Biggest risk you took to dress that you got away with?

[CharlotteCD]

It's always the caught stories or the close calls that get talked about. Time for something different!

I think we've all been in a situation where we knew that we shouldn't dress, that we knew there was a massive chance of being caught or exposed, but we still did it anyway.

I for instance knew that my ex wife would be out for minimum 10 minutes, maximum one hour. I still rushed upstairs and put a bra and top on regardless because the pink fog totally overruled all sensible thoughts in my mind.

What are the biggest or most stupid risks you took but got away with?

[Genifer Teal]

Risky in a different way, but i've wore next to nothing outfits on public transportation and in a major train station in the city. I was feeling good about my choice because it was the pride parade day, but still looking back.It was a bit of a risky choice.

[Jasmine23]

Trying on my sisters wedding dress, wasn't sure how long I had, but, had to try it on, it was literally calling me 😁, tried it on, next thing the doorbell rang, had to take it off to answer the door, all the time knowing my sister and mom might come and dress still left on bed. Luckily managed to get rid of the neighbour that called around and just had time to get everything back in its place when my sister and mom literally walked in the door, had they came a few minutes earlier I don't know how I'd have explained why the wedding dress was out. Just to note this was after the wedding, I made a conscious decision not to wear it before the wedding even though I had had a few opportunities, but, I felt it would have been wrong to try it on before her wedding, plus was afraid I might damage it. Sometimes the urge is just too strong and you have to act on it regardless of the risk!

[Robyn n TN]

Living alone I don't have the what if someone comes home and finds me dressing but I still have those uh oh moments. One night out with a friend, another part time trans, and we were talking to some female friends and another girl walks up and I turn to acknowledge her and had to turn away and " oh S&%t" I've dated her....

[Georgina]

I was visiting a friend and I was told that one of the family would have a few girlfriends in but they were in a different part of the house. I decided not to change and on my way into the house the door to the room was opened. I continued on in and after a while one of the family came to me and I asked if they had seen anything. I was told yes they noticed you were wearing heels and a skirt. I was then told that the visitors wanted to see me. They turned out to be two lovely girls very interested in my dressing and I had a great time. The friend I was visiting and the rest of her family knew I dressed but the visitors didn't.

[JulieC]

This an interesting question Charlotte!

I have to admit I'm hard pressed to think of any extreme moments where I barely got away with it. I'm usually exceptionally careful about when I dress so as not to be discovered. I did have a minor recent moment. With the weather changes, sometimes you turn on the AC sometimes the furnace. Recently, I'd gotten ready for bed (nightgown, pantyhose, bra, forms..what I usually sleep in now) and realized I hadn't turned the furnace back on and it was going to be chilly overnight. I didn't want to undress just to re-dress, so I went and turned the furnace on dressed as I was. I've still got two (now adult) kids at home, and either one of them could have come out of their rooms and seen me. They didn't, and I set the furnace on and went to bed. I'm getting towards the "eff it" end of the caring scale of people knowing.

[Debs]

Went to Machester City for the night out dressed, now thats where some of my work colleagues go for a night out, but hey ho. The night went ok, but the following day I was just doing a bit of shopping before I headed home. Whoops the man I work with for over 5 years was walking down the same walkway as me towards me !!!!!!, so I didnt flinch an inch and we passed nearly touching shoulders !!. But nothing, obviously he wasnt looking for me dressed en femme. But it was a hold ya breath heart stopping moment.

[OrdinaryAverageGuy]

I'm an early riser, I usually get up between 4 and 5 and have some alone time on the couch in the living room, playing with my laptop or reading. I usually spend this time in a dress, or skirt and top, sometimes with fishnets, always with a bra.
When we have overnight company (which happens a lot) they stay downstairs and most of them don't come up until they hear my wife and me starting on breakfast. These days I wear shorts or leggings instead of a dress or skirt, but still sometimes I have the bra on, figuring that our guests probably won't notice even if they come up before I've had a chance to change.
So far so good....

