5 Questions Crossdressers Dare Not Ask Themselves

crossdressing questions and tips

5 Questions Crossdressers Dare Not Ask Themselves

Without a doubt, the need to crossdress is something every crossdresser is born with; it’s an indisputably built-in part of us.

For most participants it brings great pleasure and greater awareness of the differences between genders. It also provides valuable time for many men to escape from the hurly-burly of the modern world and relax, letting their feminine side rise to the front and watching the world go by from a different perspective.

Most crossdressers are pragmatic enough to know that they can never ever give up this need, this want, this overpowering desire to crossdress. Even though some of our community purge (an awful word!), they are likely to start crossdressing again, almost as sure as the sun will rise in the east!

There are those who say crossdressers are delusional, in their En Femme dress or skirt and top, that they lose sight of reality when the so-called pink mist descends on their thought processes. No, sorry, I don’t agree. We are as sane and reasonable as the next person. It’s just that we do, I must admit, have the tendency to avoid asking ourselves some searching questions about our dressing—to which, perhaps, we don’t really want to know the answers!

What are these five questions?

  1. If crossdressing, for many, is simply about wearing women’s clothes because they enjoy the feel of the fabrics, the sensuality of the silks, the swish of the En Femme skirts and the variety of colors and styles on offer, then why do so many crossdressers feel the need to wear bras and breast forms and figure shapers, wigs and makeup, to give themselves the complete appearance of a woman? Is it, therefore, not the latent desire to be female which drives them to dress, not their admiration for the clothes?
  2. If crossdressing is frowned upon and misunderstood by the vast majority of the world’s populace (despite recent great advances in public awareness in the media and elsewhere), why do so many crossdressers offer themselves up for taunts, ridicule and even the threat of physical danger, just by going out and about to show themselves to the big wide world when crossdressed? Are we all masochists at heart?
  3. If there were no negative repercussions with family or job, or no monetary concerns, if most crossdressers had the chance to live and present as a female full-time with no repercussions, would they really do it? After all, many of us long so much for the times when we can be women that to be full-time with no hassles attached would seem to be the ultimate goal, right?
  4. On the basis that most crossdressers all travel on a very similar crossdressing journey to each other, are they not all moving towards the inevitable day when finally there is no choice but to have gender affirmation procedures? In other words, will we all one day end up being full-time women?
  5. Why does dressing like a woman, making our appearance as perfectly feminine or as convincing as we possibly can, temporarily alter the perceived sexuality of some crossdressers? There aren't many crossdressers who will say from the outset he is gay or bisexual—yet a fair number of our community are prepared to engage in relations with another man when they are crossdressed, aren’t they?

Food for thought, yes? I dare you to answer….

However, I have to say that I don’t for one minute pretend to have the answers to these questions, nor do I believe that they apply to everyone in our crossdressing community—just many of us.

I also know there are many crossdressers who are more than content to occasionally parade around indoors in their En Femme finery without ever having the wish to leave the comfort of their bedrooms or homes or meet others in the community, but I’m not one of them.

For those of you who feel similarly, what’s your take on these questions we avoid?


19 comments


  • Patricia Kay

    5 Questions and 5 Answers

    Question # 1: Is it the latent desire to be female which drives me to dress?
    Answer: Yes. I feel I am a truly a woman and therefore I want the experience of being a woman, especially the look and feel of wearing women’s clothing and accouterments.

    Question # 2: Why do I offer myself up for taunts, ridicule and even the threat of physical danger?
    Answer: This is indeed a real concern of mine. But presenting as a woman is important to me, not because I am a masochist but because I want to be seen as a woman and have real life experiences as a woman. Yes, I am concerned about my safety but the more I get out and push my bounds in public the more comfortable I become and the more I find my fears are unfounded as long as I do not do things or go places that put my safety at risk.

    Question # 3: If there were no negative repercussions to live and present as a female full-time with no repercussions, would you really do it?
    Answer: Absolutely, without any doubt and without any hesitancy. Since I feel I am truly a woman I would not hesitate to live and present as a woman 24/7/365 if there were no limitations or repercussions. Unfortunately, this is real life and not my current situation so I have to satisfy myself with the choices I have made and take advantage of the few opportunities I have to be Patricia.

    Question # 4: On the basis that most crossdressers travel a similar journey, are you moving towards the inevitable day when you finally have gender affirmation procedures? Will you one day end up being a full-time woman?
    Answer: I have been slowly planning for years for that day when I can hopefully become a female in body as well as being one psychologically. This includes hair removal and getting diagnosed as a MtF transsexual. I have also sought out resources for HRT, and surgery to allow me to become a fully functional female. So, it is indeed my hope that one day I will be a full-time woman.

    Question # 5: Why does dressing like a woman, and making your appearance as perfectly feminine or as convincing as you possibly can, temporarily alter your sexuality, including being prepared to engage in sexual relations with another man when you are en femme?
    Answer: I cannot answer for anyone else, but yes, once I become Patricia I feel I am a woman and I want the experience the physical pleasures of being a woman. This includes my being engaged sexually with someone who is willing to see me as the woman I am deep inside. It is difficult to explain how feminine I feel and sexually open I am when I present as a woman.


  • Angela

    I am all five of those things to a tee. 100%!
    How do you know me so well Kathy?
    YES WORLD, I want to be a woman full time!
    Hugs and kisses, Angela


  • Carol

    When en femme, I am a woman. I see myself as two different people, one male, one female. If I am out as a male, having sex with a man would indeed be homosexual, and certainly not on my to do list. When I am out as a woman, sex with men is the natural order of things. Just my outlook on the subject.


  • Barbara

    For me it is more than the feel of the clothes. It always has been. It is the feeling of what a girl might feel like or as I am no older what a woman would. I agree if it was just the feel of clothes why would I take makeup lessons, wear body shapers, breast forms earrings and just about everything else En Femmeme sells?

    I love feeling what a woman might feel.

    Which led me to experience dating men and being a woman with a man. I got up the nerve one night. Actually met a guy I was chatting with online. Very nice man who knew all about me and me about him. He treated me as he would a woman….and I fell into the woman's role. I loved it!!

    If that makes me gay..so be it.


  • Elena

    My answers: 1) Of course, I enjoy a lot wearing fememine clothes and making up in order to take pictures to share in social net works later. 2) Alright, I'm afraid if someone of my family find out my secret. 3) , 4) and 5) I'm absolutely happy as I'm now and so I needn't to be a full-time woman so far.
    My crossdressing is something that I do in private although someone has seen me in the street or in the social net work, thinking that I'm a real woman,
    My best regards from Spain.


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