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…..


  • Donna

    Thanks for the information Kathy. This article was spot on! When I first started to dress, I did say that I would NEVER go out in public. But as the years went by and I became more confident, I decided "what the hell." I thought that I'd go out only at night, but never during the day, perhaps go for a walk or a drive. Once again, as I gained more confidence I started going out during the day. I would go to the grocery store or the gas station, or even lay out in the sun in or sit out on the patio. My point here is that rather than feel ashamed or embarrassed, I completely accepted and embraced my femininity. However, it took years for me to get there.

  • angela

    1. Yes I still cross dress to the same extent as when I first started and I try to keep up with the latest fashions so long as it fits my budget.
    2. The ratio of female to male clothing is three to one.
    3. Yes I have contemplated undergoing minor procedures if it will help enhance my feminine side. I have had electrolysis.
    4. I think of fantasize about my feminine presentation every day. Mostly I think about how I can improve my presentation.
    5. Honey!!!!! I have been going out for years locally and out of town. But what a thrill it was the first time I stepped out in the world. It was heaven.
    6. I try to set aside a two vacation trips out of town, enfemme, mostly to Los Angeles but I would love to go to other places since I am very adventurous.

  • Jessica

    I have been cross dressing for over 25 years now. The only thing missing from my form is breast forms which i am hoping to buy very soon. My mans clothes to woman s clothes ratio is around 4 to 1, that s 4 woman s to every man piece of clothes that i own and have been buying more woman s clothes lately. But being retired no i have a limited budget do can not afford to expensive clothes. I have been thinking more and more of going outside dressed as a woman although i have done that before but mostly at night. I always wear some type of woman s clothes every day. right now i am fully dressed as a woman which i wore under my mans clothes when i went out today. I started wearing woman s clothes at an early age around 15 or 16 years old, i have always loved being dressed as a woman i just feels right to me. I hope this will help other people the dress as a woman. Thank you.

  • Steven

    do i still cross dress the same or more yes i do, the amount of clothing to male is omg way more female then male, have i ever considered, yes i have considered but i’ll be honest i want to keep my penius, yes i do think about it more and do more then i did three years ago, yes i have been dressing in the day time and sorta letting people see what i wear if they look hard enough, i am an over-the-road truck driver and i try to wear short shorts while driving and even bras and false breasts even started taking pueraria mirifica to see what hormone replacement therapy works

  • angela

    1.Yes like most crossdressers and transgirls I express my female side to a greater extent then when I first started. At 11 with access to my mother's and younger aunt's wardrobe I discovered and explored this wonderful world. My parents stopped me when I was 14.At 24 and now living on my own I picked up where I had left off. I had the freedom to develop all aspects of my female persona; wardrobe, makeup, hair, demeanor, walking, gestures until a female identity emerged after much effort.

    2. My female wardrobe far surpasses what is left of my male wardrobe. For example; I have two pair of male shoes for work but I have 25 pair of female shoes of a variety of styles.
    3. I have had electrolysis to remove what little chin hair and upper lip hair I had. In general I do not have much body hair but do shave my legs and armpits. I let my hair grow long almost immediately when I left home. My future plans include some FFS nose, brow bone and forehead reduction and finally HRT non op.

    4. I spend the same amount of time en femme as I did 3 years ago, if not more. I am 16/7 8 hours in male mode for work. I do go out mostly to clubs and bars restaurants and a local social group.

    5. Yes. I spent one year refining and perfecting my female side before I felt I was ready to go out in the regular world first at night then gradually some day things. When I go out it's usually with other tg friends or if I have a date. That is another taboo I have broken. I finally came to terns with my sexuality after some careful contemplation,
    I'm in a very happy place at this point of my life.

    6 I have taken small vacations to SF, LA and San Diego mostly for trans conventions, pageants and night clubs. I feel very happy to be exploring this life and so many doors have been open in to this universe since I first started going out.

Leave a comment

Please note, comments must be approved before they are published

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.