Share that unexpected 'GOTCHA' you got from dressing...

All of you gals have very nice stories that brings a smile to this person.
Nothing super in the Gotch'ya has got me. I have broke a heal, then knocked the taps of another pair of heels on the front steps. I have also had a case of wandering boobs too (strange it seems to always the right one). No gust of wind has yet to give me the MM skirt experance (yet). Had a western hat (aka Cowboy hat with a 4" brim) blow of my firmly attached wig and landed about 50 feet into the water of a public lake. It landed upright and since there were no vent holes, just floated and bobbed on the water. I did recover it with some rope I had in my car.

The second anniversary of my first outing en femme is coming up. It was during a Pride weekend and I wss hanging out in a park where public events were held in the local gayborhood. It was a hot day and as I had no wig (I was wearing a baseball cap) I ended up getting a sunburn in the shape of the top I was wearing. The tan line it produced did not resemble a masculine garment at all.

Also, I remember some drunken goofy 20-something telling me to show him my - quote -fat tits- that same day. Fortunately, he was there with some friends who were reining him in. Little did he know my boobs were hollow at the time. Before I bought my forms, I used to fashion my bosom out of a very sturdy bikini top, which I still have. Despite the nuisance, it was also the first time a guy showed any interest in my female presentation. Not that I encourage anything...

Me? I am a one-girl comedy of errors, a veritable Perils of Pauline.

As I was crossing the busy street in front of the Cherry Creek Mall in Denver, the light changed . Instinct kicked in and I started running...in high heel pumps. A few strides and one shoe came loose. It flipped into the air above me and almost hit me in the head on the way down. I grabbed it quickly and sprinted away wearing only one shoe as I saw a few drivers laughing at me.

I have a beautiful longish midi skirt in autumn colors. It has an elastic waist. When I was sitting in a theatre, I began to stand up not realizing that my heel was caught on my skirt. It started to pull my skirt down as I rose. Fortunately, I sensed things slipping away and plopped right back down into my seat to sort them out.

I can relate to being a truck driver or bus rider staring down at a pencil skirt riding up the legs of a car driver and being the femme wearing that skirt.

I carefully avoid tan lines where I do not want them. One sunny July day in Denver, I went to the Denver Botanical Garden wearing a lightweight embroidered white top and a denim skirt. Sunscreen kept mt from burning but the sun is so intense at that altitude that I got a burn that became a tan later, on my covered shoulders. And an embroidery pattern and a bra strap shadow right in the middle of the burns on both shoulders.

Wandering boobs cured me of wearing cheap sports bras. Having my right boob slide under my armpit was bad enough but when both boobs migrated there, I bought a sports bra that could hold thing together firmly. A little clothing glue on the inside of the sports bra helps.

Another boob story...I was out in the heat and humidity while wearing cheap silicone breast forms. The backing was a flat piece of plastic against my skin. Before long, I had a sweaty pool, not under my armpit, but on my shirt front just below each boob. Since then, I bought better quality forms and I back each with a circle of skin-colored terry cloth.

I packed my cheap breast forms at the inside surface of my bag and then checked the bag with the airline. After the baggage handlers got done with the bag, I had an exploded silicone mess inside my bag. I now pack my breast forms in my carry-on. The TsA is fine with that. I also double bag any liquids in my airline checked baggage.

I removed my pencil skirt while still having my high heels on. I dropped the skirt to the floor and stepped out of it. Not paying attention, I brushed a heel against my leg. It snagged my stocking and caused a whole freeway of runs.

I rented a Mustang convertible in Phoenix and put the top down. It was months before I got all the tangles out of my wig.

On the same trip to Phoenix, I locked my room keys, both of them, in my hotel room. The desk clerk asked for ID. My male ID was all I had. She acted like this was the most routine thing that had happened that day.

Speaking of wigs, I was getting the makeover before doing a Glamour Shots photo session. I was wearing my wig. While doing my hair, the stylist snagged my wig. I felt things slipping away and grabbed the wig just in time to avoid being scalped. Now I style my wig separately.

On the painful side of things, I bought a gorgeous pair of tall boots in Boston one winter. I wanted them for a long time. They were my first tall boots. But they were too narrow for my feet. I realized that after wearing them all day and subsequently losing a toenail.

