across your article and became intrigued with Franziska Frankfurt’s subsequent article(s) about her run in with her local police. I responded to her article directly, then realized I should have maybe responded here as well. In any case, I wrote an article about my experience on CDH a few years back and since it is lengthy, I offer it as an addition to your collection of “Worst or Funniest Embarrassing Moments while out Publicly En Femme”. What had started out as a most embarrassing moment, eventually became my best crossdressing experience ever (to date).
https://www.crossdresserheaven.com/my-best-experience-crossdressed/
I guess i missed this topic earlier, so i will add my two cents (or is that fifty cents with inflation…neither here nor there)
My very first outing dressed up was embarrassing. Maybe not so much as embarrassment as sheer panic attack but I believe it qualifies here.
I had bought a nice, long sleeve leopard print blouse that was long enough to almost be a dress. I also bought my first pair of black leggings at the same time that I bought the blouse. Not long afterward, i bought a wig at an adult store. I was home alone for a week when the idea occurred to me to dress up fully. I Showered with “pretty” smelling shampoo and soap, and put on my new outfit and wig. I also found some makeup in the “samples”bag my wife had for selling Avon. Mascara, a little bit of eye liner, and a nice red lipstick. I was over the top with the look. I paired the outfit with my high heeled booties and decided I would drive around for a bit. It was dark and late and I was not in my right mind. I grabbed my keys and my wallet. I drove a bit, and even got out in a couple of parking lots just to walk a little bit my first time out as Tiffany. I drove a long way, feeling free. All of a sudden, my low fuel light came on and the audible low fuel alarm rang out loudly. I suddenly realized I did not have enough fuel to make it home, and I would have to stop for fuel. Now i was in an area that is a bit “touristy” and everything is open late, as traffic doesn’t die down completely until after midnight. I pulled into a fuel station and sat there gathering up courage. I made no eye contact with anyone when I got out, including the person on the other side of the fuel pump where I was. My wig was rather long, so i just let the hair fall down hiding most of my face. Fortunately i could pay at the pump with a credit card so i didn’t have to go inside to pay. I know people saw me as i stood there pumping gas. Busy intersection, all the fuel pumps in use… I mean, hey… how many times do you see a woman pumping gas dressed like she was ready to party, wearing high heels? I thought I was going to have a heart attack that night. I made it home though. And figured since I had just gone through what I did, that i wouldn’t park in the garage. I parked outside and walked up the sidewalk with my little bit of newly found emboldened confidence, back into my house.
Tiffany
I was in a Michael’s store wearing a tank top button front summer dress. It was not the first time that I had worn it and did notice a problem, but never fixed it.
The buttonholes were a little too large and the buttons slipped out easily. This had happened the two times that I had worn it in the past, but the problem only showed up at the bottom, by my knees, which was not really a concern.
So, here I am shopping, moving around, bending up and down, and I didn’t realize that buttons started coming undone. I was in an aisle alone when a woman walked into it, took a look at me, and quickly left. It was then that I noticed that the top three buttons had come undone, the dress was wide open, and I was walking around with my white bra completely exposed.
I fixed myself back up and went to look for the woman to explain but could not find her in the store. Needless to say, I have since stitched up the buttonholes tighter.
In reality, I was not very embarrassed. Everyone has experienced an undone zipper, split pants, or some other mishap. I just think of it as a humorous story that I can tell.
Having just gone out for the very first time last week I can relate a quick story. I planned to walk one full city block and hustle back to my car. I thought I had thoroughly researched the route I would walk (for minimal foot traffic) only to discover as I made the first corner that I had to pass a bus stop with 15-20 people waiting. With heart pounding I walked on, terribly overdressed, with all eyes on me. There was a crossdresser in the crowd who shouted out to me repeatedly, “I see you sister” which terrified me further. I confess I took a shortcut back to the safety of my car and had a good laugh once the heart attack subsided.
MeganFrom this Meghan to you Megan- 15 or so years ago I was at an all gender mostly straight club that had a Halloween party so I went in my favorite Saloon Girl costume dress. I’ve worn it several years so it’s worn out (see public pictures- shows a montage) So I’m sitting on the bar stool with my legs crossed and feel the roughness rubbing of the crinoline petticoat against my tush! It was then I had forgot to put on my panties underneath before leaving house!🤪
I’ve got one embarrassing story, and one which is funny. It would have been embarrassing until I just owned it.
