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…..



    I have been dressing since my early teens and I now dress much more than I ever did then. I also have many more female outfits than male ones. Is there anything wrong with what I am doing or am I going to continue until my final days. The one thing I can say is that it relaxes me beyond belief. So is it so wrong for me to continue to do what I love and have a peaceful life. I now live alone and I know some people know about my fetish but what the hell. I don’t tell them how to live their lives.

  • Jay

    I have been wearing leotards tights pantyhose since a boy. Over the years I added I have from the waist down wear red or black toe polish high heels and I go to mistress to be put in bondage and punished 50 years and still going

  • Joan2

    I am a Mature Crossdresser who likes to be Feminine and in High Heels most of the time when not at Work. Although even started to wear shaded Nylons or Pantyhose under my Work Clothes hoping another Female would notice. While I wear a lot of Make-Up am thinking could probably get away with wearing light Make-Up at Work. I really enjoy being Feminine and would like to be full Time

  • Jayne Pinkert

    1. Yes! 2. Over 50 percent of my wardrobe is female and the male side shrinks every year. On days I have to be male I stand in front of my wardrobe for a long time, not wanting to put on male clothes. I have around 50 pairs of knickers and threw away my one old emergency pair of male ones ceremoniously recently. On the none dressed days I still wear bra knickers painted nails and pierced ears with big heart shaped diamond studs.
    3.I self treated with hormones for 30 years and have boobs, which I adore and are a beautiful and empowering part of my soul. I have self harmed to try to stop my male parts functioning , and would have reassignment surgery in a heartbeat.
    4. Luckily I have finished work (I’m 60) so am able to dress more frequently than before.
    i spent years of heartache and denial in hiding my true self in a prominent job in a parochial small town, a mental hell on some days. I have a book on the big site that starts with A, it details my every day experiences as a sissy and latterly trans woman in an amusing yet tragic way. For anyone interested in seeing how you CAN be true to your femme self, my experiences are there. It’s called ‘Unsupervised’ by me, Jayne Pinkert.
    6. I would adore a short break. I did manage about 3 days once , but I care for someone all the time, so it’s really difficult.
    7. I suggest a good question to add would be "When you push the boundaries and do something femme in public that you have never done before, does your soul feel enhanced and lifted afterwards? If it does (mine always does!) , do you feel you should do it again until it becomes normal? It’s surprising how many people love us girls once we show ourselves. It’s just having the confidence.

    What a lovely set of questions Kathy! Thank you so much.


  • Billie

    I dress more now and push the boundaries

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