Along the same lines as your experience, Shelby, but with an enhanced eew-w-w-w factor: I tried biking en femme around Crown Hill reservoir in Lakewood, just west of Denver. In the evening, lots of flying bugs come out. I learned quickly to wear a top with a high collar. Crumbs are manageable but flying/crawling bugs at 30 km/hr on a bicycle...eew-w-w!

For a whole book of these mishaps, see the book by Kathy Hamilton, Oops! Adventures and Minor Mishaps of a Tgirl about Town.

One I experienced a few months back.
I started letting my hair grow long and at that time it was long enough to reach my shoulders. One night when I was in the shower I turned my back to the shower head and tilted my hair back to get it wet and wash it. I suddenly had what seemed to be one of the most feminine moments I have felt when the thought crossed my mind that "this is how women do this."
Now I know that everybody has their own way of washing, but in mind at that moment it was a really feminine moment. Today, its the norm.

I've mentioned here many times that i started dressing in my mid-fifties. I bought and purged a few pairs of panties before telling my wife that I'd tried hers on and liked them. She had me model the ones I'd tried before going shopping together at the local Kohl's. I walked around the store while she picked out half a dozen really nice pairs of panties and thongs for me. One pair was a cute pair of bright yellow bikini panties with a lace detail around the waist and legs.

A week or two later, we had a family event at the house and i was playing on the floor with one of my toddler grandsons. I'm sitting on the floor with several people, I cannot remember who, sitting on the couch behind me. I reach back to pull my t shirt down and feel that my shorts are about an inch or two below the waistband of my bright yellow, lace trimmed panties. I made an adjustment without turning around but there is no doubt that some in my family know that, at least on that day, I wore panties.

I'm still curious about which family members saw the evidence.

LOL! You took me back in time with your post. I did experience the same thing back in the late 80's when the time-share market was so rampant. We(wife and me) were at a time-share sales presentation in Orlando and staying as their guest in a 2nd floor condo. It was stocked with all the sale props including champagne and the cheese, crackers and spreads. We sat on the balcony enjoying the drink and snacks while over looking the skyline of the Orlando-Kissimmee area. It was in the late fall and felt wonderful. I was in a knee length blue dress with a deep v-neck I had liberated from my sister-in-law and matching heels, I was into the moment. Crumbs in the cleavage aren't comfortable or sexy!

I did basically the same thing the other day dropping some crumbs in my bra. I reached under my blouse and shook them out, my wife was watching the whole thing and just rolled her eyes and sighed. :doh::heehee:

I don't know if this is exactly what you mean but the first time I tried to use an ATM with full acrylics on was a nightmare, lol. A true comedy of errors. I could not for the life of me navigate that touch screen and I kept looking in my rear view mirror hoping like hell another car wouldn't pull up behind me while looking at the camera and wondering 'what if my bank wants to know why a woman was accessing my acct at 10pm on a saturday'

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Originally Posted by franlee

LOL! You took me back in time with your post. I did experience the same thing back in the late 80's when the time-share market was so rampant. We(wife and me) were at a time-share sales presentation in Orlando and staying as their guest in a 2nd floor condo. It was stocked with all the sale props including champagne and the cheese, crackers and spreads. We sat on the balcony enjoying the drink and snacks while over looking the skyline of the Orlando-Kissimmee area. It was in the late fall and felt wonderful. I was in a knee length blue dress with a deep v-neck I had liberated from my sister-in-law and matching heels, I was into the moment. Crumbs in the cleavage aren't comfortable or sexy!

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That was in the time zone my wife and I did the time shere thing too. But so there was only one adult female and one adult male in our couple. Those were the days. We did King Henery the 8ths, Camalot dinner theater and ****hs for free.

Josie asks what if my bank wants to know why a woman was accessing my account at 10pm on a Saturday. The context of this comment is the usual nervousness that many of us experience doing something out and about, particularly early in our days doing so. That is not really strictly our imagination. My bank already uses dual factor authentication and they have asked me from time to time about transactions at all hours of the day and night. I would not be surprised at all if they asked me such a question. Of course, if they did so back when I was just becoming accustomed to getting out and about, it would make me quite frightened. Josie?s concern is definitely realistic and valid.