One night my friend held a party mid week. I did some basic makeup in my office (I locked myself in so no one would come in) and finished changing in the car. Before going to my friend I stopped in the Dress Barn near my office. I didn’t find anything but as I was leaving, one of the sales associates told me that the hem of the skirt was tucked in my waistband. I quickly fixed it before heading out to the car and to my friend’s party.
Another time she had a fairy party. This began at 4:00 on a Sunday afternoon. I wore my short pink maid’s dress sans apron (I have shirts longer than this dress) with a tutu petticoat for a bit of modesty. I had on a tiara on my head. I found a glow stick with a star topping which was my magic wand. And I made myself some wings with two wire hangers, some string and glue to keep them together, some sparkly translusent wide ribbon to form the wings, and some elastic cord to put the wings on like a back pack. I got to my friend’s home, parked a little down the street, and put the wings on. I started to get out of the car and I saw a man down the street the other way walking his dog. I quickly retreated into my car. I waited a few minutes but he did not disappear. I finally said the hell with it and owned the situation. I got out of my car, shut the door (which is always with a bit of a slam), and walked to my friend’s home. I never looked back to see if the sound of the car door closing made him look and see someone dressed as a fairy walking down the street.
Wasn’t an almost got caught moment but still funny. I was recovering from a broken femur last fall. I have always had my long hair and many times to the shoulder. Well when I broke the bone I was in the hospital, then rehab, then PT (physical therapy) at home. Needless to say getting a hair cut was not on my list of things to do. But my SO, better known as my wife, needed to go to SAMS club, I wanted out of the house, so I painfully tagged along. When we got to the store I used a store scooter to drive around in. Traveling down an aisle a male worker walks by us and says “How are you ladies today!” I didn’t think much of it. I was wearing an oversized jeans jacket and a very old pair of faded bell bottoms I still kept. Needless to say it still made me feel good. Later on I was at the meat department by myself when a female worker asked “are you looking for anything in particular, ma’am!” Wow! 2 for 2 without even trying. Finally we made it the check out counter. Once payment was made the cashier said “Have a nice day ladies!”
Once in the truck, my wife turned to me and said that I needed a haircut or get it styled, one or the other. I don’t think we would have made the same choice! C,d’
Looking back on these events, I wasn’t embarrassed at all, I just hope the wife wasn’t.Like a few others, I too had a problem with my motel card key on a business trip, but it wasn’t that the card didn’t work.
My business trip was to a nearby city where I decided I would finally go out in public dressed for the first time. I planned everything down to the last detail, including my outfit, where I would go, when I would leave the motel room, etc. I even practiced how I would respond if a cop pulled me over. I was ready for every eventuality, except one.
Once I got checked into my motel room, I started getting ready for my first public adventure. I put on my makeup, wig and pink fingernail polish and dressed in a gray satin blouse with a long black and gray plaid skirt and black leather boots. Once dressed and with my heart pounding in my chest, I left the safety of my motel room and quickly jumped in my car to drive around.
I had a blast and felt so free driving around the city and presenting as a woman (at least as a woman driver). I walked around a mall parking lot and even stopped to buy gas at the pump. When I returned to the motel, however, I couldn’t find my card key. I was in a panic and tore my car apart trying to find the key. I soon realized that in my excitement, I’d left the card key on the bed in my motel room. I was locked out and would have to get a new card key from the front desk.
I drove to the front of the motel and waited. When the coast was clear from any guests, I walked into the lobby and to the front desk. The gentleman working the front desk was very professional (I’m sure I wasn’t the first crossdresser he’d ever seen) and, once I explained my problem and showed my male ID, he gave me a new card key for my room. Now days this wouldn’t be embarrassing to me but for my first time out in public fully dressed I was definitely red faced under my makeup!
Tiffany the dreaded hotel key card issue while crossdressed. My story, I was wearing a cute dress and heels and I’m sure I looked darling from a distance as I approached the hotel side entrance that required a key mine would not work after several attempts a man in the parking lot noticed this women in a cute dress and heels struggling so he came to my rescue I thanked him I’m sure he was shocked.
