Risk and Reward While Crossdressing

 Crossdressing in public - the risks

Why do crossdressers risk it?

We have all heard of, or experienced, the pink mist which descends on many crossdressers when they are en femme. For most of us, this pink mist usually starts descending a few days or hours before we start getting ready in our slinky En Femme dress or skirt, attired in sexy lingerie, or slipping on some new shoes or accessories.

And once the mist appears we can think of nothing else but getting dressed; getting made up and letting our alter-egos escape for a few hours. Our bodies may quiver with anticipation; there may be an uncontrolled buzz which permeates throughout our being. The cocktail of feelings of excitement and euphoria sweep us along and, soon, we are ready to meet head on and conquer any challenge or obstacle….
Our minds will be in a whirl, our senses dulled by the euphoria, yet invigorated by the feelings which we can barely control. When cross dressed, we can feel infallible!

So, what do we do?
Well, one thing many of us do when dressed is to sometimes take risks; at times very big risks. Risks that when we are not dressed en femme we would never contemplate; it would be irrational, and, well, downright risky!

As examples, let me share with you 3 of the biggest risks I have taken when en femme:

Risk #1: Owing to circumstances beyond my control, close friends of my parents ended up staying for 3 weeks in an apartment on the same floor and directly opposite mine! For the first 4-5 days they were there, I managed to put dressing to the back of my mind; by the 6 th day I was a mess; by days 7-8, I was going crazy: I simply had to dress and go out -no two ways about it, I had to!

On the 8 th night, I waited until I thought they had settled in for the night and resplendent in my En Femme attire, I scurried out of my apartment, past security and out into the night. Aah… freedom again!

The third time I managed to dress and skip out it was a Saturday night and, again, getting out was incident free. Getting back in was a different story…
As I fumbled in my purse for my door access card, I suddenly heard the voices of my parent’s friends right behind me. Always amiable, they wanted to engage in conversation with this woman holding the door open for them. I could hardly talk and mumbled a few, muted replies; my mouth was arid, my stomach churning in fear of them recognizing me. Somehow, after what seemed an eternity, I finally extricated myself from their company, pretending I had to use the elevator to a higher floor.

Still shaking, over 15 minutes later I crept back into my apartment, having walked down 10 flights of stairs, hidden in stairwells, and skulked in shadows until I thought all was clear… and vowed I’d take no more risks going out until my neighbors had truly departed!

Risk #2: One Thursday night when I was out and about dressed en femme, I made the error of turning on my mobile phone. A flurry of emails in my inbox came to my attention and, as we do, I found it hard to resist skimming them.

One mail with the caption “Urgent: presentation needs changing” caught my eye and I decided I could either go to the office an hour earlier than planned the next morning or make the necessary amendments that night

Being elegantly dressed in one of my En Femme outfits, and with an overriding sense of bravado, I elected for the latter. There should be no one else around, it’s almost 9.30pm. Should be no problem, I thought. Go for it!

The security guard didn’t look twice at me as in my slinky dress as I trotted elegantly across the wide-open office lobby, my heels clacking on the marble floor.

I was soon in my office and sat for a few minutes at my desk looking around the semi- dark office, listening to the muted sounds of the deserted building.

As I reached to get the file I needed, my skirt swished against my tights, I felt the stretch of my bra straps against my back and I felt wonderful, felt so content: Oh, I wish I could come to the office like this every day, I thought; I’m sure I’d work even harder than I already do!

Then, suddenly the spell was broken: I heard the main office door open and nearly jumped out of my skin in fright. Oh no…, who is that? Some of my staff, other colleagues, my boss? OMG!

My stomach seemed to fall to my feet; beads of perspiration formed on my forehead and I swallowed hard…, very hard. Nowhere to run, nowhere to hide… Oh, what am I doing here like this?
When two cleaners with their mops and buckets drifted into sight, my relief was so palpable I almost wanted to rush across the office and kiss them…

As I left five minutes later, I vowed no more office visits en femme for me!

Risk #3: Possibly the biggest risk I have taken, though, has been flying en femme internationally as this involves not just one but a series of risks and you are in situations where there is truly “no escape”; you are definitely out of any comfort zone!
Amongst other things, you have to:

  • get to the check-in counter and run the scrutiny of your passport not matching your appearance;
  • pass through immigration, ready for any probing questions about your travel documents, travel purpose or gender;
  • have your hand luggage checked, go through the x-ray machine (hoping something about your person does not precipitate a body search);
  • take your seat on the airplane hoping your neighboring passenger is placid, not a boorish drunk and/or doesn’t talk to you or, if they do, doesn’t throw a fit or cause a scene if they suspect you are not what you seem;
  • interact with the plane staff about meals and drinks;;
  • get off the plane and enter the country of arrival and pass through immigration again
  • get your luggage and find a taxi or train to your destination…. plus a lot more…phew!

