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?


  • angela

    With the help of a very special experienced lady, I ventured out for the first time when I was about 30 out of town in LA. That you could say was my maiden voyage. And of course it was the most thrilling experience of my life, nervous and excited. Support was very key. I had very nice time and met quite a few people at the Queen Mary in LA. Later at home in in Northern California, that first time in LA gave me the momentum to keep going out and over the years I have developed friendships and relationships with many friends and romantic interests. I am so grateful and happy that I worked up the nerve back then to venture out. If I hadn't I would not have the friendships and relationships I have now. So get out and don't look back. ( :

  • Kim

    I’ve taken a lot of risks and have been rewarded most times with very pleasurable outcomes. One of my most fun and downright naughty times (that’s why it was risky) I went to pay my water bill dressed only in a Wayne Rogers mock neck, gorgeous brown, thong panty bodysuit and Trasparenze STW Noemi 8 denier pantyhose, nude D’orsay heels and chiffon semi-sheer mini– that’s it! I absolutely LOVE tucking in Noemi 8’s ,those gorgeous sheer meshes on my tightly tucked lovely feel so good, makes me instantly wet at the tip, just feminine heaven. So, I park my car in the parking lot of the water company. I get out my lipstick, adjust my mirror on my visor and do my prep. Then, oh so lady like , I exit my car and I wiggle my booty inside, caressed by my silky lovely nylon meshes and thong panty bodysuit – OMG feels so good, my silky chiffon mini whipping up in the breeze showing my little thong underneath! So naughty, so much fun! Then, after paying my bill, I took off my chiffon mini in the parking lot. This is So-Cal, if the Kardashians can do it so can I! LOL! So, there I am, showing off and teasing in my “very naughty feeling” near nudeness, skimpy thong panty bodysuit and sheer pantyhose! OMG! What a gorgeous feeling! The “Naughty-pleasure” as I call it, is absolutely amazing for me at this point! Yes, these pantyhose and tight thong feel THAT good! Wet at the tip? Yes I am – and – LOVING IT! LOL! It only gets better, my meter guy shows up in the parking lot in his truck! He’s smiling as he stops his truck and whistles! I smile and thank him, then I tell myself, I’m gonna flippin do it! So I sashayed my nylon nude booty to my meter guy sitting in his truck! I felt so confident being so nearly nude in the parking lot, my smile was genuine – and he felt it! My bodysuit front thong panty was so thin the gorgeous scalloped darker center seam of my Noemi pantyhose peeked thru both sides – so naughty! So sexy! OMG, was it risky? Yes, I’m sure local law enforcement wouldn’t appreciate my risqué look in public. Was it worth it? OMG, yes, a thousand times YES!!! LOL. I felt SO feminine, SO sexy, SO naughty AND SO turned on I had thee most lovely feminine orgasm in that parking lot, while being admired by a very aroused and turned on middle aged man! The pleasure sooooo lovely it was just heaven! Would I do it again? Probably! LOL. Thanks for allowing me to share ladies. Hugs, Kim

  • Mishael

    Loved your article Kathy, I have only gone out dressed en femme at night and have only driven around for a short while. I have gotten out of my car in a deserted parking lot and walked around a little bit. It felt so good to be out in public in makeup, a dress and high heels. I'm hoping sometime soon to go to a cd friendly bar as my next step in my journey.

  • gail

    Without getting into specifics it seems the times I've been out and about fall into 2 distinct categories.
    1) When I'm fully confident, and somewhat full of myself, believing I'm sexy, attractive, and fully passable I tend to throw myself into areas that could prove problematic, such as working class bars. I've always escaped unharmed, although sometimes just by the skin of my teeth, or the length of my false eyelashes. The thrill that these escapades afforded can't be overstated, but part of the thrill, at least for me, is the thought in the back of my mind is fuck off this is who I am buster. Get over it. I think that now CD has become more acceptable this attitude has diminished somewhat, and I kind of miss being considered somewhat foreign, a little exotic, and even a little threatening to certain sense of what reality really is.
    2) When I'm out and about but without any confidence, with no sense of my attractiveness, much less sexiness, and I'm positive everyone sees through me, and rather than shocked they are contemptuous, or even worse bored. When this is my frame of mind I tend to frequent accepting haunts such as gay or even lesbian bars where inevitably I'll find a friendly ear to bend with my sense of disillusionment with my looks and my life,
    At some point I'll notice the friendly ear's eyes glaze over, and I'll know the ears are no longer listening, but I keep right on talking more to myself than the anonymous ears, and this always leaves me with bad taste in my mouth, and a commitment to never go out in that frame of mind again.
    But of course I do.

  • Abbie

    I have never ventured past the outside balcony of hotels or my condo. I do hope for a day when I look my most En Femme and go out into the world. The other me is ,,well,, scared but as for Abbie, I can't wait. If my neighbors find out so be it. Que Sera Sera. Kathy thank You for your articles, through your strength and writings maybe one day this girl could have a smidgen of courage you possess. I applaud you. Please keep writing , you are an inspiration.

Leave a comment

Please note, comments must be approved before they are published