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

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?

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.

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!

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....

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.

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.

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.

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....

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.

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.


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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.

Does dressing at work count?

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.

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!

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.

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.

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.

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!

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.

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!

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.

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

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.

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

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

As I worked with a uniformed crew in a large facility, many days under my loose fitting uniform I would be enjoying full lingerie.
There was an employee health fair in one of the ballrooms and folks were lined up barefoot to get their BMI checked. Not only was I wearing sheer stockings but,
my toenails were painted beautifully red. I just waited for the right moment, faked a phone call and then left to address the imaginary concerne.

I underdress at work most times I?m in the office except when a colleague from another site is visiting as there would be hugs involved. I work in a national team where I have known people for several years so are quite close.
One time I was helping a colleague and resolved a major computer issue she was having and she said I need to hug you and she did. Not sure if she felt it but nothing said and no awkwardness at all.

When I was younger I think back now on how smart I thought I was but really so naive and took bigger chances then I thought.
For some reason my mother stored my sisters wedding dress underlining in my room, it didn't have lace on it but it was long and silky. One night I woke up at around 2am and for whatever reason I decided to put it on and a pair of pantyhose. I would leave my room and go to the living room window and I would just stand there and let the street light shine in and I would just enjoy looking down at my pantyhosed feet and the shiny slip.
I never thought if someone would have heard me got up to see who was walking in the house, I would have been totally caught because I would have had no were to run back to my room.
Another time I went bike riding with my wife and don't ask me why I wanted to wear a bra on that hot summer day. There were a lot of people riding along us and I was usally riding behind my wife and at one point I went ahead of her. She stopped me and told me when I reach down for the handle bars my shirt tightens up and the bra is in full view. I'm sure there were a lot of people who rode behind me to see it. My wife was very upset that day but I thought it was a little thrill.

Very early in my relationship with my now spouse of 30+ years we were meeting each other at a friend's house for a party. I do not know why, but I decided that I wanted to wear one of her, I know, bad me, tight and lacy white teddy with lower snaps (thank goodness) under my clothes to the party. I also did not expect that we would be leaving at the same time, but as we arrived separately we had our own cars. I was panicked that when we got home how was I going to explain wearing the teddy and not be in big trouble. So as I was driving back I was trying to remove the teddy, again thanks to the snaps, I was somehow able to do that while driving and not crashing, talk about distracted driving.

I was able to get home and get it back in the lingerie drawer and she never knew. Certainly not the smartest thing I have ever done.

Mercedes XOXOXO

Probably the biggest informational risks are when I told persons who knew me that I was a crossdresser. I have no actual control over what they did afterward.
Biggest physical risk would be when I have been dressed and in public. The anxiety/stress/distraction of it all blinded me to my surroundings and I ran a red light on a couple of occasions. One time, someone pulled out in front of me on a multi-lane highway, and I reacted in time, but the car to my left hit the other car. I was dressed pretty and I was almost in a wreck.
Beyond that, I have worn "invisible" women's clothing as a man in front of people who knew me. I went to a conference in a skirt, but the day before, a guy I knew was at the conference (when I was dressed in menswear). He was not there on day 2. I have run into one person from that conference since.

I one time was home from and semi-dressed as Christina. It was around dinner time and I went to go get something to eat and realized I didn?t have anything I wanted. So I decided to go to the store quickly and get something to eat. I also made the decision to just stay semi-dressed and threw on a sweater to cover the shirt and bra I had on. I ended up driving to a drive-thru and getting food from a fast food restaurant.

I was I my early 20's and had some time off before the new year started in Uni so my brother asked if I could house sit and look after the dog for 2 weeks. I was happy and excited too, 2 weeks in an empty house and access to his wife's closet. The day came when they were packed and driving to the airport. They said goodbye and drove off. I was so impatient and excited in those days I went straight up stairs into their bedroom. I remember my knees wobbling with excitement going through my brothers wife's clothes. I picked out of lovely black Jersey maxi dress and slipped it on. Her shoes were too small but I had a pair of cute heels in my backpack so I put those on and put one of her grey cardigans on. I went downstairs feeling pretty Euphoric and put the kettle on. I sat at the kitchen table and pet the dog then.... to my horror I noticed the shadow of a car coming into the driveway through the perspex glass beside the front door. I jumped up, pulled the dress up and ran as fast as I possibly could (in heels) up the stairs. Halfway up I could hear the keys in the door. Instinct led me into the bathroom where I locked the door and started taking my heels off. My heart felt like it was going to pop out of my chest. I heard my brought run up the stairs, open the door of his bedroom, shuffle around then close the door and run back down stairs, out the door and into the car. As I heard the faint sound of the car drive away I almost fainted! The dress was also off me now, Phew!

