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?


  • Tina

    I Love everything about Femme Life and continue my journey, crossing one border at a time, Love being Tran!! and YES to your questions.

  • Steff

    For me i love mixing masculine and feminine so i dont want to transition
    I get too turned on mixing genders
    In my world i d love to b free to wear light makeup stillettos a pretty dress or skinny jeans my panties and bra get my toes done and have my manly parts switching between m and f or mixing the 2
    Just me

  • Maxine

    Pardon my late response to an article that has been out there a while. I started dressing only a couple years ago, so most of the responses predate my new-found desire. These questions pretty much raced through my head as I tried to figure out why I am dressing. The first question I still wonder about myself. What started out as trying on my wife's panties quickly (within 6 months) escalated into my own corsets, bras, panties, breast forms, thigh high boots, to my most recent En Femme order of a high/low dress, skirt, pink shirt…you get the idea. I haven't gone to wigs and makeup yet, but possibly see it coming. I do enjoy the feel of being female for a while, but also enjoy becoming my man-self again. Even though I dress, I still love both sides of me. I hope that makes sense. The second question doesn't apply to me…at this time. As they say, the future is a mystery, yesterday is history, and today is a gift. At this time, I am content to dress at home while my wife is away, or at a hotel while working out of town. It is sad that people are cruel to those they don't view as "normal" (I wish someone would define "normal"). It seems to be part of the human condition. Remember as children, in school we all kind of "went along" with whatever the popular thought was in fear of being singled out for ridicule. It is scary, but very liberating to shake that train of thought. By my junior year in high school, I didn't care what others thought. A great sense of humor was my weapon of choice, and soon found others shaking the same yoke. At my 25th class reunion, the first I had attended, the number of former classmates coming up to me and thanking me for that was overwhelming. The CD/TS community has always been an easy target. Hopefully it is changing. I've read many posts here and elsewhere, the anguish, hurt, and frustration of feeling born the wrong gender. They deserve our compassion and understanding. I hope and pray they find happiness and contentment. Question 3 probably ties with my answer to question 1. I enjoy being a man. However, my CD time has helped me grow as a person. Even though I've been married for over 20 years, speaking with women has always been very difficult. I find now I am more at ease around women. My wife even noticed I seem more relaxed lately. I am also exercising and losing weight (to fit better into some of those sexy outfits, LOL). For me, it feels cross dressing has made me a better man, again, if that makes sense. Would I choose to live full time as a CD? No, but I will not ever give up this part of me. Question 4, for me, I doubt it. Question 5, I have not had those desires as of now. Again, who knows what the future holds. I am very in love with my wife, and have no interest with being with anybody else, man or woman. There seems to be as many reasons why we do what we do as there are people that do it. I have not tried labeling myself as anything other than who I am. MY OPINION is when a person tries to label themselves, they may feel that there is something wrong with them. There is nothing wrong with what we do, no matter the reason. Why label it? APPRECIATE AND ENJOY IT!!!

  • gail

    Very interesting questions, and, at least for me, very telling,
    For many, myself included, crossdressing is a gateway to further sexual explorations, and the first concrete step to full transition.

  • gail

    Great article.
    Overall I believe you're essentially correct in your cross dressing generalizations, and in what direction, given a perfect world, we are all heading.
    Of course given it's arguably not a perfect world, and never will be, the road for many of us will have twists and turns, some dead ends, and some that lead far astray from what for most, if not all, is a common goal.
    The goal is to bring, as much as possible, our bodies and our minds into harmony.
    Understood in this fashion it's easier to see how some may find harmony with what others might consider just a partial journey.
    This doesn't negate or deny our common goal, only that contentment can be found by many well short of what all of us believe to be our most fulfilling destiny.

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