Today, I went out for some exercise while wearing half and half women’s/men’s clothing, and underdressed while wearing forms. I thought that I could get away with that by being subtle enough. Men’s sunhat and a moustache.
On a sidewalk, a man came towards me. He took an obvious look and his pointing finger came up. I thought, here we go.
He asked, “Are you a man or a girl?” Not man or woman, he had to use the word girl. This happened once before, too, with a woman asking a similar question.
I stopped, turned to face him (just for security reasons) and asked, “Does it matter?” He said no, so I said thank you and continued my walk.
He wasn’t finished, though, so he said, “I was just asking…” He had to have the last word, I guess.
No harm done, but we do have to keep aware of circumstances.
Harriette,
In these parts, a stranger coming out with a question like that would be considered the height of rudeness, and yes, I too would keep a close watch on him, until I was a safe distance away from him. Of course, we have pan handlers and homeless in some parts of the city who may come out with something like that, but that is expected behavior from them.
I can recall a small child in a store, with her parents in the check-out line, looking me over, who then asked me, “Are you a boy or a girl”? I simply replied, “yes,” and while the child looked a bit puzzled, she did not say anything else.
I was leaving a friend’s party during winter time and did not realize that it had rained/sleet and while I kissed my friend goodbye on the cheek I totally ate it on the sidewalk in front of my Uber driver; so embarrassing!
The best was when I had to explain to my wife why I had a raspberry on my chin after I got home!
My most embarrassing moment is like many other’s. This occurred several years ago. I was dressed in a sexy blouse and short skirt and and heading home after a night at the club in a nearby city. It was late and I pulled on to the freeway exchange and almost immediately was pulled over by the police. I thought it was strange because I am not a fast driver.
So I sat there and was looking in my side mirror waiting to see a large, masculine, midwestern lawman approach my vehicle. I was dreading the obvious look of disgust from him when he asked for my license. I waited for what seemed a long time when there was a sharp rap on the passenger window.
Keyed up with anticipation of the encounter, I, physically, jumped at the noise. A black, female officer stood with a flashlight motioning to roll the passenger window down. After I complied she said, “Hi honey, do you know you are driving without lights?”
I sighed at my stupidity and reached down and turned them on. The interchange was so bright I hadn’t realized I didn’t have them on. The officer asked, “Would you step out of the vehicle?”
I stepped out of my car and walked around to her. I am a small person, 5’4” tall and I was wearing 4” heels but she was still taller than me. She looked down at me and asked where I was headed. I replied and told her home. She then asked if I had been drinking. I told the truth and said no since I knew I had to drive a long way home.
She then asked for my license! I told her it was in my bag in the car on the floor. I opened the door and reached in to get it. My skirt was very short and she may have seen more than what I intended.
I handed her the license and held my breath. She gave me a disbelieving look and said “This is your license?” I must have looked coquettish when I said yes because she asked in an almost motherly voice, “Baby, do you have a NEWER “license?”
I bit my lip and shook my head and said no. She handed me back the license, put her hands on her hips and told me to get home. I felt like I was a teenager caught out late by my mom. If she would’ve slapped me upside my head I wouldn’t have been surprised. I returned to my car and drove slowly home.
I am not sure if it was concern over me or if it was hostility that I was out being dressed. I will always remember being so embarrassed in front of her.
First time driving en femme, several hours back from dropping daughter off at airport, I stopped to fill the car up with fuel. Decided in advance which service station to use, nowhere near home so no-one knew me. Planned to pay at the pump so I didn’t have to walk far nor speak to anyone.
Pulled up, quick look around, just some truckers lined up on one side , none of them looking this way.
So, talked myself through it, head up, shoulders back, stomach in, legs together, reached for the handle, opened the door, swung my legs as elegantly as possible, went to stand and then realised, in my state of panic, I had not undone the seat belt so fell backwards into the car, legs in the air, knickers showing to the line of truckers! Felt such a complete idiot as I scrambled to fix wig, inserts, skirt, undo the seatbelt and climb back out to fill up the car. Then my credit card didn’t work at the pump twice and I was audibly praying that it worked the third time so I didn’t have to go into the shop.. and it worked. Omg! Drive off trying to look cool. Failed miserably.
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