  • Definitely stressful, but exhilarating; challenging but greatly rewarding; highly pressured but ending with the elation of: “Wow, I did it!”
    So, big, big risks taken…. but why….?
    If you have an answer or want to share your risk-taking experiences when cross dressed… why not tell us all about them? And what did you learn from them?


  • Jackie

    I’ve x dressed since I was 7 or 8. My mother wanted a daughter really really badly. So is this old black and white photo of me on the beach, I am a smiling little girl in a one piece that has a striped pattern running down the front. Word was that the clothing was a hand me down, and it was all they had for me to wear. I’ve never completely believed that. Many many years later I’ve realized I’m somewhere on the transgender spectrum, and an am intrigued by what it might feel like as a woman to be with a man. Which of course is a whole other label. It is who I am and I fully embrace it. It brings me joy. I remember years ago my gf helped me dress and went to a CD bar for Halloween. I wore a sequined LBD that had skull patterns. It looked hot. I recall how it felt getting attention as I sat at the bar. As we danced. Being propositioned… and how relieved I felt when she stepped in and announced that she was my Domme. I also remember that the barmaid that night was seriously rude, judgmental, or possibly both. She noticed, laughed and said “fuck her, she’s jealous that you look better than she does”. And I really appreciated that. That was a good night.

  • Renske

    Hi my small adventure started in Abu Dhabi, I was there for work and stayed in a hotel, had some nice clothes with me and the usual make-up etc etc.
    One evening I had the urge to get myself nicely dressed up and put on my make-up and looked beautifull, and then I did something I did not expected to do walked to my room door and just walked out and closed the door behind me and had a nice stawl thru the hotel, it scared the s..t out of me because this was the first time I was dressed in pulic.
    I was a little bit lucky that there were not many people arround a couple of small encounters but their reaction was normal so that was a big releive from my side.
    The next day I was still in that state of mind that I needed to wear my nice underwear stockings but I also had to fly back home and I thought who cares and put my male clothes over my nice ligerie and there we go to the airport.
    Ofcorse no body could see what I was wearing underneath my clothes I thought, wel I was wrong, after the immigration there was the secutity check with the metal detector and yesss it went of so the security officer asked to get to him, a very sturdy looking officer, and started to bad me down and yes he found the item that made the detector go of, it was my bra and while he padded me down he felt the bra and looked staight into my eys and he sayd nothing he just notted his head so from ok thats different he did went all the way down to finish his search and his hands did go more slowly over my ass then they normally do and he probably felt my little thong sitting on my beautifl ass.
    He looked at me and without any words he made it clear that all was good, and I could continue my way.
    That was a big wowww from my side let me tell you but it was also the most energising moment I have ever experienced, and yes I would do it again just love the thrill.

  • deLora

    A few years ago I was working on construction of a section of the Trans Canada trail. I was a chainsaw operator and rough carpenter. At the time I was totally in the closet, but would occasionally wear a pair of lace top stockings under my work pants and chainsaw chaps. The contrast of the soft stockings on my shaved legs with the mud, dirt, sawdust and hard labour was exhilerating. One day, as we were working we heard screaming from further up the trail. Someone was hurt, so a bunch of us ran to see if we could help. We found a hiker with a badly hurt ankle. There was no way she could walk the 2 km down a steep hill back to the road and the only other way out would have been by chopper and that would have been a long wait for her. We decided that a team of 4 would carry her, using a net that we usually use for carrying rocks. I volunteered to be on one corner of the net. About 500m in I could feel my stockings edging their way down my legs. I was afraid that they would slide right down and appear at the bottom of my pant legs. Because of the way I was holding the net and the rough terrain there was no way for me to do anything about it. What would a bunch of trail workers say if they caught a glimpse of my stockings??!!
    I was so relieved when I felt them bunch up under my foot and I could feel the silicon band just above my ankle. Phew!

    It was soon after that that I learned how to clean oils off the band with a damp cloth!

  • Marla

    I too went into work dressed during a weekend. My place of employment is open 24 hours and I was hoping to stay in my work area to print out some documents. Of course the printer was not working so I had to venture down to another printer in a major common area. Luckily with it being a weekend there was no one down there. Just to get even more brave I went into our company store for a few stacks for the evening. It was a rush knowing any minute I might run into someone I know but that did not happen. Plan on going back in some weekend to work some OT.

  • Dianna

    Loved your story Kathy up until last year I only walked around outside my cousins house where I was able to dress when they were up north but last year I had a make over in Orlando Florida and after the make over josett who did it convinced me to take a ride to Walgreens and I did it was the best feeling I have ever had hearing my heels on the tile floor and being in a skirt and pantyhose walking around.i felt great until I noticed one of my wife’s friends walk in I was scared to death josett told me to stay calm and she won’t notice me and she bought what she needed and left I was at ease so I picked up some makeup and went to the register and the only thing that gave me away was my voice the girl was very sweet she said I should try and use a higher pitch in my voice but she did tell me I looked great that made me feel good. On the way out of the store a guy said to me you have nice legs and didn’t even notice I was a guy. So now I try to go out at least 2 times a month

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