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…..


17 comments


  • Tanya

    Do you still cross dress to the same extent as you did when you first started? – No. Just like the post describes I started with just wearing a bra, panties and hosiery. But now feel only fully satisfied when I fully cross dress with make-up and wig and accessories. I am surely in the guestimate of over 80% who started with the underwear basics, now fully cross dress.
    How does the quantity of female clothes (from En Femme or other sources) you own relate to the number of male clothes you possess? My male clothes still far out number my female clothes, but my en femme wardrobe is slowly catching up.
    Have you ever contemplated or undertaken minor (or even major) cosmetic surgery to make you feel and look more feminine? No, this has never been a desire for me.
    Comparatively, do you spend more time cross dressed or think more about cross dressing than you did, say, 3 years ago? Absolutely yes! I remember when my New Years resolution would be that I will stop cross dressing or at least make a concerted effort to stop. Now my New Years resolution is to cross dress as much as I possibly can and to add to my wardrobe and accessories.
    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? No, the desire to out in public is actually less than it was when I was younger. Although, I wouldn’t mind meeting and getting together with other cross dressers at a discreet or private place.
    Have you ever plotted a short holiday or vacation to spend a few days or even a week en-femme? More like fantasized about something like that.


  • David

    So many good questions here, I have a lot of different answers to these. I started dressing at 13 and didn't really think much of it but looking back I really wanted to dress daily and was forever denying it x


  • Ross AKA Rosslyn

    Where do I start? For me it started with a Halloween costume (Princess Peach), it was one of the most fun nights out I’ve had. A short while after a friend of me and my wife’s suggested that we should go out with me fully dressed as a woman, to which at the time both me and the wife said absolutely not. But that suggestion put a bug in my ear and I started to think about it, more and more as time went on. I decided that I was going to tell my wife that I wanted to try, so one night while we were still up after hours just hanging out and talking I worked up the courage to talk to her about it (it took more than liquor to do this but I’m not going to elaborate). Amazingly she was very cool about it and supportive. We almost immediately started planning a trip out of town for me to go out fully dressed as a woman (jumped right into this). Luckily I’m fortunate enough to only live 90 minutes from Provincetown, MA. We booked a room and planned out our trip. I’m also lucky that we have a friend who lives and works there and also does drag. He did my makeup for the first time (he kept saying how he couldn’t believe he was doing this) then we hit the town bar hopping. At first I was nervous and I did get a few awkward looks at first. But that all went away when I started getting lots of compliments (a group of women there for a bachelorette party even asked to take a picture with me). I just started having soooo much fun. I didn’t want the night to end. After it was over and we were back at our room and washing off my makeup I still couldn’t believe my night. Shortly after I told my wife I wanted to do it again and immediately booked the same room for my birthday weekend. We now go a few times a year (like I said it’s a short drive and we have a friend who lives there and let’s us stay with him now so it’s a fairly cheap weekend). One thing my wife has said about my dressing is that “it’s not fair, you look better in a dress than me”. lol. Haven’t really considered going past this. I am straight and happily married, I just thinks fun and exciting to go out as someone different once in a while. Only thing that has really changed is that now I’m wearing panties more often (still wear boxers to work as I work in a factory and have to change when I get to work) but I now have more panties than men’s underwear. One thing I know I want to do is practice my makeup more and get better at it, which is tough at times. Otherwise I’m happy with where I’m at


  • Jonathon

    What about dressing on Halloween if you never dressed before but did it on Halloween it was fun and I enjoyed it and would like to learn more and tips on what to use for hair removal


  • 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.


Leave a comment

Please note, comments must be approved before they are published