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


  • Katie

    Interesting questions!! Here's my take. 1. Some cultures believe we are all both male and female. Most live at either end of the spectrum. We live somewhere in the middle. 2. Are we masochists? Maybe. But for some of us, once you get past the social taboo, we are just being ourselves. 3. Would we dress as women full time. Some maybe but a lot of us probably not. But then there are a lot of women who don't dress as women full time!! 4. Are we all heading for SRS. No. Definitely not. As I said to #1, we live in the middle of the gender spectrum , some closer to the ends than others and many of us sort of drifting back and forth sort of like the tide. 5. Why do normally profound straight people sometimes seek male attention when they dress. Been there. It can be very flattering and very affirming that you have achieved some level of femininity we a man flirts with you as a woman. While I have never fully crossed the sexual line, I have flirted with and gone on dates with guys and had a great time.


  • mike

    as far as can see the articles purty mich are same for me i am 74 years old and stall at home


  • J

    Kathy,
    These are great questions that we all ask ourselves from time to time. As a crossdresser for over forty years, I have to keep my dressing private. I have discussed the issue with my wife, but she is absolutely convinced that crossdressing is a sexual addiction. I own my own business, married for almost forty years,have children, grandchildren and a large extended family. There would be harmful consequences to my loved ones if I was open about my need to crossdress.
    As you state, I have finally come to accept that my need to crossdress is just part of who I am. If I simply had the opportunity to have a long weekend to myself to dress as I choose every few months, I would be very happy. En Femme's hormone supplements are making wonderful changes in my body, and allow me to feel wonderful, in all my roles in my life. I can't share this part of me with my loved ones, but I can accept myself now without being self-critical. Thanks for a very thought -provoking article. Carly J


  • Kara

    I was recently researching why I felt the strong desire to have sex with a man when dressed and found the term "autogynephilia". After much research I found that although this psychological term is very much debunked by many Transgenders, I feel that it nails me perfectly. Now I do disagree that I have any sort of mental illness, but at the same time I feel that my autogynephilia is the basis for me to dress feminine and the urge to have sex with men has become overpowering because of my autogynephilia. In fact, my autogynephilia is so strong that I am now considering SRT.


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