Another time a few years later I was living with 2 other housemates. We all worked 9-5 jobs in the city. I had a couple of days off. One morning I was feeling quite fem so I put a dress on with some flat saddles. I went downstairs made some breakfast and had a coffee. I must have been 30mins downstairs. I went upstairs and into my room. After about 10mins I hear my housemates door open and hear her walk to the bathroom. Yikes! Ends up she was feeling unwell and didn't make it into work.

I've taken a number of risks and gotten away with them. I think I just love the thought of getting caught.

My job has occasions where I work late or overnight and typically alone. On a number of occasions I have taken the opportunity to be "one of the girls" in the office. One time in particular i was in the office alone overnight. I had brought in a complete outfit. I used one of the bosses offices to change into panties, bra, pantyhose, black short skirt, grey satin blouse, black FMPs and blonde wig. I felt wonderful, imagining myself as just another one of the girls at work. It was quite early in the morning, 2am-ish when I heard a noise at the office entrance (thus was in a office building) I scurried into the bosses office, lights off, closed door and listened as the security guard walked through checking the office. Thankfully he didn't check the office i was hiding in! Aboutv5 minutes later, he left. I wonder what i would have had to do to convince him to keep my secret.
There have been other risky moments I've taken.

LaurenRenee, I've done similar a couple of times many years ago. I stopped doing it after almost getting caught at the exit to the building. Came very, very close. It just wasn't worth it to risk my job, so I don't do that anymore :) Retirement's coming though. Not exactly around the corner, but getting there. I plan on dressing up at least one day in my last week. Can't fire me then, right? :)

The office stories got me remembering...years ago, I worked in a nice office in So. Cal. This was a group of offices in buildings 2-3 stories tall for companies that only needed a few offices. There was a pretty young lady that worked for the rental company and I would stop by and chat with her from time to time. She was extremely friendly. Anyway, late one afternoon, my boss and the secretary left for the day so I had the whole office to myself. I kept some clothes in my car, so I retrieved them and changed from my drab clothes to a short black skirt, nylons, heels and a purple blouse and a brunette wig. I didn't bother with makeup as I wasn't very good with it back then. Well, as I was working I heard a knock on the outer office door. I went to my door and listened for a second only to hear a key in the door and this young lady call out to see if I was in the office! I had time to shut my office door and lock it before she came into the outer office. The next thing I know, as she was calling out my name is I heard a key going into my door lock! As it started to turn, I turned it back to lock it! This went on a few times - she tried knocking again and after what seemed like an eternity - she left.

I changed back to drab and went down to see her about a half hour later. She said "I stopped by to see you but your office was locked and I couldn't get my key to work!" LOL....whew!

I do wonder what her reaction would have been had she seen me dressed....I know what I wanted it to have been, but there was no way I wanted to take that chance!!

Krissy

When I was living with and dating one of my ex girlfriends she went out shopping, I was trying on a pair of her panties, she forgot something and returned, I threw a blanket over myself, she didn't notice, it was so close. Now I wear leggings most days under my uniform to work, until it gets to warm outside to do so.

Quote:

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Originally Posted by CarlaWestin

As I worked with a uniformed crew in a large facility, many days under my loose fitting uniform I would be enjoying full lingerie.
There was an employee health fair in one of the ballrooms and folks were lined up barefoot to get their BMI checked. Not only was I wearing sheer stockings but,
my toenails were painted beautifully red. I just waited for the right moment, faked a phone call and then left to address the imaginary concerne.

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Why didn't you just line up and get your BMI checked? You may have even gotten compliments on your pretty red toenails. My red pedi is on display 24/7 in my normal feminine guy mode and I get a lot of compliments.

After getting out of work. Parked in the park and ride changed into my 100% girl mode and drive home 18 miles on the N
YS THROUGH WAY. then another 10 miles to my home.
Love Angie