[alwayshave]

I had a bartender, who I knew as a male and worked at several establishments, serve me in a LGBTQ+ bar and it never registered.

[Heisthebride]

I had been attending night classes at the local community college back in the late 90s or early 00s and had become familiar with the Japanese Gardens on campus. Since it was around Halloween and I did have a wedding gown I naturally put two and two together and thought, "Wouldn't it be cool to have a bridal shot with such a lovely background." I could always blame getting caught on a Halloween prank. I scouted it out one Saturday evening and as I pulled into the parking lot I discovered I was not the only person with this idea. There was an actual wedding happening as I drove up. I made a mental note that Saturday afternoon/evening was not a good idea and decided I would try Sunday morning.

That Sunday I woke up at 6:00am and started to prepare for my wedding shot. After makeup and getting dressed, I loaded my car with my camera, a set of emergency male clothes. I put the hoop skirt in the back of my pickup and climbed into my truck. I pulled my vehicle into the closest spot, quickly scanned the area and hopped out in my wedding dress. After grabbing my camera, tripod and veil, I went to the bed of my truck to get my hoop skirt from the back and slip it on. Just as I stepped into it, I saw a big pickup pull into the lot. I quickly jammed everything back in the cab, including myself in my full gown and now hoop skirt, backed up and pulled away. I made a loop around the block and back to see a construction worker setting up to do some work on the sidewalk right by the Gardens. Construction! On a Sunday morning!?!? But I wasn’t done yet.

The next Sunday, I woke up at 4:00am to prepare for my day. After loading up the truck with the same gear as last time, I got all dressed up and an uneventful drive took me to the Gardens with the sun just brightening the day and the parking lot all to myself. I took out my camera and tripod, this time I just grabbed my my skirt and veil and decided it's now or never. I left the relative safety of my truck behind me and walked the hundred yards to the entrance of the Gardens. I saw that the large wooden door was closed and I breathed a sigh of relief as I discovered the latch was not locked. I felt a little better closing the door behind me but still felt very exposed in such a public space.

I managed to step into my hoop skirt make a few adjustments and get my veil in place before I wandered the Gardens to take my photos. There were so many little places to take a great photo. There was an arching bridge leading up to a small pagoda, a long wooden bridge over the pond and a grassy little knoll with a small waterfall behind it. I managed to walk around for half an hour taking lots of photos before I decided I had pressed my luck enough for one day. I also managed to to make it back to my car without encountering a single person.


becky.jpeg

[LizMichelle]

Wife and I went to a restaurant 4 years ago and I was dressed as Liz Michelle too. Seen an uncle on my dad's side was there, he was with a friend of his. He is not fond of my crossdressing and got lucky. Walked by with him not looking at all. He left before we did too.

[Petra1]

Does dressing at work count?

[BobbiKay]

In the Covid times I would wear a bra and forms under a T-shirt, under a drab buttondown shirt that hid the girls, to my IT gigs. I'd keep a pair of heels in the van to drive in. One night I needed to stop for gas on the way back from a gig. I had taken off the drab overshirt, so it was me and the girls, looking a little shapely in a dayglo T-shirt and jeans with heels, in the bright lights under the gas station canopy. It was pay at the pump, but I am sure that the attendant could have gotten an eyeful in the CCTV camera.

[Susan Smith]

2 year’s ago on holiday by myself in Fuerteventura, I drove to a remote beach in the south of the island, changed into a completely female outfit and then drove for two hours to the north of the island where I was staying, stopping in a quiet business park to change into boyfriend shorts and a women’s polo shirt to go back more discreetly to my villa. Memorable!

[Toni in nz]

My wife and went to an Italian restaurant I was in male mode but had matching pink bra and nickers on male jeans and a male cotton dress shirt, the restaurant was pretty full anyway we finished our meal and I got up and went to the cashier to pay when I got back to the table my wife said you can clearly see my pink bra.
Ooooops.

