Saturday, July 21, 2018

Risk and Reward While Crossdressing



By Kathy Hamilton


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 8th 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?

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