Six key questions to ask yourself about your crossdressing

 crossdressing questions and advice - where are you

Six key questions to ask yourself to help you determine where you really are at with your cross dressing

I’m sure almost every cross dresser will agree that they are on an exhilarating, eventful, quite extraordinary journey.

However, our journeys may not all be the same in terms of actually how or how quickly we move along or progress. For most of us there are lots of extraneous factors, personal or internal issues and so on and, so, our journey is never a straight road. We don’t perpetually move along at a forty-five degree angle from a standing start, more like up a little; stop and plateau; up a bit more, stop and plateau. At times, maybe we even take a few steps backwards before continuing onwards and upwards.

Our journeys are also unlikely to be without pitfalls, problems and doubts; regrets and recriminations (if we are found out) and maybe even purges (ugh!)—as well, of course, as the indescribable joy and wonder at how we can transform ourselves in our En Femme finery time after time into a very presentable, attractive female…

Every now and then, I know quite a number of us will stop and reflect on what we have achieved, how far we have come—and maybe even contemplate or try to guess where our cross dressing journey will eventually take us. At such times, questions and yet more questions pop into our minds, some of which are recurrent, some of which are new.

From others I have spoken with, the most common questions include:

  • Do you still cross dress to the same extent as you did when you first started? As we all know, it’s almost impossible to stop cross dressing; for those who purge (not a nice thought!), no matter how many times they do so, the need/urge still comes back. For most who have been cross dressing for 2 or 3 or more years, it’s likely that you may have started with just wearing a bra, panties and hosiery… but now feel the need to fully cross dress with make-up and wig and accessories. I’d guestimate that over 80% who started with the underwear basics, now fully cross dress…
    Indeed, you have moved on!

  • How does the quantity of female clothes (from En Femme or other sources) you own relate to the number of male clothes you possess? Almost certainly anyone who has been cross dressing for more than 3 or 4 years will likely answer that the number of male clothes they possess pales in comparison to the number of female outfits, not to mention shoes, accessories and other related paraphernalia; in my case I think the ratio of female to male clothes is something like 25:1…. really!
  • Have you ever contemplated or undertaken minor (or even major) cosmetic surgery to make you feel and look more feminine? Many cross dressers I know initially say they’ll never contemplate or do any such cosmetic surgery and the next thing you know they’ve been for laser treatment for facial hair removal or had a nose job or reduction of their Adam’s apple—but often maintain the associated denials that it’s anything to do with feminizing themselves! Some ask whether having full body waxing or ears pierced count?
    Anyway, when you answer, don’t be shy, you can tell all of our readers what you’ve done ☺
  • Comparatively, do you spend more time cross dressed or think more about cross dressing than you did, say, 3 years ago? I know it’s very difficult for anyone who is still buried in the closet and whose personal circumstances mean they can only snatch rare opportunities to dress but, from what I can see, as most cross dressers make progress they learn to better manage the time available to them to dress.
    They’ll know the routines of their family (if they have one) and when they can make time to dress; they may join a group for regular meetings or outings or may have reached a time in their lives when their children have grown up and left home and/or they no longer have a spouse. Cross dressers are highly adept at finding time, and more time, to dress—often taking risks and chances to indulge.
    I’m betting this is a big yes answer for most readers.
  • Have you gradually been breaking your own personal taboos such as vowing never to go out of the house cross dressed or going out in daylight rather than only at night? If you are honest and think back to your early days dressing, there were things you vowed or promised yourself you would not do—either because of you were too scared to do them or simply lacked the confidence. Now, when you strut down the aisles of the local shopping centre or slip into restaurants alone or with a group of friends, beautifully dressed in your new En Femme outfit, take a moment to pause and reflect on all the personal taboos you have broken.
    Anyone want to claim they haven’t broken their taboos?
  • Have you ever plotted a short holiday or vacation to spend a few days or even a week en-femme? Of course you have! This must be one of the top dreams of any cross dresser; just imagine, being able to take a few days away from the pressures of work and life, escaping from the prying eyes of family and friends and spending a few days or longer presenting and living as a female. For many it is the ultimate experience—yet it can be very hard work and helps you realise just how hard it is to constantly present as a well-dressed, attractive woman.

I’m sure any of our readers can add another dozen or so questions which cross dressers should be asking themselves about their life-long, unpredictable and amazing journey—but one thing is for sure: you are definitely not the same woman you were when you first started out surreptitiously slipping on your first bra and panties all those years ago…..


  • Rhonda Sheer

    Do I cross dress to the same extent? I never just dressed in Bras and Panties; always went full bore but that's Me. My clothes are easily 25:1. I have 7 golf shirts and 6 pairs of shorts BUT 25 dresses, 52 pairs of heels, 4 pairs of "Fuck Me" Boots, 10 skirts, 20 tops, + assorted bras and panties. SO when I dress I dress as if I'm going out. If it's during the day I wear appropriate clothing; not too revealing.

    I go out to "Clubs" often. In season (when my wife goes to Kentucky for her annual six month vacation; LUCKY ME) I get out to The Copa at least once a week usually on Fridays wanting to hook up with a hunk of a guy for good times. Often I am successful but the pickings have been slim.

    My goal for this season is to go to regular "straight" places. Like the local "Ulta" shop……great makeup there although quite expensive, and there's a cute little dress shop on the Boulevard not far from me.

    As for short trips out of town, YES. I often go to Daytona Beach and walk around en femme as no one there knows me but I don't know why I worry. I look nothing like I do as a boy…..NOTHING!!! August 18th, I am seeing a girlfriend over there for R&R…….in the bedroom of course. LOL.

  • Victoria Basdesole

    Have been fortunate to get away for a few days in the recent years with a extra suitcase full of my prized dressup clothes and accessoriesThe thrill and anticipation of being out in public at all hours of the day and night will build in me Finally dressing and stepping out of a hotel room knowing that I did my best job on my hair and makeup are only surpassed when you start getting those smiles of approval from male and female people I pass.Wondering if I have been "made" is no longer because my confidence is at its highest.Highly recommend it if it ever remotely comes possible. It is an important part of moving forward. And thank you Kathy for giving me the forum to tell my story.

  • Robyn

    This article really got me thinking Kathy – thank you!

    One thing I've noticed as my own personal journey continues is that I've become a lot better at shaping my male body to look feminine, with the help of SF's offerings. I'll never pull off the illusion of an ideal woman's appearance, but I'm absolutely positive I'm getting better. A subtle hourglass shape can be created with the proper techniques. SF has been a HUGE help here. Now, if only I could practice more often with my makeup application…. lol.

  • Emily

    1. yes i do, i been wanting to be a female since 2011
    2.I have more female clothes cause i don't own any male clothes anymore
    3.Yes i would if i could afford it
    4. I dress like a female all day everyday and everywhere i go
    5.No cause i have it where i don't give a rats ass what people think cause if they don't like it don't look or worry about their damn selves for once in their life time
    6. I don't know to be honest i would dress like a female no matter what even be in a bikini or bathing suit

  • Carollyn Olson

    Another great and informative article by Kathy. If you are a new CD, take my advise, Kathy is the best and will never steer you wrong. Thanks again, Kathy. Love ya.

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