[Debbie Denier]

Trying on a dress in a shop . The owner knew me so I would model the outfits for her opinion. One occasion a lady came in with her husband. I ran and hid in the dressing room for what felt like an eternity before they left.

[Raychel]

I had times before I came out to my wife, I would get up in the middle of the night for dressing time.
I dont think she ever caught on to why I was getting up. But I will admit that was pretty risky.

And there was times when she went out shopping, that i would also use that time for dressing time.
I will say it was more than once I heard the garage door opening that I would rush to get changed.

Luckily I never got caught, But plenty close too many times.
Smartest thing I ever did was coming out to her.

Now she is an Ex and I live alone, where I can dress how I want whenever I want.

[Ciaocd]

I was underdressing at work - just some cute VS panties. I normally change before heading back home but I completely forgot! I got home and started undressing, unbuttoned my pants to realize my mistake - my wife was in the adjoining room making her way in and around where I was. I quickly threw on some sweats and nothing came of it, but my adrenaline was pumping there for a little bit!

[JesseVF]

Like BobbiKay I wore fairly large forms under a canvas type thick shirt for years at work.
But the biggest single risk was wearing them to bed with her one night. She obviously would have felt them if any snuggling happened that night but did not.

[KrissyTN]

I was about 17 and most of my family was away on a trip. My brother stayed weekends at my grandparents house. Saturday night I had blast trying on my Mom's and Sister's dresses, pantyhose, heels etc, and went to bed wearing a very sexy nightgown with lace. Woke up the next morning, put on some pantyhose under the negligee, some heels and a satin bathrobe. Started making some breakfast and I just got that feeling I should change. I put on some shorts & a t-shirt and about 10 minutes later my brother came into the house.....VERY close call!

[Jillcder]

My riskiest moment was on an overnight business trip on a very warm late Thursday afternoon I decided to go to a liquor store for a bottle of wine. I was wearing a very short sleeveless sundress and wedge heels I somehow ended up in a long checkout line sandwiched between a crew of rowdy construction workers buying their alcohol for the evening. I could feel their eyes looking at me from behind I was nervous and excited at the same time as I exited the store with a couple of them I made my way to my vehicle without any harassment not sure if the made me or not but wow what a feeling.

[danniUK]

All of these stories are teaching me one thing:
I need to be more adventurous!

[Marketa]

Does being drunk (but not wasted) girl in bodycon mini-dress just under my bum going alone from party/club in the city at 5 A.M. to tram counts?

btw. I wasn't going, I was running bare feet (well, in pantyhose) with my 10cm/4in heel in my hand and I still missed the tram for about 20s.

[Sandi Beech]

The scariest encounters are when being caught by my disapproving spouse would have landed me in hot water.

That said. I have had my fair share. One example is having to cut the laces off my corset in order to get out of it quickly. Another instance is jumping into the shower with lingerie on so as to not be spotted and getting the wet clothes squeezed out and hidden before being discovered. Then last year I stupidly suntanned on my deck periodically with sunscreen on my boobs. I never got caught and the tan has faded now, but for months I had to be careful about not taking my shirt off in front of anyone. There were other close calls, but I did get caught a number of times and it never went well. Like the time I wore a women?s single piece swim suit in my pool while she was home. She was quite hot over that. I will not be doing that again, ever.

Sandi

[Simoneshamon]

When i was 18, my then girlfriend was getting ready for prom, she had this amazing gold debut dress, 7 layers of skirts, divine, and i had to try it on. I drove her to a party got back to her house and her parents where out food shopping, i took my shot and put it on, managed to zip it all the way up, 2 minutes later her parents came down the drive way, and you guessed it the zip was stuck, standing there trying hard to undo a stuck zip franticly, he parents came in and shouted my name i said i was upstairs and so lucky they didnt come up, i managed to undo the zip and got it put away before they got to suspicous. Felt amazing but very scary.

Simone xx